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$3,610,000
5 Beds ⋅ 11 Baths ⋅ 24178405 MLS
Welcome to 16 Middlebrook Lane, a stunning custom-built Colonial in one of Wilton's most desirable cul-de-sac neighborhoods. Set on more than four park-like acres and surrounded by conservation land, this exceptional home offers elegance, craftsmanship, privacy, and comfort. A dramatic main hall creates an immediate sense of arrival with a sweeping staircase and refined architectural details. The chef's kitchen features two large islands, honed marble countertops, high-end appliances, generous storage, and French doors to the rear patio. The kitchen opens to an inviting dining and living area with a wood-burning fireplace, while the formal dining room offers coffered ceilings and an adjoining butler's pantry/bar. Oversized windows fill the formal living room with natural light, complemented by a fireplace and bar, and flowing into a custom office with built-ins and its own fireplace. Upstairs, the extraordinary primary suite lives like a private residence with a sitting room, coffee bar, private balcony, generous walk-in closets, and spa-like bath with soaking tub and steam shower. A private staircase leads to the third floor with half bath, ideal for an office, studio, or retreat. Four additional en-suite bedrooms, laundry, and a bonus room complete the second floor. The finished lower level offers recreation space, gym, game room, and full bath. An elevator serving all four levels adds rare ease and flexibility.

16 Middlebrook Ln, Wilton
$3,540,000
5 Beds ⋅ 7 Baths ⋅ 24161566 MLS
Once in a lifetime, a home of this caliber becomes available. Sited on a cul-de-sac in a coveted neighborhood close to town, this exceptional residence pairs custom design with luxurious indoor-outdoor living areas enhanced with smart technology and supported by upgraded mechanicals. A gracious front-to-back foyer showcases elegant living and dining rooms. Everyday living and elevated entertaining are effortless with a new custom kitchen designed by Deane appointed with Simon Pearce pendants, premium appliances, wine frig, and a Zip tap for still and sparkling water. A sun filled eat-in area flows seamlessly into a coffered ceiling family room with fireplace and a covered porch-with flat screen TV, stone fireplace and Bromic heating. A richly paneled office, mudroom and second staircase complete the main level. Upstairs, five bedrooms include a serene primary suite with fireplace and sitting room, a private guest suite and an additional office. The outdoor experience is nothing short of a 5-star resort-with a saltwater Glengate pool, sun shelf, spa and a new outdoor kitchen fully equipped with a built-in grill, pizza oven, Traeger smoker, and refrigeration-all surrounded by stone terraces, lush landscaping, audio system and curated lighting. The lower level boasts a chalet-inspired retreat with recreation, fitness rooms, an infrared sauna, and bedroom suite with a flexible private entry. An exceptional offering for those seeking outstanding craftsmanship and luxury!

12 Brandon Cir, Wilton
$3,385,000
5 Beds ⋅ 9 Baths ⋅ 24131985 MLS
*Featured on 12 News CT* and built by renowned master builder John Heggland, this exceptional 7,811 sq ft Georgian Colonial estate is gracefully sited on 2.45 private acres in one of Wilton's most sought-after, nature-rich locations. Known for his uncompromising craftsmanship and timeless architectural integrity, Heggland delivers a residence that blends classic elegance with the finest in modern luxury and energy-efficient design. Inside, a double-height foyer with a sweeping staircase introduces rich hardwood floors, intricate moldings, and finely paneled walls. Formal living and dining rooms open to an inviting family room centered around a fireplace. The chef's kitchen features custom cabinetry, a butler's pantry, and oversized island. Two private offices with built-ins provide ideal work-from-home flexibility. Upstairs, each ensuite bedroom offers walk-in closets and tranquil sitting areas, while the luxurious primary suite boasts a spa-inspired bath and dressing room. Outside, enjoy resort-style living with a 20x60 pool, pool house, and expansive patios surrounded by manicured grounds. A finished lower level includes a private entrance for an au-pair or in-law suite, media room, or gym. Additional highlights include energy efficient geothermal system, a 3-car garage, and serene wooded privacy-all minutes to top-rated Wilton schools, dining, and commuting routes. Don't miss the video link As Featured on Channel 12 News!

76 Sturges Ridge Rd, Wilton
$3,200,000
5 Beds ⋅ 6 Baths ⋅ 24159919 MLS
At the end of a quiet South Wilton cul-de-sac, this exceptional Colonial pairs timeless architecture with beautifully curated interiors and a private, picturesque setting. From the moment you enter, the quality is unmistakable-exquisite millwork, elegant proportions, and thoughtfully designed spaces create a home that feels both refined and deeply livable. Formal living and family rooms each offer a fireplace, while the banquet-sized dining room is perfectly suited for memorable entertaining. At the heart of the home, a stunning chef's kitchen opens seamlessly to the family room, creating the kind of space where everyone naturally gathers. Custom white inset cabinetry, top-tier stainless steel appliances, quartz countertops, and an oversized island are complemented by a coffered ceiling, stone fireplace, and a warm, inviting atmosphere that balances sophistication with comfort. A private study offers a polished work-from-home setting, while the exceptional mudroom-with extensive built-ins and an additional half bath-brings effortless function to everyday life. Upstairs, five en suite bedrooms and a spacious playroom offer flexibility for modern living. Each bath is beautifully finished with heated floors, and the primary suite is a true retreat, complete with a fireplace, a luxurious spa bath, and an extraordinary custom closet.

21 Lee Allen Ln, Wilton
$2,892,500
4 Beds ⋅ 7 Baths ⋅ 24103432 MLS
A waterfront Shangri-La! Situated on Popes/Streets Pond in picturesque Nod Hill, this detail rich colonial is one of few waterfront homes in all of Wilton. Immerse yourself in nature and privacy as if you're in VT or NH while residing just 50 miles from midtown NYC! Situated on 2.43 acres, this residence offers every feature/amenity one could ask for & w/high-style! Prominent views can be enjoyed from the heated gunite pool, patio, pergola, outdoor kitchen, fire pit or even the Adirondack chairs set among the sprawling green lawn. Sophistication abounds the interior of this home w/contemporary steel doors, a 2 story foyer, splashes of color & grand design throughout. The sunken LR is generous in scale, offers high ceilings, gas fireplace & showcases views straight up the reservoir. A spacious Great Rm hosts a more casual entertaining space, daily eating area, wet bar & a no-expense-spared luxury kitchen suited for gatherings & fine dining. Thru the butlers pantry you arrive in a fully paneled DR w/garden/pool views. The first floor is completed w/step down office, 2 half baths, another pantry & mudroom. The 2nd floor showcases a Primary BR suite fit for a VIP w/indulgent bath & dressing rms. 2 large guest BR's, 2 baths & laundry rm complete this level. Above the garage is a potential in-law space w/family room, BR, full bath & separate entrance! It gets even better; THERE IS A BARN! Imagine all the possibilities! Come see this soulful home and do not miss virtual tour link.

226 Nod Hill Rd, Wilton
$2,825,000
5 Beds ⋅ 7 Baths ⋅ 24161502 MLS
Welcome to 137 Linden Tree, a masterpiece of modern luxury and thoughtful upgrades in the heart of Wilton. This meticulously maintained home blends elegance, functionality, and high-end amenities for an extraordinary living experience. The property's curb appeal is striking, with a circular driveway, manicured lawns, curated plantings, and a full-property irrigation system. In the backyard, a custom Gunite pool with a Jacuzzi, crafted by Glen Gate, anchors a resort-style oasis. Surrounded by lush landscaping, stone patios, and premium outdoor furnishings, the space is perfect for entertaining or unwinding. A poolside bar with an 8-burner grill and refrigeration elevates summer gatherings, while safety features like a child-resistant pool cover and code-compliant fencing ensure peace of mind. Nearby, an enclosed garden with raised beds, drip irrigation, and deer-proof fencing awaits gardening enthusiasts. The inside has been freshly painted and carpeted. The family room offers a cozy WB fireplace with a gas starter, a 76" Samsung TV with surround sound and deck access. A fully equipped lower level adds another entertainment hub. Additional space is available in the walk-up attic. Smart home features abound, from a security system, automated exterior lighting, pool, and a whole-house generator. Nestled in the serene community of Wilton, this property features resort-quality amenities, elegant interiors, and smart conveniences designed for comfortable living.

137 Linden Tree Rd, Wilton
$2,700,000
4 Beds ⋅ 5 Baths ⋅ 24178736 MLS
HIGHEST & BEST OFFERS REQUESTED BY MONDAY, 6/22 AT 10:00 AM. Exquisite Dream Home in South Wilton: A Sanctuary of Elegance and Nature. Nestled at the end of a South Wilton cul-de-sac on an elevated site, this extraordinary home blends luxury with natural beauty. Surrounded by 83 acres of Bradley Park conservation land with hiking trails and a short walk to Wilton Town Center, it offers privacy and convenience. Spanning 5,560 sq ft, this light-filled residence features four spacious bedrooms, ideal for elegant living and entertaining. With 9+ ft ceilings, hardwood floors, two fireplaces, French doors, and deep moldings, the home exudes sophistication. The open layout includes a recreational room, an 800-bottle wine cellar, and a butler's pantry. A fifth or sixth bedroom can be added in the den/office or rec room. Over $400,000 in upgrades elevate this property, including a heated Signature Gunite saltwater pool, a solar panel system with Tesla Powerwall, a Fiero Forni pizza oven, vegetable gardens, a chicken coop, and a slate patio with built-in seating for outdoor dining. Nature enthusiasts will enjoy proximity to Bradley Park, Norwalk River Valley Trail, and vast conservation land. Just minutes from NYC, this home offers luxurious living, privacy, and convenience-a true sanctuary and rare find.

97 Graenest Ridge Rd, Wilton
$2,686,000
5 Beds ⋅ 6 Baths ⋅ 24169514 MLS
Tucked along one of Wilton's most coveted cul-de-sacs, 86 Middlebrook Farm Road is a home that truly belongs to its setting-quiet, prestigious, and effortlessly beautiful. Architecturally designed with intention and a refined eye, this residence balances timeless elegance with modern livability. Spanning 12 thoughtfully curated rooms, including 5 bedrooms, 5 full baths, and a powder room, the home offers both sophistication and comfort in equal measure. The heart of the home is a stunning kitchen, where an oversized marble island, two dishwashers, a walk-in pantry, and seamless flow create the perfect backdrop for daily living and entertaining alike. Each space feels purposeful, inviting, and easy to enjoy. Outdoors, the property transforms into a private, parklike retreat, bordered on one side by the Wilton Land Trust and on the other by 48 acres of the Wilton Riding Club. Flat, manicured grounds offers exceptional privacy and tranquility. The gunite pool serves as a sparkling focal point, paired with a sauna and lush landscaping, creating a true backyard escape. With flexible living options, including potential for a second primary suite, and a location just minutes to Wilton Center, top schools, and commuting routes, this home delivers a lifestyle that is both refined and relaxed.

86 Middlebrook Farm Rd, Wilton
$2,650,000
5 Beds ⋅ 6 Baths ⋅ 24165876 MLS
Sophisticated, timeless, and flawlessly reimagined, this 7,600 sq ft transitional Hamptons-style Colonial-Cape delivers luxury living with effortless ease. Offering 18 beautifully scaled rooms - including 5 spacious bedrooms, 6 full baths, and multiple inviting gathering spaces - this home balances grand entertaining with relaxed everyday comfort. Exquisite millwork, sleek transitional finishes, and four fireplaces create warmth throughout, while sunlit formal rooms flow seamlessly into casual living areas. The chef's kitchen with service galley anchors the home and opens naturally to outdoor spaces. Private retreats, work-from-home areas, and a separate in-law apartment with private entrance enhance the home's versatility. The grounds are exceptional - lush landscaping, fieldstone walls, tiered patios, a resort-style pool with spa and waterfall, a heated pool house, and an elevated firepit patio all offer unmatched outdoor living. Tucked up on a quiet cul-de-sac, this property blends true neighborhood charm with the privacy of its own enclave. A premier location, superb craftsmanship, and every modern amenity - this is refined living at its best. Discover the lifestyle awaiting you ... schedule your private tour today. 7,692 SF TOTAL heated living space, per architect.

10 Woodhill Rd, Wilton
$2,650,000
6 Beds ⋅ 7 Baths ⋅ 24158976 MLS
A rare opportunity to own a custom-designed residence by renowned architect Peter Cadoux, nestled on a private cul-de-sac abutting Quarry Head Park/Harrison Smith Preserve providing direct access to nearly 60 acres of hiking and equestrian trails. Additional privacy is provided by a serene sanctuary of forever green space to the west. This extraordinary home combines architectural artistry, thoughtful design, and the finest materials and craftsmanship. The home has been meticulously maintained by a professional property manager. A grand foyer with 20+ ft ceilings, welcomes guests into an atmosphere of understated elegance, framed by exceptional millwork. The main living spaces flow gracefully: a formal dining room adorned with a crystal chandelier and an inviting living room featuring a coffered ceiling and fireplace. A half bath for guests and a private office with built-in wood cabinetry is off to the right. Off the dining room, the butler's pantry featuring a refrigerator and wine cooler make entertaining a breeze. The kitchen is a culinary dream, appointed with Viking and Sub-Zero appliances, double sinks, beautiful quartz countertops and gorgeous custom cabinetry. With ease for entertainment, the kitchen opens to the family room with a well-appointed stone fireplace. Mirroring this focal point, an outdoor fireplace anchors the wrap-around deck, offering seamless indoor-outdoor entertaining.

55 Tanners Dr, Wilton
$2,650,000
5 Beds ⋅ 6 Baths ⋅ 24150931 MLS
Offer Deadline 5pm, Feb 2nd. South Wilton Showstopper! Nestled at the end of desirable cul-de-sac, this pristine, turnkey Colonial offers an ideal floor plan for today's lifestyle w/4,500 sq ft plus finished walk-out lower level. Exquisite millwork, 9' ceilings, and hardwood floors flow throughout the home. The custom-designed kitchen is a chef's dream, featuring high-end appliances including built-in espresso maker, oversized island, spacious pantry, and stunning cabinetry-all open to a comfortable family room w/floor-to-ceiling stone fireplace. A private home office/study adds functional flexibility. Gracious living room w/ gas fireplace and large formal dining room are sure to impress. Upstairs, the luxurious primary suite includes a gas fireplace, spa-like bath, and huge walk-in closet. Three add'l bedrooms offer ensuite or Jack-and-Jill baths and walk-in closets. A recreation room w/custom built-in desks and shelving provides ideal space for work or play. The second-floor laundry room boasts gorgeous cabinetry and sink for added convenience. The finished walk-out lower level features a fireplace, full bath, and guest bedroom. Outdoor living shines w/ a welcoming front porch, beautiful in-ground pool, fabulous patio with built in Lynx grill and fire pit. Professionally landscaped w/ perennial gardens thru out. This exceptional home combines elegance, functionality, ideal NYC commute and is minutes to town and schools. Meticulous and tasteful! Not to be missed! See addend

51 Chessor Ln, Wilton
$2,630,000
5 Beds ⋅ 6 Baths ⋅ 24151937 MLS
Please submit HIGHEST and BEST offers by 3pm Tuesday March 10th. Set in a highly sought after south Wilton,CT cul de sac, this light-filled home offers refined design and effortless indoor-outdoor living. Rebuilt in 1999 and thoughtfully renovated in 2009, the open layout feels both expansive and welcoming. From the moment you enter, front-to-back and side-to-side sightlines, soaring ceilings, and oversized windows create an airy, elegant first impression. The gracious living room features custom millwork, a striking stone fireplace, dining area, and upper dormer windows that add architectural detail and natural light. The open kitchen with recent upgrades is designed for both daily living and entertaining, showcasing high-end appliances, custom cabinetry, and a walk-in pantry. A sun-filled breakfast room with built-ins and a wall of windows overlooks the beautifully landscaped, level backyard and in-ground gunite pool, offering a seamless connection to outdoor living. Multiple gathering spaces include a cozy family room with built-ins and stone fireplace, a flex space or recreation room, and a large second-floor bonus room. The first-floor primary suite provides privacy and convenience with 2 walk-in closets and a pristine full bath. A 5th bedroom,full bath off the bonus room is perfect for guests or extended living needs. Bluestone patios, private and level backyard, lighted basketball court, room for volleyball, soccer and more.

9 Old Farm Rd, Wilton
$2,625,000
5 Beds ⋅ 6 Baths ⋅ 24168347 MLS
A rare offering in sought-after South Wilton, this exceptional 2009 Colonial pairs over 5,800 square feet of sophisticated living space with the feel of a private retreat. Surrounded by 1.8 acres of park-like grounds, the property offers a serene, resort-like setting just minutes from Rolling Hills Country Club, Ambler Farm, and major commuter routes. Designed for both elegant entertaining and effortless daily living, the home features 5 bedrooms and 6 baths, including a flexible main-level suite ideal for guests or a private office. Sun-filled living spaces include a gracious sitting room, living room, and sunroom, while two fireplaces bring warmth and character throughout. The kitchen is perfectly positioned to overlook the pool and backyard, with sliding doors opening to the deck and outdoor entertaining spaces for seamless indoor-outdoor living. Upstairs, a spacious great room provides ideal flex space for media, play, or gathering, while the expansive primary suite offers walk-in closets and a spacious bath. A second-floor laundry room, walk-up unfinished attic, and finished lower level add versatility and convenience. Outside, the lifestyle is truly exceptional. A saltwater pool, hot tub, expansive deck, level lawn, and indoor/outdoor sound system create the feel of a private oasis-peaceful, polished, and perfectly suited for both quiet enjoyment and entertaining. Offering a rare blend of space, style, and serenity, this home is a true gem. Equipped with an electric

12 Langner Ln, Wilton
$2,600,000
4 Beds ⋅ 3 Baths ⋅ 24170670 MLS
Elegant and impeccably appointed, this exceptional top-shelf residence offers refined living in the heart of the village's historic district. You will find this Architectural Gem has been masterfully reimagined for modern living while honoring its rich provenance. Rob Sanders Architects, renowned for historic restorations transformed this residence into a timeless, sophisticated masterpiece showcasing perfectly scaled living spaces. Inside, exquisite craftsmanship is evident throughout-from custom cabinetry and millwork to bespoke lighting and curated finishes. Wide-plank chestnut floors, and authentic 6-over-6 windows provide warmth and character, blending historic charm with elevated, modern comfort.Highlights include an exceptional Chef's KIT that has every high-end detail imaginable, stunning Sunroom, handsome Library w/wet bar, fabulous Scullery, beautiful Living & Dining Rms, luxurious Primary Suite w/Spa inspired Bath, comfortable Home Office. Set on 1.95 picturesque acres of lush lawns, mature gardens, expansive patios and classic stone walls, the property also includes a classic New England barn and enjoys a premier in-town location with easy access to the village center with wonderful restaurants, cafes, gourmet market and wonderful array of shops. Close proximity to train, schools, and parks as well as Downtown New Canaan and Ridgefield..Approx 1 Hour to NYC. Sophistication at every turn. Impossible to Reproduce!

65 Ridgefield Rd, Wilton
$2,552,000
6 Beds ⋅ 6 Baths ⋅ 24185788 MLS
Built by the renowned Kellogg Brothers, this exceptional custom home showcases timeless craftsmanship, architectural elegance, and meticulous attention to detail. A circular driveway leads to a dramatic two-story foyer with Bordeaux-style Brazilian cherry parquet flooring. The gourmet kitchen is appointed with a Sub-Zero refrigerator, Viking six-burner range with griddle, pot filler, warming drawer, two dishwashers, custom cabinetry, walk-in pantry, and sliders opening to the expansive deck. The spectacular great room features soaring ceilings, a fireplace, dramatic two-story windows, extensive custom millwork, refinished hardwood floors, a brass chandelier, and sliders that seamlessly connect to the outdoor living spaces. Additional highlights include a sun-filled living room with fireplace and bow window, elegant dining room with window seat, and a richly paneled office with French doors and access to the screened porch. Outside, enjoy a heated infinity-edge Gunite pool, grotto seating area, mature landscaping, and manicured privet hedges creating an exceptional private oasis. The property also offers direct access to scenic walking trails connecting to 93-acres of the Wilton Land Trust and Harris Smith Preserve. The home offers six bedrooms, including five upstairs and one on the walk-out lower level. The finished lower level features a recreation room with a wood-burning fireplace. Grey Rocks truly depicts luxury, comfort, and timeless design.

88 Grey Rocks Rd, Wilton
$2,550,000
5 Beds ⋅ 6 Baths ⋅ 24163135 MLS
Welcome to this exceptional home set on a quiet cul-de-sac in one of Wilton's most sought-after neighborhoods. Offering 5 spacious bedrooms, 5 full baths &1 half bath, this home seamlessly blends timeless elegance with modern comfort. The sun-drenched interiors highlighted by gorgeous windows fill the space with natural light including new windows in the semi circle area. Extensive high-gloss millwork & striking coffered ceilings showcase the home's craftsmanship and refined architectural detail throughout. The thoughtfully designed floor plan is ideal for both everyday living & entertaining, featuring a gourmet kitchen w/high-end appliances, custom cabinetry, & center island. A stylish butler's pantry add both function & sophistication, making hosting effortless. The kitchen flows seamlessly into gracious living and dining spaces designed for gathering.Upstairs, the luxurious primary suite serves as a private retreat, complete w/a spa-like bathroom & generous walk-in closets. Each additional bedroom is well-proportioned w/access to beautifully appointed full baths, offering comfort & privacy for family & guests alike.The LL offers flexible living spaces perfect for a home office, gym, or media room w/a stone fireplace & full bath. Outside, a beautiful approach highlights the professionally landscaped grounds designed by Glen Gate, creating a picturesque setting. The level, walk-out expansive patio provides an ideal backyard backdrop for outdoor entertaining or relaxation!

18 Brandon Cir, Wilton
$2,454,000
6 Beds ⋅ 6 Baths ⋅ 24167275 MLS
Tucked at the end of a cul-de-sac in one of Wilton's most convenient locations, 8 Maplewood Lane is designed for the way you want to live-easy, active, and connected to nature. With 5-6 bedrooms, a backyard pool, and a rare rear border on a protected nature preserve, this home offers something that's hard to find: lasting privacy with a true "no neighbors behind you" setting. Start your mornings with coffee and birdsong, knowing the view beyond your yard will remain untouched. Spend afternoons poolside, grilling, entertaining, or unwinding after a busy day-this is a property that makes it simple to enjoy summer at home. When the seasons change, the preserve backdrop adds year-round beauty, from fresh spring greens to crisp fall color. Inside, the generous bedroom count creates flexibility for a variety of needs-guest space, work-from-home options, a hobby room, or a dedicated play or fitness area-while still keeping everyone comfortable. And when it's time to head out, you're perfectly placed close to Wilton schools, town amenities, and Rolling Hills Country Club, making everyday errands, activities, and meetups feel effortless. If you've been looking for a home that blends neighborhood convenience, outdoor lifestyle, and enduring privacy, 8 Maplewood Lane is one you'll want to experience in person. 2.75% assumable mortgage until 2028 and 40K credit at closing toward a new roof.

8 Maplewood Ln, Wilton
$2,395,000
5 Beds ⋅ 7 Baths ⋅ 24118097 MLS
This stately 5 BR shingle style colonial with over 7000 sf in favored Sturges Ridge neighborhood is a memory-making treasure! With a level backyard that plays host to games, gardens and gatherings including a lobster bake, birthday parties with water slides, badminton, croquet, the view to witness joyful connection is endless. The home is a haven of warmth and sophistication, and offers large spaces for big groups and special smaller rooms for cozy togetherness. Have a crowd help you prepare a meal in the kitchen while the game is on in the handsome Family Room with rich coffered ceiling, stone fireplace and fully outfitted wet bar. The newly remodeled lower level entertainment center has a deluxe kitchenette with stone backsplash and quartzite countertop, dishwasher, fridge and sink, as well as plenty of storage in one of the cleanest basements you'll ever see. Large Primary BR Suite includes a gas fireplace, walk-in closet, full bath with double vanities and separate tub. All bedrooms are spacious with adjacent or ensuite bath, and the bonus room off back stairs can be anything you want: playroom, music room, dance studio-use your imagination! A special feature is the 3rd floor office with available business grade router and hard wired data/internet. Quiet, peaceful and a true getaway for focused working (and sometimes a little putting practice). These owners have been meticulous about maintaining their beloved house. The care is apparent, as is their true joy in living her

185 Sturges Ridge Rd, Wilton
$2,335,000
5 Beds ⋅ 7 Baths ⋅ 24083683 MLS
Nestled in Wilton's most prestigious enclave, the home offers nearly 3 acrs of breathtaking beauty& privacy. Tree-lined drive winds along tranquil Comstock Brook, leading to the distinguished residence. Mature cherry, apple, maple, blue spruce, and pine trees enhance the idyllic setting, while an expansive stone terrace invites al fresco dining & offers potential for future pool. Designed by architect Dipti Shah of Paul Benowitz Architects, it seamlessly integrates w/its surroundings. Soaring 2-story foyer w/floor-to-ceiling glass welcomes guests, leading to a sunlit living rm w/a grand stone fireplace. The richly appointed library, formal dining rm, & gourmet kitchen-featuring professional-grade appliances & breakfast nook-flow effortlessly into the family room & terrace for ideal indoor-outdoor living. Addtl highlights incl a rear staircase, 2 powder rooms, mudroom, & radiant-heated 3-car garage. The luxurious master wing features water views, fireplace, pvt sitting room/office, & walk-in closets. 4 addtl bedrooms, 4 full baths, & spacious laundry rm complete the upper level. A finished third floor offers space for a playroom,gym or rec area, while lower level, w/high ceilings & exterior access, is ideal for a gym or media lounge.Blending architectural splendor with natural serenity, this rare offering ensures an unparalleled lifestyle of elegance & comfort. Top schools, charming village, great dining, YMCA, easy access to trains, major highways, & amenities

33 Middlebrook Farm Rd, Wilton
$2,300,000
4 Beds ⋅ 5 Baths ⋅ 24181450 MLS
Set on a beautifully landscaped, level property in South Wilton, 18 West Meadow offers exceptional indoor and outdoor living with convenient access to Westport, Norwalk, I-95, the Merritt Parkway, shopping, dining, and train service. This 4-5 bedroom home features a renovated kitchen with Absolute Black granite countertops, a large center island, breakfast area, Wolf cooktop and wall ovens, and a Sub-Zero refrigerator. The kitchen opens to the family room with custom built-ins, a wood-burning fireplace, and sliding doors to the stone patio. Sliders from both the family room and dining room create a seamless connection to outdoor living spaces. The main level also includes an office with a bay window, built-in bookshelves, gas fireplace, and backyard views. A formal living room features additional built-ins and a gas fireplace, while a large pantry provides ample storage. Upstairs, the primary suite includes a windowed walk-in closet, Juliet balcony overlooking the backyard, and a renovated, bath with soaking tub, walk-in shower, dual vanities, and private water closet, all with Porcelainosa fixtures. Three additional bedrooms are located on the upper level, including two with en-suite baths. A walk-up attic offers future expansion potential. Above the garage is a flexible living area with a bedroom, full bath, and separate access through the mudroom. The backyard features a stone patio, irrigation system, fenced vegetable garden, expansive lawn, and a whole house generator.

18 W Meadow Rd, Wilton
$2,260,000
4 Beds ⋅ 5 Baths ⋅ 24120730 MLS
Outstanding, updated, modern Colonial tucked into one of Wilton's most sought-after neighborhoods-just a short stroll to town. Offering 4/5 bedrooms, 3 full baths, and 2 half baths, this home seamlessly blends timeless style with thoughtful updates for today's lifestyle. Step inside to discover beautifully renovated kitchen and baths, sun-filled living spaces, and the comfort of geothermal heating and cooling. A whole-house generator provides peace of mind, while the open layout invites both everyday living and effortless entertaining. The back patio with built in grill and smoker as well as a gas fireplace is perfect for summer/fall evenings with friends and family. The beautiful gardens designed and cared for by a master gardener are a living work of art. Lush, colorful, and inviting in every season. This rare combination of walk-to-town convenience, modern updates, and stunning gardens makes 81 Graenest Ridge Road a true gem in Wilton. Please submit "Highest and Best" Offers by Tuesday 9/16 at noon.

81 Graenest Ridge Rd, Wilton
$2,250,000
5 Beds ⋅ 3 Baths ⋅ 24167923 MLS
Some homes simply check boxes. This one redefines what life in Fairfield County can look like. Set on a coveted cul-de-sac in the heart of Wilton, this fully updated 5-bedroom retreat offers a rare blend of privacy, beauty, and convenience-just minutes to top-rated schools, Wilton Center, and the charming downtowns of Ridgefield and New Canaan. It's the way this home makes you feel that sets it apart. Step outside and exhale. Open skies, mature trees, and birdsong create a setting that feels worlds away, with the Wilton Riding Club, its summer camp, pool, tennis, paddle courts and miles of nature trails nearby. The expansive, usable property invites both relaxation and possibility, with room for a future pool, barn, or accessory dwelling unit (ADU). Designed for effortless living and entertaining, the outdoor spaces shine-from the expansive back deck at sunset to lawn games on the open grounds, to long dinners with friends on the screened-in porch. Unwind year-round in the barrel sauna, your own private wellness escape. A newly built fenced garden with raised beds awaits your vision-whether heirloom vegetables, fresh herbs, or cutting flowers. Inside, thoughtfully updated and carefully curated interiors deliver turnkey ease with timeless appeal. This is Wilton living at its most idyllic: natural, connected, and ready for what comes next.

25 English Dr, Wilton
$2,250,000
6 Beds ⋅ 5 Baths ⋅ 24145307 MLS
This historic 1800s Colonial at 88 Drum Hill has been thoughtfully expanded and renovated, blending timeless charm with modern luxury. Original features - wide plank floors, multiple fireplaces, high ceilings, and classic moldings - honor the home's heritage, while updates create a fully livable, elegant residence. With 6 bedrooms, 4 full baths, and 1 half bath, this updated historic home offers flexible spaces for entertaining, work-from-home setups, and family gatherings. Set on a beautifully landscaped 2-acre property, the home features a stunning in-ground pool, outdoor entertaining areas, and private spaces perfect for relaxation. Unique historic touches, including a sleeping porch, library/study, and charming updated kitchen accents, blend seamlessly with modern comforts, including a chef's kitchen and light-filled living and dining areas. Ideally located minutes from Wilton Center and top schools, this luxury Wilton CT home combines historic integrity, modern updates, and a lifestyle designed for year-round enjoyment - a rare opportunity in Wilton real estate. Offer deadline: All offers must be submitted by Sunday, the 25th, at 4:00 PM.

88 Drum Hill Rd, Wilton
$2,220,000
5 Beds ⋅ 4 Baths ⋅ 24124533 MLS
Set high atop a ridge in one of Wilton's most desirable neighborhoods, offering STUNNING views of expansive landscape from nearly every room as well as its wraparound porch, this magnificent, 5/6 BR farmhouse Colonial is a charming yet sophisticated home for all 4 seasons. Front entrance boasts a 2-story foyer w/custom bookcases. Gorgeous living room offers a floor-to-ceiling fieldstone fireplace, wraparound bookcases, and a large bay window w/inviting window seat. French doors lead to a large, gourmet eat-in-kitchen w/new pantry & wine bar, as well as access to the lovely stone patio. Adjacent handsome den/library, w/patio & front porch access, offers custom built-ins & french doors. Host memorable dinner parties from the gracious dining room w/elegant pocket doors & swaying vista. Upstairs primary bedroom suite is complete w/vaulted ceiling, walk-in closets, & primary bath. Other upstairs highlights include 4 bedrooms, office/BR with vaulted ceiling, 2 full baths and a fabulous family room with large closets. The home's exterior is truly a private oasis, perfect for entertaining. The park-like manicured property to the rear of the home offers a renovated stone patio, magnificent gunite pool, lovely plantings, generous lawn space, & new outdoor shower. To the front, enjoy a private front-row seat to spectacular Wilton town fireworks, vibrant foliage & one of the best sledding hills in the area. Convenient & serene property is a rare find. See supplements for updates. A GEM!

87 Catalpa Rd, Wilton
$2,206,020
6 Beds ⋅ 5 Baths ⋅ 24089948 MLS
New Listing! Originally built in 1825, this distinguished Colonial Revival estate was significantly expanded in the 1920s by McCall's Magazine, which transformed it into their elegant country retreat. Now offering over 5,600 square feet of beautifully remodeled living space, the home has been thoughtfully restored to honor its historic roots while offering every modern comfort. A true sanctuary from the pace of everyday life, this property invites you to vacation at home. Enjoy morning coffee on the private master terrace, sunbathe on the south terrace, or relax with a book on the charming porch. The expansive, level grounds are ideal for outdoor living and feature a sun-drenched site perfect for a future pool. Inside, the home balances grandeur with warmth. The stunning Carrara marble kitchen is a chef's dream, equipped with high-end appliances and a spacious island for gathering. A full butler's pantry and porch provide the perfect setup for entertaining. Host unforgettable dinners in the banquet-sized dining room or dine al fresco on the breathtaking stone terrace. The generous living room and adjacent den/bar feature three fireplaces and multiple sets of glass doors that open to the terrace and porch, blending indoor and outdoor living seamlessly. Work from home in one of two quiet offices, then unwind in the cozy family room by the fire, enjoy a workout in your personal gym, or retreat to the luxurious primary suite.

89 Chestnut Hill Rd, Wilton
$2,200,000
4 Beds ⋅ 3 Baths ⋅ 24173830 MLS
Highest and best by 2:00 pm on Monday, 5/18. Set on a coveted lower Nod Hill cul-de-sac, 45 Ryders Lane is the kind of home that quietly wins people over the moment they arrive. Classic in style yet thoughtfully updated for modern living, this 4-bedroom Colonial blends timeless architecture with warm, inviting spaces designed for real life. Inside, light pours through generously sized rooms, creating an easy elegance throughout the home. The renovated kitchen is both beautiful and functional, featuring a Wolf range, Sub-Zero refrigerator, and seamless flow into the home's casual gathering spaces. Nearby, the mudroom and updated laundry area make everyday living refreshingly effortless. Upstairs, the primary suite feels like a private retreat, complete with a beautifully renovated bath featuring radiant heated floors and a heated towel bar. Three additional spacious bedrooms, an updated hall bath, and a walk-up attic provide flexibility for today's lifestyle. Outside, summer practically writes its own plans. A charming screened porch overlooks the property, while the stone patio and expansive yard offer room for entertaining, gardening, or simply slowing down for the evening. Thoughtful improvements, including a new cedar roof, solar panels, upgraded electrical service, an invisible fence, and a new water heater, add comfort and peace of mind. A special home in one of Wilton's most sought-after neighborhoods.

45 Ryders Ln, Wilton
$2,200,000
5 Beds ⋅ 5 Baths ⋅ 24170851 MLS
BEST & FINAL by Monday, May 4th at 12:00PM. Tucked within a charming private enclave in Wilton, this architect-designed retreat by Rob Sanders offers a welcome sense of calm, privacy, and everyday escape. Set on two beautifully manicured acres, the home feels like a personal sanctuary, where light pours through oversized windows and natural scenery becomes part of every room. Thoughtfully designed for relaxation, entertaining and connection, the open living spaces flow effortlessly, anchored by a chef's kitchen with Wolf, SubZero, and Miele appliances, custom cabinetry, and a soaring cathedral ceiling. Whether hosting or unwinding, the atmosphere is warm, airy, and serene. Five spacious bedrooms - including three en suites, offer comfort and flexibility, while four fireplaces add cozy ambiance throughout. The primary suite is a true escape, featuring a private sitting room, custom walk-in closet, and a tranquil bath with radiant heat, soaking tub, and separate shower. A separate-entry en suite is ideal for a guest suite or a private office with a panoramic wooded view. Outdoors, the experience continues: bluestone patio, fire pit, gated vegetable garden, outdoor shower and expansive meandering lawn create a magical setting, while a clubhouse, playscape, and zip line ensure endless fun in a safe, secluded environment. Enjoy access to Wilton's top-rated schools, nearby towns, and Metro-North-offering seamless access to NYC while preserving the peace of your own private retreat

51 Black Alder Ln, Wilton
$2,176,300
4 Beds ⋅ 4 Baths ⋅ 24168973 MLS
HIGHEST and BEST DUE TUESDAY at 5 pm First time ever on market. This light-filled colonial sits high on a prime lot with views on beautiful Keelers Ridge. Custom-built by Kellogg Brothers, this home has 3 fireplaces and exceptional craftsmanship throughout. The property is open, sunny, and features a beautiful pool, outdoor living area, and expansive lawns. The expanded eat-in-kitchen has two islands, a 48" Thermadore gas range, double wall ovens,, and more cabinets than you will need. The kitchen is open to family room with fireplace and a sunroom with cathedral ceiling that opens to outdoor living area. The living room is comfortable, yet has a timeless elegance with fireplace, built-ins, beautiful windows and also opens to outdoor oasis. The dining room has floor to ceiling windows and a beautiful built-in. There is a paneled, tucked-away office with a new full bath and a rec room over the garage, in addition to a sunroom with new full bath convenient to the pool. Upstairs is a luxurious primary suite with spa bath, fireplace, and walk-in closet to relax in at the end of a long day. There are 3 more spacious bedrooms and an extra large hall bath. The lower level has 1500 sq ft that is easily finished. This elegant, comfortable home with a special backyard oasis is located close to Quarry Head Park with scenic hiking trails and a neighborhood great for walking, biking, running, and socializing. This home has it all. You will love living here!

45 Keelers Ridge Rd, Wilton
$2,151,000
4 Beds ⋅ 4 Baths ⋅ 24156750 MLS
Set atop a hill on one of Nod Hill's most coveted cul-de-sacs, this home is an elegant Connecticut estate that seamlessly blends classic architecture with refined, modern living. Some say the house has a Southern charm, others see it as a quintessential New England residence, but all agree that it is a sanctuary of hospitality and grace. Features include updated kitchen and baths, a cozy office with fireplace and built-ins, large family room, screened porch, bonus/playroom off the kitchen, and a sunlit garden room adjacent to the brick patio overlooking the level property. Primary BR suite includes full bath, walk-in closet, sitting room and deck. Additional three BR's on 2nd floor (one with brand new deck) and two additional updated baths. Walk your dog with the neighbors, visit nearby Weir Farm for a hike or art-inspiration, enjoy the legendary Nod Hill 4th of July Parade. Just 8 minutes from town and Wilton's award winning schools,18 minutes to SoNo train, 13 minutes to Ridgefield and 4 min to the Wilton Riding Club. Majestic and unique, this is one home you don't want to miss.

34 Ryders Ln, Wilton
$2,150,000
4 Beds ⋅ 5 Baths ⋅ 24142765 MLS
New Construction, just started this Farmhouse/Colonial with 4800 square feet. This Open Floor plan offer a two-story entry Foyer with a formal Dining Room and Living Room on either side. A modern open Kitchen with center island and informal dining area that flows into the Family Room with gas fireplace. Upstairs, the Primary Bedroom suite is generous, complete with a luxurious Closet space and an elegant Bath. Three additional Bedrooms two full Baths and a convenient second floor Laundry Room. extra space available on the third floor and walk-out basement, all this on 2 acres convenient location close to Town center and Train.

109 Signal Hill Rd, Wilton

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