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$775,000
3 Beds ⋅ 3 Baths ⋅ 24001878 MLS
Beautiful Litchfield County horse property boasting 9.88 open acres, a 47x37 4-stall barn and approximately 3000 running feet of post and rail fencing enclosing 4 large pastures for turnout. In addition there is a small barn which holds 2 cars. This contemporary cape features a separate area ideal for an in-law setup. Enjoy picturesque views from the 3-season screened porch overlooking the rushing brook, koi pond and the stunning Litchfield hills. The beautifully remodeled kitchen, complete with a fireplace, granite countertops and wood floors is spacious and filled with natural light. The present owner has supplied a list of upgrades which illustrate the love she has for this home. In the Living In Sunday section of New York Times dated May, 2021 it features Woodbury, Ct. as Peace, Quaint Beauty and a Sense of History. The Reader's Digest again just named Woodbury "The Best Small Town in Ct." This convenient location makes a quick ride to the town center where you can walk to stores, library, community center, schools, medical appointments, summer outdoor concerts, community theater, beautiful live music in Hollow Park plus hike to the tower overlooking the town and so much more! Come enjoy this home and the wonderful small town with parks and open spaces, Flanders Nature Center, hiking trails, its roads meandering past three rivers--the Pomperaug, Weekeepeemee and Nonnewaug plus golf courses and private schools. Bradley Airport is approx. 1 hr. away.

819 Main St N, Woodbury
$770,000
4 Beds ⋅ 4 Baths ⋅ 170606501 MLS
This impeccably maintained Colonial home, nestled in a coveted section of Woodbury showcases three levels of living space. Begin with a grand two-story foyer graced w/ marble flooring. The 1st level has a well-appointed office with custom built-ins, bright and spacious LR & DR that spans from front to back, and an open kitchen w/ granite counters, S.S appliances, a built-in wine cooler, and a dining area w/ natural light from windows and skylights. Adjacent to the kitchen, a sunken family room features fresh hardwood floors and an efficient new pellet stove. Beyond the dining area lies a deck with distant views and abundant privacy. The 2nd level reveals 3 generously proportioned bedrooms, including a primary suite spanning three rooms. The suite boasts Trey ceilings, Hickory floors, dual walk-in closets, a cozy sitting room, and a custom en suite bathroom with W-in closet and laundry. The 2nd 3rd bedrooms provide ample closet space and share a well appointed full bath. Descending to the lower level, a space exuding warmth and natural light extends the living area by over 900 sq. Ft. 11-foot ceilings, hickory flooring, a marble bath & steam shower, kitchen area with granite countertops, a charming built-in seating nook, and a Murphy bed for guests, this floor is an inviting retreat. French doors give access to a bluestone patio, a plunge pool, and a meticulously manicured yard. Irrigation, Generator, and surround sound complete this home. 90 min to NYC and 30 min to train.

557 Upper Grassy Hill, Woodbury
$769,000
3 Beds ⋅ 3 Baths ⋅ 24017605 MLS
Located in The Beautiful Hills of Litchfield County on the Woodbury / Roxbury Line! Lots of Privacy Awaits You in this Beautiful Colonial/Contemporary on 9.97 Acres of Serenity w/ Mature Trees, Plantings, Lush Greenery & the Peaceful Sounds of Transylvania Brook that Flows Behind the Home. Inground Heated Gunite Swimming Pool w/ Beautiful Stonework, Fenced in Yard & 3 Good Size Sheds. Very Unique Home w/ Double Door Entry that Leads you into a Spacious Foyer w/ an Indoor Water Feature, 3 Generous Size Bedrooms, Remodeled 2.5 Baths, w/ Italian Marble Tile, Recessed Lighting throughout Home, Lower Level Family Room w/ French Doors leading out to Patio & Swimming Pool, Office Space, 4 Season Sunroom w/ French Door & Plenty of Windows, 2 Car Garage, Lots of Storage, Huge Unfinished Basement, C/AIR & Whole House Generator. Primary Bedroom Suite Features a Separate Room that can be used as You Choose w/ Lots of Windows, Jacuzzi Tub, Walk in Closet & Balcony Overlooking Swimming Pool. Long Paved & Lighted Private Driveway Leads You to an Oasis. A Nature Lovers Dream! This Home is a Must See!

24 Roxbury Rd, Woodbury
$765,000
4 Beds ⋅ 4 Baths ⋅ 24096938 MLS
Set on a quiet cul-de-sac and bordering open space, this beautifully maintained 4BR, 4BTH colonial blends charm w/modern comfort & functionality. Step into the grand foyer flanked by a sunken living room with fireplace and private home office. At the heart of the home is the updated eat-in kitchen, featuring abundant white cabinetry, marble countertops, a butcher block center island, and stainless-steel appliances. The kitchen transitions into the family room with a second fireplace and to the turret-style dining room, filled with natural light and offering panoramic views of the private backyard. Rich hardwood floors throughout-brand new upstairs-complement the home's neutral palette. A gorgeous custom-designed laundry room and a beautifully updated full bath with modern and stylish finishes complete the main level. The upper level is highlighted by a large primary suite complete with remodeled cedar walk-in closet and spa-like en-suite bath. Three additional bedrooms include one with a remodeled ensuite bath, while the other two share an updated Jack-and-Jill bathroom. The unfinished lower level offers endless potential for additional living space. Outside, enjoy the beautiful in-ground, heated pool (2020), spacious decks, perfect for entertaining, and backyard privacy. Ample parking w/an attached 3-car garage & spacious driveway. Just minutes from scenic Main Street, fine dining, Hollow Park, hiking trails & more. Great opportunity-lovingly maintained-convenient location.

3 Inwood Ln, Woodbury
$765,000
3 Beds ⋅ 3 Baths ⋅ 24102299 MLS
Welcome to one of the most charming communities in Connecticut. This darling of an antique home sits in the heart of Woodbury, CT. It is a Dutch colonial dating to circa 1700, bought in 1750 by a well-respected, wealthy local merchant/ financier, Jabez Bacon. The building became the town's first general store, known as the Red Store. After Bacon's death, the property served as a school and later as a tavern. Daniel Curtis a direct descendant of one of the founders of the town of Woodbury, bought the dwelling as part of a homestead in 1831. Since then, it has been home for only a handful of families. In January of 1934, the house was featured in an issue of American Architect for its design and modernizations. Recent updates have not spoiled the historic character of this truly charming residence. The original hand-hewn beams, stone fireplaces, wide planked floors, beautiful Dutch doors, stone floors are only a few distinctive aspects of this house. The original Tomahawk door greats guests to this treasure of a dwelling. Rock away sunny afternoons or moonlit evenings on the spacious front porch. New HVAC system and roofing in 2022. The bright, newly updated kitchen and bathrooms, spacious living and dining rooms, and cozy bedrooms are all welcoming living spaces. The property is surrounded by beautiful mature trees, shrubs and flowers. A stroll in any direction will take you to a town park, restaurants, shops and churches. Don't miss out on this unique antique

34 Hollow Rd, Woodbury
$765,000
4 Beds ⋅ 4 Baths ⋅ 24123798 MLS
The Tomlinson House, built in 1783, offers a rare chance to own a piece of Woodbury's history. Set on 5+ acres along Middle Road Turnpike, with an additional .87-acres across the street, this 4-bedroom Colonial combines period charm with enduring potential. Historic character is evident throughout-restored wide-board hardwood floors, original millwork, and four (non-working) fireplaces, including a dramatic walk-in hearth with beehive oven. The floor plan provides the best of both worlds: a welcoming open flow between the kitchen and family room for gatherings around the hearth, balanced with dedicated dining and living rooms for more traditional entertaining. A main-level office/bedroom and screened porch add versatility. Upstairs, front and back staircases lead to three spacious bedrooms, two full baths, and a third-floor office with half bath. Recently refinished hardwood floors continue across the upper levels, preserving the home's warmth and continuity. The level property is a highlight...park-like and pastoral, with stone walls, a brook, pond, mature plantings, screened porch and a bluestone patio for outdoor living. A two-car garage with attached shed offers workshop or storage space. With strong bones, timeless appeal, and room to grow, the Tomlinson House is a unique offering in one of Woodbury's most desirable corridors

393 Middle Road Tpke, Woodbury
$760,000
3 Beds ⋅ 3 Baths ⋅ 24003913 MLS
Stunning light filled Modern Cape, meticulously rebuilt with top-tier craftsmanship. This home boasts an inviting open floor plan, accentuated by soaring cathedral ceilings and a charming wood fireplace adorned with stone and plaster finishes. The kitchen, complete with a central island and high-end appliances, seamlessly flows into a comfortable dining area. Step out from the first-floor great room onto a ground-level deck overlooking a serene brook. The main level also features a well-appointed bedroom, full bath, and office for remote working. Upstairs, discover a convenient laundry room, a third bedroom with an en suite bath, and a breathtaking primary suite. Indulge in the opulent primary bathroom, featuring heated floors, a sumptuous soaking tub, and a spacious master closet with custom built-ins. The recently finished basement offers an additional 500 square feet of living space, including a cozy family room and a small exercise area. Outside, enjoy the privacy of a level yard surrounded by stone walls, with sheds for storage and an oversized two-car garage completing the picture. This tranquil retreat is conveniently located just 10 minutes from four town centers, offering the perfect balance of seclusion and accessibility.

317 Church Hill Rd, Woodbury
$760,000
4 Beds ⋅ 4 Baths ⋅ 24100794 MLS
A short 2.5 hour drive to New York City! 133 Hoop Pole Hill Rd. offers refined country living in this exceptional 4-bedroom, 3.5-bath home set on a peaceful 3.32-acre wooded lot. Surrounded by nature, this well built home blends timeless charm with modern convenience. Step inside to find a bright and inviting foyer, beautiful hardwood floors throughout, and a layout made for everyday living. The main level offers flexible space with custom book shelfs for a home office or guest bedroom, a welcoming living room with sliding barn door, and a warm family room centered around a new wood-burning fireplace. The gourmet kitchen is a standout, equipped with high-end appliances including a Thermador gas range, double ovens, new refrigerator, new dishwasher and a spacious walk-in pantry. A secondary staircase from the kitchen provides easy access to the upper level. Upstairs, the serene primary suite includes a sitting area, fireplace, two custom his and her walk-in closets and dressing room, a luxurious bath with soaking tub and separate shower. Three additional bedrooms complete the second floor, including one with a private en-suite bath. Recent updates include a new, state-of-the-art, desireable heat pump system and hot water heater, updated flooring and new front porch and whole house generator. Outdoor amenities include a sunroom, a beautiful entertaining patio, a 3-car garage with basement access, and a 2-bay barn with sliding doors-perfect for extra parking or storage.

133 Hoop Pole Hill Rd, Woodbury
$755,000
4 Beds ⋅ 4 Baths ⋅ 24057765 MLS
Highest And Best due by1/13/2025 11:59:00 PM MST. Great Colonial in a nice neighborhood, needs updating. Proof of funds or Pre- Approval with all offers. No changes to P&S / addendum to be signed within 48hrs of acceptance..Buyer and/or agent to verify property information.

92 Tuttle Rd, Woodbury
$751,000
4 Beds ⋅ 4 Baths ⋅ 170579787 MLS
Total dream home nestled on a private, magnificent treed 3.32 acre lot with great seclusion. This magnificent 4-bedroom, 3 ?-bath residence boasts exceptional features throughout. Enter the granite steps to the 1st floor with all hardwood flooring, dramatic foyer with front staircase, and surprises around every corner. 1st-floor home office or bedroom. Living room with beautiful barn door. Family room with wood-burning fireplace. Gourmet kitchen with professional-grade appliances- Thermador gas range, new oven & microwave/convection combo, oversized fridge and freezer and large walk-in pantry. Back staircase from the kitchen leads to upper level. Primary bedroom is a true oasis, with a fireplace and sitting area. Two custom-built walk-in closets, offering abundant storage and a beautiful en-suite bathroom with separate shower and spa-like jacuzzi tub. 3 additional bedrooms on upper level, one having an ensuite bath. Freshly painted and new stylish light fixtures. Fantastic screened-in porch. Ample parking space for RV with 50 amp service and sewer access. 3-car garage with basement access. 2-bay barn with sliding doors, offering additional parking/storage options. Barn can be easily converted into 2 horse stalls. Home is extremely well-built. Excellent New York weekender property. Convenient location to all of the wonderful things to do in Litchfield county- antiquing, fine dining, art galleries, Connecticut Wine Trail.

133 Hoop Pole Hill Rd, Woodbury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24160410 MLS
HIGHEST & BEST OFFERS DUE BY NOON ON MONDAY, 4/13/26 - Fantastic opportunity to own this beautifully maintained 4-bedroom, 2.5-bath Colonial on lovely cul-de-sac neighborhood, privately set back on a wooded lot which backs up to Land Trust in sought-after Bear Run Estates. Proudly offered by its original owners, this home features numerous updates including a high-efficiency propane furnace (2023), central A/C (2024), and whole-house Generac generator (2023). A welcoming 2-story foyer leads to a fantastic eat-in kitchen with granite countertops, tiled backsplash, stainless steel appliances, breakfast bar, under-cabinet lighting, and pantry. The desirable open floor plan flows into the inviting family room with a propane fireplace and custom bookshelves. A private home office with a wall of built-ins, formal dining room, separate living room, and powder room with laundry complete the main level, all with beautiful hardwood flooring. Upstairs, the spacious primary bedroom suite offers exposed beams, walk-in closet, and renovated bath with soaking tub, tiled walk-in shower, and heated floors. Three additional generously sized bedrooms share a full bath. The walk-out lower level provides flexible finished space for a recreation room, gym, or guest area, plus additional unfinished storage space for future expansion. Professionally landscaped grounds feature a storage shed and maintenance-free Trex deck, perfect for outdoor entertaining.

54 Bear Run, Woodbury
$750,000
4 Beds ⋅ 3 Baths ⋅ 24132227 MLS
Beautifully Spacious Colonial in the Heart of Woodbury. This inviting in-town colonial offers the perfect balance of charm and convenience-just 5 minutes from town parks, top-rated Woodbury schools, shopping, and restaurants. Freshly refinished hardwood floors bring a warm glow throughout the home's 3,200 sq. ft. of well-crafted living space. The main level features a sun-filled kitchen and great room with 9-foot ceilings, a center island, eat-in area, and a cozy fireplace. A welcoming living and dining room, a practical mud/laundry room, and a private office with elegant French doors complete the first floor. Upstairs, you'll find three generously sized bedrooms, along with a primary suite with a walk-in closet and luxurious bath. A versatile recreation room with built-in bookshelves-accessible from both the main hall and the primary suite-offers the perfect space for a library, playroom, or studio. Set on a level lot, the home invites outdoor enjoyment with a private back deck, a charming front porch, and ample room for weekend gatherings.

118 Good Hill Rd, Woodbury
$750,000
4 Beds ⋅ 4 Baths ⋅ 24096486 MLS
Beautifully constructed and perched atop a scenic 3+ acre lot, this stately gambrel colonial is just a 5-minute drive from charming downtown Woodbury. Offering 4 to 5 bedrooms, this home features everything one would expect in almost 3400 square feet of living space; a formal dining room, a large front-to-back living room with a fireplace and hardwood floors, and a spacious eat-in kitchen with a center island. The generous family room is the heart of the home, boasting vaulted, beamed ceilings, a cozy fireplace, hardwood floors, and French doors leading to both the front and back yards. Upstairs, you'll find four bedrooms and two and a half bathrooms, along with a private au pair suite located above the garage-perfect for guests or extended family. Additional highlights include an oversized two-car garage, a walkout lower level with a third garage door, and enough space to accommodate three to four smaller vehicles. The exterior is impeccably maintained with expansive lawns, a pond with wild flowers, mature plantings, blue stone walkways and patios, classic stone walls, and a backyard pavilion- ideal for enjoying the outdoors while staying shaded from the sun.

181 Railtree Hill Rd, Woodbury
$745,000
4 Beds ⋅ 3 Baths ⋅ 24032582 MLS
Experience the charm of this welcoming Frank Betz designed home, thoughtfully crafted to accommodate today's fast-paced lifestyles. Step into the contemporary open floor plan featuring 12' ceilings, elegant arched openings, and a stunning kitchen/great room boasting granite counters, stainless steel appliances, gas stove top, double wall oven, and a center island with seating for 4. With over 2800 square feet of space, the private master wing offers a tray ceiling, wood floors, his and her closets, and a luxurious whirlpool tub. The formal dining and living rooms showcase arched openings and wood floors, while the main level family room impresses with a cathedral ceiling, floor to ceiling stone fireplace, and french door leading to the front patio. The main floor is completed by two additional bedrooms and a full bath. This low-maintenance home includes a newly finished fourth bedroom on the upper level, with expansion possibilities in the walkout lower level that is already plumbed for an additional bath. Nestled on a private interior lot adjacent to open space, this home is conveniently located just a short distance from the town center and schools.

174 Minortown Rd, Woodbury
$743,400
4 Beds ⋅ 4 Baths ⋅ 170588519 MLS
This is the home you’ve been waiting for! Located on a quiet cul-de-sac within walking distance to Downtown Woodbury, Three Rivers Park and the Pomperaug River you will enjoy life to its fullest. This home has 4 spacious bedrooms, two of which are considered Primary Bedroom Suites. The first floor Primary Bedroom with vaulted ceiling, has its own private Bathroom with soaking tub and walk in closet. The Kitchen is brand new with all top of the line appliances including a Wolf Gas Range and SubZero Refrigerator. Wolf Double ovens, Dishwasher and Warming Drawer complete the package. The Island is huge and makes for a wonderful place to bake, serve appetizers and meals when you entertain and has room to sit for a casual meal. It’s also a great spot for homework and craft projects. The Dining Room is just off the Kitchen plus there is a large first floor Office complete with built-in bookshelves and cabinets with a nice view of the front yard. There are hardwood floors throughout. The Main Living area includes a fireplace and opens through French Doors to the fully fenced pool and patio area which will be a favorite spot for a swim or just to bask in the sunshine. The entire backyard is fenced, in addition to the pool area, to keep your pets and others safe. The lower level is partially finished and is a great place for movie night plus there is plenty of storage space and room for your home gym. Set up your personal showing today!

18 River View Ln, Woodbury
$740,000
5 Beds ⋅ 4 Baths ⋅ 24171620 MLS
Center Hall Colonial with Full In-Law! This majestic brick facing home flaunts its location atop a private lot overlooking sprawling scenic views. Main level features a two-story foyer, formal dining room w/hardwoods & pocket doors leading to a high-end kitchen w/stainless steel appliances including a gas stove. The kitchen delivers with granite tops, upscale cabinetry, breakfast bar, & eat-in area facing French doors opening to a welcoming living room w/hardwood, vaulted ceilings & brick fireplace. The family room/study pulls in the strength of hardwoods, tray ceiling & plenty of natural lighting. The main level bedroom/office & guest bathroom complete this central level. Continuing the journey upstairs & you will be greeted by spectacular views from the transom window aloft the staircase. The path to the primary bedroom suite introduces a tray ceiling, large walk-in closet & full bath w/whirlpool tub, shower stall & skylight. The three additional bedrooms are generous in size while the laundry room, common full bath w/double sink vanity & tub/shower concludes this upper level. The main level full in-law is a desirable focal point showcasing a separate entry, remodeled eat-in kitchen, living room w/vaulted ceiling, gas fireplace, large bedroom, remodeled full bath, laundry closet & staircase to garage w/private basement. Exterior features two new A/C condenser units, custom retaining walls, large deck & three car garage. This sought-after home exceeds all expectations!

17 Carriage Ln, Woodbury
$740,000
4 Beds ⋅ 3 Baths ⋅ 24099108 MLS
This beautiful, well maintained, light and bright Colonial sits on a lot of just over 2 acres, complete with perennial gardens, stone walls stairs and pathways and bucolic views. Freshly painted inside and out, this home features a stunningly updated kitchen with walk in pantry and stainless steel appliances. The family room boasts vaulted ceilings, lots of space and a fireplace. The Primary Bedroom Suite is located on the main level with access to the generously sized deck. Additional 3 bedrooms are on the upper level along with a lovely full bath and good size hallways. Wired for full house generator as well as ADT system. Additional 270 sq ft of finished space in lower level and on Field Card. All of this just minutes from downtown Woodbury. A quintessential New England town, with popular restaurants and shops. Capital of the Antiques Trail.. Attic/storage in the bedroom under the eaves.

101 Railtree Hill Rd, Woodbury
$740,000
3 Beds ⋅ 2 Baths ⋅ 24022510 MLS
I want to live here, says EVERYONE. This main street property allows you to walk to all town activities, shops and restaurants. Being set way back from the road is a rare find in the Village of Woodbury. The home is a sweet cape, built in 1930 style (like a rock) with a circular open plan. Four season porch with expansion possibilities for a first floor primary bedroom. The barn is the secret feature. Main Street Design District allows a full business on the property and the most recent business in the barn was a flower shop. Beautifully planned out, it has a picture window that you can watch life go by while creating. But wait! Included upstairs is a one bedroom apartment you can use for income along with the shop, or just have overflow and party space for family and friends. Several outbuildings also flank the driveway. The land is flat with beautiful terraces and private gardens on 2.51 acres. It's a gem and you will say, I can't wait to live here.

473 Main St S, Woodbury
$735,000
4 Beds ⋅ 3 Baths ⋅ 24072559 MLS
Nestled in the heart of Woodbury, with easy access to the picturesque towns of Litchfield, Washington, and Roxbury, this newly constructed modern farmhouse-style home offers the perfect blend of comfort, privacy, and New England charm. Built with quality craftsmanship and energy-efficient features, this serene retreat boasts 3 spacious bedrooms, 2.5 bathrooms, plus a versatile 300+/- sq. ft. finished bonus room. The property sits on three acres of beautiful, private land, offering a peaceful sanctuary surrounded by natural beauty. Designed for both relaxation and entertaining, the open-concept kitchen, dining, and living area features a cozy indoor gas fireplace, creating a warm and inviting atmosphere. Step outside onto the back deck, where you can take in expansive, breathtaking views of the meadow and mountains or unwind in the luxurious cedar hot tub. Situated in close proximity to top private schools like Taft and Westover, the home also offers easy access to outdoor recreation, dining, shopping, and local farms, with attractions such as Quassy Amusement Park just a short drive away. Experience the charm and tranquility of Litchfield County living, all while being just two hours from New York City. Now available for sale, a rare opportunity to own a stunning move-in-ready home in one of Connecticut's most desirable areas. The home is currently furnished, and owners are open to selling furnished, partially furnished or unfurnished. Owner is broker/agent.

29 Fawn Meadow Ln, Woodbury
$735,000
3 Beds ⋅ 3 Baths ⋅ 24051786 MLS
Envision your perfect escape at the Francis Hall House-an elegant and unique 1836 brick home in late Federal style, nestled on approximately 3 acres. This lovingly maintained property boasts a flexible and comfortable floor plan with 3 to 4 bedrooms and multiple fireplaces. Ideal for working from home, hosting guests, or entertaining, it offers inviting indoor and outdoor spaces. Located in historic Hotchkissville, you'll enjoy convenient access to I-84, Woodbury Center, and Washington, while still being a short drive from New York. The Francis Hall House beckons you with promises of comfort and relaxation. Don't miss your chance to make it your home!

194 Washington Rd, Woodbury
$725,000
4 Beds ⋅ 4 Baths ⋅ 24137870 MLS
Welcome to Eastfield Farms Etates. This Colonial features an open floor plan for comfortable everyday living an entertaining alike. The large foyer flows to both the formal living room with french doors and formal dining room. Both with crown molding and accent lighting. Just down the hall step into the spacious kitchen with center island, granite counter tops stainless appliances. The dining area flows to the family room with stone wood burning fireplace and french doors leading the the back deck. The laundry room is conveniently located on the main level through the mud room. Round out the first floor with a half bath. Hardwood floors throughout the first floor. The upper level offers primary bedroom with four closets and a large bathroom with jetted tub and double sink vanity. The second bedroom is large enough to have its own seating area. There are two other bedrooms and a large bathroom. The attic has pull-down stairs. The basement is unfinished with plenty of storage. You will enjoy this lovely level landscaped spacious yard, two car attached garage and full shed. Convenielty located to Watertown and Middlebury, 90 minutes to NY City.

432 Quassapaug Rd, Woodbury
$722,000
3 Beds ⋅ 2 Baths ⋅ 24084121 MLS
Highest and Best by Monday July 7th at 5pm. Introducing "The Lighthouse," an architectural treasure from 1960 by Robert P. Keating, set amidst 4+ acres of secluded treescape. This Mid-Century Modern boasts classic features like American Redwood beams, birch built-ins, and walls of glass that dissolve boundaries of indoor-outdoor living. The heart of the home is the open-concept main floor with soaring vaulted ceilings, a striking fieldstone fireplace, and a primary ensuite bedroom, complemented by two more bedrooms sharing a full bath. In addition a playroom/den, large dedicated office space and/or spare bedroom complete the first floor. Step outside to unwind on the expansive decks or gather around the cozy fire pits in the outdoor sitting areas, all while enjoying the natural tapestry of the property. Just a 90 minute drive from the bustle of NYC, this retreat is moments away from the quaint shops, parks, and eateries of historic Woodbury.

29 Lighthouse Rd, Woodbury
$710,000
3 Beds ⋅ 4 Baths ⋅ 24155513 MLS
Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. This stately circa 1845 home blends historic character with comfortable living. Set along scenic Good Hill Road and surrounded by lush, established gardens, featuring a black bottom gunite pool, private terrace, welcoming front porch, and charming potting shed, creating a peaceful retreat. Inside, a sun-filled front-to-back living room offers elegant moldings, custom built-ins, and a wood-burning fireplace. The adjacent study, with built-in bookcases and a second wood-burning fireplace, provides an ideal home office or quiet sitting room. The warm and functional kitchen includes solid wood, custom cabinetry, a brand-new Thor stove, and a breakfast nook. A versatile side room, with full bath, offers flexibility for a pantry, office, or first-floor bedroom. The dining room, just beyond the wet bar, overlooks the terrace and is perfect for gatherings. Upstairs are three spacious bedrooms and two full baths, including a primary bedroom with fireplace, wall of closets and private en-suite. Cedar-lined closets are found throughout. A classic two-story barn provides three-car parking plus ample storage or hobby space and an area to lounge by the pool. Central air and a whole-house generator complete this idyllic country retreat. Good Hill leads directly to Main St. and Hollow Park, road construction ends in May

58 Good Hill Rd, Woodbury
$707,000
3 Beds ⋅ 4 Baths ⋅ 24147161 MLS
Nestled within the exclusive South Brook community, 19 Hill View Lane offers timeless New England charm paired with exceptional craftsmanship. This beautifully appointed 3 bedroom, 3.5 bath cape colonial is rich in architectural detail, featuring refined millwork, quality finishes, and a thoughtful layout designed for both everyday living and elegant entertaining. The main living spaces flow effortlessly, filled with natural light and a warm, inviting ambiance that immediately feels like home. Beneath the main living area lies a space designed purely for enjoyment. The finished lower level features a Roman-style sauna, wet bar, recreation room, and a full bath, creating the perfect space for entertaining, relaxing, or unwinding at the end of the day. Set on a picturesque lot within a quiet, well maintained neighborhood, this home offers a rare blend of privacy and community. Residents enjoy award-winning dining, entertainment and boutique shopping within just a quarter mile from home. Located just minutes from the historic town center of Woodbury, scenic parks and highly regarded schools all while being centrally positioned for easy access throughout Litchfield County. A truly special home where classic design meets refined living. Association rules apply.

19 Hillview Ln, Woodbury
$705,000
3 Beds ⋅ 3 Baths ⋅ 24152365 MLS
Experience the ease of single-level living in this lovingly maintained residence. Nestled on a private lot bordering acres of open space, this home is a study in thoughtful design and architectural detail. The interior is defined by a sense of scale and light, featuring hardwood floors, elegant tray ceilings, and custom crown moldings. At the heart of the home, the spacious living room is anchored by a classic fireplace and handsome built-ins. The eat-in kitchen invites warmth with the "chestnut glow" of its cabinetry, beautifully paired with polished granite countertops and a convenient breakfast bar. Seamlessly blending indoor and outdoor living, the home features a three-season sunroom, complete with a "family room" style fireplace-the perfect setting for crisp New England evenings. Designed for ultimate privacy, the "split-wing" floor plan separates the guest quarters-where the bedrooms share a refined marble-clad bath-from the expansive primary suite. This sanctuary features a walk-in closet and a versatile in-room nook, perfect for a private seating area or workspace. For the professional, a dedicated separate office rounds out the living areas.

43 Mill Rd, Woodbury
$700,000
3 Beds ⋅ 1 Baths ⋅ 170529378 MLS
Unique opportunity to own approximately 87 acres with an Antique home with barns, stalls and riding ring, in need of tlc. There are four lots that make up the 87 acres One lot in Bethlehem and Three in Woodbury. Lot 1- 7.00 acres Located in Bethlehem, Ct. Lot 2 - 7.22 acres. Lot 3 with house and barns is -11.59 Acres and Lot 4 with 61.76 acres. Sold all together will not divide. Property is currently an operating horse boarding facility. Main Barn with a 60 x 120 indoor riding ring plus 20 stalls. Feed room and tack room. Offices on the second floor. Two additional post and beam barns with stalls and loads of storage space and potential. Outdoor riding ring. The 1795 Colonial needs to be completely redone. It's down to the studs and awaiting to be remodeled. Overall this property offers loads of possibilities.

575 Weekeepeemee Rd, Woodbury
$700,000
4 Beds ⋅ 3 Baths ⋅ 24093733 MLS
Nestled in a sought-after neighborhood, this charming Colonial home welcomes you w/ its classic wrap-around porch, mature plantings, & timeless curb appeal. Inside, you'll find a formal living room w/wood-burning fireplace, formal dining room, powder room & laundry area, & bright kitchen w/ granite countertops, stainless steel appliances, breakfast bar w/ backyard views, & cozy dining nook. Kitchen flows seamlessly into the family room, where sliding doors lead to a beautiful stone patio-ideal for indoor-outdoor living. Additional highlights on main level include hardwood floors & interior access to the 3-car garage. Upstairs, the primary suite features vaulted ceilings, full bath w/ double vanity, shower stall & soaking tub, & walk-in closet. Three additional bedrooms, full hall bath w/ tub/shower, & large bonus room w/ vaulted ceilings complete the second floor. Bonus room offers endless possibilities & could easily serve as a guest suite, playroom, or home office. The spacious, level yard includes a custom 57' x 33' "No Till" garden, established in 2021 offering abundant growing space & thoughtfully designed layout. Enter through one of two handcrafted oak arches that add rustic charm & character. Wide walkways provide easy access for planting, harvesting, & maintenance. The garden also includes three elegant cattle panel arches & a variety of perennial herbs, creating a productive & visually appealing space for any gardening enthusiast. Enjoy the added bonus of recent

16 Fairgrounds Rd, Woodbury
$699,000
3 Beds ⋅ 3 Baths ⋅ 24185444 MLS
Meticulously maintained and handsomely set on a picturesque lot in charming Woodbury, Connecticut, this classic Colonial offers the perfect blend of timeless character, comfort, and outdoor beauty. From the moment you arrive, the home makes a lasting impression with its mature tree-lined setting, stone walls, flowering gardens, cobblestone and bluestone walkway, and inviting front entry. Inside, sun-drenched rooms create a warm and welcoming atmosphere, giving the home an immediate sense of comfort and ease. Thoughtful details, generous living spaces, and a graceful floor plan make this a home that feels both elegant and truly livable. The inviting living and dining areas flow beautifully for everyday living and entertaining, while the bedrooms offer peaceful retreats filled with natural light. The primary suite is a special highlight, featuring its own Romeo and Juliet balcony overlooking the gardens and professionally maintained grounds. It is the kind of private, charming detail that gives the home a rare sense of romance and character. Outdoor living is just as impressive. Enjoy a private bluestone patio, beautifully framed by stonework and landscaping, along with a spacious Trex back deck designed for relaxing, dining, and entertaining. Whether enjoying morning coffee, summer gatherings, or quiet evenings surrounded by nature, the property offers a peaceful country setting while still being close to the charm, shops, restaurants, and conveniences of Woodbury.

674 Middle Road Tpke, Woodbury
$680,000
4 Beds ⋅ 3 Baths ⋅ 170572308 MLS
Stately 3300 sq. ft. colonial in sought after Woodbury. Perfectly located near Middlebury and Watertown border, this 4-bedroom home has been lovingly cared for. As you enter the two story foyer there is a generous library or office with pocket doors to the right and formal dining room to the left. The DR offers picture frame and crown moldings with another set of pocket doors. A chef's kitchen with plenty of room for cooking, baking and entertaining around the large granite island. A tasteful tile backsplash, loads of cherry cabinets and updated appliances plus an informal dining area are open to the bright family room. FR has fireplace with built in bookcases, crown moldings and a slider to outdoor patio. Primary bedroom suite with double walk-in closets, stall shower, double sinks and soaking tub. 3 additional bedrooms all with wood floors. Huge bonus room over the garage is the perfect playroom, craft room or informal hang out room. Oversized 3 car garage. A must see! Close to restaurants, shopping, hiking and antique stores. 90 miles to NYC, 15 minutes to Litchfield Center.

434 Quassapaug Rd, Woodbury
$680,000
3 Beds ⋅ 3 Baths ⋅ 24014586 MLS
Welcome to this lovely, charming home in Woodbury set on 4+ park like acres. Horse property! This property has it all....barn, inground pool, beautiful level grounds---meticulously cared for over the years. Pride of ownership is apparent both inside and out.This Cape style home, built in 1976, with only two home owners to date. Newly painted interior.Main level features a Foyer, Formal Living Room w/Fireplace+Built-ins, Formal Dining Room w/Exposed Beams, Sconces+Fireplace. Sun Room extends from the Dining Room via French Doors, w/convenient access to Deck.The Eat-In-Kitchen features a center island,custom buit-ins, fireplace and a sitting room/gathering place within the Kitchen.First floor Full Bath.Possible first office/fitness room/den/extra bedroom. The Family Room offers wall-wall carpeting+built-ins. The Upper Level offers 3 Bedrooms w/w-w carpeting+Laundry Closet. The spacious Primary Bedroom Suite features a fireplace, sittting area,full bath+several closets.The partially finished Lower Level offers:workbench area,pool table+shooting range.The park like grounds are ideal for seasonal entertaining w/large two tiered deck overlooking the heated inground pool.Pool cabana.The barn/stable, at one time filled with horses currently serves as a workshop/barn....great for the local car hobbyist, mechanically inclined, etc....Barn has electric and water. Heated workshop within barn. Central Air/Oil Heat~3 zones.New HVAC system-2023.Well/Septic. Whole house generator.

271 Quassapaug Rd, Woodbury

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