Sullivan Homes with Gated Amenities

Welcome to Sullivan County, New York – a hidden gem nestled in the picturesque Catskills. Known for its lush landscapes, vibrant communities, and rich history, Sullivan County offers a unique blend of rural charm and modern amenities. Whether you’re seeking a peaceful retreat or an adventurous lifestyle, this county has something for everyone.

Sullivan County is renowned for its stunning natural beauty, featuring rolling hills, serene lakes, and an abundance of outdoor activities. From hiking and fishing to skiing and snowboarding in the winter, the region is a paradise for nature enthusiasts. Additionally, the county boasts a thriving arts scene, delicious farm-to-table dining, and a variety of local festivals that celebrate its diverse culture.

For those seeking a luxurious lifestyle, Sullivan County offers homes with gated amenities that provide both security and exclusivity. These stunning properties often feature expansive grounds, private pools, and beautifully landscaped gardens, creating an idyllic setting for relaxation and entertainment. Imagine waking up to breathtaking views and enjoying the peace of mind that comes with living in a gated community.

With easy access to major highways and proximity to New York City, Sullivan County is an ideal location for those who want to escape the hustle and bustle while still being connected to urban conveniences. Whether you’re looking to invest in a vacation home or a permanent residence, Sullivan County’s gated communities present an opportunity to live a life of luxury, comfort, and tranquility in one of New York’s most enchanting regions. Explore your options today and discover the charm of Sullivan County living!

Newest Sullivan Homes with Gated Amenities

$130,000

1050203 MLS

Distinctly positioned just below the spring-fed source of Black Lake, this iconic woodland homesite stretches along roughly six hundred feet of crystal-clear water. A true four-season stream-side sanctuary, Black Lake Creek is a coveted brook-trout habitat. The property features heritage stone formations, towering oaks, and private woodland seclusion. Set at the headwaters of the Toronto Reservoir and tucked behind the gates of The Chapin Estate, this fully buildable lot is ready for immediate construction. The Chapin Estate encompasses over 2,500 acres of preserved wilderness surrounding approximately 1,750 acres of freshwater lakes. This gated, year-round residential community is renowned for luxury second homes and its close proximity to New York City. Membership to the private, residents-only Lake Club is optional for this homesite. Within the gates, The Chatwal Lodge is located just one mile away, offering dining now and spa services forthcoming. Owners may also obtain a boat slip at the Lake Club, granting access to both Toronto Reservoir and Swinging Bridge Reservoir. Photos and lot lines are provided for marketing purposes only. Buyer to verify all information prior to sale.

Lot 3 Chapin Trail, White Lake

$625,000

4 Beds ⋅ 3 Baths ⋅ 1047015 MLS

Welcome to this meticulously maintained and thoughtfully updated home in the desirable Emerald Green community, where comfort, quality, and resort-style living come together. With 4 bedrooms and 2.5 bathrooms, this pristine property is filled with carefully considered details designed for both everyday living and effortless entertaining. Enjoy a fully matted garage, durable Trex decking, and electric awnings that provide shade and comfort while you relax or entertain outdoors. Inside, the home offers an impressive array of amenities, including an 8-person cedar sauna, a Harman pellet stove insert, a beautifully appointed primary bathroom finished with Carrara marble, and custom wood cabinetry in the kitchen. An energy-efficient geothermal heating and cooling system provides an added benefit, offering the potential for significant savings on heating and cooling costs. Emerald Green offers an exceptional lifestyle centered around three lakes totaling approximately 330 acres. Residents enjoy two in-ground pools overlooking a lakeside sandy beach, a renovated indoor clubhouse with a gym, tennis, pickleball and basketball courts, playgrounds, and a dog run. Whether you're looking for recreation, relaxation, or a welcoming community atmosphere, Emerald Green has something for everyone. With its extensive updates, exceptional amenities, and access to one of the area's most sought-after communities, this home is ready to be enjoyed. Schedule your private showing today and make this beautiful Emerald Green property your own. The seller is also open to and would prefer having all furniture, rugs, Weber grill, crystal, and Lazy Boy furniture convey with the property, providing an opportunity for a truly turnkey experience.

61 Lake Shore Drive S, Rock Hill

$1,250,000

4 Beds ⋅ 4 Baths ⋅ 1034443 MLS

PRICE DROP! A magnificent legacy home in the Catskills’ most exclusive gated preserve. Discretely tucked beneath a canopy of mature oaks on five enchanting acres, Whispering Oak Landing is a custom, owner-built retreat within The Chapin Estate - a prestigious 2,500-acre gated wilderness preserve in the Western Catskills, surrounded by 14,000 acres of protected conservation land. Upon arrival, the rhythm of nature sets the pace: birdsong at first light, afternoons spent hiking or horseback riding along the preserve’s trails, and evenings that end with an indoor or outdoor fire crackling in your private sanctuary. Intentionally oriented to follow the suns path, morning light rises over the vaulted timber living room, while evening light settles beyond the foyer, where a crystal chandelier captures the last rays and scatters them in soft rainbows throughout the house. Inside, a soaring vaulted foyer opens onto expansive, sunlit gathering spaces. Just off the entrance, a convenient powder room sits opposite a bright, oversized laundry room complete with utility sink, exterior access, and direct entry to the two-car garage. The main level centers on a warm, vaulted living room anchored by a stone wood-burning fireplace, a professionally appointed kitchen with double sinks, and a seamless indoor-outdoor dining areas that include a propane grill. The vaulted, east-facing primary suite occupies this primary level for effortless single-floor living. An oversized picture window frames tranquil wooded lake views, while the en-suite bath offers a private sanctuary of indulgence: a windowed soaking tub, dual vanities, walk-in shower, and refined finishes. A stately walk-in closet, discreetly reached via a private hallway, completes the suite with both elegance and practicality. Upstairs, two well-proportioned bedrooms sit at opposite ends of the home, linked by an open corridor with railings that overlook the living spaces below. A naturally lit shared bathroom serves both. One bedroom opens onto a charming Juliet balcony; the other includes a spacious, unfinished dormer room above the garage, ready for future expansion. The lower level provides a cozy, versatile space for relaxation, featuring a fourth full bedroom and an additional flexible room ideal as a fitness studio, reading lounge, or fifth bedroom. Designed for comfort and entertaining, this level also includes a full wet bar, cedar sauna, full bath, and an expansive secondary living room that opens directly onto a graceful flagstone terrace, perfect for indoor-outdoor living. Architectural details throughout include soaring ceilings with exposed pine beams, wide-plank hardwood floors, granite countertops, and central air conditioning, all thoughtfully integrated for true year-round enjoyment. Life at The Chapin Estate unfolds across 2,000 acres of freshwater reservoirs and trout streams, with membership options that include a private Lake Club, tennis and pickleball courts, and a network of trails that winding through the preserve in every season. The property borders the 900 acre Toronto Reservoir, offering panoramic water views from the home itself. Minutes away you'll find the Eldred Preserve and its Homestead Restaurant for farm-to-table dining (with a large spa expansion coming soon), the Bethel Woods Center for the Arts, and the Monticello Motor Club. While homes within The Chapin Estate rarely change hands, and many are still held by their original owners, this is a unique opportunity to acquire a legacy property on the coveted Peninsula at a compelling price. Just two hours from Manhattan by car and fifteen minutes from the newly renovated Sullivan County International Airport, Whispering Oak Landing offers a rare seclusion that never feels remote.

51 Homestead Trail, White Lake

$99,900

1043615 MLS

Experience the quiet elegance of country living in the private, gated lake community of Black Lake Estates. The community’s main attraction is Black Lake, the pristine 250-acre non-motorboat lake. This gorgeous lake offers exceptional fishing, kayaking, canoeing, and peaceful boating reserved exclusively for property owners. Tucked away at the end of a quiet dead-end road, this beautiful homesite overlooks a tranquil natural pond, creating a private woodland retreat. Surrounded by towering trees, lush ferns, blooming mountain laurel, and moss-covered boulders, the landscape is rich with natural beauty. Deer, wild turkey, rabbits, and a variety of waterfowl are frequent visitors, making this a truly enchanting setting for your future home. Ideally located just 90 miles from New York City, you're also minutes from hiking trails, excellent restaurants, Bethel Woods Center for the Arts, Resorts World Catskills Casino, the exclusive Monticello Motor Club, and everything the Sullivan Catskills has to offer. Whether you're envisioning a weekend escape or a full-time residence, this is a rare opportunity to own a piece of one of the area's most desirable private lake communities.

Lot 23 Deer Meadow Road, Bethel

$499,900

2 Beds ⋅ 2 Baths ⋅ 1043200 MLS

This is the kind of lake where quiet is part of the experience. Gas motors are limited to four horsepower, and from this west-facing lakefront cottage the water stretches out in front of the house, catching the sunset from the lakeside deck. Below, a level lawn leads to a sand beach and fixed dock, making the transition from house to water unusually easy. Built in 2008, the cottage is arranged over three levels. The main living space rises to a knotty-pine cathedral ceiling with three arched windows facing the lake and a stained-glass panel set into the center gable. An open kitchen, bedroom and full bath are all on the main level. Upstairs are a second bedroom, another full bath and a generous sleeping loft overlooking the great room. The finished walkout lower level adds a second living space with its own entrance and heat, finished in reclaimed barn board and corrugated tin and anchored by a propane stove set into hand-laid stonework. It opens directly beneath the deck to a sheltered outdoor area overlooking the lawn and lake. Two fire pits, a spring-fed ornamental pond, outdoor shower, two storage sheds and generous gravel parking complete the grounds. The setting is part of the Fallsburg Fishing and Boating Club, incorporated in 1904 and limited to 100 shares, with gated private roads, a clubhouse and a longstanding calendar of member events including fishing contests, a sailboat race, boat parade and Presidents' weekend chili cook-off. Ownership is through purchase of a Club share rather than a fee-simple deed. Purchase is subject to Club approval. Club bylaws provide for seasonal residence. Annual dues are $3,500.

150 (#51) Wildwood Drive, South Fallsburg

$1,299,900

4 Beds ⋅ 2 Baths ⋅ 1041178 MLS

Black Lake Cedar contemporary offers a rare combination of pristine waterfront, complete privacy, and direct access to hundreds of acres of protected New York State land. This meticulously maintained 4-bedroom, 2-bath lakefront home enjoys breathtaking panoramic views and an unmatched natural setting that will remain forever preserved. The warm, inviting interior features rich cedar accents throughout, creating the perfect Adirondack-inspired retreat. A spacious open great room is framed by dramatic floor-to-ceiling windows that fill the home with natural light while showcasing the spectacular lake views. Step outside to the expansive, private deck or relax in the screened porch, where you can enjoy the sights and sounds of nature in every season. The full walk-out basement offers exceptional custom storage, built-in workbenches, and an oversized one-car garage. A paved driveway leads directly to the waterfront, complete with electric lighting for easy evening access. At the shoreline, you'll find a cantilever dock and electricity at the water's edge - perfect for charging your electric watercraft and enjoying effortless days on the lake. Bordering Lake Superior State Park, the property benefits from permanently protected land, ensuring unobstructed views and exceptional privacy for generations to come. Spend your days hiking, picking wild blueberries, swimming, boating, or fishing on one of the area's most beautiful lakes. Lovingly enjoyed by the same owners for 46 years and impeccably maintained since the home was built 30 years ago, this exceptional property is truly move-in ready. Whether you're seeking a year-round residence or a cherished lakeside getaway, this is a place where memories will be made for years to come. Near to Bethel Woods for world-class entertainment, fantastic restaurants, farmers’ markets, motorboat lakes and all the wonderful things the Sullivan County Catskills has to offer!

74 Oxford Drive, White Lake

$579,000

3 Beds ⋅ 3 Baths ⋅ 1037742 MLS

Imagine coming home to your own private woodland retreat, tucked away on nearly 7 acres in Timber Lake Estates, a gated community. Built in 2024, this brand-new raised ranch offers over 2,000 square feet of beautifully finished living space, surrounded by nature and the peaceful feeling of being miles away from it all. Step inside to a bright, sun-filled living room that flows into a gorgeous new kitchen and dining area. With 3 bedrooms and 3 full baths, there’s plenty of room for family and guests. The finished lower level offers even more space for a family room, recreation area, or potential 4th bedroom, along with a heated garage featuring two-zone radiant floor heating. Everything in the home is brand new, giving you the opportunity to simply move in and start enjoying it. Outside, the property unfolds into a beautiful mix of open and wooded land, complete with a private pond and plenty of privacy. But the real magic begins beyond your property line. Timber Lake Estates is a gated community where residents have private access to the beautiful 26-acre, non-motorboat Timber Lake, perfect for swimming, fishing, kayaking, or spending a summer afternoon beneath the community gazebo. The paved private roads are perfect for cruising around in your golf cart or ATV, adding to the laid-back, woodland-paradise feel of the community. And when you're ready to explore beyond the neighborhood, you’re close to Bethel Woods, the Delaware River, restaurants, farmers markets, shopping, a casino, skiing, hiking, and endless outdoor recreation. With the Metro North train 20 minutes minutes away making it even more convenient for commuting, and under 2 hours from NYC, this is a place where you can truly slow down without giving up convenience. A brand-new home, nearly 7 acres, and a private lake community—welcome to your woodland paradise.

26 Summit Drive, Barryville

$3,595,000

4 Beds ⋅ 8 Baths ⋅ 1037747 MLS

Discover the Mayfly Inn at The Chapin Estate, an Adirondack-inspired lakefront sanctuary where rustic elegance meets refined leisure. Tucked within a private natural setting, this exceptional compound has been thoughtfully curated for those who value craftsmanship, comfort, and the timeless allure of waterfront living. From the moment you arrive, Mayfly Inn reveals itself in layers. Warm wood tones, lodge-style architecture, and bespoke details create an atmosphere that feels both elevated and effortless. The main living spaces are designed for gathering—grand yet inviting, with a natural flow that encourages conversation, connection, and quiet moments by the fire. Beyond the traditional bedrooms, the home offers additional bunkrooms and flexible recreational spaces, ideal for hosting extended family and accommodating guests with ease and sophistication. Curated furnishings ensure the home is ready to enjoy from the very first day. Exceptional features of this home include a full dog wash station, billiard's corner, full bar in lower den with lake view and a stone archway leading to an artfully designed wine cellar. Outdoors, the property is truly a private resort. An oversized connecting breezeway serves as a covered deck for outdoor dining and fireside chats. In the distance, a dock extends into the waters of the Toronto Reservoir, offering a front-row seat to sunrise paddles, afternoon swims, and evenings when the lake turns to glass. The grounds are enriched with thoughtful amenities, including a charming putting green perfect for leisurely practice or friendly competition. A 4-seater ATV makes navigating these 5 acres a breeze. Every corner of Mayfly Inn is designed to elevate the experience of being here—whether it’s a summer weekend filled with laughter, a crisp autumn escape, or a winter retreat where the world feels wonderfully still. This is more than a lake house; it’s a place where memories gather, traditions deepen, and the beauty of the Catskills becomes part of your everyday rhythm. Mayfly Inn invites you to live luxuriously while being connected to the water, the land, and the people that matter most. Located at the Chapin Estate, a 4-season gated residential preserve on 2,500 acres of pristine forest lands bordering 14,000 acres of forever wild conservation properties. Unique attributes include: 1,750 acres of freshwater lakes and trout streams; 9+ miles of hiking, biking and snowshoe trails; Members only Lake Club; Security patrolled and Concierge Services. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey.

60 Top Ridge Trail, White Lake

$695,000

6 Beds ⋅ 3 Baths ⋅ 1034438 MLS

Occupying the eastern point of Treasure Lake, facing due west, this spacious 6 bedroom duplex boasts the most magnificent sunsets in the Catskills, cascading behind a scenic island, mirroring water and sky. Designed and built by a builder as his personal home, this sturdy retreat features an intuitive interior and elevated exterior landscape rarely found in lakefront homes. Built in 2009, This comfortable home offers year-round lakefront living with plenty of room to spread out, entertain, and take in the views. Upon entering the foyer, the home opens into two living levels with three bedrooms on the ground level, and three upstairs. A vaulted great room with dramatic ceiling height features a propane fireplace, built in entertainment center, and wide picture windows framing the lake. The open kitchen features granite countertops, a large center island, stainless refrigerator, and sliding glass doors leading to a covered deck, perfect for outdoor grilling & dining, lounging, and watching the light dance across the water. An additional indoor sitting room can easily convert into a formal dining room. A gallery hallway leads to a spacious primary suite, two sumptuous bedrooms and a recently updated hallway bathroom. Spreading behind its double doors, the primary suite spans the entire northern wing of the upper level. The bedroom itself offers vaulted ceilings and peaceful lake views, leading seamlessly into a generous windowed en-suite bath with a whirlpool soaking tub, standing shower, and dual sinks. Beyond the bath, the suite expands into a large formal dressing room and a sun-filled lake-facing bonus room, accessible through French doors, and can function beautifully as a private sitting room, office, nursery, or additional bedroom. The lower level offers an additional living zone with three more bedrooms, a third full bath, a second propane fireplace, and a walk-out family room with a second expansive deck, a perfect level for guests, multi-generational living, or a dedicated recreation floor. Additional interior features of the home include central heat and air conditioning, an oversized 2-car garage, and double entry door. Exterior highlights include a paved circular driveway, leveled lawns leading to the shoreline, a high-yielding vegetable garden with imported soil, and a garden shed. An adjacent vacant lot is also available for sale, ideal for privacy, future expansion, or an additional homesite. Affectionately considered the crown jewel of the Catskills, Emerald Green is a desirable lake community comprised of three pristine mountain lakes. World class amenities include a newly installed olympic-size pool, splash pool, beach, marina, tennis, pickleball, basketball, fitness center, clubhouse, dog park, and year-round events. Dues are $850/year plus a temporary $725/year assessment for newly upgraded facilities. Dock slips are available at the marina for pontoon boat owners. Short-term rentals are not permitted, and long-term rentals are allowed only after two years of ownership. Centrally located near Rock Hill and Monticello, the region offers a diverse selection of shopping and dining, healthcare facilities, the Bethel Woods performing arts center, Kartrite waterpark, Resorts World casino, a championship golf course, breweries, and charming towns such as Narrowsburg and Livingston Manor. Minutes from a grocery store and acclaimed dining such as Cellio Steakhouse, Lotus, and Dos Gatos. Other nearby attractions include the Monticello Motor Club (currently developing a boutique hotel), the Eldred Preserve (resort and wedding venue), and the premium Chatwal Lodge at the Chapin Estate. Just 90 minutes from Manhattan by car, this home offers the perfect blend of year-round living, weekend escape energy, and lakefront serenity, cradled within one of the Catskills’ most amenity-rich communities.

61 Lake Shore Drive W, Rock Hill

$825,000

3 Beds ⋅ 3 Baths ⋅ 1031460 MLS

Verdant Forest Hideaway- Paradise awaits at 111 Deer Meadow Road; a private woodland retreat nestled within the prestigious gated community of Black Lake Estates. Tucked beneath a canopy of mature trees and surrounded by gently meandering streams, this exceptional contemporary home is perfectly positioned on 5.02 secluded acres, offering a rare combination of luxury, tranquility, and natural beauty. Spanning 2,765 square feet, this thoughtfully designed residence features three spacious bedrooms and three full bathrooms, blending modern comforts with a peaceful, nature-inspired setting. Recent renovations include a beautifully updated chef's kitchen and tastefully remodeled bathrooms, while central air conditioning and a whole-house generator provide year-round comfort and peace of mind. The inviting floor plan offers generous living spaces filled with natural light and picturesque views of the surrounding forest. Whether you're entertaining guests or enjoying a quiet evening at home, every room has been designed to embrace the property's serene setting. The finished basement adds valuable flexible space, perfect for a recreation room, home office, fitness area, media room, or guest accommodations. Step outside and immerse yourself in your own private sanctuary, where the soothing sounds of flowing streams and abundant wildlife create an atmosphere of complete tranquility. Beyond the property, residents of Black Lake Estates enjoy exclusive access to Black Lake, a pristine, approximately 225-acre private lake ideal for swimming, fishing, kayaking, canoeing, paddleboarding, and other non-motorized boating activities. Whether you're spending the day on the water or relaxing along the shoreline, the lake offers an exceptional outdoor lifestyle in a peaceful natural setting. While the home feels wonderfully secluded, it is just a short drive from many of the Catskills' most sought-after destinations, including Lake Superior State Park, Bethel Woods Center for the Arts, White Lake, Resorts World Catskills Casino, and The Kartrite Resort & Indoor Waterpark. This remarkable property offers the perfect balance of privacy, recreation, and convenience, making it an ideal year-round residence or luxurious weekend retreat.

111 Deer Meadow Road, White Lake

$175,000

1028197 MLS

Discover the perfect setting for your dream home on this beautiful 10.65+/- acre parcel featuring frontage on Wesserlauf Pond, with land extending on both sides of the pond for a truly unique and private setting. Mostly cleared and level, this property is ready for your custom home, weekend retreat, or peaceful country escape. Enjoy lake rights to Black Lake, a tranquil 250 acre non-motorboat lake ideal for kayaking, canoeing, fishing and relaxing in nature. Conveniently located near shopping, dining, and the renowned Bethel Woods Center for the Arts, you'll have the perfect balance of serenity and accessibility. Best of all, you're just two hours from NYC, making this an ideal getaway or year-round residence. Build your vision in the Sullivan County Catskills, where natural beauty, recreation, and convenience come together.

Lot 33 Black Lake Road, White Lake

$1,050,000

3 Beds ⋅ 3 Baths ⋅ 1029181 MLS

New Construction with Private Lake Access on 5+ Acres Summer camp, all grown up. A new construction release from Beyond the Black Box, Timber Lake is a contemporary residence inspired by the relaxed optimism of classic midcentury lake houses. The home balances modern architecture with natural materials, handcrafted details, and a warm, collected aesthetic that feels established from day one. Arriving beneath a generous roofline, a welcoming entry opens to soaring ceilings and an expansive great room anchored by a sunken conversation area that invites you to slow down. The kitchen was designed to gather and cook, featuring customized cabinetry, sculptural lighting, stone surfaces, and a generous island equally suited to everyday living and effortless entertaining. The private primary suite includes a detailed bath, walk-in closet, and attached den. Additional bedrooms, two guest baths, and a flexible second den provide space for guests, remote work, or long weekends with family and friends. The walk-out ground level extends the home's living space, offering room for guests, recreation, media, or quiet weekends at home. Outside, the home was thoughtfully positioned to preserve both privacy and the surrounding landscape. A spacious rear deck, fire pit, outdoor shower, and woodland trail leading toward the lake make outdoor living an effortless extension of the home. At the heart of Timber Lake Estates is an approximately 26-acre private spring-fed lake with a residents-only beach, dock, and swimming area. Kayaking, canoeing, paddleboarding, fishing, walking, cycling, and winter skating are all part of everyday life, while mature trees preserve an uncommon sense of privacy. Located approximately two hours from New York City, with NJ Transit service in Port Jervis just 30 minutes away, Timber Lake sits at the center of a quietly emerging pocket of the Catskills where artists, designers, chefs, and makers are reshaping the region without losing what made people fall in love with it in the first place. Barryville, Narrowsburg, hiking trails, farmers markets, destination dining, independent shops, and a growing creative community are all just moments away.

167 Timber Lake Drive, Eldred

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