Weston Real Estate

Welcome to Weston, Connecticut—a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes and charming New England ambiance, Weston offers a unique blend of tranquility and community spirit that makes it an ideal place to call home.

With its lush greenery, rolling hills, and serene environment, Weston is a nature lover's paradise. The town is dotted with parks and nature reserves, including the stunning Bisceglie-Scribner Park and the expansive Weston Town Center, where residents can enjoy walking trails, picnic areas, and recreational facilities. The scenic beauty is complemented by a rich tapestry of history, with historic homes and landmarks that tell the story of this quaint town.

Weston boasts a strong sense of community, with friendly neighbors and a variety of local events that foster connection and camaraderie. The town is renowned for its top-rated schools, making it an attractive option for families seeking quality education for their children. With a low student-to-teacher ratio and a commitment to excellence, Weston’s educational institutions are a cornerstone of the community.

For those who appreciate the arts and culture, Weston is home to a vibrant local scene, featuring galleries, theaters, and seasonal festivals that celebrate the creativity of its residents. Additionally, its convenient location allows for easy access to nearby urban centers like Westport and Norwalk, offering a perfect balance of suburban tranquility and city amenities.

Whether you’re looking to buy your first home, a spacious family residence, or a serene retreat, Weston, CT, promises a lifestyle filled with charm, community, and natural beauty. Discover your perfect home in Weston today!

Newest Listings in Weston

$795,000

5 Beds ⋅ 3 Baths ⋅ 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

$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

$710,000

4 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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 ⋅ 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

$1,850,000

5 Beds ⋅ 6 Baths ⋅ 24197426 MLS

*THANK YOU FOR YOUR INTEREST: SELLER REQUESTS HIGHEST/BEST OFFERS BY 5PM MONDAY 9/28/26* Set on a premier cul-de-sac across from the beautiful grounds of the prestigious Aspetuck Valley Country Club, this gorgeous all-brick Colonial makes a spectacular first impression. A new circular driveway through the landscaped 2 acres leads to this architecturally distinctive custom home. Varied roof lines, bay windows, copper accents, distinctive chimneys & established landscaping set the tone for this refined home. Double doors lead to the sun-filled foyer w/floating staircase, powder rm & walk-in coat clst. Many rms feat. soaring cathedral-height ceilings, incl the LR & fam rm, each w/ fpl & oversized windows. DR w/tray ceil. Updated EIK w/fresh white cabinetry & new appls incl dbl ovens has a breakfast area w/bay window & garden views, plus a mudroom leading to the 3-car garage. The exquisite library/office has a cathedral ceil, 3rd fpl, cstm built-ins & bay window. 5 BR (4 per town) beginning with a main level guest/in-law/staff/den w/adjacent full bath. Upstairs, an open & gracious landing leads to lrg BRs. The primary suite is a stunning space with king-size BR, sitting nook, glorious windows, a lrg marble bath, walk-in clst & two extra storage spaces. The finished lower level w/high ceilings has a rec/play room/gym area, wet/snack bar, full bath and massive storage rooms or space for additional future finishing. The stone terrace leads out to level lawns and enchanting gardens.

10 Weddington Ln, 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!

46 Valley Forge Rd, Weston

$2,999,000

4 Beds ⋅ 6 Baths ⋅ 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

$959,000

24205345 MLS

Welcome to Hills End Lane, an exclusive enclave of distinguished estates just minutes from Weston's charming town center. This exceptional 2.53-acre property presents a rare opportunity to create a custom residence in one of Weston's most desirable settings. The level, lightly wooded site offers privacy and natural beauty, with 50 feet of road frontage and approximately 0.9 acres of protected wetlands and watercourses. The property is septic-approved, meets town setback requirements, and has received Inland Wetlands Commission approval. A proposed pool site further enhances the property's design possibilities. Underground gas, electric, and cable are available at the street. Renowned for its exceptional schools, scenic trails, and convenient access to Westport and the Merritt Parkway, Hills End Lane offers an extraordinary setting to bring a distinctive vision to life. Agent is Owner.

10 Hills End Ln, Weston

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Weston Real Estate

Newest Listings in Weston

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