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

Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight lines, anchored by a massive family room and a top of the line chef's kitchen. The lower level is a true walkout guest suite with additional living space plus a separate garage apartment for overnight guests. Outside amenities evoke a private resort: a gunite pool, extensive stone patios, two fully equipped outdoor kitchens, and a charming grassy area framed by mature landscaping for complete privacy. This is a rare coastal estate that blends modern, high end finishes with relaxed, year round seaside living. Practical luxury continues with a three car garage, circular driveway, and generous storage. This is truly a must see.

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.

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.

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.