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14 Flanders Ln, Kent
$1,395,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24184750 MLS
First time ever on the market: this custom Contemporary abuts hundreds of acres of conserved land owned by the State of Connecticut, offering sweeping pastoral views and exceptional privacy less than five minutes from Kent Village Center. Inside the ~2,800 sq ft main house, an open floor plan blends with sophisticated country character. The main level kitchen is light-filled with breakfast bar seating, opening to a sitting area that flows into a sunroom and out to a bluestone patio framing the view. A formal dining room with vaulted ceiling opens to the living room, anchored by a fireplace. A main level bedroom with private bath completes this floor. Upstairs, the primary suite features a vaulted ceiling opening onto a sleeping porch, with a private bath of its own. Two more bedrooms share a full bath on this level. The home was also expanded to include an ~800 sq ft separate guest apartment, currently used as an expansive home office. This area would make a wonderful guest space, with the two existing offices easily converted into two additional bedrooms. The space already includes a living room, dining area, kitchenette, and full bath. The lower level of the main house has been finished to include a media room and laundry, and the original two-car garage is now finished storage space, easily converted back if needed. A rare find in a sought-after location, just two hours from NYC.

14 Flanders Ln, Kent

30 Hollow Rd, Woodbury
$1,395,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24168618 MLS
Step through the doors of history and into one of Connecticut's most treasured colonial residences. Built in 1760 and proudly listed on the National Register of Historic Places, the Jabez Bacon House is a rare masterpiece of 18th-century American architecture that has endured with remarkable grace for over 260 years. This distinguished home has also been recognized for its exceptional preservation and character, having been featured in Early American Life magazine and Historic Homes magazine-an honor that speaks to its authenticity and enduring appeal. This stately five bedroom home showcases original architectural details that collectors and history enthusiasts dream about. Seven fireplaces anchor the home's character across its generous 4,800+ square feet. Five beautifully paneled rooms reveal the craftsmanship of a bygone era, while antique wide-board flooring runs throughout, whispering stories of centuries past beneath every footstep.

30 Hollow Rd, Woodbury

Candlewood Mountain Road, New Milford
$1,390,000
ACTIVE Status ⋅ 24219308 MLS
Nestled in the serene landscape of New Milford, CT, past horse farms and fields, this special property on Mountain Drive presents a once-in-a-lifetime opportunity to own a piece of local history. Offered for the first time since its original ownership (back before the lake existed), this three plus-acre estate is a testament to refined countryside living. The level lot, adorned with a charming barn, invites you to design and build your dream home amidst nature's embrace. Complementing this vast expanse is a coveted 0.28-acre waterfront parcel that boasts a private beach, a personal dock, and breathtaking water views. There is a 3rd lot..... Imagine mornings spent basking in tranquil waters and evenings enjoying the sunlight glistening off the lake, right from your own backyard. This property, rich with history and potential, offers a unique canvas for crafting a bespoke lifestyle, combining elegance and comfort with unparalleled water access. Seize this opportunity to create a legacy estate, perfectly situated to enjoy both the peace of the countryside and the allure of lakeside living. Taxes on the barn are: $5,606.00 Taxes on the waterfront portion are: $3,179.00. Taxes on the 0.8 acres is..............

Candlewood Mountain Road, New Milford

11 Gaffney Rd, New Milford
$1,375,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24202206 MLS
This is a rare Litchfield County country property offering 8.32 private acres, Gunite pool, pond, meadow, oversized four-car garage, separate workshop and exceptional outdoor living-all surrounding a distinctive four-bedroom contemporary residence extensively improved by its current owners. Designed to connect with its beautiful setting, the light-filled home features a dramatic vaulted living room with floor-to-ceiling stone fireplace and direct access to the pool and outdoor spaces. The modern kitchen opens to a pergola-covered dining patio, while west-facing decks on multiple levels overlook the surrounding grounds. A light-filled first-floor primary-suite addition creates a private retreat with skylights, a wall of windows, vaulted ceiling, walk-in closet, luxurious bath and private deck overlooking your private meadow. Upper levels provide additional bedrooms, baths, another fireplace and private west-facing decks. Outside is where 11 Gaffney becomes truly distinctive. The 8+ acre property combines a Gunite pool, pond, meadow, mature landscaping, extensive patios and decks, oversized four-car detached garage, separate 15'x9' workshop building, 8x4' attached garden shed and additional storage, one car garage and mechanical room below the primary suite.

11 Gaffney Rd, New Milford

Chestnut Land Road, New Milford
$1,300,000
ACTIVE Status ⋅ 24170226 MLS
An exceptional offering awaits with this one of a kind 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

11 Evergreen Dr, Roxbury
$1,297,500
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24154135 MLS
This is 'the best deal in Roxbury"! New construction on 3.39 acre lot. The style is a classic farmhouse design Cape with a covered front porch with metal roof. The ceiling height on the main level 9'and 8' on the upper level. Both levels have wood floors. The primary suite is on the main level with a large bath including a shower a free standing tub and a walk in closet. The kitchen is open to the family room which has a bank of 3 sets of sliders to the back deck area and a fireplace on the end wall. The main level includes a formal dining room, formal living room and a main level laundry/mud room. The upper level includes 3 additional bedrooms and 2 full baths. There is a study area as well as a rec room over the garage. The large 2 car garage will have an electric car charger. Roxbury is a lovely small town with bucolic farms and farmers markets. It is very sought after for weekend and summer homes. There are many land trust areas for hiking and exploring. The Shepard river is great for fishing and tubing. Litchfield County has many lakes for out door recreation. There are ski areas close by and lots of summer fairs. The area is known for art galleries, antique shops and great restaurants. Taxes TBD

11 Evergreen Dr, Roxbury

73 Dublin Rd, Canaan
$1,295,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24203845 MLS
Tucked away on five private, professionally landscaped acres, this reimagined charcoal A-frame blends dramatic architectural style with refined modern living. Completely transformed from top to bottom, the residence features crisp new windows that flood the open interior with natural light, brand-new flooring throughout, and a brand-new kitchen designed for effortless comfort. The home's open layout flows seamlessly onto an expansive deck, perfect for outdoor dining or taking in the peaceful, scenic outdoors. Practical amenities abound with a spacious circle driveway for ample guest parking, plus a massive 1,200+ square foot detached 3-car garage with dedicated shop space-ideal for creators, hobbyists, or extra storage. Just two minutes from historic Falls Village-one of Connecticut's most charming small towns-offering cozy local eateries, immediate access to the Appalachian Trail, and the natural beauty of Great Falls. All the while, less than 30 minutes from Metro North train station!

73 Dublin Rd, Canaan

77 Judds Bridge Rd, Roxbury
$1,295,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24193455 MLS
A custom-designed Judds Bridge Colonial in a coveted location, privately set amid mature trees and established plantings. A dramatic double-height marble foyer introduces the home's beautiful architectural millwork and rich cherry floors on the main level. The well-proportioned interiors include formal living and dining rooms, office or bonus room, an open and eat-in kitchen with solid cherry cabinetry, double oven, cook top, peninsula with seating, pantry, powder and laundry room, and a spacious den with vaulted ceilings, antique beams and centered around a soaring Rumford fireplace. The primary suite features a tray ceiling, en-suite bath with double sink, generous walk-in closet, while three additional bedrooms share a full bath. Out the French doors onto Ipe deck provides a refined setting for outdoor living and your private back yard. Additional highlights include a three-car garage, an unfinished bonus room over the garage that offers excellent expansion potential, new UV paned deck doors, updated mechanicals, architectural roof shingles, and a portable generator. Quintessential New England living at it's best!

77 Judds Bridge Rd, Roxbury

27 Morey Rd, Sharon
$1,295,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24186400 MLS
Set along a quiet, dead-end road in the Ellsworth section of Sharon, this newly constructed shed-roof home was designed for simple, efficient living with a strong connection to the Earth. Solar panels and a heat pump system keep utility costs remarkably low, while expansive windows capture natural light and western sunset views. Thoughtful details include Bosch appliances, copper light fixtures, and a refined material palette that balances warmth with modern simplicity. The generous primary bedroom wing features a sauna, two separate dressing areas, and a bathroom finished with terrazzo tile. Two additional bedrooms occupy the opposite side of the home, creating a practical separation of spaces for family and guests. The exterior is clad in durable Hardie board siding, designed to age gracefully and require minimal maintenance. The landscape has been carefully planned and will continue to evolve with native wildflower meadow, apple trees, and maple, creating an ever-changing backdrop through the seasons. A detached two-car garage completes this understated and highly efficient modern home, offering a rare combination of Scandinavian design, low-maintenance living, and a peaceful country setting in one of Sharon's most desirable locations.

27 Morey Rd, Sharon

105 & 109 Us-7, Salisbury
$1,295,000
1 Baths ⋅ ACTIVE Status ⋅ 24133160 MLS
Discover a rare opportunity in the heart of Salisbury with this exceptional mixed-use property at 105 & 109 Route 7, offering a perfect blend of commercial versatility and residential comfort. Set on a level one-acre lot, the property features a 2,583 square-foot five-bay automotive garage currently operating as a licensed car dealership and auto repair facility, along with a charming 1,270 square-foot three-bedroom home. Once a full-service gas station in the 1950s, the site remains approved and zoned for fuel service and also allows for restaurant, drive-thru coffee, and various other commercial or mixed-use opportunities. Engineering and architectural plans for proposed future uses are available upon request, making it even easier to bring your vision to life. With excellent visibility along Route 7, low annual taxes, and clean 2019 DEEP environmental testing, this property offers both peace of mind and incredible potential. Located just one mile from Lime Rock Park and two blocks from the regional high school, it benefits from steady local and seasonal traffic alike. Whether you envision expanding the existing business, reintroducing a gas station or cafe, or creating a new destination entirely, 105 & 109 Route 7 presents a unique chance to invest, create, and thrive in one of Litchfield County's most scenic corridors.

105 & 109 Us-7, Salisbury

509 Weekeepeemee Rd, Woodbury
$1,278,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192284 MLS
Steeped in 18th-century charm, this rare 1747 Saltbox estate seamlessly marries historic integrity with modern luxury. Tucked away on a peaceful country lane, the main home boasts original wide-plank wood floors, dual fireplaces, twin staircases, authentic built-ins, and freshly renovated baths. At its heart is the kitchen featuring Viking appliances and granite counters that open to garden views. Step through the screened stone-and-timber breezeway to a newly expanded patio and custom firepit crafted directly from native fieldstone, all beneath a classic wood-shingle and copper roof. The surrounding grounds function as a true New England compound. A separate two-bedroom carriage house offers built-in guest quarters with a covered porch and an oversized 2.5-car garage. Nearby, a newer two-story 40'x28' barn provides flexible space for a creative studio, vehicle storage, or livestock, complemented by two additional storage sheds. Recent improvements include, but are not limited to, a new cedar-shingle roof with copper downspouts (2025), new A/C, fresh interior paint throughout (2026), and refinished flooring. It is an unmistakable rural sanctuary with abundant room for hosting friends and extended family.

509 Weekeepeemee Rd, Woodbury

2540 Norfolk Rd, Torrington
$1,278,000
1 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24175012 MLS
This one-of-a-kind custom designed home is a peaceful sanctuary, situated on top of a hill on 18 secluded acres (that is subdividable) and bordered by conservation land. To access the home, you drive over a bridge and up a paved and gravel driveway. The home is fine for entertaining, featuring a cook's kitchen with stainless steel appliances, a breakfast bar and granite leather suede countertops. The expansive dining area includes a gas fireplace, and the living room boasts a soaring ceiling and a wood burning fireplace. A large deck provides amazing views, and you can enjoy swimming all year round with the indoor 18x36 inground saltwater pool, complete with a dehumidifying system and alarm. The main level is completed by a laundry room, mud room and attached two-car garage. For a retreat, the primary bedroom suite offers a sitting room with custom crafted Mahogany doors and ceiling fan, with a luxurious primary bath featuring a soaking tub, tile shower and dual sinks. The lower level includes a possible in-law, wine cellar, a full bath, a tandem 2-car garage and a patio. An elevator which serves all 3 levels of the home. Mechanical features of the property include energy efficient geothermal heat and air conditioning, a generator and underground utilities. The grounds are thoughtfully cultivated featuring fruit trees, blueberry and raspberry bushes, fenced in gardens, a stone walkway and the paved driveway. A beautiful place to reside in the Litchfield Hills

2540 Norfolk Rd, Torrington

44 Keeler Rd, Sharon
$1,250,000
ACTIVE Status ⋅ 24089909 MLS
NO NEED TO WAIT FOR TOWN APPROVALS! Design development plans with project entitlements in place for a spectacular, modern, 5-bedroom, 5,400 sq. ft. two-level home-featuring an indoor pool, sauna, multiple attic areas and attached garage are paired with this expansive 33.73-acre parcel in Sharon's desirable West Woods section. Nestled amidst tranquil nature, this remarkable property offers an unmatched blend of privacy and accessibility, ideal for a serene retreat, equestrian estate, or exceptional investment. Boasting 443 feet of frontage on a bucolic country road, the building site is set back along the road. Behind the building site, an old wood road crosses a private pond, leading to your own hiking trail along the babbling Macedonia Brook to a higher open area which includes a proposed 4.52 acres of open meadow on the higher side of Macedonia Brook. I The property is bordered by protected land trust, ensuring a forever-preserved natural backdrop. Enjoy easy access to local amenities, located just 7 miles from Kent's vibrant town center, shops, and restaurants, and minutes from The Kent School, Macedonia State Park, Skiff Wildlife Preserve and the Appalachian Trail. Buyers may choose to streamline their build with the included, fully approved designs and entitlements or pursue their own custom vision subject to local approval.

44 Keeler Rd, Sharon

94 Washinee Heights Rd, Salisbury
$1,250,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172243 MLS
This 70s Modern home has been revamped to a 21st century Contemporary. Perfectly situated between the spectacular east and west lakes in the Twin Lakes region of Salisbury, it's an easy walk to the lake to enjoy part ownership of the beach/lake access point, or relax in the back yard by the pool, relishing in the privacy and beauty of your surroundings. The upper level features an open floor plan with vaulted ceilings, lots of light, and wood beams. Walk out right onto the expansive deck, or enjoy the private balcony off the Master bedroom suite. The lower level has two additional bedrooms, an office, a full bath, a laundry area, and a central family room. Other features include a whole house generator, an owned solar electric system, mini-splits for climate control (heat & AC), and professionally maintained grounds. This is a clean, well kept home and property in the middle of a lake community in one of the most desirable areas in the Berkshires. Close to Salisbury, Hotchkiss, Berkshire, and Indian Mountain schools, and less than 30 minutes to the Wassaic train station.

94 Washinee Heights Rd, Salisbury

212 Looking Glass Hill Rd, Litchfield
$1,200,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24208526 MLS
Situated on 10.94 private acres across Litchfield and Morris, this updated and charming Cape Cod home offers a perfect blend of comfort and scenic tranquility. The main level features a remodeled kitchen complete with quartz and soapstone countertops and a pantry with a dedicated coffee bar. The cozy living room highlights a wood-burning fireplace, flowing seamlessly into a sunroom overlooking the serene pond and professionally landscaped backyard. The main-floor primary suite boasts an updated bathroom, walk-in closet and a slider leading directly to the back deck. Convenience is the key with a main-floor laundry area, mudroom and half bath leading to the attached three-car garage, plus a versatile office/gym with a separate entrance. Hardwood flooring runs throughout both the main and upper levels. Upstairs you will find two comfortable guest bedrooms-one with a walk-in closet and a full bath. The finished lower level provides additional living space with a large family room and full bath, offering easy access to the patio and in-ground Gunite pool. An additional one-car under-house garage space provides ample storage for equipment or hobbies. Outside, enjoy the ultimate privacy featuring classic stonewalls and a dedicated garden area. Conveniently located just minutes from fine dining, shopping, golf courses, private schools and all the charm of the Litchfield area.

212 Looking Glass Hill Rd, Litchfield

57 Lily Pond Rd, Harwinton
$1,200,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24209761 MLS
Welcome to 57 Lily Pond Road - a rare Harwinton estate offering over 5671 sq ft of finished living space, 4 bedrooms, 5 baths, and a beautifully designed in law/au pair apartment. Set on a private cul-de-sac, this custom home blends modern comfort with multi generational flexibility and resort style amenities. A dramatic two story family room with skylights anchors the main level, opening to a spacious kitchen, formal dining and living room, and expansive deck overlooking the grounds. The first floor bedroom provides ideal guest or office space with its own bathroom. Upstairs, the primary suite features a walk in closet and spa inspired bath, accompanied by generously sized bedrooms and additional full baths. The lower level has an in law/au pair apartment which offers its own private living area, bedroom, bath, kitchen and separate entrance - perfect for extended family, live in support, or long term guests. Can also be used for recreation, fitness, or home office needs, with walk out access to the yard. The beautiful yard consist of 2.85 acres with a fenced inground pool for summer enjoyment and a 3 car garage. A rare combination of size, privacy, and flexible living - this is one of Harwinton's most versatile homes.

57 Lily Pond Rd, Harwinton

391 Kent Cornwall Rd, Kent
$1,200,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24207531 MLS
A Kent Landmark, Reimagined - This historic converted dairy barn offers 3,600 sq ft of flexible living space on over 14 private acres, with direct Housatonic River frontage and protected land trust borders. Hand-hewn beams, cathedral ceilings, and skylights carry the property's history throughout; while a converted silo houses a home office, art studio and gym. The sunny modern kitchen, renovated for large gatherings and generous entertaining, features an oversized island with seating, a commercial range, premium appliances, double sinks and dishwashers, and a wine cellar. The spacious dining area and lounge open to a landscaped patio overlooking a heated in-ground pool and cabana. Grounds include perennial gardens, several outdoor seating areas, and private manicured trails leading to a stream with waterfalls and the river frontage. The home includes private guest quarters and a primary suite with an elegant en suite bath featuring a radiant heated floor, sitting room, office and two walk-in closets. It features 3 additional updated bathrooms, a formal living room, pellet stoves, generous parking and EV charging. In-home garage with a workbench and space for a games table, plus old-style out-buildings complete the property.

391 Kent Cornwall Rd, Kent

00 Litchfield Rd, Watertown
$1,200,000
ACTIVE Status ⋅ 24155266 MLS
An exceptional opportunity to acquire / develop 84.01 of land on Litchfield Road in Watertown, Connecticut. The portion with frontage is zoned R-30 consists of 27.38 acres. The other portion consisting of 56.63 Acres is situated in the R-70 Zone Residential land with frontage on Butternut Lane. [BUTTERNUT ROAD IS SUBSTANDARD & PAPER IN PART] This expansive parcel offers outstanding potential for a 1 or more private estate or a thoughtfully designed residential subdivision (subject to town approvals). Located along one of Watertown's scenic corridors, the property provides a blend of natural beauty and development flexibility. With generous acreage and R30 zoning (minimum 30,000 sq ft lot size), this site is well-positioned for multiple building lots or a secluded single-family compound surrounded by tranquil New England landscape.

00 Litchfield Rd, Watertown

385 Second Hill Falls Ln, Bridgewater
$1,199,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191859 MLS
Spectacular Estate home in a coveted Bridgewater neighborhood, privately set on 8+ acres of manicured grounds with towering pines, specimen trees & beautiful plantings. A long, elegant approach leads you to this award-winning, custom-built residence, where exceptional craftsmanship is evident throughout. The airy two-story foyer opens to gleaming hardwood floors, exquisite millwork and oversized windows that flood the home with natural light. The main level features a great room with soaring ceilings, fieldstone fireplace & access to the expansive deck. The chef's kitchen offers granite countertops, a large eat-in area and sliders to a delightful screened mahogany porch that is perfectly nestled amid the property's stunning landscaping. A formal dining room and cozy study both overlook the sweeping lawns and provide add'l spaces for entertaining & relaxation. The first floor primary bedroom suite is a retreat in itself with two large walk-in closets & a spa-like bathroom. There is also a powder room, add'l full bathroom, laundry room, and access to the heated three car garage to complete the main level. Upstairs are two generously sized bedrooms, a full bath, cedar closet with abundant attic storage and a spacious bonus room or 4th bedroom with private access from the garage. The unfinished lower level offers an additional (sq.ft?) of potential living space, plus access to a separate one bay garage and workshop with its own driveway, ideal for the car enthusiast or tinkerer.

385 Second Hill Falls Ln, Bridgewater

32 Red Bird Ln, Salisbury
$1,195,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24215736 MLS
This expansive ranch-style home is situated on a quiet cul-de-sac in Lakeville, CT, just off Wells Hill Road. The property offers 3-Bedrooms, 3-Bathrooms, two living areas, a formal dining room, and a modernized kitchen, all characterized by abundant natural light and a welcoming ambiance. Two of the Bedrooms are en suite and the third utilizes the Hall Bath. The Family Room includes a separate Office Area, both of which are privately located on the side of the home opposite the Bedrooms - offering privacy and versatility in use. A covered breezeway provides a connection between the home's mudroom and an attached garage, which also features a screened porch at the back. This 1.3-acre lot offers usable land and mature landscaping in a sought-after area.

32 Red Bird Ln, Salisbury

3 Hay Meadow Ln, New Milford
$1,195,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24200363 MLS
Set on 2.48 gorgeous, level acres, this spacious 4-bedroom, 3.5-bath center-hall Colonial offers exceptional indoor and outdoor living. Hardwood floors, 9-foot ceilings, neutral finishes and generously sized rooms enhance the main level. The beautifully appointed kitchen features custom white cabinetry, an expansive granite island, tile backsplash, coffee bar, large pantry and casual dining area, with an easy flow to the impressive covered Trex deck. The adjoining family room showcases a dramatic vaulted ceiling, fireplace and custom built-ins. Formal living and dining rooms, a private home office with built-in cabinetry, large laundry room, powder room and access to the three-car garage complete this level. Upstairs, the spacious primary suite offers a walk-in closet and private bath with a double vanity, soaking tub and separate shower. Three additional bedrooms and a hallway full bath provide plenty of room for everyone. The walk-out lower level expands the living space with a large recreation area, kitchenette, full bath and separate mechanical and storage room. Outside, the expansive grounds create a private backyard retreat with a swimming pool, patio, treehouse, shed, garden area and koi pond. A truly special property with abundant space, versatility and impressive amenities inside and out!

3 Hay Meadow Ln, New Milford

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