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

$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 principles of organic architecture, the home was designed by noted Connecticut architect David D. Coffin, with original plans by Rafter Johnson, Inc. 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

$2,695,000

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

$799,000

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

$2,099,999

5 Beds ⋅ 7 Baths ⋅ 24187095 MLS

Completely reimagined in 2022, this stunning center hall colonial offers the rare combination of timeless architecture and newer everything - making it the turnkey opportunity buyers in Wilton have been waiting for. Set on a level two-acre parcel, this 5-bedroom, 6 1/2-bath home features a fully redesigned kitchen, 2022 installed HVAC/AC, roof, hot water heater, and water softener. Soaring vaulted ceilings, a dramatic floor-to-ceiling stone fireplace, and a spa-inspired primary suite with oversized soaking tub set the tone throughout. The finished lower level adds a home gym, recreation room, and full bath. Hardwood floors, 3-car garage, circular drive, and a stunning stone-walled backyard complete this exceptional property. Walk to the Norwalk River Valley Trail and Ambler Farm; minutes to top-rated schools and Wilton/Cannondale train station. Move-in ready - everything's already been done.

125 Skunk Ln, Wilton

$878,000

4 Beds ⋅ 3 Baths ⋅ 24182432 MLS

Please submit highest & best offers by 6 PM on 6/25/26, thank you. Absolutely Charming! This light-filled home offers three spacious living levels and a warm, inviting layout throughout. Enter into a welcoming living room with a fireplace-perfect for relaxing or entertaining. The first floor also features a private office or optional fourth bedroom, along with one of three full baths. The main level is ideal for both everyday living and gatherings, featuring a large dining room with direct access to the sunroom and kitchen with an eat in area. Just off the dining room is an oversized, well-proportioned living room. Upstairs, you will find three additional bedrooms along with the third full bath. All three full baths in the home have been renovated with highest quality craftmanship. The above-grade lower level offers a fun and flexible space to unwind, complete with a wet bar and direct access to the two-car garage & laundry. Generous storage can be found throughout the home. Enjoy outdoor living on the deck-ideal for dining or relaxing-overlooking 2.6 acres of beautiful property, ready for you to personalize with endless possibilities. Set on a quiet road, close to town, schools, and the Wilton YMCA. An incredible value with wonderful potential Please note: The town shows 2 full & 1 half bath, however this home has 3 full bathrooms.

34 Powder Horn 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

$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

$2,679,000

6 Beds ⋅ 7 Baths ⋅ 24165364 MLS

Move right in! This gorgeous Georgian Colonial private home is set on nearly 2.5 of flat, landscaped acres. Boarding 50 acres of protected conservation land, you will feel the privacy and serenity of this grand entrance the moment you drive up. Offering over 7200 sqft, and 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

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