Sullivan Homes with Security Amenities

Welcome to Sullivan County, New York—a hidden gem nestled in the heart of the Catskills, where nature's beauty meets modern living. Known for its lush landscapes, vibrant communities, and rich history, Sullivan County offers a unique blend of rural charm and contemporary convenience. With its picturesque lakes, rolling hills, and extensive outdoor recreational opportunities, this county is perfect for those seeking a serene lifestyle without sacrificing access to urban amenities.

Sullivan County is home to a diverse range of homes, many equipped with top-notch security amenities to ensure peace of mind for residents. Whether you're looking for a cozy cabin, a spacious family home, or a luxurious estate, you’ll find properties that prioritize safety without compromising on style. Many homes in the area feature advanced security systems, gated entrances, and community surveillance, allowing you to enjoy the tranquility of rural living while feeling secure.

Beyond the homes, Sullivan County boasts a vibrant community spirit, with local events, farmers' markets, and cultural festivals that bring neighbors together. The county also offers excellent schools, healthcare facilities, and a variety of shopping and dining options, making it an ideal place for families, retirees, and everyone in between.

If you're ready to explore the perfect blend of comfort, safety, and natural beauty, Sullivan County is waiting for you. Discover your dream home in this enchanting region and embrace a lifestyle that celebrates both relaxation and adventure. Your new beginning starts here!

Newest Sullivan Homes with Security 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.

Chapin Trail, White Lake

$749,000

5 Beds ⋅ 3 Baths ⋅ 1049202 MLS

LAKEFRONT LIVING AT IT'S BEST - Come home to exquisite lakefront living in this spacious contemporary retreat in the exclusive Emerald Green community. Designed to showcase its spectacular private lake views, this three-story, 5-bedroom, 3-full-bath home offers an inviting open-concept layout, soaring cathedral ceilings, multiple outdoor spaces, and a generous backyard leading directly to the lakefront. The main level features a bright, open floor plan encompassing the kitchen, dining area, and living room, all oriented toward the breathtaking lake view. The living room features a beautiful stone propane fireplace, creating a warm and inviting gathering space. A bedroom and full bath complete the main level. Upstairs offers two rustic bedrooms and a full bath, all opening onto a beautiful lake-facing landing. The walkout lower level opens directly to the backyard and lakefront and features gorgeous bluestone tile flooring, a spacious game room/family room, a second stone fireplace, two additional bedrooms, a recently renovated full bath, and a convenient laundry/mudroom. The outdoor living area is exceptional, with renovated front and rear decks ideal for entertaining, relaxing, and enjoying the spectacular setting. A recently built large storage shed provides space for all your lake and outdoor gear. Parking is plentiful, with a two-car driveway in front plus a separate side driveway accommodating 6+ additional cars. With lake views from virtually every level and direct access to the peaceful private lakefront, this is a home built for relaxing, entertaining, and creating memories with family and friends. The Emerald Green amenities include a full access fitness center, with indoor and outdoor basketball, tennis, and pickle ball courts, dog park, several pools, community beach front, and much more – providing a premium vacation experience to all community members. Embrace Lakefront Living at its Best. As for some features of the home: 1. New Roof (2022) 2. Rebuilt chimney (2020) (see photo of top) 3. New Shed (2021) 4. New Front deck (2021), new back deck (2018) 5. New basement bathroom (2026) 6. New driveway on side of house (2021) can fit up to 6 cars 7. Stripped and shined bluestone basement level (2026)

74 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

$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

$115,000

1021388 MLS

This gorgeous stream-front lot is located just inside the main gate of The Chapin Estate. The lot borders 448 feet of Black Lake Creek which feeds into the 900+/- acre Toronto Reservoir. The Toronto Reservoir is known for its fishing, kayaking, paddle boarding, water skiing and swimming. Gasoline engines are permitted with a 20' maximum vessel length, and you have access nearby on Moscoe Road. This is a 4 season, gated, residential community that consists of 2500 acres of preserved lands that border 1750 acres of freshwater lakes. This prestigious community is known for its luxury vacation homes and its close proximity to NYC. The member's only Lake Club within the gates is optional for this particular homesite. Access to Swinging Bridge is also available within the community. As a resident, you may also rent a slip at the Lake Club to grant you access to both reservoirs. *Short term rentals are not permitted. Rental minimum of 3 months no more than twice per year. Confirmed appointment for the security of our residents.

TBD Chapin Trail, White Lake

$479,000

3 Beds ⋅ 3 Baths ⋅ 987303 MLS

Crisp mountain air, pristine lakes, spacious pools, and numerous activities await you at Emerald Green in the Sullivan County Catskills. Welcome home to 20 Bristol Circle, a charming colonial situated on a serene and spacious lot. The house is move-in ready and offers central heating and air conditioning, three bedrooms, two and a half bathrooms, a finished basement, and a two-car garage. Enjoy your morning coffee on the covered front porch, on the massive back deck, or in the Zen garden in the backyard. This house is situated on one of the nicest lots in Emerald Green, come see it today! Upon entering the foyer, you are greeted by double height ceilings and an airy interior. The first floor features a large, eat-in kitchen with ample cabinet space, an island breakfast bar, and a pantry closet. A slider in the kitchen leads to a massive deck which faces the woods, the perfect spot for grilling or entertaining. There is a formal dining room, a spacious living room with a propane fireplace, and a bonus den/family room that can be used as a home office or first floor guest room. This level has a half bathroom and coat closet in the foyer. The second floor has a spacious landing with a linen closet, a full bathroom with a bathtub, and three good-sized bedrooms. The primary bedroom is massive and offers cathedral ceilings, a walk-in closet, and an over-sized bathroom with a jacuzzi tub, walk-in shower, and double vanity. The finished basement offers another large and flexible space, which could be used as a playroom or home office, and it has a laundry area as well. The over-sized two-car garage can accommodate two large vehicles, as well as plenty of storage. It’s hard not to fall in love with the peaceful setting upon which the house is located. The front and rear yards are beautifully landscaped and offer plenty of space to enjoy. There are no houses behind this one, so the woods create a tranquil oasis with vibrant wildlife. There is a serene Zen garden in the backyard, a little slice of Catskill mountain paradise. The house is located right near the Entertanium, outdoor sports courts, dog run, and clubhouse. Emerald Green is Sullivan County’s premier private community. It offers two brand new pools that are located at the lakeside sand beach. There are three lakes for boating (non-gas boats only) fishing, and swimming. Boat slips are available for rent. There are also communal playgrounds, basketball courts, tennis courts, pickleball courts, a dog run, and an indoor clubhouse with a gym. Emerald Green offers community events such as holiday celebrations, seasonal fireworks, activities for all ages, exercise classes, game nights, etc. It is the perfect way to experience the quiet of country living in a friendly and serene neighborhood setting. This property offers the benefits of municipal water and sewer, as well as road maintenance and snowplowing provided by the town. Rock Hill is the perfect place for a country getaway or full-time home. With its small-town charm, convenient shopping options and proximity to the city, this is the place to be in Sullivan County!

20 Bristol Circle, Rock Hill

$584,999

3 Beds ⋅ 2 Baths ⋅ 986218 MLS

Beautiful Renovated Lake House with Prime Lakefront Location on Treasure Lake & Community Amenities located in Emerald Green. This is great for all year round living or for your weekend gateway! Enjoy the areas amenities such as Resort's Casino, Water Park, Monster golf course Restaurants and many local breweries and fishing lakes and even skiing for the winter! Experience lakeside living at its finest in this beautifully renovated lake house, perfectly situated on serene lake frontage. This charming home offers a modern, updated interior done in 2025 with spacious living areas, stylish finishes, and breathtaking waterfront views. Enjoy direct access to the lake for swimming, kayaking, or fishing right from your backyard. The community features a range of amenities, including a private dock, swimming pool, clubhouse, walking trails, and recreational areas—ideal for relaxing weekends or active outdoor lifestyles. There wasn't a room that hasn't been touched in this home. The basement is fully finished and ready to entertain guests. Whether you're seeking a peaceful retreat or a fun-filled getaway, this lake house combines comfort, convenience, and natural beauty in a sought-after community setting.

119 Lake Shore Drive W, Rock Hill

$3,475,000

5 Beds ⋅ 6 Baths ⋅ 967444 MLS

A mere two hours from New York City, The Top Ridge Retreat offers a rare combination of modern elegance, natural beauty, and complete privacy within the exclusive 2,500-acre gated community of The Chapin Estate. Set on more than eleven acres, this contemporary residence delivers a refined lifestyle designed for comfort, sophistication, and seamless indoor-outdoor living. Inside, the layout balances openness with intimacy. The home is offered fully furnished, with carefully curated furniture and artwork included to complement its contemporary design and elevate the overall living experience. The primary suite includes a private sitting area, fireplace, and spa-like bath, creating a true sanctuary. Additional bedrooms are spacious and well-appointed for guests. A sunken living room and library—each with a fireplace—add warmth and architectural interest, while a dedicated gym, massage room, and wellness area enhance the home’s retreat-like atmosphere. Every element of the home has been thoughtfully crafted. With 205 oversized windows, natural light fills each space and creates a continuous connection to the surrounding forest. The expansive chef’s kitchen and dining room overlook the saltwater Gunite pool, pool house, and a fully equipped indoor/outdoor kitchen featuring a fireplace, pizza oven, and dining gazebo—an ideal setting for effortless entertaining. A short stroll from the pool leads to a world-class tennis court with its own cabana, offering resort-level recreation right at home. The residence is built with uncompromising attention to quality. Features include a 12-zone radiant and solar heating system, a 12-ton central air conditioning system, custom cabinetry, and bespoke tile work throughout. From the solid wood doors to the precision-crafted finishes, every detail reflects a commitment to excellence. Life within The Chapin Estate offers unmatched access to nature and amenities. The community spans more than 2,500 acres of pristine forest and borders an additional 14,000 acres of protected conservation land. Residents enjoy miles of hiking, biking, and snowshoe trails; freshwater reservoirs and trout streams; concierge services; security patrols; and a members-only Lake Club. From within the community, owners have direct access to both Toronto Reservoir and Swinging Bridge Reservoir, ideal for boating, kayaking, fishing, and quiet days on the water. Just one mile away, the Chatwal Lodge provides elevated dining and hospitality. Located in the hamlet of White Lake, part of historic Bethel—home of the 1969 Woodstock concert—this region is rich with culture and recreation. The Bethel Woods Center for the Arts offers world-class performances and a renowned museum. Nearby, the Monticello Motor Club provides a premier private automotive experience. Farm-to-table dining, boutique cafés, craft breweries, lake activities, skiing, and endless outdoor adventures complete the lifestyle. A true escape from city life, The Top Ridge Retreat delivers privacy, beauty, and resort-style amenities in one of Sullivan County’s most coveted luxury communities. This is contemporary living at its finest—without the stress of the Long Island Expressway.

61 Top Ridge Trail, White Lake

$115,000

966241 MLS

Here is surely the best opportunity to build your dream home on 5.26 private acres within the elegant sanctuary of Chapin Estates — a premier gated residential preserve celebrated for some of the East Coast’s most breathtaking natural beauty. Residents enjoy exceptional amenities, including a private lake club, sparkling lakes, trout streams, fishing, and miles of scenic hiking trails. Imagine yourself surrounded by distinguished estates valued from $1 million to over $10 million. This property offers an exclusive lifestyle in a peaceful yet convenient location. The Chatwal Lodge is also located within the community, adding an extraordinary touch of hospitality close to home. Not sure where to begin? This engineered lot is offered with custom house plans designed by Chapin Estates founder Steve Dubrovsky. For $844,900, Steve and his team are prepared to build the lodge depicted in the plans, creating a seamless path from vision to completion. Call today for more details and experience the luxury and serenity of living at The Chapin Estate.

Lot 32 Woodstone Trail, Bethel

$949,900

3 Beds ⋅ 3 Baths ⋅ 954068 MLS

*New Construction Let us bring your vision to life—your home, your way. Nestled within the prestigious Swinging Bridge section of Chapin Estates, this exceptional property offers a rare blend of rustic elegance and refined luxury. Located just two hours from New York City and minutes from Bethel Woods Center for the Arts, Resorts World Catskills, the Kartrite Indoor Waterpark and Award-winning golf courses, the homesite is ideally positioned for both serenity and adventure. The 5.28-acre parcel of ready-to-build land offers the perfect canvas for your dream home. A beautiful rock-lined driveway has already been cut in, welcoming you to your future retreat. We proudly offer the construction of a beautifully designed three-bedroom, two and a half -bath residence, tailored to meet your lifestyle and preferences. Whether you choose a fully custom design tailored to your vision or select from our curated collection of beautiful layouts. Each home reflects quality craftsmanship and timeless style, designed to harmonize with the natural surroundings and community aesthetic. Please note: All building plans must be approved by The Chapin Estates Association and must adhere to the community’s architectural guidelines. Images featured are sourced from America's Best House Plans and are used for inspiration purposes only. Residents and guests enjoy year-round access to the renowned Chatwal Lodge, a five-star wilderness retreat offering farm-to-table dining, spa and wellness experiences, and curated outdoor activities like fly fishing, boating, and guided nature walks. The community features private lake access, a members-only marina and clubhouse, and gated security for peace of mind. Recreational amenities include a swimming pool, tennis courts, pickleball and basketball courts, and miles of scenic walking trails. All walking distance from the property. Whether you're seeking a weekend escape or a full-time residence, this property delivers an unparalleled lifestyle defined by luxury, privacy, and natural beauty. On your way, enjoy a stop at Woodbury Commons for some great shopping or LEGOLAND New York and spend more quality time with the family. With its prime location, four-season appeal, and access to world-class amenities, this is more than a property—it’s a legacy in the making.

39 Woodstone Trail, Bethel

$150,000

951393 MLS

This beautifully wooded and pastured lot is just within the main gates of The Chapin Estate. Just over 5 acres with 584' of stream frontage on Black Lake Creek. Homesite must be 50' from property line. This site requires a septic system, drilled well and underground electric to homesite. This is an approved building lot with electric and cable at road. Driveway cut was made to the most desirable home site. The lot borders Black Lake Creek which feeds into the 900+/- acre Toronto Reservoir. The Toronto Reservoir is known for its fishing, kayaking, paddle boarding, water skiing and swimming. Gasoline engines are permitted with a 20' maximum vessel length. This is a 4 season, gated, residential community that consists of 2500 acres of preserved lands that border 2000 acres of freshwater lakes. This prestigious community is known for its luxury vacation homes and its close proximity to NYC. The member's only Lake Club within the gates is optional or this particular homesite. The Chatwal Lodge is a luxury boutique hotel located a mile from this property within the gates of The Chapin Estate. The hotel is open for business and amenities to be offered to residents in the future. Floor plans for a 4-bedroom New England Style home are included with the purchase of this lot. *Short term rentals are not permitted. Rental minimum of 3 months no more than twice per year. **All appointments requests need 24 Hour notice; the HOA does not permit drive up showings or grant access through the gates without a confirmed appointment for the security of our residents. Owner Financing is Available.

Lot 4 Chapin Trail, Bethel

$64,999

2 Beds ⋅ 2 Baths ⋅ 944437 MLS

Welcome to a fantastic opportunity in the sought-after Kinnebrook Community. This 2-bedroom, 1.5-bath home is priced to sell! The home features a functional layout awaiting your personal touch. Enjoy a hassle-free lifestyle with community-provided water, septic, snow, and trash removal, as well as fantastic amenities including an in-ground pool and a dog park. With low lot rent and a motivated seller, this property, sold AS-IS, won't last long. Schedule your showing today!

25 Pansy Lane, Monticello

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