Vintage homes for sale & real estate in New Milford, CT

Vintage Home for sale in New Milford, CT:

Potential awaits at this stunning antique stone home. The property was formerly used as a bed & breakfast and a retirement home. Currently used as a boarding house. The original 1800's stone bldg has additions to form over 7500 sq feet of living space Three separate entrances with two staircases. The main section hosts 9 bedrooms with 6 full baths and 4 half baths which share a communal kitchen and dining room. There is an additional one bedroom apartment at the rear with a private entrance. See floor plans provided. Walk across the street to hike for miles in Steeprock's Macricostas Preserve. Walking distance to New Preston Village, the town beach at Lake Waramaug, and Averill Orchar

Vintage Home for sale in New Milford, NY:

228 Dog Tail Corners – Country Charm with Endless Potential. Welcome to this classic 1928 family home, brimming with country charm and timeless character. With hardwood floors, a welcoming living room, and a handy entryway mudroom, this home offers both comfort and functionality throughout. The kitchen is ready to be reimagined into your dream cooking and gathering space. The first-floor features two comfortable bedrooms and a full bath, while a full walk-up attic provides plenty of room for storage or future expansion. Recent updates include modernized windows for efficiency and a basement housing the oil tank and furnace, with Bilco doors offering easy access to the backyard. Outsid

Vintage Home for sale in New Milford, CT:

Escape the city and discover this wonderful estate, formerly Brinsmade Farm, in Sherman, Connecticut, offered for the first time in 60 years. Set on approximately 10 scenic acres in the heart of charming Sherman, this exceptional country home combines timeless New England charm with modern living. Originally a working dairy farm, the property was transformed in 1945 when the barn became a private residence. The estate includes three dwellings, perfect for extended family, guests, or multi-generational living-the Main House, Carriage House, and Pool House-offering approximately 5,200 sq ft with 6 bedrooms and 5 full baths. The Main House showcases cathedral ceilings, exposed beams, wide-plan

Vintage Home for sale in New Milford, NY:

Set among the rolling hills of Wingdale, New York, near the Sherman, Connecticut border, 1 Hoyt Road offers the quiet beauty of country living and the artistry of a thoughtfully built home. Morning light filters through tall windows, gliding across hardwood floors on the main level and the wide-plank flooring above. Each window frames views of trees and sky, blending the indoors with the surrounding landscape. The farmhouse combines timeless warmth with subtle sophistication. A brick entryway sets the tone for craftsmanship that continues throughout. The kitchen pairs rustic charm with everyday function, featuring exposed brick accents, built-in cabinetry, and a butcher block island that in

Vintage Home for sale in New Milford, CT:

Charming Cape in a Peaceful Brookfield Setting. This delightful 2-bedroom, 1.5-bath Cape blends classic character with thoughtful updates. The inviting living room features a wood-burning fireplace and gleaming hardwood floors, creating a warm and welcoming atmosphere. The kitchen is beautifully appointed with granite countertops and offers an easy flow to the light-filled sunroom - an ideal spot to unwind and enjoy the view of the gardens. The spacious primary bedroom includes a private half bath, while the second bedroom offers versatility for guests or a home office. Outdoor living is equally appealing with a patio area surrounded by mature perennials and a private backyard offering spac

Vintage Home for sale in New Milford, CT:

Once a beloved gathering place known as The Timber Trails Inn, this storied home now stands as a testament to time, craftsmanship, and quiet beauty. Set upon 1.4 private, level acres, it offers a sanctuary where history whispers through every beam and floorboard, and modern life unfolds in effortless harmony. All just 65 miles from NYC and lower Fairfield County destinations. Step inside, and you'll feel it immediately-the sense of grace that lingers in homes built with heart. Wide-board chestnut and white pine floors, dual staircases, and charming hidden nooks invite you to wander, to slow down, to imagine the lives that came before. The generous yet intimate flow of the main level makes i