luxury houses for sale South Central Connecticut Planning Region, United States

Commanding Long Island Sound views make this stunning Woodmont home feel like direct waterfront! Located just one house from the sandy beach, this spacious contemporary home offers over 4,000 square feet of living space with three bedrooms, four full bathrooms, and multiple flexible spaces that can be customized to suit your needs. The entire home has been beautifully remodeled, with recently installed structural beams creating a bright, open floor plan that is perfect for everyday living and entertaining. All bathrooms have been completely renovated, and new stonework enhances the front exterior and curb appeal. Enjoy spectacular water views from nearly every room, along with easy access to the beach and scenic shoreline walkway. Conveniently located just minutes from downtown Milford, the train station, shopping, restaurants, and major highways. A special opportunity to experience the very best of coastal living in Milford.

Welcome to one of Connecticut's most desirable waterfront communities. Pine Orchard blends waterfront recreation, country club access, historic coastal character and a relaxed luxury lifestyle. For generations, families have been drawn to this unique shoreline community for its natural beauty and convenient access to New York & Boston. 60 Island View with a contemporary open floor plan concept to ensure panoramic water views from just about every room. Scenic vista views of the famed Stony Creek Thimble Islands, Long Island Sound, Pine Orchard Yacht & Country Club will always be for your viewing pleasure. Nautical light house feature with sweeping staircase will greet you upon arrival as you pull into your oversized garage perfect for cars, truck or golf cart. A full workshop & storage area will ensure you are never out of space. Main floor living area provides maximum flexibility for living, working & entertaining. Each room with water views more breathtaking than the next. With the heart of the home being your custom dream kitchen with handmade cabinetry from Craft Maid, Majestic natural gas range, Sub Zero refrigerator, Miele double oven & dishwasher. Multiple wet bars & butler pantry will keep friends & family gathering at your home for years to come. Second floor consists of a primary bedroom suite with a full wall of glass that places you in one of the most beautiful settings on the Connecticut shoreline.

NEW ROOF to be installed Fall 2026! Enjoy peace of mind with a brand-new roof being installed by the sellers. Perfectly sited on 2.75 private acres overlooking a sweeping lawn, this distinguished Georgian Revival home makes an unforgettable first impression, approached by a circular driveway that creates a true sense of arrival. Newly painted interiors and enhanced landscaping complement the home's timeless elegance. Once a Connecticut Designer Showhouse, the property blends sophistication with remarkable comfort across more than 5,200 square feet. A grand foyer with dramatic staircase introduces generously scaled rooms, 10-foot ceilings, and five fireplaces. The renovated kitchen features today's most desired amenities, including a large center island and butler's pantry, ideal for effortless entertaining. Distinctive architectural details add character throughout, including a remarkable office fireplace mantel reclaimed from a Newport mansion. The spacious bedroom level offers comfort, privacy, and flexibility, highlighted by a luxurious primary suite with renovated ensuite bath and separate dressing room. The home also offers natural gas, new well equipment, and a new septic system. Minutes from the Guilford Green, boutique shopping, and renowned restaurants, this exceptional offering seamlessly combines timeless design, character, and an extraordinary setting.

Experience shoreline living at its finest in this beautifully updated home offering breathtaking 180-degree water views. The home features a light and bright kitchen with stainless steel appliances and blends modern updates with timeless coastal charm. The well-designed floor plan features spacious, light-filled rooms with a natural flow, while walls of windows frame and showcase the incredible water views throughout. A welcoming covered front porch with beautiful mahogany decking provides the perfect spot to relax and take in the coastal surroundings. Step outside to your private backyard retreat featuring an inground pool, stunning bluestone patio, and plenty of space for relaxing or entertaining against a picturesque Long Island Sound backdrop. A finished lower level offers potential for an in-law setup, adding valuable flexibility to the home. Whether enjoying your morning coffee on the front porch or unwinding by the pool overlooking the water, this home delivers the perfect coastal lifestyle. Ideally located just minutes from Milford's beaches, downtown restaurants and shops, the train station, and major highways, this exceptional property offers the perfect blend of tranquility, convenience, and modern living.

Offered Fully Furnished. Set within nearly three private acres of mature woodland, Winnick Retreat is a reimagined mid-century modern residence where architecture, landscape and everyday life exist in quiet balance. Originally built in 1962 designed by Yale's very own Herbert S. Newman, the home is defined by its low horizontal profile, deep roof planes, clerestory windows and expansive walls of glass. A dramatic two-story central atrium draws natural light through the interior, while nearly every principal room maintains a direct visual connection to the surrounding trees, gardens and changing seasons.Inside, approximately 4,134 square feet of living space offers four bedrooms and three-and-one-half bathrooms. Warm wood, natural stone and glass create interiors that feel composed rather than formal. The renovated primary suite, custom kitchen and carefully updated living spaces respect the home's architectural character while supporting contemporary life.nnThe property's recent transformation extends far beyond the interior. Landscaped grounds now unfold as a sequence of private experiences: a swimming pool with fire and water features, pool cabana, barrel sauna, fire-pit courtyard, outdoor fireplace and Har-Tru tennis court. Terraces, balconies and garden paths connect living spaces to the natural setting.nnRecreation and restoration become part of the daily rhythm. Mornings begin with a warm drink on the balcony underneath the tree canopy. Afternoons move easily between tennis, swimming and the sauna. Evenings gather around fire, surrounded by illuminated gardens and the warm glow of the house through glass.nnDespite its extensive amenities, Winnick Retreat's architecture remains the organizing force. The dark exterior recedes into the woodland, while the interiors open toward light, greenery and sky. Every addition has been designed to reinforce the relationship between the house and its setting.nnOffering something increasingly rare: privacy without disconnection, architectural character without compromise, and a fully realized environment that cannot be replicated. It is not simply a collection of rooms and amenities, but a private modernist world shaped for art, wellness, gathering and a more intentional way of living.nnNamed in recognition of the Winnick family, whose stewardship forms part of the home's architectural history.

Development Opportunity - Approved 5-Home Project Rare opportunity for builders, developers, and investors! This offering includes four approved building lots plus an existing single-family residence, creating the potential for a total of five homes. The owners have obtained subdivision approval from the town, and the approved site plan is available in the attached documents, allowing a builder to move forward with development. Included in the sale is an existing income-producing single-family home, currently leased through April 30, 2028, providing immediate rental revenue while development plans are executed. An exceptional investment opportunity with approvals in place, development potential, and built-in cash flow from the existing residence. Existing Home is a 10 Room, 4 Bedroom, 2.5 Bath Colonial with Lots of Room For Everyone! Main Level Features a Welcoming Foyer with Formal Dining Room, Living Room with a Woodburning Fireplace, First Floor Family Room with Entry Door to Outside (Perfect if You Have a Home Business), Library, Half Bath, Eat In Kitchen with an Adorable Breakfast Nook, First Floor Laundry and a Two Car Attached Garage with Entry Into Your Laundry Room. Second Floor Features Four Bedrooms with Two Full Bathrooms and a Walk Up Attic. Oil Hot Water Heat, Private Well and Septic. Features a Rolling Front Lawn with a Circular Driveway.

Historic gem on the Madison Village Green. Once known as Hartsbourne, this storied Madison residence is celebrated for its premier location overlooking the town green and its timeless architectural presence. A true local landmark, the home is distinguished by its striking curved eaved roofline, reminiscent of a pagoda with a unique flat seamed copper roof center. Beautifully aligned with the neighboring Congregational Church, the home shares architectural harmony through its grand columns and elegant two-story shutters. The architect, Mr. Volney Pierce, was commissioned to design this exceptional residence and later the Congregational Church. Inside, the home offers more than 3,900 square feet of living space with soaring 9+ foot ceilings on the main level, 2nd floor with five generously sized bedrooms, five working fireplaces, and the 3rd floor a uniquely large attic with unlimited possibilities. At the back of the property are the outbuildings, a 3 car garage and small coop/shed. Hartsbourne, has abundant historic character throughout. Set on 1.5+ acres in the heart of Madison's charming village, this is a rare opportunity to own a true piece of local history.

A truly unforgettable and exceptionally rare offering-Rogers Island presents an exciting opportunity to own a private island paired with a mainland residence, delivering the perfect balance of seclusion and convenience. The mainland property includes its own dock, parking, and support space, making access to the island with a 5-minute boat ride, seamless and effortless. Just offshore, the island unfolds into a peaceful, panoramic retreat surrounded by water views in every direction. Designed for both relaxation and entertaining, the estate features a 10-bedroom main residence with 6 full and 2 half baths, a 4-bedroom/2.5 bathroom guest house, artist's studio with half bath, and dedicated staff quarters. A mahogany wraparound porch invites you to take in the scenery, while meandering granite pathways guide you thru the grounds which offer an exceptional collection of amenities: an in-ground heated pool with pool house and separate bath house, tennis court, Nicklaus-designed putting green, koi pond, greenhouse and two docks. A charming gazebo sits at the edge of the property-perfectly positioned to capture sweeping views for miles. Quiet, expansive and thoughtfully designed, Rogers Island is a legacy property where generations can gather with ease, hosting everything from intimate weekends to large-scale entertaining, all set against a backdrop of uninterrupted water views, timeless coastal beauty and a sense of privacy that's increasingly impossible to find.

Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa & Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

Experience the opportunity to build a beautifully crafted new construction home by Olsen Built Homes, ideally located in the award-winning Amity school district. Designed with timeless appeal and quality craftsmanship, this five-bedroom residence offers a thoughtful balance of elegance, comfort, and modern living. The home features a bright, open main living area with high ceilings and abundant natural light, creating an inviting space for everyday living and entertaining. Quality finishes and attention to detail are evident throughout, from the well-appointed kitchen to the refined interior trim and flooring selections. With five bedrooms and four and a half baths, the layout provides flexibility for a variety of living arrangements. Set on a 1.40-acre open lot, the property offers ample outdoor space to relax, entertain, or enjoy the surrounding setting. A rare opportunity to customize a new home built with care, craftsmanship, and the trusted quality of Olsen Built Homes in a highly desirable location.