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89 Chestnut Hill Rd, 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

143 Chestnut Hill Rd, Wilton
$2,375,000
6 Beds ⋅ 6 Baths ⋅ 24208606 MLS
143 Chestnut Hill blends more than a century of character with extraordinary craftsmanship and modern-day function. Built in 1900, with just three owners and lovingly curated by the current owners for over 40 years, the home has been thoughtfully expanded while honoring its original wide-board floors, stonework, doors, millwork and reclaimed antique beams. Throughout, extensive custom cabinetry was designed specifically for each room, with inset dressers, drawers, armoires and ingenious storage creating a true place for everything. At the heart of the home is a spectacular chef's kitchen with a 7ft island topped in reclaimed white oak, 48" Bertazzoni range, Danby marble, Sub-Zero refrigerator, and Rohl Shaw sinks. Gracious living spaces include an oversized dining room, sunroom with authentic stone wall and beams, family room with original stone fireplace and mudroom with travertine floors. A main-level en-suite bedroom and elevator provides exceptional flexibility for a first-floor bedroom suite. Upstairs, you will find a light-filled primary suite featuring extensive built-ins, walk-in closet and lux. bath, plus 4 add'l beds/3 full baths. The finished walk-out lower level adds versatility with a playroom and office space. Outdoors, enjoy a mahogany deck, bluestone patio, fire pit, plus an approx. 2,500 SF Barn.

143 Chestnut Hill Rd, Wilton

77 Old Boston Rd, 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

14 Powder Horn Hill Rd, Wilton
$2,195,000
5 Beds ⋅ 6 Baths ⋅ 24208913 MLS
Set on a private, beautifully landscaped two-acre property, 14 Powder Horn Hill Road offers exceptional space, privacy and convenience just minutes from Wilton town center, shopping and the train. A stunning front porch creates a memorable first impression and opens to a grand entry foyer with a sweeping staircase. Inside, rich hardwood floors, generous room sizes, high ceilings and thoughtful architectural details create an elegant yet comfortable atmosphere. The spacious chef's kitchen features a large center island, Sub-Zero refrigeration and abundant workspace, flowing seamlessly into the inviting family room with coffered ceilings, a fireplace and French doors leading to the deck. Formal living and dining rooms provide ideal entertaining spaces, while a private library offers the perfect home office or quiet retreat. Upstairs, the expansive primary suite features a fireplace, luxurious bath and two exceptionally large walk-in closets. Four additional bedrooms and an oversized playroom room with a full bath offer outstanding flexibility for guests, recreation or media. The walk-out lower level is a true blank canvas, featuring impressive 9-foot ceilings, plumbing already in place for a future bathroom and endless potential to create a gym, home theater, game room, guest suite or additional living space. Outside, the flat, fenced backyard offers an ideal setting for entertaining, play and pets, with ample room for a future pool.

14 Powder Horn Hill Rd, Wilton

39 W Meadow Rd, Wilton
$1,550,000
8 Beds ⋅ 5 Baths ⋅ 24207928 MLS
A true New England Classic- 39 West Meadow Rd was built in 1931 in "The Meadows," a neighborhood of architecturally significant homes. Upon entering the foyer, you are greeted by a sweeping staircase with grand living and dining rooms on either side. Each room offers gracious space for gathering and entertaining, showcasing timeless original craftsmanship, including beautifully carved mantel, fireplace, built-in corner china cabinets, and elegant dentil molding. The kitchen features Viking & LG stainless steel appliances and an eat-in dining area with French doors to a private bluestone patio. A spacious family room/den off the living room is ideal for movie night, game days, or possible home office. Above the garage, an au-pair or in-law suite offers 2 bedrooms, a full bath, and a private entrance, as well as a mudroom and laundry area off the kitchen. Continue to the upper levels of the main house, and you will find 6 additional private bedrooms. The 2nd floor hosts 4 oversized bedrooms, including a Primary en-suite, as well as a hall bath, while the light and bright 3rd floor offers 2 more bedrooms and a full bath. Outside, mature trees and gardens with specimen plantings bloom with color throughout the seasons. Relax on the bluestone patio and enjoy your own private oasis- a rare opportunity to own this Classic Beauty in South Wilton!

39 W Meadow Rd, Wilton

12 Crowne Pond Ln Unit 12, 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

22 Bittersweet Trl, 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

44 Oak Ledge Ln, Wilton
$895,000
3 Beds ⋅ 2 Baths ⋅ 24217045 MLS
Nestled in the woods in South Wilton, this lovely three bedroom home offers an abundance of space for family, friends and everyday living. The welcoming main level features a cozy living room with fireplace, dining room, kitchen with adjoining breakfast room, an oversized family room and a full bath. One of the home's true highlights is the 410 sq. ft. screened porch - a wonderful three season extension of the living space with plenty of room to dine, lounge, entertain friends or simply relax and enjoy the beauty of the surrounding landscape! Upstairs are three generously sized bedrooms, a full bath and convenient access to attic storage above the family room. The lower level adds even more versatility with an enormous recreation room, a large storage area, laundry and direct access to the two car garage. Outside, the beautifully landscaped property has been thoughtfully and meticulously cared for by the current owner, creating a peaceful setting that feels tucked away while still enjoying the convenience of South Wilton and the close proximity to Miller Driscoll school, downtown Wilton Center and train.

44 Oak Ledge Ln, Wilton

12 Lambert Cmn Unit 12, Wilton
$799,000
3 Beds ⋅ 3 Baths ⋅ 24214507 MLS ⋅ Lambert Common Condo BLDG.
Welcome to 12 Lambert Common, a spacious three-bedroom, two-and-a-half-bath townhouse tucked away from the road in sought-after South Wilton. Offering three levels of living space and numerous recent improvements, this inviting home combines comfort, privacy, and convenience. The spacious living and dining area features hardwood floors, a fireplace, and sliders to a private stone patio with mature plantings and a peaceful space. The bright eat-in kitchen offers a charming bay window, new countertop, sink, faucet, disposal, and dishwasher. A powder room completes the main level. Upstairs, the generously sized primary bedroom features a private full bath, while two additional bedrooms share a hall bath. All second-floor windows have been replaced. The finished lower-level family room offers flexible space for entertaining, a home office, fitness, or recreation and a new high-performance washer and dryer. Additional highlights include storage, a new hot water heater, detached one-car garage, and assigned parking. Convenient to Wilton Center, Westport, New Canaan, Metro-North, shopping, dining, and major routes. With spacious interiors, thoughtful updates, and a tranquil setting, 12 Lambert Common offers comfortable, low-maintenance living. Please see the complete list of upgrades and improvements list in photos

12 Lambert Cmn Unit 12, Wilton

50 Wilton Crest Unit 50, Wilton
$648,000
2 Beds ⋅ 3 Baths ⋅ 24190757 MLS ⋅ Wilton Crest BLDG.
Light and bright town home at Wilton Crest, in the heart of Wilton. Quick close possible. 2 bedroom, 2 full and 1 half bath home 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

35 Glen Ridge, Unit 35, 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

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