Weston Homes for Sale

Weston Homes for Sale

Welcome to Weston, Connecticut – a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes, charming neighborhoods, and a strong sense of community, Weston offers an idyllic setting for families, professionals, and retirees alike. With its lush greenery, rolling hills, and serene environment, Weston is the perfect escape from the hustle and bustle of city life, while still being conveniently close to major urban centers like Stamford and Norwalk.

Weston is renowned for its top-rated school system, making it an attractive destination for families seeking an exceptional education for their children. The town boasts a variety of recreational opportunities, including beautiful parks, hiking trails, and the scenic Saugatuck River, ideal for outdoor enthusiasts. The vibrant local arts scene, along with charming shops and fine dining options, adds to the town’s allure.

When it comes to homes for sale in Weston, you’ll find a diverse selection of properties that cater to various lifestyles and preferences. From sprawling estates set on expansive lots to cozy family homes in friendly neighborhoods, Weston’s real estate market has something for everyone. Many homes feature stunning architectural designs, modern amenities, and beautifully landscaped yards, providing the perfect backdrop for creating lasting memories.

Whether you’re looking to relocate or invest in a second home, Weston, CT, promises a delightful blend of tranquility and community spirit. Explore the current homes for sale and discover the unique charm that makes Weston a wonderful place to call home. Your dream residence awaits in this enchanting town!

Newest Weston Homes for Sale

8 Glen Ln, 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
3 Trout Brook Ln, Weston
$812,000
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
26 Pent Rd, 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
11 Soundview Farm, 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...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
108 Old Farm Rd, 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
10 Weddington Ln, 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 Greenlea 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
46 Valley Forge Rd, 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
32 Bernhard Dr, 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
38 Ravenwood Dr, Weston
$649,900
3 Beds ⋅ 2 Baths ⋅ 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
36 Old Orchard Dr, Weston
$2,095,000
5 Beds ⋅ 5 Baths ⋅ 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
158 Steep Hill Rd, Weston
$1,695,000
5 Beds ⋅ 4 Baths ⋅ 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
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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.

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