54 houses for sale in East Canaan

Built in 1910, this charming Colonial is currently configured as a two-family home, featuring a 2-bedroom apartment on the first floor and a 1-bedroom apartment on the second floor. With its flexible layout, the property could easily be converted back into a spacious single-family residence. The first floor offers a large country-style eat-in kitchen with a fireplace and pantry, a generous living room, and two bedrooms. Upstairs, the second-floor apartment includes a kitchen, living room, bedroom, and full bath. Additional features include a screened porch, a nice backyard, and plenty of potential throughout. Priced to sell, this home is ready for someone with vision to restore it to its full charm and character. All room sizes are approximate

Blackberry River Oasis! With 1,100 feet of frontage on the Blackberry River and thousands of acres of protected state land as its backdrop, Stirling Farm offers a rare sense of privacy and tranquility. Cross a charming bridge with views of historic Beckley Furnace and its rushing spillway, then follow a private drive to a circa 1890 farmhouse nestled in a sunlit meadow. The home offers 3 bedrooms, 2 baths, and 1,500 square feet of living space. An updated kitchen with stainless steel appliances and a six-burner gas range complements original fir floors rich with patina, while a native stone fireplace anchors the spacious living room. Full of character and ready for its next chapter, the home presents an opportunity for thoughtful updates and personal touches to make it your own. The landscape is equally enchanting, with two magnificent mature Black Walnut trees, lovely apple trees, and a rare Rainier cherry tree offering its prized blush-colored fruit each June. Newly planted river bir

Historic Norfolk Village Home on 3.4 Acres Classic Litchfield County setting defines this 3.4-acre property at the edge of Norfolk village. Lovingly held within the same family for generations, this captivating 1907 antique home sits on flat, open land with a classic large country barn, hay fields, and a spring-fed seasonal brook. The charming five-bedroom, two-bath residence retains its finest period details: welcoming front and side porches, original wood trim, stained glass windows, and hardwood floors. The full two-story layout features 9.5-foot ceilings and generous room proportions on the first floor, various sized bedrooms on the second, a walk-up attic above, and a full basement below. Sun-filled and tranquil, this home awaits your vision - whether renovation or preservation, the bones are excellent. Nestled in a lovely neighborhood and only minutes away from Norfolk's coveted amenities, this offering is a rare opportunity

This very pretty village Victorian with lovely gardens was built in 1900 and has been well-cared for over the years. Many original features include cut glass and stained-glass windows, a full-width front porch with original fieldstone foundation, original fir and pine floors and 2 fireplaces

Tucked away on five private, professionally landscaped acres, this reimagined charcoal A-frame blends dramatic architectural style with refined modern living. Completely transformed from top to bottom, the residence features crisp new windows that flood the open interior with natural light, brand-new flooring throughout, and a brand-new kitchen designed for effortless comfort. The home's open layout flows seamlessly onto an expansive deck, perfect for outdoor dining or taking in the peaceful, scenic outdoors. Practical amenities abound with a spacious circle driveway for ample guest parking, plus a massive 1,200+ square foot detached 3-car garage with dedicated shop space-ideal for creators, hobbyists, or extra storage. Just two minutes from historic Falls Village-one of Connecticut's most charming small towns-offering cozy local eateries, immediate access to the Appalachian Trail, and the natural beauty of Great Falls. All the while, less than 30 minutes from Metro North train station

The Ultimate Entertainer's Estate! If your life centers around fine food, close friends, and effortless hosting, this custom country estate is your dream destination. The true heart of this expanded 3,933 sq. ft. home is a jaw-dropping chef's kitchen featuring double islands, premium stainless-steel appliances, a dry double-fridge bar, and a hidden walk-in pantry. This culinary masterpiece anchors a magnificent open floor plan. Guests can easily drift from the kitchen breakfast bar to the formal dining room fireplace, or gather beneath the soaring cathedral ceilings and raw timber beams of the giant great room. The interior's sweeping, open layout flows beautifully to the outdoors, creating an intimate indoor-outdoor entertaining haven. The expansive wood deck provides the ultimate platform for grilling, open-air dining, and relaxing, while the lightly wooded acreage perfectly frames the pristine, in-ground heated pool. The primary suite showcases vaulted timbered ceilings and a bespok

Exceptional Country Retreat in the Litchfield Hills! Set on more than seven acres in the desirable Music Mountain area of Falls Village, this gracious custom Colonial features rolling lawns, open meadows, a mature private apple orchard, sweeping westerly views, and spectacular sunsets. An expansive covered front porch welcomes you into a thoughtfully designed interior featuring a spacious kitchen, cozy fireside den, sunroom, formal dining room, and private library. The spectacular great room addition features soaring ceilings, a magnificent stone fireplace, walls of windows, and French doors framing the surrounding landscape - an impressive space for gathering and entertaining. The primary suite offers a wood-burning fireplace, while three additional bedrooms provide comfortable accommodations. An expanded upper level includes a versatile fifth bedroom with its own full bath. The two-car garage includes a tool workbench, while the expansive basement, with high ceilings, offers excellen

Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensui

Down a long private drive, this light-filled, artisan-built Cape blends over 5 acres of meadow and woods with Haystack Mountain views into a rare setting-complete privacy and close to town, summer music concerts, and the local swimming hole. Native cherry hardwood floors, solid wood doors, and wood trim run throughout. A central chimney anchors two fireplaces, while the main-floor primary suite allows for easy one-level living. Efficient mini-split heating and cooling provide year-round comfort, with a furnace for the coldest winter days. The upper level offers two bedrooms, a full bath, abundant storage, and an unfinished skylit room with potential for a studio, office, or additional living space. A mostly finished, dry walkout basement adds valuable living space with a recreation room, full bath, and French doors leading outdoors. Another room offers numerous possibilities. Featuring a 2021 roof and an oversized Western red cedar deck completed in 2024, this well-maintained home is m

Handsome 1935 Craftsman-style house on 2.79 acres surrounded by quiet, private land. There are 3,681 square feet of living area, a large living room with central fireplace, an equally large screened porch with stone pillars off the living room, a dining room/library room with secret office, a renovated kitchen, a main bedroom suite on the first floor and 3 additional bedrooms plus 2 additional full baths, The layout is gracious, and the rooms are spacious.The sunny stone terrace is gently surrounded by flower garden beds. Updates complement the style of the house. The house is offered furnished

This charming home sits on a 0.035-acre lot in the historic center of town. A 1900s colonial with 2 full baths, skylights, and refinished wood floors.Featuring an open layout with a spacious kitchen and dining room. All new energy-efficient appliances.New boiler with domestic hot water coil. A detached three-car garage. The property has a well-maintained lawn with fruit trees. Norfolk is home to the Yale School of Music, the Yale Music Shed, Infinity Music Hall, and Norfolk Curling Club. It also offers hiking trails and 2 state parks, plus golfing, pickleball, and tennis courts. The owner is a real estate agent

Located just minutes from the heart of Norfolk, this two-family home offers space, character and excellent income potential. The first-floor apartment features 2 bedrooms and 1 full bath, enhanced by a welcoming front porch-perfect for relaxing and enjoying the surroundings. The second-floor unit offers a generous layout with 4 bedrooms and 1 full bath, highlighted by a beautiful claw-foot tub and a large, bright living room providing both charm and comfort. Outside, the property sits on a large yard with ample parking on both sides of the home, allowing separate parking for each tenant. The property is in a desirable location close tot he center of town

Modern elegance meets turnkey peace of mind in this fully reimagined Sheffield retreat. Set on 2.3 level acres, this 3BR, 3.5BA sanctuary spans 2,748 square feet across three finished levels. The sun-drenched main floor features wide-plank white oak floors, a gas fireplace, a large half bath, a chef's kitchen with stainless appliances, white quartz counters, and seamless access to a wrap-around deck. Upstairs, a treehouse-like loft adds charm, while the primary suite delivers a spa-like experience. The three suites were designed for intimacy and privacy. The walk-out lower level houses a guest suite and fantastic game room. Renovated top-to-bottom with no expense spared, central A/C, and new mechanicals-just bring your suitcase. 15 mins to Guido's and 45 mins to the Wassaic NYC train

Known as The Bungalow, this spectacular Tudor-inspired estate set on 43.8 private acres is one of architect Alfredo S.G. Taylor's finest designs. Built in 1908 for a Remington Arms heiress, the home seamlessly blends Gilded Age grandeur with exceptional modern luxury. The dramatic great hall features soaring 40-foot timber ceilings, a monumental stone fireplace, and exquisite fieldstone and half-timber construction. Thoughtfully updated throughout, the home offers a stunning new eat-in chef's kitchen complete with a butler's pantry and premium appliances, including a True glass-door refrigerator, Miele dishwasher, Wolf warming drawers, Sub-Zero wine and beverage refrigerator, and an exceptional custom range with handcrafted hood. The luxurious marble-clad bathrooms have been beautifully renovated with Kohler fixtures, while custom cabinetry, updated electrical systems, and meticulous craftsmanship elevate every space. Spectacular balconies and a wraparound veranda extend from the main

Tower Hill House: 2002 Arts and Crafts inspired house on 7 acres with lovely gardens and lake views. 800 feet of frontage on the western shores of Doolittle Lake. A private oasis surrounded by the 2,000 acre Doolittle woods. 4,836 sf with 5 beds and 4.5 baths. Radiant heat. Detached two car garage. Designed by a local architect and built by local craftsmen

OFFERED FULLY FURNISHED AND TURNKEY. Built in 1964, this Berkshires compound comprised of three homes set on over fifty acres with panoramic southerly views. The main home, a modernist design collaboration between Bauhaus designer George Giusti and architect Crane De Camp, is a two-bedroom, three-and-a-half-bath masterpiece that features a gym, sauna, and gardens designed by a local landscape architect. For guests, they can choose between the three-bedroom, two-bath Cottage or the one-bedroom Cabin, both of which are intimate and offer plenty of privacy for family and friends. Whether it's poolside by day, trails in the afternoon, or hanging by the fire pit at night, there is something for everyone at this mid-century getaway set in the Berkshire hills and only minutes to Litchfield County

Charming rustic 3-bedroom, 1.5-bath home located on a picturesque country road in the Village of Southfield. Full of character and warmth, this inviting property offers a peaceful setting just minutes from the Southfield Store. With both residential and commercial zoning, it presents a unique opportunity for a primary residence, home-based business, or investment. Enjoy the charm of country living with the flexibility to suit a variety of needs in one of the area's most desirable village locations. There is also a huge garage on the property

Charming cottage-style home that offers far more space than meets the eye! The first floor features a spacious kitchen with abundant cabinet storage, pantry space, and a newer gas range, along with a cozy office nook, dining room, living room, full bath, two bedrooms, laundry room, and an inviting den. Upstairs offers three additional rooms, including two bedrooms, providing flexible space for guests, hobbies, or a home office. This home has seen many updates since 2019, including a new furnace, oil tank, front siding, and all new windows on the front of the house. Beautiful hardwood floors were added in the living room, dining room, and first-floor bedrooms, while the kitchen, laundry room, and den feature durable new laminate flooring. Additional highlights include a walk-out basement. With some updating, this home has tremendous charm and potential - a wonderful opportunity to create your dream space while enjoying the character and generous layout this property already offers. All

Situated on just over 1.6 acres in Southfield, this charming property offers access to a private tennis court, and pool through the homeowners' association. It has been meticulously updated and is ready for immediate occupancy. The beautiful screened porch and newly constructed terraced stonework establish the home as a genuine indoor/outdoor Berkshire retreat. Enjoy views of a striking gully and stream from your farmhouse sink and natural soapstone countertops, complemented by oak flooring throughout. During the cooler months, relax by the fireplace in the living room, which has been modernized to enhance the flow between the kitchen and porch, thereby maximizing the sense of space and expanding the home's footprint. This layout supports four bedrooms and three fully renovated bathrooms, all featuring contemporary tile work. Additionally, there is a full basement that includes separate storage and bonus room. Minutes from the CT state line and 20 minutes from Great Barrington, MA

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings

3 BR 2 Bath Home with tons of storage and lots of space. Great opportunity for a small homestead or someone looking for a home with shope space and outbuilding. BEING SOLD AS IS

Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensui

Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensui

Country living with space, privacy, and plenty of possibilities! This move-in ready 3-bedroom, 2-bath raised ranch sits on 1.75 acres, set back from a quiet country road with a level backyard, fruit trees, berry bushes, fire pit, deck, and hot tub. Inside, enjoy brand-new laminate flooring, new exterior doors, and a bright kitchen with new appliances, ample cabinetry, counter space, and breakfast bar. The spacious primary suite features his-and-her closets and a private bath with double sinks and garden tub. First-floor laundry adds convenience. A 22' x 24' garage with rear carport provides excellent space for vehicles, storage, or hobbies. The lower level offers great potential for additional living space, office, or recreation area. Land trust property behind the home adds to the peaceful and private setting. A great opportunity to enjoy country living with room to make it your own! Close to Butternut Ski Area. All room sizes are approximate

Country living with space, privacy, and plenty of possibilities! This move-in ready 3-bedroom, 2-bath raised ranch sits on 1.75 acres, set back from a quiet country road with a level backyard, fruit trees, berry bushes, fire pit, deck, and hot tub. Inside, enjoy brand-new laminate flooring, new exterior doors, and a bright kitchen with new appliances, ample cabinetry, counter space, and breakfast bar. The spacious primary suite features his-and-her closets and a private bath with double sinks and garden tub. First-floor laundry adds convenience. A 22' x 24' garage with rear carport provides excellent space for vehicles, storage, or hobbies. The lower level offers great potential for additional living space, office, or recreation area. Land trust property behind the home adds to the peaceful and private setting. A great opportunity to enjoy country living with room to make it your own! Close to Butternut Ski Area. All room sizes are approximate

Handsome 1935 Craftsman-style house on 2.79 acres surrounded by quiet, private land. There are 3,681 square feet of living area, a large living room with central fireplace, an equally large screened porch with stone pillars off the living room, a dining room/library room with secret office, a renovated kitchen, a main bedroom suite on the first floor and 3 additional bedrooms plus 2 additional full baths, The layout is gracious, and the rooms are spacious.The sunny stone terrace is gently surrounded by flower garden beds. Updates complement the style of the house. The house is offered furnished

Tower Hill House: 2002 Arts and Crafts inspired house on 7 acres with lovely gardens and lake views. 800 feet of frontage on the western shores of Doolittle Lake. A private oasis surrounded by the 2,000 acre Doolittle woods. 4,836 sf with 5 beds and 4.5 baths. Radiant heat. Detached two car garage. Designed by a local architect and built by local craftsmen

Located just minutes from the heart of Norfolk, this two-family home offers space, character and excellent income potential. The first-floor apartment features 2 bedrooms and 1 full bath, enhanced by a welcoming front porch-perfect for relaxing and enjoying the surroundings. The second-floor unit offers a generous layout with 4 bedrooms and 1 full bath, highlighted by a beautiful claw-foot tub and a large, bright living room providing both charm and comfort. Outside, the property sits on a large yard with ample parking on both sides of the home, allowing separate parking for each tenant. The property is in a desirable location close tot he center of town

Step into history at 1001 Canaan Southfield Rd, a rare 1797 Colonial estate set on over 23 breathtaking acres of mature, landscaped grounds. This extraordinary property features two serene ponds with fountains, over 300 feet of classic stone walls, and the scenic Umpachene River winding through the land. Extensive landscaping, stone patios, and picturesque outdoor spaces create a private retreat unlike any other. The home offers 4 bedrooms, including a spacious primary suite, blending timeless character with natural beauty. Included are three separate parcels, with an additional lot located across the street, offering endless possibilities for expansion, recreation, or investment. A truly one-of-a-kind Berkshire property rich in history, charm, and unmatched natural surroundings

Charming rustic 3-bedroom, 1.5-bath home located on a picturesque country road in the Village of Southfield. Full of character and warmth, this inviting property offers a peaceful setting just minutes from the Southfield Store. With both residential and commercial zoning, it presents a unique opportunity for a primary residence, home-based business, or investment. Enjoy the charm of country living with the flexibility to suit a variety of needs in one of the area's most desirable village locations. There is also a huge garage on the property