450 houses for sale in Winnipauk

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

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

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

Introducing a one-of-a-kind gem in Darien: the historic Eliaseph Whitney House, originally built in 1770, nestled on an expansive 4.12-acre parcel- one of the largest of its kind in town. This iconic property effortlessly blends centuries-old charm with modern-day functionality. Step inside to discover timeless details like wood-beamed ceilings and floors, multiple fireplaces, a cozy den and library, all complemented by bright, open living spaces with a kitchen family room space built for today's lifestyle. Two garage spaces offer room for six cars and incredible storage. The surprises don't stop indoors-step outside into meticulously maintained grounds showcasing a gorgeous pool, landscaping, split rail fences, and charming stone walls that evoke a sense of storybook elegance. A sprawling, incredible field offers endless opportunities for recreation or relaxation, and the potential to divide the property into two lots opens the door to even more possibilities. Adding to the allure is

Highest and Best offers are due Monday, July 13th at 12:00 PM. Welcome to your perfect suburban retreat! Thoughtfully renovated throughout, this four-bedroom, three-bathroom home seamlessly blends timeless style with everyday comfort. Inside, you'll find bright, inviting living spaces, a formal dining room, and a beautifully renovated eat-in kitchen with breakfast nook that opens seamlessly to the backyard. Upstairs, the new spacious primary suite features a vaulted ceiling, walk-in closet, office and a gorgeous en-suite bath. Two additional bedrooms, a recently renovated bathroom and a conveniently located laundry room complete the second level. Set on.65 beautifully landscaped acres, the fully fenced backyard is perfect for relaxing or entertaining, with a detached studio that's perfect for a home office or gym, fire pit, large playset, and storage shed for added versatility. Ideally located just minutes from downtown Darien, the train, beaches, parks, and major commuter routes, this

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

In the owners' words. We moved to this home looking for an escape from city life and a place to grow our family. It has offered us all of that and more. Every inch of the home serves a purpose, creating a space that feels intentional and complete. The thoughtful size and open layout means we are never far from one another. We can prepare meals in the kitchen while watching our little ones play in the family room. It truly brings a family together. With an abundance of windows, the living area draws the outdoors in and floods our home with natural light. We love enjoying a cup of coffee in the breakfast nook while looking out at the yard and appreciating the beauty of each season. Outside, we all spend countless hours exploring the spacious yard - racing around the house, crossing the bridges, searching for frogs in the brook. This is a home that lets us embrace nature. As much as this home feels like a private retreat, we love the convenience of its central location and being able to g

In today's world, there is nothing more important than having a place to gather. This private retreat with a stunning residence and amazing recreational facilities can become your own private sanctuary with a tennis court, heated Gunite pool and separate pool house set among lush, meticulously curated grounds on almost 2.4 acres. This 6,700-square-foot shingle-style residence offers refined luxury across three expansive levels, combining architectural sophistication with a warm sense of livable comfort. The main level flows beautifully and showcases dramatic interiors with large gathering spaces, gourmet kitchen facilities and incredible entertaining capabilities. The main floor primary suite serves as a luxurious private retreat with his and her bathrooms and separate sitting room/office. Upstairs, three additional bedrooms continue the home's commitment to comfort and privacy. The finished lower level extends the home's appeal with numerous recreational spaces and a full bath. Beyond

Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspir

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

Set on one of Darien's most sought-after, multi-million dollar cul-de-sacs, this sprawling wood and brick ranch offers exceptional scale and endless potential for the discerning buyer, renovator, or builder. Positioned on a remarkably private 2.5 acre lot, abutting another 10+ acres of protected wetlands, the setting affords unmatched peace, natural beauty, and exclusivity. The interior boasts a versatile layout. The back of the home features expansive walls of glass, with a fully enclosed glass terrace, which creates a seamless visual connection to the serene, wooded surroundings. Highlights include 3 generously sized bedrooms, 3.5 baths, a sauna, a spacious living room anchored by a beautiful stone fireplace, a formal dining room, and a large eat-in kitchen, with a large breakfast area. Designed with an indoor-outdoor flow in mind, the substantial multi-purpose room anchoring one end of the house, can be used according to any family's needs: a playroom, family room, studio, in-law su

This beautifully renovated 5,200-square-foot home offers an exceptional blend of timeless elegance and modern luxury in one of Darien's most coveted central locations. Step inside to discover a spacious, light-filled open floor plan designed for both everyday living and effortless entertaining. The inviting family room with fireplace flows seamlessly into the gourmet kitchen and expansive breakfast area, creating the heart of the home, while an additional oversized living space added during the 2019 expansion offers incredible flexibility for relaxing, gathering, or entertaining. A dedicated office provides a quiet workspace, and the beautifully appointed formal dining room is ideal for more elegant occasions. Every bathroom in the home has been thoughtfully redesigned with high-end finishes, and the residence was extensively expanded and renovated in 2019. Upstairs, five generous bedrooms provide plenty of space for family and guests, including a retreat-like primary suite complete wi

Set on 1.57 picturesque acres this beautifully reimagined farmhouse colonial pairs timeless New England character with a comprehensive top-to-bottom renovation. From the original windows and hand-laid stone floors to the reclaimed shiplap walls and solid wood doors, every detail honors the home's 1959 roots with modern systems and design. A recent full-scale renovation touched virtually every system in the home - HVAC, tankless water heater, plumbing, electrical, kitchen, baths, flooring, and millwork -move in with confidence and none of the guesswork of an older home. The main level offers the open, connected layout today's buyers are searching for: a flowing family, living, and dining space anchored by three wood-burning fireplaces, a dedicated home office, and a bright four-season sunroom perfect for year-round enjoyment. The kitchen is a true showpiece, featuring marble countertops and a professional-grade appliance suite, ideal for both everyday living and entertaining. Upstairs,

Nestled on a private 1.4-acre cul-de-sac property in Darien's sought-after Tokeneke school district, this gracious Colonial offers over 5,700 square feet of living space, exceptional privacy, and effortless indoor-outdoor living. Surrounded by landscaping and an expansive lawn, the home is a true retreat complete with a saltwater pool, patio with built-in grill, and greenhouse. Designed for comfortable daily living and memorable gatherings, the main level features a formal living room with fireplace, a dedicated home office, and French doors that open to a charming sunroom. The spacious, updated kitchen serves as the heart of the home, featuring a sunny breakfast room, and opens to a sitting room with a fireplace and dining room. A light-filled great room seamlessly flows to the outdoor entertaining areas overlooking the property. Upstairs, the primary suite features a walk-in closet and private bath, while additional bedrooms and multiple full baths provide ample accommodations for fa

Tucked behind classic wood rail fencing and stone walls, this beautifully updated Colonial offers the perfect blend of charm, privacy and modern comfort. Improvements include newly renovated baths, new windows, new roof, new kitchen appliances and several other updates that have created a move in ready appeal. Inside, a welcoming floor plan features formal living and dining rooms with French doors that open to an expansive wraparound deck, making indoor outdoor entertaining effortless. The sun filled family room showcases soaring vaulted ceilings, while the well appointed kitchen and main level powder room provide everyday functionality. The primary suite offers a custom walk-in closet and en suite bath. Two additional bedrooms and a full hall bath complete the second level. The finished walk-out lower level complete with its own entrance provides flexibility as a home office, playroom fitness space or guest suite. Outside enjoy peaceful evenings on the back deck, relax beside the babb

Set on a quiet, peaceful street, this well-maintained split-level home on 1.6 acres delivers exceptional privacy while remaining moments from the heart of Silvermine's historic charm. Just a short drive to GrayBarns, the Silvermine Arts Center, and Silvermine Market, the home is ideally positioned to enjoy the area's distinctive village lifestyle. The main level showcases modern, open-concept living. At its center is a fully renovated, chef-inspired eat-in kitchen featuring premium appliances, a high-efficiency induction cooktop, and peninsula seating. The kitchen seamlessly connects to the expansive main living and dining areas, ideal for both everyday living and entertaining. An inviting living area with cathedral ceilings and a cozy fireplace opens through sliders to a deck overlooking the beautifully manicured backyard. The finished walk-out lower level offers exceptional flexibility, functioning beautifully as a media room, guest suite, or in-law setup. This level includes a fourt

Nestled in New Canaan's coveted Silvermine neighborhood, this beautifully maintained 4-bedroom, 2.5-bath Colonial offers the perfect blend of timeless charm and modern living. Set on 1.07 private acres just moments from the Silvermine Arts Center, GreyBarns, and all that New Canaan has to offer, this special property combines a sought-after location with exceptional indoor and outdoor living spaces. The heart of the home is the impressive great room, where the spacious kitchen flows seamlessly into the sun-filled family room with soaring ceilings, creating an inviting space for everyday living and entertaining alike. French doors lead to a newly constructed enclosed deck overlooking the expansive, level backyard, providing a peaceful setting to relax, dine, and gather with family and friends. The thoughtfully designed floor plan also includes a dedicated first-floor office, ideal for today's work-from-home lifestyle. Upstairs, the spacious primary suite offers a private retreat complet

Completely renovated and move-in ready, this stylish two-level townhouse offers the perfect blend of comfort, convenience, and value in Norwalk's desirable Spring Hill neighborhood. Featuring 2 bedrooms and 1 beautifully updated bath, the home has been thoughtfully upgraded throughout with a brand-new kitchen, new appliances, sleek countertops, and a tiled backsplash designed for modern living. Newly refinished hardwood floors and custom window treatments add warmth and character, while natural light fills the spacious layout across both levels. Enjoy the peaceful courtyard setting, heat and hot water included in common charges, onsite laundry just downstairs, one detached garage space, plus an additional assigned parking spot. Ideally located steps from Norwalk Hospital and minutes to the SoNo Collection, restaurants, Metro North, major highways, and easy access to NYC

Enjoy the ease of in-town living at its finest. Ideally located just moments from restaurants, shops, library, farmer's market, movie theater, the Metro-North train and local churches. This home offers exceptional convenience with no car required. Set on a quiet cul-de-sac, the property combines peaceful surroundings with close proximity to all the amenities of town. A rare opportunity, this legal two-family residence offers outstanding flexibility, live in one unit while generating rental income from the other, or rent both units. Perfect for commuters or those seeking a weekend retreat, the home also features a sunny backyard, ideal for gardening, relaxing, or entertaining. Thoughtfully updated, the main house includes a new washer and dryer (2026), new dishwasher and hood (2025), a perimeter fence (2023), a mini-split heating and cooling system (2023), a roof installed in 2021, and a whole house water filtration system in place. The apartment has also been well maintained with a new

Welcome to this fabulous, completely updated corner-unit townhome, perfectly situated in the heart of New Canaan, steps from downtown. Bathed in natural light from multiple exposures, this exceptional 3-bedroom, 2-full bath residence seamlessly blends timeless style with modern comfort, offering a turnkey lifestyle in one of Fairfield County's most sought-after communities. The thoughtfully designed open floor plan creates an inviting atmosphere for both everyday living and entertaining. Beautifully updated interiors flow effortlessly from room to room, including a flex-space bedroom with a Murphy Bed that converts into a desk for office use. A highlight and one-of-a-kind feature is the recently renovated screened-in porch. This charming outdoor retreat extends your living space and offers the ideal setting for morning coffee, alfresco dining or simply unwinding while enjoying nature. Rarely available in these townhomes, #84 features an in-unit washer and dryer which adds to the home's

Welcome to one of Orchard Hills' most exceptional residences, a stunning, fully renovated end-unit offering the privacy and feel of a single-family home with the ease of luxury condominium living. Reimagined with over $300,000 in renovations and improvements in 2023 and 2024, this light-filled home showcases impeccable craftsmanship and designer finishes throughout. The elegant open floor plan is perfect for everyday living and entertaining. The chef's kitchen (remodeled in 2015) features custom cabinetry, and beautiful finishes that flow into sophisticated dining and living spaces centered around a charming wood-burning fireplace. Wide-plank hardwood floors, Andersen windows, custom millwork, new doors, lighting, paint, and Hunter Douglas window treatments enhance the home's refined aesthetic. Upstairs are two luxurious bedroom suites, including a spacious primary suite with multiple closets, a walk-in closet, and beautifully appointed bath, plus a newly created second-floor laundry r

Featured in multiple publications and set along New Canaan's coveted Smith Ridge Road, this magazine-worthy, extraordinary estate is a masterclass in privacy, beauty, and timeless luxury. Privately nestled on more than five spectacular acres just moments from town and the New Canaan Country Club, the property offers a lifestyle that feels remarkably tucked away and private. Surrounded by sweeping lawns, curated grounds, and an atmosphere of complete tranquility, it is the kind of place that instantly slows time and is rarely available. Sunlight pours through every room, illuminating interiors that have been meticulously maintained and thoughtfully designed with an uncompromising commitment to quality. From the highest-end designer kitchen to the gracious entertaining spaces, every detail reflects exceptional craftsmanship, sophistication, and enduring style. The primary suite is a destination unto itself-a private retreat defined by sumptuous finishes, spa-like comforts, and an effortl

Set on 4 private acres, this fully renovated 5-bedroom, 6-bath home blends modern design with effortless everyday living. From the moment you enter, fresh, sophisticated interiors set the tone for a turnkey lifestyle. The spacious eat-in kitchen with a large center island flows into inviting gathering spaces designed for both daily living and entertaining. The cathedral-ceiling primary suite features a gas fireplace, radiant heated bathroom floors, a walk-in closet, and a luxurious bath. Large secondary bedrooms include one en-suite, while a first-floor bedroom with private bath offers flexibility for guests or a home office. A finished lower level provides space for play, fitness, or work. A generous screened-in porch invites summer dinners and relaxed evenings overlooking the property's beautiful grounds and water views. Outside, sweeping level lawns framed by mature trees create a private, park-like setting with exceptional space for recreation, entertaining, and play. An attached a

Clark House, a legacy property with extraordinary provenance, was reimagined by design legends Delphine and Reed Krakoff, adding their imprimatur of spare modern elegance. Reminiscent of a French hunting lodge, the property was purchased by copper heiress Huguette Clark as a country house. The volume of the rooms, windows, and quality of light create a sense of serenity and openness. Stately yet modern, this is a house that can be lived in with comfort and ease. Off the dining room is a walled garden and custom pavilion for entertaining. The 52 acres were transformed with noted landscape architect Perry Guillot into a private park with a great lawn, woodland trails and streams. A new pool and tennis court were added. Twin cottages are gym and caretaker. This caliber of property is a rarity. Caretaker cottage: 1096 sq ft, two bedrooms Gym:1296 sqft * The property had a since reversed 10 lot subdivision when purchased indicating potential for pool house or guest house structures.* Additi