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$895,000
4 Beds 2 Baths ACTIVE Status 24172121 MLS
HOME-LAND -BARN. A TRUE NEW ENGLAND CLASSIC PROPERTY IN A POST CARD SETTING! For the Discerning Customer, whether You're an ANTIQUARIAN, HORSE & ANIMAL LOVER, or just seeking for a PEACEFUL & TRANQUIL LOCATION, this LITCHFIELD COUNTY HOME could possibly fit your Criteria. Stately 1789 , 11 Room 3,088 Sq. Ft. Colonial expresses Love, Warmth & Care. From the Solid Beams, Chestnut Wide-Board Floors, to the 12 over 12 Windows and Fireplaces, Displays the Charm & Character in this Residence! For a more Modern Twist, there is a Fully Remodeled Eat-in Kitchen with Quartz Counters, as well as Remodeled Bathrooms. 4 TO 5 Bedrooms, 3 Full Baths, Formal Dining Room & Comfortable Living Room. Spacious Sunken 20' x 21' Family Room with Cathedral Ceiling. Unique Loft offers a Birdseye View to the Family Room. Level 7 Acre Lot Enhanced by Stone Walls and Nice Plantings. Outbuildings include a 30' x 35' 4 Stall Horse Barn with Tack Room & Hayloft. 2 paddocks and a 25' X 30' Storage Building. Mechanicals include Oil Hot-Air Furnace, New propane heat in the sunken living room,200 AMP Electrical Service, Well Water & Septic System. A Quaint and Rural Atmosphere, but within Close Proximity to Major Shopping, access to State Parks, Lakes, Golf Courses, Ski Areas, and Local Arts and Cultural Venues. The Photo Library Partially tells the Story, but prospective Buyers need to Visit / Tour this Lovely Property in order to Appreciate its Attributes!!

469 Platt Hill Rd, Winchester

$725,000
2 Beds 3 Baths ACTIVE Status 24172055 MLS Indian Knolls BLDG.
Indian Knolls offers beautifully landscaped grounds and stylish home designs that create an elegant atmosphere in this 55+ community. Situated just a few miles from Litchfield center and a short distance from the chic Bantam hamlet, the location blends convenience with sophistication. Residents enjoy easy access to fine dining, as well as a variety of social, cultural, and recreational amenities, all of which are only minutes away. The community itself is a quiet village of 18 homes, thoughtfully built on sixteen acres bordered by conservation land and the Bantam River. This home features a single-level layout designed for comfort and ease. The living room boasts a cathedral ceiling and a gas fireplace, providing a warm and inviting space for relaxation. Entertaining is effortless in the formal dining room, while the eat-in kitchen offers a breakfast nook and doors leading out to a spacious deck, perfect for enjoying the outdoors. The primary bedroom impresses with abundant closet space and a large bath equipped with a separate shower and tub. An additional bedroom ensuite is finished with wall-to-wall carpet, creating a cozy retreat for guests or family. A full, partially finished basement includes an area set up as an exercise room and provides access to a small patio, ideal for additional outdoor enjoyment. Experience the vibrant lifestyle of Litchfield Hills, with its rich culture, diverse dining options, renowned wineries, libraries, gardens, local farms and craftsmen.

26 Seminole Cir, Litchfield

$725,000
2 Beds 3 Baths ACTIVE Status 24171689 MLS
Indian Knolls offers beautifully landscaped grounds and stylish home designs that create an elegant atmosphere in this 55+ community. Situated just a few miles from Litchfield center and a short distance from the chic Bantam hamlet, the location blends convenience with sophistication. Residents enjoy easy access to fine dining, as well as a variety of social, cultural, and recreational amenities, all of which are only minutes away. The community itself is a quiet village of 18 homes, thoughtfully built on sixteen acres bordered by conservation land and the Bantam River. This home features a single-level layout designed for comfort and ease. The living room boasts a cathedral ceiling and a gas fireplace, providing a warm and inviting space for relaxation. Entertaining is effortless in the formal dining room, while the eat-in kitchen offers a breakfast nook and doors leading out to a spacious deck, perfect for enjoying the outdoors. The primary bedroom impresses with abundant closet space and a large bath equipped with a separate shower and tub. An additional bedroom ensuite is finished with wall-to-wall carpet, creating a cozy retreat for guests or family. A full, partially finished basement includes an area set up as an exercise room and provides access to a small patio, ideal for additional outdoor enjoyment. Experience the vibrant lifestyle of Litchfield Hills, with its rich culture, diverse dining options, renowned wineries, libraries, gardens, local farms and craftsmen

26 Seminole Cir, Litchfield

$1,945,000
4 Beds 5 Baths ACTIVE Status 24161510 MLS
The Stonewall Estate at Dibble Hill: Set across three distinct parcels totaling 19 private acres, this property offers a rare combination of architectural character, natural beauty, and long-term flexibility bordering protected land held by the Cornwall Conservation Trust. At its center, a 4,800+ sq ft contemporary barn-style residence is perfectly sited on 5 acres overlooking a spring-fed pond, framed by classic New England stone walls and thoughtfully designed gardens that evolve with the seasons. A sun-drenched glass entry foyer creates a striking sense of arrival, leading into expansive living spaces designed for both relaxed country living and sophisticated entertaining. The French country kitchen is exceptionally appointed with dual Sub-Zero refrigeration, multiple freezer drawers, and a six-burner Wolf range. The great room is dramatic featuring soaring beam ceilings, a commanding fieldstone fireplace, and four sets of French doors opening to a raised bluestone terrace. A fully enclosed glass solarium offers year-round connection to the surrounding landscape. The home includes 4 bedrooms, 4.5 baths with Waterworks fixtures, Travertine and wide-plank hardwood flooring. Beyond the main residence, a 11.5-acre buildable parcel directly behind the home for privacy and a 1.6-acre parcel across the street; Detached four-car garage with an additional space below. A rare opportunity to create a weekend or full time legacy estate in the Litchfield Hills.

117-118 Dibble Hill Rd, Cornwall

$545,000
ACTIVE Status 24169493 MLS
The Ridge at Red Mountain: A Private 5.4 acre approved building parcel set along the foot of Red Mountain in Lakeville offering privacy, elevation, and long-range north and western views across the Litchfield Hills toward the Berkshires. The property features gently rolling topography and a serene setting surrounded by natural landscape and neighboring farmland. The owners are highly regarded architects and have designed a residence specifically for this parcel. Architectural plans are available and included in the land costs, offering an opportunity to streamline the design and building process. Buyers may choose to utilize these plans or pursue their own design, subject to local approvals. The listing agents have further details. This is not just land, but intentional architecture tied to the setting - a home site designed for the view. Abutting property to the north is in permanent conservation. Located minutes from the village centers of Lakeville and Salisbury, with access to local shops, dining, and outdoor recreation. Approximately 20 minutes to the Metro-North Railroad.

8 Red Mountain Rd, Salisbury

$1,499,000
4 Beds 4 Baths ACTIVE Status 24166479 MLS
Welcome to Fern House at 168 Fern Avenue-an extraordinary private country estate set on 3.71 picturesque acres in one of Litchfield's most coveted enclaves. Perfectly tucked behind mature landscaping and approached by a graceful circular drive, this quintessential New England retreat offers the rare combination of luxury living, equestrian amenities, and resort-style outdoor spaces just moments from the storybook charm of downtown Litchfield. Spanning more than 3,600 square feet, this expansive contemporary residence is filled with natural light, soaring ceilings, and oversized windows that frame lush views in every direction. A dramatic double-height foyer opens to an airy, open-concept main living area anchored by a stunning floor-to-ceiling fireplace-creating both warmth and architectural impact. Designed for elevated everyday living and effortless entertaining, the chef's kitchen is beautifully appointed with premium appliances including double KitchenAid wall ovens, a five-burner cooktop, dishwasher, pantry, and dedicated office nook, all flowing seamlessly into gracious gathering spaces and a formal dining room. The flexible and thoughtfully designed floor plan offers four bedrooms and three-and-a-half baths, including a desirable first-floor primary suite option.

168 Fern Ave, Litchfield

$740,000
2 Baths ACTIVE Status 24171303 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

$740,000
ACTIVE Status 24171301 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

$740,000
5 Beds 3 Baths ACTIVE Status 24171297 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

$740,000
3 Beds 2 Baths ACTIVE Status 24171289 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem

$2,000,000
ACTIVE Status 24170752 MLS
If You are looking for land with views to build your dream home, this is it. This is truly an "Estate Property". The 27 acres is cleared and open. There are several building sites at the top with 180 degree views. The land slopes gently down with a brook and 2 small ponds at the bottom. There is a fairly large barn and a smaller shop on the property in need of repairs. They are being sold AS IS! Bring your plans and build in a most beautiful part of the world in a sought after Connecticut town. Litchfield County is rural and beautiful. Enjoy farmers markets and country fairs. Visit any number of great restaurants in the area. There are many art shows, antique shops and boutiques to visit. As for outdoor activities, there are thousands of acres of land trust and hiking trails in Roxbury and surrounding towns. The Shepard River offers great fishing. There are ski areas close by as well as lakes for boating, fishing and swimming. Located under 2 hours from NYC! Taxes are based on 490 farming designation.

55 Ranney Hill Rd, Roxbury

$1,100,000
3 Beds 3 Baths ACTIVE Status 24170157 MLS
Set on 14+ private acres abutting Connecticut State land, this chic three-bedroom farmhouse offers the kind of quiet that's increasingly hard to find - and interiors that make you want to stay. The main floor is built around an open, light-filled plan that flows naturally from a chef's kitchen, featuring shaker-style cabinetry, butcher block counters, a farmhouse sink, and a professional range, through a generous dining area and into a living room anchored by a fieldstone fireplace. Step outside and relax or entertain on a back deck overlooking the lawn and surrounding forest. A powder room and laundry complete the level. Upstairs, a comfortable sitting area with a second fireplace connects two well-proportioned bedrooms sharing a full bath. The primary suite is a proper retreat: a handsome built-out office, a spa bath with soaking tub, and a walk-in closet done right. Outside, a classic red barn with metal roof adds character and utility. The Litchfield Hills at their best: two hours from Manhattan, with Kent's village life, Appalachian Trail, the Housatonic River, and Mohawk Ski Mountain all within easy reach.

9 Old Paddock Ln, Kent

$649,000
4 Beds 2 Baths ACTIVE Status 24169703 MLS
Historic 1762 Farmhouse - Rare Restoration Opportunity Bring your vision to life with this authentic 1762 New England farmhouse, rich in history and full of untapped potential. This 4-bedroom home offers a unique opportunity for restoration, blending original character with the chance to create something truly your own. Featuring classic colonial architecture, the home showcases solid structural integrity and striking original details that highlight its historic charm. While the property is ready for extensive updates, its strong bones and preserved features provide an exceptional foundation for a transformative renovation. Ideally situated in North Canaan, the property abuts a popular golf course, offering scenic surroundings and added appeal for future value. The peaceful setting provides both privacy and a connection to nature, making it an excellent candidate for a full-time residence, weekend retreat, or investment project. Whether you're an investor, renovator, or a lover of historic homes, this is a rare chance to restore and elevate a true piece of New England history.

76 S Canaan Rd, North Canaan

$250,000
ACTIVE Status 24170540 MLS
One-of-a-Kind Opportunity! Don't miss your chance to own this turnkey, award-winning restaurant in the heart of Litchfield County, perfectly situated in a high-traffic location.-Owner Financing Available! This well-established business offers 2,177 sq. ft. of warm, inviting atmosphere with 65 indoor seats and 35 outdoor seats-ideal for both casual dining and special occasions. Has a cafe license (liquor) but no bar. With a 10-year track record of success and a loyal customer base, this restaurant has earned recognition in top publications including the New York Times, Wall Street Journal, Hartford Courant, CT Magazine, and numerous local publications - Sale includes the business only (real estate excluded) and comes fully equipped with all infrastructure items. This is a rare opportunity to step into a thriving, reputable restaurant with an exceptional reputation-ready to operate from day one - Numerous infrastructure items are included in the sale totaling well over 100k (See list in attached docs)

436 Main St, Winchester

$1,300,000
ACTIVE Status 24170226 MLS
An exceptional offering awaits with this beautiful 61.54-acre parcel ideally positioned in a prime New Milford location, bordering the charming village of Washington Depot. This property is designated prime agricultural land, while also offering exceptional potential for a variety of future uses, including subdivision, a vineyard, equestrian estate, or private country retreat, solar farm. Featuring sweeping views with substantial level, usable land, the setting provides a beautiful and versatile landscape with endless possibilities. Originally subdivided in 1990 for 26 lots, any future subdivision would require new approvals, offering the opportunity to reimagine the property to today's standards. Enjoy the best of Litchfield County living with close proximity to downtown New Milford, as well as the scenic beauty of Lake Waramaug and surrounding towns. Maps and additional information available. A rare opportunity to bring your vision to life. Close to schools, shopping, dining, commuting with the ambience of New Milford and surrounding charming town of Washington Depot.

Chestnut Land Road, New Milford

$915,000
4 Beds 3 Baths ACTIVE Status 24160643 MLS
Beautifully renovated antique colonial on 4.5 private acres with a tumbling brook. Hardwood floors and original beams throughout, two wood- burning fireplaces, custom lighting, original wide-plank floors in some rooms, and a gorgeous, country kitchen with built-in appliances, including a warming drawer. The formal dining room anchors the heart of the home, with a small private study for multiple uses on one side, and a large living room on the other side. Every room shows loving attention to detail and comfort. Added onto throughout the years, the house flows comfortably. The original cottage, connected by a light-filled inner hallway with hardwood floors, offers a lovely family room or second living room, with a wood fireplace, a full bath that includes an imported English claw-foot soaking tub, and a cozy upstairs bedroom for guests. There are two large barns: one is a combination garage, tool shed, and wood shed. The other, built using the chestnut beams from the original barn on the property, is capacious, with a cement floor and truly endless possibilities. Gorgeous antique stone walls and perennial gardens abound, and the property is private and protected in the back by its natural landscape. Split air conditioning and a generator assist with comfort without sacrificing authenticity. Close to town and 20 minutes to the Ten Mile River Train Station. This home has been beautifully maintained, and will be standing long after any of our new houses are long gone. Turn Key!

221 Segar Mountain Rd, Kent

$1,595,000
4 Beds 4 Baths ACTIVE Status 24168858 MLS
Lovingly named "Nid D'Alcyon," French for Kingfisher Nest, by the current owner, this truly enchanting home is rich in history. This beautiful four-bedroom antique, dating to circa 1745, is set on one of Sharon's most scenic roads and tells a captivating story of life, travel, and love. Nestled within exquisite gardens and surrounded by a serene pond, mature trees, and perennial plantings, the setting is both peaceful and picturesque. The current owner has lovingly stewarded the property for 37 years, thoughtfully enhancing it while honoring its character. With great care, the home was renovated to maximize natural light-an exceptional quality for an antique-through raised ceilings where possible and thoughtfully designed additions that invite sunlight throughout the day. Improvements include central air conditioning, a full-house generator, and an expansion of the original petite footprint typical of antique homes. A first-floor primary suite with vaulted ceiling and en-suite bath featuring a custom fireplace was added, along with a mudroom, sunroom, and chef's eat-in kitchen. The formal living room offers another fireplace and beautifully crafted built-ins, creating a warm and inviting retreat. Every corner reflects exceptional care, seamlessly blending antique charm with modern comfort. This rare offering also includes a heated Gunite pool and barn, all set on five acres overlooking a dreamy pond.

130 Sharon Mountain Rd, Sharon

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