Weston Real Estate

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Newest Listings in Weston

$1,299,000

4 Beds ⋅ 3 Baths ⋅ 24200819 MLS

Just 1/2 mile from the Westport border on a prestigious Weston cul de sac sits this beautiful, spacious 4 bedroom family colonial. Expansive kitchen gleams with stainless steel appliances and opens to family room with fireplace. Rounding out the ample first floor is a large living room with a second fireplace, cozy dining room, and spacious sun room that opens to the large deck and lovely backyard. Specimen trees and professional landscaping with sprinkler system surround the house and welcome you in all seasons. Inside, 4 bedrooms all on the second floor, including large master suite with oversized walk-in closet connecting to attic storage. Walk-out finished lower level features finished playroom and even more storage. Currently carpeted but hardwood floors throughout. Rare in Weston -- home is on natural gas and very effective, Quiet and very peaceful setting. Enjoy your morning coffee on the cedar deck with the birds.

4 Pilgrim Ln, Weston

$1,549,900

6 Beds ⋅ 6 Baths ⋅ 24199857 MLS

**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 virtually every room with wonderful warmth and brightness while framing peaceful views of the surrounding property. The heart of the home is the **newly renovated chef's kitchen**, thoughtfully designed with a substantial center island, abundant cabinetry, fireplace and inviting breakfast area. Spacious, bright and beautifully appointed, it provides an ideal gathering place for everyday living as well as effortless entertaining. The kitchen flows naturally to the sun-filled living spaces, including a south-facing sunroom overlooking the pond and pool, expansive family room, generous dining room and cozy reading room with fireplace. The main level also offers a private en-suite in-law arrangement, providing wonderful flexibility for extended family, guests or first-floor living. Upstairs, the impressive primary suite is a peaceful retreat with a beautifully appointed bath featuring a walk-in shower and soaking tub. Three additional bedrooms, two full baths, two sitting areas with a fireplace, an office and convenient second laundry area provide exceptional space and versatility.

81 Trails End Rd, Weston

$1,795,000

5 Beds ⋅ 5 Baths ⋅ 24197636 MLS

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 & unique architectural character. Rich in authentic details-including reclaimed hand-hewn beams, 2 fireplaces, brick and hardwood floors, a country kitchen & a screened porch-the home offers five bedrooms & five full baths. The dramatic great room is the heart of the home-a relaxed, barn-inspired space with soaring cathedral ceilings and painted floors, made for gathering. Flowing easily to the kitchen, screened porch and pool, it's where entertaining feels effortless and traditions are made. The expansive rec room, with soaring vaulted ceilings, is ideal for a home gym, golf simulator, office, studio, or recreation room, while an additional loft provides extra space for work or relaxation. Outside, beautifully landscaped grounds create a private sanctuary. Colorful gardens frame every view, while the screened porch, patio & in-ground pool invite effortless indoor-outdoor living-from peaceful morning coffee to memorable summer gatherings. Walk or ride bikes to the Weston School Campus. This is a home for buyers seeking character, versatility & a lifestyle that is anything but cookie cutter

15 Birch Hill Rd, Weston

$2,199,000

5 Beds ⋅ 8 Baths ⋅ 24191028 MLS

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 striking residence makes a memorable impression. The foyer welcomes you to the airy, grand-scale interior which is filled w/sunlight. Upon entering, you will be drawn to the spectacular Great Room w/a 2+ story ceiling & incredible windows that span the full height, bringing exquisite vistas into the home and creating an exceptional backdrop for memorable moments. The octagonal DR is lined w/windows and built-ins. The custom kitchen was recently remodeled w/excellent taste & quality, incl double islands, dual ovens, warming drawer & a lrg breakfast rm w/bar, all opening to the fam rm w/1 of 5 fpls. Incredible office/library w/ herringbone wood floor & fpl. Nearly all main level rooms have French doors to the deck & patio. The flexible layout incl an attached pool house/extra BR w/full bth on the main floor. Upstairs, find 5 exceptional BR suites, beginning with the vast primary that incl an ofc/sitting rm w/fpl, vltd ceil BR w/3 walk-in clsts & lrg marble bth. Finished walk-out LL w/ rec/play rm, full bth & storage. Stunning pool & waterfall spa, level lawns, gardens. 3 car garage.

79 Cavalry Rd, Weston

$1,000,000

3 Beds ⋅ 4 Baths ⋅ 24197884 MLS

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 offers 4 bedrooms. a private office, and a finished walkout lower level with direct access to the pool-perfect for entertaining, recreation, or extended living.

33 Birch Hill Rd, Weston

$900,000

24197446 MLS

Rare opportunity to build your dream home in one of Weston's most desirable locations. Situated on a private 2-acre lot at the end of a quiet cul-de-sac, 338 Good Hill Road is being offered with full town approvals and complete engineering plans already in place, allowing you to begin construction without the lengthy approval process. The approved plans feature a stunning 5-bedroom, 6-bathroom custom home with just over 6,000 square feet of finished living space, thoughtfully designed for today's luxury lifestyle. Enjoy the perfect combination of privacy, convenience, and an exceptional in-town location just minutes from award-winning schools, shopping, dining, and commuting routes. Whether you choose to build the approved design or customize it further, this is a turnkey opportunity to create an exceptional new construction home in one of Fairfield County's most sought-after communities.

338 Good Hill Rd, Weston

$6,500,000

4 Beds ⋅ 5 Baths ⋅ 24196609 MLS

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 bordering a serene nature preserve. A winding, tree-lined driveway leads past flowering cherry trees, a private electronic gate, and a lighted tennis court before unveiling the home's breathtaking contemporary design. Conceived by the renowned Leroy Street Studio of Manhattan, the approximately 8,500-square-foot residence draws inspiration from the art of folded geometry. Sculptural cube-like forms create dramatic ceiling heights, expansive walls of glass, and light-filled interiors that effortlessly blur the distinction between indoor and outdoor living. At the heart of the home is the spectacular Glass Great Room, inspired by I.M. Pei's iconic Louvre Pyramid. Enclosed by glass on three sides, this extraordinary space opens onto an expansive terrace overlooking one of two cascading waterfalls within the estate's nationally recognized koi sanctuary. Designed for both sophisticated everyday living and grand-scale entertaining, the residence offers:

10 Dragonwood Ln, Weston

$949,000

3 Beds ⋅ 3 Baths ⋅ 24194502 MLS

**NEWLY PRICED** Tucked behind classic wood rail fencing and stone walls, this charming, beautifully updated Colonial offers turn-key living with a right-sized footprint in a private Weston setting. Thoughtful improvements include renovated baths, new windows, a new roof, new kitchen appliances and numerous additional updates-allowing the next owner to simply move in and enjoy. The welcoming floor plan makes smart use of every space, with formal living and dining rooms and French doors opening to an expansive wraparound deck for easy indoor-outdoor living. A sun-filled family room with vaulted ceilings adds an airy gathering space, while the well-appointed kitchen and powder room complete the main level. Upstairs, the primary suite features a custom walk-in closet and en suite bath, with two additional bedrooms and a full hall bath. The finished walk-out lower level, with its own entrance, adds valuable flexibility for a home office, playroom, fitness space or guests. Set on .83 private acres, the property strikes an ideal balance of privacy, outdoor space and lower-maintenance living, with a generous front yard, expansive back deck and peaceful babbling brook. Less than one mile from Weston's award-winning schools and convenient to major highways and NYC. Newly priced and truly move-in ready, this is a compelling opportunity to enjoy the privacy and lifestyle of Weston without the projects.

267 Newtown Tpke, Weston

$2,299,000

4 Beds ⋅ 6 Baths ⋅ 24187328 MLS

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 full bathrooms, 1 half bath, and a 3-car garage. Designed with luxury and comfort in mind, the home features soaring cathedral ceilings, an open-concept floor plan, a fireplace, a gourmet kitchen with premium appliances, a finished lower level, heat pump with central air, private well and septic, and a spectacular in-ground pool for exceptional indoor-outdoor living. There may be an opportunity to add select personal touches depending on the stage of construction. Don't miss this rare opportunity to own a brand-new luxury home in Weston. Specifications, dimensions, features, finishes, pricing, and completion timeline are subject to change without notice.

15 Cannondale Rd, Weston

$1,050,000

5 Beds ⋅ 5 Baths ⋅ 24194291 MLS

Are you a visionary? An Investor? Or an End user looking to put your personal stamp on a home built with quality construction & golf course views? If so, then this is the home for you! A perfect blend of contemporary design paired w/elements of charm define the spaces of this home w/ beams, barrel ceiling & an Arts and Crafts vibe. Enter through the large foyer with curved ceiling and tree trunk flooring. Step down into the Living room which shares a large 2 sided fieldstone fireplace with the Dining Room overlooking the golf course. These rooms share an open concept living arrangement including a family room with sliders leading to large two-tiered deck. The eat-in kitchen has a wet bar & side entrance to the house through a mudroom & half bath. Off the kitchen is a bright sunroom also w/ sliders to the deck. The main level also includes an office w/ builtins, 3 large bedrooms plus a primary with builtins, ensuite bath & huge walk-in closet. The walkout lower level has a big rec/play/family room w/ fireplace, a full kitchen & a bedroom with bath. Great set up for in-law, au pair or a dreamy suite. Outside is beautiful professionally landscaped property with specimen plantings & mature trees & a tennis court to boot! While this home is in need of cosmetic updates, the structure & mechanics have been well maintained by the original owners. This is an estate and is being sold "As Is". Bring your vision to create a beautiful and peaceful sanctuary!

22 Codfish Ln, Weston

$1,799,000

4 Beds ⋅ 4 Baths ⋅ 24183665 MLS

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 shower. Perched above the detached garage, you'll find a quiet retreat with a half bath - the perfect set up for a professional home office, a dedicated creative studio, or a home gym. The main residence is a sun-drenched contemporary, offering three finished levels of effortless living. Soaring ceilings and well-placed skylights create an airy atmosphere, while hardwood floors anchor the intuitive floor plan. All four bedrooms are tucked away on the upper level. The walkout lower level adds even more versatility, ready to serve as a media room, play room and/or a fitness hub to suit your needs. All this just minutes from Weston's top-rated schools, the town center, the Merritt Parkway, and neighboring Westport. Whether you're lounging poolside, perfecting your serve, or simply savoring the serenity of this incredible property, every day here feels like a getaway.

7 White Oak Ln, Weston

$1,000,000

4 Beds ⋅ 3 Baths ⋅ 24188955 MLS

Welcome to this spacious 4-bedroom, 3-bath Colonial offering 2,700+ square feet of versatile living space in Lower Weston. Set on 2.3 private wooded acres, the home features a flexible floor plan with generous living areas, a finished lower level, and a bright four-season room that provides additional year-round living space. The main level has the convenience of first-floor laundry along with an additional room and full bath, creating an ideal setup for guests, or a home office, while the finished lower level adds even more flexibility for a den or entertaining. Enjoy the best of Weston living with award-winning schools, and convenient access to major commuting routes. Here's your opportunity to create your dream home in one of Fairfield County's most desirable communities.

103 Steep Hill Rd, Weston

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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.