Weston Real Estate

Welcome to Weston, Connecticut – a picturesque town nestled in the heart of Fairfield County, where tranquility meets sophistication. Known for its stunning landscapes and rich natural beauty, Weston offers a serene escape from the hustle and bustle of city life, all while being conveniently located just a short drive from the vibrant urban centers of New York City and Stamford.

With its sprawling estates, lush greenery, and charming neighborhoods, Weston is often regarded as one of Connecticut's hidden gems. The town boasts an impressive array of outdoor recreational opportunities, including hiking trails, parks, and the scenic Saugatuck Reservoir, perfect for nature enthusiasts and families alike. Residents enjoy a strong sense of community, with various local events and activities that foster connections among neighbors.

Weston is also home to some of the state’s top-rated schools, making it an ideal place for families seeking a nurturing environment for their children. The town’s commitment to education is evident, with a focus on academic excellence and a wide range of extracurricular activities.

In addition to its natural beauty and educational opportunities, Weston features a quaint downtown area with charming shops, gourmet restaurants, and local markets, providing everything you need just around the corner. Whether you’re looking to enjoy a peaceful day in nature, engage in community activities, or simply relax in a luxurious home, Weston offers an unparalleled quality of life that is hard to resist. Come discover the charm of Weston – your dream home awaits in this idyllic Connecticut town!

Newest Listings in 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

$1,050,000

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 and side entrance to the house through a mudroom and half bath. Off the kitchen is a bright sunroom also with sliders to the deck. The main level also includes an office with builtins, 3 large bedrooms plus a primary with builtins, ensuite bath and huge walk-in closet. The walkout lower level has a big rec/play/family room with fireplace, a full kitchen and 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 and mature trees and 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 ⋅ COMING SOON 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

$1,065,258

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24191063 MLS

"A rare retreat where nature, comfort, and craftsmanship come together in perfect harmony." Enter through electronic gates,experience quiet & calm & feel as though you've stepped into another world. This charming 2-bedroom,2-bath cottage welcomes you w/warmth, character & timeless appeal. Inside,you'll discover the results of thoughtful renovations & meticulous upgrades completed over the years. Aside from the main house--2 additional structures. Each room & outbuilding possess its own distinctive charm & function. Above the garage, a versatile 624+/- sq.ft. studio loft offers the perfect setting for either home/office/gym/studio or recreation room & is complete w/sauna,gas fireplace & abundant storage. The detached 204+/- sq.ft. studio office showcases soaring vaulted ceilings w/cedar & hemlock beams,rich pine floors,gas fireplace, baseboard heating & wrap around wood deck w/built-in seating-- overlooking a tranquil pond. The sun-filled kitchen features premium new appliances, custom cabinetry & new tile heated floors. The primary suite offers vaulted ceilings,revamped walk-in closet & private deck complete w/hot tub. The spacious primary bath is a spa-like retreat. Both rooms have access & views to the spacious backyard. Set on nearly 2 acres of beautifully landscaped grounds. Privately tucked away off Georgetown Road &bordering the protected open space of the Honey Hill Preserve. More than a home-it's a lifestyle.

131 Georgetown Rd, Weston

$1,369,900

5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191446 MLS

Thoughtfully sited high above Aspetuck Country Club's picturesque 16th fairway, this 5-bedroom, 4-bath residence offering over 5,300+ square feet was curated from the ground up to celebrate its extraordinary setting. Walls of glass, soaring vaulted ceilings, skylights, and multiple decks were thoughtfully designed to capture the ever-changing play of natural light-from the first rays of sunrise to the soft glow of moonrise-while framing breathtaking panoramic vistas that extend well beyond the fairway. Here, the eye is drawn to long-distance views that seem to stretch for miles, creating a living backdrop that transforms beautifully with every season. At the heart of the home, the centrally located eat-in kitchen opens to a spacious great room, creating an inviting gathering space for family and friends. Enjoy entertaining from expansive decks, where indoor & outdoor living blend seamlessly. However, the one-of-a-kind private indoor pool pavilion-an extraordinary year-round retreat for swimming, entertaining, recreation, fitness, and relaxation that sets this property apart from virtually any other in the area. 2-striking granite fireplaces add warmth & architectural character to the gracious living and dining spaces. All 5bd's are conveniently located on the main level, including the spacious primary suite with a balcony and a retro-inspired bath featuring a sunken soaking tub & separate shower +4 additional bd's of which have private balconies with stunning views!

4 Aspetuck Hill Ln, Weston

$1,035,000

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24115297 MLS

Welcome to 49 Blue Spruce Circle, a sun-drenched contemporary colonial nestled on two picturesque acres of mature trees and vibrant flowering plants. Boasting 3,297 square feet of versatile living space, this 4-bedroom, 3.1-bath home features a unique, airy layout designed to maximize natural light at every turn. The heart of the home centers around an inviting, open floor plan that flows effortlessly to the expansive back deck-perfect for indoor-outdoor entertaining or enjoying peaceful woodland views. Relax on the sweet front porch, or retreat to the upper level, where you will find the private primary suite complete with a full bath and walk-in closet. Directly adjacent to the primary is a fantastic, light-filled studio loft, offering a creative sanctuary for an art studio, home office, or additional recreation space. Additional features include a fully finished 1,430sf walk-out basement providing endless possibilities for recreation, along with convenient interior access to the 2-car garage. While being Sold AS-IS, this exceptional 2 acre property with a fully fenced backyard represents an incredible opportunity to bring your personal touch and updates to a truly special Weston retreat.

49 Blue Spruce Cir, Weston

$1,299,000

5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190123 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

$1,349,000

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 at a home that abuts Aspetuck Land Trust for privacy and nature access.

26 Hill Farm Rd, Weston

$1,399,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189016 MLS

Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the original windows and hand-laid stone floors to the reclaimed shiplap walls and solid wood doors, every detail honors the home's 1959 roots with modern systems and design. A recent full-scale renovation touched virtually every system in the home - HVAC, tankless water heater, plumbing, electrical, kitchen, baths, flooring, and millwork -move in with confidence and none of the guesswork of an older home. The main level offers the open, connected layout today's buyers are searching for: a flowing family, living, and dining space anchored by three wood-burning fireplaces, a dedicated home office, and a bright four-season sunroom perfect for year-round enjoyment. The kitchen is a true showpiece, featuring marble countertops and a professional-grade appliance suite, ideal for both everyday living and entertaining. Upstairs, the primary suite features a striking, spa-inspired wet-room bath with designer fixtures, offering a private retreat at the end of the day. Three additional bedrooms, a convenient upper-level laundry, and a second family room round out the second floor - giving families room to spread out and gather alike. This is a rare opportunity to own a fully updated classic on a beautiful piece of Weston property - schedule your private showing today.

235 Newtown Tpke, Weston

$2,200,000

5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24187814 MLS

Bring your vision to life in the heart of Weston with this rare opportunity to collaborate with a premier local builder. Sited on a sprawling, private 2.1-acre lot, this sophisticated new construction offers 4,500 square feet of meticulously designed living space, including a finished 900-square-foot lower level. The heart of the home is an expansive chef's kitchen that flows seamlessly into the dining room and a sun-drenched living area. Large windows frame picturesque views of the lush, private acreage, creating a stunning backdrop for daily life. The main floor also features a thoughtful guest suite with a full bath, perfect for visitors or a quiet home office. Upstairs, the primary suite serves as a true sanctuary, complemented by three additional well-appointed bedrooms. With five bedrooms and five bathrooms in total, the layout provides exceptional space and privacy. Outside, the three-car garage and vast backyard provide plenty of room for a custom pool or outdoor oasis. The property and septic are specifically designed to accommodate an ADU if desired, offering incredible flexibility. Because construction is in the early stages, you can step in now to select finishes and personalize the aesthetic. Looking for just the land? The lot is also available to purchase separately (see MLS#24180742). Move into a home uniquely yours, set against a backdrop of natural beauty.

96 Georgetown Rd, Weston

$1,599,000

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24178099 MLS

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 with expansive windows framing sweeping lawn views and stunning western sunsets. At the heart of the home, a renovated kitchen with a large island flows into the dining and living areas, anchored by two wood-burning fireplaces. With four bedrooms and 3 full baths, the layout provides exceptional flexibility, including a dedicated home office and additional flex space perfect for a fitness studio or creative retreat. The primary suite continues the aesthetic with oversized windows overlooking the private grounds. The property transforms into a private resort with an expansive wrap-around deck and a spectacular 40x20 heated gunite pool. A private tennis court adds to the recreational appeal. Enhancing the compound is a separate guest cottage featuring a great room with cathedral ceilings, a kitchenette, a gas fireplace, and two bedrooms. Thoughtfully maintained with a newer roof, whole-house generator, and EV charger, this architectural gem is located minutes from Weston Center and Westport.

9 Fall Ridge 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.