Weston Homes with Colonial Style

Welcome to Weston, Connecticut – a picturesque town nestled in the heart of Fairfield County, where charm meets sophistication. With its serene landscapes, rolling hills, and lush greenery, Weston is an idyllic sanctuary for families and individuals seeking a tranquil lifestyle just a stone's throw from the vibrant city life of nearby Stamford and Norwalk.

Weston boasts a rich history and a strong sense of community, making it an ideal place to call home. The town is renowned for its top-rated schools, beautiful parks, and a plethora of recreational activities, ensuring that residents have access to both leisure and learning. Whether you enjoy hiking the trails at the scenic Weston Town Center or participating in community events, there’s something for everyone in this welcoming enclave.

One of the standout features of Weston is its stunning Colonial-style homes. These timeless residences exude elegance and grace, characterized by their symmetrical facades, gabled roofs, and classic detailing. With spacious interiors and beautifully landscaped yards, Colonial homes in Weston offer a perfect blend of traditional charm and modern amenities. Many of these homes are set on expansive lots, providing ample space for outdoor gatherings and family activities.

Living in Weston means embracing a lifestyle that values both community spirit and natural beauty. With its picturesque surroundings and exquisite Colonial homes, Weston is not just a place to live; it’s a place to thrive. Discover your dream home in this enchanting town and experience the perfect balance of tranquility and convenience. Your Weston adventure awaits!

Newest Weston Homes with Colonial Style

$2,449,000

5 Beds ⋅ 7 Baths ⋅ COMING SOON Status ⋅ 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

$2,189,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ COMING SOON Status ⋅ 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

$3,075,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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, Weston

$2,750,000

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24202390 MLS

Step inside this stunning Hampton-style estate where luxury meets pastoral tranquility. This 2001 HOBI award-winning home sits on two beautifully landscaped acres adjacent to the Aspetuck Land Trust with idyllic views. A scenic driveway lined with native plantings and paver stones leads to the gracious front porch and magnificent entryway. Inside, the formal living and dining rooms flow effortlessly, highlighted by a step-down great room with a striking fieldstone fireplace pellet stove. Freshly painted, the heart of the home is complete with updated Smart appliances, a center island, and a butler's pantry. Step outside to a backyard paradise featuring a large wooden deck, a terrace with an outdoor fireplace, a bluestone porch, and a peaceful koi pond with a stream. The main level is completed by a mudroom, half bath, and an oversized three-car garage with custom cabinetry. Upstairs, the primary suite serves as a private sanctuary with a decorative propane fireplace, built-ins, luxurious master bath, and dual walk-in closets. There are four additional upper level bedrooms, each featuring its own walk-in closet and en-suite bathroom. There is a spacious private office with custom built-in shelving and desk areas. The lower level features a versatile & large entertainment room; French doors open to a stone terrace, expansive garden, raised beds and beautiful flowers and herbs. Completing the backyard is a custom Glen Gate heated pool and attached hot tub with airblower jet.

27 Walnut Ln, Weston

$1,299,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24201546 MLS

Welcome to 181 Georgetown Road, a timeless Weston antique dating back to 1820 that beautifully blends historic character with modern comfort. Rich in period charm and thoughtfully updated for today's lifestyle, this inviting 4/5-bedroom, 3.5-bath residence offers nearly 3,000 square feet of living space set amidst picturesque grounds designed for year-round enjoyment. Inside, original architectural details and warm, welcoming spaces reflect the home's historic roots, while thoughtful updates provide modern convenience. Three renovated baths seamlessly combine classic style with contemporary finishes, while spacious living and entertaining areas offer flexibility for everyday living, gatherings with friends, and special occasions. Outdoor living is equally impressive. A spectacular solar-heated pool creates a private summer retreat, surrounded by mature landscaping and expansive grounds that enhance the property's peaceful setting. The barn is a standout feature, offering exceptional versatility with two-car garage parking, abundant storage, and exciting future potential for a finished second-floor loft, studio, office, gym, or guest space. Ideally located just minutes from the Cannondale train station for convenient access to New York City, as well as nearby shopping, dining, and local amenities, this special property offers the rare opportunity to enjoy the character and craftsmanship of a historic home while benefiting from updates that support modern living.

181 Georgetown Rd, Weston

$1,549,900

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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

$2,199,000

5 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 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

$949,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$1,000,000

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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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