Refine Search
Sort by
$3,125,000
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

$2,395,000
5 Beds 7 Baths 24206451 MLS
Sophisticated South Wilton Colonial: This Nantucket shingle-style residence blends timeless architectural elegance with seamless modern luxury, ideally positioned for effortless commuting to town, the train, and the Merritt Parkway. Thoughtfully designed for both grand entertaining and everyday comfort, the home features gorgeous custom details, extensive high-end upgrades, and an integrated three-zone surround sound system. The chef's kitchen is outfitted with premium appliances including a Viking six-burner gas cooktop, double ovens with a warming drawer, a built-in refrigerator, and a Miele dishwasher, opening directly into an inviting family room with custom built-ins and fireplace. On the main level, a sophisticated room provides versatile living space, seamlessly accommodating a formal dining room or private work space. Upstairs, the master bedroom serves as a luxurious private sanctuary with a cozy fireplace, a dedicated sitting area, expansive walk-in closets, and a spa-inspired primary bath. There are four additional bedrooms on this floor, two with ensuite bathrooms and two with a connected full-bath. The upper third level boasts a sixth bedroom suite and a large multi-generational living space with extensive built-ins, including cozy window-seating. The finished lower level provides an ideal versatile space featuring a spacious dedicated play/ game room, home gym, and a comfortable TV-watching area designed to grow right along with your kids...

249 Chestnut Hill Rd, Wilton

$2,395,000
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

$2,349,000
5 Beds 7 Baths 24199612 MLS
Move right into one of South Wilton's most desirable areas. Set on 2.2 beautifully landscaped acres, this exceptional, elegant blend of timeless architecture, refined interiors, and extraordinary outdoor living was built by Tomas Brothers. Professionally designed and fully irrigated gardens create a private, resort-like setting surrounding the home, with mature plantings and thoughtfully curated spaces that are as beautiful as they are inviting. Inside, gracious proportions and sophisticated details define the home, with five bedrooms, three en-suite baths, and a Jack-and-Jill bath providing exceptional comfort and flexibility. Five fireplaces create warmth and character throughout, including the luxurious primary suite, family room, private office, living room, and finished lower level. The heart of the home is for grand entertaining and comfortable everyday living, with beautifully appointed gathering spaces that flow effortlessly from one room to the next. The upper-level has a media room, and a sitting room attached to the primary bedroom serves as a nursery or studio. The finished lower level extends the living space, features its own fireplace and full bath, and is a potential in-law suite. A truly distinctive wine cellar, adorned with a hand-painted evocative mural inspired by Tuscany, provides an elegant setting for wine enthusiasts. Only 4 miles to the New Canaan train station for a fast commute to NYC. Close to major highways, shopping & restaurants.

77 Old Boston 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

$1,295,000
4 Beds 3 Baths 24207252 MLS
Easy living and convenient commuting converge at 12 Crowne Pond Lane, a beautifully updated and meticulously maintained home. Tucked away in an exclusive enclave of just three homes, this 4 bedroom, 3 bath single-family sanctuary combines true privacy with the benefits of a maintenance-free planned community. The main level offers a fluid, open-concept floor plan designed for effortless entertaining. At its heart is a bright white kitchen featuring granite countertops and stainless steel appliances, seamlessly connecting to the family room with a cozy wood-burning fireplace and sliders opening to an expanse of back deck. Upstairs, the spacious primary suite serves as a quiet retreat, complete with a generous walk-in closet and a spa-inspired bath highlighted by marble surfaces, double sinks, a soaking tub, and a custom marble waterfall tile shower. Three additional bedrooms, a second full bath, and dedicated upper-level laundry complete the space, while a finished lower level provides flexible room for a gym, office, or media center. Complete with city utilities, a private lawn, and close proximity to Wilton Center, top schools, and train station, this home offers the ultimate suburban lifestyle.

12 Crowne Pond Ln Unit 12, Wilton

$1,065,000
4 Beds 3 Baths 24138959 MLS
Set on an exceptional 4.81-acre property. 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. Potential to add an ADU Accesory Dweling Unit, Barn/garage for horse lovers, hiking trails ertc. 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

$1,049,000
4 Beds 3 Baths 24201924 MLS
A little more space. A little more privacy. And everything else still close. Tucked away on 3+ acres in Wilton's Silvermine area, this home offers the breathing room people come to Wilton for, with everyday conveniences surprisingly close by. A long driveway winds through the wooded acreage before the property opens to a level lawn framed by mature trees. Inside, there's an easy comfort to the way this home lives. The eat-in kitchen opens to a cozy fireside sitting room with access to the patio-a natural spot for morning coffee, homework, or unwinding at the end of the day. A spacious family room offers another place to gather, while the separate dining room is ready for holidays, dinner parties, and everything in between. Upstairs, four comfortable bedrooms create a natural separation from the main living spaces, including a primary suite with a private bath. The finished lower level adds even more flexibility for movie nights, play space, a home gym, or whatever life calls for next. Move-in ready with room to make it your own, this is a home that can evolve right along with you, with the added benefit of public water, a welcome rarity in Wilton. And perhaps the biggest surprise is just how connected you are-minutes to Wilton Center, schools, the train, New Canaan, and the Merritt Parkway. Maybe Wilton is closer than you think.

98 Old Boston Rd, Wilton

$979,000
4 Beds 3 Baths 24203986 MLS
Welcome to this beautiful turn-key Colonial with serene views and ultimate privacy at the end of a cul-de-sac. Located in highly desirable Lower Wilton just minutes from local shops, top-tier restaurants, and everyday amenities, with the bustling town centers of Westport, Wilton and Norwalk. With easy access to Metro-North train stations for commuting to New York. This home offers the ultimate blend of tranquility and unmatched convenience. The inviting floor plan includes a spacious living room, dining room perfect for holiday gatherings, and a cozy family room anchored by a warm fireplace-with direct access to the spacious deck for effortless entertaining. The heart of the home is an updated eat-in kitchen with granite counters, stainless appliances, and versatile cabinet storage. Upstairs are four spacious bedrooms and tastefully updated bathrooms, including a private front to back primary suite. Looking for more space? The finished walk-out lower level serves as the perfect bonus room, home office, gym, or guest suite. Potential first floor or lower level apartment with separate entrance offers versatility. Complete with a full-service automatic whole house generator (Briggs & Stratton) for your peace of mind. The home is fully equipped with the Google Smart Home ecosystem which services the interior home lights, climate controlled thermostat and security system. Don't miss the video tour link!

20 Overidge Ln, Wilton

$949,000
4 Beds 3 Baths 24205676 MLS
Welcome to 51 Stonebridge Road, a charming four-bedroom, 2.5-bath home set on 1.52 beautiful acres in a peaceful South Wilton setting. Lovingly cared for by the same family for more than five decades, this special property is tucked away on a quiet cul-de-sac abutting Aspetuck Land Trust protected open space, offering exceptional privacy. Inside, hardwood floors, abundant natural light and a fireplace add warmth and character. A French door from the living room opens to a spacious patio and level backyard, while the dining room leads to a deck and additional patio, perfect for morning coffee. The sun-filled kitchen features a skylight, ample cabinetry and granite-topped island. A heated, finished walk-out lower level with half bath and separate entrance offers flexible living space, while the bonus room above the garage is ideal for a home office. A whole-house generator and new furnace installed in 2025 add peace of mind. Minutes to Wilton Town Center and Metro-North, approximately 2.5 miles to the Merritt Parkway, with convenient access to Westport's train station, shopping and dining. A rare opportunity to enjoy the privacy, natural beauty and timeless Wilton charm of this special property.

51 Stonebridge 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

$725,000
2 Beds 3 Baths 24193554 MLS Glen River BLDG.
This beautiful, light-filled townhome is located in Glen River, one of Wilton's most sought-after communities. Offering the perfect blend of style, comfort, and convenience, the home features updated kitchen and baths, fresh hardwood floors, and thoughtful details throughout. The updated kitchen boasts modern finishes and stainless steel appliances, creating a clean, functional space for everyday living and entertaining. Adjacent open-concept living and dining areas are bathed in natural light, highlighted by beautiful custom millwork and a cozy wood-burning fireplace. Need a quiet place to work or relax? The cozy office/den features custom built-ins and a sunlit skylight. Wide sliding glass doors open to a private patio-ideal for morning coffee, alfresco dining, or unwinding at the end of the day. Upstairs, the spacious primary suite includes a walk-in closet with a custom California Closet system and a beautifully updated full bath. The second bedroom features a dramatic vaulted ceiling, a palladium window, and its own walk-in closet. A full-sized second-level laundry adds true everyday convenience. A 1-car carport and plenty of guest parking are a great addition to this home. Residents of Glen River enjoy a private in-ground pool and an unbeatable Wilton location-just minutes to the town center, Metro-North train, local shopping, dining, and scenic walking trails. Enjoy turnkey, low-maintenance condo living!

8 Glen Rdg Unit 8, Wilton

$698,000
2 Beds 3 Baths 24190757 MLS Wilton Crest BLDG.
Light and bright town home at Wilton Crest, in the heart of Wilton. Quick close possible. 2 bedroom, 2 full and 1 half bath home with the living room, dining room, kitchen, primary bedroom, primary bathroom, laundry, half bath, and two decks all on one level. The second bedroom and full bathroom are on the second floor, and a full unfinished basement is on the lower floor. The unit is just a short walk from your garage, and just six steps up from the walkway brings you into the front door. Vaulted ceilings, skylights, sliders to the decks provide a light, bright and open feel to this home. Just freshly painted throughout. New hardwood floors in the primary bedroom, and refinished hardwood floors in the living room and dining room. Granite counters and stainless steel appliances in the kitchen. Vaulted ceiling, ceiling fan and a wood burning Fireplace in the living room. Central Air conditioning, hot water heater new in 2023. Wilton Crest amenities include a nice size Swimming pool just a short walk from #50. Convenient South Wilton location, close to Wilton center, one mile +/- to Wilton Library, the Supermarket, restaurants and stores, sidewalk from Wilton Crest takes you into the center. Less than 2 miles to Wilton Train Station. Move in and enjoy...

50 Wilton Crest Unit 50, Wilton

$660,000
2 Beds 3 Baths 24192946 MLS Glen River BLDG.
Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse in the heart of downtown Wilton, offering the perfect blend of comfort, style, and convenience. Filled with natural light, the main level features hardwood floors throughout and a welcoming foyer with French doors leading to a spacious living room with custom built-ins, a fireplace, and sliding doors to the newly refinished private patio. The updated kitchen features granite countertops, stainless steel appliances, and a built-in wine chiller, flowing seamlessly into the dining area and remaining open to the living room for effortless everyday living and entertaining. A convenient half bath completes the main level. Upstairs, the spacious primary suite features vaulted ceilings, a renovated bath, and a walk-in closet. A second bedroom, full bath, upper-level laundry, and a versatile flex room ideal for a home office, den, guest space, or playroom complete the second floor. An additional bonus area off the staircase offers the perfect spot for a home gym, reading nook, or extra storage. Newer windows, sliders, and an updated HVAC system provide efficiency and peace of mind for years to come. Enjoy the convenience of a dedicated carport, ample guest parking, and a desirable community with a pool, all just a short stroll to Wilton Center's restaurants, shops, library, train station, and everything the village has to offer. Click on Movie Icon for Virtual Tour

13 Glen Ridge, Unit 13, Wilton

$600,000
2 Beds 2 Baths 24207874 MLS Fawn Ridge BLDG.
Ideally situated on the Norwalk/Wilton line, this beautifully maintained condominium offers privacy, comfort, and an unbeatable commuter location. Set toward the back of the complex, the unit enjoys a peaceful, tucked-away feel, with the kitchen window, dining area, and private deck all overlooking natural surroundings rather than passing traffic or neighboring units. Inside, the living room's floor-to-ceiling windows fill the space with natural light, while the multi-level layout creates distinct living zones: a welcoming entry, garage access, and laundry on one level, an open kitchen and living area with a spacious island offering abundant prep space and storage, and bedrooms upstairs for a cozy, private retreat away from the main living areas. The upper level features a double-sinks in the primary bedroom, allowing two people to get ready at once with ease. Generously sized rooms throughout and abundant closet space provide comfortable, flexible living. An attached garage adds everyday convenience. Residents enjoy access to the pool and tennis courts, and the location cannot be beat: close to shops and restaurants, yet quiet within the complex, with easy access to major commuting routes and New York city.

46 Fawn Ridge Ln Unit 46, Wilton

$565,000
1 Beds 2 Baths 24195240 MLS Glen River BLDG.
Welcome to this beautifully updated two-story townhouse in the highly desirable Glen River community, ideally located just moments from the heart of Wilton Village. Enjoy the convenience of walking to shops, restaurants, the library, parks, the Norwalk River Valley Trail, and the Metro-North train. Inside, the open-concept main level features gleaming hardwood floors, a spacious living and dining area, an updated kitchen, and a convenient powder room-ideal for both everyday living and entertaining. Upstairs, the sun-filled primary bedroom boasts a vaulted ceiling and a generous walk-in closet. A versatile second room is perfect as a guest bedroom, home office, or study, while a full hall bath and an oversized hallway closet provide excellent additional storage. Central air conditioning ensures year-round comfort. Residents of Glen River enjoy a community pool, beautifully landscaped grounds, and the convenience of a covered parking space just steps from the unit. Offering a low-maintenance lifestyle in a welcoming community, this move-in-ready home combines comfort, convenience, and an exceptional Wilton location.

9 Glen Rdg Unit 9, Wilton

$539,900
1 Beds 2 Baths 24203303 MLS Glen River BLDG.
YOUR NEXT CHAPER SHOULD START RiGHT HERE IN WILTON! Welcome to Glen River, a premier townhouse community offering an exceptional combination of location, privacy, lifestyle, & value. Aggressively priced, this beautifully maintained 1bed+Den townhouse lives like a 2bed & is ideally positioned in one of the most private settings in the complex, overlooking a peaceful tree-lined backdrop. Walk to everything Wilton Village has to offer, including charming boutiques, restaurants, coffee shops, ice cream, grocery store, library, parks, Metro-North train, & Norwalk River Valley Trail. Inside an open kitchen flows into living/dining room where dramatic floor-to-ceiling stacked stone wood-burning fireplace creates a beautiful focal point. Sliders open to a private patio & bring abundant natural light into the home. Upper-level features spacious primary bedroom w/ vaulted ceilings & large walk-in closet, versatile den, full bath, laundry, and generous storage. The den provides excellent flexibility as a 2nd bedroom, office, guest room, or additional living space. a 1-car garage w/ additional storage adds additional convenience. Enjoy Glen River's beautifully maintained grounds and resort-style in-ground pool w/ lounge chairs, tables, umbrellas and changing area. Located in one of CT's most highly regarded school districts, this is an incredible opportunity to enjoy Wilton living, walkability, and top-rated schools at a very attractive price.

35 Glen Ridge, Unit 35, 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.