Weston Homes with Contemporary Style

Welcome to Weston, Connecticut—a picturesque town nestled in the heart of Fairfield County, where the charm of suburban living meets the allure of contemporary design. Known for its lush landscapes and serene environment, Weston offers a tranquil retreat just a stone's throw from the bustling city life of nearby Stamford and Norwalk.

Weston is celebrated for its exceptional school system and tight-knit community, making it an ideal location for families seeking a nurturing environment. With sprawling parks, nature trails, and recreational facilities, residents enjoy an active lifestyle surrounded by the beauty of nature. The town’s commitment to preserving its natural resources ensures that green spaces flourish, providing a perfect backdrop for outdoor activities.

For those with a taste for modern aesthetics, Weston boasts an impressive selection of contemporary-style homes that redefine luxury living. These residences often feature open floor plans, large windows that flood interiors with natural light, and sleek designs that harmonize with the surrounding landscape. Many homes are equipped with state-of-the-art amenities, showcasing the latest in energy-efficient technology and sustainable living.

Living in a contemporary home in Weston means embracing a lifestyle of sophistication and comfort. Whether you’re entertaining guests in a spacious living area or unwinding in a beautifully landscaped backyard, these homes offer a perfect blend of style and functionality. Explore Weston’s real estate offerings and discover your dream home in this idyllic Connecticut town, where modern living meets timeless elegance.

Newest Weston Homes with Contemporary Style

$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

$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

$1,249,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24202535 MLS

Nestled at the end of a quiet cul-de-sac on two picturesque acres, this extraordinary five-bedroom, three full bath residence offers a rare combination of timeless elegance and peaceful seclusion. Overlooking a gently flowing brook, the property is surrounded by natural beauty, creating a private retreat just minutes from the vibrant shops, acclaimed restaurants, beaches, and Metro-North train station in neighboring Westport. Designed for both everyday living and effortless entertaining, the home features two luxurious primary suites, including one on the main level and a second upstairs with its own private balcony overlooking the tranquil landscape. The sleek kitchen is beautifully appointed with new countertops, while the bathrooms offer sophisticated, contemporary finishes. Brand-new Andersen windows throughout bathe the home in natural light while enhancing comfort and efficiency. Offering an exceptional balance of privacy, convenience, and refined living, this is a rare opportunity to own a truly special home in sought-after Weston.

21 Deepwood Rd, Weston

$2,250,000

4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24201533 MLS

Nestled on over 3 breathtaking acres with over 500 feet of frontage on the west branch of the Saugatuck River, this exceptional property offers the perfect blend of privacy, outdoor living and natural beauty. Surrounded by mature trees and lush lawns, the setting is nothing short of spectacular--truly one of the most beautiful in Weston. The spacious home is thoughtfully designed with an open floorplan that seamlessly connects the main living areas, making it ideal for entertaining. It features four generously sized bedrooms, each with its own private bathroom. The main level includes a large living room and a den each with a fireplace and river views, an elegant dining room, and a family room off the expansive kitchen--all flowing effortlessly from one to the next. There is a second story great room with oversized windows and beautiful views. This bright and airy room with cathedral ceilings and a full bathroom can easily be converted into a fifth bedroom. Just outside, your own private oasis awaits--an expansive deck overlooking the river, scenic landscaping, and a stone patio with gunite pool--perfect for summer relaxation or entertaining under the stars. In addition to the numerous recent improvements to the key systems of the home, the driveway has been redone and the house has been painted on the interior and exterior. Whether you're looking for a peaceful retreat or a forever home, this extraordinary property offers an unparalleled lifestyle in an idyllic setting.

6 Old Orchard Dr, Weston

$1,880,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200916 MLS

Mid-century modern, completely reimagined and taken down to the studs. Set on a private Lower Weston cul-de-sac near the Westport/Fairfield border, this striking 5-bedroom home pairs architectural character with a comprehensive, design-driven renovation. The custom walnut-and-Fenix kitchen features Dekton counters, integrated lighting, and Wolf/Sub-Zero appliances, radiant heat, custom lit cabinetry and abundant natural light. The three fully renovated baths include a spectacular spa-like primary with a soaking tub, waterfall shower, smart toilet and radiant heat. All new electrical, gas conversion, three gas fireplaces, refinished hardwoods and an exceptional walk-out lower level with custom bar bring serious luxury credentials. Outside, enjoy the deck, new pool cover, newly fenced grounds with distant views, and exceptional privacy. Sophisticated, turnkey and refreshingly unexpected, this is mid-century Weston living without the renovation project. See the Addendum and Documents for the full detailed list of completed work. It was done as a "forever home" for the current owner, who has great sensitivity for the mid-century modern vernacular.

62 Wells Hill Rd, Weston

$1,000,000

3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 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

$6,500,000

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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

$1,050,000

5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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

$1,250,000

6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24188962 MLS

Reintroduced & Reimagined! This stylish Contemporary High Ranch at the end of a serene cul-de-sac, has been renovated by Nova Design Build of NYC. Vaulted ceilings and a wall of windows bathe the home with natural light, creating a modern aesthetic with MidCentury warmth. Newly renovated kitchen with skylights, dining area and a double sided woodburning fireplace in the living room. The expansive open floorplan has a living room & dining room which gaze upon an oversized deck & private backyard. Spoil yourself in a Primary suite which features a vaulted ceiling and brand new spa bath (2026). Three additional renovated bathrooms, new roof (2026), solid custom 7.5ft doors, and custom closets elevate the home throughout. Abundant in flexibility, thanks to four bedrooms on the main level plus two more on the lower level. Lower level includes family room with fireplace, gym/5th bedroom, office/6th bedroom, renovated bath, recreation space, and updated laundry and mudroom. Enjoy a bucolic lifestyle with beautiful nature views.

26 Hill Farm Rd, Weston

Start Your Search

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.