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142 Interlaken Rd, Salisbury
$2,740,000
4 Beds ⋅ 4 Baths ⋅ 24178309 MLS
From the moment you turn down the long, meandering driveway, you can sense you are approaching something truly special. Arriving at Water's Edge, on 13 private acres, the home with its classic barn, charming outbuilding, and circular drive initially presents a modest front, but an incredible surprise awaits. The true gravitas of this property reveals itself the moment you step outside. The home is perfectly oriented to draw your eye to the magnificent backyard, where the pristine waters of Lake Wononpakook serve as your direct backdrop. Here, a private dock stretches out into the water as kayakers gently float past. Transitioning inside from the water, a beautifully rounded, private stone patio leads into a quintessential screened porch, the exact spot where, let's be honest, you'll be spending most of your evenings. Inside the main residence, the exceptional level of care and detail that went into its construction is immediately apparent. Built just 30 years ago, which we affectionately refer to as a "new build" here in Litchfield County, the interior offers a highly flexible floor plan. The main level features light filled common spaces, including a dining room and a living room, both oriented to frame the lake views and anchored by a cozy wood-burning fireplace. The kitchen is a natural gathering hub, complete with ample counter space for meal prep and a generous breakfast bar for entertaining.

142 Interlaken Rd, Salisbury
99 Washinee Heights Rd, Salisbury
$2,702,000
3 Beds ⋅ 3 Baths ⋅ 24162128 MLS
Arrive at The Lake House and a profound sense of peace immediately washes over you. Situated on a quiet, exclusive street along the shores of Lake Washinee in Salisbury , this contemporary estate offers a truly private retreat. With 300 feet (+/-)of pristine water frontage, the property looks out over the quiet lake to the Taconic Range, offering spectacular, western-facing sunset views. It is a setting so serene that graceful swans are frequently seen gliding across the water, while the neighborhood itself remains incredibly peaceful, disturbed only by the occasional resident walking their dog. Inside, a dramatic entrance welcomes you into a breathtaking foyer that flows into an awe-inspiring living room. Built in 2003, the home's soaring post-and-beam architecture beautifully weaves the natural outside world into the interior. Natural light streams through an expansive wall of glass, illuminating the hardwood floors and built-in window seats. The perfect spot to settle in with a book on an autumn afternoon. A stone woodburning fireplace anchors the space, promising cozy winter evenings. This spectacular room transitions seamlessly into a formal dining room with high ceilings, and an expansive kitchen designed to maximize the sweeping views of the lake and mountain range. The main floor was thoughtfully designed to capture lake views from almost every room.

99 Washinee Heights Rd, Salisbury
Roxbury
$2,700,000
5 Beds ⋅ 6 Baths ⋅ 24093019 MLS
Tranquility awaits down this long paved driveway in Northern Roxbury. Complete privacy with spectacular gardens, pond and orchard surrounded by dramatic rocky outcroppings. This stone and stucco home features large eat-in kitchen, formal dining and living rooms, and a spacious media room. The main floor primary suite includes a fireplace, office space, and large walk in closet. There is an addl guest room on the main level, perfect for nursery or in-laws.3 bedrooms/2 baths on the second level. Lower level game room has full bath and can be used as a 6th bedroom. Gunite heated pool with stone terraces incorporates room for relaxing and dining pool side. 3 car garage has unfinished space above which could be finished to an apartment or studio. Multi zone stereo system. Just 5 minutes to Washington with chic shops, farmer's market and

Roxbury
430 Milton Rd, Goshen
$2,690,000
6 Beds ⋅ 9 Baths ⋅ 24111678 MLS
12-Acre Lakefront- Classic New England Estate. 100 ft. frontage directly on Woodridge Lake, with rights to build a boat dock, deck and cooking area at lake's edge and enjoy water activities and picturesque views. Discover the epitome of charm and grace in this magnificent home with 3 wood-burning fireplaces. 13 total rooms including 7 bedrooms with 7 full & 2 1/2 baths. With two ponds, open meadows and lawn, the property offers tranquility and privacy. Be immersed in a private outdoor oasis featuring an exquisite Gunite pool & spa with a mesmerizing 6' infinity waterfall. Enjoy cozy evenings by the outdoor stone fireplace. Bordering both Mohawk State Forest (4,000+/- Acres) and Wyantenock State Forest (4,000+/- Acres), the property seamlessly merges with the beauty of nature, providing unparalleled serenity and assuring forever preservation from development. Once home to five horses, the horse barn and paddocks add a touch of rustic charm. Ideal for horse enthusiasts. Ski at nearby Mohawk Mountain Ski Resort (with Night Skiing), a mere 8-minute drive. Rare Offering with Potential Waterfront Building Site on Quiet Country Road yet, 10 minutes to Litchfield Town Center and its world class restaurants, shops and services.

430 Milton Rd, Goshen
47 North St, Litchfield
$2,600,000
4 Beds ⋅ 5 Baths ⋅ 24166876 MLS
On nearly an acre in the Borough of Litchfield, the 1775 Benjamin Tallmadge House is a rare offering in the Litchfield Historic District. A decade of museum-quality stewardship under the current owners has produced one of the most thoughtful restorations ever undertaken on a North Street residence, with every original architectural detail preserved. This antique Colonial blends preserved character with thoughtful updates, including original wide-board pine floors, plaster walls, refurbished Indian shutters, 10 fireplaces, and a chef's kitchen with soapstone counters, La Cornue range, butler's pantry, and built-in banquette. Four bedrooms are joined by a third-floor den currently configured as a 5th bedroom.The primary suite features a 2026 expanded glass-and-tile shower, walk-in dressing room, and cedar closets. Grounds by Michael Trapp include a 44-foot gunite pool, planted rooftop deck with 10-foot spa, tea house, gazebo, gas fire pit, and attached 3-car garage. This is the rare offering where architecture, national history, and daily livability all carry equal weight - a Georgian landmark with Revolutionary War provenance, museum-quality restoration, and a Trapp landscape compound, presented in turnkey condition for its next generation of stewardship.

47 North St, Litchfield
277 Painter Hill Rd, Roxbury
$2,547,500
3 Beds ⋅ 3 Baths ⋅ 24138574 MLS
This beautifully renovated 1911 colonial blends timeless charm with modern comfort in one of Roxbury's most desirable locations. The main residence offers luxury living with 2-3 bedrooms, a media room, gourmet kitchen, formal dining room, and a screened porch. The newly built guest house includes 2 bedrooms and a spacious game room/cabana with fireplace. Enjoy Summer entertaining on the covered porch with outdoor fireplace overlooking the heated gunite saltwater pool, scenic views, and expansive level lawn. The property features a two-car garage and borders a major estates and conserved land, ensuring privacy and beauty in an exceptional setting. Just minutes to the Mayflower Inn/Spa and chic shopping/dining in Washington and Woodbury.

277 Painter Hill Rd, Roxbury
9 Overlook Dr, Salisbury
$2,540,000
4 Beds ⋅ 5 Baths ⋅ 24150334 MLS
Experience the refined simplicity of modern living in this beautiful and recently renovated 4 BR, 4.5BA home situated off Belgo Road in Lakeville, CT. The southern exposure bathes this 5.7-acre property in light, perfectly showcasing each living area and highlighting the breathtaking mountain views. Large windows throughout the residence invite the natural beauty inside, enhancing the interior's sleek lines and high-quality finishes. The main level boasts an open floor plan that features a kitchen, along with a dining area and a living room accentuated by a tall central fireplace, flanked by two-story windows and sliding doors that lead to the back deck. A spacious Main Floor Suite with sliding doors leading to the back deck can function as a primary bedroom, office, or guest suite. The second-floor landing showcases a striking catwalk balcony that overlooks the main living spaces below and connects three en suite bedrooms, one of which includes a generous Primary Bedroom Suite that mirrors the layout of the suite on the first floor. The two bedrooms with southern exposure enjoy mountain views from their own private balconies.

9 Overlook Dr, Salisbury
Roxbury
$2,501,000
5 Beds ⋅ 6 Baths ⋅ 24122044 MLS
Exquisite Country Estate in Roxbury Nestled on 42 private acres in the heart of Roxbury, this spectacular shingle-style architectural masterpiece offers an unparalleled blend of sophistication and serene country living. From the moment you meander down the picturesque drive, you'll know you have arrived at your forever home. Designed for both grand entertaining and intimate daily life, the home's beautiful open spaces are bathed in natural light. Every detail has been meticulously crafted to create an atmosphere of refined elegance and comfort. This residence features five spacious bedrooms, six luxurious baths, and four fireplaces, each adding a touch of warmth and classic charm. Outdoor living is elevated to an art form here. The award-winning infinity pool and spa appear to spill into the professionally designed landscape, which seamlessly blends with the natural wooded surroundings, ensuring complete privacy. A grand stone terrace with a fireplace and a sprawling covered porch provide the perfect settings for memorable outdoor gatherings, dining, and relaxation. This estate truly offers the best of both worlds-it feels a world away from the hustle and bustle yet is conveniently located close to everything. The property consists of three separate parcels and benefits from low Roxbury taxes, adding to its appeal. This is more than just a home; it's a lifestyle. We invite you to plan extra time for your private showing to fully appreciate the except

Roxbury
Norfolk
$2,500,000
6 Beds ⋅ 4 Baths ⋅ 24189146 MLS
Resting on a knoll overlooking private Doolittle Lake is a one-of-a-kind Doolittle "Camp" designed by Alfredo Taylor and built in 1936. The pictures tell the story but here are some details. The house sits on 3.4 acres and has 313 feet of lake frontage. There are 3,237 sq. ft. of living area, a large central living room with fireplace, a lakeside stone terrace, a lovely wood-paneled dining room, a renovated kitchen with large adjacent pantry, main bedroom with fireplace, 4+ additional bedrooms, 3-4 full baths, and many closets. There are wide board floors, vaulted ceilings, extra tall windows and original wood paneling and cabinetry in various rooms. The systems are updated for the most part and the house is true to its original design and in lovely condition.

Norfolk
60 Selleck Hill Rd, Salisbury
$2,500,000
3 Beds ⋅ 4 Baths ⋅ 24154000 MLS
Follow the meandering driveway to Ravenswood. Featured in Architectural Digest (2020), the home was built by design-driven, eco-conscious architects StoneFox, known for contemporary architecture with a strong sense of place. Their approach emphasizes clean, simple design and a sensitive connection to nature and the environment. As you enter, you are struck by the soaring living room ceilings. Large windows pull your eye out to the landscape and the heated gunite pool that sits seamlessly just beyond. The kitchen is anchored by a modern marble island, the centerpiece of the room. Appliances are integrated with custom European bleached white oak cabinetry for a seamless look, finished with Carrara marble. The den is conveniently located on the first floor and features large glass doors to provide privacy when required. A bedroom suite and a powder room complete this level. Climb the solid oak staircase to the second floor to find a modern, light-filled landing large enough to accommodate an office. The spacious primary suite welcomes the outside in with a large picture window that frames the New England forest. Your own private retreat. The primary bath features a large soaking tub that overlooks the property, allowing you to take in the serene, quiet landscape. A double vanity and large marble shower set the tone for this modern sanctuary.

60 Selleck Hill Rd, Salisbury
370 Northrop St, Bridgewater
$2,500,000
3 Beds ⋅ 6 Baths ⋅ 24111140 MLS
French Chateau in Bridgwater. Considered one of the most coveted streets in the surrounding areas. Stone wall with gated entrance. Double height foyer.Atrium living room with wall of French doors and marble fireplace. Sexy bar leads to the library. Open & gourmet kitchen with fireplace and butler's pantry. Formal dining room. First floor primary suite with marble bath and massive walk-in closet. Billiards room and 2 half baths. Upstairs guest rooms are both with en-suite baths. There is a perfect spot for a 4th bedroom ready for your ideas in the lower level or finish off a portion of the barn/garage. Fabulous terrace is accessed from most every room overlooks the lush grounds, Gunite pool with spa, cabana and views. Complete privacy on a coveted & prestigious street with a majestic presence. The lower level with an additional 1/2 bath and 4 car parking spaces. Additional detached garage with 4 additional bays and one oversized for a boat and an upstairs loft that could be finished. The boat launch to Lake Lillinonah is just at the end of the street. Generator. The property has been meticulously maintained and is magical. This is a true, trophy property not to be missed. Quintessential New England at it's best.

370 Northrop St, Bridgewater
89 Belgo Rd, Salisbury
$2,495,000
3 Beds ⋅ 3 Baths ⋅ 24173402 MLS
Located on desirable Belgo Road in Lakeville, this thoughtfully renovated Cape-style home blends warmth, comfort, and functionality in one of the area's most sought-after settings. Enter from a pea stone U-shaped drive across the deep front porch into the three-bedroom, two-and-a-half-bath residence. The home includes a separate main-floor primary suite with a walk-in closet and bath with a soaking tub and separate shower, while upstairs offers two additional bedrooms, a full bath, a sitting room, and office space. A finished studio above the heated two-car garage provides flexible space for work, exercise equipment, or creative use. Wood floors run throughout the home. The light-filled living room with a fieldstone fireplace opens to the rear patio and to the dining area and kitchen featuring granite countertops, a farmhouse sink, and custom cabinetry. French doors lead to a screened porch overlooking the grounds. Adjacent to the kitchen is a large pantry with a washer/dryer, refrigerator drawers, bar, wine storage, and additional storage. A custom mudroom includes tiled floors, built-in bench seating, and cubbies. Radiant heat adds comfort throughout much of the home. The fenced 20x40 heated gunite saline pool area includes an outdoor shower and potting shed, creating a private setting for summer entertaining. Beyond the pool are fenced raised garden beds, a firepit, and manicured trails winding alongside a seasonal stream.

89 Belgo Rd, Salisbury
96 Kinney Hill Rd, Washington
$2,425,000
4 Beds ⋅ 5 Baths ⋅ 24148829 MLS
Private oasis in a coveted estate area with turn-key residence, salt water pool and guest house. Set on 10+ park-like acres, the main house includes 4 bed/4.5 baths, wrap around porch and a desirable open floorplan for modern living. The great room and eat-in kitchen flow seamlessly and host a stone fireplace, newly refinished flooring, dining room, and a media room/office. Renovated kitchen with many storage nooks, custom cabinetry, walk-in pantry and spacious breakfast nook that seats 8. Wake to views in the primary bedroom which boasts a vaulted ceiling, 2 walk-in closets and bath with radiant heat and soaking tub. Three additional guest bedrooms is (one is ensuite and 2 share a bath with double entrances). There is an easy location to add an addition bath if required. A bonus room functions perfectly as a 5th bedroom or home office. Finished lower level includes a full bath, kitchenette, play/game room, gym and workshop. The side entrance via the three-bay, heated garage makes for easy living with spacious mudroom and laundry rooms with pet washing station. The one-bedroom guest house (c 2016) has a private driveway lead and features a stone fireplace, screened porch, single-bay garage.. It is currently used as an Air B&B, inquire about income potential. The property includes an owned solar system which achieves extremely low electricity bills for the estate. Some light fixtures are excluded.

96 Kinney Hill Rd, Washington
89 Under Mountain Rd, Canaan
$2,425,000
3 Beds ⋅ 3 Baths ⋅ 24046258 MLS
This stunning, Architecturally Designed Modern home was newly constructed in 2022 boasts being an energy-efficient passive house with an Energy Recovery System. No detail has been overlooked! Every decision was made with great thought and with the highest quality craftsmanship. This home is located on 58+ acres, with its own private hiking trails, a brook at the edge of the property, a mountain view, tiered lawns, and 200 ft of new stone walls. The home itself features 3 bedrooms, 3 bathrooms, and is chic and modern throughout. The Kitchen has all Thermador appliances, including a 99-bottle wine fridge and a built-in coffee maker. The dining room and living room have accordion doors opening onto the terrace, allowing for seamless indoor/outdoor living. Also on the first floor is a private office, laundry room, and a large bedroom with lots of storage and a full bath. On the second floor, you'll find a luxurious primary suite, a third bedroom ensuite, and a sitting room with a built-in library at the second-floor landing. If that's not enough, there's also a Post & Beam barn built in 2018, with 3 garage bays and 1 entry bay. There is a full bath on the first floor, the entire barn is fully insulated with the heat on the first floor, and finished space on the second floor. Plus, there's loads of room for storage, a studio, or a home office. It's close to private schools and all the amenities that the Litchfield Hills & the Berkshires have to offer.

89 Under Mountain Rd, Canaan
100 N Main St, Kent
$2,400,000
4 Beds ⋅ 6 Baths ⋅ 24177199 MLS
Set in the heart of historic Kent village, this exceptional circa-1800 New England Greek Revival Farmhouse marries small-town walkability with eleven-plus acres of true country privacy. This property underwent a meticulous, top-to-bottom restoration from 2016 through 2018, preserving the home's original character while quietly engineering it for modern life - new wall insulation throughout, expanded electrical service with overhead fans and period-correct lighting, refinished antique floors in every room, and five zones of climate control with hydro-air heat. The main level opens to a warm, paneled living room with a fireplace-anchored dining nook - both detailed with custom paneling added during the renovation. A formal dining room and a library with built-in shelves and a limestone fireplace flank the central hall. The adjoining game room - opened up when interior walls and doorways were reconfigured - leads through French doors onto an expansive covered front porch, completely rebuilt with a new copper roof, classical columns, and a stone floor base. A chef's kitchen sits at the heart of the home: a 60-inch Wolf propane range, warming drawers, Viking ice maker, a Shaw farmhouse main sink and prep sink, ROHL faucets, and Rejuvenation hardware are set against Cambria quartz countertops, a ship-lap backsplash, and a custom island with built-in microwave and cabinetry. Step from the kitchen onto the covered stone porch and into the courtyard - designed for al fresco dining

100 N Main St, Kent
148 Warren Hill Rd, Cornwall
$2,395,000
6 Beds ⋅ 6 Baths ⋅ 24179880 MLS
Privately set on 36 acres in Cornwall, Connecticut, this restored 1926 European Style estate commands expansive western views across the Housatonic Valley and offers a rare combination of architectural significance, privacy, and natural beauty. Constructed of handmade Belgian brick, the residence encompasses 6,061 square feet with 6 bedrooms and 6 baths. Original casement windows, thick plaster walls, soaring ceilings, and timeless architectural details reflect the exceptional quality and craftsmanship of a bygone era. Thoughtfully restored and updated, the home blends historic character with modern comfort. Multiple stone and brick terraces create seamless indoor-outdoor living spaces designed to take full advantage of the spectacular setting, abundant natural light, and ever-changing views. A heated gunite pool is beautifully integrated into the landscape, providing a private retreat surrounded by sweeping vistas and mature plantings. The grounds feature renowned Michael Trapp-designed gardens, open meadows, mature woodland, and walking trails. Approached by a gated drive, the estate offers remarkable seclusion while remaining convenient to the many cultural and recreational amenities of Litchfield County. A distinguished country estate where exceptional architecture, curated gardens, breathtaking views, and significant acreage come together in one of Connecticut's most sought-after settings.

148 Warren Hill Rd, Cornwall
12 Popple Swamp Rd, Cornwall
$2,377,000
6 Beds ⋅ 3 Baths ⋅ 24105244 MLS
A rare and storied offering, the Colonel Dwight Wellington Pierce Farmstead is a distinguished circa 1830 Greek Revival residence listed on the State Registry of Historic Places. Perched on a rise with views of mountains, conserved land, and state forest, it blends heritage, natural beauty, and modern comfort. Spanning over 4,300 square feet, the main house features original moldings, wide-plank floors, and five working fireplaces. There are six bedrooms-one on the main floor with a full bath, and five upstairs. The primary suite includes a fireplace, radiant-heated limestone bath, and a large walk-in closet. The kitchen boasts exposed beams, custom cabinetry, soapstone countertops, and premium appliances, opening to a sunroom and stone patio. Additional spaces include a formal dining room, living room, library, pantry, and mudroom with brick floors. Upstairs are four guest bedrooms, a Jack-and-Jill bath, and a charming laundry room. Historic character is enhanced by modern systems, including fiber-optic cable and an alarm system. Three historic outbuildings accompany the home: a 70x30 dairy barn, a heated 60x24 studio barn with a concrete basement, and a carriage barn with a two-car garage, three horse stalls, and a loft. The landscaped grounds feature award-winning gardens, mature fruit trees, stone walls, a pond, and full deer fencing. A stone patio offers serene views and a strong connection to nature.

12 Popple Swamp Rd, Cornwall
36 Fenn Hill Rd, Washington
$2,350,000
24171712 MLS
Sunsets, Silence, and 20-Mile Views over Steep Rock Preserve One of the rarest offerings in Washington: 80+ acres of open meadow, apple orchard, and wildflower fields perched above Steep Rock Preserve, with uninterrupted -views to the south and west. Set within one of the town's most coveted estate areas, the land moves from level pasture to gentle slope Several approved building sites accommodate everything from a singular country house to a full compound. The setting is defined by what isn't there: no traffic, no neighbors in sight, no light pollution - just long views, birdsong, and the sound of silence. Properties of this scale, character, and location rarely come to market. A foundational opportunity for a legacy estate minutes from the village of Washington Depot, the Mayflower Inn, and the cultural and equestrian life of Litchfield County.

36 Fenn Hill Rd, Washington
892 Candlewood Lake Rd S, New Milford
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 24155035 MLS
Welcome to this gorgeous Chimney Point Cove waterfront in the sought-after Candlewood Lake Club. Only 10 houses on the lake can claim this coveted location! This spacious 4,000+ sq ft home features a grand living room with a stone fireplace and a wall of windows framing spectacular, expansive northern mountainous views. Ideal for multi-level living, the first floor boasts a primary suite with stunning lake views, a second bedroom, and two full baths. The main level also features a gourmet kitchen, cozy den w/ fireplace, formal dining room with a bar-perfect for entertaining. The bright expansive finished lower level offers a massive great room with a fireplace and 2 private en suite bedrooms plus private walk out access to waterfront. Set on a unique, level half-acre lot with a circular driveway and detached 2-car garage. Enjoy elite club amenities: golf, tennis, pickleball, marina, and beach. A lake lover's dream-all just 90 minutes from NYC. Membership to CLC is optional (note: one time $15,000 initiation fee with Annual Club Dues $5,200 + CT State Tax Mandatory Roads ($475) and water fees ($600) are mandatory for all owners.

892 Candlewood Lake Rd S, New Milford
77 Tophet Rd, Roxbury
$2,300,000
4 Beds ⋅ 5 Baths ⋅ 24167123 MLS
Roxbury Shingle-Style Gem with Sparkling Pool! This grand residence sits off one of Litchfield County's most treasured and bucolic roads amidst boldfaced names - past and present - and backing up to a 60-acre parcel of Roxbury Land Trust. Prepare to be "wowed" by the sun-flooded double height living room, gorgeous eat-in-kitchen, formal dining room, four-season sunroom, wood-paneled library/den, and well-executed rec room. Four oversized bedrooms with ensuite baths, including primary suite options on both the main floor and upstairs. A large outdoor deck which spills onto a native stone terrace with grill and pizza oven; perfect for entertaining friends and family. Partially finished basement with gym and tons of storage. Pristine 20x40 gunite pool and spa added in 2022. Cagenio-wired smart home with mega-speed internet, Wifi covering the interior and exterior patio and pool areas, whole house generator. Many "hidden money" upgrades inside and out, including roof in 2021 (w/ 50-yr transferable warranty), five zone HVAC system with all units replaced 2021-2024, pool and spa in 2022, whole-house generator, mini-splits in the sunroom and gym area, and a comprehensive automation system. In the heart of Litchfield County, convenient to Lake Waramaug, fine dining, farmers markets, town tennis courts and thousands of acres of land trust to explore. 90 minutes to NYC but a world away.

77 Tophet Rd, Roxbury
152 East St, Sharon
$2,230,000
4 Beds ⋅ 6 Baths ⋅ 24125694 MLS
Set on 12.48 picturesque acres in Sharon, this exceptional retreat includes an additional buildable lot with majestic mountain views. A stunning great room anchors the home, showcasing gleaming oak floors, expansive windows, and a magnificent brick fireplace with custom wood mantel. The open-concept kitchen includes stainless steel appliances and a skylit breakfast nook, while the adjacent keeping room charms with a stone wood-burning fireplace and original wood siding. The main level primary suite impresses with its own wood-burning fireplace adorned with Delft tile, complemented by a luxurious full bath featuring a soaking tub, double vanity, and separate shower. Above, a curved staircase leads to an open landing with built-in bookshelves, connecting to two bedrooms - one with an en-suite half bath - and a full bathroom. A bonus bedroom above the garage includes a full bath, private balcony, and direct staircase access from the keeping room. The outdoor living space centers around a refreshing gunite pool and extensive stone terrace, perfectly positioned to capture breathtaking mountain vistas. Modern conveniences include a two-bay garage, providing both comfort and security in this Litchfield County retreat. This Northwest Connecticut retreat combines countryside tranquility with sophisticated amenities, offering multiple possibilities with its additional buildable lot.

152 East St, Sharon
63 W Mountain Rd, Washington
$2,195,000
4 Beds ⋅ 5 Baths ⋅ 24156353 MLS
Private oasis in prime Washington location on dead end dirt road. Short walk to Johnson Farm Preserve - one of Steep Rock Land Trusts hidden gems. Long driveway leads to reimagined 1950's home on 13+ acres with views towards Nettleton Hollow, pool and brook. Vaulted public rooms surround fireplace with oversized plate windows to take in light and view. 3 bedrooms and 3.5 baths in main section of house including oversized primary suite. 4th ensuite bedroom has heated flooring and is full walk out on lower level providing separation for guests. 40' gunite pool with auto cover, back yard area fenced for pets. Multiple entertainment spaces off south side of house. Many mechanical upgrades, ample parking and automatic generator complete the package. Special opportunity to be in nature yet less than 5 minutes from Mayflower Inn & Spa. Fewer than 15 minutes to New Preston, Washington Depot or Woodbury for shopping, restaurants and services.

63 W Mountain Rd, Washington
44 South St, Litchfield
$2,188,000
5 Beds ⋅ 7 Baths ⋅ 24150605 MLS
In the heart of Litchfield's coveted Historic District, along one of the town's most admired streets, stands the circa-1855 Woodruff House, an iconic Italianate Victorian Villa and enduring centerpiece of the neighborhood. Built for prominent Litchfield resident George Morris Woodruff, this beloved home blends architectural pedigree with modern livability. Signature elements include a shallow hipped roofline, distinctive columned verandah, double-tiered gallery, and dramatic two-story octagonal bays, a rare and remarkably preserved example of the period. Inside, grand yet inviting spaces unfold: formal entry hall, multiple living rooms for gathering and quiet retreat, dining room, den, office, and a spacious kitchen opening to a comfortable family room. The home offers five bedrooms including two primary suites, along with four full and three half baths, allowing guests and owners alike to live graciously. French doors lead to a sunroom and deck overlooking mature, landscaped grounds designed for entertaining with two patios, an updated heated pool, and the kind of setting that makes weekends linger longer. Modern comforts integrate seamlessly: elevator to primary bedroom, generator, four fireplaces and laundry room. A heated two-story barn provides flexible space for studio, workshop, or collector storage with room for two vehicles. Moments to the Litchfield Green. A rare opportunity to own not simply a home, but a recognized piece of Litchfield's architectural legacy.

44 South St, Litchfield
9 Oak Point Clb, New Milford
$2,111,000
4 Beds ⋅ 3 Baths ⋅ 24163703 MLS
AMAZING PRICE REDUCTION of 200K Rare, Level 4 BR, 4 Bath Contemporary Waterfront on Candlewood Lake offering over 3951 SF with amazing southerly views. Two story arched windows bring the outdoors in and offer incredible, wide lake views and level lawn to lakefront beach. The fabulous open plan focuses on a huge great room, with an interior balcony leading to three second floor bedrooms, office and 2 additional full baths. Coal stove for supplemental heat, hardwood floors, and views in all directions. A formal dining room with slate floors and sliders to the patio is adjacent to the updated Kingswood kitchen hosting white shaker cabinets, new appliances, granite counters and matching granite tiled floors. The main level showcases a stunning entry, double set of coat closets and a second full bath plus a huge laundry room/office and 2 car attached garage. Manicured yard, level lot, sand beach, private dock & stunning south facing views make this a unique take opportunity! Close to New Milford town center, shopping , dining , movie theater and easy access to I84. A private oasis in this small Candlewood Lake enclave! Bring your bathing suits, paddle boards , kayaks and just relax! A one of a kind opportunity! Priced to Sell!

9 Oak Point Clb, New Milford
15 Herrick Rd, Sharon
$2,100,000
3 Beds ⋅ 3 Baths ⋅ 24124697 MLS
Contemporary elegance on one of Sharon's most prestigious addresses. A classic pea stone driveway leads to this newly renovated and glamorous 3 BDR/3 Bath country home in a stunning natural setting with interiors designed by the NY-based firm Majordomo Lifestyle Architecture. Sleek sophistication abounds with gracious vaulted ceilings in the living room, anchored by a striking stone fireplace. The living room flows seamlessly into an expanded sunroom bathed in natural light - perfect for intimate dinners and grand entertaining with access to the patio. The updated eat-in kitchen serves as the heart of this modern masterpiece, with top of the line appliances and ample storage. Luxurious accommodations include an enlarged en-suite Primary BDR with fireplace on the main floor and access to the patio, and 2 spacious en suite bedrooms upstairs. Every space has been thoughtfully renovated to blend contemporary comfort with timeless charm. 2-car detached garage/barn offers extraordinary storage/work/studio spaces. Herrick Road places you at one of the finest locations in Sharon known for its exceptional estates and natural beauty. This home is a lifestyle statement in one of Litchfield County's most desirable communities. Enjoy this idyllic setting where cattails whisper in the breeze and privacy reigns supreme. Private schools nearby: (Hotchkiss, Kent School, Salisbury School, Millbrook School), skiing at Mohawk and Catamount, Sharon Playhouse, and Audubon. 2 hours to NYC.

15 Herrick Rd, Sharon
221 Fuller Mountain Rd, Kent
$2,075,000
4 Beds ⋅ 5 Baths ⋅ 24126900 MLS
This extraordinary residence is a masterful blend of timeless architectural inspiration and modern luxury, offering a rare opportunity to own a home that is both a work of art and a private retreat. Designed in homage to the style of Frank Lloyd Wright, it features hipped roofs with wide eaves, long horizontal lines, and a seamless integration with the natural landscape. The house is set well back from the road and approached by a meandering driveway that crosses Jack Brook, enhancing both privacy and the sense of arrival. Situated on more than 22 wooded acres, the home provides unmatched seclusion, with nearly every room opening to outdoor living spaces, including covered porches, open terraces, and a serene Zen-inspired courtyard. A dramatic two-sided stone fireplace anchors the main living area, complemented by soaring ceilings and French doors throughout. The chef's kitchen is equipped with a Wolf stove, Sub-Zero refrigerator, center island, and breakfast bar, and opens to a covered porch with seasonal views. The first-floor primary suite, entered through a den with custom built-ins, offers a fireplace, two walk-in closets, a spa-like bath with infinity tub and shower, as well as a sunroom and covered porch overlooking the gardens. Additional spaces include a bedroom/office on the main level and two bedrooms with a sitting area upstairs.

221 Fuller Mountain Rd, Kent
8 Sunrise Ln, Bridgewater
$2,058,000
4 Beds ⋅ 4 Baths ⋅ 24168617 MLS
Arriving at 8 Sunrise Lane is nothing short of enchanting. A long, private drive winds through sweeping open lawns, under mature trees, past the chicken coop & flourishing orchards before it reveals the home-perfectly sited to capture picturesque, elevated views. The main level is designed for effortless living and entertaining, anchored by a beautifully renovated kitchen that flows seamlessly into the living area. From here, step out to a screened porch, an open-air porch & an expansive wraparound covered porch--each offering a unique vantage point to enjoy the spectacular landscape. A formal dining room and a bedroom with full bath complete this level. Down a short hallway, a separate wing provides guest accommodations with a 2-bedrooms & its own living area--ideal for extended family, guests, or an in-law setup. Upstairs, the current primary suite offers a private retreat with French doors opening to a balcony, along with a lofted office & sitting area overlooking the space below. Outdoor living is equally impressive. Bluestone terraces framed by classic stone walls & manicured boxwoods lead to a fully equipped outdoor kitchen--perfect for poolside gatherings. The gunite, salt water, pool, complete with automatic cover & spa, is surrounded by lush gardens bursting with peonies & hydrangeas. A wisteria-draped pergola provides a serene spot to relax & take in the scene.

8 Sunrise Ln, Bridgewater
382 Weekeepeemee Rd, Woodbury
$2,050,000
4 Beds ⋅ 4 Baths ⋅ 24159893 MLS
The Jesse Peck Lambert Homestead, built in 1805 & thoughtfully restored, provides a seamless blend of historic charm & modern comfort. Set on 6.42 acres in Northern Woodbury on the Washington border just 2 hours from NYC, this 4-bedroom/3.5-bath home provides a serene escape with timeless appeal. The newly designed kitchen is a chef's dream, featuring custom rift-sawn white oak cabinets, oiled soapstone counters, a Sub-Zero fridge, Wolf 6-burner range & burnished nickel Waterworks fixtures. Every detail has been carefully curated, from soft-close drawers to premium finishes. Historic touches abound, including heartwood floors, an open hearth fireplace with a beehive oven & original millwork with hand-forged cast iron hardware. The primary bath is a spa-like retreat with a cast iron soaking tub, stone surround & custom vanity, while modern updates enhance the other baths with style & practicality. All new custom Anderson 400 Series windows flood every room with light while preserving the home's historic proportions. The large flat property invites outdoor enjoyment with a tranquil pond, mature 200-year-old trees & fenced-in vegetable garden. A restored English barn with a loft, 11-foot custom insulated steel barn doors, insulated and propane-heated garage, floor drains & updated electrical systems provide space for projects, storage, or entertaining.

382 Weekeepeemee Rd, Woodbury
126 Sherry Ln, New Milford
$2,000,000
3 Beds ⋅ 5 Baths ⋅ 24163112 MLS
Spectacular Direct Waterfront on Candlewood Lake - located in southern New Milford within highly desirable Candlewood Point private community. Prized western exposure with commanding views. Incredible grounds with expansive level lawns, beautiful stone work, & thoughtful outdoor entertaining areas. Gut renovated and expanded in 2009, this home blends timeless character with modern amenities. Inside, vaulted ceilings with exposed beams, gleaming hardwood floors, and a stunning fieldstone fireplace anchor the open living & dining areas, all flowing seamlessly to a large lakeside deck. Central, well-appointed kitchen with granite countertops and stainless steel appliances. Expansive primary bedroom with en-suite bathroom, walk in closet, & sweeping lake views. A separate wing offers 2 large guest bedrooms, full hall bath & laundry room. There is also an office, study, and an additional full bath on the main level. Upstairs, an impressive bonus space with wet bar, full bath, & private balcony provides an elevated vantage point over the lake. The finished lower level adds additional living space, another office, a second laundry area with dog wash, plus a direct walkout to the lake. The home also features an attached heated/cooled 2-car garage with powder room and ample driveway parking. Outside, there is an expansive stone patio, covered porch, and 2 storage sheds with electricity. The oversized dock features room for lakeside dining, lounging & multiple boats.

126 Sherry Ln, New Milford
50 Main St, Salisbury
$2,000,000
4 Beds ⋅ 4 Baths ⋅ 24126748 MLS
This 1807 New England home stands prominently in Salisbury's Historic District, gracing 1.4 pristine acres. The main residence exemplifies timeless architecture with five working fireplaces and seamless updates that honor its historic integrity, including a newly renovated kitchen with custom cabinetry and sleek countertops. A comprehensive heating and cooling system ensures year-round comfort, enhanced by radiant floor heating in the primary bathroom. The thoughtfully designed main house flows beautifully to the remarkable 1810 carriage house, now transformed into additional living space with two bedrooms. The property's crown jewel is the heated gunite pool with an automatic cover, creating an elegant outdoor entertainment space. Both structures showcase meticulous craftsmanship with cedar shake roofs, copper gutters, and refined details like the radiant-heated exterior staircase for snow and ice management. The paved driveway features distinctive cobblestone edging, elevating the property's classic appeal. Set in the heart of Litchfield County, this historic retreat seamlessly combines village convenience with private sanctuary. The grounds include a serene private garden and direct access to the scenic rail trail, offering the perfect balance of accessibility and seclusion in Northwest Connecticut's most sought-after town.

50 Main St, Salisbury

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