Weston Real Estate

Welcome to Weston, Connecticut – a hidden gem nestled in the heart of Fairfield County. Known for its picturesque landscapes and tranquil ambiance, Weston is a charming town that beautifully balances rural serenity with modern conveniences. With its lush greenery, rolling hills, and scenic vistas, Weston offers a peaceful retreat just a short drive from the bustling energy of nearby cities.

Weston is renowned for its strong sense of community and commitment to preserving its natural beauty. The town boasts an array of outdoor recreational opportunities, from hiking and biking along the scenic trails of the Devil’s Den Preserve to enjoying a leisurely day at one of its many parks. Families will appreciate the highly-rated schools that prioritize academic excellence and foster a nurturing environment for students.

Culturally rich, Weston is home to a vibrant arts scene, with local galleries, theaters, and community events that celebrate creativity and foster connection among residents. The town also hosts various seasonal festivals and farmers’ markets, where you can savor fresh produce and artisanal goods while mingling with neighbors.

Conveniently located, Weston provides easy access to major highways and is just a stone's throw away from the coastal beauty of Long Island Sound. Whether you’re commuting to New York City or exploring the charming shops and eateries in nearby towns, Weston offers the perfect blend of suburban tranquility and urban accessibility.

Come discover why Weston is not just a place to live, but a place to thrive. Embrace the lifestyle you’ve always dreamed of in this idyllic Connecticut town!

Newest Listings in Weston

$3,200,000

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, this extraordinar

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

$2,449,000

5 Beds ⋅ 7 Baths ⋅ 24193559 MLS

SHOWINGS BEGIN ON WEDNESDAY, SEPTEMBER 16. Incredibly located on a gorgeous cul-de-sac of fine homes in a prime Lower Weston location, this luxurious Colonial is a showcase of style and comfort. Designed with tremendous attention to detail, the home's beauty begins with the landscaped setting and many outdoor amenities including a stunning pool and spa. The shingle exterior with stone accents greets your arrival into the soaring two-story entry with chic lighting, millwork and a custom staircase. The library with classic built-ins is an ideal home office. The living/music room with fireplace opens to the dining room, both with views of the private setting. The gourmet kitchen has a generous center island, custom cabinetry, Viking range, Sub Zero, pantry, open flow to the breakfast room with glass doors to the deck and into the exquisite family room with coffered ceiling & fireplace. Upstairs, the primary suite incl a sitting area, spacious marble bath and two excellent walk-in clsts. Each BR is large and all designer baths feature quality fittings. 3rd flr bonus rm has a half bath. The finished walk-out LL with full bath has three rooms, currently billiards rm, gym, and rec rm w/glass doors to the rear property. Lrg walk-in storage areas incl a finished clst. An exquisite oasis awaits at the resort-style pool w/ waterfall spa, firepit area, and vast entertaining areas, all surrounded by specimen plantings and emerald lawns. Storage shed. 3 car garage, mudroom, generator.

5 Aspetuck Gln, Weston

$679,900

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.

38 Ravenwood Dr, Weston

$2,189,000

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

$1,795,000

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

$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

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