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$1,049,000
3 Beds ⋅ 3 Baths ⋅ 24193390 MLS
Welcome to 82 Old Mill Road, the perfect balance of privacy and convenience, along with the luxury of an inground pool surrounded by bucolic landscaping. This well-maintained and spacious 3 bed, 2 1/2 bath home is perfectly situated on a secluded acre just steps from Georgetown's restaurants and shops. With almost 2,400 square feet of move-in ready living space, there is room for all. A light-filled and updated eat-in kitchen features new appliances and sliders to the generous backyard patio. Find a welcoming living room with a wood-burning fireplace and picture window, and formal dining room with built-ins. A convenient bedroom and full bath complete the first floor. Upstairs find a generous, light-filled primary bedroom with a private bathroom, and another spacious bedroom, both with ample storage. The finished basement provides even more living space with a large recreation room, wet bar, and half bathroom-perfect for movie nights, watching sports, or entertaining friends. Your outdoor oasis awaits with beautiful mature landscaping, large patio and heated gunite pool, creating a private setting for relaxing and gathering. Find more storage above the attached 2-car garage that features epoxy flooring and entrance to the sunny mudroom. Set along a private road, this opportunity to feel away from it all while close to both Georgetown and Wilton Center, is not to be missed!

82 Old Mill Rd, Wilton
$2,399,000
5 Beds ⋅ 6 Baths ⋅ 24194109 MLS
Set on a private, beautifully landscaped two-acre property, 14 Powder Horn Hill Road offers exceptional space, privacy and convenience just minutes from Wilton town center, shopping and the train. A stunning front porch creates a memorable first impression and opens to a grand entry foyer with a sweeping staircase. Inside, rich hardwood floors, generous room sizes, high ceilings and thoughtful architectural details create an elegant yet comfortable atmosphere. The spacious chef's kitchen features a large center island, Sub-Zero refrigeration and abundant workspace, flowing seamlessly into the inviting family room with coffered ceilings, a fireplace and French doors leading to the deck. Formal living and dining rooms provide ideal entertaining spaces, while a private library offers the perfect home office or quiet retreat. Upstairs, the expansive primary suite features a fireplace, luxurious bath and two exceptionally large walk-in closets. Four additional bedrooms and an oversized playroom room with a full bath offer outstanding flexibility for guests, recreation or media. The walk-out lower level is a true blank canvas, featuring impressive 9-foot ceilings, plumbing already in place for a future bathroom and endless potential to create a gym, home theater, game room, guest suite or additional living space. Outside, the flat, fenced backyard offers an ideal setting for entertaining, play and pets, with ample room for a future pool.

14 Powder Horn Hill Rd, Wilton
$949,000
4 Beds ⋅ 2 Baths ⋅ 24169858 MLS
Welcome to this inviting 4-bedroom, 2-bath Hi-Ranch, ideally situated on a quiet cul-de-sac in desirable South Wilton. Designed for comfortable everyday living and easy entertaining, the main level features a bright living room that flows seamlessly into the dining room and an updated kitchen with granite countertops, opening to a den. The primary bedroom, two additional bedrooms, and a full bath complete the main level. The lower level offers exceptional flexibility with a family room featuring a cozy fireplace, a fourth bedroom, full bath, laundry room, and convenient access to the attached two-car garage. Set on a picturesque, level property, the backyard is ideal for outdoor enjoyment with a generous deck perfect for relaxing, dining al fresco, or entertaining family and friends. Enjoy the best of both privacy and convenience with this sought-after location just minutes from Wilton's town center, Metro-North train station, shopping, restaurants, parks, and major highways, making commuting and daily errands effortless. A wonderful opportunity to make this welcoming home your own.

22 Bittersweet Trl, Wilton
$999,500
4 Beds ⋅ 3 Baths ⋅ 24192871 MLS
Located close to the Lake Club on a private secluded lot bordering Parting Brook. This home underwent a complete top to bottom remodel featuring, a stunning new kitchen, all new windows, heating and cooling system, new baths, siding, deck, etc.... 4 fireplaces, 2 car garage, walk in closet, newly paved driveway.

147 Thayer Pond Rd, Wilton
$975,000
3 Beds ⋅ 2 Baths ⋅ 24175156 MLS
Turn-key, 3-bedroom, 2-full bath split-level home set on a level 2+ acre property in a sought-after neighborhood, perfect for walking and bike riding. Enjoy direct access to Sackett State Park, offering miles of scenic trails for hiking and walking your dogs. The updated kitchen features quartz countertops, stainless steel appliances, and a breakfast bar that opens seamlessly to the dining area and spacious living room, creating an ideal layout for everyday living and entertaining. Two bedrooms share a full bath, while the primary suite offers a walk-in closet, raised ceiling with skylight, and a private full bath. The finished lower level includes a welcoming family room with a fireplace, built-in shelving, office, full bath, and walkout access to the backyard and deck. Hardwood floors throughout, a gracious entry foyer, and fresh interior and exterior paint add to the home's appeal. Solar panels help keep electric costs low. Conveniently located close to town, schools, and New Canaan, this move-in ready home offers the perfect combination of comfort, convenience, and outdoor recreation. Don't miss this exceptional opportunity!

8 Ground Pine Rd, Wilton
$1,190,000
3 Beds ⋅ 2 Baths ⋅ 24193149 MLS
Beautifully renovated and impeccably maintained, this sun-filled 3-4 bedroom home offers timeless style, quality craftsmanship, and exceptional indoor-outdoor living on a picturesque, meadow-like property. Soaring ceilings, walls of windows, and an open, inviting layout create the perfect setting for everyday living and entertaining. The chef's kitchen features premium cabinetry, quartz countertops, a large center island, Wolf six-burner cooktop, Bosch wall ovens, and a walk-in pantry, flowing seamlessly into the beamed family room with wide-board floors, wood-burning fireplace, and French doors to an expansive stone patio complete with multiple seating areas, a custom outdoor fireplace, and spa. The main level includes two bedrooms, a renovated full bath, and a flexible den with fireplace and built-ins that can serve as a fourth bedroom or home office. Upstairs, the private primary suite features vaulted ceilings, a walk-in closet, and a beautifully appointed ensuite bath. Recent improvements include a new 50-year roof, high-efficiency propane boiler, sump pump system, renovated basement, CarbonArmor garage wall stabilization, polyaspartic garage floor coating, and fresh interior paint. Central air, whole-house generator, two-car garage, and a level driveway complete this move-in ready home, ideally located just minutes from Wilton's town center, top-rated schools, and commuting routes.

130 Blue Ridge Rd, Wilton
$1,495,000
3 Beds ⋅ 3 Baths ⋅ 24191770 MLS
In 1968 the owners purchased a 2 acre building lot and built a beautiful home and raised their family and grandchildren. Now it's time for another family to enjoy years of happiness as they did in the past. Spacious single floor living circular drive. Open front door to a large entrance leading to a formal living room and dining room. Eat-in Kitchen opens to a large family room fireplace with a wall of windows overlooking the landscaped property with pool. Master with full bath walk-in closet plus a wall of closets. Two additional bedrooms main level. Lower level with walkout sliders to covered patio A spacious playroom additional 1550 Sq Ft. with fireplace and bar area. Bath with shower and possible office/bedroom and a storage room. Two private beautifully landscaped acres, flat open play yard. Also included is a Generic generator.

70 Coley Rd, Wilton
$2,695,000
6 Beds ⋅ 5 Baths ⋅ 24193184 MLS
Few homes define a town, this is one of them. Located in the highly coveted South Wilton neighborhood, this iconic Grand Dame, originally dating to the 1830s and beautifully reimagined and expanded during the Colonial Revival of the 1930s, has been masterfully transformed from the inside out. Every inch has been thoughtfully restored and elevated by a renowned preservationist / designer, honoring its extraordinary heritage while embracing the finest comforts of modern living. Rich in character and timeless elegance, the home showcases magnificent stone fireplaces, high ceilings, hand-hewn beams, wide-plank chestnut floors, beautifully preserved millwork, designer lighting, Farrow & Ball finishes, exquisitely renovated baths, and countless bespoke details that reflect an uncompromising commitment to craftsmanship. Bathed in natural light, the spectacular living spaces are both spacious and welcoming, with walls of windows framing picturesque views in every season. The exquisite eat-in chef's kitchen and butler's pantry, with high-end appliances, light fixtures and Carrara marble, is magazine worthy! The luxurious primary suite offers a private retreat, while five additional generously scaled and beautifully designed bedrooms, charming balconies, multiple perfect office spaces and a spectacular versatile historic barn create exceptional flexibility and enduring appeal.

89 Chestnut Hill Rd, Wilton
$2,350,000
6 Beds ⋅ 6 Baths ⋅ 24185788 MLS
Built by the renowned Kellogg Brothers, this exceptional custom home showcases timeless craftsmanship, architectural elegance, and meticulous attention to detail. A circular driveway leads to a dramatic two-story foyer with Bordeaux-style Brazilian cherry parquet flooring. The gourmet kitchen is appointed with a Sub-Zero refrigerator, Viking six-burner range with griddle, pot filler, warming drawer, two dishwashers, custom cabinetry, walk-in pantry, and sliders opening to the expansive deck. The spectacular great room features soaring ceilings, a fireplace, dramatic two-story windows, extensive custom millwork, refinished hardwood floors, a brass chandelier, and sliders that seamlessly connect to the outdoor living spaces. Additional highlights include a sun-filled living room with fireplace and bow window, elegant dining room with window seat, and a richly paneled office with French doors and access to the screened porch. Outside, enjoy a heated infinity-edge Gunite pool, grotto seating area, mature landscaping, and manicured privet hedges creating an exceptional private oasis. The property also offers direct access to scenic walking trails connecting to 93-acres of the Wilton Land Trust and Harris Smith Preserve. The home offers six bedrooms, including five upstairs and one on the walk-out lower level. The finished lower level features a recreation room with a wood-burning fireplace. Grey Rocks truly depicts luxury, comfort, and timeless design.

88 Grey Rocks Rd, Wilton
$1,349,000
4 Beds ⋅ 4 Baths ⋅ 24187681 MLS
Nestled on two private acres in a desirable South Wilton neighborhood, this inviting home offers a rare combination of privacy, comfort and exceptional indoor-outdoor living. At the heart of the home is a dramatic cathedral-ceiling great room that serves as the centerpiece for everyday living and entertaining. Adjacent living spaces flow naturally to a spacious screened porch with a cedar ceiling and an expansive 36-foot cedar deck overlooking the pool, patios, and mature landscaping. Together, these spaces create a private backyard retreat designed for gathering with family and friends, outdoor dining, and relaxing throughout the seasons. The kitchen features stone countertops, quality cabinetry and views of the backyard and pool, keeping the home's most important living spaces connected to the outdoor setting. The primary suite includes an updated bath, while additional bathrooms have been thoughtfully refreshed for modern comfort. A welcoming living room with a wood-burning fireplace and a spacious dining room provide comfortable gathering spaces for family and guests. A walk-out lower level with a full bath has direct access to the backyard and pool area enhancing the home's versatility. Ideal for a recreation room, media, home office, fitness area, or guest space. Surrounded by mature landscaping and set well back from the road, the property offers a sense of privacy while remaining just minutes from Wilton Center, award-winning schools, Metro-North train, I95, Merritt.

47 Pine Ridge Rd, Wilton
$825,000
4 Beds ⋅ 3 Baths ⋅ 24190698 MLS
Nestled on a peaceful 1.12-acre lot along a quiet South Wilton street, this property offers the perfect balance of privacy and convenience. Surrounded by mature trees and natural beauty, the setting provides a serene retreat while still being just minutes from everything Wilton has to offer. Ideally located with easy access to shopping, restaurants, schools, parks, and major commuting routes, this home combines a tranquil lifestyle with everyday convenience. Whether you're enjoying the expansive yard, entertaining outdoors, or simply appreciating the peaceful surroundings, this is a wonderful opportunity to enjoy the best of South Wilton living.

65 Whipple Rd, Wilton
$2,495,000
4 Beds ⋅ 4 Baths ⋅ 24190319 MLS
Bring your vision of the perfect home to life with this rare opportunity to build a bespoke Contemporary Farmhouse by an HOBI award-winning luxury home builder. Every detail will be thoughtfully considered when constructing a masterpiece tailored entirely to your lifestyle. From the foundation to the finishes, only the finest top-of-the-line materials and premium appliances will be used. You will enjoy a seamless, highly collaborative design process, working hand-in-hand with the builder to ensure every single detail is exactly as you desire. The exterior will be equally stunning, featuring a professional landscaping design package complete with foundational plantings to welcome you home. Don't just buy a house-collaborate on your ultimate dream home.

30 Cobbs Mill Rd, Wilton
$1,849,000
4 Beds ⋅ 4 Baths ⋅ 24189488 MLS
Exceptional modern custom colonial farmhouse boasting over 3700 sq ft. Serene gardens and wrap around porch welcome you home. Tucked away on nearly 2.5 acres with lush landscaping, mature trees and stunning fire pit conversation area. Craftsmanship abounds. Elegance. Details. Bluestone. Luxury wide plank flooring. Flooded with natural light. ADA compliant features swath the main floor, including zero-entry from the five (5!) car temperature controlled garage. Perfect for a car enthusiast. First floor primary suite. Great room featuring kitchen with upscale Bosch appliances, European granite, dining and living rooms with soaring ceiling heights. Butler's pantry. Upstairs, three additional bedrooms, den, and jaw-dropping bonus room with flex space that offers unparalleled gathering, entertainment, exercise, art-studio opportunities. Parties beckon. No one will want to go home. Make this one yours! Generator should you need it. The toniest of Wilton addresses cross-sectioned with the perfect home. A backdrop for core memory-making moments. Discriminating buyers take note, 2019 build equals newer mechanicals, roof.

35 Hickory Hill Rd, Wilton
$1,995,000
4 Beds ⋅ 7 Baths ⋅ 24189849 MLS
Nestled on one of Wilton's most coveted roads, this exceptional Colonial offers timeless architecture, generous proportions, and an ideal floor plan for today's lifestyle. Step through the impressive front entrance into a gracious foyer that opens to a handsome office with custom built-ins, an elegant formal living room with fireplace, a spacious dining room designed for entertaining, and a warm, inviting sunroom. The heart of the home is the family room, anchored by a stone fireplace, soaring ceiling and surrounded by walls of windows and French doors leading to an expansive deck overlooking the beautiful level property. The well-designed kitchen features quality custom cabinetry, updated appliances, abundant workspace, and a sunny breakfast area wrapped in windows that bring the outdoors in. Upstairs, every bedroom is ensuite, including a spacious primary suite with an updated bath. An oversized add'l family room offers exceptional flexibility as a recreation room, media room, fitness space, or additional bedroom. High ceilings, oversized rooms, and quality craftsmanship throughout create a home that is both elegant and comfortable. Situated on a picturesque private lot with a potential pool site, this property offers exceptional privacy while enjoying the prestige of Nod Hill Road. Convenient to Wilton's award-winning schools, town center, and commuting routes, this is a rare opportunity to own in one of Fairfield County's most sought-after locations.

324 Nod Hill Rd, Wilton
$1,250,000
4 Beds ⋅ 5 Baths ⋅ 24189843 MLS
Nestled on a picturesque one-acre property in Wilton's desirable neighborhood, this beautifully updated Colonial offers the perfect blend of timeless charm, modern design, & exceptional functionality. The home showcases quality craftsmanship, an open-concept layout, & thoughtfully designed living spaces ideal for today's lifestyle The heart of the home is a stunning gourmet kitchen featuring premium cabinetry, quartz countertops, stainless steel appliances, center island, and seamless flow into the dining and family rooms-perfect for both everyday living and effortless entertaining. Sun-filled interiors, hardwood floors, elegant finishes, and a warm, inviting fireplace creates an atmosphere that feels both sophisticated & comfortable The spacious primary suite serves as a private retreat with a luxurious bathroom & closet space, while the additional bedrooms are generously sized. The lower level provides flexible living space ideal for a rec room, home office, fitness area, or guest suite Outside enjoy the tranquility of professional landscaping offering privacy, ample lawn space for play, and room to relax or entertain. The peaceful setting feels worlds away while remaining just minutes from Georgetown Village, Branchville Metro-North, Route 7, award-winning schools, shopping, dining, & countless outdoor recreation opportunities Move-in ready and meticulously maintained, this home delivers the perfect combination of modern comfort, quality updates, & unbeatable location

25 Sunset Hill Rd, Wilton
$3,350,000
6 Beds ⋅ 7 Baths ⋅ 24185894 MLS
Located moments from Wilton Town Center, this fully reimagined 6-bedroom, 5.2-bath residence blends timeless character with modern luxury. Set on more than two pristine acres with a designated pool site and overlooking the Silvermine River, the home has been extensively renovated, showcasing exceptional craftsmanship and thoughtful design throughout. The interior features 9-foot ceilings, Brazilian cherry floors on the main level, red oak upstairs, and custom millwork. Designer finishes, modern lighting, and integrated smart-home technology complement a spacious layout ideal for entertaining and everyday living. The lower level offers two large rooms, each with walk-out access, a fireplace, a full bath, and an additional room that could serve as a bedroom, providing flexible space for nanny or in-law use, guest quarters, recreation, or a private home office. Bespoke cabinetry, premium fixtures, and top-tier appliances elevate each room. Additional highlights include commercial-grade mechanical systems, a Kohler true full-house 48 KW generator, advanced home technology and security, and a lifetime shingle roof with warranty and copper flashing. Outdoors, refreshed landscaping, new plantings, a mahogany deck and porch, and upgraded hardscaping create a private, inviting setting for gatherings or quiet enjoyment.

112 Vista Rd, Wilton
$950,000
3 Beds ⋅ 3 Baths ⋅ 24177191 MLS
Set on over 2 private acres, this 2,800+ square foot home captures the clean lines and connection-to-nature spirit of mid-century design. A thoughtfully updated retreat (Roof, deck, garage doors, windows in primary bedroom, driveway all recently updated) just under a mile from the Cannondale train station, this is effortless commuting paired with total seclusion at home. Step inside to a dramatic living room anchored by a floor-to-ceiling stone, wood-burning fireplace (there are 4 fireplaces!) and wide plank hardwood floors that set the tone for the whole home. The open, light-filled layout flows naturally from room to room, with a renovated primary bath, updated powder room, and some fresh paint giving every space a crisp, move-in-ready feel. A private office on the main level could also serve as an occasional guestroom and the primary bedroom features a fireplace as well as spectacular views from the large, newer windows. Outdoor living takes center stage here. A wraparound deck - rebuilt for both style and durability - overlooks the wooded grounds and features its own outdoor fireplace, made for slow evenings and weekend entertaining alike. A stone patio off the kitchen adds another spot to gather, while the partially fenced yard offers room to roam. Practical upgrades round out the package: central air conditioning, a second-floor laundry, a radon mitigation system, a UV water filtration system, and a generator

26 Hulda Hill Rd, Wilton
$899,000
3 Beds ⋅ 3 Baths ⋅ 24181353 MLS
Step into the timeless charm of Rock House Woods, an enchanting 1800s farmhouse seamlessly blending historic character with modern conveniences, including GEOTHERMAL heating & cooling! A welcoming front porch invites you into this sun-drenched home, where wide-plank floors, exposed beams, large picture windows and a charming country kitchen creates an atmosphere of warmth, character and sophistication.The spacious family room, adorned with French doors, opens to a lovely flagstone patio-perfect for effortless indoor/outdoor entertaining. The newer primary suite impresses with vaulted ceilings, a grand Palladian window, and a luxurious en-suite bath. Two additional bedrooms and a full hall bathroom complete the second floor. The versatile third-floor space is ideal for a home office, playroom, or 4th bedroom. For equestrian enthusiasts, this picturesque Horse Property features a well-appointed barn with tack room, an additional three-stall stable, and two paddocks, offering the flexibility to convert the property into a traditional lawn or even a potential pool site. Tucked away in a serene country setting, yet just minutes from shopping, dining, top-rated schools, and train access. This private countryside oasis with new geothermal system and new well pump blends old world charm with today's conveniences. The possibilities here are endless!

175 Mountain Rd, Wilton
$1,900,000
5 Beds ⋅ 6 Baths ⋅ 24181977 MLS
Set on a private, serene two-acre lot surrounded by mature trees and lush landscaping, this spacious home offers a rare combination of comfortable living, flexibility, and additional income potential. Just steps from the main residence, a detached, self-contained legal cottage features one bedroom, one full bath, a kitchen, and a private deck-ideal for guests, extended family, a home office, or rental income. The main home features formal living and dining rooms, a family room, breakfast area, study, mudroom, powder room, and a guest bedroom with an en-suite bath and French doors opening to the rear deck. The well-appointed kitchen includes two sinks, two dishwashers, two ovens, a warming drawer, ice maker, wine refrigerator, and an additional refrigerator in the walk-in pantry. Upstairs, the primary suite offers two walk-in closets, a full en-suite bath, and doors opening to a private balcony with beautiful backyard views. A separate study, two additional bedrooms, and two full baths complete the second floor. The lower level provides a versatile bonus room. Additional highlights include an expansive deck, new roof, updated mechanicals, three-car garage, whole-house generator, and built-in speakers. Just steps from the Norwalk River Valley Trail and five minutes to town, train, and commuter routes.

39 Powder Horn Hill Rd, Wilton
$1,799,000
5 Beds ⋅ 4 Baths ⋅ 24170083 MLS
Exceptional contemporary residence set on 2 beautifully landscaped acres of park-like property in one of Wilton's most desirable neighborhoods. Offering 4,347 square feet of thoughtfully designed living space, this impressive 5-bedroom home features 3 full baths and 1 half bath, combining timeless elegance with modern comfort. Newly refinished hardwood floors flow throughout the home, while soaring 9+ foot ceilings enhance the spacious formal living and dining rooms, creating an ideal setting for entertaining. The sun-filled living room showcases a charming fireplace, complemented by a second fireplace in the inviting family room, providing warmth and character throughout the seasons. The well-designed floor plan offers generous living spaces, comfortable bedrooms, and flexibility for today's lifestyle needs. Step outside to your private backyard retreat where beautifully maintained grounds surround an in-ground pool, offering the perfect setting for summer enjoyment, outdoor gatherings, or peaceful relaxation. Mature landscaping and expansive lawns create a tranquil atmosphere with exceptional privacy. Ideally located just minutes from Wilton Town Center, top-rated schools, train service, shopping, dining, and major commuting routes, this home offers the perfect balance of convenience and serenity. A rare opportunity to own a spacious contemporary home on a spectacular property in a sought-after Wilton location. Full house generator!

293 Sturges Ridge Rd, Wilton
$795,000
4 Beds ⋅ 3 Baths ⋅ 24177784 MLS
Tucked away on a private, serene wooded setting in sought-after South Wilton, this beautifully updated home offers the perfect blend of tranquility and convenience. Enjoy the peaceful sounds of a babbling brook while being just minutes to the train to NYC, major highways, top-rated schools, Wilton Center shopping, and dining. Set on just shy of an acre, the home features a brand-new renovated kitchen, updated bathrooms, hardwood floors, new stainless steel appliances, a spacious primary suite with walk-in closet, and a huge two-car garage. A rare opportunity to enjoy blissful privacy surrounded by nature without sacrificing commuter convenience. Location, location, location.

30 Bittersweet Trl, Wilton
$4,975,000
5 Beds ⋅ 5 Baths ⋅ 24174834 MLS
A rare offering distinguished by architectural clarity, complete privacy, and a deeply personal design vision, set within one of Fairfield County's most sought-after locations. Jay Manuel, internationally recognized creative director and fashion icon, brings a distinctly refined point of view to his architecturally significant modern residence in Connecticut. Acquired in 2011, the home was thoughtfully completed and refined under his direction into a highly considered lifestyle environment, where design, performance, and atmosphere exist in complete alignment. Set on 2.75 acres of exceptional privacy, the sunlit European modern unfolds as a discreet compound, surrounded by mature landscape and a protected nature preserve. Designed for both intimate living and large-scale entertaining, the property features a heated saltwater pool and spa, multiple terraces, an outdoor kitchen, fire pit, and a tranquil Zen garden. The residence reflects a disciplined approach to modern living, integrating passive solar principles, advanced HVAC, and whole-property connectivity, all seamlessly embedded within its clean architectural language. Interiors are defined by soaring ceilings, walls of glass, and a Poliform kitchen with Miele appliances. A private primary suite with balcony, a dramatic glass mosaic wine cellar, and a separate 800 sf skylit studio for fitness or flexible use further articulates the home's sense of intention and versatility. Rare. Private. Architectural.

300 Sturges Ridge Rd, Wilton
$1,999,999
6 Beds ⋅ 5 Baths ⋅ 24168304 MLS
Experience the character of the historic Northup-Scott House (c.1760), thoughtfully updated for today's lifestyle and set on four scenic acres. This well-maintained home offers a flexible floor plan with formal living and dining rooms, a spacious keeping room with original fireplace, a sun-filled family room with dramatic architectural window, private office, and first-floor guest suite. The renovated kitchen features a La Cornue range, 48 inch Pro Sub-Zero refrigerator/freezer, Wolfe double ovens, updated countertops, and opens seamlessly to the main living spaces. The second floor includes the primary suite, four additional bedrooms, three updated baths, and laundry room. A unique loft overlooks the impressive barn/great room, offering exceptional space for recreation, studio, gym, or entertaining. The owners put in $1M+ of improvements including newer roof, 75 thermopane windows, refinished hardwood floors, updated mechanicals, installed central air, interior and exterior painting, and renovated full bathrooms. Also purchased lot on Ridgefield border for $299K to allow seemless flow thru circular driveway. Outdoor amenities include pond, tennis court, expansive yard, gazebo and beautiful porch spaces ideal for relaxing or entertaining. A legal rental apartment provides added flexibility for guests, extended family, or supplemental income. A true Wilton gem.

1090 Ridgefield Rd, Wilton
$999,000
3 Beds ⋅ 3 Baths ⋅ 24169226 MLS
This iconic mid-century modern home offers a rare blend of architectural character and natural beauty, situated on two private acres along Olmstead Hill-one of Wilton's designated scenic roads. Designed in 1958 by architect Robert Van Summern (whose work has been featured in The New York Times) as his first family residence, the home thoughtfully integrates timeless design with its serene, wooded surroundings to create a distinctive treehouse-like feel. Original architectural elements remain beautifully intact, including a striking floor-to-ceiling stone fireplace and a dramatic wall of glass that fills the home with natural light throughout the day. The main level features an open layout that seamlessly connects the dining and living areas to a remodeled kitchen featuring custom cabinetry with seeded glass accents, a 9-foot quartz center island, and a dedicated prep sink. A brand-new powder room and freshly painted interiors add a crisp, updated feel, while the vaulted three-season porch and multiple sliding glass doors extend the living space onto the wraparound deck and wooded grounds. Upstairs, the primary suite offers cathedral ceilings, a private balcony overlooking the wooded grounds, and an oversized walk-in closet and dressing area. The en-suite bath showcases striking artisan glass vessel sinks that complement the home's mid-century modern aesthetic. The upper landing features floor-to-ceiling built-in bookcases and a cascading glass chandelier.

305 Olmstead Hill Rd, Wilton
$1,850,000
4 Beds ⋅ 5 Baths ⋅ 24167372 MLS
Located in prime South Wilton just minutes from Westport and New Canaan, this exceptional colonial blends timeless New England charm with today's most sought-after amenities. Thoughtfully upgraded, this home offers 4 spacious bedrooms, 5 well appointed bathrooms, abundance of living space, & a layout ideal for everyday living & entertaining. At the heart of the home is a fully updated kitchen w/ stainless steel appliances, dining area, & direct access to the deck, perfect for indoor-outdoor living. Just off the kitchen, the family room is centered around a wood-burning fireplace & French doors that open to the deck & overlook the private backyard. The main lvl also includes a formal dining room & spacious living room w/ wood-burning fireplace. Upstairs, the luxurious primary bedroom suite serves as a private retreat w/ fireplace, spa-like bathroom & walk-in closet. Each additional bedroom is well-proportioned w/ access to beautifully appointed full baths, offering comfort & privacy, while a large rec/media room offers flexibility for work or play. The lower lvl offers a range of possibilities, w/ plenty of room for an office, gym, or media room. Outside, the expansive deck and backyard provide the perfect setting for entertaining or relaxing. Perfectly located just minutes from top-rated schools, town amenities, and commuter routes, this home offers an exceptional balance of luxury, functionality & convenience.

6 Admiral Ln, Wilton
$2,679,000
6 Beds ⋅ 7 Baths ⋅ 24165364 MLS
20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 7200 sqft, with an additional 2100+ sqft lower level, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double marble islands, double ovens, dual dishwashers, navy subway tile, and a custom coffee/wine bar, flowing into the oversized Great Room with a massive stone fireplace, full bar, and direct access to the resort style pool area. The flexible layout includes 6 bedrooms, a luxurious primary suite with private balcony and oversized walk-in closets, double office/conference spaces, library, homework zone, first floor guest suite, and a fully self contained in-law/au pair suite with private entrance, kitchen, and living area. The renovated lower level offers a gym space, wine cellar, oversized playroom with custom bunk beds. Outdoors enjoy a restored pool and spa, sports courts, playground, gazebo, fire pits, and multiple entertaining areas. Major upgrades include a new 2024 roof, updated HVAC, plumbing, electrical, and a renovated 4 car garage with smart-tech doors. Move in ready, this exceptional estate offers incredible space, infrastructure, and upside in a premier school district.

20 Cherry Ln, Wilton
$3,495,000
5 Beds ⋅ 8 Baths ⋅ 24148986 MLS
Handsomely set on two private, resort-like acres, this timeless Nantucket-style residence offers the feel of a secluded family compound. Adjacent to a 21-acre wildlife preserve along the west bank of the Saugatuck River, the setting invites fishing by the river and peaceful walks along scenic trails through the surrounding natural landscape. Custom built by celebrated architect Tim Geitz, the home blends classic design with modern comfort across four levels, all served by elevator. The open floor plan is filled with natural light and thoughtfully designed spaces, including a striking two-story glass-walled home office with fireplace and a beautifully appointed library. A chef's kitchen with breakfast room flows to a spacious four-season sunroom and out to terraces, outdoor kitchen, pool and spa; ideal for effortless indoor-outdoor living and entertaining. The serene primary suite features a private balcony overlooking the tranquil grounds and a luxurious spa bath with heated floors and jacuzzi. Additional amenities include a third-level media room, state-of-the-art fitness studio and walk-out lower level with billiards, bar and an impressive 500-bottle wine cellar. Whole-house generator. A private retreat that feels miles away, yet minutes to the centers of Westport, Weston and Wilton.

253 Rivergate Dr, Wilton
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 24138959 MLS
Welcome to the historic James Benedict House, one of Wilton's most notable and beautifully preserved 18th-century residences. This thoughtfully updated antique Colonial seamlessly blends timeless craftsmanship with modern convenience, offering 2,803 square feet across three full levels-including a true third floor with tall ceilings (not an attic)-plus a walk-out lower level ready to be finished. Set on an exceptional 4.81-acre property with a private pond, this rare offering provides unmatched privacy, scenic beauty, and the opportunity to create your own walking trails-all within one of South Wilton's most desirable locations. Property Highlights 4 Bedrooms | 2 Full Baths | 1 Half Bath 10 total rooms across three full levels True third floor with full ceiling height Walk-out lower level with finishing potential Central chimney with 5 fireplaces (3 gas, 2 wood-burning) Classic post-and-beam construction Refinished wide-plank hardwood floors Two staircases to the upper level Spacious eat-in kitchen Recent Upgrades & Enhancements Fully painted interior and exterior Updated bathrooms with modern finishes LED lighting throughout Brushed gold fixtures, hardware, and accents New backsplash Upgraded Decora-style switches and outlets (many with dimmers)

332 Belden Hill Rd, Wilton
$2,995,000
5 Beds ⋅ 7 Baths ⋅ 24047255 MLS
This proven luxury home builder wants to build your future dream home on this rarely available one of a kind private lot. Drive down a private, hidden 1000+ foot driveway to find a property totaling over 2.00+ acres of unmatched and untouched exclusivity surrounded by protected state land. Add pool and tennis too! Two amazing potential lot sites. In addition, and even a possibility of subdividing. Here is your chance to choose your style and finishes on this custom home. Also, this property can be purchased with all site work, utilities, septic & well for $900,000 or as is for $750,000.

Mountain Rd, Wilton

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