South Wilton Homes for Sale

Welcome to South Wilton, a hidden gem nestled in the picturesque town of Wilton, Connecticut, within the scenic Fairfield County. This charming neighborhood offers a perfect blend of suburban tranquility and vibrant community spirit. With its lush greenery, winding roads, and beautifully maintained homes, South Wilton is ideal for families, professionals, and anyone looking to enjoy a serene lifestyle.

The community is renowned for its top-rated schools, making it a sought-after destination for families who prioritize education. Residents can take advantage of the many nearby parks and recreational facilities, including hiking trails, sports fields, and playgrounds, ensuring that there’s always something fun to do outdoors. South Wilton also boasts a strong sense of community, with regular events and gatherings that foster connections among neighbors.

When it comes to real estate, South Wilton is a treasure trove of opportunities. Homes for sale in this neighborhood range from charming colonials to modern estates, catering to various tastes and budgets. Many properties feature spacious yards, updated interiors, and proximity to local amenities, including boutique shops and delightful dining options. Whether you’re a first-time homebuyer or looking to upgrade, South Wilton offers a diverse selection of homes that promise comfort and style.

In South Wilton, you’re not just purchasing a home; you’re investing in a lifestyle. Experience the warmth and charm of this vibrant community, where your dream home awaits! Explore the available listings today and discover why so many are eager to call South Wilton home.

Newest South Wilton Homes for Sale

$6,995

5 Beds ⋅ 4 Baths ⋅ 24208652 MLS

Spacious 5-bedroom Colonial set on 2.16 acres in desirable South Wilton, offering an ideal combination of privacy, space, and convenience. The 3,575 sq. ft. main residence features a first-floor primary suite with vaulted ceiling, skylight, private bath, and generous closet space. The open-concept kitchen, dining, and living areas provide a comfortable flow for everyday living and entertaining, complemented by two fireplaces. A separate den/home office and spacious family room add flexibility to the main level. Upstairs are four additional bedrooms and two full baths. The home also features a finished lower level, enclosed porch, patio, and garage. The property also includes a separate 660 sq. ft. accessory dwelling with 1 bedroom and 1 bath, available to the tenant for an additional cost. An excellent option for those seeking additional living space, a private home office, or flexible accommodations. Please inquire for additional details and pricing. Enjoy a large, level property in an established neighborhood with convenient access to Wilton Center, schools, Metro-North, the Merritt Parkway, shopping, dining, and area trails. A rare opportunity to enjoy exceptional space, privacy, and flexibility in a convenient South Wilton location. Available date is 12/01/2026.

231 Rivergate Dr, 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

$1,625,000

4 Beds ⋅ 3 Baths ⋅ 24207487 MLS

The most magical setting begins on a quiet cul-de-sac in South Wilton. Welcome to 11 Greenbriar Lane, a freshly painted 4-bed Colonial set on 1 acre. The kitchen is a cook's dream, with a Viking gas cooktop, Sub-Zero refrigerator, Miele double wall oven, warming drawer, and dishwasher, plus custom cabinetry and a wine bar. The main level flows through an open concept, eat-in kitchen, fireplaced living room, den and sitting room with beautiful views of the back yard. The home office with built-ins offers tucked away convenience. The newly renovated mudroom is accessible from both the side door and two-car garage. A separate staircase leads to a hidden-away family room above the garage, with beamed ceilings, projector and a second fireplace, perfect for movie nights and lazy weekends. Upstairs are four bedrooms, including the primary suite with walk-in closet and renovated marble bathroom with double vanity and heated floors, plus a second-floor laundry room. Outside, professionally landscaped grounds with a gentle brook, stone walls, and perennial gardens frame flat front and back yards with irrigation. The stone patio, terraces, and outdoor fireplace make it an entertaining paradise. Behind the charm are thoughtful updates: exterior paint (2026), garage EV charger, a generator hookup, and upgraded well and water systems. Just 3 minutes to Wilton Center, with easy access to the Merritt, Route 7, and Metro-North, it's a commuter's dream. Your happily ever after begins here.

11 Greenbriar Ln, 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

$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

$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

$1,185,000

4 Beds ⋅ 3 Baths ⋅ 24204965 MLS

Highest and Best by Monday, September 14 at 3pm. 75 Ledgewood feels like a hidden retreat, set on two private acres bordering protected Wilton land. Surrounded by mature trees and filled with beautiful light, this south-facing, classic Colonial offers a rare sense of privacy while still keeping you close to everything. Inside, thoughtful updates, warm interiors and an easy connection to the outdoors create a home that feels incredibly inviting. The fully updated kitchen opens directly to the deck, while living and dining rooms offer plenty of space to gather. A sun-filled family room with double-sided brick fireplace opens to the patio, and a separate office space with built-ins invites you to work or unwind. Upstairs are four bedrooms and two full baths, including a primary suite with renovated bath featuring heated floors and a walk-in closet. Hardwood floors and abundant natural light carry throughout the home. Outside, the deck, bluestone patio and expansive yard create multiple spaces to dine, entertain or simply enjoy the private, natural surroundings. Meticulously maintained, 75 Ledgewood combines the privacy of a tucked-away setting with the convenience of desirable South Wilton - minutes to town, top-rated schools and commuter routes to NYC.

75 Ledgewood Dr, 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

$979,000

3 Beds ⋅ 3 Baths ⋅ 24191982 MLS

Nestled among the trees in desirable South Wilton, this architecturally significant mid-century modern contemporary offers timeless design, privacy, and comfort. Inspired by Frank Lloyd Wright's School of Design at Taleisin. Offering approximately 2,700 square feet, this 3-bedroom, 2.5-bath residence is filled with natural light from expansive windows and sliding glass doors that seamlessly connect the interior with the surrounding landscape. A dramatic living room features vaulted ceilings, exposed wood beams, built-in shelving, and a striking stone fireplace. The adjoining dining room flows into the kitchen and inviting family room with a wood-burning fireplace and sliders to the deck and private backyard. The spacious primary suite is a true retreat with its own fireplace, sitting area, walk-in closet, private deck access, and spa-inspired bath with soaking tub, oversized shower, double vanity, skylight, and water closet. Two additional bedrooms, hardwood floors, an attached two-car garage, and a full unfinished basement provide flexibility and abundant storage. Conveniently located just minutes to Metro-North, major commuting routes, Wilton Center, and award-winning schools, this is a rare opportunity to own an architecturally distinctive home in one of Fairfield Counties favorite towns.

512 Belden 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

$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

$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

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