South Wilton Real Estate

Welcome to South Wilton, a hidden gem nestled in the heart of Wilton, Connecticut. This charming neighborhood is known for its picturesque landscapes, vibrant community spirit, and a perfect blend of suburban tranquility and urban convenience. With its tree-lined streets and beautifully maintained homes, South Wilton offers a serene escape while being just a stone's throw away from the bustling amenities of Fairfield County.

One of the standout features of South Wilton is its commitment to preserving nature. Residents enjoy easy access to numerous parks and nature reserves, making it an ideal spot for outdoor enthusiasts. Whether it’s hiking along the scenic trails of the nearby Wilton Town Forest or enjoying a picnic at the picturesque Merwin Meadows Park, there’s no shortage of ways to embrace the great outdoors.

Families are drawn to South Wilton for its top-rated schools, which are known for their academic excellence and strong community involvement. The neighborhood fosters a close-knit environment, where neighbors become friends and children play freely in the safe, welcoming streets.

With its proximity to downtown Wilton, residents can enjoy a variety of local shops, restaurants, and cultural attractions. The Wilton Historical Society and the popular Wilton Library are just a short drive away, offering an array of activities for all ages.

In South Wilton, you’ll find more than just a place to live; you’ll discover a vibrant community that values connection, nature, and a high quality of life. Come explore this enchanting neighborhood and see why so many people are proud to call South Wilton home!

Newest Listings in South Wilton

$759,000

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. Move right in and enjoy turnkey, low-maintenance condo living!

8 Glen Rdg Unit 8, 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

$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

$725,000

2 Beds ⋅ 3 Baths ⋅ 24190757 MLS ⋅ Wilton Crest BLDG.

Wilton Crest - 2 bedroom, 2 full and 1 half bath townhome 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

$670,000

2 Beds ⋅ 2 Baths ⋅ 24189672 MLS ⋅ Fawn Ridge BLDG.

Completely renovated and move in ready, this exceptional three level townhouse in the sought after Fawn Ridge community offers 2 bedrooms, 2 full bathrooms, a one car garage, and a versatile loft. Thoughtfully redesigned with high end finishes, this home combines style, comfort, and functionality. The stunning new kitchen features custom cabinetry, granite countertops, a designer backsplash, and new stainless steel appliances, including a range, dishwasher, and hood. The open concept living and dining area showcases hardwood floors, recessed lighting throughout, custom built ins, and a cozy wood burning fireplace. A new sliding glass door leads to a freshly painted private balcony, perfect for relaxing or entertaining. Both bathrooms have been beautifully renovated. Radiant heated floors in the entry, office, and primary bathroom add everyday comfort. Additional upgrades include upgraded windows, elegant wood staircases, a Nest smart home system, Ring security camera, new garage door, fresh interior paint, and updated lighting throughout. Enjoy resort style amenities including a pool and tennis court, just minutes from Wilton Center, award winning schools, shopping, dining, Metro-North, and major commuting routes. Immediate occupancy available. Move right in and enjoy maintenance free living at its finest.

4 Fawn Ridge Ln Unit 4, Wilton

$649,000

2 Beds ⋅ 2 Baths ⋅ 24189066 MLS ⋅ Fawn Ridge BLDG.

Rare opportunity to own a unit in the desirable Fawn Ridge complex on Wilton school system side, conveniently located to highways and shopping! This end-unit townhome offers 2 bedrooms, 2 bathrooms, gorgeous eat-in kitchen with granite countertops, and slider to spacious deck for outdoor dining. Large living room with wood burning fireplace with a window bay perfect for reading a book. Upstairs are two large bedrooms and a large bathroom with whirlpool tub and walk-in closet. Bonus finished room in basement can be an office, gym, play or rec room. Garage is deep and offers space for storage as well as a standard SUV. Hardwood throughout the townhome, sun-lit windows, beautiful paint choices, low HOA fee, nothing to do but move in and enjoy the pool, tennis courts and everything South Wilton offers!

61 Fawn Ridge Ln Unit 61, 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

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