Browse All Woodbury CT Properties with Pool for Sale

3 Beds ⋅ 3 Baths ⋅ 24209744 MLS

Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe

24 Roxbury Rd, Woodbury

$2,149,900

5 Beds ⋅ 5 Baths ⋅ 24209591 MLS

Set well back from Weekeepeemee Road in one of Woodbury's finest locations, this exceptionally well-built Colonial offers approximately 5,900 square feet of thoughtfully designed living space. Multiple bedroom suites and an open floor plan provide room for everyone, with inviting spaces for both everyday living and entertaining. The beautiful kitchen opens to a covered porch overlooking an expansive patio and gunite pool, creating a seamless connection between indoor and outdoor gatherings. Car enthusiasts will appreciate the remarkable garage and barn space. An attached, heated three-car garage is complemented by a lower-level garage with room for several additional vehicles. An impressive detached barn, constructed with steel and concrete, accommodates another six to eight cars and features heat, a half bath, glass garage doors, and both upper- and lower-level access. Outside, meticulous landscaping and a paved driveway enhance the setting, while a spacious front patio provides the perfect spot to enjoy the sunsets. An open meadow offers room for outdoor celebrations or potential equestrian use. With its generous living spaces, exceptional vehicle storage, and beautifully maintained grounds, this distinctive property offers far more than the ordinary.

348 Weekeepeemee Rd, Woodbury

$875,000

3 Beds ⋅ 3 Baths ⋅ 24209527 MLS

Welcome to history, charm, and an incredible location-the best of both worlds! Tucked along a quiet side road, this lovingly cared-for antique offers a peaceful, private setting with a picturesque waterfall nearby, yet is within walking distance to an amazing collection of local favorites, including fine restaurants, diners, a brewery, pub with live entertainment, and French bakery. No wonder they call it "Food-bury!" A stone path leads to a beautiful stone landing and a home filled with warmth and character. The spacious L-shaped living room offers two inviting gathering areas-one centered around a wood-burning fireplace with room for a grand piano, and the other warmed by a woodstove beside a full-wall library and second seating area. Just beyond is a sun-filled, beamed room wrapped in windows on three sides, perfect for breakfast, reading, art, TV, or simply enjoying the view. The charming country kitchen is exceptionally appointed with premium Viking, Miele, Sub-Zero, Dacor and Fisher & Paykel appliances, including an induction cooktop, wall and speed ovens, warming drawer and 2-drawer dishwasher. Thoughtful details include Waterworks fixtures, a pot filler, custom pull-out cabinetry and under-cabinet lighting. Two staircases lead to three restful bedrooms and two beautifully renovated full baths. The primary bath features a Waterworks vanity with quartz top and Waterworks hardware, while the second bath creates a spa-like retreat with a soaking tub and steam shower.

2 Pomperaug Rd, Woodbury

$195,000

2 Beds ⋅ 1 Baths ⋅ 24209657 MLS ⋅ Town In Country BLDG.

Welcome to 229 Bacon Pond Rd Unit 312 - located in the Town In Country complex, this 2 bed/1 bath unit has been remodeled from top to bottom featuring a brand new kitchen, new flooring, and central air. Inside you'll find an open floor plan perfect for entertaining - the kitchen has been completely redesigned featuring new cabinets, quartz countertops, and stainless steel appliances. The modern flooring flows from the kitchen to the fireplace, offering a perfect place for family gatherings. Around the corner you'll find two bedrooms and 1 full bath - the bathroom has been updated and modernized featuring a brand new vanity and tiled shower. The slider door leads to a private patio which is just a short walk down to the in ground pool. Enjoy everything Woodbury has to offer - Rt. 6 is minutes away offering plenty of restaurants and shopping, with I84 just a short drive away. Whether you enjoy laying by the pool or hiking through a number of trails this is the perfect location for the discerning consumer.

229 Bacon Pond Rd Unit 312, Woodbury

$800,000

4 Beds ⋅ 3 Baths ⋅ 24208716 MLS

A Place Where Home Feels Like A Getaway Welcome to 69 Nonnewaug Road, where peaceful country living meets the charm of Woodbury! Set on approximately 9.47 acres, this 3-bedroom, 3-bath home offers an incredible combination of space, privacy, and outdoor living. Surrounded by beautiful natural scenery, the expansive property provides plenty of room to spread out, explore, garden, entertain, or simply enjoy the peaceful setting. Spend warm summer days relaxing by the pool, host gatherings with family and friends, or unwind and take in the privacy of your own country retreat. Inside, the home offers a comfortable and inviting layout with three bedrooms and three full baths, providing plenty of space for everyday living and guests. But the lifestyle extends well beyond the walls-with nearly 10 acres and your own pool, there's plenty of opportunity to enjoy the property throughout the seasons. Located in the charming town of Woodbury, known for its quintessential New England character, historic appeal, local shops, restaurants, and picturesque countryside, this home offers a wonderful balance of privacy and convenience. If you've been dreaming of more land, more privacy, and a place where home feels like a getaway, 69 Nonnewaug Road is one you won't want to miss!

69 Nonnewaug Rd, Woodbury

$209,900

2 Beds ⋅ 1 Baths ⋅ 24206004 MLS ⋅ Town In Country BLDG.

Move right into this beautifully renovated upper end unit in Woodbury's desirable in-town Town & Country condominium complex. Tastefully updated throughout, this light-filled unit features an open floor plan with a completely renovated kitchen flowing into the living room with fireplace and built-ins. Updates include new windows, luxury vinyl plank flooring, interior doors, lighting, switches, outlets, and electrical finishes throughout. Ideally located toward the rear of the complex, the unit overlooks the pool and landscaped grounds, offering a peaceful setting with added privacy. One of the standout units in the complex, this turnkey property combines quality updates, an excellent location, and the convenience of being within walking distance to shops, restaurants, and everything historic Woodbury has to offer.

229 Bacon Pond Rd Unit 313, Woodbury

$1,100,000

4 Beds ⋅ 5 Baths ⋅ 24202077 MLS

From the moment you pull up to this House on the Hill, you will feel right at home. Built when homes were designed for gracious, comfortable living, it feels elegant yet relaxed, filled with color and thoughtful character. The beautifully crafted floor plan offers intimate parlors, three fireplaces, a generous kitchen, spacious living and dining areas made for gathering, charming Dutch doors, a cozy den, well-proportioned bedrooms, and an exceptional laundry room conveniently located on the same level as the recreation room with its own fireplace. Outdoors, a pool, professionally designed gardens, a growing room, and welcoming terraces create a setting to be enjoyed for generations. Every detail reflects a deep understanding of what makes a house feel like home. This seller is motivated!

90 Sage Rd, Woodbury

$299,000

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

$1,600,000

4 Beds ⋅ 3 Baths ⋅ 24199540 MLS

Turnkey Equestrian Facility on 21 Acres. A rare opportunity to own a fully operational equestrian property offering the perfect blend of functionality, comfort, and income potential. Set on 21 acres, this established working horse boarding facility features 21 stalls, a heated indoor riding arena with viewing area, heated tack rooms, two wash stalls, private storage lockers, two outdoor riding arenas, and newer RAM fencing throughout the property. The spacious 4-bedroom Colonial offers comfortable living with a primary suite featuring its own fireplace, two additional fireplaces with woodstoves, and a screened-in porch overlooking the property. The home provides plenty of space for both everyday living and entertaining. Adding even more versatility is the 2-bedroom apartment above the garage, ideal for a barn manager or helper, guest accommodations, or additional rental income. Whether you're looking to continue the existing boarding operation, create your own private equestrian retreat, or take advantage of the property's multiple income-producing possibilities, this exceptional horse property is ready to welcome its next owner. Agent owner.

138 Minortown Rd, Woodbury

$510,000

2 Beds ⋅ 3 Baths ⋅ 24188214 MLS ⋅ Woodbury Hill BLDG.

Welcome to beautiful Woodbury, CT! Beautiful 2 BR, 2 1/2 bath condo in sought after Woodbury Hill Condos. Park like grounds with only 78 condos, featuring a saltwater pool and a tennis/pickleball court. Well maintained condo features the main level with a Living room with vaulted ceiling and a wood-burning fireplace, dining room w/bow window, a half bath with granite vanity, an updated kitchen w/granite counters and an eating area. Sliders lead out to an oversized private deck with awning and a fantastic view! Primary BR on main level w/full updated bath w/marble vanity, walk-in closet, and an additional slider that leads out to the deck, complete with stairs down to back yard. Upper level features an interior balcony that overlooks the living room below, has a loft and a generous sized 2nd bedroom w/walk-in closet. Lots of closets space and walk in attic eve storage as well. This level also has a full bathroom with granite vanity. Lower level features a large family room with built-ins and walk out slider to the back yard, a separate play room and a large laundry room w/slop sink. Recent updates include, new LG French Door refrigerator (3/26), new hot water heater (2025), new water pump (2025). Exterior home and deck freshly painted June/July 2026. Don't miss seeing this one!

35 Woodbury Hill, Unit 35, Woodbury

$384,900

3 Beds ⋅ 3 Baths ⋅ 24099709 MLS

INVESTORS TAKE NOTICE!! A rare opportunity to bring your vision to life in beautiful Woodbury. 3BR, 2.5 bath Cape just over 2,000 square feet of comfortable living space with endless potential. This home includes hardwood floors throughout. A dedicated home office with custom built-in shelving. Large living room with pellet stove and a spacious mudroom with vaulted ceilings, laundry hookups, and a large walk-in pantry. The property sits on 1.5 acres, complete with an in-ground pool and safety fence. 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!!

241 Hoop Pole Hill Rd, Woodbury

$1,590,000

4 Beds ⋅ 3 Baths ⋅ 24184948 MLS

It's rare to find a vintage estate tucked away from a main road, but this one sits at the end of a private lane, opening to 6.3 enchanting acres framed by stone walls, manicured gardens, and a charming vintage home. The property includes a large custom two-story pole barn, inground pool, detached three-bay garage, and an adorable potting shed. The great room flows into a kitchen with handmade cabinetry, butler's pantry, soapstone counters, and a Vulcan stove, all centered around a brick fireplace flanked by double French doors leading to a shady brick patio. Off the kitchen, a spacious screened porch surrounded with stone walls, offers a peaceful spot to enjoy the seasons. The formal living room, currently an office, boasts a light-filled five-window bay, while two front entry rooms serve as a den and library. The primary suite, in its own wing above the great room, features a private living room, full bath, sleeping area, and views of Perkins Ponds. Three additional bedrooms, accessed via a second staircase, are bright, charming, and surprisingly well-appointed with closets. The impressive barn offers tandem bays for vehicles, a heated workshop, and two upper rooms perfect for future studio spaces. Relax by the pool, take in the flowers, and enjoy the chorus of birds. POTENTIAL FOR ADDITIONAL TWO LOTS SPLIT OFF OR SECONDARY HOME TO BE BUILT. BUYERS MUST DO THEIR OWN DUE DILIGENCE.

40 Ruffin Rd, Woodbury

$775,000

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

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 24163576 MLS

Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury

$527,900

2 Beds ⋅ 3 Baths ⋅ 24179262 MLS ⋅ Woodbury Hill BLDG.

The finest condo complex in one of Litchfield Counties most charming towns! Woodbury Hill is a lovely community of townhouse style homes in a very attractive setting and features a saltwater pool and tennis/pickleball courts. #17 has seen many upgrades over the past dozen years including new windows, renovated kitchen and baths, upgraded heat pump HVAC and water heater, as well as recent paint inside. This end unit also offers an expanded deck with retractable awning and lovely backyard. Full, unfinished basement, convenient one car attached garage and abundant guest parking too. All this near Woodbury's downtown shops and restaurants!

17 Woodbury Hill, Unit 17, Woodbury

$1,790,000

4 Beds ⋅ 5 Baths ⋅ 24136657 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. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury

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Woodbury Homes with Pool

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Browse All Woodbury CT Properties with Pool for Sale

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