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36 Deer Run Ln, Goshen
$1,150,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24185171 MLS
Come see this Private Retreat in beautiful, bucolic Goshen Ct. This home was built with the highest quality materials and is very well appointed throughout. The grounds are beautifully maintained with an inground swimming pool, pool house with a changing room, Tv, stereo and a kitchenette. The Pool area also boasts a fabulous outdoor built in BBQ Viking grill. There is a separate shed with electricity and security and a gorgeous solid mahogany deck. The house itself has central air, a custom gourmet kitchen, 9 foot ceilings on all floors and a solid mahogany front door. The lower level has a fully equipped suite with another full gourmet kitchen a gorgeous Tv room and possible bedroom. Perfect for an in-law or multigenerational living. The 3 car garage is heated with central vac, a large work bench and a wash sink. This house has a totally finished off lower level with in law possibilities. Come explore this beautiful estate and see how much it as to offer.

36 Deer Run Ln, Goshen
Winsted Norfolk Rd, Colebrook
$1,150,000
ACTIVE Status ⋅ 24089254 MLS
Intriguing Litchfield County / Colebrook CT Location: Great Opportunity to Own this Surveyed 124.92 Acre Site. Excellent Visible Corner Location. Lightly Wooded with Good Road Frontage. Potential as a Commercial / Residential Development, Private Estate Style Compound, Agricultural Use. Put your imagination to work here. Includes an existing Golf Driving Range at the Corner of Route 44 (Winsted/Norfolk Road) and Rock Hall Road. Property is Taxed under Forest Classification. Current Annual Real Estate Taxes $2,411.00.

Winsted Norfolk Rd, Colebrook
142 Stilson Hill Rd, New Milford
$1,149,900
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24167772 MLS
Set on an extraordinary 12.81-acre parcel, this one-of-a-kind estate offers a rare blend of privacy, luxury, and architectural distinction. Fully renovated from top to bottom, the home showcases exceptional craftsmanship with high-end, custom finishes and a design unlike anything you've seen before. Step inside to the main level where soaring ceilings, exposed beams, and walls of glass fill the great room with natural light, anchored by a striking fireplace. The stunning custom kitchen is both functional and beautiful, seamlessly connecting to the dining area-perfect for everyday living or entertaining. A unique lofted office space overlooks the main living area, adding character and versatility. The main level also features a thoughtfully designed full bathroom complete with a built-in sauna for a spa-like experience. The lower level offers a private retreat with a spectacular primary suite featuring a luxurious full bath, walk-in shower, and custom closet. A second bedroom includes charming built-in bunk beds, while the mudroom/laundry room is equipped with custom built-ins and a convenient bench. Step outside and enjoy resort-style living with direct access to an in-ground pool and spa, as well as an expansive deck ideal for entertaining or relaxing while taking in breathtaking long-distance views.

142 Stilson Hill Rd, New Milford
24 Roxbury Rd, Woodbury
$1,149,000
3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24209744 MLS
Private Litchfield County Retreat on Nearly 10 Acres Tucked among the picturesque hills of Litchfield County, along the desirable Woodbury/Roxbury line, this distinctive Colonial-Contemporary residence offers an exceptional combination of privacy, natural beauty, and modern comfort on nearly 10 acres. Surrounded by mature trees, lush landscaping, and vibrant plantings, the property enjoys a peaceful, secluded setting with the gentle sounds of Transylvania Brook flowing just beyond the backyard. A long, paved, beautifully illuminated driveway leads to the home, where an impressive double-door entrance welcomes you into a spacious foyer featuring a unique indoor water feature. The thoughtfully designed interior offers three generously sized bedrooms, two-and-a-half beautifully renovated bathrooms with luxurious Italian marble tile, and recessed lighting throughout. The inviting lower-level family room opens through French doors to an expansive stone patio and a heated, inground Gunite swimming pool, creating an ideal setting for relaxing or entertaining. A bright four-season sunroom captures sweeping views of the surrounding landscape, while a dedicated office provides a comfortable and private work-from-home space. The spacious primary suite is a true retreat, featuring a walk-in closet, Jacuzzi tub, private balcony overlooking the pool, and a versatile bonus room that can be customized as a reading room, home gym, nursery, or additional living space. Additional fe

24 Roxbury Rd, Woodbury
8 Burnham St, Plymouth
$1,149,000
7 Baths ⋅ ACTIVE Status ⋅ 24211113 MLS
Discover the potential of 8 Burnham Street, a unique mixed-use property offering both residential and commercial space in a convenient Terryville location. This property presents an excellent opportunity for investors seeking multiple income streams and long-term growth potential. Recent improvements include a new roof, new siding, and updated residential spaces, providing a solid foundation for the next owner. Conveniently located with access to Routes 6 and 72, local businesses, shopping, and area amenities. Existing occupancy with additional space offering lease-up potential makes this an attractive opportunity for an investor looking to expand a portfolio and capitalize on the versatility of a mixed-use property. Financial information and property details are subject to verification and buyer due diligence.

8 Burnham St, Plymouth
8 Burnham St, Plymouth
$1,149,000
10 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24210157 MLS
Discover the potential of 8 Burnham Street, a unique mixed-use property offering both residential and commercial space in a convenient Terryville location. This property presents an excellent opportunity for investors seeking multiple income streams and long-term growth potential. Recent improvements include a new roof, new siding, and updated residential spaces, providing a solid foundation for the next owner. Conveniently located with access to Routes 6 and 72, local businesses, shopping, and area amenities. Existing occupancy with additional space offering lease-up potential makes this an attractive opportunity for an investor looking to expand a portfolio and capitalize on the versatility of a mixed-use property. Financial information and property details are subject to verification and buyer due diligence.

8 Burnham St, Plymouth
67 N Main St, Kent
$1,139,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24179647 MLS
Steeped in history and radiating timeless elegance, this 1870 Victorian masterpiece stands as one of Kent's most grand and storied residences. Boasting a striking architectural facade, this magnificent home welcomes you into its grand entrance, featuring soaring ceilings and beautiful woodwork that flows throughout the entire property. Throughout its rich past, this versatile estate has been cherished both as a luxurious private residence and as a welcoming bed and breakfast. Today, it stands ready for its next chapter, offering multiple rooms across the premises and an incredible canvas for the next owner to bring their own vision and elevate it to its next level of brilliance. Location is everything. Situated right in the heart of the vibrant Kent Village center, this property offers unmatched walkability. Step outside your door and immerse yourself in the town's renowned culture-just a short stroll to world-class art galleries, gourmet restaurants, boutique shopping, local museums, and premier antiquing. Whether you envision a spectacular, expansive private compound, a boutique hospitality venture, or an elegant live-work space, the possibilities here are as vast as the home's rich history. Don't miss the rare opportunity to own a true piece of Kent heritage and define its next great era. Schedule your private showing today.

67 N Main St, Kent
11 Stone Fences Ln, Kent
$1,139,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24182669 MLS
This exquisitely appointed Colonial estate has the WOW factor! At its heart lies an opulant living room, where soaring cathedral ceilings meet a wall of grand windows, inviting the outdoors in, while a bespoke fireplace serves as a luminous anchor of comfort. The expansive, double height windows provide dramatic light to the open plan living/ dining/ kitchen. Miele and Bosch appliances are featured in the Chef's kitchen with a breakfast nook and a formal dining room adjoining. Transition effortlessly to the private, elevated deck; a serene sanctuary designed for seamless indoor-outdoor entertaining amidst tranquil vistas. Exceptional versatility defines the residence, featuring a main level Bedroom-ideal as a guest suite or private study; complete with an adjacent full bath. Retreat to the primary suite, a masterwork of design boasting vaulted ceilings, a statement chandelier and a cozy fireplace. This private haven further indulges with a dedicated seating area, an intimate balcony for morning coffee, full bath with double vanities, soaking tub, large stall shower AND an enormous dressing room. The two additional bedrooms are generously appointed with the convenience of walk-in closets and a Jack-n-Jill full Bath. The sun-drenched walk-out lower level is reimagined as the ultimate wellness retreat, featuring picture windows that frame the landscape. This multifaceted space offers a dedicated gym, spacious sauna and full Bath with rainfall shower for a true spa experience.

11 Stone Fences Ln, Kent
35 Emmons Ln, North Canaan
$1,135,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192466 MLS
CANAAN VALLEY HOME WITH POOL & STUDIO Indulge in Litchfield County luxury at this homestead, proudly situated in Canaan Valley, offering picturesque views of fields from both the front and back of this 4-Bedroom, 3-Bath residence, plus a Studio with its own Half Bath. This property features a spacious single-level living home, a separate studio, and an inground pool. The home has undergone comprehensive updates, presenting a modern and welcoming interior supported by robust system and structural enhancements, which include: well, septic, roof, siding, and heating and cooling systems, automatic generator. The inviting interior harmoniously blends indoor and outdoor spaces, ensuring a solid foundation for years to come, where cherished memories can be created in this new chapter. The desirable Canaan Valley area in Litchfield County is conveniently located just a short drive from Great Barrington as well as the lakes of Salisbury. Enjoy nearby skiing at Butternut and Catamount, hiking throughout the region, including the Appalachian Trail, and dining in the charming villages that decorate the area.

35 Emmons Ln, North Canaan
90 Sage Rd, Woodbury
$1,100,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24202077 MLS
From the moment you pull up to this House on the Hill, you will feel right at home. Built when homes were designed for gracious, comfortable living, it feels elegant yet relaxed, filled with color and thoughtful character. The beautifully crafted floor plan offers intimate parlors, three fireplaces, a generous kitchen, spacious living and dining areas made for gathering, charming Dutch doors, a cozy den, well-proportioned bedrooms, and an exceptional laundry room conveniently located on the same level as the recreation room with its own fireplace. Outdoors, a pool, professionally designed gardens, a growing room, and welcoming terraces create a setting to be enjoyed for generations. Every detail reflects a deep understanding of what makes a house feel like home. This seller is motivated!

90 Sage Rd, Woodbury
127 Steele Rd, New Hartford
$1,100,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24201058 MLS
Escape to the quiet elegance of Cobble Hill Farm, a 12.96-acre Greek Revival estate that perfectly balances 19th-century soul with modern luxury. Available for the first time in over 48 years, this mint condition historic gem features sun-drenched rooms, original wide-board floors, and four stately fireplaces. While the period character is meticulously preserved, the home is designed for today's comfort with a recently renovated kitchen, family room, and primary suite, plus central air in the east wing. This is the ultimate sanctuary for the modern homesteader, offering endless potential for an organic farm, vineyard, or equestrian facility. The property boasts a 1,950 sq. ft. vintage barn with 8-10 stalls and a classic hay loft, alongside a 4.5-acre meadow ideal for grazing horses or livestock. Enjoy the tranquility of your private 7,000 sq. ft. spring-fed pond, perfect for summer swimming and fishing. Additional outbuildings offer space for a creative studio, home office, or rec shed. B&B approvals are in place. Located 2 hours from NYC and Boston, minutes from Ski Sundown, West Hill Lake, and the Farmington River for kayaking and fishing, yet a world away from the noise. Cobble Hill Farm is a storied heritage estate where land and light unveil a sanctuary of timeless elegance. Get ready to write your life story at this quintessential retreat.

127 Steele Rd, New Hartford
159 Merryall Rd, New Milford
$1,100,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201121 MLS
Welcome to a truly special riverfront property where natural beauty, exceptional privacy, and country living come together. Nestled among mature trees and picturesque open pastures, this beautifully renovated home offers the perfect blend of rustic charm, peaceful privacy, and modern comfort. Originally custom-built in the 1940's, the home has been completely renovated and thoughtfully updated, with no expense spared. The property is an idyllic retreat for horse lovers, or anyone seeking a private country lifestyle surrounded by beauty. With its riverfront setting, wooded landscape, open pastures, and inviting country character, this is a rare opportunity to own a property that feels like a private sanctuary while offering all the comforts of a beautifully updated home. Highlighted features: 6.35 acres, private riverfront property, two barns, five stalls, tack room, fenced meadows, professionally landscaped, groomed trails, mint oversized, two plus car garage/workshop, hot tub, underground utilities, interior lot, extreme privacy, gated entrance. Only a five minute commute to the Town Green, shopping centers and all amenities.

159 Merryall Rd, New Milford
51 South St, Morris
$1,100,000
ACTIVE Status ⋅ 24195468 MLS
This South street property has been in the same family for 60 years. Opportunity to own a major piece of land in the center of Morris. Once a farm, now a young forest. Be close to several towns with privacy all around you. Some views, some wetlands, some road frontage on Benton Rd and substantial road frontage on South Street. Make yourself an amazing estate or potential for several homes. No subdivision plans, survey is being done now. Small house-800 sq. ft. on the property that is currently rented.

51 South St, Morris
37 Woodruff Ln, Cornwall
$1,100,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24193100 MLS
Situated along a picturesque country lane, this private 4 BDR home is a light-filled sanctuary offering the perfect blend of gracious and serene country living. A welcoming front porch invites you into a spacious foyer, flanked by a quiet home study on one side and a large, sun-drenched living room anchored by a cozy fireplace on the other. A bright kitchen effortlessly connects a formal dining room to an expansive family room with vaulted ceilings and a second fireplace, creating a seamless flow for entertaining. Outstanding indoor amenities include a private sauna near the kitchen and a dedicated staircase leading to a versatile upper-level study or exercise room. Another set of stairs from the main entrance leads to the second floor featuring 3 generous bedrooms and a luxurious primary ensuite retreat, complete with its own private dressing/reading room and a balcony overlooking the grounds and distant views towards the Catskills. Outside, a lovely wood deck on the main level leads to a swimming pool and a classic barn, making this secluded estate an extraordinary haven inside and out. Close to Cream Hill Lake, Mohawk Ski Area, hiking and biking trails, area private schools, farm to table restaurants, fly fishing on the Housatonic and other unique treasures in the Litchfield Hills. 2 hours to NYC.

37 Woodruff Ln, Cornwall
16 Gate Post Ln, Woodbury
$1,100,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24192457 MLS
Spacious Colonial in desirable Carriage Hills offers approximately 5,700 square feet of living space, including a walk-out lower level that is well suited for an in-law suite or au pair quarters. The main level features wood floors, formal living and dining rooms, an eat-in kitchen, a bedroom, a full bath, and a family room with a fireplace that opens to an oversized deck. Upstairs, you'll find three bedrooms, a full bath, and a spacious primary suite with a spa-like bath and loft area. The walk-out lower level includes three finished rooms plus a full bath, offering flexible space for guests, extended living, recreation, or work-from-home needs. The private backyard is surrounded by trees and accented with perennial gardens. NEW Roof June 2026. Located in Woodbury-one of Connecticut's most beloved small towns-the home is close to charming shops, antique stores, coffee shops, and restaurants, all just about 90 minutes from New York City.

16 Gate Post Ln, Woodbury
114 Wheeler Farm Rd, Watertown
$1,100,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24135269 MLS
Custom-Built Home on 1.45 Acres with Luxury Finishes & Outdoor Oasis in Watertown, CT!! Welcome to this stunning custom-built home offering over 4,600 square feet of beautifully crafted living space on 1.45 private acres. Designed with comfort and entertaining in mind, this home features 4 spacious bedrooms with the possibility of a 5th, along with 4 full bathrooms and 1 half bath, including a potential in-law suite setup. Step inside to find hardwood floors throughout, an open-concept layout, and custom stonework that adds timeless character across the property. The expansive kitchen, living, and dining areas flow seamlessly to create an inviting and functional living environment. Outside, enjoy the ultimate entertaining space with a custom patio, pizza oven, and firepit, perfect for gatherings year-round. 12X22 Shed with garage for extra storage. Additional highlights include 3 car attached garage, forced hot air heating, generous storage and closet space, flexible layout ideal for multigenerational living or home office needs. This one-of-a-kind property combines luxury, functionality, and craftsmanship in a picturesque setting. A true must-see!

114 Wheeler Farm Rd, Watertown
272 Main St, Plymouth
$1,100,000
2 Baths ⋅ ACTIVE Status ⋅ 24048427 MLS
Present use Custom motorcycle shop, Dealers license, Completely remodeled, new front sales room, Parts room, machine shop, repair shop, new roof, new gas main, new heating system, three garage door, one has dock, 2 half baths one in the sales room and one in back for staff, paved parking lot. Possible owner financing.

272 Main St, Plymouth
22 E Woods Rd, Roxbury
$1,099,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192986 MLS
*Completely reimagined from top to bottom, 22 E. Woods Rd. offers the rare combination of virtually new, low-maintenance living, nearly 7 acres of beautiful privacy and exceptional value. WITH JUST $7,395 in annual property taxes, the monthly cost to own and operate this home can be a fraction of what you'll find in many surrounding towns. Inside, gleaming hardwood floors, abundant natural light and an inviting open floor plan create a warm, comfortable atmosphere. The stunning custom kitchen features crisp white and natural-tone cabinetry, granite countertops and high-end stainless-steel appliances, flowing seamlessly into the living spaces anchored by a charming fireplace. The spacious primary suite offers a spa-like bath with soaking tub and oversized tiled shower, walk-in closet and separate flex space perfect for an office, nursery or dressing room. Three additional bedrooms share a brand-new full bath, while a bonus room over the garage-with its own staircase-offers even more flexibility. Outside, front and rear patios provide wonderful spaces for relaxing or entertaining while nearly 7 acres offer privacy and room to enjoy the outdoors. Freshly painted inside and out, with a new roof and driveway, this home is truly move-in ready and designed for worry-free living. Nearly a complete renovation, incredibly private, low taxes and a remarkably low cost of ownership-this is a rare opportunity to enjoy a nearly new home with the space and privacy you've been looking for!

22 E Woods Rd, Roxbury
385 Second Hill Falls Ln, Bridgewater
$1,095,000
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
280 East St S, Goshen
$1,095,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24189529 MLS
Galloway Farm is a one of a kind 1970's flat roof contemporary designed by Peter Dalton Morris that perfectly blends Breuer inspiration and modernist touches. On over 12 acres on a quiet road this property offers total privacy with open fields yet just minutes from the center of both Litchfield and Goshen. Drive up the driveway and around the circular drive and you're immersed in the properties natural and private beauty. Entering through the spacious foyer you're greeted by three walls of windows capturing the beautiful and tranquility of the property. The passive solar design creates a beautiful open living area yet defined spaces, the living room flows perfectly into the dining room and into the eat-in chefs kitchen with gas cooktop, wall ovens all while maintaining the views of the property. Cozy up by the fireplace with custom wood mantle then retreat behind it to the studio, a perfect place for capturing the beauty of the property. Walk up the open concept modern stairs to the second floor where you'll find a spacious primary suite with southern views and a wall of closets entering into the bathroom suite. There are three additional well appointed bedrooms, an office space plus a storage room all with beautiful hardwood floors complete the upper level. There is also a large full bath with tub and laundry on this floor. From every room you can enjoy views of the property with walls of windows, perfect in all seasons.

280 East St S, Goshen
321 Kent Cornwall Rd, Kent
$1,095,000
5 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24179592 MLS
Built in 1830 and set on 3.5 private acres abutting hundreds of acres of Connecticut State land, this five-bedroom Colonial is a rare find, a property where history, privacy, and natural beauty converge. Jaw-dropping sunset views set the tone from the moment you arrive. Inside, a recently updated kitchen anchors the main level, opening to a well-proportioned dining room made for long dinners with friends. The spacious living room, centered on a fireplace, is the kind of place you'll want to spend a winter evening. A main-level primary suite offers a private deck, a generous walk-in closet, and a spa-style bath, a true retreat within the home. Upstairs, four additional bedrooms share a full bath, with room for family, guests, or a dedicated workspace. The finished lower level adds a media room, home office, and laundry, keeping daily life organized and out of the way. Outside, the property comes alive. A side deck off the living room is perfect for morning coffee. The pool area, anchored by an impressive millstone table, is ready for summer entertaining. The perfect country retreat only two hours from NYC.

321 Kent Cornwall Rd, Kent
5 Lyric Ln, New Milford
$1,095,000
6 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24128830 MLS
Don't miss this newly listed one of a kind home nestled on 8.44 private acres with views so outstanding they could take your breath away. This 5700 plus sq. ft. home w/6 generous sized Brs, 5.5 baths is only the start. Its primary Br. 25X18 w/Fp, Lg. tiled bath w/jacuzzi & those mountain top views again then to a spacious walk/in closet. There are an additional 4 more bedrooms all with oak floors on this level. ( 2nd Floor ) The main level all with oak floors. (exception tile foyer) features a lg. country equipped kitchen w/all appliances, center island, granite counters, dinning area and more abutting 23' a family room a w/10 ft' ceiling & gas Fp.

5 Lyric Ln, New Milford
77 Deer Hill Rd, Colebrook
$1,080,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24044161 MLS
Enchanting Antique Dutch Colonial Estate with Carriage House and Barn. Nestled in a serene and private 51.2-acre haven, this stately home is a harmonious blend of historic charm and modern sophistication. As you traverse the meandering stone walls and explore the mix of sun-kissed meadows and whispering forests, you'll discover a world where time stands still, yet every modern convenience is at your fingertips. The property's outdoor allure is undeniable. Multiple walking or riding trails invite adventure, and the gardens, barn, carriage house and stone outbuilding offer endless possibilities for outdoor enjoyment. Step inside and be greeted by the warm embrace of rich hardwood floors, two fireplaces, French doors, and meticulously crafted woodwork that tell tales of yesteryear. The updated kitchen, equipped with a premium Wolf gas stove and a convenient butler's pantry, offers a perfect stage for culinary exploration. The living room, anchored by a cozy fireplace, formal dining room, and library, are infused with great natural light that dances across the spaces. The primary bedroom suite, a sanctuary of comfort, boasts its own fireplace, ensuring a restful retreat at day's end. Accommodate guests in style with four additional bedrooms, including a secluded guest room with a private stairway. Located in the heart of nature's playground in Litchfield county. Close to skiing, hiking, restaurants, and parks in Norfolk and Barkhamsted, and near the Farmington River.

77 Deer Hill Rd, Colebrook
18 East St, Bethlehem
$1,076,000
ACTIVE Status ⋅ 24195375 MLS
Rare Bethlehem Offering - Unzoned 2-Acre Property with Commercial-Ready 3,000 SF Barn + 1740s Residence A rare commercial/mixed-use opportunity in a town with no zoning restrictions, sited at Bethlehem, CT's famous blinking light with easy access to Washington, Litchfield & Woodbury. The centerpiece is a 3,000 SF barn, originally built out for a commercial dine-in bakery, with the significant infrastructure investment already complete: new roof, doors meeting fire & code, 4-phase electrical, roughed plumbing & HVAC, & poured concrete floors. No zoning to navigate, the possibilities are wide open - event venue, restaurant or bakery, artisan workshop, wellness retreat, boutique inn, or creative studio space. Adding to the flexibility is a fully preserved 1740s antique home (4 bedrooms, 5 fireplaces including a 12' hearth with beehive oven, walk-up attic, 9' basement ceilings that homes a Viessmann furnace & hot water heater) -ideal as an owner/innkeeper residence, on-site management quarters, or income-generating guest suites for a B&B concept. A separate milk house adds further flexible SF for guest quarters, staff space, or additional studio/workshop use. The 2-acre site includes a picturesque pond well-suited to event or hospitality use, mature ornamental plantings, a newly graded and re-graveled driveway (2023), and 75 ft of town-maintained sidewalk for pedestrian access. The groundwork for a next chapter - hospitality, culinary, or creative - is already in place!

18 East St, Bethlehem
18 East St, Bethlehem
$1,076,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193014 MLS
Seller incentive: $26,000 seller concession for offers received by November 1! Rare Bethlehem Offering - 1740s Antique + Commercial-Ready Barn on 2 Acres Welcome to a rare offering in the heart of Bethlehem, CT, sited at the town's famous blinking light with easy proximity to Washington, Litchfield & Woodbury. Dating to the 1740s, this sensitively preserved 4-bedroom antique is rich with period charm - 5 fireplaces, including a 12' hearth housing a beehive oven, historic detailing, a walk-up attic, and a basement with soaring 9' ceilings that homes a Viessmann Furnace and hot water heater. Thoughtful updates throughout make it a warm, move-in-ready home. The real story here is the barn: a striking 3,000 SF structure originally restored for a commercial dine in bakery, with the significant investment already behind it - new roof, doors meeting fire & code, 4-phase electrical, roughed plumbing & HVAC, and poured concrete floors. Reimagine it as an event space, artisan workshop, wellness retreat, or second residence - the foundation is already in place. A picturesque pond adds ambiance, ideal for commercial use or connecting the structures for potential multi-generational living. A charming milk house offers even more flexible space - guest quarters, studio, gym, or workshop. Grounds feature ornamental Japanese & red maples, flowering pear, cherry, birch & magnolia, plus a newly graded and re-graveled driveway (2023) and 75 feet of town-maintained sidewalk! A rare chanc

18 East St, Bethlehem
5 North St, Roxbury
$1,075,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24217126 MLS
Traditional four bedroom New England Colonial set on four level acres in the heart of Roxbury's Historic District. Welcoming circular peastone driveway to picturesque setting with a pond, gunite swimming pool, detached two-story studio/barn/workshop and two-car garage. This is classic center hall architecture with spacious rooms, hardwood floors, fireplace, large, bright eat-in kitchen, and a cathedral-ceiling family room offering generous space for recreation and entertaining. New roof in 2023. Comfortable as it stands, the home offers an excellent opportunity for updates and improvements to meet today's lifestyles. With its attractive grounds, versatile outbuilding, and desirable Roxbury location, this property offers a solid foundation and plenty of potential for its next owner.

5 North St, Roxbury
178 Carter Rd, Kent
$1,050,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24183167 MLS
Western-facing views from this homestead spanning over 50 acres in Kent. Immerse yourself in nature, where you can hike, mountain bike, cross-country ski, fish, or hunt on your own land! A delightful 1-Bedroom residence boasts an open-concept living and kitchen area that seamlessly transitions to an elevated deck, ideal for enjoying sunset mountain views. Enjoy the home just the way it is, expand it, or retain it as a guest house while constructing your dream home. A detached barn that includes a wood shop and three garage bays offers remarkable versatility. The Barn/Garage shares the same distant views as the main house and features a spacious layout that invites finishing touches. Envision this area overlooking the stunning sunset! Perhaps part of it could serve as a Home Office, a Gym, or your Recreation Barn. All these functions could be combined to still accommodate some Vehicle Storage bays! The potential is huge! This 50-acre property features diverse landscapes, including the slopes of a mountain that descend into a charming valley with a scenic brook. A former logging trail winds through open fields and established woodlands, ultimately reaching a brook that signifies the beginning of the famous Kent Falls. Located under two hours from NYC and just minutes from the villages of Kent, Cornwall, New Preston, and Lake Waramaug.

178 Carter Rd, Kent
331 Calkinstown Rd, Sharon
$1,025,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24211887 MLS
Nestled on 1.52 acres of meticulously landscaped grounds, this property features a Main Home along with a Guest Apartment, comprising 4 Bedrooms and 3.5 Baths. In addition to a gorgeous renovation that accommodates single-level living, this home features a new metal roof, Hardie board siding, new windows, a new septic system, and an automatic generator. Crafted for effortless living in the heart of Litchfield County, 331 Calkinstown Road exudes simplistic luxury. The Main Home is bathed in natural light and boasts a design that facilitates single-level living, highlighted by a luxurious Primary Bedroom Suite located on the First Floor. The well-appointed primary bathroom showcases an elegant aesthetic with double vanities, separate bath and shower facilities, and a dedicated dressing area. The primary Suite also includes a door that opens to the back deck, creating a private oasis. The kitchen, which features a seating island, is conveniently located next to the dining room that leads to the back deck, as well as a living room equipped with a wood-burning fireplace. On the upper level, two additional spacious bedrooms share a well-designed hall bathroom adorned with high-quality finishes. The 1-Bedroom Guest Apartment is positioned above the attached two-bay Garage, which can be accessed privately via an exterior door or through the Garage of the Main Home, providing flexible options for guests or a potential income source.

331 Calkinstown Rd, Sharon
770 Washington Rd, Woodbury
$999,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24218620 MLS
770 Washington Road, Woodbury, CT 06798 The Hazel Plain Schoolhouse: Historic Litchfield County Living Reimagined Steeped in rich local history, 770 Washington Road is a charming 1.09-acre Litchfield County property seamlessly blending 19th-century Americana with sophisticated modern luxury. Originally constructed in 1861 as the one-room Hazel Plain Schoolhouse, this landmark property has been lovingly restored, thoughtfully reimagined, and elegantly expanded into an inviting 3-bedroom, 4-full-bathroom home with custom millwork and wide plank flooring throughout. The Main Residence The home's appealing layout prioritizes privacy, comfort, and timeless New England character: * En-Suite Sanctuaries: All three bedrooms feature their own private, full en-suite bathrooms, offering an unparalleled layout for family and overnight guests. The primary bedroom is separated from the hallway by a large room that can serve as a dressing area, workout space, nursery or home office. The primary bedroom has a walkout to a beautiful multi-level stone and mahogany patio, perched under a canopy of mature trees. * Multiple Living and Entertaining Spaces: The home has a gourmet kitchen with custom cabinetry that opens to an inviting family room. A separate living room with a gas fireplace is perfect for cozy evenings. The dining room, lined with custom bookcases, is a wonderful gathering space for family dinners, holiday celebrations, and game nights. * Four Full Baths: A fourth ful

770 Washington Rd, Woodbury
380 Main St, Winchester
$999,000
5 Baths ⋅ ACTIVE Status ⋅ 24134408 MLS
Rare opportunity to own a well-established, 38-year restaurant with a loyal, built-in clientele and strong community presence. This fully turnkey operation offers exceptional versatility and income potential, featuring a spacious dining area with seating for up to 156 guests, plus an upstairs 20-seat bar-ideal for expanding service or hosting private events. The property includes five apartments, with three currently functioning units and two additional units ready for completion-perfect for added value and increased revenue. A dedicated 12-15 car parking lot, along with ample street parking, ensures convenience for patrons and tenants alike. Guests can also enjoy outdoor dining with seating for approximately 24, enhancing the overall dining experience. The basement area is fully equipped for dough preparation and offers abundant storage, supporting full-scale catering capabilities and high-volume operations. Endless possibilities await with this unique investment-ideal for restaurateurs or investors seeking a thriving business with multiple income streams.

380 Main St, Winchester

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