Wilton CT Real Estate & Homes for Sale

Exceptional Custom Designed Contemporary Colonial Farmhouse Style Estate in South Wilton. Set on 3.1 pristine acres of flat, manicured land in coveted South Wilton, this newly constructed 6,400 +/- square foot masterpiece sets a new standard for luxury living. No expense has been spared in creating this exceptional residence, where thoughtful design meets uncompromising quality. The home's grand scale is immediately apparent in its open, light-filled spaces that flow seamlessly from room to room. State-of-the-art foam insulation ensures year-round comfort and energy efficiency, while designer moldings throughout add sophisticated architectural detail to every space. The heart of this home is its spectacular chef's kitchen with premium stainless steel appliances and custom cabinetry. A wraparound deck extends the living space outdoors, perfect for both intimate gatherings and grand entertaining while enjoying the private, pastoral setting. The 1,600 +/- sqft walk-out lower level is ready for you to customize, offering endless possibilities - from a rec/play room, wine cellar, a home theater or gym. The spacious rear property has ample room for a pool and cabana, for additional outdoor enjoyment. This versatile space allows future owners to truly make this house their own. With a combination of premium construction, generous proportions, and prime location, this South Wilton estate represents Connecticut luxury living at its finest, in a convenient setting.

Welcome to 10 Four Winds Drive, a distinguished Colonial residence situated in a private community in South Wilton, Connecticut. Built in 1994 on the historic grounds of the original Four Winds Farm, this expansive home offers a harmonious blend of classic elegance and modern functionality. Upon entering, you're greeted by a grand two-story foyer that seamlessly connects the formal living and dining rooms with the heart of the home-the family room and eat-in kitchen. The chef's kitchen is well-appointed and opens to a double-height family room featuring two-story windows, a fireplace, and a wet bar. The second level houses the primary suite, complete with a walk-in closet with built-ins, a bathroom with dual vanities, a walk-in shower, and a jetted tub. Three additional bedrooms and two full baths are also located on this floor. A versatile playroom is situated half a flight up from the kitchen and half a flight down from the bedroom level. The fully finished lower level offers a large open room that walks out to the backyard, featuring built-in desk cubbies in an alcove at one end and flanked by two separate multi-use flex rooms. This level also includes a kitchenette, a full bath, and a large storage room.

Nestled in a picturesque and serene neighborhood, this charming Colonial-style home offers timeless elegance and modern comforts on a spacious two-acre lot. With 4 bedrooms and 2.5 updated bathrooms, this home provides ample space for both living and entertaining. The main level features hardwood floors throughout, enhancing the warmth and classic appeal of each room. A bright and inviting kitchen opens to both a cozy family room with fireplace and a formal dining area, ideal for everyday living and special gatherings. Step outside to enjoy a screened porch perfect for relaxing summer evenings or entertain guests on the adjacent patio while taking in views of the beautiful property.Additional features include a convenient two-car attached garage with new doors, invisible pet fence, unfinished lower level with finishing possibilities and storage. Annual neighborhood block party, bus stop at the end of the driveway. Great street for walking, riding bikes and nearby access to the town forest with numerous walking trails. Whether you're seeking tranquility, space, or a welcoming community, this Colonial home checks all the boxes for comfortable and stylish suburban living. Convenient to schools, train, fields and shopping. Newer roof and cedar clapboard siding. Don't miss this one!

Picturesque 3 bed, 2.5 bath colonial, in prime location. Enjoy Wilton schools in a home that provides the best of both worlds: nature and convenience. The ample outdoor space provides 1.23 flat, usable acres and fenced in garden- while being steps away from the Branchville station, and nearby restaurants. Setup for entertaining, this home offers a front porch, large back deck, refreshed kitchen (with newer appliances), and plenty of outdoor access. The primary bedroom has ample space with an en-suite, large walk in closet, and a secondary closet. The basement offers open space and high ceilings- perfect for additional storage, a home gym or something to finish down the road.

Welcome to 53 Mountain Road in Wilton! This spacious 4-bedroom ranch sits on 2.5 acres and offers over 2,500 square feet of comfortable living space. Inside, you'll find 3 cozy wood-burning fireplaces, an updated kitchen with granite countertops, and stainless steel appliances. The home is bathed in natural light, highlighting the beautiful hardwood floors throughout, and the layout offers plenty of flexible living space for your needs. Enjoy one-level living with a flow that's perfect for both entertaining and day-to-day life. Step outside to the gorgeous backyard, complete with a stone patio - an ideal spot for outdoor relaxation and gatherings. The attached 3-car garage offers ample storage and parking. In addition, the privately owned solar panels help keep electric bills low, making this home both energy-efficient and eco-friendly. The location is super convenient-just a short trip to the Georgetown train station for easy commuting and close to Caraluzzi's Fresh Food Market, one of the best local grocery stores around. With its spacious layout, thoughtful updates, and prime location, this home truly has it all!

Beautifully sited gracious Colonial in great South Wilton location. Drive up the elegant entrance and enjoy the beautiful grounds creating a stately presence to this four bedroom home. Light and bright home with wonderful flow. Sun drenched living room with fireplace leads directly into large formal dining room off kitchen for easy entertaining. Lovely updated kitchen with its own eat in area/seating. Kitchen opens to great family room with second fireplace and access to deck for excellent outdoor entertaining. Large room over garage can serve multi purposes including home office, playroom, movie room..... Large unfinished basement with high ceilings has great potential to finish for additional living space. An abundance of windows and light make for a very sun filled happy home!

Historic Antique Colonial in South Wilton - Offered at $799,000 4 Beds | 2.5 Baths | 2,803 Sq Ft + 1,073 Sq Ft Unfinished Walk-Out Lower Level | 4.81 Acres with opportunity to build an accessory dwelling unit ("ADU"). Known as the historic "James Benedict" house, this central chimney, five-bay, 2-story, post and beam construction residence is one of the notable and better-preserved 18th century dwellings in town. Step into Wilton's past and reimagine its future within the walls of this charming home, offering 2,803 sq ft of cozy living space plus 1,073 sq ft of unfinished lower level space-ideal for future expansion. The possibilities for relaxation and entertainment are endless. Perfectly situated on a scenic lot in one of South Wilton's most desirable neighborhoods, this home blends timeless craftsmanship with the opportunity to create something truly special. From wide-plank hardwood floors and exposed beams to multiple gas/wood fireplaces, every historic corner tells a story. The unfinished lower level offers walk-out access, perfect for a home office, gym, playroom, or in-law suite. Highlights: 4 bedrooms | 2 full baths | 1 half bath. Has public water and a town sewer connection is available along the property line. Two staircases to upper level. Large kitchen with potential to open and modernize. Minutes to I-95, the Merritt Parkway, Wilton Center, schools, and train station.

This 4-bedroom home in desirable and convenient South Wilton offers the perfect blend of character, comfort, and potential, beautifully set on 1.3 acres above the scenic Norwalk River Valley Trail. The curb appeal will make you proud each time you travel up the driveway to the home, set high above the road. Inside you'll find a warm and welcoming layout filled with architectural character including rich wood flooring and moldings along with a fireplace framed with Moravian tiles. Sunlight fills the nicely proportioned rooms, especially the multi-windowed den and the bright kitchen with serene views of the backyard, the babbling Bryant's Brook, and the preserved woodlands beyond. While this home is ready to enjoy now, the potential is clearly there, including the possibility of a first floor primary bedroom and additional expansion. The landscaping enhances the setting while the attached 2 car garage offers everyday convenience. The ample flat yard, both front and back, offers room for expansion or simply an inviting place to garden, play or enjoy peaceful moments surrounded by nature.

Nestled in the heart of South Wilton, CT - a vibrant yet quaint Fairfield County town - this beautifully updated 4-bedroom, 2.1-bath Colonial sits on 1.24 private acres. Step through the front doors into a warm, inviting atmosphere where gleaming hardwood floors run throughout both the main and upper levels. At the heart of the home is the newly renovated chef's kitchen, complete with Quartz countertops, stainless steel appliances, and a spacious center island - perfect for entertaining or casual family meals. Natural light fills every corner of this home. The main floor features a front-to-back formal living room with a charming wood-burning fireplace, a formal dining room ideal for hosting dinner parties, and a stunning family room with vaulted ceilings and expanded windows. A recently renovated half bath and laundry room complete the main level. Upstairs, you'll find three generous secondary bedrooms and a full bathroom with double sinks and a tub/shower combo. The luxurious primary suite is a true retreat, featuring a spa-like bathroom with a soaking tub, glass-enclosed shower, and dual vanities. The finished walk-out lower level offers a versatile space, perfect for a rec room, playroom, or home gym. Offering the best of both worlds, this home delivers privacy with the convenience of being close to town.

Highest and Best deadline for Monday, 4/28 at 12pm.Nestled in the heart of historic Silvermine this updated Wilton charmer is sure to impress. Situated on 1.21 acres of beautiful property, this Colonial is convenient to both Wilton and New Canaan town center, schools, train and major highways, a true commuters dream! This gracious 4 bedroom, 3 full bath home has a spacious, light filled living room with fireplace and dining room perfect for holidays and family gatherings. The newly updated eat-in kitchen is a chef's delight with white cabinets, quartz countertops, island, updated appliances along with a sitting area, fireplace and french door to outdoor deck. Just a few steps away you will find the spacious family room with built-in book shelves, perfect for lounging, reading a book or watching your favorite movie. Half bath, foyer and office complete the main level. Upstairs you will find the primary bedroom with updated bath and plenty of closet space.Three additional bedrooms and an updated full bath complete the second floor. Other features of the home include central air, CITY WATER, solar panels, ring cameras, plus an outdoor deck, and 2 car garage.This unique neighborhood is ideal for walking and biking.One can enjoy a 1 mile scenic walk along the river to Graybarns restaurant or the Silvermine market for breakfast, lunch or dinner. Book your appointments today!

ENCHANTING ANTIQUE set on TWO lush LEVEL acres in a sought-after neighborhood. A gentle, colorful stone pathway welcomes guests to the inviting entrance. The bright, SUNLIT Kitchen features a delightful Dining area with a BUILT-IN corner hutch. The Media Room or Home Office is furnished with built-in BOOKCASES and one of three native field stone FIREPLACES. The expansive Family and Living Rooms offer flexibility in the floor plan, providing ample space for everyone. Period details showcase niches, original built-ins, and authentic WIDE BOARD flooring. The upper level boasts two spacious Bedrooms, one featuring a fireplace, while the third Bedroom is perfect for a nursery, home office, or yoga space. A large WALK-UP attic with wood flooring provides additional storage. The lower level includes laundry facilities and extra storage options. Outside, enjoy refreshing lemonade on the open porch while soaking in the soothing sounds of nature. Flat grassy paradise, perfect for outdoor shenanigans or to raise chickens. Nestled in a tranquil CUL-DE-SAC between the Ridgefield and Wilton Town Centers, this home enjoys the best of both towns. Wilton is known for its outstanding schools (with pick-up right at your doorstep) and convenient access to travel both North and South. Whether you're looking for a permanent residence or a cozy weekend getaway, this property offers it all. If you desire GREEN spaces, fresh country air, and a welcoming neighborhood atmosphere, come take a look.

Welcome to your dream home in the heart of Wilton. Nestled just moments from Wilton Center, this beautifully maintained and thoughtfully designed 4-bedroom, 4.5 bath Contemporary residence offers a perfect balance of elegance, functionality, and comfort. Step inside to discover the perfect floor plan ideal for modern living. The main level boasts a dedicated home office, perfect for remote work or study, along with a formal living and dining room. The spacious eat-in kitchen is the heart of the home, which seamlessly flows into two family room areas and a sunroom, with large windows which flood the home with natural light. Upstairs boasts three generously sized bedrooms, two of which share a well appointed hall bath, while the third enjoys the privacy of its own ensuite bath. The luxurious primary suite is complete with two walk-in closets and an updated ensuite bath featuring high-end finishes, a soaking tub, and walk-in shower. The finished lower level adds an additional 1,200 sq ft of living space featuring an entertainment room, home gym, and a potential fifth bedroom - perfect for quests, in-laws, or an au pair. The professionally landscaped yard features a large deck ideal for outdoor entertaining, with a fully functional hot tub included. The home includes a whole-house generator offering peace of mind in any season. This exceptional property checks all the boxes - space, style, location and livability. Don't miss the opportunity to make it yours.

Highest and Best deadline by Monday, 4/28 at 12pm. Welcome to 310 Ridgefield Road, located minutes away from Wilton Town Center, schools, train and major highways. This 4 bedroom, 2.5 bath Colonial awaits its new owner! The traditional, yet flexible floor plan has multiple living spaces making it ideal for todays modern day living. Highlights of the property include a spacious eat-in kitchen, 1/2 bath, light filled living room with fireplace, dining room plus a family room with built-in book shelves and access to the screened porch which overlooks the private backyard. Upstairs the primary bedroom has a walk-in closet and full bath, plus 3 additional bedrooms and full bath. Other features of the home include an attached two car garage, hardwood floors and central air. Don't miss the finished lower level with fireplace and access to the bucolic backyard. Updates to the house include a new roof, garage floor and carpet in family room. In addition, the interior is freshly painted, exterior power washed and trim painted. This is a wonderful opportunity for a new owner to personalize the house and make it their forever home!

Charming country colonial at the end of a private shared driveway conveniently located minutes from shopping, restaurants, schools, trains, 15 minutes from route 7 connector access to Merritt and 95. This amazing house has a gorgeous eat-in French county kitchen with counter seating and desk, formal dining room, formal family room, mudroom leading to oversized cozy den perfect for movie nights by the fireplace. 4 bedrooms upstairs, and fully finished basement can serve as a playroom, gym, office, whatever you need! Outside is a large deck fed by interior French doors, fully fenced yard, and awesome play set. Enjoy the pond view on your Adirondack chairs, pond is fully fenced. Home exudes character featuring reclaimed railroad ties in foyer and beams in primary BR, Den, family room which also features antique French doors and custom chandelier in Dining room. Immaculately maintained by loving homeowner, ready for you to call it home next. Truly a must see!

Step into the timeless charm of Rock House Woods, an enchanting 1800s farmhouse seamlessly blending historic character with modern convenience. A welcoming front porch invites you into this sun-drenched home, where wide-plank floors, exposed beams, and a beautifully designed chef's kitchen create an atmosphere of warmth and sophistication.The spacious family room, adorned with French doors, opens to a stunning flagstone patio-perfect for effortless outdoor entertaining. The newer primary suite impresses with a vaulted ceiling, a grand Palladian window, and a luxurious en-suite bath. Two additional bedrooms and a full hall bathroom complete the second floor. The versatile third-floor space is ideal for a home office, playroom, or 4th bedroom. For equestrian enthusiasts, this picturesque property features a well-appointed barn with a tack room, an additional three-stall stable, and two paddocks, offering the flexibility to convert them into a traditional lawn or even a potential pool site. Tucked away in a serene country setting, yet just minutes from shopping, dining, top-rated schools, and train access. This private oasis also boasts a new geothermal system and well pump. The possibilities here are endless -don't miss this rare opportunity to own a slice of history with all the comforts of today.

Welcome to this captivating artist's retreat - a home that beautifully fuses historical charm with modern convenience. Originally a horse barn transformed in the 1950s; this elegant home exudes warmth with its barn wood finishes, exposed beams, and wide plank floors. This property is not in a flood zone and does not require flood insurance. Spanning 1,194 square feet, it offers two inviting bedrooms and 1.5 bathrooms. The property is nestled on a private 1.7-acre lot, providing a serene escape with the convenience of close proximity to Wilton Center, Bradley Park, the Norwalk River Valley Trail and the commuter train. The modern amenities include central AC and a whole-house generator. Ensuring comfort and peace of mind. Outside, you will find a secluded patio ideal for outdoor dining. The shed is finished and has electricity. Sewer, town water, and natural gas are available for hookup. Ask about the rental history if you are looking for an income stream.

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, this home 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.

Exquisitely blending European sophistication with historic charm, this estate radiates timeless appeal. Set on a meticulously landscaped, level lot, the property features an in-ground Wagner gunite pool, mature plantings, and charming outbuildings that invite leisurely outdoor living. Expansive terraces flow effortlessly into multiple indoor spaces, creating an ideal setting for entertaining-whether you're dining al fresco, relaxing poolside, or enjoying the generous yard. Inside, oversized windows and French doors bathe the home in natural light, showcasing the exceptional craftsmanship found in every detail. Three fireplaces add warmth and elegance, while the seamless flow between the living, dining, and kitchen areas makes the home perfect for both intimate gatherings and grand celebrations. Private wing with separate entrance and full bath offers a serene retreat for extended family and guests, ensuring privacy throughout. A dedicated studio space provides an inspiring environment for work, study, or creative pursuits. Celebrated by designer-artists over the years, this home is ready to welcome its next discerning owners. Additionally, a separate space above the spacious two-car garage presents the potential for an in-law suite or a standout studio complete with an en-suite bath.

This extraordinary property stands as a testament to thoughtful preservation and modern comfort. Built in 1969 with portions dating to the 1700s, this dramatic barn home is perfect as a weekend retreat or multi-family residence. Featuring soaring 11-foot ceilings and walls of glass that flood the interior with natural light, this artistically designed home balances historic character with contemporary functionality. The estate includes a guest cottage with its own kitchen, family room and private entrance-ideal for extended family or weekend guests. Impressive structural elements include massive timber beams-some spanning 55 feet-salvaged from the iconic Ruppert Brewery in Manhattan, which once produced America's best-selling beer. The historic connection extends to Colonel Jacob Ruppert, known for building Yankee Stadium and bringing baseball legends Babe Ruth, Lou Gehrig, and Joe DiMaggio to New York. Additional amenities include a dedicated gym space, brick wine vault, and expansive level grounds for recreation, with space for a pool and organic garden. Situated on a desirable cul-de-sac in South Wilton, this completely renovated property offers a rare combination of historic significance, architectural distinction, and modern living. Whether seeking a primary residence, multi-generational family compound, or luxurious weekend escape, this versatile estate delivers exceptional value. Historic Manhattan Timbers Meet Modern Country Living at this Wilton stunner. A must

Welcome to 6 Forest Lane! This stunning Cape Cod is beautifully situated on a corner lot surrounded by lush and professional landscaping designed by Sev Group. Updated and meticulously maintained, it offers the perfect balance of character and modern convenience. Completely gutted in 2014, the home boasts beautifully updated bathrooms and a spacious, functional layout. With ample closet space and a well-appointed pantry, there's no shortage of storage throughout. Upstairs, two additional bedrooms and a full bath finish the space. For peace of mind, the most recent upgrades include a brand-new washer and dryer, purchased in October 2024, along with a new oil tank for added peace of mind. Outside, be captivated by the stunning landscape surrounding the property and the storage shed providing additional space for all your outdoor gear and tools. Forest Lane is a tranquil horseshoe -ideal for peaceful walks and enjoying nature. Located just moments from the town center, near the New Canaan border, and steps away from all of the wonderful Wilton amenities, you'll love the convenience and charm of this location. Other notable features include a tankless water heater, ensuring on-demand hot water throughout the home. This is a rare opportunity to own a beautifully renovated home in a prime location.

Stately pillars welcome you at the entrance of a circular driveway that leads to this elegant home, nestled on one of the most coveted streets in a sought-after neighborhood. Perfect for entertaining, both indoors and out, this ideal residence boasts a well-designed layout. An efficiently designed kitchen with a dining area for casual eating forms the heart of the home. The expansive family room, seamlessly connected to the kitchen, features large windows overlooking a serene backyard, enhancing the feeling of openness and tranquility. The formal dining room with a bay window offers ample room for hosting family gatherings and celebrations. Upstairs, four bedrooms and two baths await, including a generous primary bedroom with a spacious walk-in closet. On the lower level, discover an exercise room and play area, adding to the home's versatile charm. Plenty of closets and storage space throughout the home enhance practicality and organization. The home features a brand new heating system, central air system and septic tank! Located in a walkable, bikeable and hikeable neighborhood that is less than ten minutes from Wilton's town center, schools and train. It's also conveniently located just a short ride from Ridgefield's town center offering more fine dining, access to the skating rink, and live entertainment at the playhouse. This welcoming home is ideal for it's lifestyle and convenience!

Tranquil contemporary nestled on a private cul-de-sac on almost two level acres. Beautiful cathedral ceilings and exposed beams create an open floor plan perfect for entertaining.

Luxurious Keelers Ridge Estate: A Serene Sanctuary of Sophistication and Comfort Nestled on a private cul-de-sac in the prestigious Keelers Ridge neighborhood, this executive property is a testament to luxury, tranquility, and meticulous upkeep. Spanning over 2 acres of meticulously curated gardens and specimen plantings, this oasis promises an ambiance of refined elegance and natural beauty. As you enter this magnificent retreat, you are greeted by the warmth of the rising sun, while the evenings are graced with breathtaking sunsets. The estate's incredible landscaping showcases year-round plantings, creating a living tapestry that evolves with the seasons. The residence boasts a suite of upgrades, including a high-tech generator (2021/22) with a self-diagnostic feature, ensuring uninterrupted comfort. The roof has been expertly upgraded and sealed, while the swimming pool has been enhanced with a new heater, cover, and filter. The interior is a paragon of exquisite maintenance, featuring a wine cellar and exercise room that cater to both connoisseurs and fitness enthusiasts alike. The main house offers five bedrooms, including a convenient suite on the main level, perfect for multi-generational living or guest accommodation. Newly built cedar pergolas and a charming cupola atop the pool house add to the estate's allure, while the new HVAC system (2024) ensures modern comfort.

Rare build to suit opportunity on a stunning North Wilton property that also includes a barn and a gorgeous 3-car detached garage with space upstairs for a studio/1BR apartment! This bucolic property is almost two acres and features classic New England stone walls, beautiful mature trees and is located on a quiet and prestigious tree-lined street, minutes to both Wilton and Ridgefield town centers! Partner with one of the area's premier builders, Sturges Brothers, to create the custom home of your dreams. The detached garage boasts two fireplaces and partially finished space upstairs. Follow the stone steps to the rear of the property to the barn, complete with chandeliers (and electricity) which most likely holds many interesting stories from years past! Both the garage and barn have new wood roofs.

Fantastic rebuild/expansion opportunity on this stunning property that also features a barn and 3-car garage with upstairs space! Here is your chance to partner with premier period restoration builder, Sturges Brothers who completed the Keeler Tavern restoration project, among many others. The historic 1790 Betts home will be transformed into a modern and sophisticated 4BR/3.5BA home. Addition will be custom tailored to buyers needs. High end appliances, sleek fixtures and elegant detailing will blend harmoniously with the original wide plank floors, doors and sconces as well as a double-sided fireplace in the dining room and study. The main level will feature an open floor plan with an eat-in kitchen, spacious living room, powder room, a luxurious primary suite w/fireplace and a screened porch. Upstairs will be 3 additional bedrooms, another study and two full baths. Need a craft studio or separate space for guests? The gorgeous detached garage boasts two fireplaces and a fabulous space upstairs that is partially finished. Follow the stone steps to the rear of the property to the barn, complete with chandeliers (and electricity), which most likely holds many interesting stories from years past! Both the garage and barn have new wood roofs. All of this is set on one of the most bucolic properties in Northern Wilton on a quiet and prestigious tree-lined street, minutes from top-ranked schools, both Wilton and Ridgefield town centers, and just about an hour from NYC!