472 properties for sale in South Wilton

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

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 and 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

SELLERS ARE AKSING FOR HIGHEST AND BEST OFFERS BY 4PM MONDAY JUNE 1ST*Set on a beautifully landscaped, bucolic acre at the top of a quiet cul-de-sac in Westport's coveted Old Hill neighborhood, this charming cottage-style ranch home offers the perfect blend of modern convenience, and luxurious Westport lifestyle. Move-in ready and beautifully maintained it's thoughtful layout is ideal for both everyday living and gracious entertaining. Light pours in through picture windows, French doors, and skylights giving a bright airy feel throughout. At the heart of the home is a stunning chef's kitchen equipped with high-end stainless steel appliances. The open dining area is perfect for feasts with family. Sliders leading to multiple decks make indoor-outdoor living seamless. Relax in the inviting living room with a cozy fireplace, or entertain outdoors on the expansive deck overlooking lush lawns. Retreat to the primary suite that boasts a newly renovated spa-like bath. Two additional bedrooms

Incredibly located moments from town and convenient to schools, shopping, commuting options and more, this sparkling home showcases pride of ownership. A new 2026 driveway leads to the landscaped setting, where this gracious home with an in-ground Wagner pool is set amid.74+/- acre. The two-story foyer introduces crisp, timeless spaces, and a home that has been impeccably maintained. The living rm w/ the first of 3 fireplaces and a beautiful dining rm w/lit tray ceiling are ready for entertaining. The large gourmet kitchen w/ marble counters, La Cornue range plus wall ovens, Sub Zero, island and pantry has a sun-filled breakfast rm that leads to the lrg fam rm w/ custom built-ins, stone fpl w/ gas log set and two sets of doors to the newer deck. The mudrm has a casual entrance, door to pool, half bath and access to the 3-car garage. Upstairs, a hall w/ window seats leads to the primary suite w/ fpl, dual walk-in clsts and luxe bth. Each remaining BR is spacious and well-appointed. A fl

Welcome to 6 Three Seasons Lane, a meticulously maintained Colonial set on a beautifully landscaped lot in Norwalk's highly sought-after Wolfpit neighborhood. Thoughtfully updated for low-maintenance, easy living, this inviting home features a bright, open floor plan, hardwood floors, stainless steel appliances, new siding, brand-new windows, a new roof, newly added insulation, and a high-efficiency heating system. A gas-log fireplace creates a warm and welcoming focal point in the living space, perfect for cozy winter evenings. The flexible main-level layout also offers the potential to create a first-floor primary suite and expand the existing half bath into a full bath. Outside, the manicured backyard feels like a private oasis, complete with an underground sprinkler system and a paved patio area that is ideal for entertaining, with seamless flow from indoors to out. Just minutes from Westport shops, restaurants, commuter routes, and everyday conveniences, this truly turnkey home is

Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with Thermador range and walk-in pantry opens to the home's inviting living and dining areas. Over $600K of recent updates including the stunning, newly-redesigned primary suite - a true sanctuary, with a new focal wall with custom cabinetry and gas fireplace, a well-equipped bath with dual sinks, tub and shower, plus a distinctive turreted sitting room, an idyllic space to relax. Multiple home office options. A new outbuilding elevates the property to an entirely new level. Designed as a private wellness retreat, this extraordinary Onsen-inspired space features hot and cold plunge pools, a sauna, sh

Storybook charm and effortless living come together in this beautifully maintained stone-and-shingle ranch, ideally located in the heart of Lower Weston. Set majestically on more than 3 private acres with a sparkling heated pool, mature specimen trees, and sweeping lawns, this special property offers an exceptional blend of tranquility and convenience-just steps from Weston Center, the library, award-winning schools, and only minutes from the Westport line. Lovingly cared for and thoughtfully expanded, the home is filled with natural light and a warm, welcoming ambiance. Expanded by current owners, the flexible floor plan offers 4 bedrooms, 3.5 baths and comfortable living spaces designed for everyday enjoyment and entertaining. At the heart of the home is an inviting kitchen that flows seamlessly into a sunken family room. A charming breakfast area and window-lined sun room capture views of the grounds. A spacious dining room, with its own sitting area and access to the deck, provides

Don't miss this rare opportunity in Norwalk's highly sought-after Wolfpit neighborhood! This expanded Cape offers exceptional potential for investors, renovators, or buyers looking to create their dream home while building instant equity. The main level features 3 bedrooms and 2 full bathrooms, providing comfortable one-level living. Upstairs, you'll find two generously sized bonus rooms, an additional full bathroom, and two large storage closets, offering endless possibilities for home offices, guest rooms, additional bedrooms, or flexible living space. The versatile floor plan allows you to customize the home to fit your needs while adding tremendous value. Ideally situated on a quiet residential street just minutes from schools, parks, shopping, restaurants, Metro-North, and major commuter routes. Whether you're searching for your next fix-and-flip project or a home to renovate and make your own, opportunities like this in Wolfpit don't come around often

Nestled in the heart of Westport, Connecticut, this stunning new construction residence redefines elegant suburban living with unparalleled sophistication, timeless grace and is complete and ready for immediate occupancy. Boasting six generous bedrooms and six luxurious bathrooms, the home features soaring nine-foot ceilings that bathe its expansive interiors in natural light and create an atmosphere of airy grandeur. Thoughtfully designed with premium finishes, custom millwork, and state-of-the-art systems. From the chef's kitchen with Thermador Appliances and a commanding kitchen island to the serene primary suite with a warming fireplace and a walk in closet fit for royalty; every detail invites effortless entertaining and refined daily living. Spanning three floors, this home offers exceptional versatility with a peaceful third floor sanctuary housing a private office and media room for entertainment or productivity. The finished lower lever further elevates the lifestyle with a sp

Get ready to make 19 Vineyard Lane home! This wonderful family home is ideally situated in the heart of Westport, offering 5 bedrooms and 2.5 baths designed for comfortable, everyday living and effortless entertaining alike. Lovingly cared for by its current owner for 50 years, this home features a first-floor office, while the partially finished basement offers space for a gym or playroom. Set on 1.24 flat acres, beautifully maintained with mature trees, an irrigation system, and room for a pool. Additional highlights include a whole-house generator, security system, irrigation and central air conditioning. Location is everything, and this home delivers. It's walkable to Wakeman Town Farm, to the playing fields at Wakeman and to Staples High School, making morning drop-offs a breeze. Right around the corner is recently opened local favorite Gruel Britannia, perfect for a quick coffee, bite, or catch-up with neighbors. This is more than a house - it's a place to put down roots in one o

Nestled in one of Lower Weston's most desirable locations, this beautifully updated and thoughtfully expanded 5-bedroom, 3.5-bath residence offers the perfect blend of timeless charm and modern living. A bright open floor plan centers around a stunning great room with soaring vaulted ceilings and a dramatic double-sided fireplace that creates a warm connection between the kitchen and family room. The gourmet kitchen includes marble countertops, Wolf, Subzero and Gaggenau appliances and includes a cozy breakfast room and home office. Perfect for entertaining, the home flows seamlessly to a beautiful screened porch and sunny deck overlooking an expansive, level backyard complete with a private, lighted tennis court, providing an exceptional setting for recreation, gatherings, and room for pool. The luxurious primary suite serves as a private retreat, featuring a spectacular spa-inspired bath with soaring ceilings and two spacious walk-in closets. The walk-out lower level provides excepti

Prepare to be dazzled! A blend of sophistication and charm, this Federal-style colonial offers a combination of custom finishes and period details to create a home to suit a variety of lifestyles! It starts with the gorgeous 2 acres of level and dry property featuring gunite pool, changing cabana and spectacular pavilion w/ grilling station, dining and seating areas and outdoor fireplace. An outdoor living space for all seasons! Your friends will never want to leave and that's ok because in addition to the gourmet kitchen w/high end stainless steel appliances, sun-filled dining area and family room w/fireplace and built-ins, there is a banquet sized dining room w/ fireplace and climate controlled wine room and butler's pantry, as well as a large living room w/ fireplace to host your guests. An entertainers dream! There is room for everyone with the 5 ensuite bedrooms including fabulous primary w/ fireplace, sunroom and huge walk in closet/dressing room. The fun continues in the finishe

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 genero

Welcome to 36 Richmond Drive! Tucked into a great Darien neighborhood, this three-bedroom, two-bath ranch is close to everything, bike to Cherry Lawn Park, walk to local shops and restaurants, or hop on the train in minutes. The home sits on a level, corner lot of over half an acre, with stone patios, a built-in grill, and plenty of yard space for play and entertaining. Inside, you'll find a lower level that's perfect for hanging out, with a playroom, bar, and a cozy wood-burning stove. Whether you're ready to update and make it your own, or you're looking for a project with great potential, this home is a terrific opportunity. All in the award-winning Ox Ridge Blue Ribbon School district!

This sun-kissed contemporary captivates with private panoramic views overlooking the forever-green 14th and 15th fairways of Aspetuck Country Club. Designed to fully embrace its striking setting, this home offers a wide deck, large patio, five balconies, and grand windows framing views. Sited on two idyllic acres in bucolic Lower Weston, this premier property is minutes to the amenities and train stations of Westport and Fairfield. The home's immaculate exterior sets a welcoming tone with an oversized front porch with seating that beckons you inside. Upon entry, the home unfolds with an open layout featuring vaulted ceilings, skylights, walls of glass, rich wood floors, and fireplaces that add warmth and character. The main house offers a first-floor primary suite with walk-in closet and sunlit bath with double sinks, tub/shower, and sauna, along with access to a versatile loft. The great room features a dramatic two-story fireplace and flows into the dining room, living room, and kitc

Beautifully renovated 4-bedroom, 2.5-bath home set on a picturesque 1-acre property surrounded by mature trees, offering exceptional privacy and a peaceful connection to nature. Filled with natural light, the open-concept floor plan is designed for both comfortable everyday living and effortless entertaining. The stunning kitchen features custom cabinetry, a large center island, and beautiful views of the backyard, screened porch, and inground pool. The kitchen flows seamlessly into the dining area and spacious living room with a fireplace, creating a warm and inviting atmosphere. Both the kitchen and family room lead to a beautiful screened porch with dual ceiling fans, providing the perfect space to relax, dine, and enjoy the changing seasons before stepping onto the patio and taking a refreshing dip in the pool. Upstairs, the luxurious primary suite features a custom walk-in closet, soaking tub, oversized shower, and double vanity. Three additional spacious bedrooms share an updated

Significant Price Improvement! Motivated seller has repositioned this exceptional home to present an outstanding opportunity in one of Norwalk's most sought-after neighborhoods. Nestled on a picturesque tree-lined street in Cranbury, this beautifully maintained 4-bedroom, 3.5-bath Colonial offers a rare combination of flexible multigenerational living, exceptional privacy, and generous indoor-outdoor living. Set on beautifully landscaped grounds, the home provides a peaceful retreat complete with an inground pool, spacious patio, and multiple outdoor areas perfect for relaxing or entertaining. An inviting foyer welcomes you to a spacious living room and formal dining area, while the updated eat-in kitchen features custom cabinetry, quartz countertops, and a center island. Just beyond, the stunning family room with sliding glass doors opens seamlessly to the backyard. The thoughtfully designed layout includes a main-level suite with a private bath and direct deck access, ideal for an in

A Masterpiece of Colonial Elegance and Resort-Style Living on Dunning Road - Perfectly positioned on a coveted cul-de-sac just moments from town on 2 perfectly flat acres, this stately 5-bedroom, 6.5-bath center hall colonial offers an unparalleled blend of sophisticated design and private resort living. Inside, the formal living room sets a dramatic tone with its stately fireplace and a breathtaking wall of windows framing views of the lushly landscaped backyard oasis, while a separate, sun-drenched solarium provides a tranquil and private retreat for quiet relaxation. The heart of the home is a designer kitchen equipped with professional-grade appliances, a massive center island, a walk-in pantry, and an adjacent breakfast room and separate command center-all seamlessly connecting to a formal dining room and opening through floor-to-ceiling glass French doors to the pool and cabana. For everyday gathering, a separate family room features custom built-ins and its own fireplace, comple

Imagine starting your morning with coffee on your private bedroom deck as sunlight pours through the windows, then ending your evening relaxing on the patio or enjoying the peaceful surroundings from one of three outdoor living spaces. Welcome to 100 Wolfpit Avenue #14, a townhouse that offers the space, flexibility, and lifestyle rarely found in condominium living. Spanning three finished levels, this home lives more like a single-family residence while offering the convenience of a well-maintained community. Abundant windows fill the home with natural light throughout the day, highlighting hardwood floors, crown molding, recessed lighting, custom raised paneling, and thoughtful updates. The kitchen features shaker-style cabinetry, granite countertops, stainless steel appliances, a double oven, and generous workspace for cooking and gathering. Upstairs, both bedrooms offer double closets and private decks. The finished lower level provides flexible space for a family room, office, gym

This artistically inspired Lower Weston retreat comes with a separate guest house, saltwater pool and beautifully cultivated grounds enhanced by numerous specimen trees and beautiful shrubs. The 2,506 sq. ft. main residence features an expansive first-floor primary suite with sitting room or study. Two sets of French doors lead to either the tranquil, private pool or one of several stone terraces. A dressing room lined with custom closets completes this private wing of the main house. A dramatic two-story living room showcases a striking stone fireplace with antique marble mantel, vintage Venetian chandelier and elegant iron railings. The main house offers three bedrooms plus a finished lower-level room with fireplace, ideal for a den or playroom. A separate 760-square-foot guest house includes a great room, bedroom, fully renovated bathroom, vaulted ceiling with skylights, and private deck. New mechanical systems provide added peace of mind. This rare offering combines privacy, charac

Well maintained contemporary style home with many upgrades and improvements, including remodeled bathrooms, finished lower level playroom and exercise room, new furnace, full house generator, freshly painted. The cook in your family will love the spacious eat-in kitchen with high end appliances. Impressive great room with vaulted ceilings and lots of glass for natural light Lovely landscaped property with room for a pool (plans available). Wrap around deck with hot tub. Walk to Weston Center and schools

Embrace the ultimate country club lifestyle at this stunning two-acre estate, where privacy and recreation meet in perfect harmony. The grounds are rich with amenities, including a sparkling Gunite pool and spa, a private tennis court, and a separate sport court. The thoughtfully designed pool house elevates every gathering with its summer kitchen, changing room, half bath, and refreshing outdoor shower. Perched above the detached garage, you'll find a quiet retreat with a half bath - the perfect set up for a professional home office, a dedicated creative studio, or a home gym. The main residence is a sun-drenched contemporary, offering three finished levels of effortless living. Soaring ceilings and well-placed skylights create an airy atmosphere, while hardwood floors anchor the intuitive floor plan. All four bedrooms are tucked away on the upper level. The walkout lower level adds even more versatility, ready to serve as a media room, play room and/or a fitness hub to suit your need