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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
467 Nod Hill Rd, Wilton
$1,295,000
3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 24181173 MLS
Never before 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 ⋅ 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
160 Olmstead Hill Rd, Wilton
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 24211293 MLS
Located at the top of coveted Olmstead Hill, with rear views of spectacular 50 acre conservation/protected parcel of land. Classic Connecticut country home blends vintage farmhouse charm with thoughtful renovation and all of the modern conveniences. Sun-filled, fabulous open floor plan and loads of glass to bring the beautiful surroundings in! Chefs kitchen includes a gas fireplace, marble counter tops and high end appliances including built-in coffee maker with dedicated water line. There are two flexible, work from home locations on the second floor in addition to three bedrooms plus the primary bedroom with spacious, ensuite bath. GORGEOUS BARN WITH HEAT AND AC WAS COMPLETELY RENOVATED IN 2013. VERY SPECIAL, ADAPTABLE SPACE FOR MUSIC, ART STUDIO OR PARTIES. Recent improvements include exterior painting of barn, main house and detached garage in 2024. New oil tank 2025 and all hardwood floors throughout were sanded and refinished 2026, NEW 5 BEDROOM SEPTIC LEACHING FIELDS IN 2022. HOUSE IS 4 BEDROOMS. NEW FIELDS ARE NEAR BARN. WELL, MEANING WATER ACCESS IS ALSO NEAR BARN.

160 Olmstead Hill Rd, Wilton
61 Ryders Ln, Wilton
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 24206329 MLS
Set on one of Wilton's most sought-after cul-de-sac streets, this classic, turnkey Colonial offers 4,355 SF of finished living space, 4 bedrooms, and 3 full, 1 half baths. Thoughtfully renovated in 2023, updates include the roof, gutters, windows, kitchen, flooring, and interior and exterior paint. The chef's eat-in kitchen is the heart of the home, featuring a Wolf 8-burner range with double ovens, Sub-Zero, warming drawer, large center island, and generous workspace. Adjacent to the kitchen, the spacious family room features a gas fireplace and built-ins. Formal living and dining rooms flow beautifully for everyday living and entertaining, with gorgeous millwork throughout. Private office with dry bar, built ins and bay window make working from home a pleasure. A spacious mudroom with 1/2 bath, heated brick floors and built-in cubbies adds both charm and function. The inviting primary bedroom features a walk-in closet and luxurious bath with heated floors, spa tub, steam shower and sauna. Three additional bedrooms, a full, and second-floor laundry complete the upper level. Finished walk-out lower level offers flexible additional living space. A large year-round back porch overlooks the level backyard with plenty of room for play and entertaining. Whole-house generator and new, fully paid-for solar panels provide added peace of mind and significant energy savings. A beautifully updated home combining classic character, modern amenities, and a wonderful Wilton location.

61 Ryders Ln, Wilton
39 Powder Horn Hill Rd, Wilton
$1,799,000
5 Beds ⋅ 5 Baths ⋅ 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 ⋅ 24210329 MLS
Tucked away on a secluded two-acre property, this antique farmhouse offers exceptional privacy, fully fenced grounds, and a picturesque setting framed by mature trees. A newly added saltwater pool, thoughtful landscaping, and custom natural stone walls create a serene, resort-like retreat. Inside, historic character is complemented by grandly scaled rooms and soaring ceilings. The main level unfolds through gracious living spaces, including a formal living room with fireplace and built-ins, sun-filled eat-in kitchen, generous dining room, expansive family room, and two four-season rooms- one overlooking the pool and another with a fireplace and French doors to the deck. Nestled within the mature tree canopy, the deck offers an enchanting setting for dining, entertaining, or quiet afternoons. A private office, intimate parlor or study, and full bath complete the main level. Upstairs are three bedrooms and two full baths, including a spacious primary suite with fireplace, sitting or dressing area, and en-suite bath, plus a charming lofted playroom. The walk-out lower level offers a private fourth bedroom with en-suite bath, laundry room, and flexible space ideal for a gym, guests, au pair, or possible in-law use. Recent improvements include new Unico high-velocity air conditioning systems serving all three levels, a new 330-gallon Granby Ecogard oil tank, and a brand-new drinking water well.

267 Westport Rd, Wilton
33 Coley Rd, Wilton
$1,849,900
4 Beds ⋅ 4 Baths ⋅ 24209890 MLS
Experience a newly completed in 2026 turnkey luxury home in South Wilton, a beautifully reimagined 4-bedroom, 3.5-bath, 3,700sqft home where sophisticated design and extensive upgrades create effortless modern living. Major NEW addition featuring a 3-car garage and a luxurious Primary Suite above. The NEW designer custom kitchen features abundant cabinetry, a walk-in pantry, and all-new appliances. An elegant dining room flows into the spacious living room, where a wall of NEW windows fills the space with natural light. A large family room offers an inviting setting for entertaining and everyday living. Upstairs, the stunning brand-new-built Primary Suite is your private retreat with soaring 10+ ft vaulted ceilings, oversized windows, a room-sized walk-in closet, and a luxurious ensuite bath "to-die-for". Three additional generously sized bedrooms include one with an ensuite bath featuring a glass shower and double vanity, while the other two share a hall bath with a tub. A spacious second-floor laundry room adds convenience. Newly done hardwood floors run throughout. Extensive improvements include new HVAC, plumbing, electrical, windows, drywall, lighting, doors, trim, kitchen, appliances, and exterior walkways. Professionally landscaped grounds feature level, private lawns, a large deck with contemporary lighting, and a charming covered front porch. A whole-house Generac generator provides added peace of mind. Beautifully finished and available for immediate occupancy.

33 Coley Rd, Wilton
143 Chestnut Hill Rd, Wilton
$2,375,000
6 Beds ⋅ 6 Baths ⋅ 24208606 MLS
SELLERS WILL CONSIDER ALL OFFERS BROUGHT THIS WEEKEND, BY 5:00pm, Monday, 10/12/ 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 ⋅ 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 ⋅ 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
20 Cherry Ln, Wilton
$2,495,000
6 Beds ⋅ 6 Baths ⋅ 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 ⋅ 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 ⋅ 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
300 Sturges Ridge Rd, Wilton
$4,695,000
5 Beds ⋅ 5 Baths ⋅ 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
205 Mountain Rd, Wilton
$495,000
2 Beds ⋅ 1 Baths ⋅ 24207215 MLS
Marvelous opportunity at 205 Mountain Road in Wilton! This ranch-style home is set on approximately 1.60 acres with a lightly wooded, sloping lot. The property features one-level living, a screened porch, a private well, and a private septic system. Its existing layout offers a solid starting point for renovation and value creation. Update the current home, redesign the interior, or explore expansion possibilities, subject to town approvals. The property's natural setting provides privacy while remaining convenient to Route 7, shopping, dining, and nearby amenities. Ideal for investors, contractors, builders, or buyers seeking a renovation project in the Wilton market. Bring your plans and vision to unlock this property's full potential.

205 Mountain 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
315 Olmstead Hill Rd, Wilton
$849,000
3 Beds ⋅ 4 Baths ⋅ 24205671 MLS
Charming Cape Cod home in Wilton, a desirable Mid Fairfield County community. Located along a scenic country road, yet mere minutes from the village center, top ranked Schools and popular Wilton Y campus....Not to mention commute roads; and 5 mins from Cannondale Metro North train! 315 Olmstead Hill embodies classic New England architecture paired with unbeatable convenience. This comfortably-sized Cape, with significant, quality additional space in the partially Finished Walk-Out Lower Level, offers maximum flexibility for a wide range of lifestyles and life situations. The lush half-acre Lot possesses the perfect balance of lawn/perennial beds and Nature with its gorgeous views. There are Full Bathrooms on each Level. Some Key Features and Benefits: The Living Room with Dining Area is sun-lit, and anchored by a cozy stone Fireplace--ideal for crisp New England evenings. The home's Layout is Open and Inviting, including the main level Primary, with Walk-In Closet; 2 Bright Bedrooms upstairs; the Bonus Finished Lower Level; the Mud Room/Breezeway, separating the Oversized 2 Vehicle Attached Garage from the living quarters. Seamless flow from the timelessly Updated Kitchen with newer high-end Appliances, past the Breakfast Bar, to the Dining Area and Living Room. 315 Olmstead Hill is an outstanding opportunity to acquire a Move-In Home, or to customize a Classic Home in a convenient, highly desirable Location!!

315 Olmstead Hill Rd, Wilton
146 Westport Rd, Wilton
$895,000
3 Beds ⋅ 4 Baths ⋅ 24205136 MLS
A private retreat designed for easy, modern living. Tucked away from the road on 1.86 beautifully landscaped acres, this bright and airy ranch combines a sleek, clean aesthetic with an open concept floor plan and vaulted ceilings throughout. Thoughtfully maintained and move in ready, the main residence features an updated kitchen and baths, fresh interior and exterior paint, an enclosed porch, and a spacious primary suite with new wall to wall carpeting. Two additional generously sized bedrooms and a flexible layout easily accommodate a variety of lifestyles and needs. Adding exceptional versatility is a separate, ADU with a studio living space, private entrance, and separate parking. Peaceful and private yet convenient to town, schools, shopping and commuting, this turnkey home offers the rare combination of serenity, flexibility and effortless living. A portable generator is included. Estate Sale.

146 Westport Rd, Wilton
347 Nod Hill Rd, Wilton
$3,250,000
4 Beds ⋅ 5 Baths ⋅ 24168316 MLS
Set on one of Wilton's most coveted roads, this exceptional custom colonial is beautifully sited amid mature gardens, sweeping lawns and sunset views. Outdoor living is a highlight with a stunning pool, expansive stone patio, authentic Argentine Asado grill and level recreation lawn-an ideal setting for football and soccer games on Thanksgiving, entertaining and gatherings. Inside the main residence, timeless architecture, exquisite millwork, soaring ceilings and expansive windows create light-filled interiors. The renovated gourmet kitchen opens to gracious living spaces, including the great room with floor to ceiling stone fireplace, an elegant dining room for hosting large dinner parties and a warm and inviting family room with gas fireplace and built-ins. The first-floor primary suite features a sitting room, dual walk-in closets, built-ins and spa bath. Upstairs are three spacious bedrooms with window seats and a handsome home office. Connected by a breezeway, the 1,384 SF guest house offers a private entrance, bedroom, full bath, kitchenette, fireside living room, loft and additional living space.Attached and detached 2-car garages, potting shed, storage and circular drive complete this special property. This Nod Hill Road home is truly special.

347 Nod Hill Rd, Wilton
24 Graenest Ridge Rd, Wilton
$3,800,000
3 Beds ⋅ 4 Baths ⋅ 24201990 MLS
Mid-Century Modern, Reimagined. This singular residence is a compelling conversation between two architectural eras, where a gracious 1950s post-and-beam home designed by Robert Peterson, who studied under Mies van der Rohe, meets a striking contemporary addition by architect Zehra Kuz Mackin. The original structure, defined by its low-slung roofline and classic Mid-Century proportions, has been thoughtfully opened and refined, allowing light to move freely through beautifully composed interiors. Created to accommodate an art collection, guests and vintage automobiles, the zinc-and-glass addition introduces a distinctly modern vocabulary while remaining remarkably harmonious with the original architecture. A sculptural glass-and-steel staircase, gallery-like spaces, private guest suite and collector's garage blur the distinction between residence and exhibition space, yet the home remains inviting and eminently livable. The interior of the original house has been substantially renovated including a recent kitchen makeover. Beyond the glass, architecture gives way to landscape. A serene, spa-like pool creates an extraordinary sense of privacy and retreat. Rare, sophisticated and impossible to replicate, this is modernism not preserved in amber, but beautifully evolved.

24 Graenest Ridge 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
241 Mountain Rd, Wilton
$1,099,000
4 Beds ⋅ 3 Baths ⋅ 24198029 MLS
Move right into this extensively updated 4-bedroom Colonial, where the major work has already been completed. Set on 2.14 picturesque, professionally landscaped acres, this inviting home offers a renovated interior, abundant natural light and hardwood floors throughout the main living areas. The beautifully updated kitchen is designed for cooking and gathering, with generous workspace, abundant cabinetry, a breakfast bar and dining area. The spacious family room is anchored by a stone fireplace, while the dining room features French doors opening to a Trex deck and fenced backyard-perfect for everyday enjoyment and entertaining. A dedicated first-floor office provides valuable work-from-home space or flexibility for guests, while a remodeled powder room completes the main level. Upstairs, the generous primary suite includes a private bath and walk-in closet, accompanied by three additional well-sized bedrooms and a renovated hall bath. The finished lower level adds approximately 700 square feet of versatile living space for a playroom, media room, gym or recreation area. Extensive improvements include a new roof, updated electrical, propane conversion, tankless hot water, well and water-system updates, refinished hardwood floors and a finished garage. Major mechanicals and systems are four years old or newer. Convenient to Wilton schools, Georgetown, Wilton Town Center, Route 7 and Ridgefield.

241 Mountain Rd, Wilton
48 Old Farm Rd, Wilton
$5,190,000
4 Beds ⋅ 8 Baths ⋅ 24170471 MLS
Set beyond stone walls and a landscaped entrance, 48 Old Farm Road is a newly completed Wilton residence blending timeless New England architecture with a bright, refined modern interior. The open central hall makes an immediate impression with pale oak floors, abundant natural light and a striking staircase with black metal balusters. Generously proportioned living spaces feature custom millwork, expansive windows and seamless flow for everyday living and entertaining. The kitchen opens to the main gathering areas and overlooks the rear grounds. Spacious bedrooms include vaulted ceilings, large windows and beautifully finished baths with stone surfaces, frameless glass showers and thoughtfully selected fixtures. An elevator adds convenience between levels, while the three-car garage, broad driveway and multiple covered outdoor areas enhance daily function. Mature trees, open lawn, stonework and a private setting create the feel of a composed country property. An approved proposed pool is shown on the property survey, and the detached 2000 sq. ft. accessory building may be converted into a pool house, $620 per foot plus the pool. Served by Wilton Public Schools and convenient to Wilton Center, local amenities and Metro-North service to New York City.

48 Old Farm Rd, Wilton
206 Mountain Rd, Wilton
$1,799,000
4 Beds ⋅ 4 Baths ⋅ 24195335 MLS
Originally built in 1769, this beautifully renovated and meticulously maintained antique home blends historic character with modern comfort. Set on two landscaped acres along one of Wilton's most scenic country roads, the four-bedroom, three-and-a-half-bath residence offers approximately 3,758 square feet of thoughtfully designed living space. The renovation included updated electrical systems and a whole-house generator that keeps the home running during power outages. An inviting eat-in kitchen opens to a private patio, while the formal dining room, living room with fireplace, hardwood floors, exposed beams, and period details create warmth and character throughout. The primary suite includes a private bath and walk-in closet, and the finished third-floor offers flexible additional space. A charming antique barn and two-car garage complete the property, with room for a pool. Enjoy peaceful country living close to hiking trails, Weir Farm, schools, markets, the post office, and town amenities.

206 Mountain Rd, Wilton
311 Mountain Rd, Wilton
$980,000
4 Beds ⋅ 3 Baths ⋅ 24195727 MLS
Beautifully situated on a spacious corner lot, this exceptional home enjoys the added privacy of a quiet dead-end street as its crossroad. Offering over 3,300 sq. ft of living space, this versatile floor plan provides generous room for today's lifestyle w/ endless possibilities for customization. The bright & inviting main level features a spacious living room, dining area, updated kitchen w/ sliders to deck, and an expansive family room perfect for gatherings & entertaining leading to patio. The oversized laundry room offers excellent potential for custom built-in cabinetry, a folding station, mudroom organization, or additional storage. Upstairs, the impressive primary bedroom is a true retreat, complete w/ a walk-in closet & abundant space to create the luxurious primary suite you've always wanted. With room to add a full en-suite bathroom, the possibilities are endless for transforming this space. The additional bedrooms are generously sized, while the large bonus/recreation room provides incredible flexibility. Complete w/ full bathroom & set apart from the other bedrooms, this space could easily serve as: an au pair suite, multi-generational living space/office/gym or playroom. Outdoor living is equally impressive with both a spacious patio and deck, offering multiple areas to relax, entertain, and enjoy the beautiful surroundings. Great opportunity to own a home w/ outstanding sq footage, flexible living spaces, & a peaceful location combining privacy w/ convenience.

311 Mountain Rd, Wilton
8 Indian Rock Pl, Wilton
$1,490,000
4 Beds ⋅ 4 Baths ⋅ 24195404 MLS
Nestled on a quiet cul-de-sac, this beautifully expanded center hall Colonial offers timeless architecture, exceptional craftsmanship, and an open floor plan designed for today's lifestyle. At the heart of the home is a chef's kitchen where soaring vaulted ceilings and exposed beams create an extraordinary sense of space. The expansive eat-in kitchen flows seamlessly into the equally impressive family room, making it the ideal setting for everyday living and effortless entertaining. Designed for the serious cook, the kitchen is appointed with Viking; double ovens, warming drawer, cooktop, and a Sub-Zero refrigerator, generous center island, custom cabinetry, and abundant workspace. French doors from both the kitchen and family room open to the deck overlooking the private backyard, creating an easy indoor-outdoor connection. Formal living and dining rooms provide elegant gathering spaces. Upstairs, the primary suite offers a full bath and fireplace. Three additional bedrooms are generously sized and share a well-appointed full bath. The walk-out lower level offers exceptional flexibility with a full bath and entrance through the under-house garage, making it ideal for an au pair, in-law suite, guest quarters, home office, gym, or recreation space. Beautiful stone walls, and mature landscaping, surround the home in this sought-after location conveniently just minutes from schools, shopping, commuting routes, and all the Fairfield County has to offer.

8 Indian Rock Pl, 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
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

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