Weston Real Estate

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

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 flood insurance was NOT required due to home's high elevation.

26 Pent Rd, 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

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

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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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