Refine Search
Map
Sort by
$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
$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
$20,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24206046 MLS
This exceptional custom shingle-style home offers an impressive combination of privacy, space and sophisticated indoor-outdoor living. A gracious wraparound porch welcomes you to the home, surrounded by gorgeous grounds and mature landscaping. The heart of the home is the expansive kitchen and family room, where walls of windows overlook the private backyard, spacious terrace, hot tub + outdoor fireplace. The dramatic family room features a vaulted ceiling, striking stone fireplace and sliders opening directly to the terrace. The generously sized gourmet kitchen is designed for both everyday living and entertaining, with an oversized center island + a wood-burning fireplace. The main living spaces flow seamlessly together, creating a warm and inviting setting for gatherings large and small. A mudroom/laundry room + attached 3-car garage complete the main level. Upstairs are 4 spacious ensuite bedrooms. The primary suite offers a private retreat with a generous bedroom and well-appointed ensuite bath. The finished lower level provides exceptional additional living space with 9-foot ceilings, a large play/recreation room, separate bonus/gym area + features a second lower-level garage with room for up to 3 additional cars-ideal for the car enthusiast or anyone seeking exceptional storage space. Residents enjoy beach rights to Westport's Compo Beach, Ideally located just 2 miles from Weston schools and town center. Enjoy Weston living at its best.

25 Alwyn Ln, 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
$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
$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
$11,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24202959 MLS
Light-filled, beautifully renovated and wonderfully versatile, this striking Weston 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. Also listed for SALE.

158 Steep Hill 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
$2,750,000
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
$1,880,000
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
$5,400
3 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24199856 MLS
Set in a peaceful country setting surrounded by woods, a pond and a meandering stream, this light-filled home offers an easy, open layout and beautiful views of nature from nearly every angle. The spacious living room features a fireplace and overlooks the pond, while the renovated kitchen has all-new stainless steel appliances. Updated baths and hardwood floors throughout add to the home's fresh, move-in-ready feel. The generous primary suite includes a private bath, and the third bedroom works well as a guest room, home office or nursery. Outside, the rear patio overlooks the in-ground pool and pond, creating a wonderful spot to relax, entertain and take in the natural surroundings. Bird lovers will especially appreciate the abundant wildlife, with frequent sightings of herons, hawks, owls and songbirds. A special Weston setting with convenient access to Westport, Metro-North, beaches, shopping and dining.

17 Old Mill 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
$1,795,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 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 ⋅ 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
$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
$1,799,000
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
$4,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24192471 MLS
Experience the elegance and tranquility of this exquisite two-bedroom cottage nestled within a picturesque lakeside estate. Bathed in natural light, this like-new home radiates charm and luxury. Revel in the open floor plan with granite kitchen counters and newer appliances, while the spacious bedrooms offer a haven of comfort. Discover quality finishes, high ceilings, and gorgeous hardwood floors throughout. Privately situated on the second floor (above the garage), this one-level home boasts a private entry, washer/dryer and garage space for your convenience. Enjoy the serenity of the surroundings from the large deck accessed through French doors in the living room and dining area, offering all seasons beautiful lake views. Immerse yourself in the meticulously maintained gardens and surrounding trees, creating a truly serene ambiance. Escape the hustle and bustle without sacrificing convenience, as downtown Westport's vibrant attractions are a mere 15-minute drive away. Creditworthy applicants with stellar references are invited to seize this exceptional opportunity. No pets, no smokers, no exceptions. Live in blissful harmony in this idyllic retreat.

102 Ladder Hill Rd N Unit Cottage, 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
$1,369,900
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
$899,000
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
$1,250,000
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
$1,100,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24189056 MLS
The Weston Cottage-where timeless charm, remarkable history, and tranquil riverfront living come together. Nestled along the river on the coveted Weston/Westport border, this beautifully updated 3-bedroom, 2.5 bath home offers a rare opportunity to own a piece of Connecticut history. Famously known as the retreat of legendary actress Bette Davis, the cottage became the setting for the true story that inspired the hit play Me and Jezebel, after Davis unexpectedly stayed for 32 unforgettable days. Today, this captivating home blends historic character with modern comfort. The renovated kitchen features a Wolf range, Bosch column refrigerator, and inviting marble fireplace, while all three bathrooms have been tastefully updated. Fresh interior and exterior paint, new lighting, and custom built-ins completed in 2025 enhance the home's move-in-ready appeal. Wake to the soothing sounds of the river, enjoy peaceful outdoor living, and experience the privacy and beauty of this exceptional setting just minutes from the shopping, dining, beaches, and train station in Westport. Whether you're searching for a full-time residence or a weekend escape, The Weston Cottage offers an extraordinary lifestyle in one of Fairfield County's most desirable locations.

78 River Rd, 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
$1,750,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24181401 MLS
Tucked away on a coveted lower Weston cul-de-sac, this beautifully renovated colonial offers the rare combination of privacy, style, and resort-inspired living. Thoughtfully updated by the current owner, the home is truly turnkey and ready for its next chapter. Sun-filled interiors showcase sophisticated finishes and an effortless flow for both everyday living and entertaining. The renovated kitchen, appointed with stone countertops and premium appliances, opens to a bright sunroom overlooking the property. A dramatic family room with soaring cathedral ceilings, fireplace, and wet bar serves as the heart of the home, while walls of windows fill the space with natural light. The luxurious primary suite is a true retreat, featuring a cathedral ceiling, dual walk-in closets, and a spa-like marble bath. Additional bedrooms are generously sized, and the finished lower level offers exceptional flexibility with a guest bedroom, full bath, and direct access to the outdoor entertaining areas. Outside, the property unfolds into a private oasis anchored by a gunite pool and expansive grounds. A former Har-Tru tennis court remains on the property, presenting an opportunity for restoration or reimagining to suit your lifestyle. Beautifully sited in one of Weston's most sought-after neighborhoods, this special offering is just minutes from award-winning schools, downtown Westport, Metro North, shopping, dining, and beaches.

32 Silver Ridge Cmn, Weston
$1,399,995
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24186444 MLS
Welcome to 11 Hunt Lane! This charming Colonial delivers lots of space and flexibility while situated at the end of a tranquil double cul-de-sac in Lower Weston, near the Westport line. Perfect for entertaining, the sun-filled, spacious interior boasts excellent flow. Enter a charming two-story foyer flanked by a living room with fireplace and dining room with wet bar and sliders to a beautiful backyard deck. The open floor plan also connects to a family room leading to the New eat-in kitchen with quartz countertops providing ample workspace and additional storage. The spacious laundry room features a utility sink and mudroom access entry from the kitchen and garage. Above the garage, an enormous office/rec room with built ins, full bath and walk-in closet offering the potential for guest quarters, an au pair or in-law suite. Expansive basement with Large Cedar closet provides additional storage. The private, fully landscaped yard with mature plantings backs up to open space offering peace and serenity while still being close to Merritt, I-95, train stations, beaches, and highly regarded Weston schools.

11 Hunt Ln, Weston
$11,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24184585 MLS
A rare opportunity for lovers of contemporary design-the architect-designed Glass House of Weston is available for rent. This renovated home boasts an open floorplan flooded w/natural light from floor-to-ceiling windows and skylights, offering serene views of its well-maintained natural surroundings, lush foliage, and striking rock outcroppings. The LR features soaring ceilings, mahogany windows, and a stunning natural stone fpl, flowing seamlessly into the dining area, Kit, and FR. The Kit is a showpiece w/a domed skylight, custom Italian cabinetry, German appliances, carrera marble countertops, and a stainless steel peninsula. A Brazilian ipe wood terrace extends from the Kit and living area, floating in a canopy of trees w/a creek below. The ground floor master suite is newly renovated w/white oak flooring, expansive views through a new wall of windows w/electronic solar shades, and designer lighting. The ensuite features a free-standing tub and curbless walk-in shower for accessibility. Upstairs, you'll find four additional bedrooms, two w/floor-to-ceiling corner windows, plus two modern bathrooms w/skylights. A finished basement offers flexible space for recreation, while a 2-car garage provides direct home access. Meticulously upgraded over the last five years, the home includes new mechanicals, a security system, and enhanced exterior lighting. Offered for a minimum one-year lease, with preference for multi-year tenants. Furnishing options are flexible.

112 Birch Hill Rd, Weston

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.