Highland NY Real Estate & Homes for Sale

Sharon Cottage on 10+ acres - A spectacular parcel of land with building potential and a well-kept 2-bedroom, 1-bath cottage greeting the 10 prestigious Sharon, CT acres. The upper building site was approved in 2011 and awaits the vision of its next land steward. An existing Cottage on the property offers immediate use and enjoyment of the homestead. Views from the upper lot, privacy for both the Cottage and potential building site, and only minutes to town. This property offers the ultimate country retreat and a blank canvas for those who dream of creating a homestead that echos their lifestyle. Minutes to: Sharon Town Beach, Mohawk Ski Area, Sharon Audubon, Millerton, NY, Salisbury, CT, Metro North's Wassaic Station.

Very Special & Architecturally Significant Home just off Cobble Road in Kent and featured in the NY Times: 4 bedrooms, 4.5 baths, room to spread out, and full of natural light. With just over 2 acres and open views, this wonderfully maintained Frank Lloyd Wright-inspired home sits on Cobble Heights Road about 5 minutes from downtown Kent. Built for entertaining and a floor plan that creates privacy and separation within the home. Terrific location, with convenience to NYC via Metro North (20 minutes to Harlem Valley Wingdale). If hiking is your thing, trails abound including Kent Falls State Park, and the town of Kent is one of the more sought-after in Litchfield County, with many highly rated restaurants and shopping options. Less than two hours to NYC but a world away in bucolic Litchfield County.

IN-TOWN Antique Cape on the Sawmill Brook in the heart of SMALL TOWN USA! A wonderful location for anyone that wants to be IN-TOWN but not on the main road. Across from Sherman Library and a short stroll down to community Veterans Park, jogging path, basketball court, tennis & pickle ball courts. 1/2 M to Town pavilion and Town Beach on CANDLEWOOD LAKE! Walk to School, shopping, restaurants, grocery store. Comfortable Cape that can suit a variety of needs. In-Home occupation would be a big PLUS due to both a flexible floor plan (Main Level Bedroom could also be used as an in-home office space). Updated Kitchen & Dining Area. Charming LR w/stone fireplace and wood beams. Upper Level w/2 secondary bedrooms and full Bath. BONUS versized 2 CAR DETACHED GARAGE that boasts a huge finished loft area as well as an additional drive-in storage lower level! This type of opportunity does not come along very often in SHERMAN. House is located in the Commercial/Residential Zone but not in the Historic Zone. Property being Sold "AS IS".

Originally constructed in 1739, this delightful Antique is nestled in Kent's picturesque Flanders Historic District, right along scenic Cobble Road. Steeped in history, the home boasts many original features, from its wide board floors to the central chimney that serves two fireplaces in the living and dining rooms, not to mention the charming hand-hewn beams overhead. Meticulously maintained, the original house has undergone a thoughtful expansion, creating a generous open-concept space that seamlessly blends a modern kitchen with high-end stainless steel appliances and butcher block counters, flowing into a sun-drenched dining area and seating area adorned with custom built-in bookcases. Venture upstairs to discover the primary bedroom with its luxurious en suite bathroom, flanked by two additional bedrooms sharing a bath. The walk-out lower level offers a versatile large room that could easily serve as an overflow bedroom, accompanied by a full bath. The property also features a grand party barn and a separate studio, adding an extra living space ideal for a home office or a future guest home. Outside, the 2.4-acre property borders Cobble Brook and showcases a serene pond, enchanting vegetable and flower gardens, a charming grape arbor, and a fruitful orchard, creating an absolutely idyllic setting.

Beautiful contemporary on 3.33 private acres surrounded on three sides by 0pen Space, providing exceptional privacy and views of pastures and hills. The great room ( living room/dining room) has a 16' cathedral ceiling, and floor-to-ceiling, two-story windows looking out onto gardens and protected land. Large country kitchen with Sub Zero, Miele, and Wolf appliances and a large butcher block central island. There is a working wood stove in the kitchen. The back kitchen wall is also floor-to-ceiling glass, with a wrap-around deck connecting the kitchen and dining room. This home offers three large light-filled bedrooms, and 3 full and one half fully renovated baths, with two of the bathrooms having heated floors. The primary bath offers an immense shower, a deep soaking tub, and a heated Toto bidet. Metal roof, a brand new state-of-the-art geothermal system, and new front and back decks. Long granite-lined gravel driveway with a center island. Large open yard with professional landscaping, and an Enchanted Forest, complete with a mini castle, log cabin, medieval size fire pit, swings, climbing ropes, and magical trails through the woods. This home is warm and welcoming, light-filled and comfortable, move-in ready.

[ONE OF A KIND] This house has it all. Located in the desired Atchison Cove private lake community the house sits atop a hill, safely tucked away from the road and features everything a family may desire: boat dock, large inground gunite pool with a slide, kids' playground, volleyball, supersized deck, magnificent library, 2 floor game room, 3 fireplaces, giant kitchen, separate dining room, 4 bedrooms, 3.5 baths, huge laundry room, custom built office, 2 car garage + access to tennis courts and Sherman School with it's very small class sizes, close to Pawling MetroNorth station and an hour from NYC by car separates this house from anything else on the market. Experience the better way to live on Candlewood Lake (with a boat dock, sandy beach, kayak rack, clubhouse and amazing Atchison Cove neighbors).

Uninterrupted VIEWS and privacy, protected by land trusts / conservancy on 50+ acres in South Kent! Superbly located on a town maintained, scenic road surrounded by established country estates. Incredible opportunity to expand the existing 3 bed cottage or use it as a guest house and build your dream home on a higher elevation to capture further views and magnificent sunsets! The property abuts Long Mountain-Mud Pond Preserve which is a 400 acre network of conservancy lands. The unique features of this land include level areas for a lawn and swimming pool, multiple sites for a new / additional house, trails through the trees, stone walls, gently sloping hills, a Large Barn and direct waterfront access to Mud Pond. Opportunity to sub-divide or enjoy tax advantages by donating part of the acreage to a Land Trust, thus ensuring unspoiled views for generations. Located only a few minutes drive south of the picturesque village of Kent for galleries, restaurants, shops, etc. This property presents opportunities to subdivide & consists of two lots: 39.36 acres in Kent; 12.5 acres in New Milford. Easy access to NYC via rte 22 and Wingdale train station. The land is steeped in history, having previously been owned by one family for several generations. In the past, part of the land was used for night pastures and the property has been discussed in detail by Adam Halasi Kun in his book entitled "The Unknown Right."

Meticulously renovated home filled with a sense of warmth and connection to nature, where the open space flows seamlessly from room to room. Upon entering the living area, the welcoming fireplace draws your eyes to the double height ceiling with natural wood clapboard and exposed beams. This space is large enough to accommodate a dining area. Double doors lead to the Den/TV room with high ceilings & new skylights. Alternatively, this room could be used as a bedroom. The kitchen opens to a large screened-in porch overlooking the pool - a magical place to spend the evening whilst enjoying the stunning illuminated pool area. A guest bedroom and full bath are also on the main floor. The primary bedroom suite comprises the whole upper level with an incredibly luxurious en suite bathroom. The bedroom itself has a wood burning fireplace, deep closet and dual exposures overlooking the landscaped yard. Downstairs, the finished lower level is perfect for a home theater, game room or additional living space. A further bedroom and full bath is located on this level. Porcelanosa floor tiles throughout this level including the utility room. The quality & style in each of the 3 baths must be seen to be appreciated- radiant floor heating! Outside, the pool was recently upgraded. Easy access to parks, shopping, dining, hiking, Sherman town beach & Candlewood Lake for watersports. This remarkable home is an embodiment of modern luxury living and is move-in ready for the most discerning buyers.

This Contemporary home underwent a complete redesign and renovation in 2002 by architect Stephen Lazar, resulting in a distinctive modern aesthetic. Situated directly across from Irene's Woods - a 60-acre land trust parcel with scenic trails - the property is nestled within the Atchison Cove lake community. Residents here have exclusive access to a private sandy beach, a clubhouse available for events, and leased dock space on Candlewood Lake. The home's layout features a private primary suite with FP on the upper level, while the main level comprises a spacious study, dining room, living room, and kitchen. The lower level offers a media/recreation room with a wet bar, two additional bedrooms, and a fitness room conveniently adjacent to the outdoor shower and hot tub. Each room is thoughtfully designed, boasting oversized sliders and/or windows that frame the picturesque outdoors. Newly refinished Brazilian cherry floors grace the interior, complementing the sophisticated details and upgrades, such as custom picture light outlets, a dual-sided fireplace, commercial ice machine, two wet bars, indoor steam shower, heated garage, and a 600-bottle temperature-controlled wine cellar. Seasonal mountain views and expansive decks on two levels, with direct access from most rooms. A community consisting of 55 homes, Atchison Cove offers residents a serene lakeside lifestyle and stunning southerly lake vistas, making it a coveted retreat in a beautiful Candlewood Lake community.

Timber Trails Charmer turned thoroughly modern! A true country subdivision on the Sherman/New Fairfield Line. Terrific location for commuters - 1M to NY Line. Low maintenance country setting with level side yard and seasonal Views of Valley Pond.Main Level living w/versatile floor plan. Foyer opens to both the Living Room and 3rd BDRM/OFFICE. A fantastic Breakfast Nook/Media Area flows into an open Dining Area and new Kitchen. The primary bedroom offers a full bath and walk-in closet. The secondary bedroom also has its own private bath. There are sliders off this bedroom to a 12 x 11 balcony/deck. Lower Level offers a 22x10 utility/laundry/storage area plus 21 x 11 Garage. Updates/Upgrades include - roof/siding/windows/wiring/Kitchen/Furnace/AC Ductwork/200 Amp Service.. Remodel/New Baths. New Plumbing for Kitchen/both Baths. Note-Front deck being removed and being replaced with stone patio. Back Deck/Balcony remains. B-100 on file. Taxes will be updated once final CO obtained. 5M to community facilities - Veterans Park, jogging path, basketball court, tennis & pickle ball courts, Town pavilion, Town Beach and kayak/canoe racks & boat slips on CANDLEWOOD LAKE! 45M White Plains/60M Manhattan. It's a wonderful life in small town USA!

Deer Run Shores - Water Front Lake Community on Candlewood Lake with your own boat slip. Step into your very own oasis, where every day feels like a vacation retreat with seasonal views of Candlewood Lake! 4-bedroom, 3 full bathroom home with large windows that floods the home with natural light. Sliders off of the kitchen leads to the wrap around porch and fireplaces are on both levels. Your backyard paradise awaits you with a walking trail, gardens and a man made pond. Whether you're hosting a backyard BBQ or reading a good book this is your chance to live the vacation lifestyle everyday. Amenities at Deer Run Shores include clubhouse, pool, beach area, boat slip, kayak/canoe racks and boat storage. This fantastic location provides easy access to the town center, 20 minutes to the Metro Train Station which takes you to NYC. Convenient access to shopping centers, local attractions, Danbury Fair Mall, restaurants, hospitals, medical facilities, skiing, snowboarding, apple picking, wineries, and breweries all are near by. Plus, benefit from Connecticut's lower taxes compared to New York. Home being "sold as is".

Stunning Colonial in the serene and picturesque community of Timber Trails on the New Fairfield/ Sherman border. An short commute to NY and Metro North. The magnificent country kitchen is the heartbeat of this home including professional grade Wolf appliances, large granite island and custom cabinetry. Notice the hardwood floors throughout the home and custom millwork including specialty beveled glass French doors. Large primary suite with 2 walk in custom closets. One en suite bedroom, 2 additional large bedrooms, a full bathroom and large laundry room complete the second floor! Beautiful stone work, lovely mature plantings and patio with views of the pond. This home has all the high end finishings you've been looking for with the low taxes of Sherman. If you are looking for a pool, an engineered plan has already been done and is ready for you to put one in! Welcome home!

The "Mare's Nest" is a lovely 1890's equestrian property which has been home to the same family for the last 50+ years. The main house is a colonial featuring some fine original details with more recent additions of a greenhouse and a main floor bedroom wing that adds an additional kitchen, laundry and great room. There are a total of 4 fireplaces, 4 bedrooms and 5 bathrooms. The stables and a number of other outbuildings add a great deal of charm to the rolling 27 acres of lawn and pastures highlighted by the bucolic swimming pond. The heated inground pool is conveniently accessed from the great room and primary bedroom. There is a hot tub and a small pool house for storage of pool toys. The stable was home to many thoroughbred racehorses over the years and has 6 stalls and a fenced paddock. The 2 barns have 9 garage bays and lots of room for equipment storage. Conveniently situated near the village of Millerton NY and a 20 minute drive to the NY train at Wassaic.

A remarkable opportunity to own and renovate a home across from Sharon Hospital in the Village of Sharon, Ct. This home is in the center of Sharon and all that offers, such as the restaurants, library, hospital and all the associated doctor's offices. This home is served with both Town water and sewer and is minutes away from the train station to NYC.

Charming Cape in Ideal Location - This lovely Cape Cod home located on an amazing lot in idyllic Sharon CT is now available for sale. Cross the threshold of the extra deep wrap-around porch and enter the home with hardwood floors and generous proportions. The light-filled kitchen has a dining area with a large bay of bowed windows overlooking the side yard. A laundry room/mudroom is adjacent. The living room features an extra large double-height stone fireplace that has doors to a heated sunroom with wrap-around windows and access to the back patio with gorgeous views. The main floor primary bedroom has its own stone fireplace, a private sunroom, an en-suite bath, and ample closet space. Ascend to the second floor to discover two guest bedrooms and a full bath, providing comfortable accommodations for family or visitors. A detached two-car garage with loft storage space accompanies the property, featuring an attached room housing an exercise pool, perfect for relaxation and fitness. Enjoy the peaceful ambiance of country living, with convenient proximity to local amenities including in-town shopping, the Sharon Playhouse, Indian Mountain School, Hotchkiss School, and easy access to NYC train transportation. Don't miss the opportunity to make this tranquil retreat your own.

Candlewood Lake Community with Pool, Clubhouse, Beach and Docks. Updated, Well Maintained, 3 Bedroom Raised Ranch in Desirable Deer Run Shores Community. Many Updates in last ten years: Kitchen, Stainless Whirlpool Appliances, Baths, Windows, Roof, Driveway, Hot Water Heater, Well Tank, Carpets, Lighting, Electrical, Plumbing, Insulated Garage Doors, Lift Master Garage Door Openers, Mini Split for Heat and AC. Upper Level has Hardwood floors with Herringbone and Inlaid Details, Sliders to Large Deck Overlooking Spacious Backyard. Finished Lower Level with New Carpet, Built-ins, Lopi Wood Stove, Laundry and Half-bath. Oversized, Insulated Garage with Newer Insulated Garage Doors and Lift Master Openers. Private Candlewood Lake Community. Low Sherman Taxes, 90 minutes to Manhattan. Great Full time or Weekender Home.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,872 sq ft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplace, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

Capture the history and grandeur of Great Elm, the unparalleled 19th century Georgian colonial estate that was once the childhood home of author and influential political commentator, William F. Buckley Jr. Nestled in the heart of Sharon, CT, this prestigious property is a rare opportunity to acquire a residence steeped in historical significance and architectural elegance. Great Elm boasts 8,872 sq ft of luxurious living space, crafted with impeccable design choices throughout. From the art deco bathrooms to the William Morris wallpaper, every room exudes sophistication and meticulous care. William Buckley Sr. purchased the original 1812 house in 1923, expanding it over time to accommodate his growing family. The main level primary bedroom suite and gracious sitting rooms, each with gorgeous detail and wood burning fireplace, open to the dramatic three-story Atrium, a year-round haven reminiscent of New Orleans. Upstairs are 7 beautifully appointed ensuite bedrooms, one of which is used as a gym; another as an office. This property is the anchor of a community of homes joined by an Association that manages the 50 magnificent, park-like acres and amenities, including a heated, Gunite pool, pool house, tennis and paddle/pickle courts. This spectacular property in the beautiful Litchfield Hills is more than just a residence; it's a chance to own a piece of U.S. history. Close to Hotchkiss, Salisbury, Indian Mountain and Millbrook Schools. Only 2 hours to New York City.

107 Main Street is located in the heart of Sharon's Historic District - a tucked away convenient village setting. Originally the carriage barn to a neighboring home, it was reimagined by a previous architect owner. Brimming with character and charm, this 4 bedroom, 2 and a half bath home offers a spacious & historic layout. The ground floor has 2 entrances: a main entrance foyer, and a sun-lit mudroom with slate tiles which opens to a large kitchen with a central island and new appliances. Next to it, a separate formal dining room with a secondary staircase that leads to the upstairs bedrooms. The cozy family room has custom built-in cherry cabinets and bookshelves, a large double-flue fireplace and french doors that open to an expansive, peaceful cedar deck and a bluestone patio, providing ample outdoor gathering space. Impress your guests with the full-height great room ceilings from the main entrance, two large skylights and a second fireplace. Entertain in the sunny living room that overlooks an established perennial garden. Continuing upstairs by way of a wide formal staircase, you'll find a lofted second level with exposed wooden beams throughout. Off the loft is the primary bedroom with a Palladian window, high ceilings, and a walk-in closet. Through the opposite side of the loft, are 3 additional, and generously sized bedrooms with another full bath, newly renovated. This rich in character historic home off the Sharon Green is not to be missed.

Your lakehouse retreat in Deer Run Shores, Sherman is the perfect blend of modern and comfort. Panoramic lake views can be enjoyed from almost every room in this renovated, private home. The open floor plan on the main level, complete with 8" oak plank floors walks out to a wraparound deck from the dining area, living room, and main level on-suite bedroom whose wall to ceiling windows provide year-round vistas of sunrises at Candlewood Lake. The main level's kitchen offers culinary comforts and opens to the dining area with brand new walnut mid-century style bar and flows seamlessly into the living space complete with floor to ceiling stone fireplace. Additionally, the office and second tv/flex space room (featuring cork floor for sound protection) with an adjacent second full bath on the main level are perfect for working from home or a tucked away oasis from the busyness of life. All four bathrooms have been totally renovated. Moving upstairs the entire upper level is a primary bedroom with private deck, bathroom with large soaking tub, standing shower, and an expansive walk in cedar closet. The lower level offers three large bedrooms that open to a house-length fieldstone patio and screened-in porch which boasts a gas fireplace and access points leading down to the lake. Lakeside you find another deck and dock perfect for summer swimming in the calm waters of the cove just off the main lake. This bucolic setting with many mature plantings, is the perfect lakeside retreat.

Come see a very private ranch home, nestled away with a very private patio with swimming, pool and fire pit. close to all amenities. Only 6.4 miles away from Harlem Valley Wingdale train station and only minutes away from downtown New Milford , Sherman, Kent along with lake Candlewood. The house is situated on .49 acre lot and two separate lots are being sold with house sold as is !

Sitting on top of Mauweehoo Hill, transport yourself to this nature lover's paradise where privacy abounds! This quiet cul-de-sac is nestled in the beautiful hills of Sherman. Enjoy the rainbow of colors from the spectacular sunrise every morning on your Trek RainEscape deck. Overlook your cottage style pollinator gardens, and rolling stonewalls that make up this majestic property. Crafted as a truly self-sufficient property, pick several varieties of apples in the lower apple orchard, or continue to grow your own food in any one of many vegetable or herb gardens. Improvements abound as the owner added new roof, new HVAC system, new triple pane Marvin windows in lower level, hydro radiant floors in the solarium and two lower bedrooms and baths, new well pump, new electrical service to the garage, main chimney was rebuilt with copper flashing and two other chimneys have been realigned and lower level fireplace has new insert. The foundation was recently resealed as well and the home is wired downstairs and outside for surround sound. Have piece of mind to never lose power with the whole house Generac. This approved five bedroom, five full bath home is ready for its new owners who can still make it their own with needed bathroom upgrading and other work on the main level of the home. Just a few minutes from the Harlem line train station in Pawling, work from home or take the train into the city when needed! This very prestigious area of Sherman awaits you!

Welcome 23 Twin Oaks to the market! Conveniently located right off route 7, this spacious townhouse in a sought after community is the perfect place to make home. Sunlight pours through the windows and skylight of the main floor, creating an inviting entertaining space, with a floor plan, fireplace, and soaring ceilings to accommodate everyone. Upstairs you'll find two good sized bedrooms and a full bathroom. The lower level with walkout features loads of storage space, which could easily be finished for more living area, or even an additional bedroom! This home provides easy access to all points in New Milford, as well as locations throughout central Litchfield county. With a short drive you can enjoy all the amenities the town center has to offer, including nightlife, weekly farmer's market, live music on the town green, and countless community activities. Enjoy access to hiking, nearby lakes and other outdoor activities...Approximately 30 minutes to Danbury, 20 minutes to I84, and 15 minutes to the Wingdale Metro North stop. Schedule your appointment today!

Chic In Town Period Home Set on Prominent Upper Main St. 4 Bedrooms, 3.5 Updated Baths. Central A/C. Welcoming Public Spaces Loaded with Charm. Large Living Room with Fireplace & Floor-to Ceiling Windows. Inviting Family Room with Wood Stove & Doors to Private Stone Terrace. Formal Dining Room with Built-Ins. Screened Porch. Open Eat-in Kitchen with Butler Pantry & Back Staircase. 2 Primary en-suite Bedrooms + 2 Additional Bedrooms. Coveted Historic District Gem!

Welcome to 1 Jackson Hill Road. With its refinished wood floors and rustic ceiling beams this home blends modern comfort with historic details. The spacious living room with its cozy fireplace, flows naturally into the well-appointed kitchen and formal dining room. Natural light pours into this delightful cottage from the dining room bay window and the sky lights in the renovated bathrooms. Set off the main living area is the first floor primary en suite with ample closet space and soaring ceiling height. Upstairs the second bedroom boasts sturdy built-ins. The enchanting curb appeal is created by mature landscaping and flourishing perennials. A detached garage provides additional storage.