Browse All Woodbury CT Properties with Pool for Sale

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

$1,200,000

4 Beds ⋅ 5 Baths ⋅ 24202077 MLS

Fabulous Center Hall Colonial......Don't be one of those people who drive by and sum it up. This home was built in "The Era". The era I'm speaking of is truly the way homes used to be built. It's the way life used to be lived. It was elegant yet simple. It was colorful but not garish. In all honesty it's a home that knows the correctness of living life. The floor plan will tell you that. The construction will tell you that. The small-scale parlors, four fireplaces, large kitchen, entertaining living and dining will tell you that. Even the Dutch doors, cozy den and perfect bedrooms and the best laundry room ever created on the level of the hang out room with a fireplace will tell you that. One thing I will tell you is that the construction of the pool and professional gardens, growing room and terraces will last lifetimes. Whoever built this home had the brains and the expertise in the way to live a beautiful life. I rest my case.

90 Sage Rd, Woodbury

$549,900

2 Beds ⋅ 3 Baths ⋅ 24201487 MLS ⋅ Woodbury Hill BLDG.

Beautifully renovated and move-in ready, this stand-alone unit in the charming Woodbury Hill condominium community offers a bright, open floor plan and the convenience of first-floor living. Hardwood floors run throughout, while the expanded living room features a cathedral ceiling and dramatic floor-to-ceiling brick fireplace. The completely renovated kitchen opens to the dining room, creating an easy flow for everyday living and entertaining. Sliders lead to a private deck and small patio overlooking the backyard. The first-floor primary suite includes a walk-in closet and full bath. Upstairs, the sought-after loft provides flexible space for an office, den, or TV room, along with a second spacious bedroom and full bath. A finished lower-level room offers additional living space, while the attached two-car garage and full basement provide excellent storage. A beautifully updated home in one of Woodbury's most desirable condominium communities.

25 Woodbury Hill, Unit 25, 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

$194,900

2 Beds ⋅ 1 Baths ⋅ 24199792 MLS ⋅ Town In Country BLDG.

Welcome home to Woodbury's Town & Country community! This two bedroom, one bath unit is ideally situated overlooking the inground pool and is in the most private building of the complex. This unit offers new laminate flooring, lighting, paint, trim, new carpeting in the bedrooms and new flooring in the kitchen. The bathroom has newer vanity, tub and tile work. There is a newer condenser on the roof. Well cared for unit with tasteful improvements. There is nothing to do but move right in!

229 Bacon Pond Rd Unit 351, 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.

138 Minortown Rd, Woodbury

$199,900

2 Beds ⋅ 1 Baths ⋅ 24197977 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

$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

$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

$769,900

4 Beds ⋅ 3 Baths ⋅ 24185801 MLS

Beautifully renovated 4-bedroom, 2.5-bath ranch set on a spacious corner lot in one of Woodbury's most desirable locations. Just two streets from Woodbury's nationally recognized Main Street, this home offers the perfect combination of modern updates, comfortable living, and exceptional outdoor entertaining. The complete interior renovation began in 2023 and has recently been completed, creating a truly move-in-ready home. At the heart of the property is a stunning open-concept kitchen featuring stylish finishes and thoughtful design, seamlessly flowing into the dining area and living room-ideal for both everyday living and hosting family and friends. The private primary suite offers beautiful views of the backyard retreat, while three additional generously sized bedrooms and a fully renovated full bathroom provide plenty of space for family and guests. Every bathroom in the home has been tastefully updated, complementing the home's fresh, modern feel. Step outside to your own backyard oasis. The expansive outdoor space features a large in-ground swimming pool, dedicated BBQ area, and ample lawn space for entertaining, yard games, and summer gatherings. Whether you're hosting a crowd or enjoying a quiet evening at home, this outdoor setting is sure to impress. Adding even more versatility is the separate pool house, complete with accommodations that offer endless possibilities for guests, extended family, a home office, or private retreat.

62 Heritage Dr, 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

$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

$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

$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

$529,900

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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