Homes for Sale near Wilton High School

Beautifully situated within the coveted Silver Spring community on the former Firestone estate thoroughbred racetrack, this sophisticated Colonial offers modern luxury and prime location on a private road. Great curb appeal and lush landscaping welcome you to this updated, meticulous move-in ready home adorned with custom millwork, gleaming hardwood floors and functional flow. Dreamy NEW white

Dianne DeWitt Berkshire Hathaway NE Prop.

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

Indira Desai Christie William Pitt Sotheby's Int'l

This stunning fully renovated 5-bedroom, 4 full bath home offers the perfect blend of modern design and comfortable living, set on a private 2.03-acre lot. Featuring an open concept layout with 9-foot ceilings, gleaming hardwood floors, central air, and fresh paint throughout, the home is both stylish and move-in ready. The inviting living room with a cozy fireplace flows seamlessly into the

Lynne Murphy Berkshire Hathaway NE Prop.

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,

Joe Scozzafava William Raveis Real Estate

Offering approximately 6,400 square feet of finished living space across three thoughtfully designed levels, this exceptional residence blends timeless architecture with modern luxury. Expansive interiors are filled with natural light and feature refined craftsmanship, generous room proportions, and a seamless flow ideal for both everyday living and elegant entertaining. The finished lower level

Hernan Benitez VORO CT LLC

20 Cherry Lane is a rare Georgian Colonial estate set on nearly 2.5 flat, manicured acres bordering 50 acres of protected conservation land and hiking trails. Offering over 9,000 sq ft, this home combines exceptional scale, modern updates, and long-term value. Designed for entertaining and everyday living, the renovated chef's kitchen features double marble islands, double ovens, dual

Molly Rubins NestSeekers International

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,

Sharon Brameier Berkshire Hathaway NE Prop.

Situated on a cul-de-sac and over an acre of flat land in prime South Wilton, this exceptional colonial blends timeless New England charm w/ today's most sought-after amenities. Thoughtfully upgraded, this home offers 4 spacious bedrooms, 5 well appointed bathrooms, abundance of living space, & a layout ideal for everyday living & entertaining. At the heart of the home is a fully updated kitchen

Chris Carozza RE/MAX Right Choice

Tucked away on 2.18 private acres, this beautifully designed 5-bedroom, 6-bathroom home offers exceptional space, natural light, and a layout ideal for both everyday living and entertaining. Discover hardwood floors and a thoughtfully designed main level. The open kitchen flows seamlessly into the family room, anchored by a fireplace that creates a warm gathering space. A sun-filled den with a

Mayra Cardenas Mayorga Berkshire Hathaway NE Prop.

Village Walk, Wilton's most-popular in-town/ pet-friendly community features a magnificent private pool (opens May 22) & meticulously manicured grounds in a park-like setting. This second floor townhouse style home (3-levels) has 2 Bedrooms & 2 Full Bathrooms. The spacious main level features a large open living & dining area, kitchen, first-floor bedroom & full bathroom perfect as a home office

Christopher Sinatra Higgins Group Real Estate

Handsomely set on two private, resort-like acres, this timeless Nantucket-style residence offers the feel of a secluded family compound. Adjacent to a 21-acre wildlife preserve along the west bank of the Saugatuck River, the setting invites fishing by the river and peaceful walks along scenic trails through the surrounding natural landscape. Custom built by celebrated architect Tim Geitz, the

Michelle Genovesi William Raveis Real Estate

Located close to the Lake Club on a private secluded lot bordering Parting Brook. This home underwent a complete top to bottom remodel featuring, a stunning new kitchen, all new windows, heating and cooling system, new baths, siding, deck, etc.... 4 fireplaces, 2 car garage, walk in closet

Peter Hastings Hastings Real Estate

Looking for a diamond in the rough? Located on a rear lot at the end of a cul-de-sac. This property offers the perfect opportunity to create your dream home in South Wilton. Bring your imagination and your builder to make it your own! Well pump not functioning. Furnace is less than 10 years old. House will be sold Strictly As-Is ; Where Is. Seller will NOT be able to empty the majority of the

Ashley Petrides William Raveis Real Estate

Enoch Gilbert House c.1825. A rare opportunity to own a piece of Connecticut history officially listed on the State Register of Historic Places. Known as Frog Hollow, this 2.14-acre estate borders the 60-acre Weir Farm National Historical Park, offering a lifestyle of unrivaled privacy and artistic heritage. The residence was restructured in the 1940s by the renowned duo of F. Nelson Breed and

Melissa Engel Douglas Elliman of Connecticut

Ground-level condominium offering an open studio layout with hardwood flooring and an updated bathroom. The large sliding glass door opens to a private patio, bringing in natural light and extending the living space outdoors. A generous double closet area provides flexibility and can be used as a bedroom space or home office. Residents of Wilton Crest enjoy a variety of amenities, including a

Kris Lippi Get Listed Realty

Set on over two private acres along the Wilton/Weston border, this architecturally distinct Contemporary offers a compelling blend of design, privacy & setting. Ideally positioned in southern Wilton, the home offers rare convenience-just minutes to Wilton Center, Weston, Westport & Georgetown. A circular drive leads to the home, where striking vertical siding and thoughtfully designed grounds

Matthew Nuzie RE/MAX Right Choice

3800 SF of total living space to enjoy! Expansive, four bedroom, four full bath home offers freshly painted rooms, polished hardwood floors and amazing storage, all ideally sited on popular Pipers Hill. The truly flexible floor plan encompasses 3.5 levels including a full, walk-out lower level and bonus den/family room above the two car garage. The formal living and dining rooms both boast bay

Patricia Prenderville Higgins Group Real Estate

Classic Colonial Split with beautiful water views of Horseshoe Pond, ideally set in the heart of Wilton with the rare convenience of walking to town. Enjoy privacy and charm on a beautifully landscaped, fenced-in backyard, while being just moments from the NRVT, shopping, transportation, and major roadways. Sun-filled and thoughtfully designed, the main level offers an easy flow for everyday

Lynne Murphy Berkshire Hathaway NE Prop.

Stunning Sun-Filled Colonial with Designer Barn. Set on 1.32 flat acres on the New Canaan border, this bright 4-bedroom Colonial offers over 4,000 square feet of sophisticated living space. Built in 1990, the home perfectly captures "old world" architectural charm-featuring reclaimed beams & timeless New England character-while offering the ease & peace of mind of modern construction. The main

Casey Lange Compass Connecticut, LLC

Welcome to this beautifully updated split-level home in the highly desirable town of Wilton Thoughtfully renovated, this 3 bedroom, 3 full bath home offers a seamless blend of modern style and everyday comfort. The open-concept main level is filled with natural light and designed for today's lifestyle, connecting the living, dining, and kitchen areas with ease. The kitchen features quartz

Lynne Murphy Berkshire Hathaway NE Prop.

Tucked at the end of a private driveway, this home feels like a world of its own, surrounded by mature trees and a sense of peace, while remaining minutes from everything that makes Wilton one of CT's most sought-after towns to put down roots. A stone front porch welcomes you, setting the tone for a home that balances warmth and elegance with features like skylights, vaulted ceilings, and beams.

Sarah Pritchard William Raveis Real Estate

2500 sq ft South Wilton Ranch with High-End Finishes Throughout, this beautiful home has been completely rebuilt down to the studs, offering a seamless blend of modern luxury and thoughtful design. Privately set back from the road, the home is approached by a long driveway and enhanced by newly installed deer fencing and gated entry, creating a serene and secure setting. Ideally located in South

Phil Candito Coldwell Banker Realty

This proven luxury home builder wants to build your future dream home on this rarely available one of a kind private lot. Drive down a private, hidden 1000+ foot driveway to find a property totaling over 2.00+ acres of unmatched and untouched exclusivity surrounded by protected state land. Add pool and tennis too! Two amazing potential lot sites. In addition, and even a possibility of

Evan Sheftel Millstone Real Estate Corp

Step into this welcoming 2-bedroom, 2-bath condo in the highly sought-after Village Walk community of Wilton! This beautifully updated unit is bathed in natural light and brimming with modern style including hardwood flooring, crown molding/trim, fireplace with custom mantel, offering the perfect blend of comfort and convenience. The main floor welcomes you with an open-concept living and dining

Karen Hagen Compass Connecticut, LLC

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

Marion Filley Compass Connecticut, LLC