Weston Homes for Sale

Welcome to Weston, Connecticut—a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes, top-rated schools, and a strong sense of community, Weston offers a serene suburban lifestyle while being just a stone's throw away from the vibrant energy of nearby cities like Westport and Norwalk.

Weston is characterized by its sprawling parks, charming neighborhoods, and an abundance of outdoor recreational opportunities. Whether you enjoy hiking through the scenic trails of the Devil's Den Preserve or relaxing at the serene Barlow Mountain Park, there's something here for everyone. The town's commitment to preserving its natural beauty is evident in its well-maintained green spaces and conservation efforts.

When it comes to homes for sale, Weston boasts a diverse array of properties that cater to various tastes and lifestyles. From stunning contemporary estates to cozy colonial homes, the real estate market here offers something for everyone. Many homes feature expansive yards, modern amenities, and breathtaking views, making them perfect for families and individuals alike. The sense of community in Weston is palpable, with friendly neighbors and local events that bring residents together throughout the year.

With its excellent schools, strong community spirit, and beautiful surroundings, Weston is not just a place to live; it’s a place to thrive. Explore the homes for sale in Weston today and discover your dream home in this idyllic Connecticut town!

Newest Weston Homes for Sale

$795,000

5 Beds ⋅ 3 Baths ⋅ COMING SOON Status ⋅ 24215845 MLS

This charming classic Colonial is ready to welcome its next chapter for the first time in over 50 years! Nestled on a picturesque cul-de-sac in a sought after Weston neighborhood, this home sits on two beautifully landscaped, lightly wooded acres, offering exceptional privacy and a peaceful setting. Freshly painted throughout and featuring gorgeous hardwood floors, the home is filled with timeless character and warmth. The main level offers an inviting living room and family room, each with its own fireplace, a formal dining room, a convenient first floor bedroom with a full bath, and a sun-filled sunroom overlooking the serene backyard. Upstairs, you'll find a spacious primary suite complete with a third fireplace, three additional generously sized bedrooms, a shared full bathroom, and an abundance of closet space throughout. The expansive unfinished basement offers endless possibilities, with the potential to create approximately 1,300 square feet of additional living space, and is already equipped with a CT Basement Systems drainage system. With its classic New England charm, beautiful natural surroundings, and desirable cul-de-sac location, this special property presents a rare opportunity to make a well-loved home your own.

6 Mountain View Dr, Weston

$1,475,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$812,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211308 MLS

Built on a private road this 1953 home on 2+ acres of land has a sloped frontyard and has an almost flat large backyard that is accessed by walk out doors from the finished basement segment of the full basement. The other, larger, section of the basement has the potential of further development. Since this is a private road it should be noted that the property extends up the hill on the other side of the road. Solid wood flooring runs throughout the majority of the main floor. Both fireplaces in the house are in working order, one in the living room and one in the finished section of the basement. This property is located 0.4 miles from the Trout Brook Valley Preserve (1009 acres), with its biking and hiking trails etc. Bisceglie-Scribner Park is 4.7 miles away, with its fitness trails, man made swimming pond, playground, and baseball fields. The Weston Historical & Cultural Center is 4 miles away. Known for an outstanding school system, the Weston School Complex is only 5 miles away. Major shopping areas such as Fairfiled/Black Rock (8 miles) and Westport (8 miles) are less that 15 minutes away. Add 5 minutes and you are at the beaches of Sherwood Island State Park and/or Compo Beach in Westport.

3 Trout Brook Ln, Weston

$2,250,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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! Pls note seller's lender did NOT require flood insurance due to home's high elevation.

26 Pent Rd, Weston

$1,495,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$2,999,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24206702 MLS

Welcome to an exceptional luxury retreat in the heart of Weston, where privacy, elegance, and resort-style living come together in a truly remarkable setting. Privately positioned at the end of a long driveway on a desirable cul-de-sac, this distinctive estate offers an extraordinary lifestyle with sophisticated indoor and outdoor spaces designed for both grand entertaining and everyday enjoyment. Step outside to your own private resort, featuring a gunite heated swimming pool, jacuzzi, expansive stone patio, outdoor shower and beautifully appointed outdoor entertainment area with a fully equipped outdoor kitchen. Surrounded by mature landscaping and tranquil natural beauty, the outdoor spaces create the perfect setting for al fresco dining, summer gatherings, or quiet evenings under the stars. The residence offers 5 bedrooms, 5 full bathrooms, and 3 half bathrooms, along with an impressive array of thoughtfully designed spaces, including a billiard room, wine cellar, exercise room, recreation room, office, sunroom and family room. An additional attic level offers a finished room and versatile bonus space, providing even more room for guests, hobbies, or personal use. Every detail reflects a commitment to comfort, entertaining, and refined living. A 3-car garage adds convenience and ample space for vehicles and storage. From the grand approach and peaceful cul-de-sac setting to the exceptional amenities and expansive indoor-outdoor living spaces.

32 Bernhard Dr, Weston

$649,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205703 MLS

Welcome to 38 Ravenwood Drive, a classic Cape Cod-style home set on a private 2-acre parcel in desirable Weston. Offering approximately 1,515 square feet of living space, this 3-bedroom, 2-full-bath residence features a comfortable layout with two fireplaces, central air. A standout feature is the expansive wrap-around deck, offering a wonderful outdoor setting for entertaining, relaxing, and enjoying the surrounding natural landscape. Mature trees and the generous 2-acre lot provide a sense of privacy and tranquility while maintaining convenient access to area schools, shopping, dining, parks, and commuter routes. A great opportunity to bring your vision to this well-located Weston property and create a home tailored to your lifestyle. Some images attached are virtually rendered.

38 Ravenwood Dr, Weston

$2,095,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24202562 MLS

The New Sensation! Don't miss the opportunity to see this sun drenched 4-5 bedroom Contemporary home w/ a flexible floorplan to suit a variety of lifestyles! An entertainer's dream, this home offers something for everyone. The charming entry greets you as you step into the front parlor w/ a marble surround fireplace. A stepdown into the large family/living room w/ wetbar, built-ins, fireplace & sun solarium overlooking beautiful pool & grounds. The light & bright dining room w/ sliders to a private deck also flows into the spectacular kitchen. Your friends & family will love being entertained in this fabulous space w/ huge center island w/ five burner cook top & 2 sinks, 6 burner Viking range as well as two additional wall ovens (one w/ a pizza stone), 2 dishwashers, huge side by side Subzero, walk-in pantry, fireplace, built-ins & eat-in dining area leading to multi-tiered decking & heated in ground pool and pavilion. The main level of the home also includes lovely guest quarters w/ensuite bath & large closet. The light filled sunken Primary bedroom has fireplace, walls of glass for viewing spectacular sunrises, dual walk in closets & large bath w/spa tub & walk-in shower. The 2nd floor offers 2 bedrooms w/ bath & a bonus room (playroom, music room etc).The full walkout lower level boasts pool cabana, media room,full bath, office, workout space, large cedar closet & flexible spaces for 5th BR. All of this & so much more just minutes to Weston school campus & town center!

36 Old Orchard Dr, Weston

$1,695,000

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205738 MLS

Light-filled, beautifully renovated and wonderfully versatile, this striking Weston 5/6 bedroom contemporary OFFERS OVER 5,000 square feet of living space in a private yet convenient setting. From the moment you enter, the home impresses with a dramatic great room featuring soaring cathedral ceilings, skylights and walls of windows that bring the outdoors in. Designed for everyday living and entertaining, the open, airy floor plan features two fireplaces and multiple decks for relaxing and enjoying the surrounding landscape. The renovated kitchen offers brand-new appliances, generous workspace and an easy connection to the living and dining areas. The main-level primary suite provides the ease of one-floor living, while additional bedrooms offer plenty of room for family and guests. A private space above the garage is ideal as an au pair suite, guest quarters or home office. The finished lower level adds even more flexibility with space for a possible 6th BR, recreation/media room, fitness area and kitchenette. Numerous decks overlook the beautiful private yard. Just minutes from charming Weston Center and Weston's top-rated schools, residents also enjoy beach rights at Westport's Compo Beach. A rare combination of space, style, privacy and convenience. Enjoy the best of Weston living-peaceful surroundings, award-winning schools (bus stop at end of driveway!), a welcoming town center and easy access to Westport's shopping, dining, train and beaches.

158 Steep Hill Rd, Weston

$1,550,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192647 MLS

Fully remodeled and ideally located within walking distance of the award-winning Weston school campus, this exceptional Lower Weston Colonial offers refined living in one of the town's most coveted neighborhoods. Thoughtfully expanded and redesigned with a spacious four-level floor plan, the home features six generously sized bedrooms and four beautifully appointed full baths, showcasing high-end finishes throughout. The designer kitchen is equipped with a Viking range, quartz countertops, and custom cabinetry, flowing effortlessly into bright, open living spaces centered around a striking double-sided fireplace. The luxurious primary suite serves as a private sanctuary, complete with a spa-inspired bath featuring an oversized double shower. Spacious secondary bedrooms, versatile living areas, and abundant natural light provide exceptional comfort and flexibility for today's lifestyle. Step outside to discover your own forest-like retreat. A composite deck overlooks the tranquil, private backyard, where mature trees create a peaceful setting for relaxing or entertaining. Gather around the custom stone fire pit, unwind beneath the pergola, or entertain your guests on the wrap-around deck. The finished lower level includes a spacious rec room, mudroom, and access to the attached two-car garage. Conveniently located minutes from town, Devil's Den Preserve, and approximately 12 minutes to downtown Westport.

143 Old Hyde Rd, Weston

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Weston Homes for Sale

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