Browse All Woodbury CT 3 Bedroom Properties for Sale

3 Beds ⋅ 2 Baths ⋅ 24207451 MLS

The John Cramer House at 10 Weekeepeemee Road is listed on the National Register of Historic Places and is a wonderful example of Greek Revival architecture. Rich in period character, the home features beautiful chestnut plank flooring, nearly 9-foot ceilings, and an original fireplace with a beehive oven. The first floor offers a study, living room, dining room, granite-countered kitchen, and a charming breakfast room with wood stove and half bath. Upstairs are three bedrooms, a full bath with marble counter, and conveniently located laundry. A full walk-up attic leads to a large finished space with additional storage and closet space. An attached shed provides a potting area and stairs to a second-floor loft. Set on 3.09 acres, the property also includes a historic barn with a two-car garage, two horse stalls, and a full second floor. Open field and wooded areas create a peaceful country setting, with elevated views toward the town of Woodbury from the upper portion of the property. Across the road, enjoy seasonal views of the Weekeepeemee River, adding to the charm and character of this special historic property.

10 Weekeepeemee Rd, Woodbury

$519,000

3 Beds ⋅ 2 Baths ⋅ 24203287 MLS

CHARM, CHARACTER & CLASSIC NEW ENGLAND APPEAL IN HISTORIC WOODBURY! Welcome to this distinctive 1895 Colonial farmhouse, where timeless architectural character blends beautifully with thoughtful modern updates. Offering 3 bedrooms and 1.5 baths, this inviting home is filled with warmth, natural light, and the craftsmanship that makes an older New England home so special. Step inside to discover beautiful hardwood floors, oversized windows, and comfortable living spaces designed for both everyday enjoyment and entertaining. The spacious living room provides an inviting place to gather, while the formal dining room is ready for holiday dinners, celebrations, and memorable evenings with family and friends. The updated kitchen brings modern convenience to the home's historic character with granite countertops and engineered wood flooring. An adjoining eat-in area with a woodstove that heats up to 2200 gross living area and vaulted ceiling creates an open, airy atmosphere and a wonderful place to enjoy morning coffee or casual meals. A convenient half bath completes the main level. Upstairs are three generously sized bedrooms and a full bath, providing plenty of room for a variety of living arrangements. Outside, enjoy the charm of the home's welcoming front porch, or head to the backyard where you'll find space for outdoor entertaining, gardening, recreation, or simply relaxing and enjoying your surroundings.

50 Washington Rd, Woodbury

$289,900

3 Beds ⋅ 3 Baths ⋅ 24205036 MLS ⋅ Woodlake BLDG.

Welcome to sought-after Woodlake Estates! A peaceful, resort-like community surrounded by nature and recreational amenities. This spacious Townhouse-style end unit offers 9 rooms, 3+ bedrooms, 2.5 baths, a finished basement, and a detached 1-car garage. The main level features a generous sized living room with sliders leading to your private deck, kitchen with separate dining area, convenient home office nook, and half bath. Upstairs, the primary bedroom offers its own full bath, along with two additional bedrooms and another full bath. The finished lower level provides valuable additional living space with two rooms that can easily adapt to your needs- ideal for a family room, home office, gym, or potential additional bedrooms-plus a dedicated laundry area. Newer central A/C adds peace of mind. This townhouse offers an exciting opportunity for the buyer with vision to add personal touches and updates, bringing out its full potential and building instant equity. Enjoy the tranquil setting of Woodlake Estates with scenic walking and hiking trails, a pond for canoeing and fishing, tennis courts, grove area for picnics and plenty of opportunities to simply relax and unwind on your private deck. Perfectly situated for both convenience and lifestyle with an array of fine dining and shopping options just minutes away. Enjoy easy access to major highways for commuting, only 30 mins from Danbury and less than 2 hours from NYC! Come see it before it's gone!

6 Upper Commons Unit 6, Woodbury

$699,900

3 Beds ⋅ 3 Baths ⋅ 24204212 MLS

Imagine starting your morning with a cup of coffee on the gorgeous wraparound front porch as you take in the view of Radey Pond or spending warm summer evenings entertaining family and friends in this beautiful and private setting.Situated on 2.31 acres, this charming 3/4-bedroom, 2.5-bath Cape/Colonial offers the perfect combination of classic New England character, comfortable living space, and a flexible floor plan. At the heart of the home is the spacious eat-in kitchen, offering plenty of counter and cabinet space and flowing naturally into the inviting family room with a cozy fireplace. Whether you're entertaining a crowd or enjoying a quiet evening at home, this warm and welcoming space is made for gathering.A separate living room and office/den provide additional options for relaxing, working from home, or creating a space that fits your lifestyle.Upstairs, the spacious primary suite is a true retreat with a large closet and private full bath featuring a spa tub and separate shower. Two additional generously sized bedrooms share another well-appointed full bathroom.Need even more room? The finished third floor offers wonderful flexibility and can easily become a fourth bedroom, private home office. Hardwood floors throughout add timeless appeal, while a new roof offers peace of mind.Outside, the 2.31-acre private lot and beautiful pond views create a setting that feels removed from it all, while still being conveniently located near amenities, and major highways

201 Transylvania Rd, Woodbury

$699,000

3 Beds ⋅ 3 Baths ⋅ 24200785 MLS

Some homes make their impression at the front door. This one begins long before it. Set nearly out of sight on almost three acres, the home is approached by a long driveway that opens to a circular drive and generous garage parking, a gracious arrival that feels worlds away. Inside, the floor plan delivers more than expected: a sunlit living room, formal dining room, updated white kitchen with breakfast space, and a generous family room anchored by a dramatic stone fireplace. Upstairs are three bedrooms and two full baths, while the finished walkout lower level adds a recreation room, flex room, and dedicated laundry space that can shift with the way you live. The outdoor experience is equally considered, with three distinct places to gather: a welcoming front patio, elevated rear deck, and lower-level patio leading toward the in-ground pool. Framed by bluestone, open lawn, and mature woods, the pool feels less like an amenity and more like a private summer destination. Yet this retreat is only minutes from Woodbury's Main Street celebrated for its restaurants, local shops, and antiques and close to trails and open space at Minortown Road Preserve and Orenaug Park. Private without being remote, flexible without feeling ordinary, this is a home designed for quiet mornings, effortless entertaining, and unforgettable weekends.

61 Minortown Rd, Woodbury

$589,000

3 Beds ⋅ 3 Baths ⋅ 24200605 MLS

Welcome home! The details of this home are what make it unique. From the gigantic hydrangeas to the appetizing peach and pear trees, this home will continue to exceed expectations. Inside is remodeled and immaculate with the great elasticity that so many lack. The finely scaled rooms are so versatile, the home really allows you to figure out what works for you. For instance, the dining room, could be an office, the great room a dining room, you choose. Upstairs the bedrooms are a wonderful scale and ready for you to bring your toothbrush. Downstairs, this is where it really gets interesting! Downstairs is a clean and unfinished basement AND a huge room under the addition (which could be made into an in-law with separate entrance), with a deck outside. So much potential OR just enjoy as is! This home is truly a turn-key pleasure. Must see!

323 Upper Grassy Hill, Woodbury

$309,000

3 Beds ⋅ 3 Baths ⋅ 24200604 MLS ⋅ Condos At Woodlake BLDG.

PRETTY AND SO PRIVATE!! Enjoy nature right from your back door in this spacious, freshly painted 3-bedroom home! Imagine relaxing with a cup of coffee on your private deck. Kitchen is nicely updated with large pantry, stainless appliances, dining area and ceiling fan. The living room features a warming fireplace with Pellet Stove for an economical heat source. and the dining room boasts sliders that open to the rear deck. Upstairs, you'll find three comfortable bedrooms and two full baths, plus there's an extra room in the finished lower level, perfect for office, media room or workout room. You'll love all the amenities Woodlake has to offer, like walking trails, a pond for canoeing, picnic areas, and a playground. The town of Woodbury itself is fantastic, with a wine trail, excellent restaurants, and charming antique shops to explore. Plus, it's super convenient to the highway, shops, and schools. Woodlake is such a wonderful community.

8 Woods Way Unit 8, Woodbury

$599,900

3 Beds ⋅ 2 Baths ⋅ 24194640 MLS

Exceptional value and opportunity on 3.5 gorgeous acres! Bring this home back to its original charm. Features hardwood floors throughout and a cozy front porch. The upper level includes 3 bedrooms, a full bath, and access to a walk-up attic from the primary bedroom. The main level offers a half bath and a functional, open layout. Additional property highlights include a separate 962 sq. ft., 2-bedroom guest house-offering incredible potential for an in-law suite or rental income once renovated (appears to be separately metered). The property also features two massive, 2-story barns that appear to have electricity. Tremendous upside potential for an end-user, investor, or multi-generational living. Subject to probate approval. Property sold as-is; no disclosures.

153 Old Sherman Hill Rd, Woodbury

$695,000

3 Beds ⋅ 3 Baths ⋅ 24197319 MLS

Turn-key elevated ranch with in-ground pool, and immaculate grounds. Set on 1.6+ park-like acres, this modern ranch includes 3 bed/3 full baths, a 3-season screened porch, and a heated 20x40 pool with an oversized concrete patio. The living areas and recently renovated eat-in chef's kitchen shine with custom island, top-of-the-line appliances, and a dedicated butler's pantry with sink, wine fridge, and shelving. From the kitchen, enter the dedicated dining room with custom built-ins which open to the vaulted great room with floor-to-ceiling stone fireplace and locally sourced reclaimed mantle. Doors open out to a new composite deck overlooking the private, professionally landscaped grounds with overflowing hydrangeas, Japanese maples, and fruit trees. The primary suite features a custom cedar walk-in closet and en-suite bath. Two additional bedrooms and updated full bath provide comfortable living for family and guests. A secondary sunlit living room with an efficient pellet stove adds cozy warmth which opens out to a 3-season porch. The finished lower level includes a full bath and versatile space - perfect for a gym, media room, or flex space. Outside, enjoy true resort-style living around the fully fenced pool complex. Additional exterior highlights include a horseshoe pea gravel driveway, 4 y.o. architectural roof, new pool pump/filter and two storage sheds. Located just minutes to Woodbury's historic town center, fine dining, and boutique shopping!

39 Hard Hill Rd, Woodbury

$329,900

3 Beds ⋅ 2 Baths ⋅ 24195376 MLS ⋅ Woodbury Place BLDG.

Move right into this beautifully updated 3-bedroom, 2-bath townhouse offering style, comfort, and low-maintenance living. Gleaming hardwood floors flow throughout the home, complemented by vaulted ceilings, a skylight providing abundant natural light. The updated galley kitchen features tasteful tile backsplash and efficient design, opening to a spacious living and dining area highlighted by a cozy electric fireplace and ceiling fan. Sliding glass doors lead to a private patio with peaceful ideal setting for morning coffee, birdwatching, entertaining or simply relaxing. A convenient outdoor storage shed adds extra functionality. The main level offers two generously sized bedrooms with ample closet space, a full bath a including washer and dryer closet. Upstairs, a dramatic open loft overlooks the living area and leads to a spacious primary suite featuring a unique barn-door closet, walk-in closet, and an updated full custom tiled shower with double vanity, skylight and elegant cabinetry. Wake up to seasonal lake views from the primary bedroom suite. Central Air & updated blown in insulation are just some additional perks. A detached two-car garage provides additional storage and convenience along with an additional dedicated parking space. Ideally located with easy access to I-84, charming shops, a plethora of dining and so much that Southbury and Woodbury have to offer. This exceptional home combines comfort, convenience, and scenic surroundings in desirable Woodbury Place.

22 Woodbury Pl Unit 22, Woodbury

$1,395,000

3 Beds ⋅ 3 Baths ⋅ 24192284 MLS

Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

$525,000

3 Beds ⋅ 2 Baths ⋅ 24189460 MLS

Well maintained and updated Raised Ranch 3 bedroom 1.5 bathrooms home ready to move in! Open concept living room/dining room and kitchen that opens on to a gorgeous 12'x30' deck overlooking a beautiful fenced in backyard in the woods make for a very private setting. This home has all new windows, a newly updated kitchen with stainless steel appliances and granite countertops, finished lower-level ideal for home office or living space with plenty of natural light, windows and recessed lighting. Cutting edge solar panels save on electric bill! Conveniently located close to all amenities, shopping, dining, and major highways. Enjoy all that Woodbury has to offer - rated best town by Yankee Magazine. "Sold as is condition" a must see!

212 Upper Grassy Hill, Woodbury

$349,500

3 Beds ⋅ 3 Baths ⋅ 24191489 MLS ⋅ Woodlake BLDG.

Welcome to Woodlake! Move right in and enjoy the space, comfort, and lifestyle this beautifully maintained 3-bedroom, 2.5-bath townhouse has to offer. The light-filled and flexible floor plan includes spacious main-level living, 2 generous upstairs bedrooms, and a huge finished walkout lower level with an additional room perfect for a home office, gym, or hobby space. Updates and improvements are too numerous to mention. Highlights include an electric fireplace insert, a cozy wood stove, and a beautifully renovated upstairs bath with a jetted tub. (Ask your Realtor for a full list.) A large unfinished basement area provides abundant storage. Outside, enjoy a meal or coffee on your private deck, and you'll even enjoy the short scenic walk from your car (1 carport and 1 assigned parking spot!) to your front door. Life at Woodlake is about more than the home. Enjoy walking trails, a tranquil pond for canoeing, picnic areas, a playground, and a peaceful setting surrounded by nature. Just minutes away, historic Woodbury offers exceptional restaurants, charming shops, antique stores, New Morning Market, Flanders Nature Center, Earth Tones Native Plant Nursery, and easy access to I-84, giving you the perfect blend of country charm and everyday convenience. As an added bonus, Woodlake is FHA-approved and pet-friendly. Schedule your private showing today and experience everything Woodlake has to offer.

4 Alder Court, Unit 4, Woodbury

$679,900

3 Beds ⋅ 3 Baths ⋅ 24190540 MLS

Charming and full of character, this beautifully maintained three-bedroom Cape offers the perfect blend of comfort, warmth, and convenience in the heart of Woodbury. Set on a picturesque property with mature perennial gardens and a fenced-in yard, the home feels peaceful and private while being just a two-minute walk from downtown shops, restaurants, the library, schools, community center, and nearby hiking trails. Inside, hardwood floors and abundant natural light create a warm and inviting atmosphere. The welcoming living room features a fireplace, while the bright south-facing sunroom provides a relaxing space to enjoy throughout the day. The dining room includes a charming corner cupboard that adds timeless New England character. The finished lower level offers flexible space for exercise, hobbies, or creative pursuits and includes a sauna, shower, and fully equipped darkroom. Additional highlights include a two-car garage and beautifully landscaped outdoor spaces. A rare opportunity to enjoy distinctive features, exceptional charm, and an ideal in-town location in one of Litchfield County's most desirable communities.

31 Mountain Rd, Woodbury

$415,000

3 Beds ⋅ 3 Baths ⋅ 24099709 MLS

Nestled in the highly desirable town of Woodbury, this charming Cape offers just over 2,000 square feet of comfortable living space with endless potential. The home features 3 bedrooms, 2.5 bathrooms, and beautiful hardwood floors throughout. A dedicated home office with custom built-in shelving provides the perfect space for working from home or studying. The inviting living room includes a cozy pellet stove, creating the perfect gathering space. The bright dining room features a large picture window that fills the space with natural light. A spacious mudroom with vaulted ceilings, laundry hookups, and a large walk-in pantry provides exceptional everyday convenience. Step outside to enjoy the 1.5 acre private setting, complete with an in-ground pool and safety fence-ideal for relaxing, entertaining, or making the most of New England summers. Whether you're looking to restore its original charm or add your own personal touches, this home presents an excellent opportunity to build equity in one of Litchfield County's most sought-after communities. New windows, siding and gutters in 2024. The property is being sold "as is." Priced to sell! Don't miss your chance to make this Woodbury property your own!

241 Hoop Pole Hill Rd, Woodbury

$819,000

3 Beds ⋅ 2 Baths ⋅ 24182784 MLS

Live Stress-Free in This Income-Producing Equestrian Retreat! Enjoy the best of country living while generating income from your property. Rental revenue from a separate 1 BR apartment and 4 of the 10 horse stalls offers a rare opportunity to offset ownership costs! Situated on 5.76 level acres of open pasture and riding space, this equestrian property is ideal for horse enthusiasts, trainers, or anyone seeking a peaceful rural lifestyle. The horse facilities include 4 barns with a total of 10 stalls, 2 wash stalls, and a 20 x 60-meter riding arena with premium stone dust and sand footing. The grounds offer ample space for turnout, training, recreation, and relaxation, creating the perfect balance of functionality and tranquility. At the heart of the property is a charming 3-bedroom, 2-bath ranch home featuring a windowed kitchen, spacious dining room for entertaining, vaulted ceilings, 2 fireplaces with wood stoves, a WIC, and an oversized lower-level bonus room. Step outside to a private backyard designed for gatherings and enjoyment, complete with a thriving vegetable garden. The 1 BR apartment is currently rented, but can easily serve as an in-law suite or guest quarters. There is also a 3 car garage for the car enthusiast! The possibilities are endless! The present owners, Serenity Farm Horse Rescue, have lovingly cared for this property for years. As their rescue continues to grow, they are seeking a larger facility to support their expansion. Shown by private appt.

92 Minortown Rd, Woodbury

$286,000

3 Beds ⋅ 3 Baths ⋅ 24176300 MLS ⋅ Woodlake BLDG.

At Woodlake, you're not just buying a home, you're buying a lifestyle. From being FHA Approved condos, to water views at every balcony, trail walks to boat rides to fountains and everything in between, Woodlake truly offers the peaceful, serene setting that we all dream of. This 3 bedroom, 2.5 bath freshly painted end unit has endless possibilities. Need a main level bedroom or office? One can be accommodated. Need a lower level with a separate entry or a workshop? No problem. Want a parking spot right next to your unit? This home has it. Whatever your needs are, 19 Clubhouse drive delivers. Make an appointment to see this diverse unit today! 2 pets allowed per unit.

19 Clubhouse Dr Unit 19, Woodbury

$645,000

3 Beds ⋅ 3 Baths ⋅ 24165212 MLS

QUAIL RUN On the cul de sac - 4 NEW HOMES ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy and BEAUTIFUL! Construction has begun on 2 homes with anticipated completion in August. #94 is a 3 BR, 2.5 BA FARMHOUSE STYLE SPLIT LEVEL with large front porch, oversized 2 car garage, CATHEDRAL LIVING ROOM and finished lower level with laundry room and half bath.

94 Quail Run Rd, Woodbury

$765,000

3 Beds ⋅ 3 Baths ⋅ 24159088 MLS

QUAIL RUN On the cul de sac - 4 NEW HOMES ALL ON FLAT LOTS! They might be what you have been looking for - SMALLER & SMARTER new homes with PRICES TO MATCH. Beautiful 1 acre+ lots on shared common drives surrounded by 12 ACRES OF PRIVATE OPEN SPACE. This is QUINTESSENTIAL WOODBURY - Quiet, woodsy, and BEAUTIFUL! Construction has begun with completion possible in early October. #86 is a 3 BR, 2.5 BA Cape with FULL FRONT PORCH, 2 car attached garage and OPEN BUT LIVABLE floor plan. LL set up for future finishing.

86 Quail Run Rd, Woodbury

$499,999

3 Beds ⋅ 3 Baths ⋅ 24162836 MLS

Experience the charm of this classic Cape Cod style property, featuring 3 bedrooms and 2 cozy fireplaces that invite warm gatherings on 1 acre of land perfect for outdoor enjoyment. This country eclectic home blends timeless architecture with modern comfort, offering a serene retreat that captures the essence of country living. Whether you're relaxing by the fire or exploring the great outdoors, this property promises a welcoming and tranquil lifestyle.

110 Brushy Hill Rd, Woodbury

$999,900

3 Beds ⋅ 3 Baths ⋅ 24146826 MLS

Discover the charm of this beautiful antique home in the heart of Woodbury! Nestled on the serene Middle Quarter Road, this vintage gem is being restored by the current owner and is just a 2-minute stroll from coffee shops, top-notch restaurants, and the historic Main Street. The home will be meticulously updated from the ground up, featuring wide board antique flooring, a stunning great room with a cathedral ceiling and fireplace, and formal living and dining rooms, each with its own fireplace. Upstairs, the primary suite boasts a vaulted ceiling with exposed beams, accompanied by two additional bedrooms and a walk-up attic. This will be a brand new house when complete; new mechanicals, new insulation, new wiring, new plumbing, new kitchen and baths - a new home with the charm of old. The exterior could be equally impressive, offering two post-and-beam barns, and a beautifully landscaped level lot. The Middle Quarter zoning adds extra versatility, allowing you to run a business from home and even expand the living space into the barns. This is truly one of the best locations in Woodbury!

27 Middle Quarter Rd, Woodbury

$1,450,000

3 Beds ⋅ 3 Baths ⋅ 24139312 MLS

Open Meadow Farm, a beautifully maintained property offering a blend of rural charm and modern conveniences. Set on 9.88 picturesque acres, this property features three fenced fields, ideal for horses or other livestock and a two-story barn equipped with four stalls, a tack room, gravel storage area and a gleaming concrete main floor. Recent updates include a paved driveway with turnaround, back patio, new heating system, a powerful 20KW whole house generator and four energy efficient mini-splits ensuring year-round comfort. Enjoy the beautifully landscaped gardens, several tranquil ponds, a babbling brook and perennial flower beds. This spacious home boasts three bedrooms and three full baths, a well-appointed kitchen, office space, a full basement and both attached and detached garages. Relax on the screened porch overlooking the ponds and bring your four-legged friends-this property is ready for you to move right in. Come enjoy the charming little town of Woodbury, only 90 minutes to NYC

819 Main St N, Woodbury

$990,000

3 Beds ⋅ 2 Baths ⋅ 24086595 MLS

To be built Modern style home with gorgeous southern views and privacy from your neighbors. Enjoy the wall of glass overlooking a bluestone patio, and beautiful views above Main Street North! Just a few minutes from Woodbury's town center, this home provides an open floor with a kitchen/great room, a cathedral ceiling, and a floor-to-ceiling masonry fireplace. The first floor includes a primary suite and two other bedrooms while the upper level offers an office and a loft, both with a cathedral ceiling and views to the outside.

523 Main St N, Woodbury

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