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44 Oak Ledge Ln, Wilton
$895,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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
39 Keelers Ridge Rd, Wilton
$15,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24217047 MLS
FOR SALE OR LEASE. ALSO AVAILABLE FOR RENT AT $15,000/MONTH. Tucked away on a private cul-de-sac in Wilton's sought-after Keelers Ridge neighborhood, this exceptionally maintained estate spans 2.28 acres of professionally landscaped grounds. Offering over 9,100+ sq. ft. of total finished space across the main residence and heated/cooled pool house, the property enjoys complete privacy and ideal positioning for both morning sunrises and evening sunsets. 9,100+ Sq Ft...Main House 6,115 sq. ft. Lower Level is finished with 1,995 sq. ft. and Pool House 1031 sq. ft. The main residence features 5 bedrooms, 4 full and 3 half baths, including a convenient main-level bedroom suite. The finished lower level adds dedicated space for a wine cellar, gym, rec room, plus 1,040 sq. ft. of unfinished basement for storage and utilities. A whole-house Crestron sound system (Sonos compatible) runs throughout. Designed for effortless indoor-outdoor entertaining, two expansive stone patios-each equipped with its own outdoor kitchen-overlook the gardens, newly built cedar pergolas, and heated pool with spa. Topped with a classic cupola, the pool house includes central HVAC, a full bath, kitchenette, and a 740 sq. ft. unfinished basement-ideal for poolside hosting and relaxation. Major mechanicals and upgrades: new roof and gutters (2026), new HVAC system (2024), whole-house generator (2021/22).

39 Keelers Ridge Rd, Wilton
39 Keelers Ridge Rd, Wilton
$3,795,000
5 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24215990 MLS
FOR SALE OR LEASE. ALSO AVAILABLE FOR RENT AT $15,000/MONTH.Tucked away on a private cul-de-sac in Wilton's sought-after Keelers Ridge neighborhood, this exceptionally maintained estate spans 2.28 acres of professionally landscaped grounds. Offering over 9,100+ sq. ft. of total finished space across the main residence and heated/cooled pool house, the property enjoys complete privacy and ideal positioning for both morning sunrises and evening sunsets. 9,100+ Sq Ft...Main House 6,115 sq. ft. Lower Level is finished with 1,995 sq. ft. and Pool House 1031 sq. ft. The main residence features 5 bedrooms, 4 full and 3 half baths, including a convenient main-level bedroom suite. The finished lower level adds dedicated space for a wine cellar, gym, rec room, plus 1,040 sq. ft. of unfinished basement for storage and utilities. A whole-house Crestron sound system (Sonos compatible) runs throughout. Designed for effortless indoor-outdoor entertaining, two expansive stone patios-each equipped with its own outdoor kitchen-overlook the gardens, newly built cedar pergolas, and heated pool with spa. Topped with a classic cupola, the pool house includes central HVAC, a full bath, kitchenette, and a 740 sq. ft. unfinished basement-ideal for poolside hosting and relaxation. Major mechanicals and upgrades: new roof, gutters and downspout (2026), new HVAC system (2024), whole-house generator (2021/22).

39 Keelers Ridge Rd, Wilton
82 Old Mill Rd, Wilton
$1,049,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24216404 MLS
Welcome to 82 Old Mill Road, the perfect balance of privacy and convenience, along with the luxury of an inground pool surrounded by bucolic landscaping. This well-maintained and spacious 3 bed, 2 1/2 bath home is perfectly situated on a secluded acre just steps from Georgetown's restaurants and shops. With almost 2,400 square feet of move-in ready living space, there is room for all. A light-filled and updated eat-in kitchen features new appliances and sliders to the generous backyard patio. Find a welcoming living room with a wood-burning fireplace and picture window, and formal dining room with built-ins. A convenient bedroom and full bath complete the first floor. Upstairs find a generous, light-filled primary bedroom with a private bathroom, and another spacious bedroom, both with ample storage. The finished basement provides even more living space with a large recreation room, wet bar, and half bathroom-perfect for movie nights, watching sports, or entertaining friends. Your outdoor oasis awaits with beautiful mature landscaping, large patio and heated gunite pool, creating a private setting for relaxing and gathering. Find more storage above the attached 2-car garage that features epoxy flooring and entrance to the sunny mudroom. Set along a private road, this opportunity to feel away from it all while close to both Georgetown and Wilton Center, is not to be missed!

82 Old Mill Rd, Wilton
52 Wilton Crest, Unit 52, Wilton
$4,350
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215345 MLS
Immaculate, spacious, and sun-filled townhouse with an attached garage and beautiful new hardwood floors. The inviting living room features a cathedral ceiling, a wood-burning fireplace, and sliders leading to a private balcony. The open layout creates a bright and comfortable living space. The main-level primary suite offers multiple closets and a full bathroom with double sinks, a separate shower, and a Jacuzzi tub. Upstairs, the second en-suite bedroom provides additional privacy and comfort, with its own full bathroom. The finished lower level has two additional rooms, ideal for a home office, exercise room, or extra living space, along with a convenient laundry room. Enjoy comfortable, low-maintenance living in a desirable community. Walk to shopping, restaurants, and train. A wonderful opportunity for anyone looking for a spacious, well-maintained home in a convenient location! Fabulous commuting location.

52 Wilton Crest, Unit 52, Wilton
58-60 Langner Ln, Wilton
$4,100
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24215789 MLS
Welcome to your own private cottage on one of Wilton's most scenic roads. Nestled on a quiet country estate, once a part of the Sturgis Farm property, this 3 bedroom 1 full and half- bath home offers privacy and the convenience of proximity to both Wilton and Weston. Charm abounds inside this updated cozy antique, yet is very livable for today's lifestyle. The large modern Kitchen features, dining area, new sliding doors that lead to a large deck for entertaining, as well as laundry on the main floor. The Living Room runs front to back of the house, is flooded with warm afternoon light from the many windows, and has access to the main floor half-bath. There is also an additional room off the front foyer which could be used as needed for a Home Office or Guest Bedroom. Upstairs are 2 full -sized bedrooms, and a full- sized bathroom with a tub and shower. This charming antique home was recently refreshed with newly refinished hardwood floors, freshly painted interiors & exterior, new kitchen floor, a new vanity in the half bathroom, and a new roof. Ready for you to move in and enjoy your peaceful morning coffee and evening sunsets from your own private deck surrounded by mature shade trees. Don't miss this unique opportunity to make Wilton your home.

58-60 Langner Ln, Wilton
22 Hubbard Rd Unit 306, Wilton
$7,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215346 MLS
NOW OFFERING 1 MONTH FREE WITH A ONE-YEAR LEASE! Discover our largest single-level, 3-bedroom residence at The Wilton Center Lofts, offering an impressive 1,771 square feet of thoughtfully designed living space, 3 spacious bedrooms, and 2.5 luxurious bathrooms. A standout feature is the HUGE private deck, accessible from both the primary bedroom and main living area, providing exceptional indoor-outdoor living. Designed by award-winning Granoff Architects, this sophisticated residence showcases 9-foot ceilings, oversized windows, beautiful wood-grain flooring, and premium finishes throughout. The gourmet kitchen features quartz countertops, stainless steel BOSCH appliances, custom cabinetry, and elegant fixtures. Generous walk-in closets and an in-unit washer and dryer add everyday convenience. Residents enjoy a fitness center, stylish lounge, covered parking, and available storage. Pet-friendly, too! COMMUTER'S DREAM! Just a 7-minute walk to Metro-North, offering convenient access to NYC and beyond. Experience exceptional space, modern luxury, and sophisticated design in the heart of Wilton Center. Schedule your private tour today!

22 Hubbard Rd Unit 306, Wilton
23 Church St, Wilton
$819,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24214965 MLS
This captivating 3-bedroom, 1.5-bath antique Colonial is ready for its next chapter. Celebrated by The New York Times, Realtor.com, and Homes.com for its distinctive character, this home offers the ultimate blend of historic integrity and modern ease. The delightful, light-filled interior was designed for effortless, low-maintenance living. Sunlight pours through oversized windows, illuminating wide-plank floors and an updated granite kitchen. French doors lead to a private stone patio, looking out on 1.49 professionally landscaped acres with classic stone walls, native gardens and serene outdoor spaces. The main level features a dramatic dining room with a skylight, a spacious living room with a cozy reading nook and wood stove, plus a main-level laundry room. Upstairs, a vintage-inspired full bath accompanies 3 charming bedrooms, including a primary suite with a large walk-in closet. Listed on the National Register of Historic Places, the property is a part of the Pollinator Pathway Project and a Certified National Wildlife Habitat. Located in Wilton's Historic District, this home trades the burden of an oversized footprint for an efficient, lock-and-go sanctuary. Best of all, you are just a short stroll to Georgetown's vibrant cafes, restaurants, and Caraluzzi's Market. Complete with city water, total privacy, and easy access to Route 7 and Metro-North, this is a perfectly priced masterclass in historic charm.

23 Church St, Wilton
561 Belden Hill Rd, Wilton
$1,099,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24214013 MLS
HIGHEST & BEST TO BE SUBMITTED BY TUESDAY, OCTOBER 27th at 4:00pm. NO ESCALATION CLAUSES PLEASE. Welcome to 561 Belden Hill Road! A beautiful, move-in-ready 4 bedroom 3 bath home set on 2+ acres of beautifully landscaped property in desirable South Wilton with CITY WATER. Unique combination of a convenient commuting location with generous living spaces and an incredible flat, private yard. The perfect balance of everyday comfort, entertaining, and outdoor enjoyment. Inside, gracious well-proportioned rooms with plenty of space for family and friends. The eat-in kitchen opens to a bright expansive sunroom with peaceful views of the surrounding grounds. The elegant living room with custom built-ins and gas fireplace flows into the dining room. A comfortable family room with gas fireplace, along with a full bath and laundry room. Upstairs you will find 4 generously sized bedrooms including the primary bedroom suite w/walk-in closet, and 3 other bedrooms and full bath providing comfortable accommodations for family and guests. The lower level offers a spacious bonus room with endless possibilities for a playroom, home office, media room, or recreation space. The outdoor setting is truly exceptional. An attached 2-car garage is complemented by an oversized detached garage with a loft. Ideally situated in South Wilton, this home offers easy access to the Merritt Pky, I-95, shopping, town amenities, and Wilton's award-winning schools. SELLERS PREFER end of Feb. closing

561 Belden Hill Rd, Wilton
68 Wilton Crest, Unit 68, Wilton
$4,350
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24213947 MLS ⋅ Wilton Crest BLDG.
Welcome to this light-filled, contemporary 2 bedroom, 2.5 bath townhouse, ideally situated in one of South Wilton's most convenient locations! Soaring ceilings, skylights, and an abundance of natural light create a bright, airy atmosphere throughout. The spacious kitchen features new stainless steel appliances and opens to a private, enclosed deck, also accessible from the primary suite. The inviting living room offers multiple exposures, a cozy fireplace, and a private balcony all perfect for relaxing or entertaining. The generously sized first-floor primary suite boasts cathedral ceilings and a beautifully updated, spa-inspired bathroom featuring a luxurious soaking tub and separate shower. Upstairs, a second bedroom and full bath provide a comfortable and private retreat for guests or family. The expansive lower level ( the largest in the complex!) includes a finished office/playroom, ample room for a home gym, exceptional storage, and direct access to the attached one-car garage. Additional highlights include central air, second floating parking space, and plenty of guest parking. Enjoy resort-style amenities, including a pool and tennis courts, all just moments from South Wilton's shops, restaurants, and Metro-North. An exceptional combination of space, natural light, comfort, and convenience. A wonderful opportunity not to be missed!

68 Wilton Crest, Unit 68, Wilton
175 Range Rd, Wilton
$1,075,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24214464 MLS
Thank you for the strong interest! OFFER DEADLINE, 10/19 @ 10am ET. Ideally situated in South Wilton, 175 Range Road blends charming character with modern comfort and everyday convenience. Just minutes to town, train, schools, and commuter routes, the home enjoys a private setting framed by professional landscaping, flowering perennials and accent trees, an expansive front lawn, and a beautiful stone patio out back, ideal for entertaining or quiet relaxation. Inside, architectural details shine with warm wooden beams, custom kitchen design, wide plank flooring, a vaulted ceiling, pocket doors, and an original stone fireplace. The kitchen features custom cabinetry, while the living and family rooms offer warm and bright gathering spaces. A sound system, natural stone half bath, and custom closets complete the first floor. The stunning primary suite feels like a private retreat, offering expansive windows, and a beautifully appointed ensuite bath with natural stone, a soaking tub, separate shower, and radiant heated floors. Additionally, the primary offers four closets including a spacious walk-in as well as a cedar closet. Two additional, well-proportioned bedrooms and hallway bath complement the upstairs. Completing the second floor is a spacious loft overlooking the kitchen offering numerous possibilities. An oversized two-car garage provides ample storage and flexibility. Distinctive, inviting, and exceptionally located, this is South Wilton living at its beh

175 Range Rd, Wilton
84 Turtleback Rd, Wilton
$899,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24213525 MLS
Nestled on a picturesque stretch of bucolic Turtleback Road-a long-time favorite route for local walkers-this inviting 3-bedroom, 2-bathroom ranch offers a rare connection to Wilton's historic pastoral roots. Once part of a cherished local dairy farm, the property carries a peaceful, storied atmosphere that's hard to find. Inside, the home feels bright, refreshed, and rejuvenated, boasting beautiful refinished hardwood floors and a fresh coat of paint throughout an effortless, single-level layout. While the interior shines, the view out of every window truly steals the show. The property backs directly onto expansive woodlands, offering easy access to miles of hiking leading to the historic Weir Farm National Historical Park. Sweeping views from the expansive picture windows and the tranquil sunroom provide a front-row seat to a rolling meadow and the changing New England seasons. It is the exact kind of peaceful backdrop that turns a morning cup of coffee into a daily retreat. Practicality meets country charm, with two separate driveways-the upper drive serving the main level, and the lower drive offering direct, convenient access to covered parking and the walk-out lower level. A brand-new 4-bedroom septic system delivers absolute peace of mind, along with the potential to expand the footprint down the road. Enjoy a true single-level oasis located equidistant to Wilton Center, Ridgefield's historic Main Street, and trendy Georgetown.

84 Turtleback Rd, Wilton
5 Deerfield Rd, Wilton
$9,200
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24212197 MLS
An exceptional rental offering in South Wilton, 5 Deerfield Road pairs the architectural drama of a historic barn home with the comforts of a distinctive Connecticut retreat. Set on a cul-de-sac, the residence offers soaring 11-foot ceilings, walls of glass, and monumental timber beams reclaimed from Manhattan's iconic Ruppert Brewery-a striking connection to its New York heritage. Built in 1969 with portions dating to the 1700s, the home blends rich texture and historic character with generous spaces for entertaining and everyday living. A chef's kitchen anchors the main level, complemented by impressive living and dining rooms, an office, an ensuite bedroom, and a powder room. Upstairs, the primary suite features an expansive walk-in closet, while two additional bedrooms include one with a loft. The lower level provides flexible space for recreation, fitness, or a studio, along with a half bath, laundry, and wine cellar. South Wilton offers an appealing balance of New England character and everyday convenience. Wilton Center's local shops, restaurants, and cultural offerings give the town a vibrant gathering place, while the Norwalk River Valley Trail and surrounding preserved open spaces invite time outdoors. The artistic legacy of Weir Farm National Historical Park adds another distinctive dimension to a town where history, nature, and creativity remain part of daily life. Whether envisioned as a full-time residence or a weekend escape from the city, this remarka

5 Deerfield Rd, Wilton
39 W Meadow Rd, Wilton
$1,550,000
8 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 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
467 Nod Hill Rd, Wilton
$1,295,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24212625 MLS
There are houses that simply have a feeling about them, and this is one of those rare homes. Designed in 1938 by noted architect F. Nelson Breed, this enchanting country home is beautifully sited on three open, picturesque acres along Nod Hill Road, one of Wilton's designated scenic roads. From the moment you arrive, the charm is undeniable. A gracious approach and beautifully landscaped grounds set the tone. Inside, approximately 1,883 square feet is filled with warmth, character and architectural detail, thoughtfully updated while preserving the charm and integrity of the original home. The home offers three bedrooms and two and a half baths, along with additional flexible rooms ideal for a home office, den, studio or guest space. Lovely views of the property and an easy connection to the outdoors enhance the sense of true country living. Open lawns, mature trees and established plantings create a peaceful backdrop. Nearby meadows, trails and adjacent town-protected land further enhance the setting, with Weir Farm National Historical Park just minutes down the road. Ideally located between Wilton and Ridgefield centers, the property offers country living with convenient access to both towns. Branchville Metro-North station is 7 minutes away, South Norwalk station is approximately 20 minutes away, and NYC is an hour by car. Charming, distinctive, and rich in history, this is a rare opportunity to own a truly special home!

467 Nod Hill Rd, Wilton
140 Vista Rd, Wilton
$1,050,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24181173 MLS
4.74 Acres! First time on the market! Acreage reflects only 1 of 2 parcels. 1.84(house)+2.90 acres of pristine, lush property with main house, authentic Post and Beam Barn and in ground Gunite Shoreline pool. Once in a lifetime opportunity to create your weekend getaway, dream vacation compound or year round home to your personal specifications. Rarely does a property with this much character, acreage and pure potential hit the Fairfield County market. One conveyance of 2 contiguous parcels totaling 4.74 acres, on the NY border, in one of Wilton's most coveted neighborhoods, this secluded sanctuary is for visionaries, design enthusiasts, or anyone looking for the ultimate living opportunity. This estate is anchored by 3 incredible features: 1. Main House, a huge, mid-century modern feel, 1-2 Bedroom awaiting your imagination with remarkable potential, excellent bones, spacious proportions and a layout begging for modern transformation. Craft a sleek high-end masterpiece! 2: Majestic Post and Beam Barn w/ loft, steeped in character and limitless utility for entertainment space, convert to guest house or studio, or for your car collection, home fitness center or huge home office! Barn wood from the 1800's. 3. Vintage Shoreline Gunite Pool and grounds perfectly situated between house and barn, surrounded by nature, majestic trees and absolute tranquility. Plenty of room to expand the outdoor living space into an entertainer's paradise. Separate tax on vacant parcel. SOLD AS IS

140 Vista Rd, Wilton
21 School Rd, Wilton
$3,999,999
6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24212467 MLS
Welcome to an unparalleled masterpiece of living, nestled within a completely fenced, four-plus-acre private paradise in the very heart of Wilton, Connecticut. This extraordinary estate perfectly balances absolute serene privacy with the effortless convenience of town life. Approached via double-gated entries, the winding driveway unveils a residence meticulously crafted for the epicurean, the entertainer, and the modern visionary. The heart of the home centers around a true chef's kitchen, anchored by a roaring fireplace that radiates warmth and timeless character. Designed for both casual mornings and grand-scale catering, it features premium commercial appliances, a designated coffee bar room for your morning rituals, and endless custom storage to keep the aesthetic flawless. Just off the kitchen, a walk-in wine room awaits your private collection. For seamless entertaining, the formal sitting room features a fully equipped walk-in bar, transitioning beautifully into a stunning screened-in porch and a massive outside deck overlooking the grounds. Offering a total of six luxurious bedrooms, the home's layout is brilliantly engineered for ultimate privacy. The Owner's Suite and Family Quarters are situated in the main expanse of the home, offering opulent retreats with peaceful views of the estate.

21 School Rd, Wilton
39 Powder Horn Hill Rd, Wilton
$1,799,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24210618 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
267 Westport Rd, Wilton
$1,595,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24210329 MLS
Tucked away on a private, wooded two-acre lot in South Wilton, this 1890 antique farmhouse pairs quintessential New England character with expansive, light-filled proportions and a luxury pool complex completed in August 2025. The crowning jewel is the spectacular heated saltwater pool, seamlessly integrated into a sprawling custom stone paver deck sitting atop a majestic 10-foot natural boulder wall. Complete with a custom pool bar and a built-in automatic cover, this elevated terrace creates an unmatched private entertainer's paradise. Inside, the home has been freshly prepared for its next chapter with crisp white paint throughout and beautifully refinished original hardwood floors. Unlike typical antiques, the layout boasts grandly scaled rooms, high ceilings, and windows that flood the space with light. The main level flows through a formal living room with a classic fireplace, a generous formal dining room, an expansive family room, and a sun-filled eat-in kitchen featuring terracotta tile flooring. Two separate four-season rooms offer exceptional flexibility - one overlooks the pool, while the other features a floor-to-ceiling brick fireplace with French doors opening to a high deck nestled in the mature tree canopy. A private home office and separate study complete the main floor.

267 Westport Rd, Wilton
143 Chestnut Hill Rd, Wilton
$2,375,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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 Fu baths. The finished walk-out lower level adds versatility with a playroom, kitchenette, office/bedroom and full bath. Outdoors, enjoy a mahogany deck, bluestone patio, fire pit, plus an approx. 2,500 SF heated/cooled barn w/ office, kitchenette, bed/bath.

143 Chestnut Hill Rd, Wilton
14 Powder Horn Hill Rd, Wilton
$2,195,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 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
98 Old Boston Rd, Wilton
$1,049,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24201924 MLS
**Due to much interest, we are asking all offers be presented by Tuesday 9/29 at 5:00pm** A little more space. A little more privacy. And everything else still close. Tucked away on 3+ acres in Wilton's Silvermine area, this home offers the breathing room people come to Wilton for, with everyday conveniences surprisingly close by. A long driveway winds through the wooded acreage before the property opens to a level lawn framed by mature trees. Inside, there's an easy comfort to the way this home lives. The eat-in kitchen opens to a cozy fireside sitting room with access to the patio-a natural spot for morning coffee, homework, or unwinding at the end of the day. A spacious family room offers another place to gather, while the separate dining room is ready for holidays, dinner parties, and everything in between. Upstairs, four comfortable bedrooms create a natural separation from the main living spaces, including a primary suite with a private bath. The finished lower level adds even more flexibility for movie nights, play space, a home gym, or whatever life calls for next. Move-in ready with room to make it your own, this is a home that can evolve right along with you, with the added benefit of public water, a welcome rarity in Wilton. And perhaps the biggest surprise is just how connected you are-minutes to Wilton Center, schools, the train, New Canaan, and the Merritt Parkway. Maybe Wilton is closer than you think.

98 Old Boston Rd, Wilton
231 Rivergate Dr, Wilton
$6,695
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24208754 MLS
Spacious 5-bedroom Colonial set on 2.16 acres in desirable South Wilton, offering an ideal combination of privacy, space, and convenience. The 3,575 sq. ft. main residence features a first-floor primary suite with vaulted ceiling, skylight, private bath, and generous closet space. The open-concept kitchen, dining, and living areas provide a comfortable flow for everyday living and entertaining, complemented by two fireplaces. A separate den/home office and spacious family room add flexibility to the main level. Upstairs are four additional bedrooms and two full baths. The home also features a finished lower level, enclosed porch, patio, and garage. The property also includes a separate 660 sq. ft. accessory dwelling with 1 bedroom and 1 bath, available to the tenant for an additional cost. An excellent option for those seeking additional living space, a private home office, or flexible accommodations. Please inquire for additional details and pricing. Enjoy a large, level property in an established neighborhood with convenient access to Wilton Center, schools, Metro-North, the Merritt Parkway, shopping, dining, and area trails. A rare opportunity to enjoy exceptional space, privacy, and flexibility in a convenient South Wilton location. Available date is 12/01/2026.

231 Rivergate Dr, Wilton
46 Fawn Ridge Ln Unit 46, Wilton
$600,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24207874 MLS ⋅ Fawn Ridge BLDG.
Ideally situated on the Norwalk/Wilton line, this beautifully maintained condominium offers privacy, comfort, and an unbeatable commuter location. Set toward the back of the complex, the unit enjoys a peaceful, tucked-away feel, with the kitchen window, dining area, and private deck all overlooking natural surroundings rather than passing traffic or neighboring units. Inside, the living room's floor-to-ceiling windows fill the space with natural light, while the multi-level layout creates distinct living zones: a welcoming entry, garage access, and laundry on one level, an open kitchen and living area with a spacious island offering abundant prep space and storage, and bedrooms upstairs for a cozy, private retreat away from the main living areas. The upper level features a double-sinks in the primary bedroom, allowing two people to get ready at once with ease. Generously sized rooms throughout and abundant closet space provide comfortable, flexible living. An attached garage adds everyday convenience. Residents enjoy access to the pool and tennis courts, and the location cannot be beat: close to shops and restaurants, yet quiet within the complex, with easy access to major commuting routes and New York city.

46 Fawn Ridge Ln Unit 46, Wilton
20 Cherry Ln, Wilton
$2,495,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24206331 MLS
A magnificent Colonial estate offering an extraordinary blend of elegance, privacy and resort-style living on 2.45 beautifully manicured acres, adjoining 50 acres of conservation land. Grand in scale yet thoughtfully designed for today's lifestyle, the residence features 6 bedrooms, 6 full and 1 partial bath, including a sumptuous primary suite with two walk-in closets, dressing room, spa bath and private balcony overlooking the tranquil grounds. Five additional bedrooms offer en-suite baths, with two featuring walk-in closets. A dramatic two-story foyer introduces gracious formal living and dining rooms, two private offices and a handsome library. At the heart of the home, a newly renovated chef's kitchen features double marble islands, dual ovens and dishwashers, navy subway tile backsplash, wine fridge and custom coffee bar, flowing seamlessly into the inviting family room with fireplace. The spectacular great room is designed for memorable entertaining, with soaring ceilings, floor-to-ceiling stone fireplace, full bar with beverage refrigerator and direct access to the restored pool and spa, expansive deck, sport court and terrace. The finished lower level adds a gym, wine cellar and generous playroom with built-in bunk beds. A four-car garage and attached one-bedroom apartment provide exceptional convenience and flexibility for guests or multi-generational living. An exceptional private retreat in a coveted location near award-winning schools.

20 Cherry Ln, Wilton
20 Mountain Rd, Wilton
$975,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24206963 MLS
Amazing value in Wilton! Extensively updated, this charming Colonial offers the perfect blend of classic character and modern convenience. Featuring a newly renovated kitchen, updated bathrooms, refinished hardwood flooring, a new heating system, updated electrical, a new roof, and fresh paint throughout. Among others, a new well cap adds to the list of important improvements. The warmth and character has been thoughtfully preserved, which is what makes this home so special. Ideally located just minutes from town, schools, shopping, dining, and commuter routes, 20 Mountain Road is a wonderful opportunity to enjoy all that Wilton has to offer in a home that is truly move-in ready.

20 Mountain Rd, Wilton
149 Dudley Rd, Wilton
$2,995,000
5 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24207078 MLS
Originally built in 1726 and extensively remodeled, reimagined and re-engineered in 2007, 149 Dudley Road is a rare country estate where nearly three centuries of history meet sophisticated modern living. Set behind gates on more than five magnificent level acres, this exceptional property combines timeless New England character, beautifully considered interiors and extraordinary amenities in an idyllic, park-like setting. The main residence is warm, elegant and filled with natural light, with wide-board floors, handsome millwork, dramatic stone fireplaces, original architectural details and inviting covered and wraparound porches that honor the home's remarkable heritage. Generously scaled rooms and an open, effortless flow are complemented by a stunning kitchen and beautifully appointed baths featuring luxurious finishes that are both classic and timeless. Designed equally for intimate everyday living and memorable entertaining, the home extends seamlessly outdoors. An exceptional outdoor living room with fireplace and pergola, expansive tiered terraces, heated pool and spa create a private resort-like setting surrounded by mature landscaping, sweeping lawns and a picturesque freshwater pond. Adding another dimension to the property is the extraordinary three-story carriage barn-a destination unto itself. With expansive entertaining and recreation spaces, offices, a spectacular secret "Speak Easy" and extensive garage and storage capacity for car collections, boats

149 Dudley Rd, Wilton
100 Glen Side, Unit 100, Wilton
$579,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24206763 MLS ⋅ Glen River BLDG.
Welcome to this centrally located two-bedroom, two and a half bath condo in Wilton Center. The open first floor layout offers easy flow for everyday living, and a one-car garage adds convenience. With some updates and personal touches, this home presents a wonderful opportunity to create value in a sought-after location, just moments from local shops, restaurants, and commuter routes.

100 Glen Side, Unit 100, Wilton
300 Sturges Ridge Rd, Wilton
$4,695,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24206380 MLS
Within easy reach of Manhattan, 300 Sturges Ridge Rd is a private modern retreat created for an extraordinary way of living. Set on 2.6 beautifully landscaped acres adjoining protected open space, the property offers exceptional privacy in a spectacular natural setting. Walls of glass, soaring ceilings and abundant natural light create interiors that feel open and connected to the outdoors. The sophisticated Poliform kitchen is a natural gathering place for quiet evenings or a house full of friends. The private primary suite opens to a balcony overlooking the grounds, while a dramatic glass mosaic wine cellar and expansive skylit gym add unexpected spaces for everyday enjoyment. Outside, a heated saltwater pool and spa are surrounded by lush landscaping, with multiple terraces, an outdoor kitchen, fire pit and Zen garden for entertaining and unwinding. Passive solar principles, advanced HVAC, a generator and whole-property connectivity support effortless modern living. This is luxury that feels personal rather than formal-a home for summers by the pool, evenings with friends, quiet mornings surrounded by nature and weekends that feel like a true escape without ever leaving home. For those seeking a distinctive modern home or private retreat near New York City, 300 Sturges Ridge brings together exceptional design, resort-style amenities, beautiful acreage and proximity to Manhattan.

300 Sturges Ridge Rd, Wilton
122 Millstone Rd, Wilton
$1,795,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24204152 MLS
The most spectacular and unique offering in Wilton! Welcome to "La Barn," a chic estate where timeless character meets exceptional design and resort-style living. Originally a barn, this extraordinary home has been thoughtfully expanded, renovated, and lovingly maintained over the last century, creating a one-of-a-kind property rich in charm, history, and modern comfort. At its heart is a showstopping newly renovated kitchen blending mid-century warmth with clean, contemporary design. The main residence features four bedrooms, three full and one half baths, along with a newly finished walk-out lower level complete with a full bath and walk-in closet, ideal as a guest suite, gym, office, or recreation space. Resort-like grounds invite effortless entertaining and relaxation, highlighted by a recently converted and heated saltwater pool, sweeping lawns, and exceptional privacy. Above the three-car garage, a separate studio offers an additional bedroom, full bath, kitchen, and laundry, providing remarkable flexibility. Adding to the property's rare appeal is an additional barn with horse stalls, offering an exceptional opportunity, with convenient access to Wilton, Ridgefield, New Canaan, and the best of Fairfield County.

122 Millstone Rd, Wilton

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