Refine Search
Map
Sort by
$275,000
ACTIVE Status ⋅ 24172891 MLS
Build your dream home at 17 Old Homestead Ln, South Kent in St. John's Peak. Set in the bucolic foothills of the Litchfield Hills, St Johns Peak is one of Connecticut's most bucolic enclaves. Enjoy unmatched tranquility and natural wonder on this sprawling and park-like 12+ acre property. Enjoy the beloved downtown of Kent to absorb the culture and natural beauty of Litchfield Hills and Berkshires. Only minutes from Lake Waramaug, Warren and New Preston. Adventure on one of the multiple nature preserves in St Johns peak including the one directly behind the property. Complete with old-age rock walls, this property is magical AND the bonus of 12+ acres to roam and build upon as your life grows and evolves. Wetlands/conservation at the back of the lot allowing for many options for home placement on the front of the lot.

17 Old Homestead Ln, Kent
$339,000
3 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24172528 MLS
Nestled on a level in-town lot, this classic Colonial offers timeless charm, solid construction, and endless potential. Featuring three bedrooms and beautiful hardwood flooring, the home provides a warm and inviting layout ready for your personal touch. The front porch is THE perfect seasonal place to unwind after a long day or start your day with coffee! The adorable galley kitchen with convenient main-level laundry adds to the home's functionality, while a detached two-car garage offers additional storage and versatility. While the property could benefit from some cosmetic updates, it has been well maintained and stands on a strong foundation-making it the perfect opportunity to build equity and create your dream home. Located in the heart of Canaan, you'll enjoy the best of small-town living with the convenience of being able to walk right into town. Known for its scenic beauty and rich history, this charming Litchfield Hills community is home to the stunning Great Falls and the unique New England Accordion Connection & Museum Company. Surrounded by nature, outdoor recreation, local dining, and a peaceful rural atmosphere, Canaan offers a lifestyle that's hard to leave once you experience it. Whether you're looking for your first home, a weekend retreat, or a place to put down roots, this property is a rare opportunity to become part of a truly special community.

287 W Main St, North Canaan
$299,999
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24172822 MLS
Welcome to this beautiful ranch style home in Oakville, offering a large open kitchen with granite countertops and an island, with plenty cabinet space and stainless steel appliance. Offering 3 comfortable bedrooms, living room with fireplace, detached 2 car garage with a loft area for office or playroom. A private yard surrounding the home perfect for outdoors activities and entertaining. Property has a shared driveway. Huge reduction on price, seller relocating.

251 Riverside St, Watertown
$314,999
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24172816 MLS
Freshly painted, lovingly cared for, move in ready level ranch with full capability for a home business or additional living space in a finished walk in /out basement! Zoned Local Business. Lower level was a beauty salon for years. Keep cool and help out on heating costs with a very efficient AC/Heat pump mini split system. This home has Real Hardwood floors, a bright and sunny kitchen with open feel and layout. Newer windows, Vinyl Siding for maintenance free living, and don't forget to walk out to your large and private Trex deck with views of light wooded land that is yours! This home is situated nicely on a lot with plenty of space with additional upper terraced part of land perfect for a home garden. Located in a quiet cul-de-sac. Newer roof with gutter guards and Sunbrella sunshade. Updated walk-in shower, and updated bath appointments in both full and half baths. First time being offered for sale since 1961!

86 Bird St, Torrington
$850,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24170495 MLS
Welcome to Owls Nest - a peaceful and private retreat tucked away on over 5 acres in the hills of Canaan in the foothills of the Berkshires. This beautifully maintained colonial offers 4 bedrooms, 3.5 bathrooms, and timeless charm throughout. Upstairs, all bedrooms feature hardwood floors, while the main level boasts 2 wood-burning fireplaces, a spacious living room, a formal dining room, and a cozy study with a stunning stone hearth. The kitchen includes an informal dining area and plenty of storage, making it perfect for both everyday meals and entertaining. It is a chef's delight. Dual ovens w air fryer, induction cook top, stainless hood and a natural live edge wood top. Step outside to enjoy your screened-in porch with ceiling fans, a large private deck w a hot tub, and a tranquil backyard surrounded by nature. The walkout lower level is finished with a full bath, an extra kitchen, and a bonus storage room ideal for a wine cellar. Additional features include a walk-up attic, central vacuum, ceiling fans, and garden spaces that attract gentle wildlife like deer, owls, and turkeys. Located on a quiet street and just minutes from skiing, golf, Lime Rock Park, fine dining, and cultural events, this home offers year-round enjoyment or a perfect weekend getaway. Lovingly cared for and thoughtfully updated by its current owners.Don't miss the chance to own one of Canaan's most serene and special properties. SqFt includes 1340 sqft in finished/heated lower level

11 College Hill Rd, North Canaan
$135,000
1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24171226 MLS ⋅ Bel Air BLDG.
Affordable one bedroom condo in Bel Air complex. Plenty of parking. Laundry on site. Pet friendly! Sold "as-is"

79 Belair Dr Unit 79, New Milford
$874,900
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24172449 MLS
Beautiful Colonial set on a private 3+ acre lot in sought-after Curtiss Meadows, ideally located on the southern end of Woodbury abutting the Southbury line. Set back from the cul-de-sac entryway, this well-cared-for home offers a wonderful blend of privacy, comfort, convenience, and thoughtful updates. The level, light-filled driveway provides easy access, while the peaceful setting creates a true sense of retreat just minutes from Woodbury and Southbury town centers, commuting routes, and everyday amenities. Offering 3,865 sq. ft. of finished living space on the main two levels, plus an additional 550 sq. ft. recreation room in the walkout lower level, this spacious home provides plenty of room to live, work, and entertain. The first floor features a gourmet kitchen with granite countertops and a large center island perfect for gathering, a spacious great room with cathedral ceiling, formal living and dining rooms, and a cozy den with fireplace. Upstairs, an open foyer/sitting area leads to a comfortable primary suite and three generously sized bedrooms. The exterior is beautifully maintained and includes a privacy fence, rear patio, and three-car garage. Recent improvements add even more value, including a new HVAC and central air conditioning system installed in March 2026, along with solar panels added by the owners to help curb rising energy costs. The two fireplaces give wonderful comfort and warmth.

8 Curtiss Mdws, Woodbury
$1,795,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24171982 MLS
Sprawling 4-bedroom colonial as part of a peaceful and private 17-acre estate in desirable Roxbury, CT. Sighted well on open rolling lawns with sweeping sunrise/sunset views, this property offers country living with exceptional versatility. The sun-filled eat-in kitchen features has sliders that open to a jumbo 58' deck with awning and open views. Generous main-level spaces include a dramatic family room with vaulted ceilings, wood-paneled dining room, living room with fireplace, large office/den/library, laundry room, and powder room. Upstairs are four bedrooms and two baths, including a spacious primary suite with walk-in closets and dressing area. The lower level has lots to offer with another half bath, gym/workout area, lots of storage and access to the 2-car garage. Outside, the spotlight is on the Pebbletec saltwater pool that is beautiful and low maintenance. The property has an abundance of open space and open sky in all directions. Multi-stall barn with hay loft and a 930 sq ft apartment, offering flexibility for equestrian pursuits, collector storage, creative studios, wellness uses, and income potential. Plus, detached 3-bay garage and a whole-property generator. Truly perfect for those seeking a country retreat or a gentleman's farm, and only 90 minutes from NYC - near Woodbury and part of the Washington-Roxbury corridor. Welcome home to Litchfield County!

25 Highmeadow Ln, Roxbury
$369,000
6 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24170813 MLS
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.

33 Terrace Vw, Norfolk
$435,000
4 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24172181 MLS
Timeless brick home offering classic charm and generous living space throughout. The spacious formal living room features a cozy fireplace and beautiful hardwood floors, creating a warm and inviting atmosphere. A second fireplace in the family room provides additional comfort and flexibility for everyday living and entertaining. The large formal kitchen is thoughtfully designed with stainless steel appliances, including a dishwasher, microwave, stove, and refrigerator, along with a center island perfect for meal prep and gathering. A tiled bath with a convenient washer and dryer adds everyday practicality. Enjoy sun-filled living with two bright bedrooms on the first floor, while the second level offers two expansive additional bedrooms. The lower level includes a versatile family/playroom with yet another fireplace, ideal for recreation or relaxation. Recent updates include new oil hot water heating, new hot water system, and a new oil tank for peace of mind. Additional highlights include a garage with door opener, a new driveway, and owned solar panels for energy efficiency. Step outside to your private backyard oasis featuring a swimming pool and a charming he/she shed-perfect for hobbies, storage, or a quiet retreat. A wonderful opportunity to own a well-maintained home with space, character, and modern updates. ALSO LOOK FOR THE WINE CELLAR added xtrea the solar panels are owned no monthly free free electric again said free electric

5 Sylvan Ave, Plymouth
$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
$779,000
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
$779,000
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
$795,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24171805 MLS
IDEAL NORFOLK RETREAT - Easy living is yours in this spacious, bright Contemporary with a 1st floor Primary Bedroom Suite. Tucked into one of the prettiest areas in Norfolk, close to Tobey Pond, Yale Summer Music, Infinity Theatre, and all of the outdoor recreation that the beautiful Litchfield Hills have to offer. Oak flooring, pocket doors, a dramatic vaulted ceiling and balcony, an updated Kitchen, a wonderful Porch and large Deck, two fireplaces, a new heating system, and so much more. Come see for yourself!

150 Sunset Ridge Rd, Norfolk
$200,000
ACTIVE Status ⋅ 24171867 MLS
Look no further for A Very Private location to build your Dream Home. A Wooded Hill top building site overlooking beautiful Winchester Center which can provide peace and solitude for your home or vacation retreat . Historical Winchester Center is deep with rich heritage and History of Winchester. Convenient access agreement to the Rear lot is though 151 Chapel Rd. property.

00 Chapel Rd, Winchester
$1,895,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24170163 MLS
Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

18 Ranney Hill Rd, Roxbury
$800,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24171546 MLS
Hidden Estate at High Street: A private Litchfield County retreat offering relaxed country living with exceptional versatility. This secluded country estate features fantastic outdoor spaces, 5 bedrooms, 6 baths, 12x24 salt water fountained pool, pool house and 2 studio apartments. Boasting 4,291 sq ft on 3.69 acres, this secluded oasis is the perfect hideaway to relax and refresh. The heart of the home is the oversized sunlit kitchen complete with granite breakfast bar, 6 burner stove, wall oven, dishwasher and double refrigerators. Kitchen is open to dining room and huge family room with sliders to pool area. There is also a formal living room w/granite fireplace. Upstairs consists of 4 bedrooms including a PBR suite with Juliet balcony and stairs down to the pool. The lower level features a walkout in-law suite with a living area, bedroom, kitchen and a full bath. A studio apartment features a kitchen, living room, bedroom and full bath. The pool area boasts a gorgeous fountain, hot tub, shower, lighting and a cabana with deck. The property is lined with apple, peach and pear trees. Minutes to town center, Route 8, Litchfield and Bantam Lake. Great multigenerational or rental opportunity.

341 High St Ext, Thomaston
$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
$1,000,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24157035 MLS
Discover modern serenity in this private contemporary retreat nestled on 3.44 private acres. The ascending driveway assures a sense of quiet and seclusion, leading you to a home bathed in natural light from a soaring two-story wall of south-facing windows, this home perfectly blends architectural drama with a peaceful woodland backdrop. The exterior features an expansive, brand new composite deck with its sleek cable railing system--perfect for al fresco dining or quiet mornings. Inside, the light filled, open-concept main level is anchored by 5 1/4" hardwood oak flooring and a dramatic granite gas burning fireplace. A full wall of custom built in's create style and ample storage. The kitchen is designed for functionality with its central island, quartz countertops and new Fulgar Milano induction range and a new LG refrigerator. Retreat to the main-level primary on-suite, which offers its own private deck access via French patio doors. Upstairs, a glass railed loft provides additional flexible space. The fully tiled walk out lower level includes a full bath offering excellent potential for an in law apartment, guest suite or private home office with a 2nd laundry hook up area in the garage. Meticulously maintained and newly painted throughout, this sanctuary is equipped with radiant heat, central air, a main level laundry and a newer water softening system.

28 Garnet Rd, Roxbury
$497,900
3 Baths ⋅ ACTIVE Status ⋅ 24171780 MLS
Think of the potential here ! Used as manufacturing for decades this three story property offers approx 6,243 sq feet of space plus an additional 3,513 sq ft in finished walkout basement totals to 9,756 sq foot of space. Plus there is a huge two story barn off the spacious parking lot that wraps around the building. The second floor has a stage built in from way back in the day, theres even a reception area with a built in ticket booth. behind that stage is a motorized freight elevator work space with mezzanine storage and stairs to first floor. the cap stone at front top of building says "1905"

707 Main St, Plymouth
$798,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24171521 MLS
A turnkey Litchfield County retreat just 90 min from NYC, offering historic character, designer finishes, and effortless weekend living moments from Washington, Litchfield, and Woodbury.Originally an 1800s caretaker's cottage, this beautifully renovated antique has been thoughtfully expanded & extensively updated between 2023 and 2026, blending timeless New England charm w/modern luxury. Set on 3.45 acres near the Washington town line, the property offers a move-in-ready escape in the heart of this bucolic county. The center of the home is a dramatic great room featuring an impressive fireplace, soaring two-story wall of windows & abundant natural light overlooking the surrounding landscape. A custom bar with built-in ice maker and beverage refrigeration makes entertaining effortless, while the skylit eat-in kitchen is appointed with handcrafted cabinetry and premium Sub-Zero, Wolf, and Miele appliances. 3 bedrooms, a primary on the main level with renovated en-suite bath, a second guest bedroom, and the 3rd is a dedicated space encompassing the entire 2nd floor; a private primary suite w/ separate office with views of the property. Central a/c for year-round comfort. Designed for both relaxation and entertaining, the outdoor spaces incl a spacious deck, fire pit area, mature stone walls, custom landscaping, and potential pool locations. 2-car garage. Mins to the Mayflower Inn this turnkey property offers the best of the area without the renovation project!

98 Carmel Hill Rd N, Bethlehem
$500,000
ACTIVE Status ⋅ 24171337 MLS
PROPERTY LOCATED VIA A LONG SHARED PRIVATE ROAD .9 MILE FROM STATE ROAD; Very remote and currently very private; Fabulous views to East and South; mountain stream flow along South boundary line; A Pond could be constructed. Subject to R.O.W. accessway, to other lots. Very special parcel for those seeking very quiet, removed-from 'active-traffic' activity. 4 miles to Salisbury; 14-20 miles to Great Barrington, MS, Catamount and Butternut Ski areas, and near other Berkshires attractions. 30-40 min to METRO NORTH RR. PICTURES NOTE: The Various pictures depict seasonal differences. Views subject to change from yearly growth of foliage.

Salisbury
$549,900
2 Baths ⋅ ACTIVE Status ⋅ 24171538 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
$2,500,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24168707 MLS
If you're seeking a private oasis with sweeping views, this exceptional property is the perfect retreat. Set on over 38 acres-28 of which are preserved-you'll enjoy lasting protection from future development and unparalleled tranquility. This expansive ranch-style home features a dozen rooms across two distinct wings, making it ideal for multi-generational living. Throughout the home, refinished oak floors add warmth and character. The library wing offers a stunning, oversized room with a wood-burning fireplace, complemented by two additional rooms and a full bath-perfect for a private suite, office, or guest quarters.

34 Black Snake Ln, Bridgewater
$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
$619,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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 ⋅ 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

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.