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$499,900
5 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24194726 MLS
Antique Colonial on 11+ Acres of Riverfront - Northville, New Milford. Set on over 11 acres of waterfront along the East Aspetuck River, this antique Colonial sits in the quiet, secluded Northville section of New Milford, just minutes from New Preston. A sparsely travelled, scenic unpaved country road leads you to the solitude you've been seeking - a project well worth your while. This 5-bedroom, 2.5-bath, 2,600-square-foot home is set back from the road to take full advantage of the river, the woods, and the tranquility so few get to enjoy in this corner of Litchfield County. She's in need of extensive renovation to bring her back to her original 1852 glory - but she'll pay you back doubly. Wide-plank flooring runs throughout, three wood-burning fireplaces anchor generously sized rooms, and the bones are all here. The property also includes a post-and-beam barn with 1,200 square feet across two levels - most recently used for storage and a workshop, but ready to become a guest house, detached garage, or both. Hundreds of feet of riverfront span both banks, connected by bridges, giving you land - and river - on either side. This home isn't for everyone. It's for those with vision, and those looking for a labor of love to capture the quiet, secret serenity of this special place. Never before on the market, this third-generation home is ready for its next caretaker.

28 Old Mill Rd, New Milford
$429,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24192079 MLS
The Case House offers a rare opportunity to own one of Barkhamsted's most distinctive historic homes. Nestled in beautiful Barkhamsted, with its highly regarded schools and low property taxes, this remarkable home has long been associated with one of the town's oldest families. Rich in character and thoughtfully maintained, it blends the craftsmanship of early New England with the warmth and comfort of everyday living. Original wide-plank floors, hand-hewn beams, raised-panel doors, and hand-forged hardware showcase the home's enduring character. The open-hearth kitchen, anchored by its original beehive oven, remains the heart of the home, while the spacious living and dining rooms provide inviting spaces for gathering with family and friends. Three bedrooms and one-and-one-half baths offer comfortable everyday living while preserving the home's historic character. The full walk-up attic is home to an original antique loom and other period artifacts that offer a connection to the property's past. Locally known as the "1759 House," The Case House continues to inspire curiosity about its rich history. Beyond the residence, a classic two-storey horse barn, detached three-car garage with an expansive workshop, garden shed, pump house, and tractor shed create a remarkably complete New England homestead.

55 Gavitt Rd, Barkhamsted
$1,076,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193014 MLS
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. 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 chance to own a piece of Bethlehem's history - the work is already done.

18 East St, Bethlehem
$485,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190973 MLS
This 1850 Antique home has been proudly cherished and meticulously cared for by the same family for 59 years. It is ready to be passed on to the next owner to enjoy all the beauty, cultural activities & outdoor recreation the coveted NW corner of Litchfield County provides. Proximity to the renowned Lime Rock Park Racetrack is sure to please automotive enthusiasts. Nearby prestigious private schools make this an ideal primary dwelling, or a weekend escape to rest & recharge. Upon entering the large living room, one immediately feels the warmth with wall to wall carpeting and a fireplace. An additional den/sitting room w/fireplace compliments the living area. A country styled, eat-in kitchen w/pantry area, tile floor, ample cabinets & large picture window is inviting. For more lively family gatherings, there is a formal DR w/french doors leading to a spectacular sun porch with walls of windows creating a tranquil, relaxing ambiance, flooded with natural sunlight. The upper floor has a primary bedroom with large, built in closets, a full bathroom with tub and a 2nd bedroom. The concrete floor basement has a full bathroom w/shower stall, utility sink & laundry with entrance to a one car attached garage. Oil steam boiler recently rebuilt & serviced regularly, chimneys repointed, heightened & capped, new water tank 2024. There is an outdoor storage shed on the property. Come see for yourself this special property & all it has to offer!

465 Lime Rock Rd, Salisbury
$4,200,000
6 Beds ⋅ 8 Baths ⋅ ACTIVE Status ⋅ 24192442 MLS
Nestled within the absolute privacy of the 1,700-acre Doolittle Lake Company woods, this beautifully maintained 100-acre estate across two parcels features a magnificent 5,670-square-foot 1780 Center Hall Colonial blending colonial and Art Deco charm. Painstakingly relocated in the 1930s by architect Robert Carrere, the home boasts grand reception rooms with wide red pine floors, two wet bars, and nine wood-burning fireplaces. Authentic 1930s nostalgia is preserved through functioning rotary dial phones and butler bells, while the gourmet kitchen is updated with a fireplace, custom cabinetry with antique glass, and a unique trout-cleaning fish sink on the back porch. The main floor opens to stone-walled perennial gardens and a custom, heated oval gunite pool, complete with a dramatic arched pool house featuring kitchenette, half bath, dressing rooms, and an outdoor shower. Upstairs, the primary suite offers a private sitting area, fireplace, and steam shower alongside three large ensuite bedrooms with fireplaces, and a playroom. A private ensuite studio bedroom sits above the heated three-car garage, offering perfect accommodations for staff or guests.

210 Doolittle Dr, Norfolk
$299,900
6 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24190507 MLS
6 bedroom 3.5 bathroom brick greek revival colonial next to town green w/4 bay detached garage & a 2 story brick carriage/barn house that has had recent masonry repairs. Fenced in yard, large back covered porch-master br suite w/walkin & full bath. Separate entranced apartment with kitchen,bath,lr/dr & 2 bedrooms this property will make a wonderful home or investment. All buyers and agents will be accompanied by the seller and will have to sign a hold harmless before entering the property. Cash buyers only

373 Main St, New Hartford
$1,725,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24190420 MLS
Timeless New England Charm on Coveted Wells Hill Road Dating to circa 1850, this beautifully preserved country home is a quintessential Lakeville retreat, blending historic character with the relaxed elegance of Litchfield County living. Set on two open, level acres and bordered by protected land, the property enjoys exceptional privacy, pastoral views, and a peaceful sense of permanence. Inside, the home offers four bedrooms and three baths, with warm, inviting spaces that celebrate its historic roots while accommodating modern living. Original architectural details, generous rooms, and abundant natural light create an atmosphere that is both welcoming and timeless. Outdoors, the property is designed for making the most of every season. An in-ground swimming pool anchors the landscape, while a charming gazebo provides the perfect setting for afternoon gatherings, evening cocktails, or quiet moments overlooking the expansive grounds. With protected acreage as your backdrop, the setting feels remarkably private and serene. Ideally located on one of Lakeville's most desirable country roads, 461 Wells Hill Road is just minutes from the village centers of Lakeville and Salisbury, Lake Wononscopomuc, hiking and biking trails, acclaimed private schools, and the vibrant cultural and culinary offerings of the Northwest Corner. Whether as a full-time residence or a weekend escape, this is a rare opportunity to own a classic Connecticut country property in an extraordinary setting.

461 Wells Hill Rd, Salisbury
$1,295,000
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
$2,300,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187424 MLS
The Dean House, a/k/a The Horsford Homestead, a/k/a The Howe's Home is arguably the oldest residence in Falls Village (Canaan), CT. The original structure was built in 1735, with a major, two story addition added in 1804. Many details have withstood the test of time, and this home is a stunning statement for any old-house enthusiast. If you envy the history as a preservationist, conservationist, or restorationist, you just found your personal Xanadu. From the original fireplaces and paneling to the structural "bones" in the attic and basement, all the right features are here, as spacious rooms, cozy environs, and heartfelt warmth are the mantras. Much of the original trim, flooring, doors, and moldings are prevalent, and that impact speaks volumes. The bathrooms are recently updated, and there are newer appliances. The cedar roofs are no more than 7 years old. The outdoor environment is lush and well maintained. There's a kidney shaped in-ground pool, beautiful gardens, and even a large flat lawn that once served as a home to a full-sized English croquet court. The large old barn dates well back in time, and there's a gazebo for quiet reflection and outdoor meals. Several other smaller buildings exist for all types of storage. And then there's the newer building (1997) - a combination of a two-car garage, a huge studio/workshop, a smaller storage room, and a roughly 1700 sq. ft. in-law apartment on the second floor.

167 Beebe Hill Rd, Canaan
$2,800,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24187539 MLS
The Dean House, a/k/a The Horsford Homestead, a/k/a The Howe's Home is arguably the oldest residence in Falls Village (Canaan), CT. The original structure was built in 1735, with a major, two story addition added in 1804. Many details have withstood the test of time, and this home is a stunning statement for any old-house enthusiast. If you envy the history as a preservationist, conservationist, or restorationist, you just found your personal Xanadu. From the original fireplaces and paneling to the structural "bones" in the attic and basement, all the right features are here, as spacious rooms, cozy environs, and heartfelt warmth are the mantras. Much of the original trim, flooring, doors, and moldings are prevalent, and that impact speaks volumes. The bathrooms are recently updated, and there are newer appliances. The cedar roofs are no more than 7 years old. The outdoor environment is lush and well maintained. There's a kidney shaped in-ground pool, beautiful gardens, and even a large flat lawn that once served as a home to a full-sized English croquet court. The large old barn dates well back in time, and there's a gazebo for quiet reflection and outdoor meals. Several other smaller buildings exist for all types of storage. And then there's the newer building (1997) - a combination of a two-car garage, a huge studio/workshop, a smaller storage room, and a roughly 1700 sq. ft. in-law apartment on the second floor. Approximately 30 acres of farmland is organic.

167 Beebe Hill Rd, Canaan
$2,395,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24178314 MLS
Introducing: Sage Hill The approach to this property is a slow one. Down a curved country road lined with evergreens that shade your path and allow dappled sunlight to light the way. A stone wall curves along the landscape, welcoming you to a drive anchored by a classic red barn. This 1890 farmhouse sits elegantly on a rolling lot, its large front porch making it easy to imagine long evenings watching the sun set with friends nearby. The foyer welcomes you with practicality and warmth. A bench for sitting while removing your boots, hooks for your coat. To the right is a sitting room with a wood-burning fireplace and large surrounding windows, making it a favorite room for humans and plants alike. To the left is the living room, with ample space for entertaining. Bookshelves line the far wall and a fireplace flanks them, making this a natural gathering spot after dinner parties. The dining room is a showstopper: soaring ceilings and detailed molding create a gracious space for holiday gatherings. The kitchen features a large walk-in pantry, a propane stove, a gorgeous decorative antique cookstove, and enough space for a dining table. The room opens beautifully to the pool area, with bluestone surrounding the space and a newly built gunite pool offering respite just steps away. The first floor also offers a full en-suite bedroom that could serve as the primary suite, guest quarters, or an in-law suite.

58 Dibble Hill Rd, Cornwall
$850,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24180161 MLS
Step back in time and own a piece of history with the distinguished Philo N. Hodge House, a remarkable antique home built in 1833 and proudly added to the National Register of Historic Places in 2024. Rich in character and historic charm, this unique property offers an opportunity to become the next steward of a truly special home. Bring your imagination and vision to this treasured historic property and make it your own. A welcoming foyer greets you upon entry and leads to a spacious formal living room featuring a classic fireplace. The sunroom is complete with a wood-burning stove. Upstairs, you'll find three bedrooms, including one pass-through bedroom that offers flexibility for a nursery, office, sitting room, or guest space. A full bath serves the second floor. The home's unique feature may be the finished walk-up attic, complete with a working sink and endless possibilities as an artist's studio, creative workspace, hobby room, or private retreat. Recent improvements include a professionally installed Connecticut Basement Systems waterproofing system, featuring a new sump pump and dehumidifiers to help maintain a clean, dry basement year-round. Filled with memories, history, and timeless architectural details, the Philo N. Hodge House is ready for its next chapter. Buyers are encouraged to conduct their own due diligence with the Town of Roxbury regarding any regulations, permits, approvals, historic preservation considerations, or future improvements to the property.

47 South St, Roxbury
$865,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24183601 MLS
Built in 1854, this 5.91 acre property offers an incredible value impossible to replicate today for the price. The property includes an Italianate stone home with an approx 675 sq foot retail/office room with a separate entrance at the driveway, a 28' x 53' post and beam barn with a full walkout lower level, a large pond, stone walls, incredible perennial garden surround, and a 21' x 45' accessory building with heat - great guest house or in-law potential. Inspired by Tuscan villas, Italianate style homes, usually square and symmetrical, were popular in the late 19th C. in New England. Park-like grounds; large pond has goldfish (see pics). The 3532 square foot main home has potential for an in-home business, or retail shop as it once was. Other potential uses in this highly-visible location include using the barn for farm animals and/or horses. Home has 4 bedrooms, 2 full bathrooms, 3 fireplaces, and approx 435 sq foot foot, renovated, eat-in, sunny kitchen with leathered granite counters and stainless appliances. New oil furnace 2026. Septic recently maintained (new pump, piping, and floats in 2022 by Garrity, no problems since). 50 gallon water heater Oct 2022. Substantial moldings and built-ins, front and back staircases, specialty stainless skylights, and a rooftop belvedere, which looks beautiful lit up at night, atop the well maintained copper roof. Minutes to three towns centers of Woodbury, Watertown, and Bethlehem. Guesthouse has elec.

1917 Main St N, Woodbury
$2,995,000
4 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24163576 MLS
Warren's Landing on the Pomperaug is an extraordinary estate where historic character is centered around a beautifully preserved 1890 Greek Revival residence. The home offers four bedrooms, timeless architectural details, spacious rooms, 4 fireplaces and custom built-ins. The impressive six-barn complex provides exceptional flexibility, featuring a retail shop, extensive equipment storage, a two-car garage, pool cabana and pool equipment building. A newly constructed temperature controlled 3,800-square-foot post-and-beam barn with a half bath and laundry room at the rear of the property further expand the property's possibilities. There are also an equipment/horse barn and riverside cabin. Outdoor living is equally remarkable with a stunning new in-ground gunite pool surrounded by lush landscaping. Designed for both relaxation and entertaining, the grounds include a custom "summer kitchen" with a European-style outdoor pizza oven, gas grill, and screened dining pavilion-perfect for hosting gatherings or enjoying quiet evenings. The 18.3-acre setting includes mature trees, open meadows, scenic walking trails, and frontage along the protected Pomperaug River, creating a private and picturesque retreat. Rich in history yet thoughtfully updated, this rare estate offers an exceptional combination of beauty, functionality, and enduring charm. A comprehensive list of recent improvements is available upon request. Buyer must do due diligence with the town for possible uses.

920 Main St S, Woodbury
$795,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24182169 MLS
Nestled on 1.13 picturesque acres between Salisbury and Sharon, this exceptional circa-1850 residence blends timeless New England character with modern comfort. Offering 4-5 bedrooms and 2+ full baths, the home features classic architectural details, two inviting wood-burning fireplaces, a newly installed propane-fired heating system, double-pane insulated windows, and a generator for added peace of mind. Designed for both relaxation and entertainment, the property boasts a spectacular 48-foot screened porch, a spacious second-floor bonus room, and an attached two-bay garage. Outside, a beautiful level lawn extends to approximately 378 feet of frontage along Salmon Kill Creek, complete with a private swimming hole. Ideally located just minutes from the shops and restaurants of Salisbury and Sharon, as well as Sharon Hospital, this historic and highly desirable area offers year-round recreational opportunities, including hiking, skiing, golfing, and access to Lakeville Lake. The property is also conveniently situated near several renowned private schools. Automotive enthusiasts will love the proximity to Lime Rock Park. A rare opportunity to own a classic country home in one of the Northwest Corner's most sought-after locations.

28 White Hollow Rd, Salisbury
$5,245,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24176398 MLS
"Hollow Farm" - An Expansive Historic Estate Reimagined for Modern Country Living Nestled in its own private valley, this 72-acre estate includes a Main House, thoughtfully updated and expanded in 2005; a charming Guest Bungalow; screened Gazebo perched over a pond; Pool Pavilion; Stables with caretaker's apartment; and a restored Barn. Comprised of multiple parcels, offering maximum privacy. The circa-1755 Main House features a dramatic great room with stone fireplace, adjoining chef's kitchen, and formal dining room. Additional main-level spaces include both a sitting room and a library with back-to-back fireplaces, plus a guest suite with full bath and sitting room. Upstairs, the primary suite offers a lofted sitting area with fireplace, as well as private deck, while two guest bedrooms share a hall bath. The lower level includes a wine cellar with cobbled floor and a gym. Outside, multi-level terraces showcase exceptional stonework, a fire pit, grilling area, pool, and spa. Two ponds and the sparkling Merryall Brook enhance the 18 acres of open land. Extensive landscaping compliments the natural beauty of the forested hills. As with the Main House, every outbuilding and outdoor space has been meticulously maintained. Although it feels a world away, this remarkable property is only 15 minutes from Kent, New Preston, and Washington. With its historic character, modern updates and expansive private setting Hollow Farm offers a rare opportunity for refined country living

57 Indian Trail Rd, New Milford
$775,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24138386 MLS
The Orton-Martin Homestead. One of Woodbury's oldest homes has been updated for today's lifestyle. History surrounds you with wide board flooring, library built-ins, two fireplaces and 1850 barn. This four -bedroom home offers spacious rooms, three finished levels and hidden delights. Enjoy picnics under the mature trees on your own fenced-in level yard. Sidewalks take you everywhere on Main St where you can enjoy the Library, antique and retail shops, schools, churches, great restaurants and coffee shops. Parks and the Senior Center are all nearby. Only 90 minutes to NYC. Named by Reader's Digest as one of CT most charming towns. Come call Woodbury home!

28 School St, Woodbury
$599,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24173902 MLS
*PRICE IMPROVEMENT* Tucked away on 1.07 private acres in one of the most desirable areas of Lakeville, this beautifully top to bottom remodeled 2 bedroom home offers the perfect blend of privacy, comfort, and convenience. Thoughtfully updated within the past three years throughout the entire property with unique, artistic touches offering both charm & functionality. The home features hardwood floors, a cozy LR fireplace, an inviting eat-in kitchen with all new appliances, a pantry annex, laundry in lower level 1/2 bath. Designed for easy, carefree living with many improvements - NEW: septic, well pump, pressure tank, water heater, electric panel, asphalt roof & accented metal roof's, Anderson window & doors, mini splits for A/C, driveway regraded, frenchdrain, gutters & too many upgrades to include. Must see to appreciate. Enjoy quiet mornings on the front porch and relaxing evenings on the back porch overlooking the private setting. A spacious garage with oversized door to accommodate an RV or boat which also includes an electric car charger, & workbench area/cabinets. Buried electric lines and a generator provide added peace of mind. Two additional outbuildings for storage. Ideally located to the Town Lake, gourmet restaurants, nearby Appalachian Trail, prestigious private schools, MetroNorth train, and easy access to The Berkshires, this special property offers country living with exceptional accessibility. A rare opportunity in one of the area's most sought-after location

203 Belgo Rd, Salisbury
$895,000
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24172742 MLS
Welcome to Bacon Pond House. A seamless blend of 19th-century soul and 21st-century luxury. Situated on over 3 acres, this antique Colonial has been thoughtfully revived to honor its heritage while offering every modern convenience. The interior, lovingly brought back to life, features wide-plank flooring and exposed hand-hewn beams that anchor the home's historic character. The rooms are designed for both intimacy and entertaining. A cozy sitting room and a dedicated office/library-complete with a classic fireplace-offer quiet retreats. For larger gatherings, the front-to-back living room, with windows on three sides, is bathed in natural light. At the heart of the home is the remodeled kitchen, which opens to the dining room centered around the original refurbished center core fireplace. Upstairs, four bedrooms await. The primary bedroom offers a new ensuite bath detailed with custom tile. The three additional bedrooms share a fully renovated bathroom with a soaking tub/shower combo. Thoughtfully curated, professionally designed interior furniture and fixtures are available upon request. The property has benefited from extensive renovations that include new bathrooms and kitchen, floor refinishing, a new well, upgraded septic, and more; a substantial list is available upon request.

253 Bacon Pond Rd, Woodbury
$3,500,000
7 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24169503 MLS
This stunning 1874 Federal house sits on a 3.93-acre lot and backs up to land-trust property. It was fully renovated and designed by Percy Steinhart, the design maven who created Stubbs & Wooton shoes. The estate contains a 6,641 square foot Main House, plus a wonderful Pool House and Carriage House. In the Main House, the spacious Entry Hall leads to the Living Room with a fireplace and a charming bay window. A large Library with a fireplace opens into a spacious Garden Room. The elegant Dining Room has a corner fireplace and double exposures. Adjacent is a gourmet Kitchen with a large island, high-end appliances, and a sizeable breakfast area with a spacious Cloak and Powder Room nearby. The front and back staircases lead to the second floor and a Primary Suite consisting of a large bedroom with a bay window and fireplace, and an elegant en-suite Bath. A second Bedroom with a fireplace is adjacent to the Primary. Two additional Bedrooms with en-suite Baths, and a Laundry Room, complete the second floor. On the third floor is a center gathering room plus two large Bedrooms and Baths. A large, unrenovated room has potential for use as an additional Bedroom, Gym, or Office. The Basement has a two-car garage with a Half Bath and generous storage rooms. The property is beautifully landscaped with a Croquet Lawn, a large pool, and Pool House with an outdoor fireplace for cooking, and a Greenhouse. The Main House and Pool House have updated HVAC systems with Central Air.

148 North St, Litchfield
$619,000
2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24171471 MLS
History unfolds at the original Lower Merryall schoolhouse. Reimagined and preserved as a unique home and infused with contemporary flair. The creative artisanal touches are evident throughout the home from beautiful finishes to the custom renovations. The first floor unfolds in an open layout, featuring dual sitting areas, a cozy fireplace, and a stunning kitchen complete with an island, concrete countertops, and a gas range. The contemporary color scheme against exudes a city vibe in the heart of the Litchfield Hills...just 2 hours from Manhattan. Wander outside to a spacious bluestone patio designed for entertaining, leading to a deck adorned with a pergola, chic black planter boxes, and an intimate gravel-based seating area. The yard boasts a striking creative studio, a charming greenhouse, raised garden beds, and a handy shed. The second level houses two cozy bedrooms with a shared bathroom, convenient washer and dryer, and a spacious loft area, perfect for relaxation or overflow for guests. This home is a rare find, a treasure for those who appreciate the allure of indoor/outdoor country living with a modern twist. Whether as a full-time residence or a part-time escape, this is a home that offers a unique and special lifestyle, ready to enchant its next stewards.

255 Aspetuck Ridge Rd, New Milford
$874,900
4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24165323 MLS
One of Woodbury's last remaining homes built in the late 1600s. This charming residence offers a unique blend of historic character and modern convenience, ideally situated for those who appreciate easy access to local shops, parks, and restaurants. The interior of the home boasts a rich history with exposed wooden beams, 4 fireplaces, and classic hardwood floors, creating an inviting and warm atmosphere. Outside, a private patio with an open fireplace provides an ideal setting for relaxation or entertaining, surrounded by lush perennial gardens. Adding to the property's versatility is a separate guest house. This additional structure is perfect for an artist's studio, offering a quiet and inspiring space for creative pursuits, or it can serve as a professional office, providing a dedicated work environment. Woodbury is known for its historical properties, with some homes dating back to the late 17th century. Main Street offers a charming experience with its antique shops, local restaurants, and vibrant Memorial Day parades. Woodbury is known for its picturesque downtown area, featuring beautiful streets and historic houses. As a gateway to the Litchfield Hills, the area provides access to a wider region known for its natural beauty and diverse attractions. Litchfield Hills are home to numerous wineries, forming part of Connecticut's Wine Trail,where you can enjoy tastings and scenic vineyards. The region also boasts farm-to-table restaurants that highlight local produce.

339 Main St S, Woodbury
$1,495,000
4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24067675 MLS
Rarely available. 1880 antique gem on 10 acres, with a first level primary bedroom and bath, situated on one of Bridgewater's most prestigious and quiet roads, offering a private setting. This residence masterfully blends historic character with an airy, open floor plan where the kitchen flows seamlessly into a spacious great room and a formal living room anchored by a classic fireplace. The interior living space consists of a main floor primary bedroom and bath, second level with 2 bedrooms and shared bath and a third level bedroom with it's own bath. The spaces transition beautifully to a 24 x 18 screened porch with slate flooring, opening onto a bluestone terrace. Perfect for entertaining, the terrace overlooks the pool and captures western exposures. The property is further enhanced by a two-story barn, providing ample space for storage or workshop. This is a unique opportunity to own a quintessential New England retreat in a premier location.

197 Skyline Ridge Rd, Bridgewater
$679,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24162576 MLS
Step back in time with this historic 1800s Colonial that retains its original character and charm while offering modern amenities, including an updated kitchen and bathrooms. The home features four bedrooms upstairs with wood floors, including a primary bedroom with an attached room currently used as an office. The main level with a den, living room with fireplace, dining room, and a mahogany-floor kitchen. Plus a mudroom/laundry room leading to the back patio. A large barn provides ample storage, and the property includes a 1,250-gallon 4-bedroom septic tank installed in 2008, a fully fenced backyard, and a 24-foot-wide new asphalt driveway. Recent upgrades include a new barn roof and framing, new 200-amp electrical panel and some wiring in the main house, insulated exterior walls, remodeled shower and fireplace, new wainscoting in the upstairs hallway, new glass backsplash in the kitchen, and restored original wood floors upstairs. Enjoy relaxing on the front porch or rear stone patio and take advantage of nearby hiking trails, parks, and open space, with Southbury, Bridgewater, and Washington town centers just a short drive away. Confirmed appointment required for showings.

216 Baker Rd, Roxbury
$985,000
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24159885 MLS
Own a Piece of Roxbury History! One of Roxbury's three oldest homes, this site has been cherished by seven generations of the Squire family. The existing antique home, while requiring reconstruction, has the potential to be reimagined as a charming guest house, preserving a tangible link to the past. Set on 12.7-acres this property and boasts breathtaking eastern views and the unique opportunity to create a stunning estate on land steeped in local heritage. A partially intact stone foundation (approximately 1500 sq ft) provides a solid base for this endeavor. Imagine building your dream home atop the hill, capitalizing on the panoramic vistas. A beautifully renovated barn, listed as historic landmark, adds further character and value. The property abuts Land Trust for hiking, ensuring privacy and natural beauty. Infrastructure is in place with a completed A-2 survey, installed driveway, and approved septic plans (3-bedroom for the antique home and 8-bedroom for a main residence). Electrical conduit is also installed to the proposed homesite. This land has subdivision potential and is ready for you to create a legacy of your own. **Note: Home is uninhabitable at this time. A full rebuild and renovation is required.

179 South St, Roxbury
$535,000
4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24159845 MLS
Beautifully maintained four bedroom home with two full baths located on the corner of Perry Street and Farnum Road, just a short distance to Lake Wononscopomuc and downtown Lakeville. First floor offers a spacious country kitchen with great counter and cabinet space & laundry, large dining area with bright living space and woodstove, an additional living room space, two large bedrooms with double closets, office and a full bath. Upstairs are two more bedrooms and a full bath with a claw foot tub. Very nice hardwood floors throughout this home. Walkout basement with storage and a one car garage. This home has private parking on both Perry Street and Farnum Road. Relax outside on the slate patio. Nestled in the Northwest Corner, this home is just a short distance from Lakeville Lake, downtown Lakeville, Salisbury and Millerton. All room sizes are approximate.

2 Perry St, Salisbury
$1,650,000
2 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24158676 MLS
31 Belgo Road offers a beautifully designed 2-bedroom, 2.5-bath main residence and a separate 1-bedroom, loft-style apartment above the garage, all set against spectacular views of Lakeville Lake. A new septic system was installed in 2024, which affords this home bedroom expansion capabilities. This upgrade is a significant value-add for potential logistics and future planning. Blending contemporary design with the charm of a classic New England home, this Litchfield County property embodies casual country living. The light-filled, open floor plan creates a seamless flow throughout the main living spaces. At the heart of the home is a state-of-the-art chef's kitchen with top-of-the-line appliances, opening effortlessly to a sunroom ideal for dining and gathering. The adjacent family room features soaring 13-foot ceilings, while the formal living room is highlighted by a striking floating staircase leading to the upper-level ensuite bedroom. The first-floor primary suite serves as a private sanctuary, complete with an ensuite bath, walk-in closet, and multiple windows overlooking beautifully terraced stone gardens. The second ensuite bedroom, accessed by the dramatic floating staircase, provides a comfortable and private space for guests or family. Outdoor living is equally impressive, with a bluestone patio designed for entertaining and featuring a wood-burning fireplace.

31 Belgo Rd, Salisbury
$1,750,000
3 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24145140 MLS
"The Taconic School House" 1st Time on the Market in over 25 Years. Special Salisbury Location Set Amongst Large Estates & the Twin Lakes in the Coveted Taconic Section of Salisbury CT. A Gracious & Magical Paneled Room with Large Fireplace Welcomes All to this Whimsical & Eclectic c1890 Home. 3-4 Bedrooms, 4 Full Baths. Lower Level Acts as Pool Cabana & Contains Glass Enclosed Siting Room, Secondary Kitchen & Full Bath. Fenced Gunite Pool. Impressive Limestone Foundation is on Full Display.

552 Twin Lakes Rd, Salisbury
$699,900
3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24139265 MLS
This authentic antique home is ideally located on one of Bethlehem's most desirable country roads, surrounded by other elegant historic properties. Meticulously maintained, it showcases true period charm with spacious rooms, high ceilings, original wide-board floors throughout, and a grand central chimney serving three fireplaces. The main level is perfect for both daily living and entertaining, featuring a large eat-in kitchen, a cozy wood-paneled study with built-in bookcases and fireplace, an inviting living room with fireplace, and a gracious formal dining room-all generously proportioned for comfortable gatherings. Upstairs you'll find three well-sized bedrooms, a full bathroom, a large walk-in attic over the kitchen that's already framed and ready to become a luxurious primary suite, plus a separate walk-up attic with plenty of headroom for additional finished space. The beautifully landscaped grounds include a sweeping level lawn, a fully approved extra building lot with its own private driveway, and a handsome post-and-beam barn offering ample room for vehicles, workshop space, and storage. Move right in and enjoy this classic beauty as-is, or take advantage of the rare opportunity to expand, add a guest house, or create a family compound.

114 Carmel Hill Rd N, Bethlehem
$1,995,000
4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24136657 MLS
Step into History with Modern Comfort 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

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