Davejonesrealty.com Search Results

$2,050,000

The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom vanity, while modern updates enhance the other baths with style & practicality. All new custom Anderson 400 Series windows flood every room with light while preserving the home's historic proportions. The large flat property invites outdoor enjoyment with a tranquil pond, mature 200-year-old trees & fenced-in vegetable garden. A restored English barn with a loft, 11-foot custom insulated steel barn doors, insulated and propane-heated garage, floor drains & updated electrical systems provide space for projects, storage, or entertaining.

4 Beds ⋅ 4 Baths ⋅ 24159893 MLS

The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom vanity, while modern updates enhance the other baths with style & practicality. All new custom Anderson 400 Series windows flood every room with light while preserving the home's historic proportions. The large flat property invites outdoor enjoyment with a tranquil pond, mature 200-year-old trees & fenced-in vegetable garden. A restored English barn with a loft, 11-foot custom insulated steel barn doors, insulated and propane-heated garage, floor drains & updated electrical systems provide space for projects, storage, or entertaining.

382 Weekeepeemee Rd, Woodbury

$1,752,500

Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6,300+ square feet of refined living space that seamlessly blends country sophistication modern luxuries. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6 generous bedrooms, 6 full bathrooms, & two 1/2 baths. Each bath w/radiant heated floors for comfort. Primary suite has 2 walk-in closets, & office space. At the heart of the home is a stunning, brand-new custom kitchen featuring handcrafted cabinetry, an 8-burner gas range, built-in coffee bar, & an elegant butler's pantry. The floor plan offers multiple spaces to live and unwind: a formal living room w/fireplace, a media/game room on the lower level, a dedicated home gym, & two convenient laundry areas. Additional fireplaces can be found in the eat in kitchen, primary suite, & lower level. Heated 2-car garage w/EV charging station & unfinished space above for future customization. The two-story barn offers storage & creative use. The beautifully manicured grounds are a celebration of nature: stone walls & lush gardens frame multiple outdoor living spaces. There are stone patios/walkways, covered porches, & the built-in grill is perfect for entertaining. Tap maple trees for syrup in winter, tend bees & gardens in summer, or press cider in the fall... this home is a year round experience!

6 Beds ⋅ 8 Baths ⋅ 24121221 MLS

Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6,300+ square feet of refined living space that seamlessly blends country sophistication modern luxuries. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6 generous bedrooms, 6 full bathrooms, & two 1/2 baths. Each bath w/radiant heated floors for comfort. Primary suite has 2 walk-in closets, & office space. At the heart of the home is a stunning, brand-new custom kitchen featuring handcrafted cabinetry, an 8-burner gas range, built-in coffee bar, & an elegant butler's pantry. The floor plan offers multiple spaces to live and unwind: a formal living room w/fireplace, a media/game room on the lower level, a dedicated home gym, & two convenient laundry areas. Additional fireplaces can be found in the eat in kitchen, primary suite, & lower level. Heated 2-car garage w/EV charging station & unfinished space above for future customization. The two-story barn offers storage & creative use. The beautifully manicured grounds are a celebration of nature: stone walls & lush gardens frame multiple outdoor living spaces. There are stone patios/walkways, covered porches, & the built-in grill is perfect for entertaining. Tap maple trees for syrup in winter, tend bees & gardens in summer, or press cider in the fall... this home is a year round experience!

509 Main St N, Woodbury

$1,720,000

This exquisite, unique and spacious country cape offers over 6,300 sq ft. of living space. Lovely features throughout the house bring warmth, charm and sophistication. There are coffered ceilings, crown molding, horizontal and recessed paneling, wide board wood floors, window sets, French doors, exposed beams and built ins. The 13 rooms include 5 bedrooms, 5 full and 2 half baths, living room, dining room, custom kitchen with Wolf appliances, 2 offices, rec/media room, exercise room and 2 laundry rooms. Fireplaces are found in the formal living room, kitchen, primary suite and lower-level rec/media room. The two bay garage is heated and has second floor storage. Built in 2019, "The Barn Yard" barn is the perfect workshop and storage space and houses the properties' irrigation system. Additional details include Hydro Air system with 9 zones, central air, radiant heated bathroom floors, driveway alarm, security system and audio system. The property is park-like with mature trees and gardens, slate patios, bluestone walkways, multiple covered porches, cutting garden, vegetable garden, stone walls and its own apple orchard. A must see to appreciate the quality renovations and gorgeous setting. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams. Known as the "Antiques capital of CT," there's no shortage of shops, boutiques and antique homes lining historic Main St.

5 Beds ⋅ 7 Baths ⋅ 24034210 MLS

This exquisite, unique and spacious country cape offers over 6,300 sq ft. of living space. Lovely features throughout the house bring warmth, charm and sophistication. There are coffered ceilings, crown molding, horizontal and recessed paneling, wide board wood floors, window sets, French doors, exposed beams and built ins. The 13 rooms include 5 bedrooms, 5 full and 2 half baths, living room, dining room, custom kitchen with Wolf appliances, 2 offices, rec/media room, exercise room and 2 laundry rooms. Fireplaces are found in the formal living room, kitchen, primary suite and lower-level rec/media room. The two bay garage is heated and has second floor storage. Built in 2019, "The Barn Yard" barn is the perfect workshop and storage space and houses the properties' irrigation system. Additional details include Hydro Air system with 9 zones, central air, radiant heated bathroom floors, driveway alarm, security system and audio system. The property is park-like with mature trees and gardens, slate patios, bluestone walkways, multiple covered porches, cutting garden, vegetable garden, stone walls and its own apple orchard. A must see to appreciate the quality renovations and gorgeous setting. Woodbury designated as Connecticut's "Most charming small town," by Reader's Digest offers tree-lined Main St, parks, playgrounds, hiking trails and streams. Known as the "Antiques capital of CT," there's no shortage of shops, boutiques and antique homes lining historic Main St.

509 Main St N, Woodbury

$1,720,000

Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~ Stunning 6-bedroom, 6 full bath, 2 half-bath, French-inspired estate with over 9,000 sq. ft. of luxurious living space, set atop one of Woodbury's highest points. This elegant retreat features soaring ceilings, detailed craftsmanship, a chef's kitchen, and grand entertaining areas. The main suite offers a private escape, while 3 additional en-suite bedrooms provide comfort and privacy. Ideal for multi-generational living, the estate includes a 2-bedroom guest house with full kitchen and private entrance, plus an in-law suite above the heated 3-car garage. Outside, enjoy a resort-style infinity pool, hot tub, and expansive decks with breathtaking views. Timeless design meets modern versatility. High bid as of 4/24/25 is $525,000. High bid as of 4/25/25 at 9:04 AM is $600,000.High bid as of 4/26/25 at 8:21 AM is 960,000. High bid as of 4/29/25 is $1,075,000. Current high bid as of 12:11 PM on 4/30/25 is $1,300,000.

6 Beds ⋅ 7 Baths ⋅ 24084150 MLS

Auction Opportunity. Please review FAQ and Property Information Package included in the additional documents on MLS (you may have to request these directly from your agent or the auction company). Asking Price is Opening Bid only. Final price will be determined by competitive bidding. All bidding online, opening April 23 at 4pm and ending April 30 at 4pm. Bidding website available upon request. ~ Stunning 6-bedroom, 6 full bath, 2 half-bath, French-inspired estate with over 9,000 sq. ft. of luxurious living space, set atop one of Woodbury's highest points. This elegant retreat features soaring ceilings, detailed craftsmanship, a chef's kitchen, and grand entertaining areas. The main suite offers a private escape, while 3 additional en-suite bedrooms provide comfort and privacy. Ideal for multi-generational living, the estate includes a 2-bedroom guest house with full kitchen and private entrance, plus an in-law suite above the heated 3-car garage. Outside, enjoy a resort-style infinity pool, hot tub, and expansive decks with breathtaking views. Timeless design meets modern versatility. High bid as of 4/24/25 is $525,000. High bid as of 4/25/25 at 9:04 AM is $600,000.High bid as of 4/26/25 at 8:21 AM is 960,000. High bid as of 4/29/25 is $1,075,000. Current high bid as of 12:11 PM on 4/30/25 is $1,300,000.

59 Hillside Rd, Woodbury

$1,700,000

Discover refined country living in this remarkable Woodbury estate set on 33.98 private acres in sought-after Litchfield County. The 4,517 sq ft residence features 4 bedrooms, 4.1 baths, and bright, open interiors designed to capture serene views of distant hills. A spacious deck overlooks the sparkling saltwater gunite pool, creating an ideal setting for relaxation or entertaining. Equestrians will appreciate the immaculate 8-stall stable, 14 lush paddocks, and generous riding spaces surrounded by pastoral beauty. Completing the property is a 4-car garage and the peace and privacy that define Woodbury's countryside. This rare offering combines elegance, comfort, and the timeless appeal of New England living.

4 Beds ⋅ 5 Baths ⋅ 24072926 MLS

Discover refined country living in this remarkable Woodbury estate set on 33.98 private acres in sought-after Litchfield County. The 4,517 sq ft residence features 4 bedrooms, 4.1 baths, and bright, open interiors designed to capture serene views of distant hills. A spacious deck overlooks the sparkling saltwater gunite pool, creating an ideal setting for relaxation or entertaining. Equestrians will appreciate the immaculate 8-stall stable, 14 lush paddocks, and generous riding spaces surrounded by pastoral beauty. Completing the property is a 4-car garage and the peace and privacy that define Woodbury's countryside. This rare offering combines elegance, comfort, and the timeless appeal of New England living.

225 Old Sherman Hill Rd, Woodbury

$1,660,000

Built of the finest materials by Eric Strachan Builders this Georgian Colonial sits atop the estate section of Owl Ridge with stunning 20-mile views. Upon entry the double height foyer is flanked by the formal living and dining rooms. The grand chef’s kitchen in the heart of the home features granite counters, abundant cabinets, Wolf range and wall ovens, Subzero refrigerator with two add’l refrigerated drawers housed in the island. A wall of windows and corner wall mounted gas fireplace frame the eat-in-kitchen area. Off the kitchen is the family room accented with a coffered ceiling and gas log fireplace. A set of dbl doors off the foyer lead you to the main floor primary suite with marble surround gas fireplace, a tray ceiling overhead and ensuite bathroom with separate water closet, shower and hydro tub. Natural light accents the custom cabinetry that lines the large L shaped walk-in closet. The large office and den combo, laundry and full bath finish out the main floor. Upstairs houses three large bedrooms, one ensuite the others share a jack-n-jill bathroom. The large bonus room over the garage with roughed-in bath is perfect for an au pair quarters or additional play room. The lower level features a great room centered by a gas fireplace, game room, wine cellar, full bath and possible sauna location. Close to hiking trails and mins from the shops and restaurants of Woodbury, a 90? drive from NYC.

4 Beds ⋅ 5 Baths ⋅ 170552260 MLS

Built of the finest materials by Eric Strachan Builders this Georgian Colonial sits atop the estate section of Owl Ridge with stunning 20-mile views. Upon entry the double height foyer is flanked by the formal living and dining rooms. The grand chef’s kitchen in the heart of the home features granite counters, abundant cabinets, Wolf range and wall ovens, Subzero refrigerator with two add’l refrigerated drawers housed in the island. A wall of windows and corner wall mounted gas fireplace frame the eat-in-kitchen area. Off the kitchen is the family room accented with a coffered ceiling and gas log fireplace. A set of dbl doors off the foyer lead you to the main floor primary suite with marble surround gas fireplace, a tray ceiling overhead and ensuite bathroom with separate water closet, shower and hydro tub. Natural light accents the custom cabinetry that lines the large L shaped walk-in closet. The large office and den combo, laundry and full bath finish out the main floor. Upstairs houses three large bedrooms, one ensuite the others share a jack-n-jill bathroom. The large bonus room over the garage with roughed-in bath is perfect for an au pair quarters or additional play room. The lower level features a great room centered by a gas fireplace, game room, wine cellar, full bath and possible sauna location. Close to hiking trails and mins from the shops and restaurants of Woodbury, a 90? drive from NYC.

49 Owl Ridge Rd, Woodbury

$1,540,000

Unwind and create lasting memories in your private sanctuary at 55 Good Hill Road, nestled in historic Woodbury. This meticulously crafted residence, boasting 4-beds and 4.5-baths, transcends mere function; it offers a haven of gracious living imbued with enduring charm. Step beyond the grand facade and discover a world of comfort and sophistication. Antique hardwood floors flow throughout, inviting exploration of each elegant space. Imagine grand entertaining in the thoughtfully appointed rooms, each one whispering tales of a rich heritage. Sparkling sunlight dances on the surface of the inviting pool, beckoning you to take a refreshing dip. Unwind afterwards in the soothing spa, or gather with loved ones in the charming pool house for meals and laughter. The expansive 3.67-acre grounds offer endless possibilities for outdoor recreation. 55 Good Hill Road transcends the ordinary. It's a legacy property, where history melds seamlessly with modern luxury. The exquisite chef's kitchen, adorned with top-of-the-line appliances and custom cabinetry, awaits your culinary creations. A beautiful center-cut fireplace serves as a focal point for warmth and togetherness, while a detached garage and large barn with a finished second level offer additional functionality. This exceptional estate beckons discerning buyers seeking a haven of refined taste, enduring charm, and the opportunity to create lasting memories.

4 Beds ⋅ 6 Baths ⋅ 24005954 MLS

Unwind and create lasting memories in your private sanctuary at 55 Good Hill Road, nestled in historic Woodbury. This meticulously crafted residence, boasting 4-beds and 4.5-baths, transcends mere function; it offers a haven of gracious living imbued with enduring charm. Step beyond the grand facade and discover a world of comfort and sophistication. Antique hardwood floors flow throughout, inviting exploration of each elegant space. Imagine grand entertaining in the thoughtfully appointed rooms, each one whispering tales of a rich heritage. Sparkling sunlight dances on the surface of the inviting pool, beckoning you to take a refreshing dip. Unwind afterwards in the soothing spa, or gather with loved ones in the charming pool house for meals and laughter. The expansive 3.67-acre grounds offer endless possibilities for outdoor recreation. 55 Good Hill Road transcends the ordinary. It's a legacy property, where history melds seamlessly with modern luxury. The exquisite chef's kitchen, adorned with top-of-the-line appliances and custom cabinetry, awaits your culinary creations. A beautiful center-cut fireplace serves as a focal point for warmth and togetherness, while a detached garage and large barn with a finished second level offer additional functionality. This exceptional estate beckons discerning buyers seeking a haven of refined taste, enduring charm, and the opportunity to create lasting memories.

55 Good Hill Rd, Woodbury

$1,500,000

Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and mats, stall windows, mounted hay racks, a hay chute, three cross-tie areas, and convenient hay storage with a conveyor system. Additional equestrian amenities include an outdoor wash stall, a 200' x 150' outdoor riding arena with stadium jumps, cross-country jumps woven throughout the property, and a 130' x 65' dressage arena. Five paddocks, 13 outdoor stalls, and ample room for expansion make this an exceptional setup for horse enthusiasts, trainers, or boarding operations. Thoughtfully sited to capture breathtaking views, the custom-built home overlooks the picturesque grounds from a stunning 90-foot wraparound deck. Inside, the cathedral-ceiling great room with a cozy wood stove flows into the kitchen, dining area, and bright sunroom, with French doors opening to the expansive deck for seamless indoor-outdoor living. The main level includes a bedroom and full bath, while the second-floor primary suite offers a walk-in closet and spa-like bath featuring a clawfoot soaking tub.

3 Beds ⋅ 3 Baths ⋅ 24160616 MLS

Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and mats, stall windows, mounted hay racks, a hay chute, three cross-tie areas, and convenient hay storage with a conveyor system. Additional equestrian amenities include an outdoor wash stall, a 200' x 150' outdoor riding arena with stadium jumps, cross-country jumps woven throughout the property, and a 130' x 65' dressage arena. Five paddocks, 13 outdoor stalls, and ample room for expansion make this an exceptional setup for horse enthusiasts, trainers, or boarding operations. Thoughtfully sited to capture breathtaking views, the custom-built home overlooks the picturesque grounds from a stunning 90-foot wraparound deck. Inside, the cathedral-ceiling great room with a cozy wood stove flows into the kitchen, dining area, and bright sunroom, with French doors opening to the expansive deck for seamless indoor-outdoor living. The main level includes a bedroom and full bath, while the second-floor primary suite offers a walk-in closet and spa-like bath featuring a clawfoot soaking tub.

76 Cowles Rd, Woodbury

$1,400,000

Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New 48' Sub-Zero refrigerator & a Sub-Zero 136-bottle wine fridge. Plus built-in professional expresso machine, a coffee-lover's dream! All Wolf appliance suite including a 6-burner gas cooktop, double ovens and microwave. The sun-filled breakfast nook flows effortlessly into the comfortable, inviting family room, where a striking marble fireplace and expansive bay window frame picturesque views of the property and distant hills. A set of sliders open to a large lawn-level deck for summer enjoyment and entertaining. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. Luxurious space features a fireplace, an elegant sitting room, a spa-inspired bathroom with soaking tub, his & hers walk-in closets. Three additional bedrooms with en-suite bathrooms and a large Flex room complete upstairs. Dramatically transformed and enhanced to include all new 7" hardwood radiant floors. The spacious flat, fully fenced yard hosts a beautiful Gunite, heated, salt-water pool and hot-tub waterfall while enjoying the beautiful distant views. Extraordinary - Must See.

4 Beds ⋅ 5 Baths ⋅ 24168051 MLS

Gloriously Peaceful, Private, Magnificent views...This exceptional residence among similar spectacular homes welcomes you with a dramatic two-story entry - designed for both refined entertaining and comfortable living. The heart of the home is a beautifully appointed chef's kitchen featuring porcelain countertops with waterfall island and slab backsplash. New 48' Sub-Zero refrigerator & a Sub-Zero 136-bottle wine fridge. Plus built-in professional expresso machine, a coffee-lover's dream! All Wolf appliance suite including a 6-burner gas cooktop, double ovens and microwave. The sun-filled breakfast nook flows effortlessly into the comfortable, inviting family room, where a striking marble fireplace and expansive bay window frame picturesque views of the property and distant hills. A set of sliders open to a large lawn-level deck for summer enjoyment and entertaining. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. Luxurious space features a fireplace, an elegant sitting room, a spa-inspired bathroom with soaking tub, his & hers walk-in closets. Three additional bedrooms with en-suite bathrooms and a large Flex room complete upstairs. Dramatically transformed and enhanced to include all new 7" hardwood radiant floors. The spacious flat, fully fenced yard hosts a beautiful Gunite, heated, salt-water pool and hot-tub waterfall while enjoying the beautiful distant views. Extraordinary - Must See.

48 Coach Light Dr, Woodbury

$1,400,000

Stunning Renovated Antique Home w/ Scenic Views & Luxurious Amenities. 4 beds, 3 full baths w/ exquisite craftsmanship throughout. As you enter the WOW factor takes hold as you look through floor to ceiling windows over a spectacular rushing brook. Inside, find wide plank floors, recessed lighting, skylights, & a wood-burning fireplace which create a warm and inviting ambiance. The high-end chef's kitchen is a culinary dream, featuring granite countertops, Shaker-style cabinets, & top-of-the-line appliances. The primary bathroom boasts a large glass shower & Waterworks hardware adding a spa-like retreat to your daily routine. Outside, enjoy the beauty of open meadows, the sound of the brook, and a breathtaking professionally designed perennial gardens. Stone outcroppings, specimen trees, and moss covered stone walls enhance the landscape. A renovated in-ground Gunite pool offers the perfect spot for summer relaxation. Entertain in style in the spectacular barn featuring a floor-to-ceiling stone fireplace, soaring windows, and a loft ideal for an office or study. The lower walk out level makes a great gym. 3 car garage with a loft for additional storage. This exceptional property is a rare find-offering privacy, natural beauty in an unmatched setting bordering 20 acres of Land Trust. 10 Minutes to Washington Depot with chic shops, farmer market, Mayflower Inn & Spa. 10mins to Woodbury's organic market, garden store, antiquing & fine dining. 1.5 hours to NYC, 30 min to train.

4 Beds ⋅ 3 Baths ⋅ 24093535 MLS

Stunning Renovated Antique Home w/ Scenic Views & Luxurious Amenities. 4 beds, 3 full baths w/ exquisite craftsmanship throughout. As you enter the WOW factor takes hold as you look through floor to ceiling windows over a spectacular rushing brook. Inside, find wide plank floors, recessed lighting, skylights, & a wood-burning fireplace which create a warm and inviting ambiance. The high-end chef's kitchen is a culinary dream, featuring granite countertops, Shaker-style cabinets, & top-of-the-line appliances. The primary bathroom boasts a large glass shower & Waterworks hardware adding a spa-like retreat to your daily routine. Outside, enjoy the beauty of open meadows, the sound of the brook, and a breathtaking professionally designed perennial gardens. Stone outcroppings, specimen trees, and moss covered stone walls enhance the landscape. A renovated in-ground Gunite pool offers the perfect spot for summer relaxation. Entertain in style in the spectacular barn featuring a floor-to-ceiling stone fireplace, soaring windows, and a loft ideal for an office or study. The lower walk out level makes a great gym. 3 car garage with a loft for additional storage. This exceptional property is a rare find-offering privacy, natural beauty in an unmatched setting bordering 20 acres of Land Trust. 10 Minutes to Washington Depot with chic shops, farmer market, Mayflower Inn & Spa. 10mins to Woodbury's organic market, garden store, antiquing & fine dining. 1.5 hours to NYC, 30 min to train.

39 Painter Hill Rd, Woodbury

$1,275,000

Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces. The eat-in kitchen offers granite countertops, premium appliances, and opens to warm, inviting living spaces including formal living and dining rooms, a family room with fireplace, private den/office, and screened porch. The spacious primary suite includes a fireplace, walk-in closet, and ensuite bath, with three additional bedrooms and updated bathrooms. The finished walk-out lower level provides flexible space for a recreation room, gym, media room, or guests. Outdoor living is exceptional with a wraparound porch, Trex deck, extensive stone patios, mature landscaping, scenic trails, and the soothing sights and sounds of the cascading waterfall. A rare offering combining privacy, elegance, upgrades, and natural beauty just minutes from town.

4 Beds ⋅ 4 Baths ⋅ 24188752 MLS

Beautifully updated and impeccably maintained, this custom Colonial offers timeless New England charm in a private setting with gorgeous views of a picturesque waterfall and babbling brook. Set on beautifully landscaped grounds with an additional lot included, the home features wide-board hardwood floors, crown molding, custom built-ins, plantation shutters, French doors, and three fireplaces. The eat-in kitchen offers granite countertops, premium appliances, and opens to warm, inviting living spaces including formal living and dining rooms, a family room with fireplace, private den/office, and screened porch. The spacious primary suite includes a fireplace, walk-in closet, and ensuite bath, with three additional bedrooms and updated bathrooms. The finished walk-out lower level provides flexible space for a recreation room, gym, media room, or guests. Outdoor living is exceptional with a wraparound porch, Trex deck, extensive stone patios, mature landscaping, scenic trails, and the soothing sights and sounds of the cascading waterfall. A rare offering combining privacy, elegance, upgrades, and natural beauty just minutes from town.

46 Grassy Hill Rd, Woodbury

$1,250,000

Beautiful and stately Georgian Colonial. Custom built on a secluded lot with long driveway. Home has stunning appeal upon entry. The open floor plan is perfect for entertaining with 23 foot ceilings, marble floors, ceiling palladium windows and a balcony that overlooks the family room. Home has a one of a kind spectacular kitchen with large center island for gathering with family and friends. The attention to detail is unmatched with high end appliances and custom cabinets in the kitchen and fine trim work and moldings throughout this home. The house sits on 10 acres of land and offers a 3 car garage. This is a must see!

4 Beds ⋅ 5 Baths ⋅ 170569311 MLS

Beautiful and stately Georgian Colonial. Custom built on a secluded lot with long driveway. Home has stunning appeal upon entry. The open floor plan is perfect for entertaining with 23 foot ceilings, marble floors, ceiling palladium windows and a balcony that overlooks the family room. Home has a one of a kind spectacular kitchen with large center island for gathering with family and friends. The attention to detail is unmatched with high end appliances and custom cabinets in the kitchen and fine trim work and moldings throughout this home. The house sits on 10 acres of land and offers a 3 car garage. This is a must see!

17 Gate Post Ln, Woodbury

$1,225,000

Welcome to 267 Good Hill Road! Nestled on over 19 acres with tranquil brook access, Rosebush Farm is a meticulously preserved antique home with modern flair. The wideboard floors and exposed beams offer charm while the high ceilings and oversized rooms create diversity in use. A staple of the home is the modern farmhouse kitchen, featuring soapstone countertops, and high-end appliances. Ideal for hosting gatherings, the spacious dining room complements the kitchen perfectly just off the keeping room. The keeping room, anchored by a beautiful wood-burning fireplace, offers a cozy retreat and a delightful dining area adjacent to the kitchen. Downstairs, the partially finished lower level provides versatility as an additional bedroom or a comfortable family room. The master suite is a private spacious oasis boasting a luxurious copper soaking tub for relaxation. Throughout the property, charming stonewalls and lovely gardens create an idyllic setting. A standout feature of the property is the enchanting barn, boasting a magnificent fireplace and hardwood floors, ideal for hosting events or stepping out to your own private retreat. Don't miss the opportunity to experience this remarkable antique gem in Woodbury, Connecticut-a property that harmoniously blends historic charm with modern flair, offering a lifestyle of sophistication and tranquility.

3 Beds ⋅ 4 Baths ⋅ 24029093 MLS

Welcome to 267 Good Hill Road! Nestled on over 19 acres with tranquil brook access, Rosebush Farm is a meticulously preserved antique home with modern flair. The wideboard floors and exposed beams offer charm while the high ceilings and oversized rooms create diversity in use. A staple of the home is the modern farmhouse kitchen, featuring soapstone countertops, and high-end appliances. Ideal for hosting gatherings, the spacious dining room complements the kitchen perfectly just off the keeping room. The keeping room, anchored by a beautiful wood-burning fireplace, offers a cozy retreat and a delightful dining area adjacent to the kitchen. Downstairs, the partially finished lower level provides versatility as an additional bedroom or a comfortable family room. The master suite is a private spacious oasis boasting a luxurious copper soaking tub for relaxation. Throughout the property, charming stonewalls and lovely gardens create an idyllic setting. A standout feature of the property is the enchanting barn, boasting a magnificent fireplace and hardwood floors, ideal for hosting events or stepping out to your own private retreat. Don't miss the opportunity to experience this remarkable antique gem in Woodbury, Connecticut-a property that harmoniously blends historic charm with modern flair, offering a lifestyle of sophistication and tranquility.

267 Good Hill Rd, Woodbury

$1,225,000

This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

4 Beds ⋅ 4 Baths ⋅ 24130861 MLS

This magnificent Woodbury colonial, adjacent to 42 acres of open space, offers an unparalleled blend of elegance and tranquility. Surrounded by hiking trails, park like grounds and a serene brook. A light filled interior with soaring nine foot ceilings, graceful arches and an open flowing floor plan. The wraparound mahogany deck invites you to relax and take in the peace and quiet. The back patio, crafted with premium ipe decking, features tiered rock walls and a circular fire pit-perfect for entertaining or quiet evenings under the stars. Designed with quality and comfort in mind this home boasts I-beam construction, two wells, enhanced insulation, and durable HardiePlank siding, ideal for those who value sustainable, low maintenance living. Turn off the outside noise and rest assure this sanctuary will welcome you home with open arms.

68 Whittlesey Rd, Woodbury

$1,210,000

Step into your very own country sanctuary. Set on 6.10 acres, this enchanting property offers a pristine 1860's cape, two-room cottage, 3-bay garage, guest quarters, saltwater pool & spa, barrel sauna & plunge pool, landscaped grounds and a hide-away tree house just a short walk through the woods. The vintage home boasts character and comfort. The living room is cozy with a stone fireplace and a window seat with French doors that open to the stone patio and vine covered pergola. The formal dining room includes a period corner cupboard. The kitchen is styled for easy workability and includes an eating nook overlooking the gardens. There is also an office, mudroom and laundry room on the main level. Upstairs is the primary bedroom with remodeled bath, two additional bedrooms, and full bath. The guest space over the garage has a great room with vaulted ceilings, beams, a kitchenette and a bedroom with full bath and walk-in closet. The separate heated and cooled cottage with vaulted ceiling is perfect for a private office or studio. Lodge-like with exposed beams and a screened porch by the babbling brook awakens your inner peace. Stone steps lead from the lush level lawn to the pool area, the epicenter of summer enjoyment and relaxation. Surrounded by a stone terrace, it includes a pergola covered outdoor kitchen. All on a quiet country road across from Sprain Brook.

3 Beds ⋅ 3 Baths ⋅ 24046438 MLS

Step into your very own country sanctuary. Set on 6.10 acres, this enchanting property offers a pristine 1860's cape, two-room cottage, 3-bay garage, guest quarters, saltwater pool & spa, barrel sauna & plunge pool, landscaped grounds and a hide-away tree house just a short walk through the woods. The vintage home boasts character and comfort. The living room is cozy with a stone fireplace and a window seat with French doors that open to the stone patio and vine covered pergola. The formal dining room includes a period corner cupboard. The kitchen is styled for easy workability and includes an eating nook overlooking the gardens. There is also an office, mudroom and laundry room on the main level. Upstairs is the primary bedroom with remodeled bath, two additional bedrooms, and full bath. The guest space over the garage has a great room with vaulted ceilings, beams, a kitchenette and a bedroom with full bath and walk-in closet. The separate heated and cooled cottage with vaulted ceiling is perfect for a private office or studio. Lodge-like with exposed beams and a screened porch by the babbling brook awakens your inner peace. Stone steps lead from the lush level lawn to the pool area, the epicenter of summer enjoyment and relaxation. Surrounded by a stone terrace, it includes a pergola covered outdoor kitchen. All on a quiet country road across from Sprain Brook.

203 Sprain Brook Rd, Woodbury

$1,200,000

"Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experience the artistry of design. Sunlight pours through expansive windows, illuminating exquisite millwork: coffered ceilings, oversized crown and baseboard moldings, solid raised paneling, and wide-board hardwood floors. Every detail speaks to the builder's commitment to timeless quality. The grounds are thoughtfully engineered for beauty and function-featuring a level yard with industrial grade drainage, a low-maintenance milled crushed stone driveway, double-tiered decking, and a refreshing outdoor shower along with new stone seating area, walkways in the backyard.

4 Beds ⋅ 5 Baths ⋅ 24135665 MLS

"Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experience the artistry of design. Sunlight pours through expansive windows, illuminating exquisite millwork: coffered ceilings, oversized crown and baseboard moldings, solid raised paneling, and wide-board hardwood floors. Every detail speaks to the builder's commitment to timeless quality. The grounds are thoughtfully engineered for beauty and function-featuring a level yard with industrial grade drainage, a low-maintenance milled crushed stone driveway, double-tiered decking, and a refreshing outdoor shower along with new stone seating area, walkways in the backyard.

101 Old Grassy Hill Rd, Woodbury

$1,155,000

A once humble hunting lodge in the forests of Litchfield county became a blank canvas for the vision of an award-winning NYC designer and his partner. Over the decades the property was expanded into a one-of a kind residence of over 6300 sq/ft on 30+ acres. The designer brought his quarter century experience designing for Intercontinental Hotels to bear on this labor of love. The exterior is a mix of stone and wood and is surrounded by blue stone patios. All stone was quarried on site. The home was designed for entertaining and includes spacious formal rooms, a commercial grade kitchen and a dramatic entry. One wing of the home was dedicated to the office which includes high ceilings, multiple workspaces and lots of natural light. The primary bedroom suite takes up the entire second floor and offers a spacious bath, two walk-in closets, a sunroom and a lounge area. Thoughtful and impressive design aspects can be found in the leaded windows, leather surfaced coffered ceilings, unique fixtures and so much more. A stunning opportunity! Please click on the Matterport Virtual tour to fully experience the home.

2 Beds ⋅ 5 Baths ⋅ 24062867 MLS

A once humble hunting lodge in the forests of Litchfield county became a blank canvas for the vision of an award-winning NYC designer and his partner. Over the decades the property was expanded into a one-of a kind residence of over 6300 sq/ft on 30+ acres. The designer brought his quarter century experience designing for Intercontinental Hotels to bear on this labor of love. The exterior is a mix of stone and wood and is surrounded by blue stone patios. All stone was quarried on site. The home was designed for entertaining and includes spacious formal rooms, a commercial grade kitchen and a dramatic entry. One wing of the home was dedicated to the office which includes high ceilings, multiple workspaces and lots of natural light. The primary bedroom suite takes up the entire second floor and offers a spacious bath, two walk-in closets, a sunroom and a lounge area. Thoughtful and impressive design aspects can be found in the leaded windows, leather surfaced coffered ceilings, unique fixtures and so much more. A stunning opportunity! Please click on the Matterport Virtual tour to fully experience the home.

362 Transylvania Rd, Woodbury

$1,075,000

3184sqft Colonial set on 1.42 acre cul-de-sac rd. lot with Barn with loft, Main level Master Bedroom Suite, Soaring ceilings in Open Floorplan, and outdoor patio paradise. Absolutely Tranquil setting! This home is setup for Main Level living with additional bedrooms upstairs. Eat-in Kitchen with Soaring Ceilings is open to Family Room and boasts Granite and Quartz countertops, large Island with Breakfast Bar, Stainless Steel Appliances, Pantry and Hardwood floors. Large 2 story Family Room with Fireplace and Hardwood floors. Dining Room nicely trimmed with simulated wood paneling and crown molding. Living Room with hardwood floors could also serve as an office. First Floor Master Bedroom Suite with hardwoods, cathedral ceiling, walk-in closet, and attached full bath with granite tops, double sinks, and tile surround shower. Upstairs 2nd and 3rd Bedroom and additional full bath with granite tops, double sinks, and jetted tub. Finished Basement with massive cedar closet. 4 Season Screen porch perfect to enjoy the backyard setting. Gorgeous grounds on a perfectly level lot. Bluestone patio and back porch include trex decking, outdoor kitchen, fire pit, built-in kitchen, and salt water spa. Split rail fence. Enjoy your own at home getaway oasis! Large Barn for additional 2 car storage to complement 2 car attached garage. Barn also has ample loft space for storage or possible finished space. Central Air and generator. Roof replaced a few years ago. This home is triple mint!

3 Beds ⋅ 3 Baths ⋅ 24106628 MLS

3184sqft Colonial set on 1.42 acre cul-de-sac rd. lot with Barn with loft, Main level Master Bedroom Suite, Soaring ceilings in Open Floorplan, and outdoor patio paradise. Absolutely Tranquil setting! This home is setup for Main Level living with additional bedrooms upstairs. Eat-in Kitchen with Soaring Ceilings is open to Family Room and boasts Granite and Quartz countertops, large Island with Breakfast Bar, Stainless Steel Appliances, Pantry and Hardwood floors. Large 2 story Family Room with Fireplace and Hardwood floors. Dining Room nicely trimmed with simulated wood paneling and crown molding. Living Room with hardwood floors could also serve as an office. First Floor Master Bedroom Suite with hardwoods, cathedral ceiling, walk-in closet, and attached full bath with granite tops, double sinks, and tile surround shower. Upstairs 2nd and 3rd Bedroom and additional full bath with granite tops, double sinks, and jetted tub. Finished Basement with massive cedar closet. 4 Season Screen porch perfect to enjoy the backyard setting. Gorgeous grounds on a perfectly level lot. Bluestone patio and back porch include trex decking, outdoor kitchen, fire pit, built-in kitchen, and salt water spa. Split rail fence. Enjoy your own at home getaway oasis! Large Barn for additional 2 car storage to complement 2 car attached garage. Barn also has ample loft space for storage or possible finished space. Central Air and generator. Roof replaced a few years ago. This home is triple mint!

5 Blueberry Ln, Woodbury

$1,075,000

This 4,632 square-foot home sits on 20.97 acres offering complete privacy and featuring woods, waterfalls, and walking trails. The home, affectionately known as "The Lodge" centers around a stunning fieldstone fireplace that soars through the dramatic cathedral ceiling in the living room, which divides the three main bedrooms (all en suite!). Gleaming hardwood floors and ceilings throughout and Vermont barnboard walls in the elegant dining room elevate the home. The primary bedroom features a full wall of glass doors that open to a private deck and faces the woods. The enormous space lends itself to unlimited possibilities, from use as-is to the creation of new spaces within the oversized primary bedroom footprint. The primary bath features double sinks, beautiful tile floors, a shower stall, and a large, deep soaking tub. The two additional main-floor bedrooms are oversized and en suite, and have individual access to the wrap-around deck. The upper level consists of a balcony with oversized attic access at each end which could accommodate another bath. In between are two additional rooms. Currently used as home offices, they can also be bedrooms, and are connected by a library passway, hidden panic room, and closet.

3 Beds ⋅ 4 Baths ⋅ 24098935 MLS

This 4,632 square-foot home sits on 20.97 acres offering complete privacy and featuring woods, waterfalls, and walking trails. The home, affectionately known as "The Lodge" centers around a stunning fieldstone fireplace that soars through the dramatic cathedral ceiling in the living room, which divides the three main bedrooms (all en suite!). Gleaming hardwood floors and ceilings throughout and Vermont barnboard walls in the elegant dining room elevate the home. The primary bedroom features a full wall of glass doors that open to a private deck and faces the woods. The enormous space lends itself to unlimited possibilities, from use as-is to the creation of new spaces within the oversized primary bedroom footprint. The primary bath features double sinks, beautiful tile floors, a shower stall, and a large, deep soaking tub. The two additional main-floor bedrooms are oversized and en suite, and have individual access to the wrap-around deck. The upper level consists of a balcony with oversized attic access at each end which could accommodate another bath. In between are two additional rooms. Currently used as home offices, they can also be bedrooms, and are connected by a library passway, hidden panic room, and closet.

220 Church Hill Rd, Woodbury

$1,069,900

Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning remodeled eat-in kitchen, complete with a large center island and all the features expected in a gourmet kitchen. The kitchen opens seamlessly to a generous family room with fireplace, coffered ceiling, and access to the rear level deck, creating a wonderful flow for everyday living and entertaining. The main level also includes a private office, formal living room, and formal dining room, all enhanced by hardwood floors and moldings. Upstairs, the luxurious primary suite features a dressing room or office, two walk-in closets, a soaking tub, and a custom tiled shower. Three additional bedrooms complete the upper level, including two with en-suite baths and one with an open stairway leading to a third floor sleeping area.

4 Beds ⋅ 4 Baths ⋅ 24177448 MLS

Exceptional Colonial in one of Woodbury's finest developments, beautifully set among similar distinguished homes at the end of Silver Brook Lane. Thoughtfully updated over the past five years with high-quality materials and careful attention to detail, this 4,000+ square foot residence offers an ideal blend of elegance, comfort, and modern convenience. The heart of the home is the stunning remodeled eat-in kitchen, complete with a large center island and all the features expected in a gourmet kitchen. The kitchen opens seamlessly to a generous family room with fireplace, coffered ceiling, and access to the rear level deck, creating a wonderful flow for everyday living and entertaining. The main level also includes a private office, formal living room, and formal dining room, all enhanced by hardwood floors and moldings. Upstairs, the luxurious primary suite features a dressing room or office, two walk-in closets, a soaking tub, and a custom tiled shower. Three additional bedrooms complete the upper level, including two with en-suite baths and one with an open stairway leading to a third floor sleeping area.

61 Silver Brook Ln, Woodbury

$1,060,000

The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in the heart of Woodbury, CT, just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom cherry vanity, while modern updates enhance the other baths with style & practicality. The 6.42-acre property invites outdoor enjoyment with a flat yard, tranquil pond, apple trees & fenced-in garden. A restored English barn with a loft & insulated garage with a propane heater, floor drains & updated electrical systems provide space for projects, storage, or entertaining. Behind its historic charm lies modern reliability: new HVAC, plumbing & electrical systems, a high-efficiency propane hot water heater, whole-house generator, extensive insulation & climate-controlled attics. Perfect as a retreat or year-round sanctuary, this property is a rare opportunity to own a piece of hi

4 Beds ⋅ 4 Baths ⋅ 24050150 MLS

The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in the heart of Woodbury, CT, just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom cherry vanity, while modern updates enhance the other baths with style & practicality. The 6.42-acre property invites outdoor enjoyment with a flat yard, tranquil pond, apple trees & fenced-in garden. A restored English barn with a loft & insulated garage with a propane heater, floor drains & updated electrical systems provide space for projects, storage, or entertaining. Behind its historic charm lies modern reliability: new HVAC, plumbing & electrical systems, a high-efficiency propane hot water heater, whole-house generator, extensive insulation & climate-controlled attics. Perfect as a retreat or year-round sanctuary, this property is a rare opportunity to own a piece of hi

382 Weekeepeemee Rd, Woodbury

$1,050,000

A stunning 4-bedroom, 2.5-bathroom colonial nestled on a private 2-acre lot, set back along a winding newly decorative stone driveway in an estate-like setting. This beautifully designed home boasts an open floor plan with high ceilings-9+ feet in most rooms and soaring to 10.5 feet in the living room-refined finishes, and luxurious upgrades throughout. The gourmet kitchen features granite countertops, an oversized island, a full pantry, and top-of-the-line appliances, seamlessly flowing into the expansive great room and out to a brick paver patio-perfect for entertaining. The formal dining room is generously sized with two sets of French doors, while a 6+ foot double French door leads to the backyard oasis with a 6-person hot tub and professionally manicured landscaping that offers beauty with minimal upkeep. Upstairs, the private primary suite includes a spa-like bathroom with dual stone vanities, a jetted tub, a glass shower, and an enormous walk-in closet. Three additional bedrooms with ample closet space, a full bath, and a dedicated laundry room complete the upper level. The fourth bedroom can serve as a recreation room and has a separate entrance from the lower level. Additional highlights include a home office, refinished hardwood floors, newly painted interiors, a new fireplace, new driveway, and 3-car garage. This home offers privacy, convenience, and modern comfort just minutes from Hollow Park, New Morning market, and Main Street restaurants!

4 Beds ⋅ 3 Baths ⋅ 24087630 MLS

A stunning 4-bedroom, 2.5-bathroom colonial nestled on a private 2-acre lot, set back along a winding newly decorative stone driveway in an estate-like setting. This beautifully designed home boasts an open floor plan with high ceilings-9+ feet in most rooms and soaring to 10.5 feet in the living room-refined finishes, and luxurious upgrades throughout. The gourmet kitchen features granite countertops, an oversized island, a full pantry, and top-of-the-line appliances, seamlessly flowing into the expansive great room and out to a brick paver patio-perfect for entertaining. The formal dining room is generously sized with two sets of French doors, while a 6+ foot double French door leads to the backyard oasis with a 6-person hot tub and professionally manicured landscaping that offers beauty with minimal upkeep. Upstairs, the private primary suite includes a spa-like bathroom with dual stone vanities, a jetted tub, a glass shower, and an enormous walk-in closet. Three additional bedrooms with ample closet space, a full bath, and a dedicated laundry room complete the upper level. The fourth bedroom can serve as a recreation room and has a separate entrance from the lower level. Additional highlights include a home office, refinished hardwood floors, newly painted interiors, a new fireplace, new driveway, and 3-car garage. This home offers privacy, convenience, and modern comfort just minutes from Hollow Park, New Morning market, and Main Street restaurants!

17 Transylvania Rd, Woodbury

$1,050,000

Welcome to the Owl Ridge neighborhood of Woodbury, this newly renovated 4-bed, 5-bath home is in pristine condition and features a harmonious blend of comfort and space. The heart of the home is the newly renovated kitchen, with natural quartzite countertops, refinished hardwood floors and new stainless steel appliances. The open concept design seamlessly connects the eat-in kitchen to the expansive family room, where a cozy fireplace and cathedral ceilings invites you to relax and unwind. Entertain in the formal living and dining room plus a roomy great room as a separate play room, music or media room. Work from home in the dedicated office with its own half bath. The sunroom works as a play room or art studio complete with sink to wash out your brushes. Upstairs the primary bedroom suite is a private retreat, complete with a sitting room, where you can escape for moments of tranquility. Three additional bedrooms, one ensuite and two more bathrooms complete the second floor. Outside, the property's vast deck is perfect for outdoor living and entertaining.

4 Beds ⋅ 5 Baths ⋅ 24044196 MLS

Welcome to the Owl Ridge neighborhood of Woodbury, this newly renovated 4-bed, 5-bath home is in pristine condition and features a harmonious blend of comfort and space. The heart of the home is the newly renovated kitchen, with natural quartzite countertops, refinished hardwood floors and new stainless steel appliances. The open concept design seamlessly connects the eat-in kitchen to the expansive family room, where a cozy fireplace and cathedral ceilings invites you to relax and unwind. Entertain in the formal living and dining room plus a roomy great room as a separate play room, music or media room. Work from home in the dedicated office with its own half bath. The sunroom works as a play room or art studio complete with sink to wash out your brushes. Upstairs the primary bedroom suite is a private retreat, complete with a sitting room, where you can escape for moments of tranquility. Three additional bedrooms, one ensuite and two more bathrooms complete the second floor. Outside, the property's vast deck is perfect for outdoor living and entertaining.

6 Owl Ridge Rd, Woodbury

$975,000

Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options for multigenerational living or working from home. The heart of the home is a generously sized kitchen with a sunny eat-in area, center sitting island, and easy access to a formal dining room-ideal for hosting gatherings and family meals.The open floor plan flows effortlessly into the vaulted living room with fireplace, creating a warm, inviting space perfect for everyday living. A large laundry room and attached garage add to the home's convenience. Upstairs, you'll find additional bedrooms, a dedicated home office, and a playroom-providing space for everyone to work, relax, and play.Step outside to your own private resort-style retreat, complete with a sparkling in-ground pool, fully equipped outdoor kitchen, and lower-level pool dressing area. Whether you're entertaining or simply unwinding, the outdoor space is a true showstopper.Enjoy year-round comfort with high-efficiency baseboard heating and central air conditioning. Finished with beautiful moldings, hardwood floors throughout, and set in a serene nature-filled setting just minutes to town-this home truly has it all.

5 Beds ⋅ 3 Baths ⋅ 24115189 MLS

Private 3-Acre Retreat! Tucked away on a peaceful and private 3-acre lot, this beautifully maintained 5-bedroom, 3-bath home offers the perfect blend of luxury, space, and functionality-with over 3,450 sq ft of living space designed for comfort and entertaining.The main level features a flexible layout with either a first-floor primary suite and office or two spacious bedrooms, offering options for multigenerational living or working from home. The heart of the home is a generously sized kitchen with a sunny eat-in area, center sitting island, and easy access to a formal dining room-ideal for hosting gatherings and family meals.The open floor plan flows effortlessly into the vaulted living room with fireplace, creating a warm, inviting space perfect for everyday living. A large laundry room and attached garage add to the home's convenience. Upstairs, you'll find additional bedrooms, a dedicated home office, and a playroom-providing space for everyone to work, relax, and play.Step outside to your own private resort-style retreat, complete with a sparkling in-ground pool, fully equipped outdoor kitchen, and lower-level pool dressing area. Whether you're entertaining or simply unwinding, the outdoor space is a true showstopper.Enjoy year-round comfort with high-efficiency baseboard heating and central air conditioning. Finished with beautiful moldings, hardwood floors throughout, and set in a serene nature-filled setting just minutes to town-this home truly has it all.

364 Hoop Pole Hill Rd, Woodbury

$975,000

A rare find, this ca 1860 cape sits on 2+ acres just outside of town and includes a cottage, in-ground pool, pool cabana, workshop, and potting shed. The home itself is the perfect size with three bedrooms and two full and one-half baths. The living room is highlighted by built-ins and exposed beams. The dining room with exposed beams has corner cupboard and French door to a stone terrace perfect for al fresco dining or a morning coffee. A fireplace adorns the eat-in kitchen and there is a 5-burner gas stove top, Bosch double oven and Subzero refrigerator. The primary bedroom is conveniently located on the main level and has a vaulted ceiling, spacious full bath and French door to rear patio. Upstairs you'll find the two other bedrooms, a full bath and foyer perfect for a reading nook or office area. The main level also includes a foyer, mudroom and laundry room. Beautiful hardwood floors throughout the home. The many updates include a generator (services house & cottage) and smart systems for thermostat and security. The grounds are lovely with mature perennial gardens, multiple patios, stonewalls and walkways, and a fenced in raised bed vegetable garden. There is a detached two bay garage and a detached 1 bay stone garage. The lovely 768 sq ft cottage is set away from the main residence & has kitchen, living/dining combo, two bedrooms, full bath on main level and lower level with half bath and laundry room. List of upgrades/updates available.

3 Beds ⋅ 3 Baths ⋅ 24037167 MLS

A rare find, this ca 1860 cape sits on 2+ acres just outside of town and includes a cottage, in-ground pool, pool cabana, workshop, and potting shed. The home itself is the perfect size with three bedrooms and two full and one-half baths. The living room is highlighted by built-ins and exposed beams. The dining room with exposed beams has corner cupboard and French door to a stone terrace perfect for al fresco dining or a morning coffee. A fireplace adorns the eat-in kitchen and there is a 5-burner gas stove top, Bosch double oven and Subzero refrigerator. The primary bedroom is conveniently located on the main level and has a vaulted ceiling, spacious full bath and French door to rear patio. Upstairs you'll find the two other bedrooms, a full bath and foyer perfect for a reading nook or office area. The main level also includes a foyer, mudroom and laundry room. Beautiful hardwood floors throughout the home. The many updates include a generator (services house & cottage) and smart systems for thermostat and security. The grounds are lovely with mature perennial gardens, multiple patios, stonewalls and walkways, and a fenced in raised bed vegetable garden. There is a detached two bay garage and a detached 1 bay stone garage. The lovely 768 sq ft cottage is set away from the main residence & has kitchen, living/dining combo, two bedrooms, full bath on main level and lower level with half bath and laundry room. List of upgrades/updates available.

151 Flanders Rd, Woodbury

$970,000

Live your best life in Woodbury, CT, where charm, history, and natural beauty intertwine! The "Antiques Capital of CT", with a picturesque Main Street, historic homes, festivals, and scenic preserves. Imagine living in the heart of this idyllic setting! This 2005 home, on 4.5 acres, is meant for life, living, and entertaining. Upstairs, you'll find 4 generously sized bedrooms and 3 well-appointed bathrooms; 2 of which are ensuite, along with a convenient laundry area. On the main floor, there are living, dining, and family rooms, a half-bath, study, a dinette, and kitchen. There is a large attic and a bright walkout full basement which is partially finished with all walls and future rooms fully framed. Step outside and be amazed by the 40' in-ground heated pool, a spectacular custom-built pavilion and pool house with living-space, loft, a half bath, and a glorious outdoor shower. The star of the show is the full outdoor Viking kitchen & bar. Providing unforgettable experiences for gatherings of any size; Simple dinners or awesome larger celebrations! The expansive grounds offer the perfect mix of level terrain and picturesque hills, for outdoor fun in every season. Swimming, ATV, ball games, sledding and much more! 25 Curtiss Meadows is a camp-like getaway for close ones and friends and an immensely profound and treasured home for its residents. This gem is an absolute must-see. Don't miss the opportunity, schedule your private showing today and begin your next chapter

4 Beds ⋅ 4 Baths ⋅ 24107125 MLS

Live your best life in Woodbury, CT, where charm, history, and natural beauty intertwine! The "Antiques Capital of CT", with a picturesque Main Street, historic homes, festivals, and scenic preserves. Imagine living in the heart of this idyllic setting! This 2005 home, on 4.5 acres, is meant for life, living, and entertaining. Upstairs, you'll find 4 generously sized bedrooms and 3 well-appointed bathrooms; 2 of which are ensuite, along with a convenient laundry area. On the main floor, there are living, dining, and family rooms, a half-bath, study, a dinette, and kitchen. There is a large attic and a bright walkout full basement which is partially finished with all walls and future rooms fully framed. Step outside and be amazed by the 40' in-ground heated pool, a spectacular custom-built pavilion and pool house with living-space, loft, a half bath, and a glorious outdoor shower. The star of the show is the full outdoor Viking kitchen & bar. Providing unforgettable experiences for gatherings of any size; Simple dinners or awesome larger celebrations! The expansive grounds offer the perfect mix of level terrain and picturesque hills, for outdoor fun in every season. Swimming, ATV, ball games, sledding and much more! 25 Curtiss Meadows is a camp-like getaway for close ones and friends and an immensely profound and treasured home for its residents. This gem is an absolute must-see. Don't miss the opportunity, schedule your private showing today and begin your next chapter

25 Curtiss Mdws, Woodbury

$952,000

Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas cooktop, walk-in pantry & dining area, overlooks the pool & patio. Adjacent to the kitchen is a sitting room & spacious family room featuring a fireplace & built-in bookcase. A generous 20x35 recreation room further enhances the home's entertainment options with a custom bar, vaulted ceiling, full bath & two sets of sliding doors that open to the pool, spa & patio area, creating a perfect indoor-outdoor experience. The upper level boasts a primary suite with a spacious bath & walk-in closet along with two additional bedrooms connected by a Jack & Jill bath. This floor also includes a craft/yoga room & laundry room. On the 3rd floor, a private fourth bedroom with a full bath provides an ideal space for nanny quarters or guests. The lower level offers 715 square feet of flexible finished space, perfect for a workout area with room for a golf simulator & includes ample storage & access to the 3-car garage. Outside, the grounds are complete with a gunite pool, spa, fire pit, stone wall & a fenced area, creating a tranquil oasis for relaxation & entertainment-all just minutes from town!

4 Beds ⋅ 5 Baths ⋅ 24059188 MLS

Tucked away on a sought-after cul-de-sac, this open-layout home is crafted for exceptional entertaining. The light-filled, two-story foyer is framed by two sets of French doors: one opening to an office & the other leading to a living room that flows seamlessly into the dining room-an ideal setup for holiday gatherings. The custom kitchen, equipped with granite countertops, a center island, gas cooktop, walk-in pantry & dining area, overlooks the pool & patio. Adjacent to the kitchen is a sitting room & spacious family room featuring a fireplace & built-in bookcase. A generous 20x35 recreation room further enhances the home's entertainment options with a custom bar, vaulted ceiling, full bath & two sets of sliding doors that open to the pool, spa & patio area, creating a perfect indoor-outdoor experience. The upper level boasts a primary suite with a spacious bath & walk-in closet along with two additional bedrooms connected by a Jack & Jill bath. This floor also includes a craft/yoga room & laundry room. On the 3rd floor, a private fourth bedroom with a full bath provides an ideal space for nanny quarters or guests. The lower level offers 715 square feet of flexible finished space, perfect for a workout area with room for a golf simulator & includes ample storage & access to the 3-car garage. Outside, the grounds are complete with a gunite pool, spa, fire pit, stone wall & a fenced area, creating a tranquil oasis for relaxation & entertainment-all just minutes from town!

5 Bear Run, Woodbury

$950,000

Immerse yourself in the peace and tranquility of this historic 1870's saltbox. The thoughtfully designed home boasts wide plank floors, horizontal paneling, barn sided walls, built-ins and thermopane windows. Cozy into the combo living dining room with its custom sisal rug, a perfect space for entertaining. The refreshed kitchen connects to the den with large picture windows overlooking the hemlock bordered pea stone terrace. A tidy laundry room, full bath and office overlooking the front yard is perfect for working from home. The second-floor houses two bedrooms, marble and tile full bath and sitting/tv room with additional built-ins for storage. The spacious full floor primary suite nests on the third floor with a vaulted ceiling, walk-in closet, sitting area and marble lined full bathroom with step-in shower. The rescaled and squared stone walls border and transform the landscape. Unwind by the mesmerizing waterfall cascading onto your private two-acre oasis. From the waterfall sitting area walk amongst specimen tree's, flowering shrubs and bushes that envelope and highlight the property. The property sites across from the Nonnewaug River where the serenity of the natural waterfall will ease you with the sounds of nature. 90 from NYC and minutes from the shops and restaurants of historical Woodbury. This historic charmer offers modern updates and a tranquil escape you won't want to miss!

3 Beds ⋅ 3 Baths ⋅ 24015950 MLS

Immerse yourself in the peace and tranquility of this historic 1870's saltbox. The thoughtfully designed home boasts wide plank floors, horizontal paneling, barn sided walls, built-ins and thermopane windows. Cozy into the combo living dining room with its custom sisal rug, a perfect space for entertaining. The refreshed kitchen connects to the den with large picture windows overlooking the hemlock bordered pea stone terrace. A tidy laundry room, full bath and office overlooking the front yard is perfect for working from home. The second-floor houses two bedrooms, marble and tile full bath and sitting/tv room with additional built-ins for storage. The spacious full floor primary suite nests on the third floor with a vaulted ceiling, walk-in closet, sitting area and marble lined full bathroom with step-in shower. The rescaled and squared stone walls border and transform the landscape. Unwind by the mesmerizing waterfall cascading onto your private two-acre oasis. From the waterfall sitting area walk amongst specimen tree's, flowering shrubs and bushes that envelope and highlight the property. The property sites across from the Nonnewaug River where the serenity of the natural waterfall will ease you with the sounds of nature. 90 from NYC and minutes from the shops and restaurants of historical Woodbury. This historic charmer offers modern updates and a tranquil escape you won't want to miss!

6 Mill Rd, Woodbury

$940,000

Serenity is at the end of the cul de sac in this roomy and charming colonial. Home features 5 bedrooms with hardwood floors. Primary bedroom has 2 walk in closets, a large bathroom with jacuzzi tub, double sinks and walk in shower. Laundry/office area is off the primary bedroom. 3 more large bedrooms in the upper level all have walk in closets. Main bathroom has double sinks and granite counters. Upper level also features a reading/lounge area with a Juliette balcony. Kitchen offers a large island with oven on each side, a butlers pantry and a breakfast nook. Propane cook top, microwave, refrigerator and dishwasher included. Off the kitchen is a warm and spacious sunroom with radiant floors. Family room offers a fireplace with wood stove insert and built in bookcases. Formal living room has plaster ceiling moldings and candle chandeliers. Dining room has plenty of room for family get togethers. Separate entrance leads to a bedroom/office with full bath and washer/dryer on the main level. Lower level features two large rooms which can used for large family get togethers and a kitchenette with sink and refrigerator. Full bath with shower is on lower level. Sliders to large patio lead to the pool area and rotisserie. Bonus wine cellar in lower level. The salt water pool is 40x20. A gazebo with fish pond is located nearby. Large 2.33 lot has fruit trees, perennials, sprinkler system, and large open areas for outdoor enjoyment. Heated outdoor front walkway. Handicap access.

5 Beds ⋅ 4 Baths ⋅ 170557304 MLS

Serenity is at the end of the cul de sac in this roomy and charming colonial. Home features 5 bedrooms with hardwood floors. Primary bedroom has 2 walk in closets, a large bathroom with jacuzzi tub, double sinks and walk in shower. Laundry/office area is off the primary bedroom. 3 more large bedrooms in the upper level all have walk in closets. Main bathroom has double sinks and granite counters. Upper level also features a reading/lounge area with a Juliette balcony. Kitchen offers a large island with oven on each side, a butlers pantry and a breakfast nook. Propane cook top, microwave, refrigerator and dishwasher included. Off the kitchen is a warm and spacious sunroom with radiant floors. Family room offers a fireplace with wood stove insert and built in bookcases. Formal living room has plaster ceiling moldings and candle chandeliers. Dining room has plenty of room for family get togethers. Separate entrance leads to a bedroom/office with full bath and washer/dryer on the main level. Lower level features two large rooms which can used for large family get togethers and a kitchenette with sink and refrigerator. Full bath with shower is on lower level. Sliders to large patio lead to the pool area and rotisserie. Bonus wine cellar in lower level. The salt water pool is 40x20. A gazebo with fish pond is located nearby. Large 2.33 lot has fruit trees, perennials, sprinkler system, and large open areas for outdoor enjoyment. Heated outdoor front walkway. Handicap access.

89 Northgate Rd, Woodbury

$925,000

This exceptional residence welcomes you with a dramatic two-story entry and is designed for both refined entertaining and comfortable everyday living, just minutes from town. There is a formal living and dining room with rich hardwood flooring, creating a sophisticated setting for gatherings. The heart of the home is a beautifully appointed chef's kitchen featuring granite countertops, a breakfast bar, and KitchenAid and Thermador appliances. The sun-filled breakfast nook flows effortlessly into the inviting family room, where a striking stone fireplace and expansive bay window frame picturesque views of the property. A set of sliders open to a large composite deck for summer enjoyment. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. This luxurious space features a spa-inspired bath, two walk-in closets, and an elegant sitting room with fireplace and built-ins, along with a private office or dressing room. Three additional en-suite bedrooms-including one currently used as a gym-offer comfort and privacy for family and guests. The partially finished walk-out lower level is filled with natural light, offering impressive 9+ foot ceilings and exceptional versatility. Anchored by a beautiful stone fireplace, the space includes two additional finished rooms and a full bath-ideal for recreation, guest accommodations, or extended living. There is a relaxing patio, peach trees, pear trees and raspberries. A must see!

4 Beds ⋅ 6 Baths ⋅ 24158582 MLS

This exceptional residence welcomes you with a dramatic two-story entry and is designed for both refined entertaining and comfortable everyday living, just minutes from town. There is a formal living and dining room with rich hardwood flooring, creating a sophisticated setting for gatherings. The heart of the home is a beautifully appointed chef's kitchen featuring granite countertops, a breakfast bar, and KitchenAid and Thermador appliances. The sun-filled breakfast nook flows effortlessly into the inviting family room, where a striking stone fireplace and expansive bay window frame picturesque views of the property. A set of sliders open to a large composite deck for summer enjoyment. The second floor is highlighted by an extraordinary primary suite designed as a private retreat. This luxurious space features a spa-inspired bath, two walk-in closets, and an elegant sitting room with fireplace and built-ins, along with a private office or dressing room. Three additional en-suite bedrooms-including one currently used as a gym-offer comfort and privacy for family and guests. The partially finished walk-out lower level is filled with natural light, offering impressive 9+ foot ceilings and exceptional versatility. Anchored by a beautiful stone fireplace, the space includes two additional finished rooms and a full bath-ideal for recreation, guest accommodations, or extended living. There is a relaxing patio, peach trees, pear trees and raspberries. A must see!

35 Coach Light Dr, Woodbury

Dave Jones Realty llc

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