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90 Welch Rd, Southington
$5,400,000
24176184 MLS
An exceptional opportunity for builders, developers, and investors to acquire approximately 23 acres in one of Southington's most rapidly growing locations. Situated within the R-40 residential zone, this expansive parcel offers outstanding potential of a luxury residential subdivision, custom home community, condominium project, or possible active adult 55+ development. The property features valuable road frontage on Welch Road with convenient access near West Pines Drive and Bagno Drive being surrounded by high-end established residential neighborhoods, creating an ideal setting for future development. The land offers a favorable topography with gentle elevation changes and strong accessibility for planning and infrastructure design. Existing ulitiies and nearby amenities further enhance the investment appeal of this rare offering. Conveniently located in sought after Southington near major highways, shopping dining, schools, and recreational amenities while still offering privacy and a picturesque natural setting. (This property is residential zoning but has been used as farmland and has large amounts of rich topsoil.)

90 Welch Rd, Southington

55-57 Brinton Hill Rd, Salisbury
$5,375,000
4 Beds ⋅ 3 Baths ⋅ 24206034 MLS
Renegade Farm is a breathtaking 85+ acre luxury countryside estate where the romance of farm-to-table living meets the indulgence of a private resort. The sprawling grounds feature a beautifully appointed 4-bedroom main house(4,504 sq ft) & a completely separate, spacious 4-bedroom guest house(4,074 sq.ft) making it an unmatched haven for multi-generational gatherings and high-end entertaining. The Main house features a dreamy chef's kitchen with mountain views, wood-burning fireplaces in the living room and family room are among many of the home's special attributes. The guest house is almost identical in size to the main house and also boasts two wood-burning fireplaces-one in the living room and the other in the family/recreational room-and two kitchens, one on each floor. Both homes enjoy large screened-in porches and outdoor courtyards, and total privacy between the 2 homes. Outside, a large garden retreat offers a true estate lifestyle, while wide, manicured trails wind through the vast acreage to reveal stunning, panoramic mountain views. The property includes a custom gunite pool, a newly resurfaced private tennis court, and a large fruit and vegetable garden. Renegade Farm is more than just a property; it is a magical, self-contained oasis designed for absolute privacy, active leisure, and serene natural beauty. Nearby - Catamount & Butternut, private & public schools, Twin Lakes & Lakeville Lake, and charming towns of Lakeville, Salisbury,Sharon & Great Barrington

55-57 Brinton Hill Rd, Salisbury

Kent
$5,250,000
24201971 MLS
The rarest luxury is seldom the land itself. It is the time already devoted to revealing its full potential. Set amidst protected land along the coveted Kent-Sharon border, RockOak offers the uncommon advantage of beginning years ahead on the construction of a legacy estate. The completed retreat allows the property to be enjoyed immediately, while the future estate evolves. Overlooking the orchard, gardens, woodlands and long views it offers refined, comfortable living from the very first day. The estate unfolds like a private park of meadows, woodlands, orchards, gardens, dramatic elevations and a sheltered seasonal brook. Sweeping western sunsets, expansive northern vistas, and carefully composed landscapes ensure every season reveals a new perspective. Two parcels define the property's flexibility. The principal Sharon homesite occupies a commanding elevation and includes architectural design plans by architect, Scot Samuelson, AIA, NCARB for a 5,000+ sq ft residence. The 2nd parcel is in Kent & Sharon, reached by its own private drive. It rests quietly on the edge of a woodland above the brook and in the meadow below the principal Sharon site. Throughout the estate, thoughtful infrastructure has been integrated into the landscape, while historic woodland roads, stone walls, specimen trees, perennial gardens, fountains, scenic overlooks, and a distinctive 40 tree orchard create a landscape of exceptional beauty and permanence. Convenient access to NYC by car or train.

Kent

Sharon
$5,250,000
2 Beds ⋅ 2 Baths ⋅ 24201909 MLS
The rarest luxury is seldom the land itself. It is the time already devoted to revealing its full potential. Set amidst protected land along the coveted Kent-Sharon border, RockOak offers the uncommon advantage of beginning years ahead on the construction of a legacy estate. The completed retreat allows the property to be enjoyed immediately, while the future estate evolves. Overlooking the orchard, gardens, woodlands and long views it offers refined, comfortable living from the very first day. The estate unfolds like a private park of meadows, woodlands, orchards, gardens, dramatic elevations and a sheltered seasonal brook. Sweeping western sunsets, expansive northern vistas, and carefully composed landscapes ensure every season reveals a new perspective. Two parcels define the property's flexibility. The principal Sharon homesite occupies a commanding elevation and includes architectural design plans by architect, Scot Samuelson, AIA, NCARB for a 5,000+ sq ft residence. The 2nd parcel is in Kent & Sharon, reached by its own private drive. It rests quietly on the edge of a woodland above the brook and in the meadow below the principal Sharon site. Throughout the estate, thoughtful infrastructure has been integrated into the landscape, while historic woodland roads, stone walls, specimen trees, perennial gardens, fountains, scenic overlooks, and a distinctive 40 tree orchard create a landscape of exceptional beauty and permanence. Convenient access to NYC by car or train.

Sharon

31 Stonybrook Rd, Westport
$5,199,000
5 Beds ⋅ 8 Baths ⋅ 24201547 MLS
From the moment you enter the gates of this Old Hill estate, you know you've arrived- a rare sanctuary built with a level of custom stonework and craftsmanship impossible to replicate today. This stunning 5 bedroom, 6.2 bath home offers an extraordinary blend of elegance, privacy, and nature. Set in a mature landscape that takes generations to establish, the setting delivers unmatched wildlife views-from herons and owls to ducks and otters along picturesque Stony Brook. Resort-style amenities feature a heated saltwater pool/spa, a private pond with a fountain, and deeded access to nearby Nash's Pond for kayaking and fishing. Inside, a dramatic wall of glass captures sweeping water views, creating a seamless connection to the outdoors. The main level includes a gourmet kitchen, family room with fireplace, dining room with wet bar, living room with fireplace and lounge, stone entry foyer, mudroom and two powder rooms. Upstairs, the primary suite boasts two terraces, dual walk-in closets, and a spa bath. Four additional bedrooms each with its own bathroom, a sprawling home office/6th bedroom with fireplace, a large playroom with a full bath, a third floor family room, and a mirrored gym/yoga studio with a ballet barre offer exceptional living options. Moments from Earthplace nature trails, key features include a heated 3-car garage, Crestron lighting, full-house generator, and a built-in poolside gas grill. A rare opportunity to own a sanctuary where design and nature converge.

31 Stonybrook Rd, Westport

25 Adams Ln, New Canaan
$5,195,000
6 Beds ⋅ 8 Baths ⋅ 24197551 MLS
On one of New Canaan's most coveted streets, 25 Adams Lane stands as a rare offering: exceptional architecture, extraordinary amenities, and the kind of warmth that cannot be built - only lived. Set on two glorious south-facing acres, the property commands one of the finest front lawns in town; a sweeping, softly grassed acre framed by mature flowering trees, and longtime home to the neighborhood's beloved annual Turkey Bowl. The fully enclosed backyard, bordered by a gently running creek and cathedral of mature trees, delivers the privacy of a country estate within one of New Canaan's most beloved neighborhoods. This spacious residence offers six bedrooms, six full and two half baths across four thoughtfully designed levels. Step inside to soaring 9-foot ceilings, extensive custom millwork, and windows positioned to flood every room with southern light. The open-plan kitchen anchored by two large islands and appointed with Sub-Zero, Wolf, and Thermador, rises to every occasion. Five fireplaces warm the principal gathering spaces, including a handsome paneled study ideal for working from home. The primary suite features a fully custom dressing room and stunning new bath (2025). A private sitting room with three walls of windows, suspended among the treetops, redefines what a home office can be. The finished third floor serves as playroom, studio, or guest quarters. The lower level delivers a nine-seat home theater, well-appointed gym, and wine cellar.

25 Adams Ln, New Canaan

56 W Morris Rd, Washington
$5,195,000
8 Beds ⋅ 9 Baths ⋅ 24182442 MLS
West Winds is one of Washington's most extraordinary country estates, offering an unparalleled combination of privacy, natural beauty, recreation, and equestrian amenities. A long, winding drive meanders through expansive meadows and orchards, culminating at a remarkable 10,000+ square-foot barn-style residence. Meticulously crafted using reclaimed beams and siding from a 19th-century Dutch barn, the home blends authentic historic character with modern comfort and scale. Set on 62 acres across 4 separate parcels, the property enjoys over 1,000 feet of frontage along the Bantam River, with sweeping views across the water to the mountains beyond (including iconic Mt. Tom). Outdoor amenities are exceptional, highlighted by a spectacular infinity-edge pool surrounded by stone terraces and walls, a private pond for fishing and winter skating, and direct access to miles of protected land trust trails ideal for hiking, biking, horseback riding, and exploring the surrounding countryside. For equestrian enthusiasts, West Winds offers a rare opportunity to ride directly from the property onto adjacent trail networks that follow the scenic Bantam River. The horse facility includes 4 stalls, tack area, and paddocks creating a turnkey setup for both recreational and serious riders. The heart of the home is the renovated eat-in kitchen, ideally positioned between the dramatic vaulted great room and the expansive media/game room.

56 W Morris Rd, Washington

32 Broadway Ave, Stonington
$5,050,000
6 Beds ⋅ 6 Baths ⋅ 24185056 MLS
Rarely does a commercial asset of this caliber become available in the historic heart of downtown Mystic. Located just 0.1 miles from the Mystic Amtrak Station, this turnkey property offers direct, car-free transit to travelers from NYC and Boston. It presents an unmatched opportunity for a boutique hotel operator, short-term rental (STR) investor, or residential developer. Located in the LS-5 zone, it is pre-zoned for hospitality/hotel use, allowing immediate STR or hotel operations. Luxury accommodations and fully furnished with a rooftop oasis with communal sun lounge, dining area, and dip pool with panoramic townscape views. Modern construction, individual high-efficiency climate zones, public utilities, and a dedicated 10-13 car paved off street parking lot allow ease and comfort. Centrally located in one of New England's most desirable, rapidly appreciating coastal destinations. Qualified private showings by appointment only. Also listed as Commercial under MLS# 24184137

32 Broadway Ave, Stonington

32 Broadway Ave, Stonington
$5,050,000
1 Baths ⋅ 24184137 MLS
Rarely does a commercial asset of this caliber become available in the historic heart of downtown Mystic. Located just 0.1 miles from the Mystic Amtrak Station, this turnkey property offers direct, car-free transit to travelers from NYC and Boston. It presents an unmatched opportunity for a boutique hotel operator, short-term rental (STR) investor, or residential developer. Located in the LS-5 zone, it is pre-zoned for hospitality/hotel use, allowing immediate STR or hotel operations. Luxury accommodations and fully furnished with a rooftop oasis with communal sun lounge, dining area, and dip pool with panoramic townscape views. Modern construction, individual high-efficiency climate zones, public utilities, and a dedicated 10-13 car paved off street parking lot provide allow ease and comfort. Centrally located in one of New England's most desirable, rapidly appreciating coastal destinations. Qualified private showings by appointment only.

32 Broadway Ave, Stonington

6 Berry Ln, Darien
$5,025,000
6 Beds ⋅ 3 Baths ⋅ 24213301 MLS
There is a rare kind of magic when classic architecture meets a modern, artistic eye. Privately tucked at the end of a quiet cul-de-sac in Tokeneke School District. This stunning six-bedroom center-hall Colonial is surrounded by extraordinary grounds reminiscent of a private botanical garden. Mature specimen trees, sculpted greenery, flowering perennials and winding bluestone pathways create a breathtaking landscape in every season. Inside, sophisticated interiors blend timeless elegance with modern style. Sun-filled rooms, oversized windows, bespoke finishes and designer outdoor lighting frame spectacular garden views throughout. A beautifully remodeled eat-in kitchen serves as the heart of the home, flowing effortlessly into gracious living and entertaining spaces. Outdoors, an infinity-edge gunite pool and spa take center stage, surrounded by expansive bluestone terraces for dining, lounging and entertaining. A dedicated fire pit gathering area adds another enchanting dimension to this remarkable setting. Lush, mature landscaping provides exceptional privacy, creating a true resort-like retreat. Steps from Five Mile River, Rowayton and coastal Darien, this extraordinary property offers the perfect marriage of classic architecture, sophisticated design and unforgettable indoor-outdoor living. An exceptional property with the added luxury of flexibility, offering generous possibilities for future expansion.

6 Berry Ln, Darien

118 River Rd, Madison
$5,000,000
3 Beds ⋅ 3 Baths ⋅ 24192754 MLS
Some properties are defined by the house that sits on them. Others are defined by the land itself...by history, landscape and a sense of beauty that simply cannot be created. This is such a place. Owned and farmed by the same family for 200 years, this remarkable 16 Acre piece sitting on the Hammonassett River is the last piece of the original farm to be sold. With over 1500 ft. bordering the river, the property unfolds across open hay fields, tidal marshes and expansive river views. The landscape changes with the seasons and the light, grasses moving with the wind and water reflecting the ever changing sky...a landscape that is both bucolic and breathtaking. This is an exceptional setting for a distinctive country residence, a private retreat or a place to enjoy a quieter chapter of life. An existing, well appointed, three bedroom ranch home sits on the property and enjoys the same remarkable views. Comfortable as it stands, the home could ultimately serve as a guest house, artist's studio or private office. The property offers the potential for more than one lot, but with generations of family ownership, the sellers have hopes to see the land remain intact, so no soil testing has been undertaken for subdivision. A survey is available and buyers considering additional development should conduct their own due diligence. After two centuries in the same family, this is a rare opportunity to become the next steward of an extraordinary Connecticut landscape.

118 River Rd, Madison

119 High Rock Rd, Groton
$5,000,000
24134100 MLS
Exceptional opportunity to acquire 5 contiguous parcels totaling 46+/- acres in a sought-after industrial zone just minutes from the Groton/New London Airport. This rare offering presents endless potential for large-scale development in a high-visibility, high-traffic location. The property supports a wide range of development possibilities, including agricultural uses, campground, commercial facilities, entertainment or sports facilities, and so much more. With convenient access to major highways and transportation routes, this site is ideally positioned for local and regional business growth. Utilities are available nearby, and the expansive acreage provides flexibility for phased or large-scale projects. Whether you are a developer, investor or business owner seeking a strategic location, this property offers unmatched potential and prime positioning.

119 High Rock Rd, Groton

19 Orchard Ln, New Canaan
$4,999,999
6 Beds ⋅ 8 Baths ⋅ 24206656 MLS
THIS IS THE ONE YOU'VE BEEN WAITING FOR! Under constuction very close to completion. Brand new construction opportunity by highly regarded Lecher Development, on a prime, quiet in-town cul-de-sac. This exceptional luxury home offers 8000 + SF of high quality finishes, light-filled, living space across four finished levels. Highlights include: Gourmet Kitchen: A state-of-the-art kitchen featuring a large center island, premium stainless steel appliances, and an open layout that flows seamlessly into the family room with a fireplace and French doors leading to a covered porch. Flexible Main-Level Living: The first floor includes a private main floor space that can serve as a home office or sixth bedroom, complete with a full bath. Finished Third Floor: Ideal for a second office, playroom, guest suite, or au pair quarters. Spacious Lower Level: Featuring 10-foot ceilings, full bath, plenty of options to crate the perfect gym, media room, playroom, or additional recreation space. Generous Ceiling Heights: 9-foot ceilings on the main and second floors enhance the home's open, airy feel. Additional amenities include a 24-kW generator, five-zone heating and cooling, town water and gas. Set on a level property with a designated pool site, this home combines luxury, comfort, and customization in an unbeatable location. Don't miss the opportunity to make this exceptional property your dream home

19 Orchard Ln, New Canaan

48 Old Farm Rd, Wilton
$4,999,999
5 Beds ⋅ 8 Baths ⋅ 24170471 MLS
Set beyond stone walls and a landscaped entrance, 48 Old Farm Road is a newly completed Wilton residence blending timeless New England architecture with a bright, refined modern interior. The open central hall makes an immediate impression with pale oak floors, abundant natural light and a striking staircase with black metal balusters. Generously proportioned living spaces feature custom millwork, expansive windows and seamless flow for everyday living and entertaining. The kitchen opens to the main gathering areas and overlooks the rear grounds. Spacious bedrooms include vaulted ceilings, large windows and beautifully finished baths with stone surfaces, frameless glass showers and thoughtfully selected fixtures. An elevator adds convenience between levels, while the three-car garage, broad driveway and multiple covered outdoor areas enhance daily function. Mature trees, open lawn, stonework and a private setting create the feel of a composed country property. The detached 2000 sq. ft. accessory building ready to be finished. Room for a pool. Served by Wilton Public Schools and convenient to Wilton Center, local amenities and Metro-North service to New York City.

48 Old Farm Rd, Wilton

294 Maple Rd, Easton
$4,999,000
5 Beds ⋅ 9 Baths ⋅ 24146882 MLS
A rare offering, this Gambrel shingle-style estate is a sanctuary on over 15 acres with a lake and separate building lot-ideal for equestrian pursuits or a secluded retreat. Crafted with no expense spared, the residence features steel construction, geothermal energy, cedar roofing and siding, and copper gutters. Inside, an elevator connects all levels, while quarter sawn wide plank hardwood floors, custom window treatments and coffered ceilings elevate the space. At the heart of the home, a stunning marble kitchen outfitted with Subzero and Wolf appliances, a breakfast nook, and butler's pantry opens to a soaring two-story family room as well as formal dining and living rooms for effortless entertaining. A main level bedroom suite is ideal for guests. Two private offices and well appointed mudroom enhance everyday functionality, while four fireplaces add warmth to the home. Upstairs, a spectacular primary suite with balcony, and 3 additional ensuite bedrooms are accompanied by a spacious bonus room with adjoining craft room. Intricate millwork and custom built-ins enrich every inch of this special home, reflecting its master craftsmanship. Wraparound covered patios overlook the saltwater Gunite pool, while an outdoor kitchen and fire pit invites alfresco dining. Pool house with kitchenette, laundry, 2 baths, rec room with balcony is perfect for guests. Five garage bays for the car enthusiast. The property offers unmatched luxury. Quite simply, there is nothing else like it.

294 Maple Rd, Easton

8 Bouton Ln, Darien
$4,995,000
6 Beds ⋅ 6 Baths ⋅ 24212918 MLS
Experience the pinnacle of modern luxury at 8 Bouton Lane, a masterful new construction that sets a new benchmark for craftsmanship in Darien. Every inch of this residence reflects an uncompromising commitment to quality, from the soaring nine-foot ceilings on the main level to the intricate millwork and exquisite waist-high paneling that graces the formal dining and living rooms. At the heart of the home, a chef's dream kitchen awaits, equipped with top of the line appliances, centered around an expansive island w/ample seating. The open flow leads seamlessly into inviting spaces anchored by a fireplace in both the living and family rooms, perfect for sophisticated entertaining. The second floor is a sanctuary of comfort, headlined by a sumptuous primary suite. This retreat features a dramatic tray ceiling in primary bath, a private sitting area w/its own gas starter fireplace, dual walk-in closets and floor-to-ceiling wainscoting. The 4 additional spacious bedrooms on this level share two thoughtfully designed Jack&Jill baths. The finished 3rd level, not to be missed, has two rooms with vaulted ceilings, skylights, custom shiplap walls, and a full bath. This flex space can be the 6th bedroom, home office, or any customized use. Not to be outdone, the finished lower level offers nearly 1,000 sq ft featuring a elegant tray ceiling, side paneling, a walk-in cedar closet, and convenient walk-out access. Outside, the large, private bluestone patio provides a serene setting for

8 Bouton Ln, Darien

1716 Shippan Ave, Stamford
$4,995,000
5 Beds ⋅ 5 Baths ⋅ 24195094 MLS
1716 Shippan Avenue represents a rare opportunity to own a legacy estate on 1.01 acres in Stamford's sought-after Shippan neighborhood. This distinguished Tudor home is comprised of approximately 6,000 square feet of timeless architectural character, sophisticated modern updates, and a thoughtfully designed 2016 renovation by Granoff Architects. With 5 bedrooms, 3 full and 2 half baths, the home is rich in detail, including original stained glass, oak paneling, unique solid oak arched interior doors, and three wood-burning fireplaces. Custom millwork, a Vermont slate roof, and new Marvin windows throughout further showcase the home's exceptional craftsmanship. The beautifully updated second-floor bathrooms feature custom cabinetry, bookmatched marble showers and countertops, and heated floors. In addition to generous living and entertaining spaces, the home also includes a finished lower level, a third-floor loft with water views (currently used as a home gym), and a charming attached greenhouse. Outside, a 40' x 20' gunite pool and spa, expansive patio, and mature gardenscape create a picturesque private oasis. Exceptionally private, the expansive grounds made up of 2 parcels provide an idyllic backdrop for sun-filled summer days, evenings spent poolside, and memorable gatherings with family and friends. Enjoy Shippan's waterfront community minutes away from the Stamford Yacht Club, local dining, and the express train to Manhattan.

1716 Shippan Ave, Stamford

238 Hillspoint Rd, Westport
$4,995,000
3 Beds ⋅ 4 Baths ⋅ 24194201 MLS
The dream of waterfront living is officially taking shape-construction is underway by renowned builder The O'Dell Group. This is your chance to secure a front-row seat to the Long Island Sound on one of Westport's most prestigious stretches of coastline. This exceptional property offers direct water frontage + sweeping, uninterrupted views of the Sound + the iconic Old Mill Beach. Imagine waking up to the soft glow of a sunrise over the water, spending your afternoons enjoying the refreshing salt air, or relaxing to the rhythm of the tide. Every detail of this build is designed to maximize the connection to the sea, offering a lifestyle defined by beauty + tranquility. Nestled in a welcoming and picturesque community, you'll enjoy access to top-ranked schools + Westport's vibrant downtown, known for its exceptional dining, shopping, and cultural experiences. Plus, the location is ideal for commuters, with close proximity to Metro-North for a seamless trip to Grand Central Station in NYC. As the last available parcel of its kind for development in this coveted location, this project represents a rare opportunity to own a brand-new architectural masterpiece in an idyllic setting. With The O'Dell Group's signature craftsmanship now in motion, the vision for this ultimate beach house is becoming a reality. Seize the opportunity to claim this piece of paradise and personalize your finishing touches while there is still time. Reach out today to make this coastal sanctuary your own.

238 Hillspoint Rd, Westport

39 Chippechaug Trl, Stonington
$4,995,000
4 Beds ⋅ 5 Baths ⋅ 24172306 MLS
A spectacular waterfront residence on Masons Island, 39 Chippechaug Trail captures the very best of coastal New England living. Set on 2.05 private acres with more than 250 feet of direct waterfront, this custom-built, move-in ready 4,300 square-foot home enjoys sweeping 180-degree water views, a private sandy beach, deep-water access and its own dock all within one of the Mystic/Stonington area's most coveted waterfront settings. Beautifully maintained and thoughtfully positioned to embrace its extraordinary surroundings, the residence offers comfortable, inviting interiors designed to be enjoyed from day one. Expansive windows and water-facing spaces create a natural connection between the home, grounds and shoreline, while mature oaks frame the property with exceptional privacy and an established coastal landscape. Designed for both relaxed everyday living and entertaining, the property transitions effortlessly from the house to expansive lawns, beach and dock. Boating, swimming, kayaking and days on the water begin right outside your door, while the breadth of the property creates a remarkable sense of openness, privacy and connection to the shoreline. A three-car garage and geothermal heating add comfort and functionality, while the private island setting feels worlds away yet remains just minutes from downtown Mystic's acclaimed restaurants, boutiques, marinas and waterfront attractions.

39 Chippechaug Trl, Stonington

1 Coastal Ct, Westport
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 24126503 MLS
Introducing 1 Coastal Court, a rare opportunity to own in Westport's only gated community, an exclusive four-lot enclave envisioned and built by Joe Feinleib, founder of Coastal Luxury Homes and one of Fairfield County's most respected builders.This private neighborhood blends timeless architecture with modern luxury. Each custom residence, ranging from 5,000 to 7,500 square feet, plus generous garages, balconies, patios and covered porches, will be designed in collaboration with the homeowner - ensuring every detail reflects your vision. Expansive layouts, pool sites, and inviting outdoor living spaces create the perfect setting for today's lifestyle, balancing sophistication with everyday comforts. Working with Coastal Luxury Homes is a dynamic, collaborative and easeful process with every detail curated to suit the homeowners' vision of the perfect home. Whether you dream of having your own golf simulator, outdoor chef's kitchen, sauna or elevator...everything is possible. Ideally located just moments from Westport's award-winning schools, vibrant downtown, the train, and Compo Beach, this unique neighborhood offers a rare combination of privacy and convenience. Mature landscaping and thoughtful design create a serene retreat, while the best of dining, shopping, and recreation are just minutes away. This is more than a new home - it's the chance to create your dream residence with an award-winning builder in a community unlike any other in Westport.

1 Coastal Ct, Westport

195 Old South Rd, Fairfield
$4,950,000
4 Beds ⋅ 5 Baths ⋅ 24206984 MLS
Set on 1.25 acres in the heart of historic Southport Village, 195 Old South Road offers something increasingly rare: the character and presence of an 1829 Federal/Greek Revival residence with an unusually expansive yard. Private and surrounded by mature plantings, the 4,254-square-foot home offers four bedrooms, three full and two half baths across three floors. A gracious Front Hall, anchored by a sweeping curved staircase, opens easily to the home's principal rooms. The sun-filled, 30-foot Living Room features 9-foot ceilings and connects to the Dining Room through a passage framed by arched openings and a built-in wet bar. An expansive Family Room/Sunroom is accessible from the Living Room, Dining Room and Kitchen, creating an easy flow for everyday living and entertaining. Three wood-burning fireplaces add warmth and character. The generous Primary Suite features a gas fireplace, dressing room and private bath. A separate Guest Suite, two additional bedrooms and unfinished upper-level space offer flexibility. A substantial historic barn/garage accommodates two cars, with potential for three, and offers a full second floor. A large, level lawn provides remarkable privacy in close proximity to Southport Harbor, Southport Beach and Metro-North. A rare combination of acreage, architectural character and Village location. 195 Old South Road can be enjoyed immediately while offering its next owners the freedom to make the home distinctly their own over time.

195 Old South Rd, Fairfield

19 Davenport Ave, Greenwich
$4,895,000
4 Beds ⋅ 4 Baths ⋅ 24214631 MLS
Completely reimagined by J & S Homes, 19 Davenport offers 3 levels of sophisticated single-family living overlooking Smith Cove, showcasing exceptional quality, craftsmanship and attention to detail throughout. Light-filled interiors feature white oak floors, graceful archways, a linear fireplace and chef's kitchen with Viking appliances. The primary suite opens to a private waterfront deck, while the versatile ground level offers a 4th bedroom/family room with full bath & kitchenette. Three TimberTech decks, James Hardie siding, new roof, Marvin Ultimate windows & sliders, radiant-heated baths and smart entry doors with switchable privacy glass complete this distinctive downtown Greenwich waterfront residence. Concierge property management available for effortless living.

19 Davenport Ave, Greenwich

57 Indian Trail Rd, New Milford
$4,850,000
4 Beds ⋅ 5 Baths ⋅ 24176398 MLS
"Hollow Farm" - An Expansive Historic Estate Reimagined for Modern Country Living Nestled in its own private valley, this 72-acre estate includes a Main House, thoughtfully updated and expanded in 2005; a charming Guest Bungalow; screened Gazebo perched over a pond; Pool Pavilion; Stables with caretaker's apartment; and a restored Barn. Comprised of multiple parcels, offering maximum privacy. The circa-1755 Main House features a dramatic great room with stone fireplace, adjoining chef's kitchen, and formal dining room. Additional main-level spaces include both a sitting room and a library with back-to-back fireplaces, plus a guest suite with full bath and sitting room. Upstairs, the primary suite offers a lofted sitting area with fireplace, as well as private deck, while two guest bedrooms share a hall bath. The lower level includes a wine cellar with cobbled floor and a gym. Outside, multi-level terraces showcase exceptional stonework, a fire pit, grilling area, pool, and spa. Two ponds and the sparkling Merryall Brook enhance the 18 acres of open land. Extensive landscaping compliments the natural beauty of the forested hills. As with the Main House, every outbuilding and outdoor space has been meticulously maintained. Although it feels a world away, this remarkable property is only 15 minutes from Kent, New Preston, and Washington. With its historic character, modern updates and expansive private setting Hollow Farm offers a rare opportunity for refined country living

57 Indian Trail Rd, New Milford

22 Evergreen Ave, Westport
$4,850,000
5 Beds ⋅ 5 Baths ⋅ 24172211 MLS
Introducing The Winslow Manor, one of Westport's most exceptional estates, is a secluded retreat defined by beauty, privacy, and grace, now available for the first time in decades, inviting its next residents to experience the privilege of living within this storied and extraordinary sanctuary. Just steps from downtown & completely remodeled in 2002, welcome home to a rare and timeless estate where classic Arts & Crafts architecture meets the tranquility of a private countryside retreat. Set on over 2.5+ sprawling acres of pristine grounds, this exceptional 5 Bed, 5 Bath residence offers more than 5,100 sqft of refined living, surrounded by natural beauty & complete privacy. From the moment you arrive down the private, meandering drive framed by mature landscaping; The Winslow Manor evokes a sense of warmth, character, and enduring craftsmanship. Rich architectural details, beamed ceilings, inviting living spaces, & thoughtfully designed interiors create a home that feels both grand and deeply welcoming- as if stepping into a piece of cozy history, carefully preserved and elevated for modern living. Designed for both relaxation & recreation, the estate unfolds into an extraordinary outdoor experience. A sparkling Gunite pool, multiple terraces, Pergolas, & dedicated home gym create the ultimate summer retreat, while the surrounding pond and protected wetlands attract an abundance of wildlife, offering peaceful views and a connection to nature rarely found so close town.

22 Evergreen Ave, Westport

1 Twin Oaks Ln, Westport
$4,750,000
5 Beds ⋅ 7 Baths ⋅ 24204438 MLS
A fresh take on Modern Luxury awaits at this new construction home set on stunning property in the Old Hill area of Westport. Now complete and ready for immediate enjoyment, this dynamic residence is perfectly located for convenience to commuting, the train station, schools, shopping and more. Exhilarating architecture will awaken your senses as you approach this customquality home. Walls of glass blend the natural setting with stunning interiors, and bring sunlight deep into the spectacular rooms. The chef's kitchen is a showpiece, featuring bespoke oak cabinetry, premium finishes, and a substantial walkin pantry. Dual mainlevel offices support today's lifestyle. 5 spacious bedrooms and 7 refined baths create a harmonious balance of comfort and sophistication. The primary suite is a serene retreat with three fitted closets and a spalevel ambiance. Additional bedrooms offer generous scale and thoughtful design. A sunlit upstairs lounge and a finished thirdfloor space provide flexible areas for work, play, or creativity. The finished lower level offers exceptional spaces for fitness, media, or entertaining. Outside, an expansive patio overlooks 1.68 acres of private grounds, ideal for gatherings or quiet reflection. A 3car garage (with a separate bay for a trophy vehicle or storage) and sleek modern detailing complete this remarkable offering. An inspired blend of architecture, setting, and convenience await in a prime location. Pool permit in place.

1 Twin Oaks Ln, Westport

90 Tinker Hill Rd, Washington
$4,750,000
4 Beds ⋅ 6 Baths ⋅ 24193947 MLS
Ultra private hilltop estate with panoramic views overlooking Lake Waramaug with steps to private waterfrontage & floating dock. Chic 4 bedroom, 4 full and 2 half bathroom shingle-style house with infinity edge swimming pool & spa with magnificent views overlooking the lake. Formal entrance foyer leads to Great Room-style chefs eat-in Kitchen / Dining / Family room, with French doors to wrap around porch overlooking the lake. Library with fireplace. Up the beautiful double-height staircase is the luxe Primary Suite with fireplace, dressing room, and full bath with double-size steam shower, dual vanities & deep soaking tub in front of a wall of windows facing the lake. Three more bedrooms with lake views are on this level -- one en-suite and the other two share a Jack-and-Jill bath. The fully finished walk-out lower-level includes a media / game room with kitchenette, laundry & full bath with shower and leads to large stone patio and pool. 3-car detached garage with potential in-law / guest apartment. Fully fenced property. Outdoor fieldstone fireplace. Must see. Rare.

90 Tinker Hill Rd, Washington

26 Old Post Rd, North Branford
$4,750,000
4 Baths ⋅ 24194611 MLS
+/- 37,769 SF two-story building on a well-manicured 5.12-acre campus. The building is in superb condition. It is currently operated as a school. Its numerous features include classrooms and offices throughout, a 2,500-lb. capacity Otis passenger 2-stop elevator, gymnasium with full basketball court and stage area, heavy power, and sprinkler system. Exterior access to the ground level and sizable, finished lower level. Located in a quiet neighborhood near the intersection of Routes 22 and 17. The building is within easy walking distance to the center of Northford retail/business district. Only 5 miles to I-91 and Rt. 5 (Washington Avenue) in North Haven, and 6 miles to the Wilbur Cross Parkway. In addition to its use as an educational facility this property's potential purposes may include retail, office, church, and others.

26 Old Post Rd, North Branford

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