luxury properties for sale Woodbury, United States

Tucked away at the end of a quiet cul-de-sac in one of Roxbury's most desirable neighborhoods, this beautifully updated 4-bed, 3.5-bath Post & Beam Colonial offers a rare combination of privacy, character & flexibility. Exposed white oak beams, soaring 27ft ceilings, and 3 fireplaces create a warm architectural presence throughout the home, while thoughtful updates provide modern comfort and convenience. An active solar energy system helps offset utility costs and enhances long-term efficiency. Set on 3+ private acres, the property enjoys an exceptional natural backdrop with extensive undeveloped acreage beyond the rear property line, creating privacy and peaceful woodland views. Mature landscaping, a spacious deck, and a serene setting make the outdoor spaces ideal for entertaining or quiet enjoyment. The flexible floor plan includes a private in-law, studio, or home office space, ideal for today's evolving lifestyle needs. Beyond the 3,340 sq. ft. of above-grade living space, the home offers an expansive full lower level providing approximately 1,700 sq. ft. of dry bonus space ideal for storage, recreation, workshop, fitness, or future customization. An enormous walkable attic spanning nearly the entire 2nd floor footprint provides exceptional add'l storage rarely found in homes of this era.

Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

Welcome to this impeccably maintained, sprawling Colonial situated in the heart of Watertown. Boasting 4,321 square feet of living space, this home offers a perfect blend of timeless design and modern comfort. The main level features a spacious chef's kitchen complete with an island, breakfast nook and a butler's kitchen for seamless food preparation. The great room boasts a cozy fireplace and sliders leading to a back patio, perfect for indoor-outdoor living. The office/den and formal dining room are elevated with crown molding and recessed lighting, with gleaming hardwood flooring throughout the main level. A half bath and attached three-car garage complete the main floor. The upper level features four spacious bedrooms and four full bathrooms, providing ample room for every lifestyle. Outside, you can enjoy the well-manicured grounds and a private concrete patio, an ideal setting for outdoor entertaining or peaceful relaxation. Built in 2000, this property is a rare opportunity to own a home of this scale and quality in a prime location with beautiful views of the Litchfield Hills.

Meticulously maintained and privately set on 1.8 acres abutting protected open space, this three-bedroom home enjoys water views that shift beautifully through the seasons. Deeded access to the neighboring open space and reservoir invites fishing, kayaking, and quiet relaxing along the water. The main level's open-concept floor plan feels made for easy living, with an updated kitchen, featuring an island perfect for casual gatherings, flowing into a sunny eating area and on into a vaulted great room anchored by an impressive stone fireplace. Slide open the doors and you're on an elevated deck looking out over the water. A formal dining room, light-filled living room, laundry, and powder room complete the level. Upstairs, the spacious primary suite is a genuine retreat: private bath with soaking tub, walk-in closet, and the kind of stillness that makes unwinding effortless. The two additional bedrooms each offer flexible space for a home office, reading nook, or sitting area, and share a hall bath. The lower level adds finished space with a full bath, ready to become a guest suite, home gym, or media room. Secluded without being remote and close to everything that makes the Litchfield Hills worth calling home.

Escape to the beauty of Bridgewater, Connecticut! This completely renovated home on 2+ acres will welcome you. A stunning home from one room to the next with open space and perfect updates. The kitchen is a true show stopper. The abundant soft close cabinetry, stainless steel appliances, the granite countertop, and island create a great entertaining space framed perfectly with rich dark beams. Move to the dining room -there are walls of windows, moldings, and hardwood floors. A center staircase wraps to the living room, where a fireplace with a striking mantle centers the room. Step out to a screened-in porch surrounded by nature- a quiet brook and privacy set the mood. 4 bedrooms on the upper level, bright and spacious, hardwood, and plenty of closet space. A fully updated bath with detailed tiling is just lovely. The spacious finished attic has natural light, hardwood floors, and can be used for play space, extra beds, or an office. This special property offers a new professionally landscaped yard with a 2-car detached garage easily reached from the covered deck. Large basement with utility sink and newer mechanicals, dual AC/ heat electric system, oil furnace was replaced in January 2026, and additional storage and walkout. A favored escape spot for many, Bridgewater is unique. This home will not disappoint. Just open the door and discover for yourself how great it is to be home. Located just minutes from both Bridgewater's village center and the town of New Milford.

A custom-built Victorian reproduction in the Italianate style. Masterfully designed by it's original owners. No detail has been overlooked in this remarkable design. This unique offering is equipped with all the modern conveniences of a newer home blended with charming architectural design elements and historic, vintage charm. The first floor boasts an open floor plan with expansive custom kitchen, pantry and formal dining area with reclaimed antique fireplace with custom carved mantel and surround. The spacious living room is equipped with a second fireplace with an efficient wood-burning insert. A first floor powder room and separate den with glass french doors completes the first floor. A breezeway with custom bench and storage area conveniently connects the first floor to the three car garage area and rear patio with custom grill area and hot tub/spa. A large primary bedroom suite on the second floor is well equipped with a soaking whirlpool bathtub, a separate tiled shower stall, large vanity with double sinks and a spacious walk-in closet. Two additional bedrooms share a hall bath with a separate laundry room. Beautiful hardwood flooring and custom trim, tray ceilings, and custom moldings throughout the home. A partially finished basement of approximately 1000/sf. consists of a large family room, a large recreation room and an additional area utilized as an exercise room. Proximate to the Watertown Country Club, Rumsey Hall, and the Taft School. Please do not enter the driveway or property without an appointment confirmed with the listing agent.

Enjoy sunrises from the covered front porch and stunning sunsets from the large back deck of this 4 bedroom and 2 1/2 bath Stately Colonial in the sought after location of Town Ridge Estates. Inside you'll find hardwood floors throughout the main level with a dining room, living room, and a spacious kitchen wide open to large family room, which is anchored by a gas burning fireplace. The primary bedroom is upstairs with 2 walk-in closets, a tray ceiling, and a primary bathroom with a jet tub and double sinks. There are 3 other bedrooms and a full bathroom with double sinks. Have fun in the 700sq.ft. of finished space in the walkout lower level with your own dance floor! The two car garage is oversized to accommodate lawn and gardening items.

Story Book Setting and the house to match. Come see this beautiful home and you will not want to leave. Approach from a long gravel driveway, past willow trees and apple trees, over the brook into your private world. Custom built in 1934 and modernized to include central air, new windows, new bathrooms, and newer eat-in kitchen. The spacious living room has high ceilings, and a fireplace. The library/den has a fireplace and really cozy on cold winter days. The Florida Room brings the outdoors indoors and enjoyable most of the year. There are five bedrooms, three & half baths and plenty of closet space. The spacious primary suite has a dressing room and great closet space. This home is incredible in so many ways. Come see for yourself.

Nestled on a private, beautifully landscaped lot in the Barkwood Falls community, this charming four-bedroom, two full and one-half bath Colonial offers the perfect blend of comfort, style, and lake community living. The inviting main level features a spacious eat-in kitchen with granite countertops and tile flooring, a formal dining room, a cozy family room with a fireplace, and a sun-filled sunroom with pellet stove and vaulted ceilings that brings the outdoors in. Upstairs, you'll find a spacious primary suite along with three additional bedrooms, providing plenty of room for family and guests. Outside, the grounds have been lovingly cultivated using many native species, creating a spectacular perennial display of color and texture throughout the seasons. Just steps from your door, enjoy Barkwood Falls' private sandy beach, picnic area, playground, and boat launch. Dock slips are available by waitlist for just $25 per foot, while kayak or canoe storage is only $175 per space annually. The low annual association dues of just $200 makes it easy to enjoy all the amenities this wonderful lake community has to offer. Conveniently located close to shopping, downtown, and major highways, this exceptional home offers the perfect balance of privacy, convenience, and year-round recreation.

This stately retreat in Merryall Woods is designed for gathering, comfortable living, and creating lasting memories. Set on 2.53 private acres backing directly to a land preserve, this approximately 3,700-square-foot home offers a rare sense of peace and privacy. A dramatic two-story foyer with dual staircases sets the stage for the home's thoughtfully designed living spaces. The impressive family room features soaring cathedral ceilings, Palladian windows, custom cherry built-ins, and a striking granite fireplace, creating a warm yet elegant setting for everyday living. The beautifully renovated eat-in kitchen is the heart of the home, showcasing custom cabinetry, granite countertops, and an oversized center island ideal for entertaining and casual dining. Sliding doors provide seamless access to an expansive Trex deck overlooking the tranquil backyard, with ample space for outdoor entertaining or a future pool. The main level also offers formal living and dining rooms, along with a private office featuring a closet and convenient access to a full bath, providing flexibility for a potential main-level bedroom or guest suite. Upstairs, the spacious primary suite offers a peaceful retreat with a tray ceiling, an oversized walk-in closet that functions as a dressing room, and a luxurious bath featuring a whirlpool tub, tiled shower, and dual vanities. Three additional bedrooms—two with walk-in closets—a full bath with dual vanities, and a convenient second-floor laundry room complete the upper level. Abundant storage throughout enhances both comfort and functionality.

An exceptional property with a rare convergence of historic provenance and modern excellence. This magical setting comprises a c.1777 home (once a Tollhouse), that blends 18th c. character, masterfully rebuilt in 2023. Step inside to a main floor that includes, a Kitchen, Dining Room, Parlor, Living Room & Primary BR suite including 3 FP's and a 3-season Solarium/Mudroom, Laundry room (ne' Buttery) and 1/2 BA. The Upper level has 2BR's and full bath. There are warm pine wood floors throughout. The enchanting park like setting includes, 3 parcels= 4.5ac.+-, with a pond, babbling stream, a 2-car barn-style garage with a ~400sf upper level studio incl. a sitting and sleeping area, a heated in-ground pool, well-established perennial gardens and pathways, stone walls and a gently rolling hill that borders the Land Trust. It is Connecticut pastoral perfection at its finest. WAIT!!! There's more...An opportunity to start a new, on-site business, currently, a 400 sf Antique Shop. For the collector, artisan or entrepreneur, seeking a life-work retreat or just pure tranquility. This is a one-of-a-kind property with incredible flexibility, delivering, history, beauty & endless possibilities, it is an extremely RARE opportunity. Are you ready to live your next chapter! Conveniently located between the storied villages of Litchfield, Bantam, New Preston & Washington for shopping, dining, hiking, skiing, boating or just relaxing. COME HOME TO THE HILLS OF NW CT 2 hrs. to NYC This property has audio and video surveillance .

Thoughtfully designed and full of rustic charm, this three-bedroom home is tucked away on 2+ acres between New Preston and Kent and is close to everything, yet wonderfully removed. Fine craftsmanship is evident at every turn: exposed post-and-beam framing, wide-board floors that warm with age, handsome fieldstone stonework, and custom cabinetry throughout lend the home an authenticity that's hard to replicate. The first floor is anchored by a chef's kitchen outfitted with a soapstone farmhouse sink, Viking range, and a large island with seating - a natural gathering place for family and friends. The space opens into a living and dining area with woodstove, and French doors lead out to a covered porch and wraparound deck that looks out over a sweeping open meadow and the garden below. Back inside, a cozy den with a fireplace invites quiet evenings, while a light-filled room could serve comfortably as a home office. Upstairs, a spacious primary bedroom offers a private bath, with two additional bedrooms sharing a hall bath. The property rounds out with a detached 500+ square foot workshop, equally suited as an artist's studio or private office, along with a garden shed and basketball court. A rare offering where craft, character, and countryside come together.

Nestled on 2 peaceful acres in Newtown, CT, 23 Old Green Road presents a beautifully maintained 4-bedroom, 2.5-bath Colonial retreat that exudes privacy and sophistication. Step inside this inviting residence to discover a remodeled kitchen boasting stainless steel appliances, marble countertops, and a butcher block island. French doors lead you from the kitchen to the expansive rear deck with built-in seating, offering the perfect setting for outdoor gatherings. The main level also features a cozy family room with a wood fireplace, a dining room with a bay window, a versatile living room or den with custom built-ins, and a convenient laundry/powder room with designer finishes. Make your way upstairs to find the primary suite, complete with a wood-burning fireplace, barn doors, custom closets, and an updated bath featuring elegant marble finishes and a rain shower. Three additional bedrooms provide flexible space for guests, a home office, or daily living needs. The property also includes a walk-up attic and a full basement with interior and garage access, offering ample space for hobbies, a workshop, a home gym, or storage. This Colonial gem has undergone major upgrades, including Central A/C installation in 2026, a high-efficiency System 2000 boiler added in 2025, rebuilt chimney with new flue liners, additional attic and basement insulation, upgraded electrical system, and a professionally painted exterior with a warranty. Additional highlights of this residence include recessed lighting, dimmers, fresh paint, upgraded closets, an epoxy garage floor, a security system, rebuilt front steps, new porch columns, beautifully landscaped grounds, a paver walkway, gravel patio, and fenced garden - all contributing to a welcoming outdoor space for relaxation and entertainment.

Discover exceptional country living in this updated vintage colonial set on a sprawling 2.5 acre private lot. This charming home is the perfect blend of classic architecture with modern amenities. Enjoy expansive outdoor space with a stunning stone heated pool and wonderful covered patio great for relaxation or entertaining. Inside the home boasts spacious living areas enhanced by large bay windows that flood the home with natural light, crown moldings, and hardwood floors. The main level includes both a living and family room each with its own fireplace, a large country kitchen, formal dining room and additional room on main level with full bath for office or au pair suite. The upper level features a primary suite complete with full bath, three additional well-appointed bedrooms, full bath, and laundry room. A standout feature of the upper level is the sleeping porch; this unique space is designed for relaxing and enjoying the outdoors while overlooking the scenic property. Convenient location to all that Brookfield has to offer! Shopping, restaurants, schools, parks, lakes, and easy access to the highway.

Set along a quiet ridgeline with long views over the surrounding countryside, this home offers a sense of privacy and space that's hard to find. A winding driveway leads you through manicured grounds to a timeless facade. Inside, the layout feels both open and purposeful. A two-story foyer and sweeping staircase create a strong first impression, while hardwood floors and custom millwork carry throughout the home. The main living areas connect easily; there's a formal dining room with a fireplace, a butler's pantry for added convenience, and a well-designed kitchen that opens to a casual dining area and a comfortable family room with a stone fireplace. The living room is lined with windows, bringing in natural light and framing the distant views. Built-ins add character and function, and the space extends to a covered porch, an easy spot to unwind. A main-level guest suite with its own entrance offers flexibility for extended family, guests, or a home office setup. Upstairs, you'll find four spacious bedrooms, including a primary suite with a sitting area, private balcony, and a spa-like bathroom with soaking tub and glass-enclosed shower. Outside, the stone patio creates a natural gathering space for entertaining or simply enjoying the setting. The grounds are open yet private, bordered by protected land, and a tucked-away hot tub adds a quiet place to relax at the end of the day. This is an unforgettable home in a setting that truly stands out.

Charming 3-bedroom home offering multiple flexible spaces to fit your needs. This well-maintained home features refinished original hardwood floors, central air, a spacious mudroom/laundry room, a walk-in pantry, and a walk-up attic providing excellent storage or future potential. Enjoy outdoor living with a covered front porch and side yard patio while taking in the privacy of the wooded rear portion of the 1.3-acre property. The detached barn is ready for its next owner's vision, while ample parking adds to the property's convenience. Located in a quiet area near the Watertown line with convenient access to everyday amenities and nearby outdoor recreation.

If you like the idea of a tiny house but can't figure out how to downsize that much, here is your solution! This adorable one room cottage in the woods has space for you and the basics, a nice usable kitchen and a full bathroom with a shower. The owners have poured a ton of love into it in the form of a brand new roof, new well, new windows, new range, refrigerator, washer & dryer, cleared the property of many trees, and put in a new well pressure tank. The furnace is on the newer side, as is the hot water heater. They put in a new bathroom sink and repaired the septic. It's cozy and comfortable, cute and ready for you! There is a total of 596 liveable square feet when the kitchen is included in the number. Explore the nearby Larkin Trail, or just relax by the stream that runs along the side of the property. The house is not connected to the sewer line in the street, but a new owner can look into that if expansion is your plan. Being sold as-is.

Nestled in the serene cul-de-sac of prestigious Hubbell Mountain Farm North, 3 Partridge Trail in Sherman, CT, offers a luxurious and carefree lifestyle in a custom Colonial home. Set on 9.24 acres of level land adorned with colorful trees and charming stone walls, this property provides a tranquil retreat with picturesque country views. The open floor plan of this 4-bedroom, 2.5-bathroom residence exudes modern elegance and vintage charm, featuring gleaming hardwood floors, French doors, and antique finishes. A spacious living room, private home office, and powder room complete the main level, while a spindle staircase leads to the primary sanctuary upstairs, offering a walk-in closet and a luxurious marble bath with Edwardian-style console sinks, The heart of the home is the gourmet kitchen, complete with a center cherry top island, sun-drenched window seat, and stainless steel high- end appliances. It flows seamlessly into the elegant dining and family room area, highlighted by a custom, dual-sided smooth stone wood burning fireplace. and a soaking tub. Additional guest bedrooms with generous closet space and a shared full bath provide comfort and style, with a convenient laundry room rounding out the upper level. The full walk-out lower level offers potential for additional living space and storage, complemented by a 3-car garage and a Generac generator for added convenience.

Nestled on a peaceful cul-de-sac in the charming town of Brookfield, 5 Bayberry Drive presents a wonderful opportunity to own a meticulously maintained 4-bedroom Colonial home on a generous 1.05-acre lot. The property boasts stunning curb appeal with professionally landscaped garden beds, a welcoming stone paver walkway, and a spacious yard offering plenty of room for outdoor activities and relaxation. Step inside this inviting residence to discover a thoughtfully designed interior spanning over 3,100 square feet. The main level greets you with a well-appointed kitchen featuring Corian countertops, tile flooring, and modern lighting fixtures. The kitchen's large peninsula provides a perfect gathering spot, ideal for entertaining friends and family. The layout flows seamlessly into multiple living areas, including a generously sized formal living room and a cozy family room accentuated by a charming brick wall and a gas log fireplace. A versatile dining room, currently used as a home office, adds flexibility to the space. Completing the main level are a convenient powder room and a laundry area for added convenience. Upstairs, the home offers four comfortable bedrooms, each adorned with gleaming hardwood floors. The primary suite is a true retreat, boasting two walk-in closets, a private full bath, and sliders leading to an expansive great room. Another bedroom also enjoys access to this versatile space, while an additional bedroom features a sizable walk-in closet. The great room, updated in 2021, offers plush wall-to-wall carpeting, fresh paint, ceiling fans, and direct access to the backyard, making it perfect for various activities such as recreation, a home gym, or a media room. A fenced area is available for pets to roam freely and safely. Recent upgrades include a new septic system (2024), water heater (2024), roof (2022), and driveway (2022), ensuring modern comfort and efficiency. An Eversource Energy audit has been conducted to enhance energy efficiency. Beyond the enchanting confines of this lovely home, residents will enjoy a location close to the serene Candlewood Lake, a convenient boat launch, local marinas, Brookfield Town Park, and Cadigan Park. The area offers a wealth of amenities, including nearby shopping destinations, dining options, and easy access to the I-84 highway, making daily errands and commuting a breeze. Don't miss this chance to own a tranquil retreat in a desirable neighborhood that beautifully blends comfort, style, and modern convenience.

Final touches of a gorgeous renovation complete this 3 bedroom and 2 1/2 bath Colonial in Litchfield, less than 1 mile to The Green. This 1914 home with a wide open floorplan and lots of natural light is loaded with character, and ready for it's new owner to move right in. The process started with stripping the walls to the studs, new wiring & plumbing, new warm air & central AC, new kitchen with Bosch appliances and bathrooms, replaced old flooring on both levels with white oak floors, new bluestone patio with a stone wall, painted inside & out, and more! The color palate is stunning, and the added wooden barn beams compliment the chic look. Outdoors enjoy the wrap around deck in front, or the recently added bluestone patio with a stone wall in the back. There's even a newly paved driveway! Savor a dinner at an award winning restaurant in town, or a glass of wine at the Abner's rooftop bar. Many take a hike on the great choices of trails throughout the area, and residents of Litchfield may use the Litchfield Town Beach at Bantam Lake. Only 2 hours to NYC and 2 1/2 hours to Boston.