Weston Homes with Weston Middle school

Welcome to Weston, Connecticut – a charming and picturesque town nestled in the heart of Fairfield County. Known for its stunning landscapes, tight-knit community, and top-tier educational institutions, Weston offers a perfect blend of suburban tranquility and vibrant living.

With a population that appreciates the finer things in life, Weston is characterized by its lush greenery, scenic parks, and beautiful homes that reflect the town’s rich history and commitment to quality living. The town's commitment to preserving its natural beauty is evident in its numerous trails and open spaces, making it a haven for outdoor enthusiasts and families alike.

One of the standout features of Weston is its highly acclaimed school system, particularly the Weston Middle School, which is renowned for its academic excellence and nurturing environment. Families looking to settle in this idyllic town will find an array of beautiful homes conveniently located within the school district, ensuring that children have access to top-tier education just a stone's throw away from their front door.

Weston’s real estate market offers a diverse selection of properties, from charming colonial homes to modern estates, catering to a variety of tastes and budgets. The community is vibrant, with local shops, dining, and recreational activities that foster a strong sense of belonging.

Whether you’re drawn to Weston for its exceptional schools, serene surroundings, or the welcoming atmosphere, this town has something for everyone. Explore the homes in Weston and discover the perfect place to create lasting memories in a community that truly feels like home.

Newest Weston Homes with Weston Middle school

$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

$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

$1,850,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ 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

$2,000,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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

$959,000

ACTIVE Status ⋅ 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

$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

$2,895,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24198358 MLS

Perfectly positioned on 2.25-acres on a private lane, this extraordinary new home, expertly crafted by Thomas Sturges Construction, offers modern luxury that embraces its natural environment. From the moment you step inside, the cohesive design & meticulous attention to detail are evident, creating an atmosphere that is as sophisticated as it is welcoming. Whether you're hosting a large-scale gathering or enjoying a quiet evening, the intuitive, effortless flow feels perfectly proportioned. Every inch reflects a commitment to quality, featuring premium finishes & a palette that feels both timeless & fresh. The culinary center of the home is a showpiece, anchored by elegant Taj Mahal quartzite countertops, Thermador appliances, a stunning center island & a spacious walk-in pantry. Each of the 5 generously sized bedrooms is thoughtfully designed as a private sanctuary with its own dedicated en-suite bath. The primary suite is a true standout, offering a spa-like experience with dual walk-in closets & a sense of calm that mirrors the property's serene surroundings. Outside, a covered patio overlooks the expansive, flat backyard - an ideal backdrop for al fresco dining or peaceful relaxation. All this just minutes from Weston's top-rated schools, the town center, the Merritt Parkway & neighboring Westport, offering the perfect blend of seclusion & convenience.

16 Katydid Ln, Weston

$1,249,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24201546 MLS

Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original architectural details and warm, welcoming spaces reflect the home's historic roots, while thoughtful updates provide modern convenience. Three renovated baths seamlessly combine classic style with contemporary finishes, while spacious living and entertaining areas offer flexibility for everyday living, gatherings with friends, and special occasions. Outdoor living is equally impressive. A spectacular solar-heated pool creates a private summer retreat, surrounded by mature landscaping and expansive grounds that enhance the property's peaceful setting. The barn is a standout feature, offering exceptional versatility with two-car garage parking, abundant storage, and exciting future potential for a finished second-floor loft, studio, office, gym, or guest space. Ideally located just minutes from the Cannondale train station for convenient access to New York City, as well as nearby shopping, dining, and local amenities, this special property offers the rare opportunity to enjoy the character and craftsmanship of a historic home while benefiting from updates that support modern living.

181 Georgetown Rd, Weston

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Weston Homes with Weston Middle school

Newest Weston Homes with Weston Middle school

How much is your home worth?

How much is your home worth?