Weston Real Estate

Welcome to Weston, Connecticut – a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes and serene residential neighborhoods, Weston offers a perfect blend of suburban tranquility and vibrant community life. With a population of just over 10,000, this charming town is characterized by its lush greenery, expansive parks, and a strong commitment to preserving its natural beauty.

Weston is renowned for its excellent school system, making it a sought-after location for families. The schools here consistently rank among the top in the state, providing children with a quality education and a supportive environment. The town’s commitment to education is reflected in its community spirit, where residents actively participate in various local events and initiatives.

Outdoor enthusiasts will find plenty to love in Weston. The town boasts numerous trails and parks, including the stunning Weston Town Center and the scenic Bisceglie-Scribner Park, perfect for hiking, biking, and enjoying nature. With its rich history and charming architecture, Weston also offers a delightful mix of quaint shops, local eateries, and cultural experiences.

Conveniently located just a short drive from major metropolitan areas, Weston provides easy access to urban amenities while maintaining a peaceful, rural atmosphere. Whether you’re looking for a family-friendly community, a place to retire, or a vibrant environment to grow, Weston, CT is an ideal choice. Discover the charm of Weston and make it your new home today!

Newest Listings in Weston

$1,795,000

6 Beds ⋅ 4 Baths ⋅ 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 envision your dream backyard with the property's POOL PERMIT offering endless possibilities. 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

$1,595,000

4 Beds ⋅ 4 Baths ⋅ 24205730 MLS

Quintessential New England Colonial meets updated living at this gracious home. Set amid mature trees, stone walls and beautifully established gardens, this 4-bedroom, 3.5-bath home offers wonderfully proportioned rooms in a private, park-like setting - yet remains a commuter's dream. Inside, freshly painted rooms, refinished hardwood floors, and abundant natural light create a warm and inviting backdrop. The elevated open kitchen has new appliances: Wolf gas range, Sub-Zero refrigerator, double wall ovens, Bosch dishwasher, Zephyr hood. A fully renovated mudroom adds everyday functionality. The lower level has a playroom featuring 2 walls of windows, a renovated bathroom, study/gym room and access to the outside with in-law or au pair possibilities. For the car enthusiast, hobbyist or collector, the completely renovated garage is exceptional-finished with epoxy floors, insulated garage doors with Wi-Fi openers, heating & cooling via mini-splits on both levels, and three 50-amp EV chargers. Significant improvements continue throughout, including new central air components, an oversized septic field, generator connection, new 30-year asphalt and EPDM roofs, gutters w/ leaf guards, new chimney cap. Outdoors, extensive gardens, stone walls, bluestone patio and new garden shed complement the expansive lawn and surrounding woodland. A peaceful retreat that feels worlds away, with exceptional commuting convenience and all that Weston and Fairfield County have to offer.

227 Newtown Tpke, Weston

$599,900

3 Beds ⋅ 2 Baths ⋅ 24205265 MLS

Welcome to an incredible opportunity in the highly desirable town of Weston! Set back from Newtown Turnpike on a secluded, level 1.33 acre lot, this exceptionally well maintained 3 bedroom, 2 full bath ranch offers 1,332 square feet of comfortable single level living with hardwood floors throughout and a detached two car garage. Ideally located near the Saugatuck Reservoir, Merritt Parkway, and Devil's Den Nature Preserve, the property is ready for its next owner's vision. Thoughtful updates could transform the existing home into a beautiful retreat, while the generous lot may offer exciting possibilities for expansion, including a potential second story addition or new construction, subject to town approvals. Surrounded by impressive neighboring homes, the possibilities here are substantial. Whether you're looking to renovate, expand, build new, or simply create your dream home while enjoying convenient single level living, this Weston property offers a rare combination of location, privacy, land, and potential.

261 Newtown Tpke, Weston

$3,075,000

5 Beds ⋅ 6 Baths ⋅ 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

$2,000,000

5 Beds ⋅ 7 Baths ⋅ 24204750 MLS

Refreshed and gorgeous, 30 Soundview Farm Road is a timeless Nantucket-style colonial in one of Weston's most desirable locations. Designed by renowned Fairfield County architect Michael Greenberg, this home blends classic elegance with a layout made for today's lifestyle. Flooded with natural light, brand-new light hardwood floors lend an air of coastal Connecticut, all tucked away on a private cul-de-sac. The grand entry is flanked by a formal dining room and living room, both perfect for holiday entertaining. The bright, airy kitchen features a breakfast bar, large dining area, and abundant counter space and storage. It opens to a family room anchored by a wood-burning fireplace encased in natural stone, plus a stylish wet bar with brand-new appliances. A cozy den or guest room with a private bath completes the first floor. Upstairs, the primary suite is a true retreat with high ceilings, two walk-in closets, a luxurious en-suite bath, and a balcony overlooking the grounds, plus an adjoining room perfect for a home office or sitting area. Three additional en-suite bedrooms offer comfort and privacy for the whole family. The partially finished lower level adds versatility as a gym and recreation space. Set on beautifully landscaped grounds bordering Aspetuck Country Club, 30 Soundview Farm Road offers privacy, timeless design, and unmatched lifestyle in one of Weston's most sought-after neighborhoods.

30 Soundview Farm Rd, Weston

$199,999

24204000 MLS

Tucked at the end of a peaceful cul-de-sac in Weston, this private 2-acre lot is a builder's blank canvas in one of Fairfield County's most coveted communities. The property offers a blank slate for builders and buyers ready to bring their own plans to life, free from the constraints of an existing design. Just minutes from schools, shopping, dining, and major commuting routes, this is a rare chance to create something truly your own in one of the area's most sought-after in-town locations.

354 Good Hill Rd, Weston

$1,100,000

3 Beds ⋅ 2 Baths ⋅ 24198647 MLS

Imagine a storybook Cape along a babbling brook, surrounded by overflowing hydrangeas and mature plantings... this inviting lower Weston home feels like a private English country refuge. Pass through the white driveway gates, and you'll admire the classic cottage charm complete with new cedar roof. Inside, abundant natural light streams through multiple skylights, oversized windows, and French doors. The open living room with gas fireplace, dining room and refreshed kitchen flow easily for everyday living and entertaining. A first-floor primary bedroom offers convenient one-level living, with two additional bedrooms and a full bath upstairs. A cozy den offers space to relax, while a bonus room is flexible as a home office or mudroom. Multiple closets and a walk-up attic over the garage provide excellent storage. Outside, a screened porch and secluded, fenced patio framed by mature perennials invite you to relax, dine, and enjoy balmy summer evenings, while the brook adds to the bucolic setting. Set on just under an acre, the home offers a wonderful sense of peace and privacy. Recent updates include a refreshed kitchen and bathrooms, plus exterior paint. Weston offers excellent schools and a location just minutes from Westport's shopping, restaurants and beaches, with the train station to NYC is approximately 15 minutes' drive. Move-in ready with a quick closing available... book your showing and prepare to be charmed!

24 Good Hill Rd, Weston

$739,000

4 Beds ⋅ 4 Baths ⋅ 24203031 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

$1,249,000

5 Beds ⋅ 3 Baths ⋅ 24202535 MLS

Nestled at the end of a quiet cul-de-sac on two picturesque acres, this extraordinary five-bedroom, three full bath residence offers a rare combination of timeless elegance and peaceful seclusion. Overlooking a gently flowing brook, the property is surrounded by natural beauty, creating a private retreat just minutes from the vibrant shops, acclaimed restaurants, beaches, and Metro-North train station in neighboring Westport. Designed for both everyday living and effortless entertaining, the home features two luxurious primary suites, including one on the main level and a second upstairs with its own private balcony overlooking the tranquil landscape. The sleek kitchen is beautifully appointed with new countertops, while the bathrooms offer sophisticated, contemporary finishes. Brand-new Andersen windows throughout bathe the home in natural light while enhancing comfort and efficiency. Offering an exceptional balance of privacy, convenience, and refined living, this is a rare opportunity to own a truly special home in sought-after Weston.

21 Deepwood Rd, Weston

$2,750,000

5 Beds ⋅ 7 Baths ⋅ 24202390 MLS

Step inside this stunning Hampton-style estate where luxury meets pastoral tranquility. This 2001 HOBI award-winning home sits on two beautifully landscaped acres adjacent to the Aspetuck Land Trust with idyllic views. A scenic driveway lined with native plantings and paver stones leads to the gracious front porch and magnificent entryway. Inside, the formal living and dining rooms flow effortlessly, highlighted by a step-down great room with a striking fieldstone fireplace pellet stove. Freshly painted, the heart of the home is complete with updated Smart appliances, a center island, and a butler's pantry. Step outside to a backyard paradise featuring a large wooden deck, a terrace with an outdoor fireplace, a bluestone porch, and a peaceful koi pond with a stream. The main level is completed by a mudroom, half bath, and an oversized three-car garage with custom cabinetry. Upstairs, the primary suite serves as a private sanctuary with a decorative propane fireplace, built-ins, luxurious master bath, and dual walk-in closets. There are four additional upper level bedrooms, each featuring its own walk-in closet and en-suite bathroom. There is a spacious private office with custom built-in shelving and desk areas. The lower level features a versatile & large entertainment room; French doors open to a stone terrace, expansive garden, raised beds and beautiful flowers and herbs. Completing the backyard is a custom Glen Gate heated pool and attached hot tub with airblower jet.

27 Walnut Ln, Weston

$1,299,000

4 Beds ⋅ 4 Baths ⋅ 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

$2,250,000

4 Beds ⋅ 6 Baths ⋅ 24201533 MLS

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen--all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private oasis awaits--an expansive deck overlooking the river, scenic landscaping, and a stone patio with gunite pool--perfect for summer relaxation or entertaining under the stars. In addition to the numerous recent improvements to the key systems of the home, the driveway has been redone and the house has been painted on the interior and exterior. Whether you're looking for a peaceful retreat or a forever home, this extraordinary property offers an unparalleled lifestyle in an idyllic setting.

6 Old Orchard Dr, Weston

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