Refine Search
Sort by
$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

$899,500
4 Beds 3 Baths 24175372 MLS
Nestled on a gorgeous, prime piece of property in one of Wilton's most sought-after locations, this 4 bedroom, 3 full bath ranch offers an exceptional opportunity to create your dream home. Set within one of Connecticut's top-rated school districts and a highly desirable commuter location, this property combines convenience, charm, and endless potential. The home features an easy one-level ranch-style layout with great flow, large sun-filled windows, and bright natural light throughout. A welcoming living space showcases built-in bookshelves surrounding the fireplace, adding warmth and character to the home. The dining room is ideally situated just off the spacious kitchen, creating a wonderful flow for both everyday living and entertaining. Featuring cathedral ceilings and an abundance of natural light, the space feels open, airy, and inviting. The large kitchen offers excellent storage, a center island, and tremendous potential to design the kitchen of your dreams while taking full advantage of the home's functional layout and bright, welcoming atmosphere. The main level of the home offers the ease and convenience of a spacious primary suite complete with a full ensuite bathroom and laundry. Two additional bedrooms with hardwood flooring and another full bathroom complete the main level.

74 Hurlbutt St, 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

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.