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Cheshire Homes for Sale

Newest Pine Meadow, CT Homes For Sale

$424,900
2 Beds ⋅ 2 Baths ⋅ 24205765 MLS
Welcome to 133 Mountain Rd. If you've been looking for some land with a well kept home, this is your opportunity. This home sits on land that has been in this family for many generations!! The house has some special features as well and offers some unique items to it. The Kitchen is remodeled with new cabinets, Granite countertops, new flooring, the bathroom on first floor also remodeled with new flooring, and walk-in shower. There's a large living room with a beautiful gas fireplace and sliders that flow into a sunroom (which could be a dining room) and a huge bonus room completes this level (which could be 3rd bedroom). Up the stairs you'll find 2 large bedrooms, with a full bath. A special note about this home is every bedroom, has it's own covered balcony, including the bonus room, this home also offers some handicap features if needed, if not they are easy to remove. The Large walk out basement has been studded and ready to finish for extra space. Roof is newer, mechanicals in great shape, Large private backyard, 13.89 acres of woods for lots of fun, animals, whatever your needs are. Property backs up to a river. There a brand new klotter farms shed/small garage, a Quonset hut or 2. Don't wait to see this special property, I don't think you'll be disappointed.

133 Mountain Rd, Torrington
$749,900
3 Beds ⋅ 2 Baths ⋅ 24206406 MLS
Welcome to 180 Shore Dr - your own beautifully renovated waterfront retreat on highly desirable Lake! This exceptional year-round home offers the perfect combination of modern comfort, stunning water views, and the lake lifestyle you've been dreaming about. Featuring 3 bedrooms and 2 full bathrooms, the home has been extensively remodeled with quality finishes and thoughtful attention to detail throughout. Step inside to a bright, inviting interior filled with natural light from newer Andersen windows and doors. The beautifully renovated kitchen features modern appliances, sleek countertops, abundant cabinetry, and an open, welcoming feel that's perfect for entertaining after a day on the lake. Both full bathrooms have been tastefully remodeled, while LifeProof luxury plank flooring provides durability and easy maintenance. Enjoy year-round comfort with updated heating and central air conditioning. Outside is where this property truly shines! A newer deck and patio overlook Highland Lake, creating the perfect setting for morning coffee, summer dinners, sunsets, and unforgettable gatherings with family and friends. Step outside and enjoy direct access to one of Connecticut's most beautiful recreational lakes. Whether you're searching for a primary residence, weekend escape, or spectacular AirBnB, 180 Shore Dr delivers the lifestyle, location, and views that make waterfront ownership so special. Don't just buy a home - start living the Highland Lake lifestyle!

180 Shore Dr, Winchester
$359,900
6 Beds ⋅ 2 Baths ⋅ 24206509 MLS
Discover this versatile two-family residence offering a blend of modern updates and timeless charm. Each unit boasts three bedrooms and a full bath, providing ample space and comfort for tenants or multi-generational living. Both units have been beautifully renovated, featuring a brand-new kitchen with stylish finishes, updated bath, gleaming hardwood floors, and plush new carpet in the bedrooms. This level offers a fresh, move-in-ready appeal that renters or owners will love.

77 Hubbard St, Winchester
$132,900
1 Beds ⋅ 1 Baths ⋅ 24206272 MLS ⋅ Warrenton Mill BLDG.
Historic charm meets modern convenience in this unique condo located in a beautifully renovated mill! This move-in-ready home features dramatic two-story windows, exposed brick and warm wood accents that give the space incredible character. The fully applianced galley kitchen offers a breakfast bar overlooking the open dining and living area. The main level features a spacious primary bedroom with built-in storage and ample closet space, plus a full bath with tub and shower. Upstairs, the versatile loft provides additional living space overlooking the courtyard-perfect for a home office, guest space or den. A stackable washer and dryer are conveniently tucked into a loft closet. Enjoy secure building access, onsite management, ample parking and a convenient location near the elevator. Set along the river and close to shopping, dining, entertainment and transportation, this distinctive condo offers a combination of character and convenience that's hard to find!

839 Main St Unit 75, Torrington
$285,000
2 Beds ⋅ 2 Baths ⋅ 24206379 MLS
Charming and move-in ready, this 2-bedroom, 1.5-bath home offers comfortable living in one of Torrington's most desirable neighborhoods. While the home is fully livable from day one, a few spaces offer the perfect opportunity to add your own modern touches and personalize the home to your taste. The finished basement adds a spacious, versatile living area - perfect for a third bedroom, family room, home office, or entertainment space - extending your everyday living well beyond the main floor. Set on a generous 1/3-acre lot, the property is surrounded by lush, well-maintained grass and beautiful natural surroundings, creating a peaceful backdrop for outdoor relaxation, gardening, or play. Whether you're hosting a barbecue or simply enjoying quiet mornings on the lawn, this yard, patio, and deck deliver space and privacy that's hard to find. This home's mechanicals are well-maintained and feature a newer hot water heater and a brand new roof currently being installed. With its blend of functional living space, a coveted location, and a beautifully sized lot, 178 Concord Rd is a wonderful opportunity for buyers seeking comfort, flexibility, and room to make it their own.

178 Concord Rd, Torrington
$169,999
2 Beds ⋅ 2 Baths ⋅ 24206473 MLS ⋅ Homestead Condominiums BLDG.
Price to sell- Beautifully updated 2-bedroom, 1.5-bath condo featuring an open floor plan with a spacious living area and kitchen. Freshly painted throughout with numerous recent upgrades, including a new roof (June 2026), new kitchen cabinets, countertops, sink, flooring in the kitchen and living room, new carpet on stairs and in bedrooms, and a new storm door. Both bathrooms have been updated with new vanities and toilets, and new light fixtures have been installed throughout. The oversized covered garage provides ample parking and additional storage space. Conveniently located and move-in ready!

53 Harwinton Ave Unit 8, Torrington
$250,000
2 Beds ⋅ 2 Baths ⋅ 24206195 MLS ⋅ Black Rock Village BLDG.
Beautifully maintained 2-bedroom, 1.1-bath condo in the desirable Black Rock Village community. The open first floor offers a spacious kitchen, living room, and dining area, plus a half bath, storage closet, and attached 1-car garage. Upstairs are two generously sized bedrooms with ample closet space, a full bath with tub/shower, and a separate laundry room. A well-designed floor plan with plenty of storage and convenient features throughout.

203 Branch Rd Unit 1C, Thomaston
$1,295,000
4 Beds ⋅ 3 Baths ⋅ 24165953 MLS
This 1768 antique Cape Cod is a masterclass in historic preservation meeting modern luxury. Set on 15+ sprawling acres of rolling pastures, this estate offers the ultimate in privacy and sophistication, just moments from Sharon's town center and the Metro-North line.The ResidenceSteeped in character, the home features exquisite original wood moldings and gleaming hardwood floors throughout. The heart of the home is a true chef's kitchen, anchored by professional-grade Viking and Traulsen appliances, sleek Corian surfaces, and a dedicated pantry. Entertaining is effortless in the formal dining room or the expansive living room, which features a custom wet bar and one of three wood-burning fireplaces. The flexible main-floor layout includes a media room, laundry suite, and a serene guest wing.The SanctuaryThe second level serves as a private retreat, highlighted by a meticulously renovated primary bath serving three sun-drenched bedrooms. Outside, a grand screened-in porch offers panoramic views of the estate's picturesque grounds. Step out to a resort-style, in-ground pool and pool house, perfectly positioned for summer afternoons in the Litchfield Hills.The Grounds & AmenitiesBeyond the main residence, a substantial heated outbuilding/barn provides versatile space for a studio, gym, or collector's gallery, complete with a walk-in cedar closet. The property also features a heated two-car attached garage.

Sharon
$299,900
5 Beds ⋅ 2 Baths ⋅ 24206151 MLS
Well-maintained two-family home offering excellent owner-occupant or investment potential. First-floor unit features 3 bedrooms, kitchen, and living room and is currently rented. Second-floor unit is vacant and offers 2 bedrooms, living room, and kitchen. Separate utilities and laundry for each unit. Full basement provides additional storage. Entire home has undergone lead remediation. Great opportunity to live in one unit while generating rental income.

18 Pratt St, Winchester
$406,000
3 Beds ⋅ 1 Baths ⋅ 24204107 MLS
Welcome to this beautifully updated and thoughtfully designed 3-bedroom, 1-full-bath home, ideally situated on a quiet cul-de-sac in New Milford. This move-in-ready property has been fully updated and features handicap-accessible accommodations, offering both comfort and convenience. Enjoy beautiful views and a peaceful setting while still being conveniently located near downtown New Milford, major highways, schools, and everyday amenities. The flat front yard provides easy access, while the completely fenced-in backyard offers a private outdoor space for relaxing, entertaining, or enjoying time with pets. Additional highlights include a 1-car garage and a spacious basement with excellent potential for future expansion. The basement could be finished to create additional living, recreation, office, or storage space, and plumbing is already in place for the potential addition of a second bathroom. With its combination of updates, accessibility, location, outdoor space, and future potential, this home offers a great opportunity for a variety of buyers. Property is being sold as-is.

9 Hilltop View Ln, New Milford
$275,000
2 Beds ⋅ 2 Baths ⋅ 24205561 MLS ⋅ Lakeridge BLDG.
Welcome to resort-style living at Lakeridge! This spacious end-unit condominium offers 2 bedrooms, 2 full bathrooms, and a bonus room that provides the option for a home office, den, hobby room, or guest space. It's the perfect blend of comfort, options, and privacy. Inside, you'll find an inviting open living space featuring a beautiful brand-new gas fireplace, creating the perfect gathering spot year-round. The kitchen is equipped with stainless steel appliances. One of this home's most impressive features is the abundance of storage-far more than you'll typically find in a condominium. Step outside to your extended private deck, a sought-after feature that not all Lakeridge units offer, providing additional outdoor living space to relax, entertain, or enjoy the peaceful wooded surroundings. Located within the gated Lakeridge community, residents enjoy an exceptional lifestyle with amazing amenities including two pools, numerous sports courts, a pro tennis shop, a fitness center, two lodges, walking and hiking trails, skiing, kayaking, horseback riding, playgrounds, and year-round social activities. Enjoy maintenance-free living surrounded by the natural beauty of Northwest Connecticut, just minutes from shopping, restaurants, and everyday conveniences. Don't miss this rare opportunity to own an end-unit with exceptional storage, expanded outdoor space, and access to one of Torrington's most desirable communities.

337 Ledge Dr Unit 337, Torrington
$1,395,000
3 Beds ⋅ 3 Baths ⋅ 24205632 MLS
Step into a storybook setting with this meticulously renovated 1905 Nantucket shingle-style cottage. The grounds feature mature landscaping, historic stone walls and walkways, and a classic white picket fence. Offering a seamless blend of period craftsmanship and modern luxury, this pristine jewel box home is in mint, turnkey condition. Inside, the residence radiates light and warmth with hardwood floors, custom built-in cabinetry, wainscoting, exposed brick, shiplap details, and interior shutters throughout. The main level features a gracious living room with built-in shelving and a cozy library or study anchored by a wood-burning fireplace. A bright dining area with bay windows and French doors opens directly to a private cobblestone patio framed by hydrangeas, creating an ideal space for morning coffee or evening entertaining. The main floor is completed by a functional mudroom and a renovated half bath. Designed for maximum efficiency and culinary performance, the updated custom kitchen boasts honed marble countertops, classic brass hardware, and a high-end appliance package that includes a Bertazzoni gas range, True refrigeration, and a Fisher & Paykel double-drawer dishwasher. The second floor features a serene primary suite accented by vaulted shiplap ceilings and an ensuite full bath. Two additional bedrooms share a well-appointed second full bath featuring luxury Waterworks fixtures. The detached garage has been converted

135 Wykeham Rd, Washington
$225,000
2 Beds ⋅ 3 Baths ⋅ 24206198 MLS ⋅ East Farms Village BLDG.
Tucked away in the peaceful and sought-after East Farms Village on Torrington's east side, this bright, second-floor condo offers effortless living with an included chair lift for easy access if desired. The expansive main living area features soaring vaulted ceilings with an architectural accent beam, plush carpeting, and French doors leading out to a private balcony deck overlooking lush, mature greenery. A dedicated dining space flows seamlessly into the spacious eat-in kitchen, equipped with stainless steel appliances and ample cabinetry. Upstairs, you'll discover a beautiful, sun-drenched loft complete with its own bathroom and large skylights, creating the ideal setup for a third bedroom, private guest suite, or dedicated home office. Enjoy the peace and quiet of a tranquil neighborhood setting while being just minutes away from Route 202 conveniences, including Target, Walmart, and Starbucks.

508 Village Dr Unit 508, Torrington
$299,900
1 Beds ⋅ 1 Baths ⋅ 24203374 MLS ⋅ Willow Springs BLDG.
Welcome to this stylish townhouse-style contemporary condo! The main level features a spacious bedroom with a large walk-in closet, providing plenty of storage. The bright and inviting living room showcases beautiful hardwood floors, a charming electric corner fireplace, and sliders leading to a private balcony deck, creating an ideal space to relax or entertain. Enjoy the convenience of main-level laundry right in the unit. Upstairs, a large loft offers endless possibilities and can easily serve as a second bedroom, home office, or recreation area. Located in a well-maintained community in southern New Milford, this desirable complex is ideal for commuters with easy access to points south. Residents enjoy beautifully maintained grounds, an inviting clubhouse, and a refreshing inground pool for summer enjoyment. Whether you're looking for a full-time residence or a low-maintenance lifestyle, this condo is waiting for its new lucky owner! Provide your feedback on BizChat

178 Willow Springs, Unit 178, New Milford
$629,900
3 Beds ⋅ 2 Baths ⋅ 24205842 MLS
Welcome to 177 Lead Mine Brook Road, a private 5.55-acre retreat in desirable Harwinton. This well-maintained split-level home features 3 bedrooms, 2 full baths, a spacious layout, attached 2-car garage, and large rear deck. The property includes a beautiful barn with loft space, perfect for horses, hobbies, storage, or a workshop, plus a storage shed and ample parking for vehicles, trailers, and equipment. Ideal for homesteading, gardening, horseback riding, or simply enjoying peaceful country living, while remaining minutes from Route 202, shopping, dining, and local amenities. A rare opportunity in Litchfield County.

177 Lead Mine Brook Rd, Harwinton
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