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98 Island Trl, Morris
$1,985,000
4 Beds ⋅ 5 Baths ⋅ 24165057 MLS
Set on one of Deer Island's most gracious waterfront parcels, this 1920s lake house offers approximately 3,500 square feet of living space across five bedrooms and approximately 142 feet of lake frontage. The property features mature landscaping with specimen trees, a boathouse with drive-in docking and changing rooms, a private boat launch, stone lakefront walls and a built-in outdoor grill area. Unlike many homes of its era, the interior layout is open and bright, with hardwood floors and generously sized rooms throughout. A window-lined living room with a wood-burning river stone fireplace anchors the main level, offering expansive lake views. The adjacent kitchen includes a butler's pantry and ample storage, flowing into a formal dining room framed by two walls of windows, and French doors that open to a sun-filled family room with stone accent wall. Upstairs, the primary suite features a jacuzzi tub, double vanity, and stall shower. Four additional bedrooms share a full bath and powder room. The lower level, with full-height ceilings, includes a large, windowed kitchen and a half bath, offering potential for expanded living or entertaining space. Additional land available. An adjacent separate, buildable lot with garage at 90 Island Trail offering space for future development or compound living. Sold with additional lot.

98 Island Trl, Morris

32 Grassy Hill Rd, Roxbury
$1,966,500
4 Beds ⋅ 5 Baths ⋅ 24085777 MLS
Roxbury dream home with forever views. Tucked away down a gracious drive off a bucolic town road this quintessential Georgian welcomes you home and envelopes you in calm and comfort. Arrival at the motor court provides the first glimpse of a western view that stretches from Roxbury as far as the eye can see, giving an immediate sense of place. The home, unabashedly radiant in its sunny yellow color, was purchased by the current owner in 2021 and underwent an exquisite glow-up by a noted local designer who transformed the residence into something formal, yet intimate; a place that feels so right with rooms that serve purpose. The masterfully appointed chef's kitchen will delight with abundant prep space, oversized range, and a refrigeration wall with dedicated cooling, freezer and wine storage. A sun-filled gathering space is adjacent as well as an informal dining area. A butler's pantry connects the kitchen and the formal dining room. The formal LR is across the foyer, a serene space with one of the home's 3 fireplaces. A den and a media lounge complete the main floor. Upstairs, the primary suite has been reimagined into a luxury space with dressing room and a spa bath. 2 guest BRs and a full bath complete this level. Above the 2 car garage is a guest apartment with living area/gym, BR and BA. Immaculate grounds with mature gardens and multiple outdoor dining spaces. Ready for new memories, this is a gem of a home within a dream of a town.

32 Grassy Hill Rd, Roxbury

143 Tophet Rd, Roxbury
$1,925,000
4 Beds ⋅ 6 Baths ⋅ 24093575 MLS
Located along one of Roxbury's most coveted stretches, this property is nestled among an 800+ acre greenbelt of farmland and conserved land with plentiful hiking trails. The open floor plan is designed with 9 foot+ ceilings, detailed millwork and oversized windows which infuse the interiors with natural light. The main level features a show stopping kitchen open to the dinning and media rooms. There is also a formal living room with wrap around deck which takes in the views. Interiors are newly updated with designer wallpapers, custom window treatments, and luxury lighting. The second floor hosts 3 generously sized en-suite bedrooms which surround a central gathering space with built-in desks. The attic level is fully finished with a full bath for 4th bedroom, game room, gym, home office and/or studio. The salt water heated pool and spa take in the rolling ridge line views across a vast tract of protected land. Newly cleared lawns with fire pit. Excellent mechanical systems, including a 27K generator and Buderus furnace. Peaceful and private, yet just 10 minutes to Washington or Woodbury for farm stands, organic groceries, restaurants and boutiques. 1.5 hours from NYC and 30 minutes to the train station.

143 Tophet Rd, Roxbury

56 Sharon Rd, Salisbury
$1,860,000
5 Beds ⋅ 3 Baths ⋅ 24151728 MLS
This distinguished 1880s Victorian residence in the heart of Lakeville village offers a masterful blend of period craftsmanship and contemporary luxury on 2.5 private acres. Located moments from both the town green and Lakeville Lake, this meticulously restored 5-bedroom estate presents refined living in one of Litchfield County's most sought-after locations. The welcoming wrap-around covered porch leads to an elegant entry hall featuring a striking curved staircase. Grand proportions define the formal rooms, where original wood-burning fireplaces, soaring ceilings, and oversized windows create an atmosphere of timeless sophistication. The gourmet kitchen showcases top-tier stainless appliances, substantial island, and bespoke wood cabinetry, with a bright dining area flowing to the generous rear deck overlooking the grounds. The second floor houses a bright primary suite with ensuite bath, three additional bedrooms, a dedicated home office, and a luxurious bathroom featuring custom marble, Waterworks fixtures, and radiant heat flooring. A stylish laundry room and thoughtful storage complete this level. The third floor provides a secluded guest retreat with original wood floors, flexible studio space, and cedar-lined storage. The property's exceptional amenities include a versatile two-story barn with basement-ideal for studio, workshop, or recreational pursuits-plus a detached one-car garage. The Serene grounds frame this village estate, offering the rare

56 Sharon Rd, Salisbury

56 Richards Rd, Kent
$1,850,000
4 Beds ⋅ 4 Baths ⋅ 24185944 MLS
Escape the pace of everyday life and embrace the beauty of country living in this spacious contemporary home, perfectly situated abutting conserved land with exceptional recreational amenities. Offering 4 bedrooms and 3.5 baths, the home features an open-concept floor plan designed for both comfortable living and effortless entertaining. The sunken living room is anchored by an elegant gas fireplace and enhanced by soaring ceilings and hardwood floors, while a bright sitting room with walls of windows overlooks the spectacular grounds and fills the home with natural light. The second floor hosts a generous primary suite with a bath featuring double sinks, an oversized whirlpool tub, and separate shower. Two additional bedrooms share a hall bath. The walk-out lower level offers a fourth bedroom and full bath, a spacious media/game room, abundant storage, and potential for a bunk room or additional recreational space. Step outside to a stone terrace with a relaxing Jacuzzi, creating the perfect setting for unwinding after a day on the lake or skiing at nearby Mohawk Mountain. Outside, the expansive level lawn provides plenty of room for play, while the beautiful heated Gunite pool serves as the centerpiece for summer entertaining. There is also a shaded half size basketball court. The land has additional building lot in the total acreage.

56 Richards Rd, Kent

431 W Wakefield Blvd, Winchester
$1,850,000
9 Beds ⋅ 6 Baths ⋅ 24159989 MLS
Live the Highland Lake Dream - 431 W. Wakefield Blvd, Winchester, CT Summer is just around the corner - and in Winsted, resort living never ends. Recently named one of the most desirable towns to live in, with the breathtaking Highland Lake at its heart, Winchester offers the perfect blend of beauty and lifestyle. This waterfront estate at 431 W. Wakefield Blvd isn't just a home - it's your gateway to the ultimate lake life. Wake each morning to panoramic water views, and step outside to a world of four-season recreation. In summer, enjoy boating, jet skiing, swimming, and fishing right from your private dock, or simply relax by the shoreline. When winter arrives, the lake transforms into your own frozen wonderland for ice fishing, skating, and fireside gatherings. Inside, luxury awaits. The main home features gourmet finishes, a chef's kitchen, and custom craftsmanship throughout. A charming guest bungalow offers privacy for family, friends, or guests. Zoned for a bed and breakfast, and featuring an extra subdividable lot, the property offers immense potential - whether as a private retreat, an upscale B&B, or an investment in future development. Set on 425 feet of pristine water frontage, this estate captures the essence of Highland Lake living - natural beauty, year-round recreation, and endless opportunity.

431 W Wakefield Blvd, Winchester

30 Knibloe Hill Rd, Sharon
$1,850,000
3 Beds ⋅ 3 Baths ⋅ 24126355 MLS
Renovated Sharon Farmhouse with Brook Views | Knibloe Hill Road, CT - This newly renovated farmhouse graces one of Litchfield County's most coveted addresses, overlooking a peaceful babbling brook in Sharon, Connecticut. The thoughtfully reimagined residence combines classic charm with contemporary refinements throughout its light-filled spaces. A welcoming front porch leads to an elegant interior where 10-inch pine plank floors flow through the sun-drenched living room, highlighted by a vaulted ceiling and gas fireplace. The stunning kitchen presents state-of-the-art appliances, a custom oak island with quartz top, and Carrera marble-finished cabinetry. An adjoining dining room with vaulted ceiling and new skylight connects to both a mudroom and spacious sun porch warmed by a wood stove. French doors in the den access a side porch with enchanting property views. The main level primary suite provides a private sanctuary, complete with a luxurious spa-style bathroom featuring a soaking tub and marble-tiled shower. Two additional bedrooms share a well-appointed full bath on the upper level. Perfectly positioned in Northwest Connecticut's prestigious Sharon area, this property offers convenient access to Metro-North rail service while remaining close to the region's finest amenities including Lakeville, Salisbury, Hotchkiss School, Lime Rock's IMS, and the charming village of Millerton.

30 Knibloe Hill Rd, Sharon

102 North St, Litchfield
$1,825,000
3 Beds ⋅ 4 Baths ⋅ 24083295 MLS
Step into the pages of history with the beautifully revitalized Col. Charles Webb house, circa 1830, a centerpiece of Litchfield's storied past. This iconic residence has been thoughtfully updated, blending classic elegance with modern amenities. As you enter through the entryway, you are greeted by the warmth of wide board flooring and an inviting arched doorway. The journey continues to a convenient wet bar and into the sunlit formal living room, where a wood-burning fireplace, built-in cabinets and polished hardwood flooring create an atmosphere of timeless charm. The formal dining room, with another wood-burning fireplace, offers ample storage and two closets. The great room is a marvel of architectural design, featuring a soaring ceiling, elegant French doors and luminous Palladian windows that invite the outside in. Culinary enthusiasts will revel in the chef's kitchen, boasting a gas range, dual new dishwashers, a Subzero refrigerator, a breakfast bar and a cozy dining area. A versatile mud/playroom and a half bath complete the main level's offerings. Ascend to the upper level, where the primary bedroom suite has been freshly painted and adorned with new oak floors and custom molding, creating a serene escape. The en-suite primary bath has been transformed with a new custom shower and linen closet. Two additional guest bedrooms (one en-suite) have undergone complete renovations, featuring new oak flooring, fresh paint and remodeled

102 North St, Litchfield

18 Ranney Hill Rd, Roxbury
$1,795,000
4 Beds ⋅ 4 Baths ⋅ 24170163 MLS
Perfect Country Home! Located close to town on a quiet country road. Built is 2018, the new owners have done extensive Landscaping. A privacy fence was installed on the front of the property with evergreens planted on both sides of the fence . There is a small apple orchard planted on the property. Extensive stonework and plantings have been done around the house and an in ground pool with pebble tech finish was installed with fencing in the rear yard for the pool and pets. The house was originally built by a Master Craftsman with the finest materials.The gourmet kitchen is where everyone lives. There is a center island and field stone fireplace. Thermador appliances include a 6 burner cook top as well as wall oven, built in microwave, a warming drawer, dishwasher and refrigerator. The open floor plan allows you to set up the living room/dining room in a variety of ways. There is a lovely sunroom with a vaulted ceiling off the kitchen. There is a mudroom coming in from the garage with a half bath. The ceilings are 9' on the first floor. The upper level includes a lovely Primary Suite with walk in closets, a luxurious primary bath with 2 sinks, a walk in shower and a soaking tub. There are 3 additional bedrooms on the upper level with one en-suite and the other two sharing a hall bath. The house sits up high with mountain views. The land is gently sloping with a level area with plenty of room to play. Only 90 minutes to NYC!

18 Ranney Hill Rd, Roxbury

176 Apple Ln, Roxbury
$1,764,000
4 Beds ⋅ 5 Baths ⋅ 24176141 MLS
Your turnkey country escape is waiting in Roxbury - a modern shinglestyle home on 4+ manicured acres with a resortlevel pool, just far enough from the city to exhale, yet close enough to make spontaneous weekend getaways a reality. From the moment you arrive, this summer ready property feels like a private club: stone walls, curated landscaping, quiet woods, and outdoor spaces designed for long summer days and late night gatherings. The gunite pool is the centerpiece - sparkling, secluded, and ready the moment you are. Inside, sunlight pours through picture windows into an open layout built for effortless entertaining. Custom oak details, a dramatic fieldstone fireplace, and a chef's kitchen with high-end appliances and stone counters set the stage for everything from cozy winter weekends to lively holiday hosting. With 4 ensuite bedrooms, the home adapts beautifully to guests and long family weekends. The first floor ensuite offers effortless hospitality, while the second floor luxury primary suite- complete with 11 foot ceilings and a marble spa bath - provides a calm, spa-level retreat. A steel-and-glass office alcove and a bonus room above the garage with interior access, offer the perfect flex space for a studio, gym, or potential guest suite. The finished lower level and walkout access adds even more room to unwind. Fully renovated since 2021 including new HVAC, generator, and more - means no projects, no delays to start enjoying the Litchfield Lifestyle.

176 Apple Ln, Roxbury

509 Main St N, Woodbury
$1,752,500
6 Beds ⋅ 8 Baths ⋅ 24121221 MLS
Tucked away in absolute privacy, yet centrally located, this exceptional estate offers 6,300+ square feet of refined living space that seamlessly blends country sophistication modern luxuries. Crafted w/warmth & character throughout, the home boasts wide board hardwood floors, coffered ceilings, French doors, exposed beams, & built-ins. With 13 thoughtfully designed rooms, the home features 6 generous bedrooms, 6 full bathrooms, & two 1/2 baths. Each bath w/radiant heated floors for comfort. Primary suite has 2 walk-in closets, & office space. At the heart of the home is a stunning, brand-new custom kitchen featuring handcrafted cabinetry, an 8-burner gas range, built-in coffee bar, & an elegant butler's pantry. The floor plan offers multiple spaces to live and unwind: a formal living room w/fireplace, a media/game room on the lower level, a dedicated home gym, & two convenient laundry areas. Additional fireplaces can be found in the eat in kitchen, primary suite, & lower level. Heated 2-car garage w/EV charging station & unfinished space above for future customization. The two-story barn offers storage & creative use. The beautifully manicured grounds are a celebration of nature: stone walls & lush gardens frame multiple outdoor living spaces. There are stone patios/walkways, covered porches, & the built-in grill is perfect for entertaining. Tap maple trees for syrup in winter, tend bees & gardens in summer, or press cider in the fall... this home is a year round experience!

509 Main St N, Woodbury

8 Bobcat Ln, Warren
$1,727,000
4 Beds ⋅ 5 Baths ⋅ 24133854 MLS
Perfectly positioned to capture breathtaking sunset views, this beautifully updated four-bedroom residence blends comfort, sophistication, and functionality. The home's chef-inspired kitchen features dual workstations, radiant heated floors and opens seamlessly to a cozy sitting area that extends outdoors to the pool and entertaining space. Here, you'll find a charming pool house, built-in grill, and bluestone patio-ideal for gatherings or quiet evenings under the stars. Inside, the great room impresses with walls of glass that flood the space with natural light and a fireplace that anchors the room with warmth and style. The main-floor primary suite offers a spa-like retreat with a soaking tub, steam shower, heated radiant floors, and dual walk-in closets. The main level also includes a formal dining room, a private office, and the convenience of a residential elevator providing easy access to all levels. Upstairs, there is an ensuite bedroom and two additional bedrooms that share a well-appointed bath. The finished lower level expands the living space with a full bath, laundry area, and flexible rooms perfect for a media room, gym, or recreation area. Set on a private 10+ acres featuring a picturesque pond and a detached barn ideal for a car enthusiast or hobbyist, this home offers the perfect balance of elegance, privacy, and modern living.

8 Bobcat Ln, Warren

171 E Shore Rd, Morris
$1,721,000
3 Beds ⋅ 4 Baths ⋅ 24129415 MLS
Lakefront estate set on 1.33 acres of rolling waterfront on Bantam Lake. 3 buildings total including main house, detached 2 car garage, stand alone office/den. Waterfront with stunning views, dock and lift. 3258sqft house with main level master suite addition including bedroom, full bath, kitchenette, and 2 story family room with fireplace and views! Eat-in-kitchen with stainless appliances, vaulted ceiling, beams, and skylights. Cozy living room with fieldstone fireplace and slider to deck. Additional main level bedroom suite with attached bath. Upstairs 3 additional rooms plus full bath. Finished basement with walk-out. Main level trex deck with outdoor grill and sink. Additional outbuilding finished single room. Detached 2 car garage. Central air, sec sys, irrigation, landscape uplighting, plenty of parking along circular drive with 2 entrances to the road. Gorgeous meandering lot with lakefront and views. Bucolic setting with professional landscaping and plantings throughout the lot and tastefully incorporated into the topography with stone walls, patios, and walkways. Thoughtfully planted trees & shrubbery protect privacy while creating a home away from home atmosphere. Many possibilities for this property. Oil tanks in basement. Propane tank buried. Town card has total of 3 bedrooms and 3 bathrooms. Property has many extra rooms and 4 bathrooms. Attached floor plans is incorrectly labeled. Please ignore room names. Also listed with neighboring property as MLS24122976.

171 E Shore Rd, Morris

68 Anderson Rd, Kent
$1,700,000
3 Beds ⋅ 3 Baths ⋅ 24178571 MLS
Tucked along the scenic beauty of Anderson Road-one of Kent's most coveted addresses - this enchanting country estate offers a true escape. A pea-stone driveway guides you past lush landscaping, field stone walkways, the charming 1835 main house, and on toward the stunning barns, revealing the property's timeless elegance, piece by piece. The main residence brims with original character - wide board chestnut floors, the original large hearth cooking fireplace, wood shingle roof, and cozy interiors that invite relaxation. The bright and cheerful eat-in kitchen is the heart of the home, ideal for casual mornings and late-night conversations. A great room with wood-burning fireplace, an intimate library with handcrafted bookshelves, and a dining room thoughtfully repurposed as a media room create multiple spaces to unwind and entertain. Just off the dining room, a lovely bluestone deck overlooks the apple orchard and offers a restful spot for a morning coffee or dining al fresco. There is a convenient and discreet powder room located off the foyer. Upstairs, there is a primary bedroom suite with bath, and two additional bedrooms sharing a bath. One of the guest rooms has a unique ante-room-perfect for a walk-in closet, dressing area, or a private reading nook. Wander past the main home to discover two classic barn structures: one impeccably transformed into a pristine carriage barn w/ handcrafted iron chandeliers to light the interior.

68 Anderson Rd, Kent

93 Northfield Rd, Litchfield
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 24103342 MLS
Step into a harmonious blend of history and modern luxury at Bittersweet Ranch, a meticulously updated home home dating back to 1767, set upon 39 magnificent acres backed by state land for privacy and no neighbor obstructions. This exquisite property features diverse topography with meadows, trails and forests, ideal for horseback riding, hunting and birdwatching. The chef's delight kitchen boasts a gas range, electric oven, sleek stainless steel appliances, a farmhouse sink and granite countertops. The large sunroom is a haven for relaxation with brick flooring and sliding glass doors, while original wide board oak floors add timeless elegance. Entertain in the formal dining room with a rolling barn door and propane fireplace. The den invites gatherings with its custom built bar and woodstove. A well appointed office space is complete with built-in bookcases. Guests will revel in the ensuite bedroom with propane fireplace. The primary suite offers a walk-in closet, sliding door, ceiling fan and custom built bed. A media room and laundry room add convenience. The lower level features a mudroom, playroom, half bath, laundry area and a three-car garage. Outside, the expansive patio is perfect for entertaining amidst meadows. The property includes a 72 x 28 greenhouse with potential for a nursery and is adorned with berry patches and classic stonewalls.

93 Northfield Rd, Litchfield

225 Old Sherman Hill Rd, Woodbury
$1,700,000
4 Beds ⋅ 5 Baths ⋅ 24072926 MLS
Discover refined country living in this remarkable Woodbury estate set on 33.98 private acres in sought-after Litchfield County. The 4,517 sq ft residence features 4 bedrooms, 4.1 baths, and bright, open interiors designed to capture serene views of distant hills. A spacious deck overlooks the sparkling saltwater gunite pool, creating an ideal setting for relaxation or entertaining. Equestrians will appreciate the immaculate 8-stall stable, 14 lush paddocks, and generous riding spaces surrounded by pastoral beauty. Completing the property is a 4-car garage and the peace and privacy that define Woodbury's countryside. This rare offering combines elegance, comfort, and the timeless appeal of New England living.

225 Old Sherman Hill Rd, Woodbury

455 Milton Rd, Goshen
$1,650,000
3 Beds ⋅ 4 Baths ⋅ 24097099 MLS
Nestled along the coveted west shore of Woodridge Lake, 455 Milton Road reveals a rare sanctuary of lakefront elegance. Set on 2.57 acres with 136 feet of pristine shoreline, this beautifully sited home captures sweeping views of a secluded island, the sun-dappled water, and the distant silhouette of the clubhouse and recreation center. Mature trees filter golden light across the open terrain, creating an atmosphere both serene and inviting. Beyond the doorstep lies the Woodridge Lake lifestyle: a private marina, heated pool, sandy beaches, tennis, pickleball, fitness center, and miles of picturesque trails. All just minutes from Litchfield's historic village, Mohawk Mountain for skiing, top-tier golf, and the cultural richness of the Berkshires. Priced at $1,650,000-recently adjusted from $1,750,000-this is more than a property: it's an invitation to craft your own legacy in one of New England's most revered lake communities.

455 Milton Rd, Goshen

397 Christian St, Bridgewater
$1,615,000
4 Beds ⋅ 4 Baths ⋅ 24172387 MLS
As quintessential Bridgewater as it gets, this exceptional residence - originally the Mallet District Schoolhouse, circa 1829 - was masterfully restored & expanded in 2006 - blending historic charm with modern amenities. Set on a coveted, level acre lot, framed by classic New England stone walls, the property offers gorgeous rolling lawns in a park-like setting. Inside, exquisite period details shine with wide-plank oak floors, stunning custom millwork, and five wood-burning fireplaces - complemented by phenomenal room scale and abundant natural light. The chef's kitchen is beautifully appointed with an 11-foot island, farmhouse sink, & gorgeous high-end appliances. The sunlit eat-in area opens to a serene bluestone patio. The open layout seamlessly flows to a paneled family room with fieldstone fireplace & powder room, as well as elegant formal living and dining rooms - both with striking brick fireplaces. The original school house wing features a private bedroom suite with sitting area & marble bath. Upstairs, the primary suite offers a walk-in closet, marble bath with clawfoot tub, and fireplace. Down the hall, there are 2 additional guest bedrooms, marble hall bath, and a laundry area. There is also a large walk-up attic and walkout lower level that both offer expansion potential. Outside, there is a charming two car detached garage. Situated in one of Bridgewater's most sought-after settings, this property offers the opportunity to embrace a refined country lifestyle.

397 Christian St, Bridgewater

17 W Morris Rd, Morris
$1,605,000
3 Beds ⋅ 3 Baths ⋅ 24086608 MLS
Nestled on 4.32 picturesque acres in sought-after location bordering Washington and Bantam, this charming remodeled country cape with gunite pool, 4 season pool house, outdoor shower and barn/garage offers a blend of classic New England style and modern amenities. The property is enveloped by mature plantings, established gardens, with handsome stonewalls, waterfront on nearby pond, creating a serene and private setting from the welcoming front entrance to the two inviting rear terraces. An open floor plan seamlessly connects the spacious living room, featuring built-in bookshelves, stone fireplace, and hardwood floors, with the well-appointed kitchen and formal dining room. The dining area boasts three walls of windows that frame a lovely western view of the rear grounds and provides access to both an upper-level deck and a stone terrace complete with a built-in grill, ideal for outdoor entertaining. The large kitchen is equipped with center island, ample counter space, Thermador gas range, Bosch refrigerator and dishwasher, and a charming banquette for casual dining. Two comfortable bedrooms and a full bath complete the main level, with French doors leading from one bedroom to the deck. Upstairs, discover a versatile den or office space and the master bedroom suite, which includes a full bath, walk-in closet, vaulted ceiling with beams, and built-in storage. The fully carpeted walk-out lower level offers a spacious family room, a convenient half bath, and laundry room

17 W Morris Rd, Morris

16 Westmount Rd, Salisbury
$1,600,000
5 Beds ⋅ 4 Baths ⋅ 24164558 MLS
Set on 10 private acres just five minutes from downtown Salisbury, this spacious 4-bedroom, 3 full, 2 half bath home offers over 5,000 square feet of elegant living space. Perfect for entertaining, it features a formal living room with fireplace, an oversized kitchen with walk-in pantry, and a flexible layout including a primary suite with en-suite bath and walk-in closet. A highlight is the year-round indoor pool with jetted swim current-ideal for exercise or relaxation. The detached 3-car garage offers oversized bays and a finished upper level for a home office, studio, or guest suite. Enjoy landscaped gardens, open lawn, and mature trees offering peace and privacy. Conveniently located near Sharon, Millerton, Great Barrington, and the Wassaic Train Station with service to NYC, this turnkey Litchfield County retreat blends modern comfort with country charm.

16 Westmount Rd, Salisbury

31 Hickory Ln, Roxbury
$1,600,000
4 Beds ⋅ 5 Baths ⋅ 24133274 MLS
This special home is located in one of Roxbury's most desirable neighborhoods on a quiet dead end road. A long, winding & very private driveway leads up to the commanding double-story porticoed entrance. The traditional colonial layout includes a central chef's kitchen which rests between the formal living, media & dining rooms. The main floor is completed by an office, 2 half baths, and a 2-room bedroom suite - perfect for guests, in-laws, or live-in help. This wing could easily be converted to a main floor primary if desired. Upstairs hosts the current primary bedroom w/ frpl & updated bath, as well as 2 addl bedrooms w/ a shared hallway bath. The updated, eat-in kitchen walks out to an airy screened porch w/ ample space to accommodate both lounging & dining. It is lightly shaded by mature trees and overlooks fieldstone terraces, established gardens & fruit trees. This property offers a uniquely flat and expansive lawn in a truly 'park-like' setting. The previous owner was a master gardener who meticulously cultivated specimen Rhododendrons throughout the lightly wooded surrounds. The mature plantings combine w/ native Mountain Laurel to create a spectacular display in early Summer. The exterior is completed by a 22 x 45 salt water, Gunite pool w/ integrated 6 x 8 Jacuzzi. It is 10' deep & boasts a diving board, retractable cover, & automated chemistry system allowing for hassle free ownership.

31 Hickory Ln, Roxbury

21 Hemlock Rd, Roxbury
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 24194995 MLS
This 4 bedroom main house with 2 bedroom guest house provides a peaceful retreat just minutes from town and 1.5 hours from NYC. The cape style main house is privately sited to capture breathtaking western views and sunsets. It features a light-filled open floor plan designed for effortless everyday living and entertaining. French doors open to an expansive deck where sweeping western vistas create the perfect backdrop for relaxing or hosting while overlooking the frolicking horses at the neighboring property. At the heart of the home is a stylish kitchen with a generous center island, ideal for both casual gatherings and inspired culinary creations. The great room incorporates a dining area and seating area with fireplace. The main floor is completed by the primary bedroom with ensuite bath and the 2nd bedroom which is conveniently located adjacent to the primary and could be used as additional closet or office space. Upstairs, 2 bedrooms share a hall bath. An additional 800+/- square feet of walk-out lower-level space has high ceilings and is plumbed for a full bath. It offers potential to create a play room, home gym, media room, or in law suite. The under-house two-car garage offers space for vehicles and/or storage. Complementing the main residence is a 1,400-square-foot ranch style guest house featuring two bedrooms and two full baths on one level, perfect for guests, income, or in-laws.

21 Hemlock Rd, Roxbury

21 Sharon Canaan Rd, Salisbury
$1,525,000
4 Beds ⋅ 3 Baths ⋅ 24094413 MLS
Set on 13 tranquil acres with privileged access to the Housatonic River, this gracious Salisbury property offers an exceptional country retreat in the heart of Connecticut's Litchfield Hills. The beautifully renovated 4-bedroom, 2-bath Colonial residence showcases bright, thoughtfully designed living spaces that complement the natural landscape surrounding the home. The welcoming interior features an open-concept floor plan where the living room flows seamlessly into the dining room with fireplace, adjoined by a well-appointed kitchen with a comfortable breakfast nook. A private first-floor bedroom suite with full bath provides ideal accommodations for guests or single-level living. Upstairs, three additional bedrooms share another full bath, while the home office includes a dedicated staircase leading to a versatile bonus area perfect for a studio, home gym, or media room. The extraordinary grounds boast 1,000 feet of river access along the picturesque Housatonic, with level lawns extending toward the water. A charming three-stall barn anchors one side of the property, balanced by a lovely orchard on the opposite end-all embraced by the peaceful ambiance that comes with proximity to one of Connecticut's most cherished waterways. Located at 21 Route 7, this distinctive property embodies the essence of Litchfield County living while offering easy access to Salisbury's village amenities, regional cultural attractions, and outdoor recreation.

21 Sharon Canaan Rd, Salisbury

61 E Main St, Salisbury
$1,512,500
4 Beds ⋅ 4 Baths ⋅ 24168327 MLS
Meet Madeline. This historic 1840 New England farmhouse is an understated, in town masterpiece that immediately establishes a profound sense of place. Greeted by classic pillars and an inviting French blue front door, you are perfectly introduced to the timeless elegance that lies within. Step inside the center hall foyer and you are greeted by a classic center hall staircase. To your right, a sprawling living room is anchored by a warm wood-burning fireplace and features a gracious window seat that practically begs for a blanket and a good book. Just beyond, the dining room is generously scaled to host large gatherings with ease. The heart of the home is a thoughtfully designed kitchen that radiates warmth and function. Boasting expansive prep space, an eat in bar, a classic farmhouse sink, and wide-plank floors beneath hand-hewn beams, it offers a beautiful nod to the property's history. It flows effortlessly into the adjoining family room, creating a natural, inviting hub for friends and loved ones. Step outside to the bluestone patio, where indoor-outdoor entertaining becomes seamless. Spending summer evenings hosting barbecues or quietly reading in the private, lush backyard might just tempt you to stay in rather than walking to local culinary hotspots like The White Hart or Fern. When you finish exploring the gardens, re-enter through the dedicated potting room and connecting mudroom, the perfect landing zone for messy boots and fresh-cut flowers.

61 E Main St, Salisbury

76 Cowles Rd, Woodbury
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 24160616 MLS
Rare opportunity to own a spectacular 40-acre estate designed for exceptional horse care, training, and country living-while also offering the flexibility to create a private escape tucked away from it all. This remarkable property features a 150' x 80' indoor riding arena with excellent lighting and three overhead doors, along with an immaculate 9-stall barn complete with concrete floors and mats, stall windows, mounted hay racks, a hay chute, three cross-tie areas, and convenient hay storage with a conveyor system. Additional equestrian amenities include an outdoor wash stall, a 200' x 150' outdoor riding arena with stadium jumps, cross-country jumps woven throughout the property, and a 130' x 65' dressage arena. Five paddocks, 13 outdoor stalls, and ample room for expansion make this an exceptional setup for horse enthusiasts, trainers, or boarding operations. Thoughtfully sited to capture breathtaking views, the custom-built home overlooks the picturesque grounds from a stunning 90-foot wraparound deck. Inside, the cathedral-ceiling great room with a cozy wood stove flows into the kitchen, dining area, and bright sunroom, with French doors opening to the expansive deck for seamless indoor-outdoor living. The main level includes a bedroom and full bath, while the second-floor primary suite offers a walk-in closet and spa-like bath featuring a clawfoot soaking tub.

76 Cowles Rd, Woodbury

253 Tophet Rd, Roxbury
$1,500,000
4 Beds ⋅ 4 Baths ⋅ 24085914 MLS
Quintessential CT Mini- Estate of 2 Homes! Top restoration of 3-Bedroom/2.5 bath Victorian plus a Guest House with giant stunning, heated, saltwater pool, 2nd small spa pool and wonderful stone terraces and open lawns. Historic Pool House Rental Income: $50,000-$100,000 per year. Perfect for generational living as both the Main House and the Pool House have their own pools, driveways and garages. Main house with large wood-burning fireplace and original antique wood floors throughout. Plus a New Vaulted, Open and Airy Pool House with chef's kitchen, bedroom, full bath, finished lower level offering a second full bath and more living space. Charming, covered BBQ Deck overlooking pool and 2-car garage below. Best scenic road for walking or bike riding by historic farms and homes owned by numerous artists, authors, actors and other private luminaries. Mature plantings include beautiful hedges, blue hydrangea, specimen trees -- enough flowers to keep vases full. Barn. Special. Must see!

253 Tophet Rd, Roxbury

169 E Shore Rd, Morris
$1,500,000
3 Beds ⋅ 3 Baths ⋅ 24129401 MLS
Lakefront home completely remodeled 4 years ago plus 2 story detached recreation building. Waterfront with stunning views, waterside deck, gazebo, and walk-in beach. 2166sqft house completely remodeled and with Anderson casement windows, inset custom cabinetry, and hardwood floors throughout. Eat-in-kitchen with custom inset cabinets, Quartz countertops, stainless appliances, breakfast bar island, and backsplash. 2 story great room with fireplace and built-ins. Main level master suite with attached full bath. Additional full bath / laundry room. Office/Den. Upstairs 3 additional rooms plus full bath. Gorgeous bluestone patio with water views. Recreation room outbuilding with wetbar, fireplace, coffered ceilings and wood paneling. 1/2 bath and upstairs fully finished loft playroom. Outdoor shower. Central air, sec sys, irrigation, landscape uplighting, plenty of parking. Gorgeous meandering lot with lakefront and views. Bucolic setting with professional landscaping and plantings throughout the lot and tastefully incorporated into the topography with stone walls, patios, and walkways. Thoughtfully planted trees and shrubbery protect privacy while creating a home away from home atmosphere. Propane tank buried. Town card has 3 bedrooms and 2 bathrooms. Property has extra rooms and 3.1 bathrooms. Attached floor plans are incorrectly labeled. Please ignore room names. See town card for details on year built. Also listed with neighboring property as MLS24122976.

169 E Shore Rd, Morris

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