Jeffersonville Real Estate

Welcome to Jeffersonville, New York – a hidden gem nestled in the picturesque Sullivan County. This charming hamlet, steeped in history and surrounded by the breathtaking beauty of the Catskill Mountains, offers a unique blend of rustic charm and modern convenience. Known for its friendly community and vibrant local culture, Jeffersonville is the perfect place to call home for those seeking a serene lifestyle away from the hustle and bustle of city life.

As you explore Jeffersonville, you’ll be captivated by its quaint streets lined with historic buildings, boutique shops, and delightful eateries. The town’s rich history is reflected in its architecture and community spirit, making it a wonderful place to engage with both neighbors and newcomers alike. Outdoor enthusiasts will find plenty to love, from hiking and fishing in the nearby Delaware River to enjoying seasonal festivals that celebrate the area’s heritage.

Jeffersonville is also conveniently located near larger towns, providing easy access to additional amenities while still allowing residents to enjoy the tranquility of small-town living. The local schools are highly regarded, making it an ideal choice for families looking to settle down in a nurturing environment.

Whether you’re searching for a cozy cottage or a spacious family home, Jeffersonville’s real estate market offers a variety of options to suit every lifestyle. Come discover the warmth and charm of Jeffersonville, where community, nature, and home come together in perfect harmony. Experience the magic of this Sullivan County treasure and start your journey to finding your dream home today!

Newest Listings in Jeffersonville

$189,000

2 Beds ⋅ 1 Baths ⋅ 1048789 MLS

Single wide situated on a lovely 3 + acres in kenoza lake, close to the hamlet of jeffersonville. Nice country road to call home. Mobile needs work or you can remove and replace. The land is mostly flat, with mobile situated back from the road for privacy. Wooded towards rear giveing a great view. This could be well worth the effort for affordable housing.

80 Swiss Hill Road N, Jeffersonville

$625,000

1044810 MLS

Endless possibilities on 6.36± acres in Jeffersonville, NY. Located just moments from State Route 52, this prime commercial property features a large distribution size warehouse and a separate detached office/workspace building. It can easily be configured into three or more separate leased units to maximize your return on investment. The main warehouse can be split into two distinct rental spaces each with their own private entrance. The back half was previously set up as a dog daycare with a fenced yard. The office/workspace includes a functional shop, office, bedroom, and full bathroom. The property has an expansive parking lot with tons of room to build out, expand, or maneuver large vehicles. Whether you want to launch, expand, or house multiple businesses, this versatile creative space is ready for your vision!

290 Jeffersonville North Branch Road, Jeffersonville

$1,025,000

1042947 MLS

Truly Unique Live-Work-Investment Opportunity...Nearly 8 Acres, 3 Buildings & Endless Possibilities! Rarely does an opportunity like this come to market! Set on 7.99 acres across multiple parcels, this one-of-a-kind property offers a spacious residential chalet plus two separate commercial buildings, creating an incredible opportunity for an owner-operator, investor, entrepreneur, or someone looking to combine home and business all in one location. The 3-bedroom, 3-bath chalet, built in 2004, is tucked beyond the commercial buildings and surrounded by mature woods, offering privacy and a peaceful residential setting while remaining conveniently close to the businesses. Inside, you'll find dramatic floor-to-ceiling windows, vaulted ceilings, knotty pine accents, hardwood floors, an open-concept kitchen with an expansive island, and a finished basement providing additional flexible space not included in the listed square footage. A wraparound deck, above-ground pool and new carport add to the outdoor appeal, with a paved driveway leading to the home. The two commercial buildings sit on approximately 2 acres with their own separate access and paved driveway. The first is an established dog boarding, daycare, grooming and retail facility, updated in 2021 and thoughtfully designed for a variety of pet-care uses. Features include a reception area, laundry facilities, grooming room, office, bathroom, retail space, camera system, covered outdoor runs, indoor/outdoor runs, play yard, parking and a dedicated cat area. The existing operation offers an opportunity for someone to continue the business, establish their own pet-care venture, expand services, or utilize the building for another permitted commercial use. The second commercial building is a two-story, approximately 2,800-square-foot building, built in 2008. The business currently operating there is not included in the sale, but the building itself offers tremendous potential for a variety of commercial uses, subject to zoning and approvals. With its size, layout and separate commercial setting, there may also be potential to explore alternative uses, including residential conversion, subject to municipal approval. Whether you're looking to live where you work, operate multiple businesses, generate rental income, create a compound, or explore an investment opportunity, this property offers a combination that is exceptionally hard to find. One property. Three buildings. Nearly 8 acres. Countless possibilities. Bring your vision and take advantage of this unique opportunity! Sullivan West School District & close to everything Jeffersonville & Callicoon have to offer!

5296 State Route 52, Jeffersonville

$950,000

5 Beds ⋅ 2 Baths ⋅ 1040100 MLS

Exceptional 33-Acre Equestrian Farm with Income Potential We are proud to present an incredible opportunity to own your very own equestrian farm with substantial income-producing potential. Welcome to Stone Wall Farm, a successful and well-established horse property situated on approximately 33 beautiful acres, just outside the sought-after hamlet of Jeffersonville. The impressive main barn is designed with both horse care and business operations in mind, featuring 18 spacious stalls and an incredible indoor riding arena, allowing for year-round use. The property offers numerous opportunities to generate income through horse boarding, riding lessons, training, clinics, events, and other equestrian activities. Adding even more versatility is the farm’s original barn, with the capacity to accommodate up to 15 additional horses or other livestock. The property is exceptionally well equipped with large established paddocks, an outdoor riding arena, workshop, equipment barn, manure barn, bulk feed bin, and existing hay contracts available if desired. The on-property trails wind through the acreage and alongside the picturesque creek that flows through the farm, creating a beautiful setting for horseback riding and enjoying the surrounding countryside. Completing the property is a spacious five-bedroom, two-bath residence featuring an inviting open-concept kitchen and living area—perfect for an owner/operator, farm manager, or anyone looking to enjoy the equestrian lifestyle right outside their front door. Whether you’re looking to operate an established boarding and equestrian business, expand a training or lesson program, create an event-based horse property, or simply enjoy your own private farm, Stone Wall Farm offers the acreage, infrastructure, and versatility to make it possible. A rare opportunity to own a turnkey equestrian property combining business potential, country living, and 33 acres of beautiful land in a desirable Catskills location.

139 Callicoon Center Road, Jeffersonville

$199,000

2 Beds ⋅ 1 Baths ⋅ 1039198 MLS

Enjoy peaceful country living with this ranch-style single-wide manufactured home situated on 4 beautiful acres of cleared land along a scenic country road. Offering 2 bedrooms, 1 full bath, and a bonus room, this property combines comfortable one-level living with exceptional outdoor space and multiple outbuildings. Inside, you'll find a welcoming living room, dining area, galley-style kitchen, and a large primary bedroom. A pellet stove provides warmth and cozy country charm, while an in-home washer and dryer add everyday convenience. French doors lead to the back deck, creating an easy connection between the indoor and outdoor living spaces. A covered patio provides plenty of room for relaxing, entertaining, or simply taking in the peaceful surroundings. The 4-acre property is a standout feature, with expansive cleared grounds and two ponds that add to the picturesque setting. There's plenty of room for gardening, recreation, or simply enjoying your own private piece of the countryside. For those needing garage, hobby, or workspace, the property offers excellent options. One garage features electric and a forced-air heater, providing a comfortable space for vehicles or projects throughout the year. A separate workshop/garage is also equipped with electric and multiple outlets, making it ideal for a workshop, storage, hobbies, or additional garage space. A 10kw standby Generac Generator is included. Close to Bethel Woods (original Woodstock Festival Site, Catskills Resort Casino, fishing, lakes, rivers and shopping.

290 Behr Road, Jeffersonville

$289,000

3 Beds ⋅ 2 Baths ⋅ 1028969 MLS

A true Jeffersonville original, thoughtfully prepared for its next chapter. Set along the banks of the gentle brook, this 1930 Craftsman has been carefully gutted, offering a rare opportunity to restore a home with authentic character while bringing your own vision to life. Originally built by the owners of nearby Kohler Lumber, the home still showcases many of its original Craftsman details, complemented by significant improvements already completed—including a new roof, new windows, fresh exterior paint, and updated mechanical systems—allowing you to focus on creating the interiors you've always imagined. Start your mornings with coffee on the charming riverstone front porch, spend crisp Catskills evenings gathered around the original wood-burning fireplace, and let the home's historic bones inspire what's next. A half bath off the kitchen presents an easy opportunity for expansion, while the original wood paneling upstairs adds warmth, texture, and timeless craftsmanship that simply can't be replicated. Outside, a detached two-car garage provides ample storage for outdoor gear, workshop space, or weekend projects. The backyard gently meets a brook, creating the kind of peaceful waterfront setting that defines life in the Catskills—whether it's quiet mornings by the water, cooling off on warm summer afternoons, or simply enjoying the soundtrack of a flowing creek. Just minutes from the heart of Jeffersonville's beloved shops, cafés, and local favorites, this is a rare chance to breathe new life into a classic Catskills Craftsman and create a home that feels both deeply rooted in history and distinctly your own.

5030 State Route 52, Jeffersonville

$649,000

3 Beds ⋅ 2 Baths ⋅ 1025090 MLS

Built in 2023 and set on 2.87 acres with a mountain view, this 3-bedroom, 2-bath home offers the benefits of new construction without the work that typically follows. Since completion, the property has been professionally graded and landscaped, evergreen trees have been planted, and a hot tub has been added, creating an established setting from day one. Inside, 1,370 square feet of bright, open living space features vaulted ceilings, oversized windows, wide-plank flooring, a wood-burning fireplace, and a spacious kitchen with Samsung appliances and a large center island. Sliding doors open to an elevated deck overlooking the backyard and surrounding hills. The primary suite includes a freestanding soaking tub, glass-enclosed shower and a large picture window. A full 1,370-square-foot walkout unfinished basement offers excellent potential for future living space, recreation, or storage. Just 3 minutes from Jeffersonville, with easy access to Sullivan Sundries, Ratty Books, Bloom Coffee, local dining, and the Delaware River, the home is equally suited as a full-time residence, weekend getaway, or investment property. With approximately $95,000 in Airbnb revenue generated since 2023 and furnishings available separately, it offers a rare turnkey opportunity in one of Sullivan County's most desirable locations. Under 2 hours to NYC.

12 Durr Road, Jeffersonville

$329,900

5 Beds ⋅ 3 Baths ⋅ 1029060 MLS

Diamond in the rough. Main house has been used as a two family in years past, building at back of property has one 3 bedroom, one bath apartment and the other apartment has been started but not completed. This property consists of 15 +- acres located in the RB district in the town of Callicoon, which means several possibilities for development including gas station. The East branch of the Callicoon creek weaves through the back of the property, large amount of open ground including an abundance of road frontage.

4369 State Route 52, Jeffersonville

$450,000

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

$325,000

4 Beds ⋅ 2 Baths ⋅ 1021280 MLS

Some streets just have a feeling, and Chapel Street is one of them. Towering shade trees and classic homes line this beloved street in the Village of Jeffersonville, welcoming you to a timeless Victorian ready for its next chapter. Step inside to discover four bedrooms, two full bathrooms, and beautiful hardwood floors that speak to the craftsmanship of another era. Every room offers the opportunity to blend historic charm with your own personal style, creating a home that's uniquely yours. Outside, the magic continues. Gather around the outdoor fireplace on crisp Catskills evenings, host friends in the spacious backyard, or simply enjoy the peaceful surroundings beneath the mature trees that make this property so special. Living here means more than owning a beautiful home; it's becoming part of one of Sullivan County's most vibrant village communities. Visit local craft fairs, shops, and community events, then spend your weekends exploring the mountains, lakes, farmers' markets, and endless outdoor adventures that make the Catskills such a treasured place to call home. If you've been searching for character, charm, and the chance to create something truly special, your story begins here on Chapel Street.

8 Chapel Street, Jeffersonville

$220,000

3 Beds ⋅ 2 Baths ⋅ 1013859 MLS

Enjoy space, scenery, and easy access to the best of the Sullivan Catskills with this well-maintained 3-bedroom, 2-bath mobile home set on 4.42 acres. The home features a large living room, comfortable layout, and plenty of room to relax indoors or out. A spacious deck accented by natural wood and stone invites you to take in the beautiful views and enjoy quiet mornings, outdoor meals, or evenings surrounded by nature. With over four acres, the property offers ample space for gardening, recreation, pets, gatherings, or simply enjoying the peaceful setting. Outdoor enthusiasts will love the location, with convenient access to the Delaware River area, Callicoon, and Roscoe. Nearby attractions include fly fishing, river activities, hiking, scenic drives, local shops, and a variety of well-loved restaurants throughout the region. Whether you are looking for a full-time residence, weekend getaway, or Catskills-area retreat, this property offers the combination of usable acreage, natural beauty, and proximity to recreation that makes country living so appealing.

673 Hessinger And Lare Road, Jeffersonville

$349,900

1010751 MLS

Discover the perfect setting for your dream home, country getaway, or recreational retreat on this beautiful 35± acre property in Western Sullivan County. A gentle rise in elevation creates stunning bucolic views and offers multiple ideal building sites to take advantage of the picturesque landscape. Featuring a wonderful blend of open meadows and wooded areas, the property is rich in character and natural beauty. Abundant wildlife makes it an excellent choice for nature enthusiasts, hunters, or anyone seeking a peaceful escape. Mature deciduous and evergreen trees, berry bushes, wildflowers, and ferns create a magical setting that changes beautifully with the seasons. Conveniently located near the villages of Jeffersonville and Callicoon for shopping, dining, and local charm. Enjoy easy access to the Delaware River for fishing, rafting, and outdoor recreation, as well as world-class entertainment at Bethel Woods Center for the Arts. Nearby lakes, boating, skiing, hiking, and countless outdoor activities make this an exceptional four-season destination. Whether you're looking to build, invest, or simply escape to the countryside, this remarkable property offers endless possibilities. Embrace the country lifestyle and make this special piece of Sullivan County your own. Two large warehouses and a scenic pond on an additional contiguous 5-acre parcel are also available for purchase, creating an exceptional opportunity for agricultural use, business expansion, storage, or the ideal live-work lifestyle. This versatile offering provides ample space for equipment, operations, hobbies, or a home-based enterprise, all in a beautiful rural setting.

TBD Jeffersonville North Branch Road, Jeffersonville

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