Sullivan Homes with Oversized Parking features

Welcome to Sullivan County, New York, a hidden gem nestled in the picturesque Catskills, where natural beauty meets a vibrant community spirit. Known for its stunning landscapes, Sullivan County offers a perfect blend of outdoor adventure and serene living, making it an ideal place for families, retirees, and everyone in between. With its rich history, charming small towns, and an abundance of recreational activities, Sullivan County invites you to embrace a lifestyle that celebrates both tranquility and excitement.

One of the standout features of homes in this enchanting county is the availability of oversized parking options. Imagine having ample space for your vehicles, RVs, or even a boat, all within the comfort of your own property. This feature is particularly appealing for those who enjoy outdoor activities, as Sullivan County is renowned for its hiking trails, fishing spots, and lakeside retreats. Whether you’re heading out for a weekend getaway or simply need extra space for guests, oversized parking ensures that your home is as functional as it is beautiful.

In Sullivan County, you can find a diverse range of homes equipped with these convenient parking features, allowing you to live your best life without the hassle of limited space. From cozy cabins to spacious family homes, each property offers a unique charm that reflects the area's rich heritage and natural surroundings. Discover the perfect home in Sullivan County, where oversized parking meets the tranquility of country living, and let your new adventure begin!

Newest Sullivan Homes with Oversized Parking features

$950,000

2 Beds ⋅ 2 Baths ⋅ 1030470 MLS

We are proud to present this exceptional Catskills retreat, offering over 61 breathtaking acres of pristine countryside. A rare opportunity to own your own private paradise, this remarkable property combines panoramic views, rolling fields, mature woodlands, and outstanding privacy in one extraordinary setting. A long private driveway winds through the property, leading to the home and creating a peaceful, secluded escape. The picturesque fields are currently maintained by a local farmer, helping to keep property taxes low while preserving the land’s natural beauty. The property is thoughtfully equipped with everything needed for country living. A spacious detached garage features two oversized vehicle bays along with a dedicated gym and recreation area. An additional barn offers endless possibilities, whether you envision expanded storage, a workshop, hobby space, or conversion into additional living quarters. Inside, the home welcomes you with a bright, open-concept floor plan filled with natural light. The spacious main level is ideal for everyday living and entertaining, featuring generous gathering spaces and a well-designed kitchen. Upstairs, you’ll find two comfortable bedrooms including a primary suite with a private en-suite bath. The flexible layout also provides the opportunity to easily create a third bedroom on the first floor. Whether you’re looking for a full-time residence, weekend getaway, equestrian property, hobby farm, or private recreational retreat, this exceptional property offers endless possibilities. Conveniently located just minutes from the charming hamlets of Callicoon, Roscoe, Livingston Manor, and Jeffersonville, you’ll enjoy easy access to award-winning restaurants, breweries, boutique shopping, farmers markets, outdoor recreation, and all that the Catskills has to offer.

174 Bayer Road, North Branch

$460,000

3 Beds ⋅ 2 Baths ⋅ 1027722 MLS

Opportunity Knocks in the Heart of the Catskills! Discover an exceptional opportunity in the charming hamlet of Jeffersonville, New York, where location, lifestyle, and investment potential come together on one remarkable property. This beautifully maintained 3-bedroom, 2-full-bath split-level home offers comfortable living with room to grow, all nestled along the banks of the famed Callicoon Creek. Step inside to find a warm and inviting layout, complemented by a fully finished lower level perfect for a family room, home office, recreation space, or guest quarters. Outside, a spacious deck overlooks an expansive backyard that gently stretches to over 100 feet of pristine Callicoon Creek frontage. Imagine relaxing by the water's edge, casting a fishing line, cooling off with a refreshing splash, or simply enjoying the peaceful sounds of one of Sullivan County's most treasured waterways. Multiple sitting areas along the creek create your own private outdoor retreat. Adding even more value is a separate two-car garage situated on its own deed, offering an extraordinary opportunity. With two separate deeds, the garage parcel is buildable for an additional residence (subject to municipal approvals), making this a rare offering for homeowners, investors, developers, or those seeking a multigenerational compound. Perfectly located, you're just a short stroll to the quaint shops, restaurants, and cafés of downtown Jeffersonville, while world-class entertainment at the Bethel Woods Center for the Arts—the legendary site of the original Woodstock festival—is only minutes away. Whether you're searching for a full-time residence, weekend getaway, investment property, or a chance to build while enjoying an existing home, this unique offering delivers endless possibilities. Live in one. Build on the other. Invest in your future. Properties with this combination of creek frontage, separate buildable parcel, prime location, and limitless potential are incredibly rare. Don't miss this golden opportunity—schedule your private showing today before someone else answers the call!

5089 State Route 52, Jeffersonville

$895,000

4 Beds ⋅ 3 Baths ⋅ 1019802 MLS

This modern farmhouse has it all! Completely renovated down to the studs in 2026, this 4 BR/2.5 bath home has a place for everyone! It sits on 10.5 acres of former farmland/pasture. From the spacious, covered rocking-chair front porch, walk into the living area on the right and you'll see gorgeous gleaming wood floors and a woodstove. The brand new kitchen is fit for the most discriminating chef, with its shining quartz counters to the new stainless steel appliances. You'll never see so much cabinet space! Kitchen continues and melds seamlessly with the laundry area and a bathroom off that. Walk further in to the home and see the extra living area, whether you use it as a dining room (although the kitchen has enough space for a table!) or Family Room. You'll love the wood accents-- the floor and built-in storage. The primary bedroom is also on the main level, spacious with an ensuite full bath and closet space. Upstairs find 3 more bedrooms and a full modern bath with a lovely, inviting soaking tub. There's also a landing off the staircase that could be used as a sitting area, workout space, etc.. Navian On-demand hot water heater. And there are THREE barns and a gorgeous stone "milkhouse/ice house" that sit on this amazing property. Serious space for a collector, artist, hobbyist. The land is lush: think of the gardens you could have here! Terrific to start a small farm; everything is in place for you! The long-range views will keep you mesmerized for years! It's western-facing, and you'll be able to see every sunset, from the mundane to breath-taking! You're away from it all here on Henderson Road, tranquility awaits. But you're just 20 minutes to Roscoe or Callicoon for shopping, terrific eateries, Farmer's markets, banks, Bethel Woods, and river fun.

180 Henderson Road, Hankins

$420,000

3 Beds ⋅ 1 Baths ⋅ 1020034 MLS

Tucked on a peaceful, private 4-acre lot on a quiet, dead-end road with no neighbors in sight, this beautifully maintained colonial home offers both serenity and privacy, surrounded by nature. Inside, the home has been lovingly updated – on the main floor, a spacious living room invites you in with rich hardwood floors and the comforting glow of a wood-burning stove. There is a formal dining room and a bedroom on the first floor. The open kitchen is the true heart of the home – featuring an island, perfect for casual dining or entertaining and a bright, inviting eat-in area. The kitchen is a warm gathering spot where cooking and connection come together naturally. Upstairs there’s an additional living room/family room and two bedrooms with plenty of closet and storage space and a full bathroom. A dedicated laundry area with full-size washer/dryer and a work-out gym can be found downstairs. Outside, the level yard is a blend of lush lawn and mature trees – apple, pear and peach along with blueberry bushes – creating a peaceful orchard-like escape. There’s a detached 2-car garage plus a 1-car garage below, and a large shed, all ideal for both vehicles and storage. Just a short 15-minute drive to Callicoon or Roscoe, you’ll have easy access to shopping, dining, and endless outdoor adventures. This is your chance to embrace the beauty, tranquility and excitement of the Catskills!

10 Hoffman Road, Fremont Center

$469,000

3 Beds ⋅ 2 Baths ⋅ 1017024 MLS

Nestled on more than 5 private acres in beautiful Sullivan County, this move-in-ready home offers the perfect blend of comfort, space, and convenience. Known for its abundant outdoor recreation, Sullivan County provides endless opportunities for fishing, boating, hiking, and enjoying nature. The home features two first-floor bedrooms, including a spacious primary suite complete with its own fireplace and a luxurious en-suite bath featuring a soaking tub. Hardwood floors flow throughout the main living areas, while the oversized living room showcases a cozy wood-burning fireplace. A formal dining room and a full bathroom with double sinks add both functionality and charm. The well-appointed kitchen offers stainless steel appliances, a breakfast bar, a premium Viking range, and sliding glass doors leading to the fenced backyard and detached two-car garage. Upstairs, you'll find two additional rooms with newer carpeting, offering flexibility for guest rooms, home offices, or hobby spaces. The partially finished full basement provides additional living space ideal for a family room, recreation room, or home gym. Conveniently located just minutes from Highway 17, this property is ideal for commuters while still offering privacy and tranquility. Enjoy easy access to popular destinations including Resorts World Catskills, The Kartrite Resort & Indoor Waterpark, Bethel Woods Center for the Arts, and LEGOLAND. Come experience the beauty, privacy, and endless possibilities this exceptional property has to offer!

2643 State Route 209, Wurtsboro

$1,359,000

3 Beds ⋅ 3 Baths ⋅ 1009055 MLS

The Builder’s Personal Lakefront Masterwork. Crafted by its original owner, a meticulous contractor who built it for his own home. Designed with intention: cherry cabinetry and floors, cedar ceilings, ductless air, and an over-engineered foundation built to last. Wolf Lake: 1,800private acres of untouched forestland, miles of maintained hiking trails, three pristine spring-fed bodies of water, and a clubhouse with a full calendar of events. Wolf Lake is a community that is unmatched in its natural amenities and desirability, while just 90 min from the GWB. Wolf Lake is a very desirable community with its private lakes and picturesque surroundings, surrounded by natural forests and privacy. Welcome to 164 South Shore Drive, a stunning lakefront home with 4800 sq. ft., located in the picturesque community of Wolf Lake. Located in Rock Hill, New York. This beautiful property was built in 2008 and offers a perfect blend of modern amenities and classic charm. With 2 full bathrooms, 1 half bathroom, a spacious 2,800-square-foot living area, and a 1,800-square-foot walkout semi-finished basement, this three-story home is perfect for those seeking a peaceful retreat in the countryside. The home sits on a 22,000-square-foot lot, providing plenty of space for outdoor activities and entertaining guests. The tranquil surroundings make this property a true oasis away from the hustle and bustle of city life. As you step inside, you will be greeted by a warm, inviting atmosphere, with abundant natural light flooding in through large windows and a cathedral ceiling, overlooking Wolf Lake. The open concept layout of the main floor creates a seamless flow between the living room, dining area, and kitchen, making it the perfect space for hosting gatherings or relaxing with loved ones. The kitchen is a chef's dream, featuring modern appliances, ample cabinet space, and a center island with a second sink for added convenience. This kitchen has everything you need to create delicious dishes. The master suite has 2 closets and an ensuite bathroom, complete with a luxurious soaking air tub and separate oversized shower. Upstairs, you will find 1100 sq. ft. of spacious bedrooms and bathrooms, each offering comfort and privacy. Plus, an expansive balcony area looking out over the lake. The lower level of the home is a versatile space that can be used as a home office, gym, rec area, work, or additional living area. With direct access to the backyard, this area offers endless possibilities for customization to suit your lifestyle. Outside, the backyard is perfect for enjoying the fresh air and soaking up the landscape's natural beauty. An expansive view of the lake can be enjoyed from the deck off the first-floor living room or the patio outside the sliding doors from the basement. Whether you're hosting a barbecue, playing with pets, or simply relaxing on the patio, this outdoor space is sure to become your favorite spot to unwind. Fishing and swimming are optional! Located off the beaten track in a privately owned community featuring a 330-acre lake, 2–30-acre ponds, and 1800 acres of forest and trails, bordering thousands of acres of protected NYS land. The community offers a clubhouse, a sandy beach with lifeguards, and a private rifle range for target practice and trap shooting. This community is shareholder-owned by the community in the town of Rock Hill, NY. This property offers the perfect combination of privacy and community charm. With easy access to local amenities, schools, and outdoor recreational opportunities, this home truly has it all. Don't miss your chance to make 164 South Shore Drive your own slice of paradise in the Hudson Valley. One-time Wolf Lake membership fee of $5,250.

164 S Shore Drive, Wurtsboro

$849,900

3 Beds ⋅ 2 Baths ⋅ 999825 MLS

On any lake, the lot is everything and this property delivers the kind of waterfront that is increasingly difficult to find: level to gently sloping, just three steps down from the deck to the waterfront, a natural pebble-and-sand swimming area, and a private dock, all without the steep grades or soft bottoms that define so many lakefront parcels in the region. The lake-facing wall of windows fills nearly every main living space with water views, while lakeside deck, newly built in 2025, extends the living area directly toward the shoreline. This well-maintained chalet offers 3 bedrooms and 2 full baths across 1,767 square feet, with an open layout that provides genuine first-floor flexibility. Two bedrooms and a full bath are located on the main level, allowing comfortable single-level living if desired. Upstairs, the nearly 24x17 primary suite occupies the entire second floor, complete with its own bath and an open loft-style overlook toward the great room and lake below. Major infrastructure improvements are already in place, including a new house roof (2020), new deck (2025), new garage roof (2025), exterior painting (2021), propane hot water baseboard heat, drilled well, septic, and a detached oversized two-car garage with approximately 600 square feet of space plus a large stand-up storage loft accessible by a legitimate staircase. Located within Wolf Lake, one of Sullivan County’s most sought-after private lake communities, members enjoy access to approximately 1,800 acres of protected forestland, 3 spring-fed lakes, community beach, clubhouse, basketball court, playground, and recreational facilities, all approximately 90 minutes from the George Washington Bridge. Annual HOA: $1,350. One-time new-member fee of $5,250.

382 S Shore Drive, Rock Hill

$299,000

3 Beds ⋅ 1 Baths ⋅ 987715 MLS

Beautifully preserved and thoughtfully updated, this original 1930 Smallwood cabin offers the perfect balance of rustic charm and modern comfort. Immaculately maintained, the home features restored original wood floors, a bright and airy interior, and an inviting layout designed to bring the outdoors in. The sun-filled living space is complemented by a stone fireplace with insert, providing both ambiance and efficiency, along with a highly effective heating system for year-round comfort and central air for warmer months. Additional features include a renovated bathroom, partial basement with laundry, well and septic systems, and a brand-new paved driveway. Ideally located within walking distance to the lake, mini falls and scenic hiking trails, this property also offers optional membership to the Smallwood Civic Association ($350 annually per household), granting access to the community beach, lake, and amenities including boating. Enjoy close proximity to lakeside dining, Golf Course, Bethel Woods Center for the Arts, with Resorts World Catskills casino just a short drive away. Short-term rentals are permitted in the area, offering excellent investment potential. All of this, just under two hours from New York City.

64 Cumberland Trail, Smallwood

$774,900

977670 MLS

Strategic redevelopment opportunity in the southern part of the Town of Thompson offers favorable Commercial Industrial zoning and unlimited potential. This amazing corner property boasts extreme high visibility and a high traffic count. Directly facing NYS Rt 17/ Interstate 86 delivers the exposure that will surely make your business flourish. Large frontage of 850+/- feet on two roads makes this level land a perfect choice for development and offers terrific access for all types of vehicles, machines and parking. Located between highway exits 106 and 107, this prime spot offers added appeal. Active businesses in the immediate vicinity include tractor, truck and auto rentals and dealerships, professional offices and utility companies. Listing consists of two lots totaling 2.24+/- acres. One lot fronts on Bridgeville Road (Old Rt 17) and has a mixed-use building currently rented and used for storage. Total square footage is 3250+ not including a spacious breezeway that connects the two buildings which are a 3 BR house plus a small warehouse with overhead door. Front parcel is already cleared, and the back vacant lot which fronts on Southwoods Drive is wooded. Combine the two for your project or develop them both separately. Near to Crystal Run Healthcare, Resorts World Casino, Shopping, restaurants, big box stores, Village of Monticello, Holiday Mountain Fun Park and many other area attractions, services and bustling communities. Zoning chart is attached in docs.

740 Southwoods Drive, Monticello

$1,550,000

4 Beds ⋅ 4 Baths ⋅ 967208 MLS

Just 90 minutes from New York City, this custom 4-bedroom, 4-bathroom ranch residence set on 5+ private acres offers a rare balance of craftsmanship, scale, and pastoral beauty. Designed to capture both light and landscape, the home welcomes you with towering windows in the kitchen and main living spaces, where expansive views of open land and sky become part of the daily experience. Inside, the architecture celebrates handcrafted detail and natural materials. Solid wood finishes, artisan carvings, soaring ceiling heights, and a dramatic catwalk overlooking the main living area create warmth and visual impact. A private movie room adds comfort, making the home equally suited for entertaining or quiet evenings. The surrounding acreage invites a slower rhythm of life. Longhorn cattle grazing nearby enhance the authentic ranch setting, while the open land provides space well-suited for equestrian living. Properties offering luxury homes with acreage within 90 minutes of NYC are increasingly rare. Here, buyers can step directly into a completed residence: no construction timelines, no waiting: simply the opportunity to begin living the ranch lifestyle from day one.

55 Chapin Trail, Bethel

$900,000

4 Beds ⋅ 3 Baths ⋅ 959143 MLS

Welcome to 4 Lewis Lane, a striking contemporary residence that blends modern elegance with refined comfort. Offering four bedrooms, two and a half baths, and approximately 2,495 square feet of beautifully designed living space, this exceptional home is set on more than nine private acres within the Pine Bush School District, providing both serenity and convenience. From the moment you arrive, you are welcomed by an impressive oversized European front door that sets the tone for the sophisticated interior beyond. Inside, the home opens to a stunning open-concept layout enhanced by soaring vaulted ceilings and an abundance of natural light. The spacious living area features a sleek electric fireplace that creates a warm and inviting atmosphere throughout the cooler months, making it an ideal space for relaxing or entertaining. The kitchen is thoughtfully designed to serve as the heart of the home, showcasing an oversized island with extended quartz countertops that comfortably seat six. Custom cabinetry with tempered glass accents and interior LED lighting adds both style and functionality, while generous storage ensures effortless organization. A well-appointed laundry room with a sink and additional cabinetry provides everyday convenience just off the main living areas. The first-floor primary suite offers a luxurious private retreat, complete with vaulted ceilings and expansive European-style windows that flood the space with natural light. The en-suite bathroom is equally impressive, featuring dual vanities, a large tiled shower with glass doors, and a waterfall shower fixture for a spa-like experience. A spacious walk-in closet provides ample storage and completes the suite. The main level also includes a stylish half bath for guests. Upstairs, the open view overlooking the main living space enhances the home’s airy design. A second laundry area adds practical convenience, while three generously sized bedrooms provide comfortable accommodations, each with ample closet space and individual climate control through ductless mini-split systems. The second level also features a full bathroom with dual sinks and a beautifully tiled glass-enclosed shower. The lower level presents approximately 1,600 square feet of unfinished basement space, already equipped with ductless heating and cooling, offering endless possibilities for future customization. The garage is equally impressive with 15-foot ceilings, heated floors, and a Bluetooth-enabled garage door system. Built with spray foam insulation throughout, the home is designed for superior energy efficiency and year-round comfort. Step outside to enjoy the covered rear patio, complete with stamped concrete flooring and an oversized outdoor fan, creating an ideal setting for outdoor gatherings or quiet relaxation. Conveniently located near major highways including I-86 and I-84, this property offers easy commuting access while remaining close to popular destinations such as Resorts World Casino, The Kartrite Indoor Waterpark, Monster Golf Course, LEGOLAND, and Woodbury Common Premium Outlets. 4 Lewis Lane presents a rare opportunity to experience modern luxury living in a peaceful, expansive setting with exceptional amenities and convenient access to everything the region has to offer.

4 Lewis Lane, Bloomingburg

$1,570,000

5 Beds ⋅ 4 Baths ⋅ 947681 MLS

Time to Embrace CLOUD Cabin, a distinguished modern estate overlooking a premier Sullivan County Mountain View. This spectacular income-producing retreat spans 4295 SF across 2 homes. 125 Mapes Road in Barryville NY features luxury amenities all just 90 minutes the George Washington Bridge. This amazing private estate boasts only the best in luxury living from top end technology to upscale fixtures to gorgeous porcelain floors. With unparalleled finishes and exquisite design concepts, this custom home is suited for the person who wants only the best of country luxury living. Private and secluded with a quiet sophistication on 25 glorious acres of hardwood and pine trees. The stress of everyday living will disappear immediately upon entering this estate. Take a deep breath and enjoy the mountain views, enjoy an expansive great room with beamed cathedral ceilings, luxuriate in the private saunas or relax by your free standing fireplace. With the great room as the hub of the house boasting views galore, ample dining area and upscale custom kitchen you can entertain to your heart's content with plenty of room for all to enjoy. The right wing of the home houses the primary bedroom suite with an ensuite bathroom and a walk-in closet. The left wing of the home features 3 additional bedrooms, full bathroom and back office or entry room to an oversized garage. In addition to this fabulous main house there exists an equally exquisite guest home with its own outside sauna, mountain views, upscale kitchen, laundry room, bathroom and beautiful bedroom. The main Home is 3463 SF, Guest Home is 832 SF for a total of 4295 SF of Living Space. The expansive deck with panoramic mountain views is a site to behold with beautiful private tennis court and plenty of outside space to hike and explore. Currently this Income producing property is enjoyed by many who love the exquisite finishes, fabulous views and the serene atmosphere. This Spectacular Estate is conveniently located within 30 minutes to area conveniences and cultural events including hiking trails, Barryville Farmers Market, the Delaware River for recreation and Bethel Woods for music Venues, area cafes and bistros and Port Jervis Metro North rail trains.

125 Mapes Road, Barryville

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