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

$1,185,000

4 Beds ⋅ 3 Baths ⋅ 24204965 MLS

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

$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

$1,310,000

3 Beds ⋅ 4 Baths ⋅ 24201638 MLS ⋅ Wilton Hills BLDG.

SELLER IS REQUESTING ALL OFFERS TO BE SUBMITTED BY TUESDAY, SEPT. 1ST BY 5:00pm. Located in highly desirable Wilton Hills, this stunning home has been completely transformed over the past six years, offering modern luxury, thoughtful updates, and an exceptional open-concept floor plan. A dramatic two-story foyer welcomes you into a light-filled interior featuring a spacious great room with cathedral ceilings, new mouldings, a new gas fireplace, and a wall of windows overlooking the beautiful and private surroundings. The completely renovated chef's kitchen is a true showstopper, featuring gorgeous quartz countertops, custom cabinetry, a generous 9-foot island, and top-of-the-line Wolf, Bosch, and Sub-Zero appliances. The main-level primary suite provides a private retreat with expansive windows, walk-in closet, tray ceiling and a beautifully updated bath. Upstairs, two generously sized bedrooms feature new hardwood floors and share a newly renovated full bath. The walk-out lower level offers exceptional additional living space, with new vinyl plank flooring, a versatile office that could also serve as a fourth bedroom, and a renovated full bath. With nearly every space thoughtfully updated, this move-in-ready home combines sophisticated design, modern amenities, and flexible living spaces in one of the most desirable South Wilton settings. Updates include: New Roof, New HVAC, New Kitchen, New Baths, Added Hardwood Floors...see complete list under Documents

13 Wilton Hills, Unit 13, Wilton

$799,000

2 Beds ⋅ 3 Baths ⋅ 24202024 MLS ⋅ Lambert Common Condo BLDG.

Welcome to 39 Lambert Common! This lovely townhouse has been meticulously maintained and cared for by the same owner for the past 39 years, and the pride of ownership truly shows. Located in the desirable Lambert Commons complex, where units are rarely offered for sale, this corner end unit offers over 1,700 sq. ft. of living space and a two-car garage. The bright and open main level features a sun-filled living room, dining room, half bath, eat-in kitchen, and a versatile bonus room-perfect for a den or home office. The living room features a fireplace and sliders leading to a 15x15 stone patio and private yard space surrounded by beautiful perennial plantings. A convenient walkway provides direct access to the garage. The second level offers two spacious bedrooms with double closets, a full bath, & laundry for added convenience. The primary bedroom suite features its own private full bath with a double vanity & new stall shower. There is plenty of storage throughout, along with a partially finished room in the basement-perfect for a playroom, rec room, or home gym-plus a separate storage/utility room. All custom window treatments are included. Recent improvements include newer windows and appliances, a newer roof, HVAC system (2024), water heater (2024), basement sink and pump (2024), and a new garbage disposal (2026). With no assessments and a location in this sought-after complex, this beautiful end unit is a rare opportunity you won't want to miss!

39 Lambert Cmn Unit 39, Wilton

$2,499,000

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

$999,000

3 Beds ⋅ 3 Baths ⋅ 24200382 MLS ⋅ Grumman Hill Village BLDG.

Welcome to Grumman Hill Village, a coveted South Wilton community that blends privacy, convenience, and true neighborhood charm. This 1,984 SF, 3-bedroom home stands out for its main-level primary suite and attached two-car garage. Lovingly maintained and freshly painted, the home welcomes you with a bright, open main level where the eat-in kitchen, dining area, and living room flow together seamlessly. A separate den offers a cozy retreat for reading, relaxing, or working from home. The main-level laundry room adds everyday convenience. Step outside to a private back patio, an ideal spot for morning coffee, al fresco dinners, or simply unwinding. Upstairs, two additional bedrooms share a full bath, offering comfortable space for family or guests. Grumman Hill Village is known for its close-knit community spirit, highlighted by a beloved Halloween tradition that brings neighbors together for one of the area's most festive trick-or-treating nights. Natural gas, city water, and city sewer, add everyday ease, while the South Wilton location puts Wilton Center, dining, top schools, train stations, and major commuting routes all within easy reach. This is a rare opportunity to enjoy space, privacy, convenience, and community in one of Wilton's most established and sought-after residential settings.

26 Village Court, Unit 26, Wilton

$2,099,000

6 Beds ⋅ 7 Baths ⋅ 24199595 MLS

Welcome to 40 Valeview Road, set on 2.27 private acres in South Wilton's most convenient neighborhood, just minutes to town, highways & trains to NYC. This 6-bedroom Colonial was built to do it all:cook, entertain & work from home. The kitchen anchors it all: high-end appliances, two islands for prepping and serving, with an open flow into the dining area & family room. A first-floor office with French doors provides a dedicated, private work from home space. The mudroom off the garage keeps everyday life organized.The primary suite is a genuine retreat, w/a gas fireplace, a custom walk-in closet & spa-like bath. Four additional bedrooms share the floor w/a dedicated playroom.The walk-up attic adds even more storage.The lower level includes a playroom with a fireplace and TV, a bedroom currently used as a gym, a full bath, and a flex space plus a sliding door outside: this level could be a possible in law/au pair suite. Even more storage in unfinished portion of the basement.Outside, the backyard is large, open and flexible:plenty of room to spread out.The patio is made for entertaining, all within a private, professionally landscaped yard with a possible pool site. As Wilton's first LEED/Energy Star-built home, 40 Valeview also delivers real efficiency where it counts: geothermal heating and cooling helps keep monthly utility bills noticeably lower. This is a home that was designed to be lived in and enjoyed fully - and it shows.

40 Valeview Rd, Wilton

$699,000

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

$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

$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

$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

$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

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