Connecticut homes for sale starting at Fifty Thousand Dollars

$8,688,000 - New Canaan, CT

119 Proprietors Crossing New Canaan, CT - 119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function. A private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room offers a refined retreat, while the study, with a coffered ceiling and secret staircase, connects to the primary suite. The formal dining room glows under another Baccarat chandelier. Adjacent is the chef's kitchen, now complemented by the family kitchen in the Great Room featuring an enormous leathered quartz island. This room, with a 35.5-ft vaulted ceiling, boasts integrated high-end speakers as part of a whole-home audio system. The primary suite showcases a new 800 sq. ft. dressing room and a gorgeous two level bathroom with freestanding tub. The lower level of the home offers a media room, gym and wine grotto. The outdoor space includes a dining pavilion, outdoor kitchen, and a brand-new pool with spa. Built for luxury and efficiency, the home has commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones for your comfort. Additional features include a four car garage and an elevator accessing all levels of the home. This newly restored gem incorporates enhanced functionality for today's buyers, built to last for gener

$8,688,000 - New Canaan, CT

119 Proprietors Crossing New Canaan, CT - Welcome to 119 Proprietors Crossing, a dramatic estate by architect James E. Gearity. Set on four acres, this restored six-bedroom home blends elegance with modern function. A grand foyer with a sweeping staircase and Baccarat chandelier leads to refined living spaces, including the immaculate Blue Room, study with a secret staircase, and great room with 35+ ft vaulted ceilings and integrated speakers. The chef's kitchen is now complemented by the Great Room's family kitchen with a enormous quartz island. The primary suite boasts a new wetroom with a freestanding tub and an 800 sq. ft. dressing room. Outdoor spaces include a new pool/spa and a dining pavilion. Built for comfort, the home offers commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones

$8,688,000 - Call Listing Agent, CT

119 Proprietors Crossing Call Listing Agent, CT - 119 Proprietors Crossing is a breathtaking estate by architect James E. Gearity. Set on four acres, this fully restored six-bedroom home blends timeless elegance with modern function. A private drive and grand fountain lead you in to a soaring foyer with a sweeping staircase beneath a dramatic Baccarat chandelier. The parlor, with one of seven fireplaces, flows to a serene terrace. The Blue Room offers a refined retreat, while the study, with a coffered ceiling and secret staircase, connects to the primary suite. The formal dining room glows under another Baccarat chandelier. Adjacent is the chef’s kitchen, now complemented by the family kitchen in the Great Room featuring an enormous leathered quartz island. This room, with a 35.5-ft vaulted ceiling, boasts integrated high-end speakers as part of a whole-home audio system. The primary suite showcases a new 800 sq. ft. dressing room and a gorgeous two level bathroom with freestanding tub. The lower level of the home offers a media room, gym and wine grotto. The outdoor space includes a dining pavilion, outdoor kitchen, and a brand-new pool with spa. Built for luxury and efficiency, the home has commercial-grade systems, SIP walls, a Welsh slate roof, radiant heat, and 14 temperature zones for your comfort. Additional features include a four car garage and an elevator accessing all levels of the home. This newly restored gem incorporates enhanced functionality for today’s buyers, built to last for generations.

$8,000,000 - Kent, CT

23 Mauwee Brook Way Kent, CT - "The Falls." Prominent Modernist Architect, Charles Gwathmey of Guggenheim Museum renovation fame, designed this masterpiece in one of the most beautiful locations, offering dramatic views, cascading waterfall, nestled on 40+ acres of beautifully landscaped grounds with serene stream and extensive stonework. The property boasts a breathtaking western view of the Litchfield Hills. Just minutes to Kent Center with Swyft, Wilson's and great shopping, this exceptional offering provides tranquil escape while remaining close to vibrant shops and renowned award winning restaurants and just 90 minutes from NYC. Step inside and discover a light filled haven with soaring ceilings and curved walls and a stunning view of the waterfall from the Living room, which opens on to a picturesque stone terrace overlooking the babbling brook. A Michael Arad-designed addition of a full bedroom suite complete with office and captivating vistas. A tennis court, gorgeously designed pool and spa, acres of meadows and rolling landscape make this the perfect estate. A natural planted roof, and Deborah Nevins-designed park, gardens, perennial paths. The Stephen Sills designed interior spaces complement the curved walls, glass-covered corridor,

$8,000,000 - Kent, CT

33 Nodine Pasture Road Kent, CT - West Wind Hill, a bespoke country estate on 389 acres sits on the crest of a plateau overlooking panoramic protected views. Classic stone and shingle manor house with formal courtyard sited perfectly to experience spectacular sunsets and fairytale mists combined with the upmost in privacy. Access is via a private gated road that winds through trees, past old stone walls with glimpses of open meadow, and serene pond. Spacious rooms perfect for entertaining include a great room with a soaring peaked ceiling and a 20' stone fireplace, sun-filled formal dining room with three exposures, huge Chef's kitchen with a massive stone fireplace and adjoining catering kitchen. Beautiful reclaimed chestnut floors, exquisite detailing and banks of windows and French doors. The paneled library, office and primary bedroom suite are located on the first floor in a private wing of the house. Billiard room, complete with mini-kitchen, full bath and adjoining guest bedroom. Second-floor primary guest room with soaking tub and deck with views. Two bedroom suites with en-suite bathrooms, charming bedroom and an office complete this floor. Lower level with a media room, half-bath, wine tasting room and wine cellar with adjoining prep kitchen. Laundry room, craft room and gym. Beautiful stone steps lead to a stunning pool & pool house with full kitchen & tennis court. Two building maintenance court contains a pumping system for irrigating the lawns and gardens.

$7,750,000 - New Canaan, CT

68 Woods End Road New Canaan, CT - Tucked at the end of a long, sweeping driveway in one of New Canaan's most coveted enclaves, this stately residence is a masterclass in timeless design and exceptional craftsmanship. Created for both elevated entertaining and everyday comfort, the home unfolds with sophisticated ease-from the grand front entry to the beautifully curated interiors. Every space is thoughtfully scaled and exquisitely finished, with abundant natural light and views of the spectacular grounds from nearly every room. At its heart is a stunning, expansive chef's kitchen with a large center island, high-end appliances, and custom cabinetry that flows into the inviting family room-a perfect blend of elegance and ease. Formal rooms are gracious yet welcoming, offering effortless transitions to the outdoors. The rear grounds are extraordinary: manicured gardens, a pool surrounded by lush vines reminiscent of a Napa retreat, and a terrace spanning the length of the home-ideal for alfresco dining, entertaining, or quiet evenings under the stars. Upstairs, all bedrooms are ensuite, including a remarkable primary suite with spa bath and oversized walk-in closet. A guest wing offers its own skylit sitting room, while the finished lower level features a golf simulator, wine room, fitness room, elevator, and abundant storage. A full-service elevator connects the lower, main, and second levels of the home, offering ease and accessibility throughout. A rare opportunity to own an iconic home.

$7,695,000 - New Canaan, CT

1227 Ponus Ridge New Canaan, CT - Stylish, sophisticated and fun, this stunning 10,000 SF westside country estate borders two acres of land trust for total privacy, and is conveniently located close to town and schools. Extensive and impeccable renovations in 2023 with exquisite details and millwork, superior quality craftsmanship, luxurious amenities, smart home technology, designer light fixtures, new mechanicals, new cedar roof and a harmonious palette offers the perfect oasis for comfortable living, working and entertaining. Highlights include 10 ft. ceilings, 6 fireplaces, private study/office, 1st and 2nd floor family rooms, dramatic two story entry, and a new show-stopping Christopher Peacock custom kitchen and butler's pantry with furniture quality cabinetry, super sized island, major high end appliances and a sun-drenched dining area. All seven spacious ensuite bedrooms have gorgeous new bathrooms. The fabulous master suite with sitting area/fireplace has an amazing custom dressing room and extraordinary bath. Just completed lower level has a wine cellar, gym, media room, ensuite bedroom, cabana bath and is walk out to the pool area. The expansive bluestone terrace with fireplace abuts the glorious pool area with spa that is surrounded by lush landscaping and nature's beauty. This is a forever turnkey home ready to warmly welcome its new owners.

$7,500,000 - Washington, CT

65 Gunn Hill Road Washington, CT - Ultimate Views. Sprawling shingle-style estate with showstopping Great Room & unrivaled panoramic views overlooking Lake Waramaug and the surrounding hills. 22+/- acres with stone walls, blue stone terraces, long driveway & heated gunite swimming pool. 1st floor Primary Bedroom Suite with walk-in dressing closets, luxurious bathroom & private terrace. Cherry paneled Library with fireplace. Formal Dining Room. Butler's Pantry. Chef's Kitchen. Family Room. Guest bedrooms are all en suite. Mahogany deck. Fabulous outdoor fieldstone fireplace. A+ location. Must See!

$7,499,999 - Meriden, CT

515 Liberty Street Meriden, CT - A rare opportunity to acquire a well-maintained, fully updated private investment portfolio spanning 12 sought-after towns in Connecticut. This exclusive package includes 25 properties featuring a diverse mix of unit styles, ensuring broad tenant appeal and strong rental performance. Each property has been meticulously maintained and modernized, providing turnkey investment potential. This portfolio is being offered as a package only, presenting an ideal opportunity for investors seeking a high-performing, geographically diversified real estate portfolio with immediate income potential. Serious inquiries only.

$7,300,000 - Salisbury, CT

10 North Beaver Dam Road Salisbury, CT - Clarion Farm is an iconic French Country Estate & Horse Property in Salisbury, CT. It is a serenely private retreat with a 4-bedroom main house, a Studio on 16.25 acres, and a Horse Property on 30.72 acres for a total of 47 acres only a few minutes from the village of Salisbury and 15 minutes into Great Barrington. This exquisite property seamlessly blends tranquility with sophistication, creating an unparalleled living experience. Every aspect has been thoughtfully crafted to ensure maximum comfort and well-being, making it a true haven of peace and French Country Casual Luxury. All rooms are generously sized and flow beautifully into one another. The stunning private stone-walled pool courtyard is perfectly situated on the professionally landscaped property. Clarion Farm has a 12 Stall Horse Barn, a 6 Stall Barn, an Indoor 80 x180 Indoor Riding Ring, a 100 x 200 Outdoor Riding Ring, 6 Paddocks, and a 2 Bedroom Barn Apartment. Ideally situated near the many private & public schools, Catamount Ski Area and Aerial Park, and the villages of Salisbury, CT, Millerton, NY, Great Barrington, MA, and Wassaic Train Station. This listing includes two parcels: 10 N. Beaver Dam Road (Parcel ID: 2408134) and 471 Undermountain Road (Parcel ID: 2769378), with acreage and taxes reflective of both properties.

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