Weston CT Homes for Sale and Town Profile

Explore and download Weston demographics and school report cards, discover local neighborhoods and condo/townhouse communities, and learn about commuting routes and popular landmarks.

Snapshot

Where: Southwest Fairfield County, Western CT
Population: ~10,400 residents
Size: ~20.7 sq mi
ZIP / Area code: 06883 / 203

Where It Is

By car: Located about 45 miles from New York City, accessible via Route 57 and the Merritt Parkway. Approximately 60 minutes to NYC in moderate traffic. By rail: Weston is notably the closest Connecticut town to NYC without a train station — a quirk of history that has preserved its rural character. Residents typically drive to nearby Westport or Wilton stations on the Metro-North New Haven and Danbury lines. Nearby: Borders Westport, Wilton, Redding, Easton, and Fairfield.

Overview

Weston is one of Connecticut's most private and prestigious communities — a town where nature genuinely reigns supreme. With just over 10,000 residents spread across 20.7 square miles, Weston enforces two-acre minimum zoning and has dedicated nearly a quarter of its land to permanently protected open space. The result is a community of extraordinary privacy, wooded landscapes, and quiet country roads that feels worlds away from the city — while remaining well within reach of it.

Community & Lifestyle

Weston's social life revolves around its strong community connections rather than a commercial downtown. The town center offers basics — a market, post office, gas station — and that intentional restraint is part of the appeal. Residents enjoy the Weston Field Club (tennis, outdoor pool, lake), Aspetuck Country Club (golf, luxury amenities), and a rich calendar of community events including the Memorial Day Fair, Fourth of July celebration at the middle school, Halloween ragamuffin parade, and a beloved farmers' market.

A bonus for outdoor-minded residents: Weston homeowners enjoy discounted seasonal passes to Westport beaches — a perk typically reserved for Westport residents, making Weston a compelling value for those who want access to the shore without the shore price tag.

Education

Weston's public school district is consistently ranked among the very best in Connecticut and the nation. All four schools — Hurlbutt Elementary, Weston Intermediate School, Weston Middle School (with its Olympic-sized pool), and Weston High School — are located on a single central campus. Weston High School has been ranked as high as #1 in Connecticut and #47 nationally, with a 100% graduation rate, 97%+ college enrollment, and strong AP and IB participation. The Connecticut State Department of Education places Weston in District Reference Group A — the nine most academically high-performing districts in the state.

Parks & Recreation

Devil's Den Preserve — the largest nature preserve in Connecticut at nearly 1,800 acres — lies largely within Weston, offering over 20 miles of well-maintained trails, diverse wildlife habitats, and remarkable natural beauty. Bisceglie Park features a man-made swimming pond, baseball fields, and fitness trails. Lachat Town Farm is a community farm with gardens, animals, and seasonal events, including a popular farmers' market. Additional trails are maintained by the Aspetuck Trail Association.

Real Estate & Housing

Weston's housing market is defined by privacy, space, and natural beauty. Two-acre zoning means properties are substantial — ranging from lovingly maintained antique farmhouses and modest homes to dramatic luxury estates and sprawling contemporary residences. There are no condos or apartments; this is exclusively a single-family home community. Home values are consistently among the highest in Connecticut and the nation, reflecting the town's extraordinary schools, open space, and exclusivity.

Government

Weston is governed by a Board of Selectmen, with strong citizen engagement through town committees, a volunteer fire department, and active civic organizations including the Kiwanis Club, League of Women Voters, and Weston Garden Club.

Notable Facts

Beach Access: Weston residents enjoy discounted access to Westport beaches — a rare and valuable perk.
No Railroad: Weston is the closest CT town to NYC without a train station — a historical quirk that preserved its rural character.
Top Schools: Weston High School has been ranked among the top 50 high schools in the United States.
Open Space: Nearly 25% of Weston's land is permanently protected open space.

Vibe

Deeply private, naturally beautiful, and quietly sophisticated. There's no downtown, no traffic lights, and no hustle — just wooded roads, exceptional schools, and a community of highly educated, accomplished residents who value their privacy and their neighbors in equal measure. This is a town for people who know exactly what they want.

Who It's For

Great fit for: Buyers seeking maximum privacy and green space without sacrificing school quality; those for whom education is the top priority; buyers who want a genuine countryside lifestyle within commuting distance of NYC. Consider elsewhere if you need walkable shopping, a train station, or lower price points.

Thinking About Weston?

Weston's inventory is limited and moves quietly. I'd love to help you navigate this market — reach out to get ahead of new listings before they hit the public.

Newest Listings in Weston CT

$959,000

ACTIVE Status ⋅ 24205345 MLS

Welcome to Hills End Lane, an exclusive enclave of distinguished estates just minutes from Weston's charming town center. This exceptional 2.53-acre property presents a rare opportunity to create a custom residence in one of Weston's most desirable settings. The level, lightly wooded site offers privacy and natural beauty, with 50 feet of road frontage and approximately 0.9 acres of protected wetlands and watercourses. The property is septic-approved, meets town setback requirements, and has received Inland Wetlands Commission approval. A proposed pool site further enhances the property's design possibilities. Underground gas, electric, and cable are available at the street. Renowned for its exceptional schools, scenic trails, and convenient access to Westport and the Merritt Parkway, Hills End Lane offers an extraordinary setting to bring a distinctive vision to life. Agent is Owner.

10 Hills End Ln, Weston

$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

$679,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205703 MLS

Welcome to 38 Ravenwood Drive, a classic Cape Cod-style home set on a private 2-acre parcel in desirable Weston. Offering approximately 1,515 square feet of living space, this 3-bedroom, 2-full-bath residence features a comfortable layout with two fireplaces, central air. A standout feature is the expansive wrap-around deck, offering a wonderful outdoor setting for entertaining, relaxing, and enjoying the surrounding natural landscape. Mature trees and the generous 2-acre lot provide a sense of privacy and tranquility while maintaining convenient access to area schools, shopping, dining, parks, and commuter routes. A great opportunity to bring your vision to this well-located Weston property and create a home tailored to your lifestyle.

38 Ravenwood Dr, 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

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24205738 MLS

Light-filled, beautifully renovated and wonderfully versatile, this striking Weston 5/6 bedroom contemporary OFFERS OVER 5,000 square feet of living space in a private yet convenient setting. From the moment you enter, the home impresses with a dramatic great room featuring soaring cathedral ceilings, skylights and walls of windows that bring the outdoors in. Designed for everyday living and entertaining, the open, airy floor plan features two fireplaces and multiple decks for relaxing and enjoying the surrounding landscape. The renovated kitchen offers brand-new appliances, generous workspace and an easy connection to the living and dining areas. The main-level primary suite provides the ease of one-floor living, while additional bedrooms offer plenty of room for family and guests. A private space above the garage is ideal as an au pair suite, guest quarters or home office. The finished lower level adds even more flexibility with space for a possible 6th BR, recreation/media room, fitness area and kitchenette. Numerous decks overlook the beautiful private yard. Just minutes from charming Weston Center and Weston's top-rated schools, residents also enjoy beach rights at Westport's Compo Beach. A rare combination of space, style, privacy and convenience. Enjoy the best of Weston living-peaceful surroundings, award-winning schools (bus stop at end of driveway!), a welcoming town center and easy access to Westport's shopping, dining, train and beaches.

158 Steep Hill Rd, 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

$599,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24205265 MLS

Welcome to an incredible opportunity in the highly desirable town of Weston! Set back from Newtown Turnpike on a secluded, level 1.33 acre lot, this exceptionally well maintained 3 bedroom, 2 full bath ranch offers 1,332 square feet of comfortable single level living with hardwood floors throughout and a detached two car garage. Ideally located near the Saugatuck Reservoir, Merritt Parkway, and Devil's Den Nature Preserve, the property is ready for its next owner's vision. Thoughtful updates could transform the existing home into a beautiful retreat, while the generous lot may offer exciting possibilities for expansion, including a potential second story addition or new construction, subject to town approvals. Surrounded by impressive neighboring homes, the possibilities here are substantial. Whether you're looking to renovate, expand, build new, or simply create your dream home while enjoying convenient single level living, this Weston property offers a rare combination of location, privacy, land, and potential.

261 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 Ln, Weston

$2,000,000

5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24204750 MLS

Refreshed and gorgeous, 30 Soundview Farm Road is a timeless Nantucket-style colonial in one of Weston's most desirable locations. Designed by renowned Fairfield County architect Michael Greenberg, this home blends classic elegance with a layout made for today's lifestyle. Flooded with natural light, brand-new light hardwood floors lend an air of coastal Connecticut, all tucked away on a private cul-de-sac. The grand entry is flanked by a formal dining room and living room, both perfect for holiday entertaining. The bright, airy kitchen features a breakfast bar, large dining area, and abundant counter space and storage. It opens to a family room anchored by a wood-burning fireplace encased in natural stone, plus a stylish wet bar with brand-new appliances. A cozy den or guest room with a private bath completes the first floor. Upstairs, the primary suite is a true retreat with high ceilings, two walk-in closets, a luxurious en-suite bath, and a balcony overlooking the grounds, plus an adjoining room perfect for a home office or sitting area. Three additional en-suite bedrooms offer comfort and privacy for the whole family. The partially finished lower level adds versatility as a gym and recreation space. Set on beautifully landscaped grounds bordering Aspetuck Country Club, 30 Soundview Farm Road offers privacy, timeless design, and unmatched lifestyle in one of Weston's most sought-after neighborhoods.

30 Soundview Farm Rd, Weston

$199,999

ACTIVE Status ⋅ 24204000 MLS

Tucked at the end of a peaceful cul-de-sac in Weston, this private 2-acre lot is a builder's blank canvas in one of Fairfield County's most coveted communities. The property offers a blank slate for builders and buyers ready to bring their own plans to life, free from the constraints of an existing design. Just minutes from schools, shopping, dining, and major commuting routes, this is a rare chance to create something truly your own in one of the area's most sought-after in-town locations.

354 Good Hill Rd, Weston

$1,100,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24198647 MLS

Imagine a storybook Cape along a babbling brook, surrounded by overflowing hydrangeas and mature plantings... this inviting lower Weston home feels like a private English country refuge. Pass through the white driveway gates, and you'll admire the classic cottage charm complete with new cedar roof. Inside, abundant natural light streams through multiple skylights, oversized windows, and French doors. The open living room with gas fireplace, dining room and refreshed kitchen flow easily for everyday living and entertaining. A first-floor primary bedroom offers convenient one-level living, with two additional bedrooms and a full bath upstairs. A cozy den offers space to relax, while a bonus room is flexible as a home office or mudroom. Multiple closets and a walk-up attic over the garage provide excellent storage. Outside, a screened porch and secluded, fenced patio framed by mature perennials invite you to relax, dine, and enjoy balmy summer evenings, while the brook adds to the bucolic setting. Set on just under an acre, the home offers a wonderful sense of peace and privacy. Recent updates include a refreshed kitchen and bathrooms, plus exterior paint. Weston offers excellent schools and a location just minutes from Westport's shopping, restaurants and beaches, with the train station to NYC is approximately 15 minutes' drive. Move-in ready with a quick closing available... book your showing and prepare to be charmed!

24 Good Hill Rd, Weston

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