South Wilton Homes for Sale

Welcome to South Wilton, a charming enclave nestled in the heart of Wilton, Connecticut, within the picturesque Fairfield County. This delightful neighborhood seamlessly blends suburban tranquility with a vibrant community spirit, making it an ideal place for families, professionals, and retirees alike. Known for its lush landscapes, tree-lined streets, and friendly neighbors, South Wilton offers a serene escape while still being conveniently close to urban amenities.

One of the standout features of South Wilton is its excellent school system, which is consistently rated among the best in the state. Families will appreciate the top-notch educational opportunities available, fostering a strong sense of community and support. The area is also home to numerous parks and recreational facilities, providing ample opportunities for outdoor activities, from hiking and biking to picnicking and sports.

For those considering a move, South Wilton boasts an impressive selection of homes for sale. Whether you’re looking for a charming colonial, a modern farmhouse, or a spacious contemporary, there’s something to suit every taste and lifestyle. Many of these homes feature generous yards, perfect for entertaining or enjoying a quiet evening under the stars.

With its combination of natural beauty, community-oriented living, and a diverse housing market, South Wilton is more than just a place to live; it’s a place to call home. Explore the available listings today and discover the perfect property to start your next chapter in this enchanting neighborhood!

Newest South Wilton Homes for Sale

$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

$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

$999,000

4 Beds ⋅ 3 Baths ⋅ 24188546 MLS

BEST AND FINAL 7/21 3:00PM. Welcome to #1 Wilton Acres, a masterfully reimagined South Wilton haven, where a classic style meets a breathtaking modern evolution. Step inside and immediately feel the light filled, open concept design.Transformed from the bottom up, this 4 Bedroom RR blends sleek sophistication with the warmth of a true forever home. Every upgrade has been thoughtfully redesigned - new, spacious sanctuary that is the Primary En suite addition. New 3rd garage bay for the car enthusiast. City Water. NEW Propane heat system. All bathrooms updated. NEW HVAC/Central Air. All redesigned with luxury finishes to elevate your daily living, offering a perfect sanctuary for a modern lifestyle. The fluid, open layout invites flexibility whether hosting dinner parties or enjoying quiet weekend mornings on your private, maintenance free Trex deck. This home offers turn key peace of mind with completely fenced in property, creating a secure private paradise where kids and pets can roam freely while keeping deer and other wildlife out to protect your professional landscaping. Main Level offers a formal LR with hardwood, formal Dining Space and beautiful EIK with SS appliances and granite counters. 3 Beds and 2 full Baths. Lower Level is finished with 4th Bedroom, Family Room with fireplace with sliders to under porch covered patio. Laundry Room and 1/2 Bath plus plenty of storage closets with direct access from 3 car garage. Just unpack to enjoy Award Winning schools and more!

1 Wilton Acres, 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

$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

$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

$1,850,000

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

Start Your Search

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.