Homes for Sale near Weston High School

Set on 5+ private acres at the end of a coveted cul-de-sac, this distinctive family compound is minutes to town and top-rated schools. Classic New England architecture opens to a striking, loft-inspired interior defined by soaring three-story ceilings, hand-hewn antique beams from the late 1800s, wide-plank floors, and walls of glass that fill the home with natural light. Generous living spaces

Michelle Genovesi William Raveis Real Estate

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

Incredible rare reimagination and renovation opportunity in the heart of Weston in this spacious rustic 2728 sq ft rambling ranch with flexible layout and endless potential, nestled on 2 acres with mature gardens on a quiet cul de sac street among higher end homes can be your creative project! Invite the outdoors in through 8 skylights and easily step out into the extensive gardens through 8

Marilyn Sloper 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 distinctive Lower Weston retreat with incredible Post & Beam Barn is truly one to experience. Tucked away on more than 3.5 acres of wooded serenity, the home offers striking architectural details including soaring ceilings, pegged hardwood floors, exposed wood beams, and three stone / brick fireplaces. Multiple levels of living space create a dynamic & flexible floor plan. The chef's kitchen

Nannette Fatigate Berkshire Hathaway NE Prop.

A true family home incorporating 12 rooms 6 bedrooms 5 full baths, including a ground floor ensuite InLaw apartment,and 2 bedrooms The Premiere ensuite owners bedroom is on the second floor with a walk in shower and tub.Three other second floor bedrooms with two sitting areas with fire place , 2 bathrooms and an office leading to a second floor sun large family room next to the deck. A second W/D

Peter Sullivan Camelot Real Estate

Welcome to 11 Hunt Lane! This charming Colonial delivers lots of space and flexibility while situated at the end of a tranquil cul-de-sac in Lower Weston, near the Westport line. Perfect for entertaining, the sun-filled, spacious interior boasts excellent flow. Enter a charming two-story foyer flanked by a living room with fireplace and dining room with wet bar and sliders to a beautiful backyard

Denise Melendez Berkshire Hathaway NE Prop.

Perched atop a private, sun-drenched hill in the heart of Lower Weston, 123 Lyons Plain Road is a masterclass in charm and character. This home strikes the rare balance between secluded retreat and total convenience, located just minutes from the vibrant shopping and dining of Westport, local beaches, and easy commuting via the Merritt Parkway or Metro-North. Once inside the home, the

Karen Hagen Compass Connecticut, LLC

Surrounded by nature and complete privacy, this unique home offers a peaceful retreat with exceptional indoor-outdoor living. A large, welcoming entry foyer features tile flooring and a skylight that fills the space with abundant natural light. Hardwood floors and custom windows are found throughout the home.The main level showcases a spacious living room with a wood-burning fireplace and walls

Jenny Walsh Coldwell Banker Realty

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

2026 New Home Construction...Stunning transitional 5-bedroom estate blending classic curb appeal with a clean, modern interior - beautifully sited on 2.35 private acres. This immaculate five-bedroom home offers five ensuite bedrooms (including a luxurious primary suite), exceptional finishes and thoughtful details throughout:Thermador appliances, high-end fixtures, and gorgeous White Oak floors

Tom Kelley Coldwell Banker Realty

This sun-kissed contemporary captivates with private panoramic views overlooking the forever-green 14th and 15th fairways of Aspetuck Country Club. Designed to fully embrace its striking setting, this home offers a wide deck, large patio, five balconies, and grand windows framing views. Sited on two idyllic acres in bucolic Lower Weston, this premier property is minutes to the amenities and train

Lori Elkins William Raveis Real Estate

Set in a convenient Weston location, this adorable 2 bedroom ranch offers an inviting opportunity to enjoy one of Fairfield County's most desirable communities. Filled with character and easy living, this home offers a bright and comfortable layout featuring a modern kitchen, lovely living room, 2 bedroom, office nook and a full bath. A dry basement provides excellent storage. Highlights include

Jennifer Lockwood Coldwell Banker Realty

This architecturally distinctive mid-century modern Deck House offers a rare lifestyle retreat on two serene acres in Lower Weston. Designed to embrace its surroundings, the home features signature walls of glass, warm wood ceilings, and an open-flow layout that creates a seamless connection between the indoors and the natural beauty outside. The main residence makes an unforgettable impression

Karen Hagen Compass Connecticut, LLC

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

Opportunity in Weston! Set on a private 1-acre lot, this spacious ranch offers easy single-level living, generous room sizes, hardwood floors, an attached 2-car garage, and a desirable in-ground pool setting. The home features a large living area, eat-in kitchen, multiple bedrooms, two full baths, laundry room, and excellent indoor/outdoor potential with access to the rear deck and yard.

Gene Shklover AG Prime Realty

What if your primary residence and your vacation getaway were one and the same? Set on 2.56 private river-fed pond acres in coveted Lower Weston, 8 Wedges Field makes that question feel less like a fantasy and more like a Tuesday. Built by Michael Greenberg with the craft his homes are known for: antique wide plank chestnut floors, hand-hewn beams, custom millwork, soaring ceilings, and windows

Jesse Shafer Compass Connecticut, LLC

Set on three private acres of serene woodland along the banks of the Saugatuck River, this extraordinary Riverfront Retreat offers a rare opportunity to live immersed in nature in a modern masterpiece. Creating a seamless connection between the stunning interiors and the tranquil beauty of the surrounding landscape, experience breathtaking river views from the rooftop deck with succulent gardens,

Laurie Crouse Coldwell Banker Realty

Exceptional opportunity in a prime Lower Weston location directly bordering Westport - just minutes to both Weston and Westport town centers, award-winning schools, shopping, dining, trains and commuting routes. Privately set on a beautiful 2-acre lot on a quiet country lane, this property offers endless potential for buyers with vision. Whether you choose to renovate, customize, expand, or build

Christine Oleynick Keller Williams Realty

Welcome to 24 N Calvin Rd, an exceptional residence set in the prestigious enclave of Weston, where timeless elegance meets serene New England beauty. Perfectly positioned on a private, picturesque setting, this distinguished home offers a rare combination of sophistication, comfort, and refined living. Thoughtfully designed with attention to detail, the home features expansive, light-filled

Irsannia Gallardo eRealty Advisors, Inc.

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

Welcome to Hydrangea Hill - a beautifully maintained and refined center hall colonial set on 3 private acres in coveted lower Weston, offering the perfect balance of neighborhood warmth and serene retreat. The grand two-story foyer opens to a living room with marble gas fireplace, spacious formal dining room, and handsome private office. The heart of the home is a gourmet kitchen featuring a

Lori Di Bartholomeo William Raveis Real Estate

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

Completed in 2025, this extensively renovated and expanded residence lives like new construction, offering exceptional craftsmanship, luxury finishes, and a thoughtfully designed open floor plan. Featuring 5 bedrooms with potential for a 6th bedroom, 5 full baths, and 1 powder room, the home blends elegant design with comfortable everyday living. Rich hardwood floors flow throughout, complemented

Kasia Babinski William Raveis Real Estate

14 Saw Mill Road offers the convenience of suburban metropolitan New York living while maintaining a quaint, calm retreat by design. You are greeted by a historic draw bridge within the private drive that leads to the professionally landscaped and beautifully cared for lot. This home sits on about 2 acres, with privacy and room to live inside and out all year round. This oversized ranch offers a

Kelsey Emmons Coldwell Banker Realty

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

This exceptional 150-year-old antique estate in Lower Weston has been thoughtfully and stylishly reimagined, seamlessly blending timeless historic character with the luxurious amenities of contemporary living. The main residence strikes a perfect balance between grand, flowing entertaining spaces and cozy, intimate nooks tailored for remote work or quiet relaxation. At the heart of the home, an

Peter Depalo William Raveis Real Estate

Move-in ready and flooded with natural light, this exceptional European Craftsman home built in 2014 combines sophisticated architectural design and effortless modern living in highly desirable Lower Weston. Dramatic double-height ceiling anchors the open floor plan, creating an inviting atmosphere for everyday living and gracious entertaining. The chef's kitchen is well-appointed with stainless

Amanda Thornton Corcoran Centric Realty

Poised in the heart of Weston, the Kettle Creek Barn is a truly one-of-a-kind historic property blending timeless architecture with refined modern country living. Originally a 19th-century cedar board-and-batten barn converted into a residence in 1927, the home has been thoughtfully reimagined while preserving its extraordinary character and craftsmanship. The dramatic two-story great room

William J. Gill Compass Connecticut, LLC

Reminiscent of an European Estate this 4420 square-foot home features, four bedrooms, two full bathrooms and two half bathrooms on an open acre of land. It's extensive outdoor patio and entertainment areas wrap around the rear of the property, a cobblestone lined driveway, and specimen landscaping are all situated on a cul-de-sac in an easy to get to everything location. The gourmet kitchen

Peter Hastings Hastings Real Estate