Weston Real Estate

Welcome to Weston, a charming town nestled in Fairfield County, Connecticut. Known for its picturesque landscapes and tight-knit community, Weston offers a perfect blend of rural charm and modern convenience.

With its top-rated schools, beautiful parks, and a thriving arts scene, Weston is a highly sought-after destination for families and individuals looking to settle down in a peaceful yet vibrant community. The town's proximity to major cities like New York City and Stamford makes it an ideal location for commuters seeking a tranquil retreat after a busy day in the city.

Nature enthusiasts will appreciate Weston's abundance of outdoor recreational opportunities, including hiking trails, nature preserves, and scenic picnic spots. The town's rich history is reflected in its well-preserved historic buildings and landmarks, offering a glimpse into its storied past.

Whether you're looking to raise a family, retire in a serene environment, or simply enjoy the best of both worlds, Weston has something for everyone. Come and explore all that this charming town has to offer – you may just find your perfect place to call home.

Newest Listings in Weston

$1,585,000

4 Beds ⋅ 4 Baths ⋅ 24219413 MLS

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary suite offers its own stone fireplace and a luxurious bath with radiant heated floors. The kitchen is equipped with Wolf, Bosch, and Liebherr appliances. The dining room features a hidden dry bar and a glassware cabinet, with sliders to the top deck for outdoor dining if desired. Upstairs, there are three additional bedroom suites with updated baths, plus a smaller third-floor bedroom ideal for an office or flex space. The finished walk-out lower level includes radiant heat, a bedroom, a full bath, an office, a gym, laundry, and a kitchenette. Outdoors, enjoy a heated Gunite pool and spa with a bluestone patio, surrounded by serene woodland views. Additional features include the Sonos system, whole-house generator, and air purification. Minutes to town and top-rated schools, this move-in-ready retreat is ideal for weekend or year-round living.

129 Davis Hill Rd, Weston

$1,850,000

4 Beds ⋅ 5 Baths ⋅ 24216810 MLS

Exceptional Lower Weston Location | Nearly 5 Acres | Endless Possibilities A rare opportunity to own nearly 5 magnificent acres on one of lower Weston's most sought-after streets! Set amid beautiful, private grounds with a swimming pool and tennis court, 43 Kettle Creek offers an extraordinary setting for your dream country estate, just minutes from Westport. Rich in character and timeless charm, this classic 1930s home showcases original hardwood floors, a gracefully curved staircase, custom built-ins and 4 fireplaces. Sun-filled living spaces include gracious formal rooms, an inviting family room and a flexible first-floor den or bedroom with full bath. Upstairs, the primary suite features a fireplace and dressing room, complemented by 3 additional bedrooms. Bring your imagination, vision and toolbox to restore this special home to its former glory, or explore the possibilities of a fresh start with a custom-built residence on this exceptional property. With nearly 5 acres, a coveted lower Weston address and convenient access to Westport, schools and nature trails, the possibilities are as compelling as the setting. A remarkable piece of Weston real estate, ready for its next chapter!

43 Kettle Creek Rd, Weston

$2,000,000

4 Beds ⋅ 5 Baths ⋅ 24217178 MLS

Set high above the road on 2 private acres, this brand-new 2026 colonial was built to capture the view. A long stone-walled drive climbs to the home, where every front-facing window looks out over sweeping lawn and treetops. The elevated setting brings in remarkable natural light along with true privacy and quiet. The listing photos were taken with the interior lights off... that brightness you see is all daylight! Inside, over 3,600 sqft of beautifully crafted living with hardwood floors throughout. The open kitchen and family room form the heart of the home: a large quartz island with seating for four, white shaker cabinetry, stainless appliances with a professional-style range, and a sunlit dining area with sliders to a bluestone patio. The family room is anchored by a coffered ceiling and a fireplace flanked by built-ins. A front living room, separate dining area, private office, two powder rooms, and a mudroom with custom cubbies complete the main level. Upstairs, the vaulted primary suite offers a sitting area, custom walk-in closets, and a spa bath with freestanding soaking tub, double vanity and oversized glass shower with bench. Three more bedrooms include one with its own en-suite bath, plus a hall bath with double vanity and a second-floor laundry room. An unfinished lower level adds room to grow. Elevated, private, and filled with light: This is Weston at its best.

80 Old Farm Rd, Weston

$1,495,000

5 Beds ⋅ 4 Baths ⋅ 24217688 MLS

You had me at hello! Beautifully renovated with warmth and style, this is a home that welcomes you in and makes you want to stay. At its heart, a beautifully appointed kitchen with its own fireplace invites cooking, conversation and a glass of wine. Adjoining it, the spacious family room with soaring ceilings and skylights is made for movie nights and time together. A second fireplace warms the inviting living room. The four-season sunroom opens to an expansive deck, overlooking a peaceful, private setting where nature unfolds through the seasons, with a yard to play, gather and enjoy the outdoors. The primary suite offers a lovely beginning and end to each day, with a beautifully renovated bath; all baths have been thoughtfully updated. The newly finished lower level features a glass-enclosed gym and an apartment-style retreat with its own kitchen, family room, bedroom,bath and laundry ideal for au-pair, guests or extended family. Neighborhood gatherings foster friendships and a true sense of community. Enjoy Weston's natural beauty, parks, highly regarded schools and access to Westport's beaches and Longshore golf course (permits and fees apply). It's not a house... it's a home!

50 Catbrier Rd, Weston

$684,000

3 Beds ⋅ 2 Baths ⋅ 24217909 MLS

Tucked away in a picturesque wooded setting, The Treetop Cottage is a little slice of Vermont in the heart of Weston. Originally built in the 1930's and beautifully reimagined from top to bottom, this enchanting 3 bedroom retreat seamlessly blends timeless charm with modern sophistication. Thoughtfully redesigned interiors feature beautiful hardwood floors, a stunning new kitchen with custom cabinetry, sleek countertops, stainless steel appliances, and refined finishes throughout. The main level offers an inviting living room with classic brick fireplace, flexible office space, bedroom, powder room and effortless access to outdoor living. Upstairs, the primary bedroom steals the show with a magnificent, oversized glass slider that floods the space with natural light and frames breathtaking views. A beautifully renovated full bath and spacious 3rd bedroom complete the upper level. Outdoors, multiple decks invite you to embrace the peaceful surroundings, while a detached one-car garage adds versatility. Minutes from Weston center, top-rated schools, and scenic trails, this is an opportunity to enjoy the serenity of a VT escape with leaving Fairfield County. Welcome to Treetop Cottage!

494 Newtown Tpke, Weston

$700,000

4 Beds ⋅ 4 Baths ⋅ 24215266 MLS

This is very special. $7,500 per month income! 3 Units! INVESTOR'S DREAM !! AN AMAZING OPPORTUNITY IN LOWER WESTON-DIRECT SAUGATUCK RIVER FRONT VIEWS - Beautiful home with separate living spaces featuring living rooms, family rooms, dining areas, newer kitchens & baths, wraparound decks with serene river views and so much more. Beautiful hardwood floors throughout, updated bathrooms and kitchens, brand new oil tanks and heating systems separate to each unit.. This was in the past a two family configuration and still is. There is a separate large rentable office space with a full bath in the lower level, overlooking the river. Two separate units with separate front doors - with kitchens, living rooms, bedrooms, etc - in excellent shape. Freshly painted inside and outside. Could be very easily converted back to a single family home. The garage is unattached, a little separate from the house.

274 Lyons Plain Rd, Weston

$1,475,000

6 Beds ⋅ 4 Baths ⋅ 24212759 MLS

Welcome to 8 Glen Lane - a beautifully renovated home set on a peaceful cul-de-sac in coveted Lower Weston, offering exceptional lifestyle flexibility with plenty of room for family and friends. Ideally located just minutes from Weston's award-winning schools, Westport's vibrant Main Street, premier shopping, fine dining, and the NYC train, this home seamlessly blends suburban tranquility with commuter convenience. Inside, sun-filled living spaces unfold with an effortless flow. The main floor features a gracious living room and an inviting family room, both complete with fireplaces. The recently renovated kitchen and bathrooms showcase timeless design and modern functionality suited for today's lifestyle. The layout features 5 spacious bedrooms and 2 full baths on the second floor, plus an additional bedroom and bath on the main level. A flexible bonus room above the garage serves as an ideal media room, playroom, fitness studio, or private home office. Completing the property is a finished lower level and a generator transfer switch to easily keep the house powered during outages. Move-in ready and thoughtfully updated, this home offers the perfect balance of comfort, style, and location in one of Fairfield County's most desirable neighborhoods.

8 Glen Ln, Weston

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 24208616 MLS

Gorgeous & Beautifully Renovated Riverfront Retreat along the western banks of the Saugatuck River bordering nearly 1,800 acres of protected nature at Devil's Den Preserve. This Craftsman-style home offers refined living, privacy & immersion in nature. Surrounded by a wildlife sanctuary, the property is a haven for cranes, hummingbirds, an occasional bald eagle & an abundance of native bird species creates a peaceful setting that feels worlds away while remaining close to everything. Renovated with attention to detail, the home blends Craftsman character with sophisticated modern amenities. Expansive windows bring the landscape indoors with tranquil views. A two-sided fireplace provides a dramatic focal point seen from both the living room & kitchen. One of the most distinctive spaces is the Family Room, affectionately known as the "Tree House". Perched among the treetops, this special retreat offers a spectacular view, a peaceful place to read, gather & enjoy each season from above the canopy. A wrap-around deck, heated Gunite pool, hot tub & firepit create spaces for entertaining & enjoying the natural beauty of the property. Updates include Hardie Board Siding, Anderson Windows, Radiant Heated Floors, New Boiler 2018, New Indirect Water Heater 2023, Updated Gunite Pool & Patio 2025, Leaded Copper Standing-Seam Roof, Whole Home Heavy Duty Generator, Exterior EV/RV Charging Station & more!

26 Pent Rd, Weston

$1,495,000

5 Beds ⋅ 5 Baths ⋅ 24209506 MLS

Welcome to 11 Soundview Farm, a stunning contemporary residence offering a serene and private escape in one of Weston's most coveted cul de sac neighborhoods. Featuring approximately 4,500+ square feet of thoughtfully designed living space, this 5-bedroom, 4.5-bath home perfectly balances architectural flair with everyday comfort. Enjoy sun-drenched principal rooms with hardwood flooring throughout, soaring ceilings, and an effortless flow for both intimate living and grand entertaining. Delight in the comfort provided by three wood burning fireplaces and the expansive maintainance free composite exterior decking...New Roof installed 2025...Nestled on a peaceful, scenic lot surrounded by mature trees, this property delivers the ultimate Connecticut lifestyle while remaining just minutes from top-rated schools, local parks, and commuting routes. Your private sanctuary awaits!

11 Soundview Farm, Weston

$2,600,000

5 Beds ⋅ 7 Baths ⋅ 24208892 MLS

Nestled on two private acres and bordered by more than 1,700 acres of protected nature preserve, this newly constructed estate in Weston delivers an uncommon blend of privacy and craftsmanship. Five generously proportioned bedrooms, each with its own en suite bath, offer refined comfort for family and guests alike, while a three car garage with soaring ceiling height stands ready for a car lift, a rare luxury for the discerning collector. At the heart of the home, a fully custom chef's kitchen commands attention with sleek quartz countertops and a professional grade suite of Wolf and Sub-Zero appliances, framed by rich white oak flooring that flows seamlessly throughout. Thoughtfully placed built in track lighting accentuates the home's clean, architectural lines at every turn. Descend to the lower level and discover a dedicated home theater, an indulgent retreat built purely for cinematic escape. Just minutes from Branchville Train Station, this address offers effortless access to Manhattan without ever compromising the tranquility of its wooded, preserve backed setting. Offered at $2,600,000, this is new construction elevated: opulent in detail, exacting in craftsmanship, and ready to welcome its first owner.

108 Old Farm Rd, Weston

$1,299,900

5 Beds ⋅ 3 Baths ⋅ 24207576 MLS

Stunning, modern renovation on this spacious home ideally situated steps to the Westport/Weston line in a very convenient lower Weston location. The open-concept interior features soaring vaulted ceilings, generously sized rooms, a fireplace, modern glass railings, and walls of windows that fill the home with natural light. The brand new modern kitchen is designed to impress with new modern cabinetry, a large center island, and premium Thermador appliances. Newly installed hardwood floors, LED recessed lighting, fresh interior and exterior paint, new trim and new interior doors add to the stylish transformation. The main level also offers four bedrooms, including a spacious primary suite with a stunning remodeled bath featuring a double vanity, oversized shower stall and soaking tub. An additional renovated full bath and convenient main level laundry complete this floor. The expansive finished walk-out lower level provides exceptional additional living space or a perfect potential in-law/au pair. Featuring a family room with a fireplace, fifth bedroom, another remodeled full bath, large recreation room and versatile bonus room. Corner lot with large private yard and grounds. Additional improvements include a new HVAC system, Navien hot-water heater, new modern glass garage doors and front door, new Trex decking and a roof completed in 2025. Gas heat, gas hot water and city water for added convenience. Septic redone in 2009. Nothing to do but move in and enjoy.

1 Greenlea Ln, Weston

$2,000,000

3 Beds ⋅ 4 Baths ⋅ 24200625 MLS

WOW! Gorgeous MID CENTURY MODERN nestled on over 300 feet of direct Saugatuck river frontage! Enter to sweeping views of the leafy bucolic scenes of nature through the walls of glass on both levels. Light and bright white kitchen opens to lovely deck for effortless entertaining. The inviting living room has a stunning floor to ceiling fireplace for cozy fall evenings. The primary bedroom suite is complete with a spa like bathroom, walk in closet, laundry and convenient office --ALL with RIVER VIEWS. The lower level is a comfortable relaxing family room, two bedrooms and full bath with direct access to the slate patio--with RIVER VIEWS. Thru a separate entrance in the back there is a newly finished sauna and shower. The cottage has endless possibilities...home office, work out space, separate lounge area...AND of course has gorgeous RIVER VIEWS!!! Pool permit has been approved; renderings attached just steps from the new sauna/shower. A pool would be a great addition 46 Valley Forge, a stunning riverfront retreat! BACK ON MARKET NO FAULT OF HOUSE; Buyer divorce complications.

46 Valley Forge Rd, Weston

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Weston Real Estate

Newest Listings in Weston

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