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$1,499,000
4 Beds 4 Baths 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

$619,000
2 Beds 2 Baths 24171471 MLS
History unfolds at the original Lower Merryall schoolhouse. Reimagined and preserved as a unique home and infused with contemporary flair. The creative artisanal touches are evident throughout the home from beautiful finishes to the custom renovations. The first floor unfolds in an open layout, featuring dual sitting areas, a cozy fireplace, and a stunning kitchen complete with an island, concrete countertops, and a gas range. The contemporary color scheme against exudes a city vibe in the heart of the Litchfield Hills...just 2 hours from Manhattan. Wander outside to a spacious bluestone patio designed for entertaining, leading to a deck adorned with a pergola, chic black planter boxes, and an intimate gravel-based seating area. The yard boasts a striking creative studio, a charming greenhouse, raised garden beds, and a handy shed. The second level houses two cozy bedrooms with a shared bathroom, convenient washer and dryer, and a spacious loft area, perfect for relaxation or overflow for guests. This home is a rare find, a treasure for those who appreciate the allure of indoor/outdoor country living with a modern twist. Whether as a full-time residence or a part-time escape, this is a home that offers a unique and special lifestyle, ready to enchant its next stewards.

255 Aspetuck Ridge Rd, New Milford

$549,900
2 Baths 24171048 MLS
Exceptional redevelopment opportunity at 305 South Street in Plymouth, CT, directly across from beautiful Plymouth Lake. First time this property has been available since 1996. Currently operating as an upholstery shop, this versatile commercial property offers tremendous potential for investors, entrepreneurs, or owner occupants seeking a prime location with future upside. Plans were previously approved by the town to convert the upper level into residential living space while maintaining commercial use below, creating an exciting opportunity for possible single family, multifamily, or mixed use redevelopment. Buyers to perform their own due diligence regarding approvals, zoning, permits, intended future use, and potential benefits under Connecticut Public Act 25-164 encouraging adaptive reuse opportunities for qualifying properties. Property includes lake rights to Plymouth Lake, adding rare recreational appeal and increased desirability. Ideal for live/work space, income potential, retail, office, cafe, boutique shop, office conversion, and more. Rare opportunity in a highly visible and desirable location.

305 South St, Plymouth

$740,000
2 Baths 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
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 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 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

$269,900
4 Beds 2 Baths 24171141 MLS
Timeless character and thoughtful upgrades come together beautifully in this move-in ready bungalow. Bright and welcoming, the home is anchored by an impressive, fully renovated kitchen designed for both everyday living and entertaining. Custom cabinetry with pull-out shelving, a tile backsplash, warm wood countertops, and a farmhouse sink are paired with top-tier appliances, including a Sub-Zero refrigerator, Viking Professional gas range with 6 burners, pro hood with warming shelf, and an Advantium speed-cook oven. Hardwood floors run throughout, complemented by built-ins and updated baths that blend style and function. The living room offers a warm and inviting space with its distinctive Art Deco ceiling, gas fireplace, and French doors, flowing seamlessly into a generously sized dining room accented with classic wainscoting. With over 1,600 square feet of living space, this well-maintained home features four bedrooms. The main-level bath includes marble finishes, three closets, and a newer washer and dryer, providing both convenience and ample storage. Upstairs, all bedrooms have hardwood flooring beneath the carpets, and the primary bedroom enjoys direct access to a covered porch-perfect for quiet mornings or evening relaxation. Outside, the home continues to impress with a 12x14 pressure-treated deck topped with a pergola, ideal for entertaining. Conveniently located near schools, shopping, and major commuter routes.

84 Chestnut Ave, Torrington

$998,000
4 Beds 3 Baths 24169438 MLS
Beautiful 4 bedroom, 2.5-bath Colonial set on a picturesque, park-like property in desirable southern Roxbury. A dramatic two-story foyer welcomes you into a thoughtfully designed layout featuring a formal dining room, a spacious living room with custom built-in bookshelves, and an impressive family room highlighted by a floor-to-ceiling fireplace and custom built-ins. The kitchen is well-appointed with granite countertops, a center island, a Sub-Zero refrigerator and French doors that open seamlessly to an expansive deck and terrace-ideal for indoor-outdoor living and entertaining. Overlooking the beautifully landscaped grounds, the outdoor space features an in-ground pool, mature gardens, and lush plantings that create a private retreat-like setting. Additional highlights include ~300k in upgrades, beautiful hardwood floors throughout, a whole-house Generac generator, partially furnished with new furniture included, two-car garage underneath, an expanded driveway (30k), and a charming stone walkway that enhance the property's natural beauty. For those seeking a touch of homestead living, the property also features a professionally built chicken coop - perfect for raising chickens and enjoying fresh eggs at home. A rare opportunity to enjoy tranquility, space, and convenience, just 90 minutes from NYC.

336 South St, Roxbury

$100,000
24170518 MLS
Well-established package store located on a busy, high-traffic route in a residential town setting in Harwinton. 1,000 sq. ft. space with a clean, modern layout, updated flooring, lighting, and upgraded coolers. Strong product mix with a solid selection of wines, spirits, and bourbons. Located in a town with limited competition - only two package store permits, creating a stable and protected market environment. Positioned in a busy corridor with consistent traffic flow traveling to and from Burlington and surrounding areas in both directions. Additional foot traffic drivers include a nearby fairground that hosts seasonal events, bringing increased activity during peak times. Turnkey operation with additional revenue streams including lottery and cigarette sales. Strong upside potential through enhanced marketing, social media presence, extended hours, and improved signage on the main route. Financials and asking price will be disclosed to qualified buyers upon request. Inventory sold separately at cost.

Harwinton

$2,000,000
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

$1,200,000
3 Beds 3 Baths 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 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
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
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 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 and the ambience of New Milford and surrounding charming towns.

Chestnut Land Road, New Milford

$915,000
4 Beds 3 Baths 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

$1,700,000
4 Beds 4 Baths 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

$595,000
2 Beds 2 Baths 24169463 MLS
Experience riverside serenity in this masterfully updated country retreat overlooking the Shepaug River. Blending rustic soul with high-end modern comforts, this home offers a lifestyle defined by natural beauty and thoughtful design. The interior features a gourmet kitchen with a stunning live-edge bar, stone countertops, and a classic farmhouse sink positioned perfectly to overlook the water. A butler's pantry provides a secondary workspace, while a cozy wood-burning stove warms the main living area. Original hardwood floors flow through the inviting layout to the newly redone screened porch. Comfort is paramount with a dedicated mini-split AC system. The upper level features a primary with dual closets and a crisp full bath with classic white tile. The walk-out lower level is complete with laundry and updated mechanicals including a newer boiler and well tank. Outside, new stone steps lead to a spectacular stone bonfire patio. Whether you are hosting a summer cookout or stargazing by the fire, the sound of the river provides a constant, soulful soundtrack. Historically situated at what was once known as Woodville Corners, this property is located at the historic heart of the village, near the site of the original 19th-century general store and local post office. The property sits at the corner of Washington, Warren and Litchfield.

2 Valley Rd, Washington

$645,000
3 Beds 3 Baths 24170027 MLS
Thoughtfully renovated, this 1890 Victorian village gem is rich in architectural character. Beautifully crafted porches give the home its distinctive presence & serve as gracious extensions of living & dining spaces. Once the residence of Isabella Beecher Hooker & her husband, John Hooker, this home has a notable place in Connecticut history. Original details have been preserved & enhanced with substantial modern improvements, including a new kitchen and baths, a rebuilt front porch and roof, a new granite fireplace and brick chimney, a new propane warm-air heating system, central air, a new Viessmann water heater, and insulated attic and basement sills. The kitchen is well-appointed with a Bertazzoni six-burner gas range, Sub-Zero refrigerator, Bosch dishwasher, built-in cabinetry, center island, lit pantry & bar & convenient side entrance. A rear porch provides an ideal setting for grilling & entertaining. Stone walls & walkways are surrounded by established perennial gardens. Additional features include outdoor electrical access, walk-in ground-level basement, & two-bay garage with second-floor space offering potential for a studio, office, or other uses ("as-is"). Ideally situated within walking distance of cafes & the renowned Norfolk Library. Enjoy summer days at Tobey Pond, concerts on the village green, Yale chamber music, nearby hiking trails, and easy access to the Berkshires. A very special opportunity in one of Connecticut's peaceful & most treasured villages!

35 Maple Ave, Norfolk

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