Vintage homes for sale & real estate in Connecticut, CT

Vintage Home for sale in Connecticut, CT:

Tucked away on a private, wooded two-acre lot in South Wilton, this 1890 antique farmhouse pairs quintessential New England character with expansive, light-filled proportions and a luxury pool complex completed in August 2025. The crowning jewel is the spectacular heated saltwater pool, seamlessly integrated into a sprawling custom stone paver deck sitting atop a majestic 10-foot natural boulder wall. Complete with a custom pool bar and a built-in automatic cover, this elevated terrace creates an unmatched private entertainer's paradise. Inside, the home has been freshly prepared for its next chapter with crisp white paint throughout and beautifully refinished original hardwood floors. Unli

Vintage Home for sale in Connecticut, CT:

Ideally situated in a highly walkable in-town location, this charming 1928 home offers a rare opportunity to create something truly special in the heart of Westport. Set on a lovely private lot, the property combines classic character with a wonderfully convenient setting close to shops, restaurants, schools, and all that downtown Westport has to offer. Owned and cherished by the same family for approximately 40 years, the home retains the warmth and architectural details that give an older house its distinctive appeal. Oak floors, gracious proportions, and timeless character provide a wonderful foundation for its next chapter. A first-floor in-law/ primary bedroom suite, thoughtfully added

Vintage Home for sale in Connecticut, CT:

Investor opportunity. Value add potential with this 1,787 sq ft Colonial featuring 3 bedrooms, 1 full bathroom, and 1 half bathroom with a good-sized fenced-in backyard. The home retains many of its original features throughout and boasts an open front porch which adds classic curb appeal and additional usable outdoor space. Recent neighborhood improvements include newly installed sidewalks, with the road reportedly set to be repaved. Its central location offers close proximity to retail stores, restaurants, businesses, and local amenities. The property is being sold strictly in as-is condition. This is a cash purchase, as it will not qualify for traditional financing. A great project for a

Vintage Home for sale in Connecticut, CT:

Quintessential New England Charm. Discover this classic Connecticut Fieldstone Country Retreat, an enchanting 1945 fieldstone home, beautifully situated on 2.24 picturesque acres along the New Fairfield/Sherman border. Rich in character, craftsmanship and timeless appeal, this distinctive country retreat offers over 2,830 square feet of living space, 4 bedrooms, 2 full baths and a setting that captures the very essence of Connecticut country living. From the magnificent stone exterior to the beautiful bluestone patios, walkways, steps and impressive stone walls, every corner of this property exudes charm. Inside, discover spacious, sun-filled rooms featuring hardwood floors, handsome wood t