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49 South St, Washington
$899,000
2 Beds ⋅ 4 Baths ⋅ 24136464 MLS
Western Sunset Views, a short distance from The Mayflower Inn and Washington Green. Discover the ultimate renovation project or the foundation for your future estate. Situated in an elite enclave of fine homes, this 1890s Barn-style residence-complete with its signature silo and 1970s additions-awaits a visionary touch. Whether you envision a meticulous restoration of a historic showpiece or a chic, modern transformation, the potential here is as vast as the western horizon. The acreage has been strategically cleared to unveil stunning western exposures. The property is anchored by a mature landscape, featuring: Stone Terrace & Deck: Perfect for seamless indoor-outdoor entertaining. Rustic Writer's Cottage: A charming, detached retreat for creative pursuits or a quiet home office. Additional structures offering utility and historic character. The interior features an existing open floor plan, providing a fluid transition between the kitchen, dining, and living areas. Renovate the existing structure into a sprawling, personalized dream retreat that blends 19th-century charm with 21st-century luxury. The Guest House Strategy: Scale back the current residence to serve as a sophisticated guest house or secondary dwelling while you build a new primary manor. Bring your architect and your ambition-your slice of paradise is ready to be built. Town has 2 bedroom for septic size, there are two additional rooms that could be used as bedrooms. **Home requires a new septic.

49 South St, Washington
55 Good Hill Rd, Woodbury
$1,790,000
4 Beds ⋅ 5 Baths ⋅ 24136657 MLS
Located in picturesque Woodbury, voted Most Charming Town in CT by Reader's Digest in 2018, 2020 and 2024 and featured by Travel + Leisure among the 10 Best Places to Live. Experience the undeniable charm of this circa 1685 residence-one of the oldest continuously inhabited homes in the county. Thoughtfully restored and beautifully updated, this remarkable property blends centuries of character with today's modern conveniences. Inside, the open floor plan creates a warm and inviting flow, with three cozy sitting rooms surrounding the impressive central hearth. The chef's kitchen features a large center island, breakfast bar, and sweeping views of the expansive lawn-perfect for both everyday living and entertaining. Original details abound, including hand-hewn beams, wide king's board flooring, and the historic cooking fireplace that anchors the heart of the home. Recent upgrades include a new HVAC system with humidification and numerous other enhancements (see attachments for the full list). A new mahogany deck overlooks the level backyard, leading toward a picturesque bridge, sparkling pool, and inviting cabana. Two barns sit near the parking area-one offering garage space and the other ready for your imagination: ideal for a future guest house, studio, or recreation room, this barn has new propane heat, water and electric service. This extraordinary home offers the rare opportunity to own a piece of history-beautifully updated for modern living.

55 Good Hill Rd, Woodbury
114 Wheeler Farm Rd, Watertown
$1,100,000
4 Beds ⋅ 4 Baths ⋅ 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
5 Lyric Ln, New Milford
$1,095,000
6 Beds ⋅ 7 Baths ⋅ 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
439 Washington Rd, Woodbury
$289,000
2 Beds ⋅ 2 Baths ⋅ 24078648 MLS
Investors and Contractors take notice! This versatile office space located on close to 10 acres of rural Woodbury land is ripe with opportunity. The 1,920 sqft office can potentially be converted into a single family residential ranch overlooking the babbling Sprain Brook below. Across the brook, with road frontage and access off of Hoop Pole Hill Rd, lies the majority of the acreage with a dry, level, potential building lot. Convert office to residential, build across river and rent out office or use office and workshop yourself. There are 2, 7ft' garage doors leading to basement/workshop. The potential uses for this property are many! Sold As-Is, Where-Is, Buyer to do all due diligence regarding potential uses, Cash or Hard Money Loan preferred, no Seller Financing.

439 Washington Rd, Woodbury
50 Beardsley Rd, New Milford
$749,000
5 Beds ⋅ 4 Baths ⋅ 24126583 MLS
This spacious 5 bedroom, 3.5 bath colonial sits on a private interior lot of nearly 5 acres in the Sun Pond Woods development. The kitchen with its quartz counter tops, double oven, island and pantry make for great entertaining as it opens up to the large family room with fireplace. Also off of the kitchen is the sun room which has ac/electric heat and leads to the deck and the gas grill. appliances and mechanicals upgraded in 2021 were double oven, refrigerator, dishwasher, washer/dryer and the hot water heater. The well pump was replaced in 2023. The village center is less than ten minutes to enjoy the very walkable downtown. Visit the art deco movie house, restaurants, shops, the green or the playground at young's field and more. The fifth bedroom on the lower level could possibly be an in-law apartment.

50 Beardsley Rd, New Milford
77 Deer Hill Rd, Colebrook
$1,080,000
5 Beds ⋅ 3 Baths ⋅ 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
168 Cobble Rd, Kent
$1,650,000
4 Beds ⋅ 5 Baths ⋅ 24130930 MLS
Escape to this mountaintop retreat with sweeping, unobstructed views located off one of the most desirable scenic roads in the Litchfield Hills. Set in complete privacy, this four-bedroom home offers a perfect blend of comfort and sophistication with an open-concept layout designed for both relaxation and entertaining. The chef's kitchen, featuring a central island, flows seamlessly into a cozy reading nook with fireplace, a screened porch, and a dining area that opens to an expansive deck overlooking the breathtaking vistas. The spacious living room, anchored by a striking fieldstone fireplace, also connects to the deck and includes a charming home office. Upstairs, the primary suite offers a private balcony, spa-like bath with soaking tub, and walk-in closet. An additional ensuite bedroom, two more bedrooms with a shared full bath, and convenient laundry complete the upper level. The walkout lower level provides versatile living space, currently used as a media room and gym, and includes a full bath. Located just minutes from the shops and restaurants of Kent's vibrant village center-and only two hours from New York City-this property is the ultimate country retreat.

168 Cobble Rd, Kent
Lot 20 Bassett, Watertown
$749,000
4 Beds ⋅ 4 Baths ⋅ 24081427 MLS
ASK ABOUT HOW YOU CAN OWN THIS HOME FOR JUST 5% DOWN TOTAL! Privacy at its finest at this Custom built Ranch with exquisite architecture and expansive open floor plan! Plot plan comes with a designated area to have a potential built-in pool. This property is a ready to build in this established neighborhood. Attractive, flat, 1.14 acres, FULLY APPROVED building lot. Enjoy high-end finishes throughout. Boasting an open floor plan upon entering with cathedral ceilings and gas fireplace. Kitchen offers granite countertops, stainless steel appliances and large center island. Great room/living room leads out to screened in porch. Hardwood flooring runs throughout. Primary bedroom with two walk-in closets and on-suite bathroom, 3 additional spacious bedrooms, full bathroom, bonus room above garage, laundry, plus access to the 2-car garage. 4th bedroom can be turned into a study/office upon request. Enjoy living in Litchfield country within minutes to the center of Watertown and 15 minutes to the center of Litchfield. BUILD THIS ONE LEVEL CUSTOM RANCH OR YOUR HOUSE OF CHOICE!

Lot 20 Bassett, Watertown
138 Amenia Rd, Sharon
$6,995,000
9 Beds ⋅ 8 Baths ⋅ 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
685 Kent Rd, New Milford
$595,000
6 Baths ⋅ 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
28 Headquarters Rd, Litchfield
$985,000
3 Beds ⋅ 3 Baths ⋅ 24061045 MLS
Stimulating and easily managed home is perfect for weekending in an idyllic, small, historic village very close to big-time cultural, sports, and wildlife attractions. Living, dining, and kitchen areas are perfectly set up for entertaining. State-of-the-art appliances. Each bedroom has its own full bath and more. Multi-person ThermoSpa hot tub in enclosed (and air-conditioned) porch looks out on to quiet, private, and enchanting grounds.

28 Headquarters Rd, Litchfield
184 Fern Ave, Litchfield
$3,950,000
8 Beds ⋅ 10 Baths ⋅ 24100203 MLS
Come see this remarkably private property a stone's throw from the center of Litchfield. This stately home was built in 1992 and boasts over 10,000 s/f of finished space. The grounds are professionally landscaped and have a beautiful patio, pool and greenhouse. There are 8 bedrooms and 13 bathrooms along with a powder room . The sunny , modern, large eat-in kitchen open onto a patio, which then leads to the saltwater pool. A main floor guest bedroom suite with its own bathroom is an added convenience and can be a ground floor primary. There are lots of space for grand entertaining in the formal dining room, living room and great room. Plenty of cabinetry and shelves to display your treasures. You can warm yourself by the fireplaces. The master bedroom suite on the upper level has it all, walking closet, fireplace , sunroom and a large bathroom with steam shower and jet tub. 3 additional bedrooms round up the second floor, all with en-suite bathrooms. A separate laundry room is conveniently located on the bedroom level. The 3 floor has a loft and 2 additional bedrooms also with en-suite bathrooms.The lower level is fully finished and is a walk-out to the grounds. It also includes a wine cellar, a gym and a kitchenette. A separate apartement with a patio is located above one of the garage, which house 3 cars. Another garage for 6 cars is an additional outbuilding. Acreage is consisting of 3 separate parcels which are included w/sale.

184 Fern Ave, Litchfield
102 Melius Rd, Warren
$6,695,000
7 Beds ⋅ 7 Baths ⋅ 24129942 MLS
A rare opportunity to own one of Litchfield County's most exceptional legacy estates. Reverie Farm encompasses more than 101 acres across four separate parcels, offering extraordinary privacy, sweeping views, and endless possibilities as a country retreat or full-time family compound. The meticulously restored and updated 1799 stone and shingle residence, which features 7 bedrooms, 5 full and 2 half baths, intimate entertaining spaces, multiple fireplaces, and a 1-bedroom in-law apartment with both interior and private exterior access, is rich in historic character. Additional accommodations include a separate 3-bedroom, 2 bath guest house with its own driveway, and a separate 2-bedroom staff/guest apartment. Estate amenities include a heated gunite pool in a private garden space, tennis court, the renowned studio of Abstract Expressionist Cleve Gray and, across the driveway, his wife author Francine du Plessix's writing studio which has been transformed into a dance studio/entertaining space with a double height ceiling. Additional outbuildings offer exceptional flexibility for use as gathering spaces, remote workspaces, athletic facilities, studios, workshops, storage (wine, automobiles, and other collectibles), and other uses subject to local approvals. The open fields, woodland trails, ancient fruit trees, established gardens and stone walls create an extraordinary private setting with agricultural and equestrian potential.

102 Melius Rd, Warren
406 Wells Hill Rd, Salisbury
$8,875,000
6 Beds ⋅ 8 Baths ⋅ 24126255 MLS
Perched on more than seventy acres of rolling meadows and sculpted gardens, Linden Hill Farm stands as one of the most distinguished country estates in the region. A tree-lined allee of Linden trees leads to the Georgian Revival residence, built in 1929, where timeless architecture is seamlessly paired with modern luxury. The six-bedroom main residence opens with a dramatic double-height entrance hall that flows onto a stone terrace spanning the rear facade. Sunlight illuminates the grand living room, where French doors lead outside to a western-facing, glass-enclosed sunroom that overlooks the manicured boxwood garden and dining pavilion. The richly paneled library provides a private retreat, while the elegant dining room-with its own terrace access-offers an ideal setting for gathering with family and friends. At the center of the home, the chef's kitchen is outfitted with professional-grade appliances, a butler's pantry, and an inviting dining area that opens to the patio and kitchen garden. Upstairs, the primary suite is a sanctuary, complete with a fireplace, two dressing rooms, dual baths, a sitting room, and a terrace with views of the formal gardens. Additional guest suites with fireplaces and a separate wing with a game room ensure comfort and privacy for both residents and visitors. The estate's amenities are exceptional, a 60' x 30' swimming pool with bluestone surround, pool house, a lighted Omni-Turf tennis court, charming guest house,

406 Wells Hill Rd, Salisbury
77 Beaver Dam Rd, Salisbury
$2,995,000
1 Beds ⋅ 2 Baths ⋅ 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
55 Walnut St, Winchester
$410,000
5 Beds ⋅ 4 Baths ⋅ 24071827 MLS
Timeless Victorian with Endless Possibilities.Step into a piece of history with this stunning Victorian property, a landmark in the community and home to The Maloney Funeral Home since the early 1900's. Nestled in the TCR Zone, this versatile building offers a wealth of potential. The TCR Zone allows for accessory residential uses, community centers, family day care homes, single-family dwellings, and home farming. Additionally, with a special permit, the property may accommodate a variety of uses, including affordable housing, bed and breakfasts, boarding houses, congregate residences, convalescent/nursing homes, country inns, home occupations, mixed-use buildings, multi-family dwellings, outdoor private recreation and entertainment facilities, restaurants, schools, two-family dwellings, and places of worship. The first floor features spacious rooms that could accommodate a kitchen, pantry, dining room, formal living room, family room, and office. The second floor provides ample space for four to five bedrooms, while the third floor boasts a generously sized apartment, adding flexibility to the layout. A standout feature is the impressive 2,300 sq. ft. three-story barn/garage, offering abundant storage, workshop space, and potential for various uses. Whether you're seeking a unique investment opportunity or a property brimming with character, this exceptional offering is ready for its next chapter.

55 Walnut St, Winchester
34 Evergreen Passway, Morris
$525,000
2 Beds ⋅ 2 Baths ⋅ 24124552 MLS
Uber Chic Country Cottage on 5+/- private acres. Completely and meticulously renovated with all new: HVAC (including new owned propane tanks), plumbing, electric, insulation, doors, and windows with some historic exceptions and brand new roof. 4-Bedroom Septic. Open living/dining/kitchen with wood-burning fireplace, beams and new 5" oak floors lead to a terrace with a fieldstone fireplace & grill overlooking a level lawn. Kitchen with new 1940s retro appliances. First floor bedroom with cedar closet and private outdoor access. Full first floor bath. Upstairs, charming ensuite primary with pine floors and an adorable alcove for reading or sleeping. Potential building site for larger main residence. Private road. The perfect getaway. Must see!

34 Evergreen Passway, Morris
143 Whitcomb Hill Rd, Cornwall
$599,900
3 Beds ⋅ 2 Baths ⋅ 24127885 MLS
Toad Hall Offered for the first time in over forty-five years, Toad Hall is an utterly delightful 18th Century gem set on 11.6 acres in the heart of Cornwall Bridge, one of the most coveted areas in Litchfield County. This enchanting property features two barns, including a spacious main barn that has served as the studio of a renowned local artist. With its soaring space and rustic charm, it offers endless potential. Graceful stone walls meander through the property, surrounding the house and outbuildings, and weaving through the mature, thoughtfully landscaped gardens. The home itself is a true historic treasure, brimming with hand-hewn beams, original wood floors and classic moldings throughout. The entry foyer leads to a cozy living room on one side and a formal dining room currently used as a library with wood burning stove on the other. Upstairs you'll find four charming bedrooms and a full bath. The primary bedroom has sweeping views of the surrounding forest and mountains. The eat-in-kitchen opens to a delightful three season porch while a second porch at the back of the home overlooks a picturesque oasis. Extremely private, the property is bordered by large parcels of land providing unmatched tranquility and seclusion. Located in an area known for its natural beauty, farm to table dining, antiquing and shopping.

143 Whitcomb Hill Rd, Cornwall

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