Sullivan Homes with Maintenance Amenities

Welcome to Sullivan County, New York—a hidden gem nestled in the picturesque Catskill Mountains. Known for its stunning landscapes, vibrant communities, and rich history, Sullivan County offers a unique blend of rural charm and modern conveniences. Whether you're drawn to the tranquil lakes, scenic hiking trails, or the lively towns filled with local shops and restaurants, this region has something for everyone.

Sullivan County is renowned for its outdoor recreational opportunities. With over 1,000 lakes and ponds, it’s a paradise for fishing, boating, and swimming enthusiasts. The surrounding mountains provide endless trails for hiking, biking, and winter sports, making it an ideal destination for nature lovers year-round. The county is also home to charming towns like Bethel and Monticello, where you can experience local culture, art, and cuisine.

For those considering making Sullivan County their home, you’ll find a variety of properties that come with maintenance amenities, ensuring a hassle-free living experience. Many homes in the area offer features such as landscaping services, snow removal, and community upkeep, allowing you to enjoy the beauty of your surroundings without the burden of maintenance. This is perfect for busy professionals or retirees looking to savor the serene lifestyle that Sullivan County has to offer.

With its combination of natural beauty, vibrant community spirit, and convenient amenities, Sullivan County is more than just a place to live—it's a place to thrive. Come discover your dream home in this enchanting region, where every day feels like a getaway!

Newest Sullivan Homes with Maintenance Amenities

$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

$389,000

2 Beds ⋅ 3 Baths ⋅ 1020730 MLS

Welcome to 2 Sylvia Lane, a spacious 3-bedroom, 3-bathroom duplex home located in the desirable Greentree Community of Monticello. This well-maintained property offers comfort, convenience, and low-maintenance living. Enjoy parking right in front of the home, a short walk to the community clubhouse, and easy access to Resorts World Casino, Kartrite Waterpark, and local shopping. The HOA takes care of snow removal, garbage, exterior painting, and even roof replacement, making homeownership simple and worry-free. Community amenities include a pool, clubhouse, and serene lake access perfect for kayaking. Priced to sell and ready for summer enjoyment

2 Sylvia Lane, Monticello

$949,000

4 Beds ⋅ 3 Baths ⋅ 1016931 MLS

Welcome to Kenoza Hollow, a serene and stylish haven sited privately within the gated community of Kenoza Lake Estates. This newly constructed home offers a peaceful sanctuary nestled among mature trees, just a minutes from your deeded lake access. Vaulted ceilings and expansive picture windows flood the home with natural light, giving the space a warm glow even on grey days. Thoughtful architectural details like the rich wooden accent wall anchoring the dining area and the custom stone patio outdoors lend the home an air of understated sophistication. The kitchen is a chef’s dream, with ample warm wood cabinetry, a convenient center island for meal prep and casual dining and stainless steel appliances. Conveniently adjacent, the spacious dining area is anchored by a statement light fixture, and built in cabinetry with slatted wood detail. Large picture windows and sliding glass doors frame the main living room, making the surrounding natural landscape a constant focal point. A sleek, modern wood provides warmth and character. Just outside, a beautiful fieldstone terrace provides a seamless transition into nature and acts as the backdrop for outdoor entertaining. The primary suite is anchored by an oversized picture window and boasts a spa-like en-suite bath complete with a custom tiled shower, vaulted ceilings, and a deep soaking tub. The remaining three bedrooms are equally inviting, each offering high ceilings, lovely views, and abundant natural light. Two additional stylish full bathrooms and a dedicated laundry room complete the main level. The lower level unfinished walk-out basement offers a blank canvas with room to grow. Full windows and glass doors keep this lower level bright and versatile, ready for your vision. Living in Kenoza Lake Estates grants you access to a private, sandy community beach and dock, perfect for waterside relaxation or as a launching for water sports. While the development is walkable, the beach also includes convenient parking for days when you're hauling extra gear. Beyond the gates, you are surrounded by the best of the Western Catskills. Bethel Woods Center for the Arts offers a world-class music venue and cultural hub located on the original site of the 1969 Woodstock festival. Kenoza Hall sits just across the lake and features fine dining and a luxury spa. The charming hamlet of Jeffersonville offers a variety of shopping and dining opportunities as well as a great staple grocery store and weekly farmer’s market.

53 Land and Lakes Trail, Kenoza Lake

$499,990

2 Beds ⋅ 2 Baths ⋅ 999731 MLS

Set directly on the shores of Treasure Lake within the highly sought-after Emerald Green community, this beautifully reimagined waterfront retreat offers approximately 100 feet of lake frontage and breathtaking sunset views looking west across the water. Nestled within a premier 1,400-acre private community featuring Lake Louise Marie, Treasure Lake, and Davis Lake, residents enjoy access to over 250 acres of water ideal for swimming, fishing, kayaking, paddleboarding, and electric boating. Completely renovated down to the studs, this move-in-ready home was thoughtfully designed to capture its incredible lakefront setting. The open-concept main living area is highlighted by dramatic floor-to-ceiling windows that flood the home with natural light while showcasing panoramic lake views from nearly every angle. A wood-burning fireplace adds warmth and charm, while sliding glass doors lead to an expansive deck and screened-in porch — the perfect places to relax and take in the spectacular evening sunsets over Treasure Lake. The updated kitchen features stone countertops and stainless steel appliances, seamlessly connecting to the dining and living spaces for effortless entertaining. The home offers two generously sized bedrooms, including a private primary suite with its own full bath, plus an additional full bathroom and convenient laundry area. Individual heating zones throughout the home provide comfort and efficiency, complemented by a newer ductless heating and cooling system. Beneath the home, a spacious crawlspace offers ideal storage for kayaks, paddleboards, floats, life jackets, and all your waterfront gear. Outside, the level backyard leads directly to the lake and creates the ultimate outdoor setting with a private dock, sandy beach area, firepit, and endless opportunities to enjoy the waterfront lifestyle. Emerald Green residents enjoy an impressive collection of amenities including indoor and outdoor pools, fitness center, indoor walking track, tennis and pickleball courts, basketball courts, dog park, clubhouse, sandy beach, and a vibrant social calendar featuring live entertainment, community gatherings, fitness classes, fireworks, and more. Conveniently located near destinations like Bethel Woods Center for the Arts, Resorts World Catskills, and The Kartrite Resort & Indoor Waterpark, along with skiing, hiking trails, wineries, and countless outdoor attractions, this is a rare opportunity to own a fully updated lakefront home with stunning western sunset exposure in one of the region’s most desirable private lake communities.

117 Lake Shore Drive W, Rock Hill

$129,000

1002465 MLS

5.25-acre homesite in The Highlands, one of Bethel’s most private and architecturally distinctive communities. Set deep within a gated enclave of thoughtfully designed modern homes, this wooded parcel offers an exceptional opportunity to create a private retreat surrounded by nature, quiet, and strong contemporary design. The lot is fully wooded, highly buildable, and positioned to allow for a home with remarkable privacy and separation from neighboring properties. Rolling topography and mature trees create a natural setting that feels secluded without being remote from the area’s key destinations. The Highlands has evolved into a sought-after community where architecture and landscape work together intentionally. Buried utilities, underground electric, and broadband infrastructure preserve the natural character of the setting while supporting modern living. Whether envisioning a modern cabin, minimalist retreat, or full-time residence immersed in nature, the setting supports a sophisticated residential vision. Located minutes from Bethel Woods Center for the Arts, area lakes, hiking trails, waterfront dining, Resorts World Catskills, and the growing design and hospitality scene throughout Sullivan County. A rare opportunity to build within one of Bethel’s most compelling private communities.

Lot 5 Timber Drive, Bethel

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 989403 MLS

Anchored gracefully along four hundred feet of shoreline on the Peninsula at the Chapin Estate, Whispering Oak Landing is a country retreat like no other. This custom-built legacy lakefront home constructed by the current owner, is nestled beneath majestic oaks and surrounded by five enchanting acres of untouched woodland. Discretely tucked within an exclusive 2,500-acre gated wilderness preserve, the property offers the perfect blend of privacy and security, just two hours from Manhattan and fifteen minutes from the new Sullivan County International Airport. Once inside, a vaulted foyer crowned by a crystal chandelier opens to expansive, sunlit gathering spaces. Adjacent to the front entrance, a convenient powder room sits across from a bright, oversized laundry room with a utility sink, exterior door, and interior access to the two-car garage. The main level is composed of a warm and inviting living room with a classic wood-burning fireplace, a professionally appointed kitchen with dual sinks, and seamless indoor-outdoor dining areas complete with a built-in grill. The vaulted, east-facing primary suite, a standout feature, is also located on this level for effortless single-floor living, and features tranquil wooded lake views from an oversized picture window. The en-suite bath is a sanctuary of indulgence, complete with a windowed soaking tub, dual vanities, walk-in shower, and refined finishes. A stately walk-in closet, discreetly accessed from the private hallway, completes this restful retreat with both elegance and practicality. Upstairs, two well-proportioned bedrooms are positioned at either end of the home and connected by an open corridor with railings that overlook the main living area below. A naturally lit shared bathroom serves both rooms. One bedroom features a charming Juliette balcony, while the other includes a spacious, unfinished dormer room above the garage, offering excellent potential for future expansion. Downstairs, the lower level provides a cozy and versatile relaxation space, including a fourth full bedroom and an additional room ideal for fitness, a reading lounge, or a fifth bedroom. Designed with comfort and entertainment in mind, this level is also outfitted with a full wet bar, a cedar sauna, full bath, and an expansive secondary living room that opens to a graceful flagstone terrace, perfect for indoor-outdoor relaxation. Architectural highlights include soaring ceilings with exposed pine beams, wide-plank hardwood floors, granite countertops, and central air conditioning, thoughtfully designed to enhance a true year-round living experience. Sunlight pours into the home from dawn to dusk, creating an inviting atmosphere throughout the day. Additional practical features such as insulated windows and a central alarm system ensure ease of ownership and lasting peace of mind. Surrounding the home, the Chapin Estate spans 2,500 acres of pristine forest and borders 14,000 acres of protected conservation land. Community amenities include 2,000 acres of freshwater reservoirs and trout streams, and over nine miles of hiking and riding trails. With panoramic views of the 900 acre Toronto Reservoir and its untouched wilderness borders, the home is perfectly positioned for serene mornings on the water and adventurous days of boating, swimming, and paddling. Enjoy close proximity to the Eldred Preserve, an upscale boutique hotel featuring the Homestead Restaurant, a local farm to table dining experience. Minutes from the Bethel Woods Center for the Arts and the Monticello Motor Club, Whispering Oak Landing offers a rare lifestyle of timeless design, seamless connection to nature, and effortless access to the best of the Catskills, one that few will ever experience, and even fewer will be fortunate enough to call home.

51 Homestead Trail, White Lake

$750,000

4 Beds ⋅ 2 Baths ⋅ 983942 MLS

Experience lakefront living at its finest in this beautifully maintained 4 bedroom, 2 bath contemporary lakefronthome located in a premier 1,400 acre community featuring three private lakes, Lake Louise Marie, Treasure Lake, and Davis Lake, with more than 250 acres of pristine water for swimming, fishing, and electric boating. Designed to showcase breathtaking lake views, the main level features soaring cathedral ceilings and dramatic floor to ceiling windows and glass sliders that flood the home with natural light while providing panoramic waterfront views from the living room, dining area, and kitchen. The spacious living room is anchored by a stunning floor to ceiling stone fireplace with a ceramic sterno insert and accented by skylights and an elegant Murano glass chandelier. Hardwood floors and central air complete the home’s comfortable and inviting interior. The kitchen features a convenient serving bar that opens seamlessly to the dining area, creating an ideal space for entertaining. Glass sliders lead to an expansive full length Trex deck with two electric awnings, providing the perfect setting for outdoor dining, relaxing, and taking in spectacular sunsets over the lake. The main level includes a spacious primary bedroom, a second bedroom, and a beautifully renovated full bath with tasteful designer finishes. The finished walkout lower level offers a large family room, two additional bedrooms, a full bath, and a utility room, providing flexible space for guests, extended family, or recreation. Outside, enjoy your own private waterfront retreat featuring a professionally landscaped lawn, illuminated cobblestone walkway, an oversized Trex deck, private sandy beach, gazebo, and private dock, ideal for a pontoon boat, kayaking, paddleboarding, fishing, or simply enjoying life on the water. A horseshoe driveway accommodates 6 to 8 vehicles, while the home’s attractive wood and cultured stone exterior adds timeless curb appeal. Residents enjoy an outstanding array of resort style amenities including an Olympic size adult pool with lap lanes and a current walking lane, a children’s pool with splash features, sandy beaches, a fitness center, tennis and pickleball courts, basketball courts, playgrounds, a dog park, and year round social activities including yoga, aqua aerobics, book clubs, potlucks, and live entertainment. Conveniently located just minutes from Bethel Woods Center for the Arts, Resorts World Catskills, The Kartrite Resort and Indoor Waterpark, Holiday Mountain Ski and Fun Park, local wineries, scenic hiking trails, farmers markets, and countless outdoor recreational opportunities, this exceptional lakefront home offers the perfect combination of luxury, comfort, privacy, and an unmatched four season lifestyle.

44 Lake Shore Drive S, Rock Hill

$125,000

2 Beds ⋅ 2 Baths ⋅ 983936 MLS

Affordable Seasonal House Located in a Private Lake Community! Welcome to 1192 Route 52, a move-in ready seasonal co-op located in the Loch Sheldrake Beach & Tennis Club, a small and friendly lakeside summer retreat. The community is typically open from mid-April through mid-October and offers members an in-ground swimming pool, lake access with a sandy beach, tennis court, volleyball, playground, and other exciting amenities. Enjoy laid-back lake living in a friendly community where reasonable annual dues include parking, trash, water, sewer, electric, propane, and common area maintenance. Co-op board approval is required and only cash purchases are permitted. Rentals are not allowed. The house, originally two separate units, has been combined into a spacious two-bedroom, two-bathroom with a great floorplan. High ceilings with knotty pine shiplap, exposed wooden beams, and hardwood flooring give off serious lake cabin vibes. The kitchen features newer stainless-steel appliances, there is a dining area and two living rooms. Both bedrooms are spacious, one has an en-suite bathroom and the other has a private deck with views of the lake. On the outside, a large deck offers sweeping views of sparkling Loch Sheldrake and plenty of space to BBQ, relax, and entertain. The house is being sold fully furnished for a completely turn-key sale. The community is conveniently located in the middle of Sullivan County, close to golf courses, Resorts World Catskills, & the Kartrite Indoor Waterpark. The nearby town of Liberty offers a Shoprite, Tractor Supply, and a delicious variety of restaurants. Nearby parks include Morningside Park, Hanofee Park, & Walnut Mountain. This is the place to be for easy and affordable summer living, come see it today!

1192 State Route 52 Unit #21, Loch Sheldrake

$429,000

2 Beds ⋅ 2 Baths ⋅ 979575 MLS

Some homes are where you live. Others are where you finally exhale. Set along the peaceful shoreline of Forestburgh Pond, this two-bedroom, two-bathroom waterfront cabin offers something that's becoming increasingly difficult to find: privacy, water access, and a slower pace of life just 90 minutes from New York City. Whether you're searching for a full-time residence, a weekend retreat, or a property with short-term rental potential, this home is designed to make every season feel like a getaway. The open living space welcomes you with vaulted ceilings, a floor-to-ceiling stone fireplace, warm hardwood floors, and oversized windows that keep the water in view. The kitchen blends style and function with quartz countertops, stainless steel appliances, open shelving, and a cozy dining area overlooking the pond. The primary bedroom features its own updated en suite bathroom with a walk-in shower, while the second bedroom and additional full bath provide comfortable space for guests. Outside is where this property truly shines. Launch a kayak from your own shoreline, spend the afternoon fishing or canoeing, unwind around the fire pit beneath the stars, or simply enjoy the peaceful views from the wraparound deck. Every part of the property invites you to slow down and enjoy the setting. Beyond the water, you'll appreciate being just minutes from local favorites including the Forestburgh Tavern, Forestburgh Playhouse, scenic walking trails, Bethel Woods Center for the Arts, and charming local shops. It's a location that feels tucked away while still keeping some of Sullivan County's best destinations close by. If you've been waiting for a waterfront property that offers both everyday comfort and the kind of lifestyle people travel to experience, this is one worth seeing.

10 Stag Forest Road, Forestburgh

$494,900

4 Beds ⋅ 3 Baths ⋅ 966768 MLS

Lake life awaits you! Welcome to this beautiful 4 bedroom, 2.5 bath Colonial home constructed within the last five years. Emerald Green is a 1,400 acre private community with three pristine lakes hidden away in New York’s legendary Sullivan County Catskills. Enjoy 55 common acres and a variety of amenities, including swimming, tennis, boating, an exercise room, and an array of recreational events. Including hardwood floors throughout and a generous 2 car garage, this home offers the peace of mind that comes with newer construction; modern systems, energy efficiency, and appliances that are all just a few years old. The classic Colonial layout with a bonus first floor flex-room provides the perfect blend of functionality and flow, with generous living spaces, a bright kitchen ready for gatherings, and four well-proportioned carpeted bedrooms upstairs including a spacious primary suite with an oversized walk-in closet. Move-in ready from day one, this home also offers room to personalize and add your own finishing touches over time. An ideal opportunity to build equity while creating a space that truly reflects your style. The unfinished walk-out basement offers excellent storage and future potential living space. Residents enjoy resort-style amenities including private lake access, a heated swimming pool, clubhouse, fitness center, pickleball courts and more. Whether you're kayaking on the lake, spending summer afternoons poolside, or hosting events at the clubhouse, the lifestyle here is unmatched. Excellent management and a healthy reserve fund ensure things continue running smoothly. A newer home, community amenities, and the chance to make it your own, this is Rock Hill living at its best! Just in time to enjoy all the summer fun at the lake! The 4th of July celebration is not to be missed.

62 Bristol Circle, Rock Hill

$625,000

903335 MLS

This stunning home site, adjacent to Lot 1, consists of lush forests full of evergreens and hardwoods. However, the change in elevation allows for 2 home sites. The first site is close to the 413’ of Lake Frontage that is facing north to the mountains and surrounded by mature trees. The second site, much higher, allows for longer views with a gravel driveway to the water below. An old carriage trail runs along the shoreline here and there is a high cliff on one end of the lot and a more gradual access on the other for access to Swinging Bridge Reservoir. Located at the Chapin Estate, a 4-season gated residential preserve on 2500 acres of pristine forest lands bordering 14,000 acres of forever wild conservation properties. Unique attributes include: 1,750 acres of fresh water lakes and trout streams; 9+ miles of hiking, biking and snow shoe trails; Members only Lake Club; Security patrolled and Concierge Services. Also located within our gates is The Chatwal Lodge - a wonderful amenity for the residents and guests. Book a weekend to see what the Chapin lifestyle has to offer. Conveniently located less than 2 hours from Mid-Town Manhattan and even less from North Jersey. Bring your own builder or use on of the recommended craftsmen from our area. Nestled in the heart of the Catskills, Sullivan County offers a rare blend of natural grandeur and cultural sophistication. Known for its pristine lakes, protected forests, and sweeping mountain vistas, the region is a sanctuary for those seeking tranquility without sacrificing access to world-class amenities. From the storied banks of the Delaware River to the exclusive enclaves of The Chapin Estate, Sullivan County is home to some of New York’s most coveted private retreats. Residents enjoy four-season recreation—kayaking, hiking, fly fishing, and snowshoeing—alongside curated experiences like concerts at Bethel Woods Center for the Arts, farm-to-table dining, and boutique shopping in towns like Narrowsburg and Callicoon. With its proximity to Manhattan and North Jersey, Sullivan County offers effortless escape and enduring value. Whether you're seeking a legacy estate, a waterfront haven, or a modern mountain lodge, this region invites you to live beautifully, surrounded by nature and steeped in possibility. Located at Captivating lake front view at the Chapin Estate, Lumberland, New York 12737, this Land is for Sale with a price of $625,000. This listing encompasses a lot of 5.65 Acre(s). See all Homes for Sale in Lumberland.

Lot 2 Woodstone Trail, Lumberland

$600,000

903323 MLS

This gorgeous home site has a most dramatic elevation change on over 5+ acres with build site facing the northern mountain range. This lot consists of lush forests full of evergreens and hardwoods. The improved gravel driveway leads to the elevated home site and then to 336’ of frontage on the shores of the Swinging Bridge Reservoir. The opposite shoreline has building restrictions which limit the private residents to building 300' from their shoreline. This essentially offers forever wild views from this property and it's shoreline. Also located within our gates is The Chatwal Lodge - a wonderful amenity for the residents and guests. Book a weekend to see what the Chapin lifestyle has to offer. Located at the Chapin Estate, a 4-season gated residential preserve on 2500 acres of pristine forest lands bordering 14,000 acres of forever wild conservation properties. Unique attributes include: 1,750 acres of fresh water lakes and trout streams, 9+ miles of hiking, biking and snow shoe 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. Building your dream home: bring your own builder or use a reputable builder that is familiar with the guidelines in the community. The area: Nestled in the heart of the Catskills, Sullivan County offers a rare blend of natural grandeur and cultural sophistication. Known for its pristine lakes, protected forests, and sweeping mountain vistas, the region is a sanctuary for those seeking tranquility without sacrificing access to world-class amenities. From the storied banks of the Delaware River to the exclusive enclaves of The Chapin Estate, Sullivan County is home to some of New York’s most coveted private retreats. Residents enjoy four-season recreation—kayaking, hiking, fly fishing, and snowshoeing—alongside curated experiences like concerts at Bethel Woods Center for the Arts, farm-to-table dining, and boutique shopping in towns like Narrowsburg and Callicoon. With its proximity to Manhattan and North Jersey, Sullivan County offers effortless escape and enduring value. Whether you're seeking a legacy estate, a waterfront haven, or a modern mountain lodge, this region invites you to live beautifully, surrounded by nature and steeped in possibility. Located at Homesite With Forever Wild Views at The Chapin Estate, Lumberland, New York 12737, this Land is for Sale with a price of $600,000. This listing encompasses a lot of 5.67 Acre(s). See all Homes for Sale in Lumberland.

Lot 1 Woodstone Trail, Lumberland

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