Weston, CT Homes for Sale with Pool

Rock Ledge, a private estate in Weston, is set on nearly five acres surrounded by protected land at the end of a cherry-tree-lined private drive. A reimagined Tudor Revival that blends historic character with modern living. Originally built in 1918, the property was once the residence of Godspell author John-Michael Tebelak. It has evolved into a compound of a brick mansion, pool house with

John Schiaroli Coldwell Banker Realty

Bring your creativity and vision to make this distinctive home your own. Ideally situated in lower Weston, just 1 mile from the award-winning Weston schools and minutes, this contemporary style home is set on 2.23 private acres with a heated pool. The flexible, open floor plan features dramatic walls of glass that bring the outdoors in and showcase the beautiful surroundings year-round. The home

Georgia Wasserman Coldwell Banker Realty

Set privately in Weston, this extraordinary home is an early masterpiece by Michael Greenberg, featuring a meticulously relocated Vermont barn, rebuilt with exceptional care and craftsmanship. Rich in character, the residence blends rustic authenticity with refined, modern updates. The stunning great room is anchored by a dramatic three-story fieldstone fireplace, while the first-floor primary

Georgia Wasserman Coldwell Banker Realty

This rare private inholding offers a hilltop property defined by raw beauty and seclusion. The 1930s rustic hunting cabin sits on 1.6 wooded acres at the end of a private drive, surrounded by the 186-acre Brett Woods Conservation Area. The property provides a perfect balance of mature trees, rolling hills, and 18th-century stone walls-all located just eight minutes from Main Street Westport. With

Lisa Hartmann William Pitt Sotheby's Int'l

Tucked away on a coveted lower Weston cul-de-sac, this beautifully renovated colonial offers the rare combination of privacy, style, and resort-inspired living. Thoughtfully updated by the current owner, the home is truly turnkey and ready for its next chapter. Sun-filled interiors showcase sophisticated finishes and an effortless flow for both everyday living and entertaining. The renovated

Kim Harizman Compass Connecticut, LLC

**A Sun-Filled Weston Retreat with Exceptional Space, Style & Spectacular Grounds** Welcome to 81 Trails End Road, an impressive 12-room, 6-bedroom, 5-bath residence where exceptional natural light, beautifully designed living spaces and magnificent level grounds create a truly special place to come home. Oversized triple-pane Andersen windows capture sunlight throughout the day, filling

Michael Morris Vylla Home (CT) LLC

UNDER CONSTRUCTION - Photos are architectural renderings and are intended to illustrate the home's anticipated finished appearance. Actual finishes, materials, features, and landscaping may vary. Be the first to own this exceptional new luxury home in one of Weston's most desirable locations. Situated on approximately 2 private acres, this custom-designed 5,600 SF residence offers 4 bedrooms, 4

Pilar Rios US Asset Realty

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer.

Barbara Bross Coldwell Banker Realty

Welcome to 10 Dragonwood Lane - The Iconic Origami House Set on an extraordinary 15.57-acre estate spanning four separately deeded parcels, 10 Dragonwood Lane is a one-of-a-kind architectural masterpiece that seamlessly blends modern design, luxury, and nature. Known as the Origami House, this remarkable residence offers unparalleled privacy, tranquility, and future development potential while

William Martin Douglas Elliman of Connecticut

Grand and gracious, this impressive custom Colonial on estate property with a gorgeous gunite pool is ideally set in convenient Lower Weston. Just 2.3 +/- miles to the Merritt Parkway & 1.6 +/- mi to the convenient school campus & town Center, this home blends the appeal of a tranquil setting with immediate access to all amenities. Introduced from a paved circular drive, this architecturally

Alex Chingas Coldwell Banker Realty

In the heart of a neighborhood known for fine estates and just moments from the campus of award-winning schools, this distinguished 2.5 +/- acre property elevates your lifestyle with refined craftsmanship and effortless luxury. A grand foyer with a graceful floating staircase introduces interiors defined by exquisite walnut floors, incredible millwork, and architectural moments to savor at every

Alex Chingas Coldwell Banker Realty

Discover a truly special country retreat where warmth, character & timeless New England charm come together. Tucked away at the end of a long private drive, this inviting home offers a refreshing departure from the ordinary, with a thoughtfully designed floor plan that creates comfortable, flexible spaces for today's lifestyle. Sunlight streams in, enhancing the home's welcoming atmosphere &

David Weber Compass Connecticut, LLC

Extraordinary riverfront modern retreat set against a breathtaking backdrop of waterfall, woodland, and sweeping water views in one of Weston's most remarkable settings. Surrounded by preserved land and trails of Devil's Den Preserve, this extensively renovated residence offers a rare connection to nature paired with sophisticated design and luxury amenities. Walls of glass, soaring ceilings, and

Jennifer Twombly Compass Connecticut, LLC

Embrace the ultimate country club lifestyle at this stunning two-acre estate, where privacy and recreation meet in perfect harmony. The grounds are rich with amenities, including a sparkling Gunite pool and spa, a private tennis court, and a separate sport court. The thoughtfully designed pool house elevates every gathering with its summer kitchen, changing room, half bath, and refreshing outdoor

Randy Musiker Compass Connecticut, LLC

Luxury new construction opportunity in Lower Weston! Currently slated for completion in less than a year, this meticulously crafted estate offers a rare opportunity to secure your forever home on a private Lower Weston cul-de-sac. Take advantage of your opportunity to live in the most convenient Weston location within minutes of their top rated schools and town center. Plus enjoy the convenience

Lauren Turner Corcoran Centric Realty

Thoughtfully sited high above Aspetuck Country Club's picturesque 16th fairway, this 5-bedroom, 4-bath residence offering over 5,300+ square feet was curated from the ground up to celebrate its extraordinary setting. Walls of glass, soaring vaulted ceilings, skylights, and multiple decks were thoughtfully designed to capture the ever-changing play of natural light-from the first rays of sunrise

Vickie Kelley Camelot Real Estate

Rare Opportunity to own two private acres on the Aspetuck River in Westport. Tucked away at the end of a quiet cul-de-sac, this gracious Colonial offers an extraordinary blend of privacy, natural beauty and relaxed country living. Set on two spectacular acres, the property extends to and beyond the banks of the river, creating a truly unique waterfront retreat. A natural riverside setting invites

Beverly Walsh William Raveis Real Estate

Set behind private gates in Westport's prestigious Red Coat estate area, this extraordinary luxury residence offers the utmost in privacy and sophisticated design. Thoughtfully conceived with elegant architecture, exceptional proportions, soaring 10-foot ceilings on the main level, 9-foot ceilings on the second floor and finished lower level, and light-filled interiors, the home blends

Cyd Hamer William Pitt Sotheby's Int'l