The median home value in Weston, CT is $1,304,500.
This is
higher than
the county median home value of $552,700.
The national median home value is $338,100.
The average price of homes sold in Weston, CT is $1,304,500.
Approximately 86.73% of Weston homes are owned,
compared to 2.72% rented, while
10.56% are vacant.
Weston real estate listings include condos, townhomes, and single family homes for sale.
Commercial properties are also available.
If you see a property you’re interested in, contact a Weston real estate agent to arrange a tour today!
A One-of-a-Kind Connecticut Estate: "Chestnut Farm" Having changed hands just three times in over two centuries, Chestnut Farm is not just a home-it's a legacy waiting to continue. Discover the rare opportunity to own this breathtaking estate, where timeless charm and modern refinement make every day extraordinary. Step into the unparalleled charm of Chestnut Farm, a Circa 1830s Federal Colonial masterpiece that seamlessly marries historic elegance with modern luxury. Once owned by Samuel Banks, this one-of-a-kind estate has been masterfully reimagined and completely modernized in 2013 to create a retreat where every day feels like a vacation. From the moment you enter the inviting entryway, you're embraced by a sense of history and hospitality. The heart of the home-a kitchen-great-room with oyster-quartz countertops, iridescent tilework, stainless steel appliances, and a vintage pub-style bar-combines style and functionality, making it perfect for entertaining or unwinding. The media area, framed by exposed beams and a stately stone fireplace, flows effortlessly to a newly built sprawling TimberTech deck and charming stone terraces. The estate offers four fireplaces, a tranquil study-bedroom, and formal living and dining rooms designed for gatherings of any scale. The luxurious primary bedroom boasts 15-foot rustic tray ceilings, a spa-inspired bath, and vintage touches that echo timeless elegance.
A breathtaking approach off a quiet cul- de-sac leads to 3.2 private acres at 16 Equestrian Trail. Extensively renovated in 2024, this home is a blend of luxury technology and energy efficiency. Enter the two-story foyer open to elegant formal & informal spaces flooded with natural light. The casual area includes a huge new chef's kitchen & dining area with an oversized island uncompromising bultler's pantry and family room with stone fireplace. The primary suite is a luxury statement with vaulted ceiling, sunlit sitting room, private office and large walk-in closets. The lavish bath features modern finishes, soaking tub, twin vanities, steam shower and warm floor. A 900 square foot bonus room with full bath inspires guests, working at home, creative pursuits or oversized gym. The stunning grounds feature a circular drive, bluestone patios, wisteria pergola, & specimen plantings overlooking a tranquil spring fed pond. Only 7 minutes from Weston's esteemed schools, this home offers privacy just 75 minutes to Manhattan. A technology forward property with 25 KW propane generator, 13 tons of HVAC, IAQ system, commercial Wi-Fi, hardwired fire and burglar system, independent temp controls for every bedroom, Caseta programmable lighting, & 30 Zone sprinkler, all smart app controlled. Amenities include large mudroom, 8-foot doors, oak floors, radiant heat, electric pet fence, tons of storage, 4 ensuite beds, vaulted ceilings, oversized 3 car garage, foam insulation and much much more
Nestled in the heart of Lower Weston, this 4.5-acre wooded paradise offers a rare opportunity to create your dream home in a serene, natural setting. A long, picturesque driveway winds through the property, crossing a stunning custom-built bridge that welcomes you to your private retreat. The land features enchanting water elements and is surrounded by the beauty of nature, providing a tranquil backdrop for your vision. This exceptional lot combines privacy, charm, and convenience, all just moments from Weston's top-rated schools, shopping, and commuting options. Don't miss this chance to build something truly special! 45 Treadwell Lane is located on a shared driveway with 47 and 51 Treadwell Lane. The property can be found at the end of the shared driveway on the right.
You'll fall in love with this home the moment you enter the front door! The welcoming foyer opens into expansive, light-filled living spaces with walls of glass & soaring windows. The main living area boasts a dramatic living room with vaulted ceiling, walls of glass & floor-to-ceiling fireplace. The chef's kitchen offers radiant-heated floor, granite counters, SS appliances, NEW Dishwasher (2024), NEW Refrigerator (2022), a large dining area that's ideal for both casual meals & entertaining guests. The family room adjoins the kitchen & offers a partial bath & the expansive patio & private backyard are perfect for BBQ's & star gazing! On the upper level, the private, primary bedroom features a vaulted ceiling, lots of windows, walk-in closet, private balcony & the luxurious ensuite bath is a spa-like haven with steam shower & radiant-heated floor for ultimate comfort. Two add'l bedrooms, an office, a flex room & a full bath with radiant-heated floor complete the upper level. Add'l improvements include Fresh Paint in 2024/ 2021, NEW Roof (2021), NEW Boiler (2022), a NEW Well Pump & Tank (2023), NEW Bluestone Walkway (2022), NEW Driveway (2017), Refreshed Trex deck (2023), all of which enhance both curb appeal & function. This home's prime location is convenient to the revitalized, trendy downtown area of Georgetown where you will enjoy restaurants, coffee shops, grocery shopping, major roads, trains, everything! Enjoy beach rights to Westport's Compo Beach! See Virtual Tour!
Discover your own secluded haven in Weston! This exceptional 4.0-acre plot offers the perfect opportunity to build your dream home, with all preliminary work already completed. This approved building lot is ready for construction, providing an ideal backdrop for your vision. Located just minutes from Weston's top-rated schools and conveniently close to the amenities of Westport and Wilton, it offers a harmonious blend of peace and accessibility. With approval for a 5-bedroom, 4 full and 1 half bath, 5,000+ sq. ft. home, the potential is vast. Don't miss the chance to design the home you've always dreamed of in a stunning natural environment, while remaining near all essential conveniences. This shovel-ready piece of land in Weston is a rare find. Approved house plans are available upon request. The seller has received town approvals and is able to oversee the building project if preferred.
Welcome to your dream retreat in Weston - a picturesque cape with classic charm & modern elegance. This enchanting 4-bed, 2.5-bath home lives larger than it appears, w/multiple areas to gather or retreat. The heart of the home is a renovated kitchen, a chef's delight w/high-end Thermador and Bosch appliances. The adjacent living room w/dining area features a cozy fireplace, built-ins, & exposed beams, creating a warm atmosphere for entertaining. Just off the kitchen/family room, is a cozy homework nook w/fireplace and a sunroom overlooking the parklike property. The primary BR suite enjoys a private setting above the garage, while 3 additional BRs and a full bath are accessed via the main staircase. The finished, walkout lower level w/ fireplace, provides an additional 405 SF of living space. Step outside to discover a private oasis with a stunning freeform gunite pool, beautifully tiered grounds, lush landscaping, specimen trees, and a tranquil meadow. The lower yard is expansive & level, ideal for games, sports training, and has an inviting outdoor firepit, perfect for memorable evenings under the stars. Adding to the charm is a versatile barn, offering expansion possibilities. A circular drive enhances the curb appeal & welcomes you home. Centrally located, this gem is within reach of Weston's award-winning schools and a short drive to Westport's vibrant beaches, shops, & train to NYC. Embrace a lifestyle of tranquility, convenience, and fun in this charming Weston home.
Private In Town Location at the end of Cricket Lane. Quick Walk to Weston Center! Wonderul opportunity for Investor or end user to make this into their private sanctuary pied-a-terre. Quiet and peaceful location with privacy and unobstructed wood views. Property being sold AS IS. Subject to Probate Approval.
Nestled in the town of Weston, this stately Georgian-style residence sits high at the end of a long private drive. The home has a thoughtfully designed floor plan that provides an effortless flow from room to room. Whether you're hosting guests or looking for comfort, you will enjoy living here where timeless elegance is combined with modern conveniences. High ceilings create a sense of openness in every room. The eat-in kitchen with gas cooking has an island & large breakfast area with sliders to the patio. The formal spaces include a living room with coffered ceilings & a gas fireplace, and a grand dining room fit for any celebratory occasion. The sunken family room with its wood-burning fireplace is a warm & cozy space. A large study, 2 half baths, & mud room complete the main floor. Upstairs, there's an oversized primary bedroom suite, complete with a dressing room & palatial spa-like bathroom providing a private retreat for ultimate relaxation. Three more bedrooms, 2 additional full baths & a laundry room complete this level. Outdoors, sit on the patio with a tall drink & watch the amazing sunsets. The level backyard will provide any age sports enthusiast with a natural field. The lower level with high ceilings & the walk-up attic space are great options for potential future expansion. Other features include hardwood floors, 3-car garage, gas heat & central air. Potential pool site. Come & see what this beautiful home in bucolic Weston has to offer!
First time on the market! This exceptional 2.1-acre residential land nestled in a serene and private setting, provides a prime opportunity to build your dream home. The flat, buildable site is perfectly poised for a spacious house, an ADU and a luxurious pool, providing ample space for both indoor and outdoor living. Convenience meets readiness with many building essential utilities already in place, including a driveway, and a well. Underground electric in process, and gas in street. The property is a legal lot, with no wetlands in the regulated area. Septic test done and lot will efficiently accommodate a multi-bedroom house and ADU. Set back from the main road, this parcel promises tranquility and privacy, making it an ideal retreat from the hustle and bustle of everyday life. Whether you're envisioning a family estate or a peaceful getaway, this land provides the perfect canvas for your vision. Don't miss this rare opportunity to create a bespoke residence in a location that combines convenience with seclusion. Seller is an experienced developer and could manage the building project if needed.
At the end of a cul-de-sac on a private road, you will find 12 Winslow Rd! Situated on 3 acres in Lower Weston, offering both serenity and a convenient location. This home has been masterfully reconstructed with the perfect blend of contemporary and traditional design elements, spanning over 3,700 sf with 4 bedrooms and 4.5 baths. Upon entering, the foyer showcases an open concept design with natural light encompassing every room. The main level boasts a dramatic family room featuring vaulted ceilings, fireplace set on a Roman Clay background and slider doors leading to an extended deck. A spacious modern eat- in kitchen with quartz counters and vast waterfall island opens to both the dining and living room with a second fireplace, creating the optimal space for hosting. Just down the hall from the kitchen, you will find an expansive office that is perfect for the" work from home" setup. Upstairs, the primary suite boats a stone fireplace, a spa like bathroom, sitting area and 2 walk in closets. Three additional bedrooms and 2 baths complete this floor, including an "ensuite." The walk-out lower level is the perfect flex or recreational space featuring an additional 750sf+ of finished space with sliders leading to a patio. Enjoy breathtaking sunset views and tranquility from this sprawling property and outdoor living space, featuring a large deck spanning across the back of the home, patio and masonry. This is truly a must-see property!
Gorgeous new construction located in one of Weston's most beautiful and highly desirable neighborhoods (Singing Oaks). The private and wooded 3.56 acre site is situated at the end of a sunny cul de sac and has room for a pool!. This stylish 5 BR, 4 bath, 2 half bath home has an open floor plan which gives it a bright and airy feel! Meticulously constructed with custom luxury finishes and superior craftsmanship. This home has a well thought out design with living spaces that are both classic and functional. Special features include: a gorgeous chefs kitchen with custom cabinets, a large center island, high end appliances & sliders which leads to a spacious composite deck; efficient propane furnaces; a two story foyer; glass stair railings; oak hardwood flooring throughout; a light and bright 2 story family room with a gas FP (opens to the kitchen); The main level includes a generous sized dining room, an amazing mudroom off the garage w/separate powder room, a formal living room & a first floor guest bedroom with an en-suite bath. The stunning primary bedroom suite features dual walk-in closets, a luxurious primary bath with a soaking tub and huge shower area. The second floor also has 3 additional bedrooms, 1 with an en-suite bath and the other two with a Jack & Jill bath. The walk-out lower level will have approx 2200 Sq' of finished space. Minutes from town Center, Blue Ribbon award winning schools, parks, shopping, restaurants and approximately 1 hour commute to NYC.
Captivating 5 BR Tuscan-inspired home beautifully captures Mediterranean-style living, blending timeless elegance w/modern touches. Open floor plan features airy, sunlit rooms w/rich hardwood floors, latch-black wrought iron windows & French doors that invite natural light, ventilation & a connection w/nature. 3 FPLC add warmth & character. Main floor emphasizes Mediterranean design w/a seamless flow between indoor & outdoor spaces. LR & DR boast floor-to-ceiling windows & wood-burning FPLCs, creating an elegant yet inviting ambiance. Gourmet kitchen features custom Kraftmaid cabinetry, granite counters, wine fridge & high-end appliances. Family rm, framed by windows, opens thru double French doors to a redesigned patio, offering views of a lush lawn that flows into a scenic meadow, celebrating outdoor living. Luxe primary suite is a peaceful retreat w/a FPLC, full closets, & marble bath, complete w/ spa tub, shower & double vanities. Upstairs, 3 addl BRs (1 w/a walk-in closet, another w/a Murphy bed) share a sumptuous spa-like bath. Main floor 5th BR w/adjacent full bath showcasing flexibility for guests or home office. Additional spaces include: a bright finished 3rd flr & a 1,750 sq. ft. walk-out LL, w/a full bath, laundry room & French doors opening to a cobblestone patio, 2 car garage, mudroom, & a historic cottage w/renovation potential. Located in Lower Weston, close to Westport shopping, Aspetuck CC, & award-winning schools, this home is truly a special find.
Nestled in the heart of Weston, this timeless country estate is accessed via a private driveway and set on 6.77 secluded acres. Originally built in 1969 and beautifully refurbished in 2017, the stone and wood-shingled main house is a remarkable blend of historic charm and modern luxury. The thoughtful floor plan features a western-facing formal living room w/ fireplace, the perfect spot for enjoying stunning sunsets. Entertaining is a delight in the elegant dining room with its own fireplace, which flows seamlessly into the expansive kitchen which boasts a Calacatta Barerra marble coffee bar, a large center island, high-end stainless steel Bosch appliances, and bay window with a dining area that overlooks the professionally landscaped backyard and patio. Outdoor living is enhanced by a sparkling in-ground fiberglass pool, a cabana, a cozy pergola, and fire pit. The family room, complete with large stone fireplace and built-in bookshelves, provides a warm and welcoming space to unwind. Upstairs, the tranquil primary suite offers a fireplace, sitting area, luxurious five-fixture bath, and a private deck for ultimate relaxation. Two add'l ensuite BRs complete this level. The third floor includes two more BRs and full bath. The property also features an updated 5-stall horse barn with loft, a versatile space that has hosted memorable celebrations and offers endless possibilities. A true masterpiece, this home is a timeless treasure designed to be cherished for generations.
Discover your dream home in the picturesque town of Weston. This beautifully updated property boasts 2,431 square feet of thoughtfully designed living space, featuring 4 spacious bedrooms and 2 full baths. Step into the inviting living room, highlighted by soaring cathedral ceilings and a striking floor-to-ceiling fireplace that serves as a stunning focal point. The finished loft above offers additional versatile space, perfect for a home office or playroom. The master bedroom is a true retreat, complete with a cozy fireplace, a generous walk-in closet, and an en-suite full bathroom. Relax and unwind in this serene space, where comfort meets luxury. The remodeled kitchen is a chef's delight, featuring brand new cabinets, sleek quartz countertops, and stainless steel appliances. Whether you're entertaining guests or enjoying a quiet meal, this kitchen provides both functionality and style. This home is equipped with a new roof and HVAC system, ensuring comfort and efficiency year-round. Both bathrooms have been tastefully updated, blending modern finishes with classic charm. A spacious 3-car (2 attached and 1 detached) garage provides plenty of room for vehicles and storage.
Nestled in the verdant hills of Weston bordering Aspetuck Land Trust acreage, this 1940's charmer was reimagined by way of Provence, and the owners' extensive European travel. Oak hardwood flooring, romantic archways, vintage architectural details and custom French doors/windows transport you to the south of France. The home's highlight is a gorgeous country kitchen (Thermador, Bosch, SubZero, LG appliances) and a great room that boasts 9 ft ceilings, exposed beams and a Rumford fireplace. The elegant living room with built-in bookcases, original fireplace, and reading alcove leads to an outdoor pea gravel terrace beneath a leafy, grape arbor. An unexpected Yves Klein Blue dining room, and a wonderful library/office tempt guests to wait for the bar to run out! Spacious primary suite has a fireplace, sitting area and sweeping views of the property. Three additional bedrooms and two full bathrooms round out the second floor. Finished basement space with a full bath is above ground and currently being used for guests. And there is a wine cellar for those 58 degree needs! The privacy is captivating; a sun-drenched stone patio makes entertaining or peaceful reflection effortless. The fieldstone fireplace, outdoor kitchen with Viking gas grill, wood-fired pizza oven and refrigerator will encourage you to entertain friends and family. Boules you ask... the owners say Petanque, but the court is here along with a mature landscape, meandering stone walls and boxwood parterre gardens
This exquisite custom estate with pool site on 4.7+/- acres (poss./potential to divide) will take your breath away. Set atop one of the highest points in the area, this luxurious retreat blends modern luxury, convenience, privacy and treetop vistas into one irresistible package. Sited to capture the incomparable views, every room and multiple terraces have gorgeous panoramas, with a circulating waterfall to set the stage for the tranquility that awaits upon arrival. A seemingly endless list of amenities speak to a home that was constructed with no expense spared, everything from an elevator, natural gas utilities, 6 BRs with choice of main or upper level primary suites, incredible craftsmanship and highest-end materials. The stunning Great Room is at the heart of the home, with an impressive stone fpl, French doors to the terrace, adjacent wet bar/butler's pantry, incredible dining rm w/coffered ceil. The gourmet kitchen is a stunning showplace of sophisticated design and unparalleled quality w/ Sub Zero & wolf appls, marble counters, cathedral ceiling, skylights & three exposures capturing views. Two private offices for ultimate productivity. Each BR is accompanied by a luxe bath & fitted closets of outstanding quality. The finished, walk-out LL has an array of flex spaces and is an ideal future cabana for the pool site, or multi-generational suite w/full kitchen, fpl, BR, full bth, space for sauna & much more. 2 laundry rms, 3 car garage. Addl. space avail on 3rd flr.
Contemporary Colonial in a desirable neighborhood which has been completely updated with attention to detail throughout. Set on a private lot this home offers new vinyl siding, new roof, new windows and new driveway. The kitchen has been completely updated with beautiful tile flooring, white shaker cabinets, quartz counters and stainless appliances. Main level also has large living room with fireplace as well as family room with tons of natural light, a formal dining room as well as a den with sliders out to large flagstone patio. Upper level has 4 bedrooms including primary with new modern bathroom and walk-in closet. 3 other generously sized bedrooms as well as another modern bath. Large unfinished basement for possible expansion. House has a community well where several houses in the neighborhood share a well system. All major work completed/updated. Home is Move In ready. All that is needed is your personal touch. Easy to show, There are endless possibilities to make this property your own oasis. Don't miss out, See it today!
Nestled in the tranquil setting of lower Weston, this spacious 5-bedroom Colonial offers endless possibilities-whether you're looking to renovate or rebuild to create your dream home. The home will need some TLC to meet its full potential or the lot is perfect for new construction iThe flexible floor plan features a first-floor primary suite, a generously-sized kitchen, and multiple inviting living areas including a living room, dining room, and family room. An expansive bonus room with a closet and a private entrance sits above the garage, perfect for a home office, studio, or guest suite. The large, flat backyard is an entertainer's paradise, with ample space for gatherings, play, and outdoor activities. While the in-ground pool has not been opened in several years, the pool site holds potential for restoration. Original hardwood floors and a charming two-sided fireplace add character and warmth to the home, while new sliding doors open to a back deck, blending indoor and outdoor living seamlessly. Whether you're drawn to its existing charm or see the potential for a custom renovation, this property is a rare opportunity to create your own sanctuary in one of Weston's most peaceful locations. If you've been searching for the perfect fixer-upper, look no further-this is the one! House and pool sold as is.
Once in a while, a property emerges that transcends expectations - perfectly sited and timelessly designed. Welcome to 50 Kettle Creek Rd, a masterpiece of modern sophistication nestled on the toniest road in one of America's best towns. Ideally located close to town, schools, and the Merritt Parkway, this estate offers a rare combination of convenience and tranquility.This 6-bedroom home boasts a transitional style that seamlessly blends classic elements with contemporary design. Luxurious amenities abound, from the 3-car garage with 13' ceilings for car lifts to the custom kitchen equipped with top-of-the-line Thermador appliances and dual refrigerators. Gas fireplaces adorn both the family room and primary suite, creating warm and inviting spaces to gather and unwind. Step outside to discover an oasis of relaxation, featuring an inviting 18'x40' pool with a heater and auto cover, surrounded by lush landscaping and serene views of the sprawling 2.85-acre property. Once a cherished farmstead owned by a revered figure in town, 50 Kettle Creek pays homage to its heritage with an exterior reminiscent of the historic barn that once graced the land. With five of the six bedrooms situated on the second floor, including a flex-in-law suite and a secondary primary suite/guest room, this home offers ample space and flexibility for modern living. The finished basement provides an additional 2,200 square feet of living space, perfect for recreation or entertainment.
Adorable and well maintained home in the perfect location! Just minutes from the shops and restaurants of Georgetown is this wonderful 4BR Colonial/Cape with loads of charm and natural light. The main level includes a living room, dining room, newer kitchen and office/den as well as a half bath and the laundry room. The kitchen leads to a small enclosed porch that would make an ideal mudroom. Upstairs you will find three spacious bedrooms that share a full bath and the fourth bedroom on the third floor would make a fabulous playroom, additional office or home gym! All of this on a fabulous and level piece of property! Upgrades include hot water heater, electrical panel and newer roof. Amazing chance to get into the beautiful town of Weston that offers top ranked schools, a vibrant arts community and an abundance of natural open spaces! Hurry!
Contemporary style, on a cul de sac, 2 car garage, 4 bedrooms, 2 full bathrooms and 2 half bathrooms on a 1 Acre of land. Radiant heat, convenient location. Make an offer on this one today before it is gone.
RARE opportunity in lower Weston. The elegant design of this historic home is filled with timeless craftsmanship while uniquely updated for modern living. Recent extensive upgrades serve to honor but improve on the original classic design of this home. Among many attractive features is the four-car garage which could be a workshop, music or art studio. The two level in-law suite includes a living room, full kitchen, one and a half baths and bedroom and gives the new owners the option to to lease out the legal rental with estimated monthly income of ($2500-$3000). The main house has all new windows, wide plank floors, upgraded electrical, new hot water and well pump.Custom woodwork and built-ins have been completed by a master level craftsman.The unique layout includes two first floor bedrooms and full bath. The master is on the second level with a full bath and another bedroom with a walkout deck that could serve multiple uses. The fenced in back yard offers koi pond, blue stone patio, and mature plantings creating an ideal space for entertaining. If you are looking for the beauty of an antique home with thoughtful updates to suit a modern family, this home is a must see!
There are 21.2 acres of undeveloped property, in the heart of Lower Weston in Fairfield County, waiting for you and the home(s) of your dreams or keep it as is for 'the sporting life'. Country setting in lower Weston is only 1.4 miles to School Road and only 2.4 miles to town center. Potential 3 lot subdivision map located in suppliments. Seller had conditional approvals for 3 lots and 3 septic systems for three 5 bedroom single family home with lots and lots of spare acreage in 1999. The acreage includes paths, slopes and seasonal views in an area that attracts a variety of wildlife. Endless possibilities & only minutes to town and the most affordable natural multiple acreage property in Lower Fairfield County.
