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$3,999,000
6 Beds ⋅ 9 Baths ⋅ ACTIVE Status ⋅ 24206049 MLS ⋅ Great Elm BLDG.
This exceptional residence, one of Sharon's most historic properties, occupies much of the original 1812 Georgian mansion, home to a notable family, including William F. Buckley, Jr., for over a century. The layout is spacious & flexible, offering multiple options for purchase: 1) purchase in its current layout as a spacious, 6-bedroom residence, 2) divide the current 6-bedroom residence into two spacious 3-bedroom residences, 3) additionally acquire the north wing to recreate a more complete version of the original mansion for use as an expansive single-family residence, a family compound, or separate residences for rental income. The current 6,716 sq ft home has been thoughtfully restored & offers 6 bedrooms with primary suites on both levels, 7 full baths, and 2 powder rooms. The kitchen opens to a stunning library & informal dining area, complemented by formal living & dining rooms, a family room, office, gym, den, laundry room and 7 fireplaces. At the center of the home, a dramatic three-story 1250 sq foot glass atrium (the 1,250 sq ft is not included in the 6,716 sq ft) - enclosing the 1929 courtyard - creates a year-round living space that brings light & openness into the core of the home. This is estate living with the ease of a managed community. Enjoy beautifully maintained grounds with specimen trees & beautiful plantings. Amenities include: junior Olympic-sized heated pool, pool house, tennis court & separate paddle/pickle courts and more. More info below.

1 Great Elm Dr, Sharon
$1,595,000
5 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24203931 MLS
Welcome to one of New England's most architecturally significant and captivating properties, tucked away on 5.5 completely private, wooded acres in Cornwall Bridge, Connecticut. This iconic monolithic foam-dome residence breaks free from traditional design, offering a futuristic, sanctuary that blends seamlessly into its natural surroundings while providing exceptional structural strength and thermal performance. Inside, the sculpted, sun-drenched interior features continuous flowing lines, sweeping curves, cave-style built-ins, geometric window frames, multi-level lofts, peaceful bedroom suites, expansive living areas, and a spacious attached garage. The property offers 5 bedrooms, 41/2 bathrooms, a welcoming living room centered around a fireplace, and flexible spaces designed for privacy, comfort, and relaxation. The main residence is complemented by a separate guest unit, which is currently rented for $1,900 per month, offering an attractive income opportunity for the next owner. The crown jewel of this architectural marvel is its self-contained wellness wing, featuring a 40-foot heated indoor lap pool, integrated custom hot tub, dedicated sauna, and cold plunge pool-an exceptionally rare amenity in the heart of Litchfield County. A spectacular solarium with an adjoining stone patio provides a bright and inviting setting for entertaining, unwinding, or enjoying the peaceful countryside.

11 Day Rd, Cornwall
$319,900
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24201785 MLS
Enjoy beautiful water views and access to Highland Lake from this inviting home offering comfortable living spaces and desirable features throughout. The main level features a galley kitchen with plentiful white cabinetry, laminate flooring, refrigerator, dishwasher, and electric range. A convenient powder room and stackable washer add functionality. The spacious living room/dining area features wide-plank wood flooring, a small dining area, and a walk-out porch leading to a Trex deck-perfect for enjoying the outdoors and water views. A small first-floor bedroom offers flexibility for guests, an office, or additional living space. Upstairs, the primary bedroom is generously sized to easily accommodate a king-size bed and features wood flooring and propane-fired baseboard heat. The second bedroom also offers wood flooring, a large closet, ceiling fan, two large windows, and propane-fired baseboard heat. The full bathroom includes a newer vanity, stall shower, and laminate tile flooring. Additional features include forced-air propane heating on the main level, window air-conditioning units, a carpeted stairway, and two off-street parking spaces. A boat launch on Highland Lake provides an exceptional opportunity to enjoy boating and waterfront recreation.Book a showing today. This property will not last!

325 E Wakefield Blvd, Winchester
$350,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184049 MLS
This 4-bedroom, 1.5-bathroom single-family home is located at 34 Shelter Hill Ave, in the Oakville section of Watertown, in Litchfield County and was built in 1910. This home offers 1,314 square feet of living space with 7 total rooms and has been continually upgraded by the owner; however, they are no longer motivated to put more time into creating their vision (rendering included in photos). The home sits on a 0.65-acre level grass lot. It is served by municipal sewer, water and natural gas. There is an Invisible animal containment fence included and a storage shed. Great Bones, and some nice detail. Needs to be finished. This would be a good candidate for a renovation loan, 203K loan.

34 Shelter Hill Ave, Watertown
$600,000
9 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24195107 MLS
Rare mixed-use investment opportunity on over an acre along Woodbury's desirable Main Street South. This unique property features a seven-unit residential building, a detached garage with an additional apartment above, and a separate commercial building offering approximately 2,000 square feet with its own dedicated entrance and access. Three of the residential units are currently occupied, while the remaining units present an opportunity for renovation and value-add potential. The separate commercial building offers flexibility for a variety of business, office, or retail uses, creating multiple income opportunities on a single property. Properties offering this combination of residential and commercial space in such a prime Woodbury location rarely become available. Whether you're looking to expand your investment portfolio or reimagine a mixed-use property with significant upside, this is an opportunity not to be missed. Property is being sold as-is.

137 & 141 Main St S, Woodbury
$380,000
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194633 MLS
Prime Multi-Unit Opportunity on Corner Lot | East Side Torrington Maximize your equity or offset your mortgage with this versatile multi-unit property located on a prime corner lot on Torrington's desirable East Side, just seconds from Starbucks, dining, and commuter routes. The 3-bedroom main residence features warm hardwood floors, a classic brick fireplace, and a recently updated kitchen with white cabinetry and stone-look tiled floors, along with beautifully updated tile bathrooms. Detached from the main home is a spacious 2-car garage with a charming 2-bedroom apartment above, featuring its own recently updated kitchen with butcher block counters, an open living space, and a renovated bath-perfect for rental income, multi-generational living, or a private guest suite. Complete with a large yard and ample off-street driveway parking, this property offers exceptional flexibility and turnkey value in an unbeatable location.

Torrington
$499,000
5 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193729 MLS
A rare opportunity in one of Northwest Connecticut's most sought-after locations! Tucked away in a private, peaceful setting, this one-of-a-kind property offers endless possibilities with two separate homes on one parcel-ideal for a homestead, multigenerational living, income potential, or hobbyist retreat. The homes share a driveway with the southerly neighbor-PLEASE do not go without an appointment! The main Cape features 3 bedrooms, while the second home offers 2 bedrooms and an expansive great room. Beneath the second residence is an extraordinary heated garage with approximately 10-12' ceilings, 14' overhead doors, enhanced electrical service with abundant amperage, and space for an estimated 8-10 vehicles-perfect for car enthusiasts, contractors, woodworkers, collectors, or anyone needing exceptional workspace. Built with solid craftsmanship and owned by the same family for many years, the property is ready for its next chapter. While both homes require significant updating and will not qualify for government financing, the sweat equity potential is undeniable. Shared well and septic serve both homes, and major mechanical updates have already been completed.

1318 Litchfield Tpke, New Hartford
$3,950,000
4 Beds ⋅ 7 Baths ⋅ ACTIVE Status ⋅ 24192621 MLS
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury
$315,000
2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24189928 MLS
This is Litchfield living the way it was meant to feel-private, peaceful, and filled with character. Set against a wooded backdrop, 67 East Litchfield Road South welcomes you with classic brick architecture, a stone walkway, mature trees, and a generous yard with room to enjoy every season. Step inside to a bright, refreshed interior where wide-plank-style flooring, recessed lighting, and a comfortable open flow bring the living, dining, and kitchen spaces together. The updated kitchen is crisp and functional with white cabinetry, stainless steel appliances, and a tile backsplash. A beautifully refreshed bathroom features marble-look tile and modern fixtures, while the bedrooms offer hardwood floors, neutral finishes, and wonderful natural light. The lower-level garage and storage area provide the extra flexibility every home needs. Just minutes from Litchfield's beloved town center, shops, restaurants, outdoor recreation, and major routes-yet tucked away enough to feel like your own private escape. Classic New England charm, thoughtful updates, and a setting that is hard to replace. Property is being sold as is. Seller is open to concessions toward a new septic installation, subject to acceptable terms.

67 E Litchfield Rd S, Litchfield
$1,700,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24188553 MLS
55 Golf Drive, Norfolk, CT 06058. Handsome 1935 Craftsman-style house on 2.79 acres surrounded by quiet, private land. The layout is gracious, and the rooms are spacious. There are 3,681 square feet of living area, a large living room with central fireplace, an equally large screened porch with stone pillars off the living room, a dining room/library room with secret office, a renovated kitchen, a main bedroom suite on the first floor and 3 additional bedrooms plus 2 additional full baths, The sunny stone terrace is gently surrounded by flower garden beds. Updates complement the style of the house. The house is being offered furnished for $1,700,000 except for seller's art and personal items.

55 Golf Dr, Norfolk
$6,650,000
6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24186864 MLS
Known as "The Bungalow", this spectacular Tudor-inspired estate set on 43.8 private acres is one of architect Alfredo S.G. Taylor's finest designs. Built in 1908 for a Remington Arms heiress, the home seamlessly blends Gilded Age grandeur with exceptional modern luxury. The dramatic great hall features soaring 40-foot timber ceilings, a monumental stone fireplace, and exquisite fieldstone and half-timber construction. Thoughtfully updated throughout, the home offers a stunning new eat-in chef's kitchen complete with a butler's pantry and premium appliances, including a True glass-door refrigerator, Miele dishwasher, Wolf warming drawers, Sub-Zero wine and beverage refrigerator, and an exceptional custom range with handcrafted hood. The luxurious marble-clad bathrooms have been beautifully renovated with Kohler fixtures, while custom cabinetry, updated electrical systems, and meticulous craftsmanship elevate every space. Spectacular balconies and a wraparound veranda extend from the main living areas, providing breathtaking views across the surrounding landscape. Offering 6 bedrooms, 6 bathrooms, and 6,766 square feet of living space, the estate is set amid lightly wooded grounds with expansive northern vistas. Additional amenities include a guest house, barn, formal gardens, and a picturesque pond. Approached by a winding, newly improved drive, the residence sits atop a private ridge and culminates in a gracious porte-cochere, creating a sense of arrival rarely found.

310 Litchfield Rd, Norfolk
$365,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24184417 MLS
Welcome to East Lake Street at Highland Lake, where privacy, comfort, and lake living come together. Set back from the road on a private lot in the desirable First Bay area, this well-maintained lake-style home offers a quiet setting with seasonal lake views and refreshing breezes throughout. Offering 1,820 square feet, the home is listed as a 3-bedroom with a first-floor finished 4th room for added flexibility. The updated kitchen features quartz counter tops, stainless steel appliances, and ample cabinetry, with warm pine ceilings adding character throughout. Additional features include two full baths, first-floor laundry, newer windows, public water and sewer, natural gas, on-demand hot water, and a wood stove. Outside, enjoy a peaceful backyard garden and convenient rear access from Ontario Street. Located within one mile of local schools and a half mile of town, the home offers easy access to everyday amenities while maintaining a peaceful lake setting.

132 E Lake St, Winchester
$499,900
6 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24178149 MLS
Charming Multi-Family Property with steady income potential! Welcome to your next lucrative investment venture! Nestled on an expansive 1-acre lot, this multi-family property features 5 distinct living spaces, making it an ideal addition to your real estate portfolio. This property comprises 4 studio apartments and a spacious 2-bedroom apartment, catering to a variety of tenants and maximizing rental income. With a current monthly gross income of $4,200, you can enjoy steady cash flow while benefiting from an increasingly competitive rental market. Located in a desirable neighborhood with public water and access to public sewer, this property is perfectly positioned to attract long-term tenants. Its proximity to local amenities, schools, and public transportation enhances its appeal, ensuring high occupancy demand. Each unit boasts separate electrical meters, providing tenants with individual control over their utilities. The common laundry facilities in the basement offer added convenience for residents, further enhancing the livability of the space. Recently paved parking enhances accessibility for both residents and guests, while dual heating units ensures comfort during colder months. This property is not only inviting but also functional, providing a hassle-free living experience for tenants. It also comes with established tenants, solid rental history, and a reliable mechanicals, allowing you to step into a well-oiled investment without the headaches of initial setup.

205 Old New Hartford Rd, Winchester
$1,350,000
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 Mahoghany doors and ceiling fan, with a luxurious primary bath featuring a soaking tub, tile shower and dual sinks. The lower level includes a wine cellar, a full bath, a tandem two-car garage and a walkout patio. An elevator which serves all three 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
$534,900
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
$740,000
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24171297 MLS
UNIQUE OPPORTUNITY WITH MULTIPLE POSSIBILITIES!!! Located in the classic New England town of Bethlehem on 8.5+ acres this is your opportunity for unlimited potential. Build your own Private Estate, Family Compound, Multi-Family Investment, Business Operations with Offices and Storage, Horse Property, Farm and Possible Residential Development. There are two Residential homes and additional structures that can be re-fit to meet your needs. Existing Structures: Primary Residence - 1,876sf with 3 Bedrooms, 2 Bathrooms; Second Home - 1,100sf with 2 Bedrooms and 1 Bathroom and a 3 Car Garage with a Half-Bathroom. Two additional buildings for storage, hobbies, cars, boats, and all the toys you can fit. Current Use: the owner lives on the property and operates a pet rescue business and the existing Kennels can be very easily removed. There have been many upgrades to all structures on the property.

202 Crane Hollow Rd, Bethlehem
$549,000
11 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24166332 MLS
*PRICE REDUCTION* 150 Oak St. is a fully rented, rare, charming 1920's 5-family apartment home located in a beautiful residential neighborhood in Winsted/Winchester, CT. Old World charm with original woodwork, high ceilings, mostly hardwood floors, and hallways connecting the spacious rooms in 4 of the units -which feature 2 bedrooms and a dining room. The 5th floor is a 3-4 bedroom, 1 1/2 bath unit with electric H&HW. There is a 4-bay detached garage -some rented separately. 1 garage bay is rented to a non-tenant at $65/mo. A great investment opportunity! New since between 2021-2023: roof, 4 hot water heaters and 3 furnaces! Walking distance to Northwestern CT Community College and Downtown Winsted. Nearby shopping, indoor and outdoor activities. Easy commute to Rte 8 South and Rte 8 North to Western MA Pioneer Valley towns and the Berkshires. @ 25 miles to Rte 20 and Becket, MA. Several more miles on Rte 20 to the Lee Outlet and the MassPike!

150 Oak St, Winchester
$6,995,000
9 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24119336 MLS
Seize the rare opportunity to own Filston, one of Litchfield County's most distinguished Gilded Age estates. Designed in 1903 by renowned architect William Cromwell, Jr. for Mr. and Mrs. Romulus Colgate, this Neoclassical treasure seamlessly blends Italianate Renaissance Revival, Palladian, Neo-Gothic, and French Empire influences, creating a singularly breathtaking country estate. Every original detail is meticulously preserved in impeccable condition. Spanning just over 12,000SF of livable space, there are 10 bedrooms, 5 full bathrooms, and 3 powder rooms. Set across 106 acres on three distinct parcels, the property showcases a breathtaking landscape designed by Edward Hamilton Bell. Rolling hills, pristine woodlands, and majestic estate trees frame scenic equestrian trails, offering an idyllic retreat for nature lovers and equestrians alike. Complementing the main home is a historic 5,700-square-foot, three-story carriage house on its own dedicated parcel, adding versatility and charm to this extraordinary estate. Recent Upgrades * Complete electrical overhaul, with new wiring throughout the home and buried power lines from the road for enhanced aesthetics and reliability. * Landscape restoration, reopening original trails, removing dead trees, and treating the estate's magnificent mature trees to ensure their longevity. * Commercial-grade generator * New propane furnace and updated plumbing Serious inquiries only; proof of funds required.

138 Amenia Rd, Sharon
$595,000
6 Baths ⋅ ACTIVE Status ⋅ 24108370 MLS
Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of which has been used as office space. The residence part could use updates, or convert the entire building back to residential use. May be suitable for a home based business in R-40 zone. This is a listing where you need to see it to understand the property. Schedule your private showing right away!

685 Kent Rd, New Milford
$2,995,000
1 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24103122 MLS
A Premier Estate Parcel Ready for Immediate Construction This exceptional 33.9 acre property on Beaver Dam Road-one of the most scenic addresses in Salisbury-offers a rare opportunity to create a private estate of lasting beauty and value. Surrounded on two sides by protected land, the property enjoys a remarkable sense of privacy and quiet, while being just minutes from the town center. The land itself is a harmonious blend of open hayfields and mature trees, highlighted by a historic copse originally commissioned over a century ago by Frederick Law Olmsted, the renowned landscape architect of Central Park. The setting is both pastoral and refined, with long views, curated plantings, and a serene natural character that evolves beautifully through the seasons. Over the past two years, the current owners have undertaken an extensive series of improvements. A private homesite has been carefully positioned deep within the property, far from the road, offering the ideal location for a one- or two-story residence. A foundation has already been poured, and all the essential infrastructure is in place-underground electric, two wells, approved septic systems for both the main house and a separate carriage house, propane tanks, and whole-house generators-allowing for immediate construction.

77 Beaver Dam Rd, Salisbury

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