426 houses for sale in Winnipauk

Timeless elegance meets modern comfort in this stunning 1936 brick Colonial, beautifully updated while preserving the warmth, character, and craftsmanship of its vintage roots. Set in one of Westport's most desirable coastal locations, this 5-bedroom, 4.5-bath antique home is filled with architectural detail and storybook charm at every turn. Graceful arched doorways, a curved staircase, detailed moldings, leaded decorative windows, cozy window seats, original crystal and brass hardware, and three fireplaces create an atmosphere that feels both refined and deeply welcoming. Each room has been thoughtfully refreshed with an eye toward comfort, function, and timeless style, while honoring the home's original soul. Outdoor living is equally inviting, with lovely gardens, a spacious patio, a built-in grill, and a firepit perfect for relaxed evenings under the stars. Enjoy an exceptional Westport lifestyle just moments from Compo Beach, Longshore Club, the train, and Saugatuck's beloved res

Two townhouse style units with open floor plans, 2 car garages and additional exterior parking. built in 2007. HW floors, large bedrooms, generous size living rooms. HVAC and laundry in each unit

Better than new, this pristine 2016 custom-built residence offers a rare standard of refinement and sophisticated excellence. With 4,000+sqft and an elevator accessing all four finished levels, the home blends modern architecture with beautifully executed transitional design. The open-concept main level features a magnificent chef's kitchen, spacious dining area, and expansive living room with gas fireplace, custom built-ins, beams, and tray ceiling. Four-inch white oak flooring runs throughout. A wall of glass doors opens to a breathtaking private setting with a remote-controlled awning, ideal for effortless indoor/outdoor living. Four bedrooms include the luxurious primary suite with tray ceiling, built-ins, and serene garden views, plus a spa-like bath with heated floors, soaking tub, double vanity, and walk-in closets. Two additional en-suite BRs and an exceptional home office with dual built-in desks, double-height bookcases, library ladder, and automated shade complete the level.

Set in beautiful and historic Silvermine, this classic Colonial Farmhouse offers the rare combination of character, space, and opportunity on 1.29 idyllic acres. Set back off the road, the property enjoys a peaceful setting while remaining just moments from Grey Barns, schools, and major commuting routes. A welcoming front porch introduces interiors that are filled with warmth and natural light. Rich hardwood floors, a striking stone fireplace, and graciously scaled rooms create an inviting atmosphere for both everyday living + entertaining. The formal living and dining rooms flow effortlessly, while the spacious EIK offers generous workspace, room for a center island, and direct access to the rear deck overlooking the private grounds. The 2nd floor features 4 spacious bedrooms, while the entire 3rd level has been thoughtfully transformed into a private primary suite. Skylights, a full bath, generous closet space, and charming architectural details create a peaceful retreat tucked away

Don't miss this opportunity at a new price; seller is offering a $2,000 credit at closing to use for floors or updates. WELCOME to this spacious 2 bedroom townhouse style condo, conveniently located near both the Merritt Parkway and I-95, perfect for commuters. The open concept main level features a large living room with a cozy fireplace, abundant natural light from the oversized windows. Sliding glass doors off the dining/kitchen area lead to a private balcony, creating a perfect space to relax. Both bedrooms are generously sized and offer excellent closet space. Laundry and a half bath are located on the main floor. There is basement space for storage. Each unit has two parking spots and additional parking for guests. Please note this complex has guidelines on income restrictions, call listing agent for question re:this

Fabulous opportunity along the 5 Mile River! Spacious, 4500+SF Custom Contemporary on the border of Darien and New Canaan. Situated on a highly desirable cul-de-sac, with a pillared drive, on 2+ private acres, overlooking the 5 Mile River. Offering unique architectural details and modern flexibility with over 3100+/- SF of 1st floor living and an additional 1300+/- SF on the 2nd floor. Currently configured as a 3 bdrm, 3 bath home that can easily, transform into a 4/5 bdrm, 5 bath home within the existing footprint. Highlights include: Dramatic Cathedral Ceilings, floor to ceiling field stone fireplaces, large 1st floor primary suite (that can function as private in-law quarters), multi-use loft spaces, walls of glass, abundant water and nature views, 5 fireplaces (4 fieldstone and 1 brick), an attached, oversized 2 car garage with loft and bonus outdoor carport, remarkable privacy and a central location with quick easy access to I-95, Merritt Pkwy and the NYC train. A true hidden gem.

Enjoy the ideal waterfront living in the enchanting community of Marvin Beach surrounded by the beauty of Long Island Sound, Gregory Point, Taylor Farm, and the Norwalk Harbor. This amazing 4 bedroom 3 1u002F2 bath Nantucket Style Colonial has been completely remodeled by an established Fairfield County custom builder and designed for indooru002Foutdoor entertaining, extended family, or working from home. With a blend of classic design, timeless appeal, modern upscale amenities, and open concept the home is an ideal haven for creating lasting memories and enjoying nature at it's best. The first floor includes porch access to the formal living room with custom central staircase, powder room, large open gourmet kitchen with with island, formal dining area, and family room. Just a few steps away from the family room is the private great room, mudroom, and 2 car garage. The second floor offers a private primary suite that includes dramatic High ceiling, oversized walk-in closet, en-suite b

FrogPond Estate is a modern Scandinavian masterpiece unlike anything New Canaan has ever seen. An architecturally rare achievement set on 2.25 pristine, private acres, moments from the train and village. Spanning 11,836 plus square feet of sleek, sun-drenched living space, this 7-bedroom, nine-and-a-half-bath residence is defined by its 12-foot ceilings, bespoke millwork, and designer lighting. Details that elevate every room into something memorable. Four thoughtfully placed laundry rooms, multiple fireplaces, and a fully custom build throughout speak to a level of intentionality rarely found at any price point. At the heart of the main level, a gourmet kitchen with double islands anchors an open floor plan crafted for both quiet daily living and effortless large-scale entertaining. Walls of glass dissolve the boundary between inside and out, opening to covered porches and private balconies that complete the estate's serene, Scandinavian sensibility. A separate 1,190 sq. Ft. guest cot

New lower price. Welcome home to the Gold Coast of Norwalk. Location, space and timeless design come together in this stunning turn-key colonial with waterviews of Long Island Sound. Set on one acre in Norwalk's coveted Shorehaven neighborhood, it's just a short walk to Sandy Beach and the Sprite Island Yacht Club boat launch. Custom features and 10-foot ceilings elevate the main level and make it ideal for both everyday living and entertaining. The family room flows seamlessly into the eat-in kitchen. A generous deck overlooking the backyard is perfect for relaxing or hosting friends. The first floor private office with full bath also serves as a guest bedroom. Upstairs, the primary bedroom features a fireplace and a sumptuous bath that opens to an outdoor deck. The third floor offers an entertainment center with full bath and an additional office space. New additions include a full house generator, outdoor lighting, a fire pit and patio. Nearby is the Shorehaven Country Club as well

Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a remarkable archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to a quieter, more adventurous relationship with the coast. Rich in maritime history and surrounded by protected waters, portions of the island chain are preserved within the Stewart B. McKinney National Wildlife Refuge, helping maintain the natural beauty, wildlife, and sense of escape that define this rare envir

Introducing an exceptional new build from Simple Plan Home Builders, multiple HOBI Award winners known for iconic Westport homes. Just a short stroll to Compo Beach, this striking modern coastal retreat is privately set on a coveted cul-de-sac, blending luxury, light, and effortless living. Spanning four levels, this six-bedroom home features an airy layout with refined finishes throughout. The open-concept kitchen flows seamlessly into the main living spaces, highlighted by a statement fireplace. A glass-enclosed office offers privacy, while additional living and dining areas, a stylish scullery, and an oversized mudroom add everyday functionality. A dramatic pivot door opens to a gallery-style entry. Upstairs, the primary suite is a serene retreat with its own fireplace, dual walk-in closets, a dressing area, and a spa-like bath. Four en-suite bedrooms and a laundry room complete the second floor, while the top level offers a private sixth suite, office, and flexible open spaces. The

Beautiful Colonial built in 2005 with 4 bedrooms, 2.5 baths, abundant storage, and excellent potential for an in-law suite. Designed for both everyday living and entertaining, this sun-filled home features hardwood floors, central air, natural gas heat, and an open floor plan. The welcoming main level offers a spacious living room, formal dining room, and an expansive family room with a cozy gas fireplace. The updated eat-in kitchen features ample cabinetry, generous counter space, and direct access to an oversized Trex deck overlooking the fully fenced backyard-perfect for outdoor dining, entertaining, or relaxing. Upstairs, the impressive primary suite provides a peaceful retreat with a walk-in closet and a private bath featuring a Jacuzzi tub. Three additional generously sized bedrooms, a full hall bath, and the convenience of a second-floor laundry room complete this level. The finished third floor offers exceptional flexibility, making it ideal as a playroom, media room, home offi

Opportunities like this are rare. Calf Pasture Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a blank canvas for imagination. Properties like this remain in the same hands for many decades and do not come up for sale often. Located approximately a half mile offshore, it is among the closest islands to the mainland and takes its name from the cattle once kept there. The island is easily accessible from Norwalk Harbor and the Saugatuck River, making it a convenient yet distinctly separate retreat. A small A-frame structure currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a rare archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to life just beyond the shoreline. Rich in maritime history and surrounded by protected waters, portions of the islan

Opportunities like this are exceedingly rare. Betts Island is one of just 10 private islands off the coast of Norwalk, offering a uniquely private coastal setting and a canvas for imagination. Located approximately one mile offshore, the island is distinguished by its natural land bridge, which connects its two halves and creates a protected cove long favored by boaters. A small bungalow currently sits on the island, and future development options may be explored. Shaped by retreating glaciers more than 17,000 years ago, the Norwalk Islands form a remarkable archipelago scattered across Long Island Sound. For generations, they have attracted boaters, kayakers, and those drawn to a quieter, more adventurous relationship with the coast. Rich in maritime history and surrounded by protected waters, portions of the island chain are preserved within the Stewart B. McKinney National Wildlife Refuge, helping maintain the natural beauty, wildlife, and sense of escape that define this rare envir

New construction by renowned luxury builder mattera construction. Steps to compo beach! A rare opportunity to own a brand-new, architecturally refined home in one of Westport's most coveted coastal locations-just steps to Compo Beach, Longshore Club, downtown Westport, the train, and schools. Currently under construction, this impeccably designed 6-bedroom residence spans four finished levels and blends timeless elegance with modern living. The main level offers light-filled, open living spaces ideal for both everyday living and entertaining, featuring a custom chef's kitchen with breakfast area, expansive family room, formal living and dining rooms, private office, mudroom, and thoughtfully placed powder rooms. The second level showcases a luxurious primary suite with two generous walk-in closets and a spa-inspired bath, along with four additional ensuite bedrooms and a dedicated laundry room. The walk-out lower level includes a spacious recreation room, gym, guest bedroom with full b

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

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 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