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$925,000
4 Beds ⋅ 4 Baths ⋅ 24076275 MLS
Stunning! Dramatically open, spacious, modern colonial offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 4 spacious bedrooms, 3.5 bathrooms, and a generously sized finished "Wow" room with its own additional bedroom providing endless possibilities for a guest suite, home office, media room or recreation space. Situated on over two acres surrounded by peaceful woodlands, the home is an entertainer's dream, featuring an open-concept kitchen, dining, and living area with a warm and inviting fireplace. Step outside to discover a beautiful outdoor oasis with fire pit creating the perfect setting for relaxation and gatherings. Conveniently located near top private schools like Taft and Westover, as well as local farms, restaurants, boutique shopping, and outdoor recreation. This exceptional home offers the best of Litchfield County living with convenient access to the charming towns of Litchfield, Washington, and Roxbury. Less than two hours from New York City, this stunning move-in-ready home presents a rare opportunity to own a serene yet accessible retreat in one of Connecticut's most desirable areas.

102 Quanopaug Trl, Woodbury
$922,000
4 Beds ⋅ 3 Baths ⋅ 24145387 MLS
Nestled within an established enclave of Woodbury-a quintessential New England town-this 2001 four-bedroom Colonial offers a refined blend of understated, classic architecture, and modern comfort. Ideally located just five minutes from Main Street, the home is privately sited at the end of a quiet cul-de-sac, bordered by tranquil woodlands. The interior showcases richly layered trim details, including deep crown moldings, wainscoting, and substantial baseboards in the formal spaces, creating an elegant and tailored aesthetic. The home thoughtfully balances formal entertaining areas with an open-concept layout. The gracious foyer, flanked by a formal Dining Room and a Living Room featuring custom woodworking, leads into the expansive, sun-filled Kitchen and Family Room. Designed for entertaining, the formal Dining Room features a beautiful custom built-in and a charming bay window and connects to the Kitchen via a functional hallway ideal for use as a butler's pantry or bar. This hallway provides access to a combined mudroom/Laundry Room and Half Bath. The Kitchen and Family Room form the heart of the home, featuring a cozy gas fireplace, a six-burner Wolf range, and direct access to a private Deck and stone terrace-perfect for outdoor dining and summer gatherings.

52 Steeple View Ln, Woodbury
$916,000
4 Beds ⋅ 4 Baths ⋅ 24036277 MLS
Nearly 3500 square feet, completely updated home combines top of the line luxury w green efficiency, unsurpassed privacy and seasonal views, all just five minutes from the charming town center. 4 BR, 3.5 bath house is built like a tank and has benefited from a series of tasteful, high-end upgrades, including white oak flooring throughout, and expanded 36' deck, updated kitchen w bespoke breakfast room banquette. Fully gut, renovated bathrooms in 2023 w two Carrera marble en-suites. Stunning primary bath off huge suite w three walk in closets. Victoria and Albert 75" volcanic limestone soaking tub, large bespoke shower, basketweave marble floors, niche and double vanity. Piece-de-resistance is the 22'x20' vaulted great room with double height fireplace, French doors and large bay window w seating. Green upgrades include Bosch heat pumps in 2023 save thousands yearly. Generator. Three car garage, Buderus furnace, 8' ceilings in unfinished bsmt. Borders 6.3 acres of Flanders Nature Preserve. The towns Trolley Bed Preserve, hiking, & biking trails are just minutes away. Enjoy the open air with professional landscaping and five outdoor seating areas, including a brick patio w built-in firepit. Sunsets are unmatched with seasonal views across the Pomperaug Valley. Easy access to I-84, 90 minutes to NYC, and 35 minutes minutes to Metro-North at Southeast.

41 Curtiss Mdws, Woodbury
$910,000
4 Beds ⋅ 4 Baths ⋅ 170626582 MLS
Nestled in a serene, private location yet close to Woodbury's excellent dining & shopping is this four bedroom Colonial with an unparalleled blend of comfort and convenience. It’s an inviting atmosphere of spacious rooms flooded by natural light with 4200 square feet of living space. The main level Living Room, Great Room and Sunroom are complemented by a combination of three fireplaces, vaulted ceilings and Palladian windows with a Formal Dining Room for holiday gatherings. The Eat-in Kitchen at the heart of the home features granite countertops, a dual fuel gas range, Sub-zero refrigerator, breakfast bar & dining area with sliders leading to a deck overlooking the heated salt-water pool--an oasis for relaxation and entertainment. In the Primary Bedroom Suite on the upper level you’ll find a luxurious marble bath with dual vanities, a large walk-in glass shower, dressing area & heated floor. There’s an additional En-suite Bedroom for guests (or that lucky teenager), two more comfortably sized Bedrooms & a third Full Bath. The partially finished walkout lower level extends the living space to a stone patio and pergola at poolside. The level, private interior lot on a cul-de-sac street is just a three minute drive from the town center. A whole-house generator with automatic transfer switch provides added peace of mind. The property offers the perfect blend of tranquility and accessibility, an ideal retreat for discerning buyers seeking the quintessential New England lifestyle.

9 Steeple View Ln, Woodbury
$905,000
3 Beds ⋅ 3 Baths ⋅ 24057609 MLS
Experience the epitome of architectural artistry with this contemporary home, a serene sanctuary that celebrates the fusion of nature and modern design. Perched on 3.4 acres and hidden amongst the trees, this property presents framed views of nature and mossy stone outcroppings. High-end appliances including Gaggenau and JennAir in the kitchen and hi-tech amenities throughout cater to a lifestyle of modern convenience. The primary suite exemplifies contemporary luxury with a pair of wall hung sinks, stall shower, separate w/c and a full swath of built-in closets. The upper bedroom provides an ensuite full bath and private entrance, while the lower bedroom shares its full bath with the great room. Audiophiles will appreciate the integrated surround sound in the great room with easy access to the bar for a chilled beverage or glass of wine. The artist loft/den with its own lookout creates a creative space for inspiration or work from home convenience. Step outside to the expansive stone patios with built in grill and pizza oven, a private deck, all designed for seamless indoor-outdoor living. The wine cellar invites connoisseurs to indulge in their collection, while the whole house generator ensures uninterrupted comfort. This stunning award winning home is more than a residence; it's a statement of living art, offering a tranquil escape and the perfect blend of form, function, and efficiency. 90 from NYC and minutes from the shops and restaurants of historic Woodbury.

17 Birchwood Ln, Woodbury
$900,000
3 Beds ⋅ 3 Baths ⋅ 24008027 MLS
Every now and then a perfect home comes on the market where the homeowner has maintained and perfected items throughout their occupancy. Be certain to look at the attached list of the Home Amenities! Located in a beautiful subdivision just minutes to the town center this home has an exceptional kitchen with granite, Wolf cooktop, double Wolf electric convection ovens, subzero refrigerator and freezer and so much more. The primary bedroom with luxurious bath is on the main floor with two additional bedrooms on the second. The outstanding floor plan is generous with size and functionality and leads you to covered and open Trek decks. This cul-de-sac has a fifteen acre home owner association owned wooded conservation area. Woodbury was featured in the New York Times Living In section calling it Peace, Quaint Beauty and a Sense of History and again Reader's Digest named Woodbury Best Small Town in Connecticut with its hiking trails, parks, Orenaug Tower and park overlooking the town, sidewalks, shopping, outdoor summer concerts, indoor concerts, community theater, community center, Flanders Nature Center and wonderful library with artists and speakers. From our sidewalks you can walk to the schools, stores, library, coffee shops renown restaurants and hiking trails. Located only 1/2 hr to train station, 10 minutes to I-84, 1 1/2 hr by car to NYC and 1 hr. to an airport. Available for August 31.

40 Stonefield Rd, Woodbury
$897,000
3 Beds ⋅ 3 Baths ⋅ 24096111 MLS
Stunning reproduction of a mid-1700s New England Center-Chimney Cape, masterfully built in 2015 and set on 3.3+/- acres. This 3-bed, 3-bath home blends timeless craftsmanship-12-over-12 windows, wide plank circle-sawn floors, custom trim and paneling-with modern luxuries including smart home tech, soapstone counters, and a showpiece kitchen hearth. Enjoy nearly 2,900 sq ft of living space, including a finished bonus room over the oversized 4-bay garage, perfect for a studio or home office. Outdoor living features a bluestone patio, firepit, and fenced gardens. Close to Woodbury center for fine dining and shopping and convenient to Roxbury and Washington. Under 2hrs to NYC.

332 Good Hill Rd, Woodbury
$895,000
4 Beds ⋅ 4 Baths ⋅ 24075051 MLS
Located in the heart of Woodbury, the antiques capital of Connecticut, with convenient access to the charming towns of Litchfield, Washington, and Roxbury, this newly built modern farmhouse offers a perfect balance of comfort and elegance. Thoughtfully designed with quality craftsmanship and energy-efficient features, this inviting retreat boasts 3 spacious bedrooms, 3.5 bathrooms, and a generously sized finished bonus room with its own full bath, providing endless possibilities for a guest suite, home office, or recreation space. Situated on approximately three acres surrounded by peaceful woodlands, the home is an entertainer's dream, featuring an open-concept kitchen, dining, and living area with a warm and inviting gas fireplace. Step outside to discover a beautifully designed outdoor oasis, complete with a pool, lush gardens, and a charming pool house, creating the perfect setting for relaxation and gatherings. Conveniently located near top private schools like Taft and Westover, as well as local farms, restaurants, boutique shopping, and outdoor recreation, this home offers the best of Litchfield County living. Just a short drive to Quassy Amusement Park and less than two hours from New York City, this stunning move-in-ready home presents a rare opportunity to own a serene yet accessible retreat in one of Connecticut's most desirable areas. Owner is broker/agent.

35 Fawn Meadow Ln, Woodbury
$885,000
4 Beds ⋅ 4 Baths ⋅ 24158380 MLS
Welcome to Upper Grassy Hill Living!

557 Upper Grassy Hill, Woodbury
$875,000
5 Beds ⋅ 4 Baths ⋅ 24018837 MLS
Nestled at the intersection of Route 72 and Route 167 in Woodbury, this exceptional home is the perfect blend of modern amenities and unparalleled convenience. Located in close proximity to both the Center of Woodbury and the Southbury Green you'll be moments away from a diverse selection of shops and restaurants. Enjoy the close by natural beauty of Wood Lake, local parks, walking trails, and make the most of the nearby Southbury Dog Park. With easy access to exits 13, 14, and 15 off of I-84, as well as route 8, commuting will never be easier. This property is directly next to the entrance of Janie Pierce Park and backs up to over 30 acres of serene land conservation, guaranteeing exceptional privacy and tranquility for years to come. Upon entering, you'll be greeted by an open floor plan that seamlessly combines elegance and functionality. The inviting kitchen features granite countertops, a breakfast bar, and a new deck just off the kitchen-ideal for entertaining. The main level is adorned with rich hardwood floors, while the upper bedrooms are enhanced with stylish vinyl plank flooring. The grand living room boasts cathedral ceilings and expansive windows extending to the second floor, creating a dramatic and airy atmosphere. Two staircases provide stylish access to the upper level, where you can overlook the main living area below.

447 Transylvania Rd, Woodbury
$865,000
3 Beds ⋅ 4 Baths ⋅ 24063231 MLS
This beautifully renovated Saltbox, completed in 2022, comes fully furnished and ready for immediate move-in. The home features new or updated bathrooms and kitchen, elegant wallpaper accents, cozy rooms, two fireplaces, and abundant natural light. The lower level includes a mudroom with custom built-ins, a new full bath, a recreational room, and access to an oversized two-car garage. On the main level, you'll find an eat-in kitchen with a fireplace and center island, a family room with a beamed vaulted ceiling, a formal dining room, and a formal living room or office with a second fireplace. The upper floor boasts two bedrooms, two full baths, and a luxurious primary suite. Overlooking three acres, this furnished home is just minutes from the town center and Woodbury's fabulous restaurants!

172 Good Hill Rd, Woodbury
$855,900
4 Beds ⋅ 5 Baths ⋅ 170611183 MLS
**** THIS PROPERTY HAS MULTIPLE BIDS / Highest And Best due Date Is 3/18/2024 11:59:00 PM MST*** Custom colonial designed by architect Moisan located at the end of a cul-de-sac on a 57 acre lot. The home has nice views and is bordered by Hesseky Meadow Pond and the Flanders Nature Center. The home has a great floor plan, 3 fireplaces, high ceilings throughout and expansion possibilities for additional sq ft in the walk up attic and basement. The property does need some work and is being sold as is.

105 Old Grassy Hill Rd, Woodbury
$850,000
4 Beds ⋅ 3 Baths ⋅ 24138603 MLS
Tucked away in a private and peaceful setting, this beautifully appointed Colonial offers an exceptional blend of comfort, style and functionality. Hardwood floors and custom millwork are showcased throughout, creating a warm and refined atmosphere. A dramatic two-story foyer welcomes you and is flanked by a first-floor office with transom-topped French doors for privacy. Opposite, a double opening with a transom window leads to the formal dining room, which flows seamlessly into the formal living room-ideal for entertaining. The spacious eat-in kitchen is thoughtfully designed with stainless steel appliances, granite countertops, a center island, and a dining area with sliders leading to a large patio-perfect for effortless indoor-outdoor living and entertaining. The kitchen opens to a generous family room featuring a fireplace and custom built-in bookcases, creating a comfortable and inviting gathering space. A half bath and convenient mudroom complete the main level. Upstairs, the home offers four bedrooms, all with wall-to-wall carpeting, including a spacious primary suite with tray ceiling and a full bath with double vanities, a soaking tub, and a walk-in shower. A dedicated laundry room enhances everyday convenience. The unfinished lower level provides excellent potential for future living space, allowing the next owner to tailor it to their needs. Enjoy a large, level yard ideal for recreation, gardening or gatherings.. Your peaceful retreat awaits!

99 Plumb Brook Rd, Woodbury
$850,000
4 Beds ⋅ 3 Baths ⋅ 24086901 MLS
Welcome to Woodbury! Rebuilt in 1991, this stunning 3,736 sq ft single-family estate sits gracefully on over 11 acres, offering the perfect blend of refined luxury and serene countryside living. Step inside to discover a spacious, light-filled interior designed for both grand entertaining and comfortable everyday living. With four generously sized bedrooms, multiple living areas, and fine architectural details throughout, every corner of this home exudes sophistication. The gourmet kitchen opens to elegant dining and family spaces, while expansive windows frame picturesque views of the surrounding landscape. Outdoors, a built-in pool invites you to relax and entertain in style, with plenty of room to expand your vision - whether it's a garden, horse paddock, additional dwelling or private vineyard. A three-car garage and circular driveway ensure privacy and convenience, all within minutes of Woodbury's charming town center, fine dining, and schools. This is more than a home - it's an estate, a retreat, and a lifestyle.

84 Hurds Hill Rd, Woodbury
$850,000
4 Beds ⋅ 3 Baths ⋅ 24061890 MLS
Welcome to 62 Whittlesey Road, a beautifully maintained Colonial just minutes from Woodbury Center. Set on 2.31 acres of private, level land, this 3,205 sq ft home boasts 4 bedrooms and 2.5 baths, with thoughtfully designed spaces perfect for everyday living and entertaining. The gourmet kitchen, equipped with Viking appliances and granite countertops, island and pantry flow seamlessly into the family room, featuring vaulted ceilings and an impressive stone fireplace. A formal dining room with a tray ceiling, a formal living room, and a first-floor office round out the main level. The upper level features a luxurious primary suite complete with a walk-in closet, double vanity, soaking tub, and separate shower. There are threee additional bedrooms including a spacious room with double closets and a loft, while a convenient second-floor laundry room completes the layout. Step outside to a Trex deck that overlooks the expansive backyard, ideal for entertaining friends and family while enjoying the beauty of nature. The full walkout basement provides endless possibilities for storage, hobbies, or future finishing, and a three-car attached garage rounds out this exceptional property. With its prime location, stunning features, and thoughtful design, this home is ready to welcome you!

62 Whittlesey Rd, Woodbury
$850,000
4 Beds ⋅ 4 Baths ⋅ 24017869 MLS
Enter this exquisite 4Bdr, 3800sqft Colonial through it's elegant doorway leading you into a bright and welcoming foyer. This home boasts a delightful blend of classic charm and modern sophistication, offering an exceptional living experience. Entertain guests with ease in the large gourmet kitchen, featuring modern sleekness, granite countertops, complemented by a breakfast area and a wet bar. The formal dining room, adorned with a sparkling chandelier, provides a refined setting for gatherings, while the formal living room with a floor to ceiling stone fireplace is a perfect spot to relax and unwind. The office is perfect for the new work at home lifestyle. The 3 car garage leads to a small mudroom and a half bath. Upstairs, retreat to the grand primary suite, complete with a private deck, sitting/changing room, spacious walk-in closet and a luxurious ensuite bath featuring a Jacuzzi style tub. An additional two bedrooms, a full bath, laundry room and a large bonus room with ample space and comfort for family and guests. On the third floor, this home offers another large bonus room, full bath and bedroom. The full, unfinished basement offers plenty of storage or opportunity to add even more living space. Nestled on a corner lot spanning over 2.3 private acres. The home is located on a dead end road with a mere 5 homes. The best part is, if you need some entertainment the Village of Woodbury is only minutes away! Voted #1 as the most charming town in New England.

20 Birchwood Ln, Woodbury
$850,000
3 Beds ⋅ 3 Baths ⋅ 24024970 MLS
This recently fully renovated Antique has a combination of historic charm & modern amenities, which creates a truly exceptional living space. The potential for a pool adds an extra touch of luxury, while the delightful & well-maintained two-story barn in ready condition, presents exciting opportunities for conversion, whether for a guest house, pool house, or a private office on the 2nd floor office. Set within a private, park-like setting with picturesque features like a picket fence, stone walls, and professional landscaping, this home offers you a serene escape. The wide board floors and built-ins throughout add character and warmth, while the large foyer with a cedar closet sets a welcoming tone. The first floor is designed for both comfort & functionality, with a living room featuring a fireplace for cozy gatherings, a dining room that flows seamlessly into a charming kitchen equipped with custom cabinetry, marble counters, and stainless steel appliances, including a gas range. The first-floor primary bedroom, complete with a full bath boasting an oversized walk-in shower, provides a peaceful retreat. Upstairs, 3 additional bedrooms and another full bath provides ample space for guests, with access to a finished walk-up attic providing versatile options for storage or additional living space. Outdoor living is equally enchanting, with an oversized stone patio and outdoor fireplace providing the perfect setting for al fresco dining and relaxation.

258 Washington Rd, Woodbury
$840,000
3 Beds ⋅ 4 Baths ⋅ 24072388 MLS
Do not miss this beautiful home set back on a private 4.15-acre lot. Main level features a total open floor plan with vaulted ceilings and half bath. Kitchen features Kucht stainless steel appliances, Quartz countertops, with an oversized walk-in pantry. Extra Large dining, kitchen, family room area with built in sound system perfect for entertaining. Upper level adds 2 large bedrooms along with a laundry room and two full bathrooms. Additional to the 2 bedrooms is the Massive Primary suite with fireplace and sitting area, 2 large walk-in closets and a gorgeous full bath with extra-large shower with dual heads. On top of all that a gigantic 1940 square foot 4 bay garage dual deep that can hold up to 7 cars easily with 3/ 9' garage doors and 1/12' door that has a car lift for that person who likes their toys!! Back patio with hot tub. Tesla solar panels with battery backup that are owned outright not a lease that acts as a generator if power goes out! This is a custom built home just waiting for a new owner.

11 Saxony Ln, Woodbury
$840,000
4 Beds ⋅ 3 Baths ⋅ 24009580 MLS
Stunning New Construction in Woodbury. This 4 bedroom, 2.5 bathroom, 2 car garage colonial is ready for you to call it home! Beautiful flat and secluded lot gives you total privacy, while still a stone's throw away from all the stores and entertainment Woodbury has to offer. As soon as you drive in, the board and batten siding and the front porch with metal roof instantly attract your attention. This home has an open concept kitchen, dining and living areas, with hardwood floors and nine ft ceilings. The kitchen has black stainless steel appliances, white quartz countertops, a generous size island and a walk in pantry! The dining area is spacious, with a sliding door to the composite deck. In the family room, you will find plenty of windows and a propane fireplace with granite hearth, and the adjacent formal living room, or studio. In the lower level you will also find an office next to the main entrance. Make your way upstairs to the spacious primary bedroom, with its bathroom suite (including a free standing tub), as well as a double walk in closet with custom cabinetry. The remaining three bedrooms are generously sized, with another full bathroom (with tiled tub surround). The days of carrying laundry up and down steps are over, with your full size laundry room in the upper level. In the lower level, you will find a two car garage, high ceilings, and an unfinished basement that could potentially be finished (already prepared with egress windows and a walk out).

45 S Pomperaug Ave, Woodbury
$825,000
3 Beds ⋅ 3 Baths ⋅ 24192675 MLS
Welcome to 17 Curtiss Road! This one-of-a-kind 1.8-acre property offers the perfect blend of historic charm and modern convenience, featuring a well-maintained 1900 single-family home, an attached 2-car garage, and an impressive detached 24' x 50' heated 3-car garage built in 2022. Step inside the home and be welcomed by a charming foyer leading to wide-board hardwood floors and six mini-split systems (2019) that provide efficient heating and cooling throughout. The inviting living room features custom built-ins and flows seamlessly into the spacious kitchen, complete with stainless steel appliances, ample cabinetry, recessed lighting, a pantry closet, and basement access. Just off the kitchen is an updated half bath with tile flooring and laundry hookups. Off the kitchen the elegant dining room offers crown molding and plenty of space for entertaining. Completing the main level is a spacious primary suite with double closets and a beautifully updated full bath boasting heated tile floors, a skylight, recessed lighting, chair rail molding, and a linen closet. An adjoining den with custom built-ins provides the perfect space for a home office, reading room, etc. Upstairs, you'll find two generously sized bedrooms, each with walk-in closets and shared access to a Jack-and-Jill bathroom featuring a dual-sink marble vanity. The basement includes 200-amp electrical service, Energy Star hot water heater, well tank (2018), and additional laundry hookups. Outside, enjoy

17 Curtiss Rd, Woodbury
$825,000
4 Beds ⋅ 3 Baths ⋅ 24077078 MLS
Nestled in one of Woodbury's most sought-after enclaves, 77 North Gate Rd epitomizes refined living. This meticulously updated 4-bedroom, 2.5-bathroom residence spans approximately 2,519 square feet, offering a harmonious blend of modern sophistication and timeless charm. Constructed in 2016, the home's contemporary design is complemented by high-end finishes and an open-concept layout that seamlessly connects living spaces. The gourmet kitchen, adorned with top-tier appliances and elegant countertops, flows effortlessly into the dining and living areas, creating an ideal setting for both intimate gatherings and grand entertaining. Step outside to discover a beautifully crafted two-tier stone patio, perfect for alfresco dining or serene relaxation amidst the tranquil surroundings. The expansive 2.3-acre lot provides ample space for outdoor activities and future enhancements. The residence also features a substantial unfinished basement, presenting a blank canvas for customization-be it a home theater, fitness center, or additional living quarters. Situated in a neighborhood renowned for its prestige and community spirit, this home offers not just a residence, but a lifestyle of unparalleled comfort and convenience.

77 Northgate Rd, Woodbury
$812,500
5 Beds ⋅ 3 Baths ⋅ 24002484 MLS
But I thought you said it was built in 2006. You could have fooled me that this home wasn't new. Even the basement smells of new concrete. We're presenting this home to you as a "Let's just move in home." If you have a family that needs room, you got it here. With five bedrooms and ample baths you will never need a hotel for family and friends. On 3.15 acres this home has room for a pool amidst the beautifully landscaped yard. Whether it be work or play, the flexible floor plan allows for your own creative living. The location is quite nice as you have access to surrounding towns and a quiet country road to walk your dog and even you. The western exposure brings in beautiful skies in the winter and dappled light in the summer months; however, we won't forget the goings on with spring and fall. Stunning is all we have to say.

40 Tuttle Rd, Woodbury
$810,000
3 Beds ⋅ 4 Baths ⋅ 24149131 MLS
Country Living Abounds with this unique custom built one of a kind Cape nestled on 5 secluded acres. This home features an open floor plan with post and beam construction, beamed ceilings, oak floors, Plaster Walls, fully applianced Kitchen with breakfast bar, a spacious Family Room with brick fireplace, built-ins, & slider leading to back deck. The Living Room with fireplace is adjacent to a spacious Dining Room area & slider leading to large deck with access to side yard. Enjoy some quiet time in the cozy Library with fireplace and built-ins. First floor also has an Office as well as a full Bathroom. As you ascend the stairs to the second floor you will marvel at the unique lighted brick archway. Second floor boasts of a lovely Primary Bedroom Suite with brick fireplace & raised hearth, walk-in closets, Full Bath with tub, shower & vanities, and slider leading to balcony, and Two other large Bedrooms with skylights, Full hallway Bathroom, & Laundry Room with utility sink. With In-law/apartment the total living space is 3882 sqft. This home is convenient to Woodbury's town center, shops, top restaurants, antiquing, and recreation with hiking trails & nearby lake. This property has so much to offer!

148 Flanders Rd, Woodbury
$805,000
4 Beds ⋅ 3 Baths ⋅ 24102081 MLS
This pristine and much-loved shingle-style residence is located at the end of a quiet cul-de-sac in the charming town of Woodbury, known as the "Antiques Capital of CT." With four bedrooms and two and a half baths, the home is nicely sized and has room for expansion. Current owners have invested over 100k in upgrades and remodeling giving it the feel of a new build. Charming details throughout include refinished wood floors, bow windows with window seats, exposed brick and custom window treatments. The first floor includes the living room with fireplace and slider to the new Trex deck, formal dining room with nook for large buffet, remodeled kitchen with black walnut and quartz countertops, powder room with free hand stenciled walls, and mudroom with laundry accessed by side door to the two-bay garage. Also on the main level is the very spacious primary bedroom with remodeled full bath, multiple closets and French door to the deck. Upstairs are three bedrooms with large full bath. The walk-out lower level has additional space that can be finished for family room, rec room or exercise room. A new large, glassed garage door floods the space with light. This 1.388 acre pristine property was landscaped, groomed, trimmed and thinned out to the tune of $25k. Nearby you'll find restaurants, galleries, cultural venues, day spas, hiking trails, ski areas, wineries and equestrian facilities. Just 90 minutes from Manhattan.

59 Davids Hill Rd, Woodbury
$800,500
4 Beds ⋅ 3 Baths ⋅ 24033793 MLS
Ca 1760, the Hezekiah Thompson house is a warm and welcoming Dutch Colonial located on picturesque Main St in Woodbury. Perfect fusion of period details and recent updates create a graceful, elegant and livable historic home. The house offers 10 nicely sized rooms and is 2,800 sq ft with 4 bedrooms and 2.5 baths. Throughout the home you will find wide board wood floors, built-ins, paneled walls and oodles of charm and sophistication. On over an acre of land, the private grounds are flawless with a lush level lawn, perennial gardens, boxwood garden, shade trees, garden shed, two story barn perfect for workshop and two sitting areas to enjoy. A few steps outside your front door is access to the sidewalk that spans miles along this delightful tree-lined street to boutiques, cafes, antique shops and restaurants. Main Street Design zoning adds extra versatility, allowing you to run a business from house or barn with town approved uses and town approval. List of updates available.

487 Main St S, Woodbury
$800,000
3 Beds ⋅ 3 Baths ⋅ 170621359 MLS
Privacy abounds on this beautifully maintained 4.15 acre property situated at the end of a private cul-de-sac! The home features one level living at its finest complete with 3 bedrooms and 2.5 baths. The oversized living room's centerpiece is a stone fireplace with wood insert for efficient wood heating and custom beams across the ceiling. The kitchen features a large center island, Corian countertops, and an open concept to the dining room & office. The primary suite features three closets and a full bath with a soaking tub. The second and third bedrooms are oversized as well with a jack-and-jill bathroom between. The basement has potential to be fully finished, which would double the square footage of the home, and is already plumbed for an additional bathroom. Head outside to enjoy the massive 14x60 ft Mahogany deck, large backyard, and detached barn, which includes a space that may be converted into additional living space (consult with Town of Woodbury). Also features a 14,000W whole house generator.

42 Timber Ln, Woodbury
$789,900
4 Beds ⋅ 3 Baths ⋅ 24019759 MLS
If you have been searching for the perfect new construction with Master on the first floor nestled in a quaint New England setting, this lovely Colonial country home is the best of both worlds. This home is just 90 minutes from New York City and 45 minutes from either New Haven or Hartford. Don't miss this opportunity new construction in very desirable location in lovely Woodbury.Move in to your ultimate dream home in this tranquil setting but be still relatively close to all highways, town, and all the amenities. This state of the art 4 bedroom, 2 full/1 half bath home is built to perfection,the ideal blend of high quality craftsmanship with a high-end transitional finishes. Well thought out floor plan with large rooms and open concept living. Spectacular chef's kitchen with high end appliances, large center island all open to family room and dinning room,just fabulously designed for modern life style. Large master bedroom suite with walk-in closets, and opulent master bath. Home is ready for you to move in .Exceptional Home By CORBO.

lot 9 Strong Field, Woodbury
$776,400
3 Beds ⋅ 5 Baths ⋅ 24074526 MLS
Set on 3.5 acres with 150 feet of Pomperaug River frontage, this expanded Cape blends classic charm with thoughtful updates. Featuring 3 bedrooms, 4.5 baths, and multiple living areas, this home is designed for comfort and entertaining. The kitchen has been beautifully updated, featuring leathered granite countertops, stainless steel appliances, and custom cabinetry, making it both stylish and functional. The sunlit family room boasts vaulted ceilings and a cozy window seat, offering a perfect spot to enjoy nature and birdwatch overlooking an expansive mahogany deck. A formal living room with a fireplace and a dining room with its own fireplace create warm, inviting spaces. The first-floor bedroom adds convenience and flexibility. Upstairs, the spacious master suite features a full bath, while a guest suite with a private bath provides extra comfort. . Refinished hardwood floors on the main level enhance the home's character and warmth, new flooring upstairs, and fresh paint throughout give the home a refreshed, move-in-ready feel. The finished walk-out basement features a wet bar and additional living space, perfect for entertaining or relaxation. Located just minutes from downtown and major highways, this stunning property offers the perfect balance of privacy, convenience, and scenic riverfront living.

896 Main St S, Woodbury
$775,000
4 Beds ⋅ 5 Baths ⋅ 24017840 MLS
Immaculate country cape on a quiet, private 18 acre lot with views and lovely landscaping. There is a main level primary suite with a fireplace, luxurious bath with soaking tub and shower and a walk in closet. The main level also has a gourmet kitchen, living room with a fireplace, formal dining room, family room with fireplace and access to a covered porch and a rear patio with screening. There are 2 half baths on the main level and a laundry room. The upper level has 3 bedrooms and an office. One on suite bedroom and a jack and jill set up with the other two. The basement is a walk out to the side yard. It is unfinished but does have a fireplace and potential. The 18 acres is mostly wooded. The location is close to Woodbury town center with great restaurants, shops, antiquing, art galleries and so much more. Active on May 29. Make your appointment now.

60 Stone Pit Rd, Woodbury
$775,000
4 Beds ⋅ 3 Baths ⋅ 24115107 MLS
Experience elevated New England living at 6 Strong Field Road, an exceptional 2024 custom-built Cape Cod residence set on a private, manicured 1-acre lot in one of Woodbury's most desirable enclaves. Designed for discerning buyers, this 4-bedroom, 2.5-bath masterpiece blends architectural sophistication with everyday comfort. Inside, you're welcomed by an airy open-concept floor plan, enhanced by dramatic vaulted ceilings, expansive windows, and finely crafted wide-plank hardwood flooring throughout. At the heart of the home is a designer gourmet kitchen-a showcase of form and function-featuring premium quartz countertops, custom cabinetry, a professional-grade appliance suite, and an oversized island perfect for hosting or gathering. The adjoining great room offers a warm, elegant atmosphere anchored by serene views and refined finishes. The first-floor primary suite is a luxurious retreat with a spa-style bath, dual vanities, walk-in glass shower, and a generous walk-in closet. A main level office is idle for work-from-home living. Upstairs, three additional bedrooms and a full bath accompany a spacious loft, perfect for a media lounge or reading retreat. Tucked at the end of a quiet cul-de-sac, just minutes from historic Woodbury's shops, dining, nature preserves, and top-rated schools, this home is a rare opportunity to enjoy elevated country living with modern convenience. Unmatched style, craftsmanship, and comfort-schedule your private showing at 6 Strong Field

6 Strong Field Rd, Woodbury

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