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3 Weston Rd, Weston
$1,149,000
4 Beds ⋅ 3 Baths ⋅ 24203719 MLS
Completely renovated storybook cape on the Saugatuck River, just over the Westport line. This home offers a rare combination of privacy, timeless character, and spectacular waterfront living. Beautifully landscaped, the property captures tranquil water views from inside and out. Extensive improvements include a new septic, windows, electrical, roof, Hydro cell/HVAC and more with a detailed list provided. The gracious living room is anchored by an impressive stone fireplace and enhanced by vaulted ceilings, exposed beams and a striking new picture window overlooking the river. The vaulted dining room features a bay window, skylight, and sliders opening to the brick patio-perfect for entertaining or enjoying the peaceful setting. The main level offers two bedrooms with a Jack-and-Jill bath, plus a spacious en-suite bedroom that provides exceptional flexibility as a first-floor primary suite, family room, or private guest retreat. A beautifully renovated kitchen with refinished hardwood floors complete the main level. Upstairs, the elegant primary suite has been thoughtfully remodeled and features beautiful hardwood floors and a spa-like bath with vaulted ceiling, custom wainscoting, steam shower, whirlpool tub, and Corian vanity. Additional amenities include whole-house generator, new laundry, and detached two-car garage. Weston offers excellent schools and ideally located minutes from Westport's celebrated dining, shopping and beaches. Magical!

3 Weston Rd, Weston
26 Pent Rd, Weston
$2,250,000
4 Beds ⋅ 6 Baths ⋅ 24208616 MLS
Gorgeous & Beautifully Renovated Riverfront Retreat along the western banks of the Saugatuck River bordering nearly 1,800 acres of protected nature at Devil's Den Preserve. This Craftsman-style home offers refined living, privacy & immersion in nature. Surrounded by a wildlife sanctuary, the property is a haven for cranes, hummingbirds, an occasional bald eagle & an abundance of native bird species creates a peaceful setting that feels worlds away while remaining close to everything Weston has to offer. Renovated with attention to detail, the home blends Craftsman character with sophisticated modern amenities. Expansive windows bring the landscape indoors with tranquil views. A two-sided fireplace provides a dramatic focal point, seen from both the living room & kitchen. One of the home's most distinctive spaces is the Family Room, affectionately known as the "Tree House". Perched among the treetops, this special retreat offers a spectacular view & a peaceful place to read, gather & enjoy each season from above the canopy. A wrap-around deck, the heated Gunite pool, hot tub & firepit create spaces for entertaining, relaxing & enjoying the natural beauty of the property. Features/updates include Anderson windows, radiant heated floors, newer boiler 2018, new indirect water heater 2023, updated Gunite pool & patio 2025, a leaded copper standing-seam roof, a Whole Home Heavy Duty Generaor adds peace of mind, exterior EV/RV charging station & more! See full list of improvements.

26 Pent Rd, Weston
11 Soundview Farm, Weston
$1,495,000
5 Beds ⋅ 5 Baths ⋅ 24209506 MLS
Welcome to 11 Soundview Farm, a stunning contemporary residence offering a serene and private escape in one of Weston's most coveted cul de sac neighborhoods. Featuring approximately 4,500+ square feet of thoughtfully designed living space, this 5-bedroom, 4.5-bath home perfectly balances architectural flair with everyday comfort. Enjoy sun-drenched principal rooms, soaring ceilings, and an effortless flow for both intimate living and grand entertaining. Nestled on a peaceful, scenic lot surrounded by mature trees, this property delivers the ultimate Connecticut lifestyle while remaining just minutes from top-rated schools, local parks and commuting routes. Your private sanctuary awaits!

11 Soundview Farm, Weston
108 Old Farm Rd, Weston
$2,600,000
5 Beds ⋅ 7 Baths ⋅ 24208892 MLS
Nestled on two private acres and bordered by more than 1,700 acres of protected nature preserve, this newly constructed estate in Weston delivers an uncommon blend of privacy and craftsmanship. Five generously proportioned bedrooms, each with its own en suite bath, offer refined comfort for family and guests alike, while a three car garage with soaring ceiling height stands ready for a car lift, a rare luxury for the discerning collector. At the heart of the home, a fully custom chef's kitchen commands attention with sleek quartz countertops and a professional grade suite of Wolf and Sub-Zero appliances, framed by rich white oak flooring that flows seamlessly throughout. Thoughtfully placed built in track lighting accentuates the home's clean, architectural lines at every turn. Descend to the lower level and discover a dedicated home theater, an indulgent retreat built purely for cinematic escape. Just minutes from Branchville Train Station, this address offers effortless access to Manhattan without ever compromising the tranquility of its wooded, preserve backed setting. Offered at $2,600,000, this is new construction elevated: opulent in detail, exacting in craftsmanship, and ready to welcome its first owner.

108 Old Farm Rd, Weston
10 Weddington Ln, Weston
$1,850,000
5 Beds ⋅ 6 Baths ⋅ 24197426 MLS
*THANK YOU FOR YOUR INTEREST: SELLER REQUESTS HIGHEST/BEST OFFERS BY 5PM MONDAY 9/28/26* Set on a premier cul-de-sac across from the beautiful grounds of the prestigious Aspetuck Valley Country Club, this gorgeous all-brick Colonial makes a spectacular first impression. A new circular driveway through the landscaped 2 acres leads to this architecturally distinctive custom home. Varied roof lines, bay windows, copper accents, distinctive chimneys & established landscaping set the tone for this refined home. Double doors lead to the sun-filled foyer w/floating staircase, powder rm & walk-in coat clst. Many rms feat. soaring cathedral-height ceilings, incl the LR & fam rm, each w/ fpl & oversized windows. DR w/tray ceil. Updated EIK w/fresh white cabinetry & new appls incl dbl ovens has a breakfast area w/bay window & garden views, plus a mudroom leading to the 3-car garage. The exquisite library/office has a cathedral ceil, 3rd fpl, cstm built-ins & bay window. 5 BR (4 per town) beginning with a main level guest/in-law/staff/den w/adjacent full bath. Upstairs, an open & gracious landing leads to lrg BRs. The primary suite is a stunning space with king-size BR, sitting nook, glorious windows, a lrg marble bath, walk-in clst & two extra storage spaces. The finished lower level w/high ceilings has a rec/play room/gym area, wet/snack bar, full bath and massive storage rooms or space for additional future finishing. The stone terrace leads out to level lawns and enchanting gardens.

10 Weddington Ln, Weston
24 Langner Ln, Weston
$1,850,000
6 Beds ⋅ 5 Baths ⋅ 24207679 MLS
Set behind charming stone walls on flat, usable land, this beautiful home offers exceptional space for everyday living and entertaining, just minutes from Weston's award-winning schools. The heart of the home features a large chef's kitchen that opens seamlessly to a cozy sunken family room. Sliding glass doors lead out to a stone patio overlooking a spacious backyard with ample room for a pool. The main level also includes a private bedroom suite-ideal for guests or an au pair. The second floor hosts a primary suite featuring a fireplace, an attached home office, and a newly renovated bath. Three additional bedrooms, two full baths, and a versatile playroom complete the upper level. Downstairs, the finished lower level provides flexible rec space, a gym, a full bath, and abundant storage. Don't miss this great Weston home.

24 Langner Ln, Weston
1 Greenlea Ln, Weston
$1,299,900
5 Beds ⋅ 3 Baths ⋅ 24207576 MLS
Stunning, modern renovation on this spacious home ideally situated steps to the Westport/Weston line in a very convenient lower Weston location. The open-concept interior features soaring vaulted ceilings, generously sized rooms, a fireplace, modern glass railings, and walls of windows that fill the home with natural light. The brand new modern kitchen is designed to impress with new modern cabinetry, a large center island, and premium Thermador appliances. Newly installed hardwood floors, LED recessed lighting, fresh interior and exterior paint, new trim and new interior doors add to the stylish transformation. The main level also offers four bedrooms, including a spacious primary suite with a stunning remodeled bath featuring a double vanity, oversized shower stall and soaking tub. An additional renovated full bath and convenient main level laundry complete this floor. The expansive finished walk-out lower level provides exceptional additional living space or a perfect potential in-law/au pair. Featuring a family room with a fireplace, fifth bedroom, another remodeled full bath, large recreation room and versatile bonus room. Corner lot with large private yard and grounds. Additional improvements include a new HVAC system, Navien hot-water heater, new modern glass garage doors and front door, new Trex decking and a roof completed in 2025. Gas heat, gas hot water and city water for added convenience. Septic redone in 2009. Nothing to do but move in and enjoy.

1 Greenlea Ln, Weston
46 Valley Forge Rd, Weston
$2,000,000
3 Beds ⋅ 4 Baths ⋅ 24200625 MLS
WOW! Gorgeous MID CENTURY MODERN nestled on over 300 feet of direct Saugatuck river frontage! Enter to sweeping views of the leafy bucolic scenes of nature through the walls of glass on both levels. Light and bright white kitchen opens to lovely deck for effortless entertaining. The inviting living room has a stunning floor to ceiling fireplace for cozy fall evenings. The primary bedroom suite is complete with a spa like bathroom, walk in closet, laundry and convenient office --ALL with RIVER VIEWS. The lower level is a comfortable relaxing family room, two bedrooms and full bath with direct access to the slate patio--with RIVER VIEWS. Thru a separate entrance in the back there is a newly finished sauna and shower. The cottage has endless possibilities...home office, work out space, separate lounge area...AND of course has gorgeous RIVER VIEWS!!! Pool permit has been approved; renderings attached just steps from the new sauna/shower. A pool would be a great addition 46 Valley Forge, a stunning riverfront retreat!

46 Valley Forge Rd, Weston
32 Bernhard Dr, Weston
$3,200,000
4 Beds ⋅ 6 Baths ⋅ 24206702 MLS
Welcome to an exceptional luxury retreat in the heart of Weston, where privacy, elegance, and resort-style living come together in a truly remarkable setting. Privately positioned at the end of a long driveway on a desirable cul-de-sac, this distinctive estate offers an extraordinary lifestyle with sophisticated indoor and outdoor spaces designed for both grand entertaining and everyday enjoyment. Step outside to your own private resort, featuring a gunite heated swimming pool, jacuzzi, expansive stone patio, outdoor shower and beautifully appointed outdoor entertainment area with a fully equipped outdoor kitchen. Surrounded by mature landscaping and tranquil natural beauty, the outdoor spaces create the perfect setting for al fresco dining, summer gatherings, or quiet evenings under the stars. The residence offers 5 bedrooms, 5 full bathrooms, and 3 half bathrooms, along with an impressive array of thoughtfully designed spaces, including a billiard room, wine cellar, exercise room, recreation room, office, sunroom and family room. An additional attic level offers a finished room and versatile bonus space, providing even more room for guests, hobbies, or personal use. Every detail reflects a commitment to comfort, entertaining, and refined living. A 3-car garage adds convenience and ample space for vehicles and storage. From the grand approach and peaceful cul-de-sac setting to the exceptional amenities and expansive indoor-outdoor living spaces.

32 Bernhard Dr, Weston
5 Aspetuck Gln, Weston
$2,449,000
5 Beds ⋅ 7 Baths ⋅ 24193559 MLS
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 and much more.

5 Aspetuck Gln, Weston
38 Ravenwood Dr, Weston
$679,900
3 Beds ⋅ 2 Baths ⋅ 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. Some images attached are virtually rendered.

38 Ravenwood Dr, Weston
36 Old Orchard Dr, Weston
$2,189,000
5 Beds ⋅ 5 Baths ⋅ 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
158 Steep Hill Rd, Weston
$1,795,000
5 Beds ⋅ 4 Baths ⋅ 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
143 Old Hyde Rd, Weston
$1,695,000
6 Beds ⋅ 4 Baths ⋅ 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 entertain your guests on the wrap-around deck. 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
227 Newtown Tpke, Weston
$1,595,000
4 Beds ⋅ 4 Baths ⋅ 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
261 Newtown Tpke, Weston
$599,900
3 Beds ⋅ 2 Baths ⋅ 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
16 Katydid Ln, Weston
$3,075,000
5 Beds ⋅ 6 Baths ⋅ 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
30 Soundview Farm Rd, Weston
$2,000,000
5 Beds ⋅ 7 Baths ⋅ 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
21 Deepwood Rd, Weston
$1,249,000
5 Beds ⋅ 3 Baths ⋅ 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
181 Georgetown Rd, Weston
$1,249,000
4 Beds ⋅ 4 Baths ⋅ 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
6 Old Orchard Dr, Weston
$2,150,000
4 Beds ⋅ 6 Baths ⋅ 24201533 MLS
Nestled on over 3 breathtaking acres with over 500 feet of riverfront on the West Branch of the Saugatuck, 6 Old Orchard Drive offers an unparalleled setting, abundant natural light, and a rare opportunity for its next owner. Featuring solid bones, a sprawling open layout, and unbeatable water views, this home is move-in ready today, yet holds incredible potential for custom aesthetic updates to make it your ultimate forever home. Whether you choose to simply update a few finishes over time or embark on a complete design transformation, the foundation here is exceptional. The main level has numerous formal and informal spaces, featuring a sunlit kitchen, a family room, an elegant dining room, and two separate living spaces-each with its own fireplace and tranquil river views. There are four spacious ensuite bedrooms, plus a soaring second-story great room with cathedral ceilings, oversized windows, and a full bath (easily converted to a 5th bedroom suite or primary retreat). Outside, the property is pure magic: lush lawns, mature trees, an expansive deck, and a stone patio surrounding a pristine gunite pool-all set against the serene backdrop of the river. If you've been searching for a setting you can't replicate and a home you can tailor to your own taste, this Weston paradise is ready for its next chapter.

6 Old Orchard Dr, Weston
81 Trails End Rd, Weston
$1,549,900
6 Beds ⋅ 6 Baths ⋅ 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
15 Birch Hill Rd, Weston
$1,795,000
5 Beds ⋅ 5 Baths ⋅ 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
79 Cavalry Rd, Weston
$2,199,000
5 Beds ⋅ 8 Baths ⋅ 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
10 Dragonwood Ln, Weston
$6,500,000
4 Beds ⋅ 5 Baths ⋅ 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
7 White Oak Ln, Weston
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 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
103 Steep Hill Rd, Weston
$1,000,000
4 Beds ⋅ 3 Baths ⋅ 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
4 Aspetuck Hill Ln, Weston
$1,369,900
5 Beds ⋅ 4 Baths ⋅ 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
26 Hill Farm Rd, Weston
$1,250,000
6 Beds ⋅ 4 Baths ⋅ 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
235 Newtown Tpke, Weston
$1,299,900
4 Beds ⋅ 3 Baths ⋅ 24189016 MLS
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

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