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

$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

$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

$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

$230,000

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

$849,900

1007322 MLS

With more than 15,000 square feet of space, acreage, and three-phase electric, these two connected clear-span buildings present an exceptional opportunity. Located in Sullivan County just two miles from State Route 52, the property is offered with 5 acres and the option to purchase an additional 35+/- additional acres, an impressive and flexible package. Warehouse properties of this size and versatility rarely come to market. Situated in a rural agricultural setting, this property is ideal for farmers, manufacturers, contractors, storage operations, woodworkers, machinists, light industrial uses, and a variety of commercial ventures. It also offers potential for a live/work commercial-residential arrangement. The buildings are perfectly configured for woodworking, manufacturing, warehousing, equipment storage, and other business operations. The gently sloping land features a pond that can serve as a valuable water source for safety and operational needs. Ample parking, extensive road frontage, and easy ingress and egress make the property highly functional, with plenty of room to accommodate tractor-trailers and other large vehicles. Whether you're expanding an existing business or launching a new enterprise, this unique property offers the space, infrastructure, and flexibility to help your vision grow.

295 Jeffersonville North Branch Road, Jeffersonville

$389,000

3 Beds ⋅ 1 Baths ⋅ 989485 MLS

Waterfront on Main- 4929 Route 52 is a beautifully maintained 1930s-era Sears kit home, showcasing timeless character and an array of charming original details throughout. Recent renovations have thoughtfully restored and highlighted the home's original woodwork, bringing its historic charm back to life. The property features more than 90 feet of frontage on the Callicoon Creek and enjoys a convenient location just moments from the shops, restaurants, and amenities of Main Street in Jeffersonville. Combining waterfront living with unbeatable access to town, this property offers a rare and highly desirable setting. The main level features a spacious living room with original hardwood floors, creating a warm and inviting atmosphere. The renovated kitchen blends modern conveniences with carefully restored period details and includes a large pantry closet for additional storage. Also on this level are a generously sized bedroom and an updated full bathroom with a bathtub. Upstairs, you'll find two additional bedrooms and a versatile home office, ideal for remote work or flex space. The unfinished basement offers a dedicated laundry area and abundant storage space. The outdoor space is a true highlight of the property. Relax with friends on the covered front porch or enjoy your morning coffee on the rear deck overlooking the sights and sounds of the rushing creek. The spacious backyard provides ample room for recreation, gardening, or simply unwinding in a peaceful natural setting. Whether hosting guests, dining outdoors, or enjoying quiet evenings by the water, you'll appreciate the unique creekside setting and exceptional outdoor living opportunities this property offers. The property benefits from shared use of a portion of the neighboring store’s paved parking lot, providing ample off-street parking for residents and guests. An oversized detached garage offers additional parking, storage, or workshop space. Convenient shopping, dining, and everyday amenities abound along Main Street including Peck’s Supermarket, Jeffersonville Bake Shop, Jeff’s Diner, Michelangelo’s Pizzeria, Tavern on Main, Cuppie Cake Desserts, Double D Sourdough, Carousel Ice Cream, Sullivan Sundries, Jefferson Pharmacy, and The Catskill Outdoorsman. Residents can enjoy the charm of a small-town setting while having a wide variety of services, restaurants, and local businesses right at their doorstep. Previously operated as a successful short-term rental, this versatile property offers excellent potential as an investment opportunity, weekend retreat, or full-time residence. Conveniently located within easy reach of New York City, it provides the perfect balance of small-town charm, waterfront enjoyment, and accessibility.

4929 State Route 52, Jeffersonville

$175,000

999834 MLS

This exceptional parcel with great views offers a rare combination of location, accessibility, and homesite potential. Situated in a desirable and growing area, the expansive property features optimal topography, excellent road frontage, and convenient access to many local towns including Jeffersonville, Callicoon, LIberty and Roscoe where you'll find many of the areas restaurants and shopping.

52 E Hill Road, Jeffersonville

$650,000

3 Beds ⋅ 3 Baths ⋅ 990308 MLS

Let country roads take you home to this charming retreat, set on a beautifully private parcel. Tucked deep into the rolling hills of Jeffersonville, this well-maintained and recently updated, custom-built 2004 home delivers a rare combination of total privacy, timeless craftsmanship, and stylish modern updates—all just minutes from town. Set far back from the road amid native landscaping, private woods, and a spring-fed pond, the home immediately welcomes you with warm cedar siding and an unmistakable sense of calm. Inside, soaring vaulted ceilings and a stunning three-story chimney—built from stone harvested directly on the property—create a dramatic focal point, while fresh paint, updated lighting, and newly installed hardwood floors bring a refined, contemporary feel throughout. The beautifully renovated kitchen features a center island, custom sage-green cabinetry, quartz countertops, stone floors, and an effortless flow into the dining and living spaces before opening onto a spacious deck overlooking the water. It’s the perfect setting for entertaining, outdoor dining, or quiet mornings with coffee and birdsong. Currently configured as a two-bedroom home with easy potential for a third small bedroom which is currently staged as an open office space, the layout includes a primary suite and a spacious, ~500-square-foot walk-out lower level with French doors and a cozy Vermont Castings wood stove. There is also a heated, insulated two-car garage with polished concrete floors and cedar accents that feels more like a designer workshop or studio than a garage. Combining turnkey comfort with room to create your own Catskills sanctuary, this exceptional property offers peaceful country living just eight minutes from the growing energy of “Jeff,” with the ever-popular destinations of nearby Livingston Manor and Callicoon close at hand. Sellers are optionally open to a long-term lease of the home. Just under 2 hours from the George Washington Bridge.

22 J Spielman Road, Jeffersonville

$545,000

3 Beds ⋅ 2 Baths ⋅ 1002192 MLS

Love grand old homes, privacy and large airy rooms with lots of natural light? Have porch goals? Then this is the home for you. The home has been lovingly undergoing a restoration. Wood floors have been brought back to life in most of the home reflecting the care that was taken with them. The bathrooms have stayed true to the original time period with fully functioning sinks, toilets and clawfoot tub with shower. Venetian plaster glows in the upstairs bedrooms, hallway and attic. The spacious living room has been painted with a lime wash. With a woodstove keeping you cozy on cooler days. New chimney and gutters are part of the beauty. The kitchen is large enough that when entertaing guests they can hang out and keep you company while getting your chef on. Off the kitchen is a butlers pantry with a seperate entrance to the back yard. You can enter the kitchen through a mudroom with places for coats, boots and handy tools. Many of the ceilings are wainscoted. The attic is the bonus. It could easily be turned into an additional bedroom suite, art studio with lots of natural light, extensive library or a private sanctuary. Sit on the porch in the morning with a cup of tea or coffee and enjoy a crossant while reading the paper or watching the birds. Out side is a gardener's paradise with a small orchard with peach, plum, apple, pear and cherry trees. There is also a grape arbor. Daffodiles, peonies, lilacs, violets and many other flowers and herbs abound. A secret club house is tucked in the back yard. A brook meanders down the side of the property. The home sits well back from the road. A two minute drive to Jeffersonville which has a grocery store, bakeries, pharmacy, speciality stores, restaurants, ice cream stand and the library. It is an short 8 mile drive to Bethel Woods. Not far from Callicoon and the Delaware river, Livingston Manor and Roscoe for trout fishing. Less then 2 hours from the GWB and an easy drive from Route 17.

4700 State Route 52, Jeffersonville

$389,000

3 Beds ⋅ 2 Baths ⋅ 999068 MLS

Kohler Craftsman is a charming 105-year-old storybook home located in the vibrant Village of Jeffersonville. Rich in character and history, this well-maintained residence offers 3 bedrooms, 1 full bathroom, and 1 half bathroom on a beautifully landscaped and private 0.38-acre lot. The fenced yard features a heated above-ground pool, grassy lawn, and a spacious two-car garage. Originally built by the Kohler family, founders of the neighboring Kohler Lumber business, this exceptional home has been lovingly cared for by only three families throughout its history. Timeless craftsmanship and original architectural details remain beautifully preserved, including hardwood floors, rich wood trim, custom built-ins, and handsome cabinetry throughout the home. Enter through the inviting eat-in kitchen, complete with generous pantry storage and a sun-filled breakfast nook perfect for casual dining. The kitchen flows into a formal dining room featuring elegant French doors and built-in cabinetry, creating an ideal setting for entertaining and gatherings. The spacious living room is highlighted by a large picture window and a cozy propane fireplace. Just off the living area is a delightful office nook, currently used as a creative space for painting and music, offering flexibility for work or hobbies. Completing the main level is a convenient half bathroom and a versatile bonus room connecting the home to the garage. This flexible space could serve as a guest room, recreation area, or mudroom. Upstairs, you will find three comfortable bedrooms and a full bathroom. Both guest bedrooms offer ample closet space, while the primary bedroom features both a large closet and a substantial built-in wardrobe for additional storage. Additional features include a full unfinished basement with a wine and root cellar, as well as a large attic space above the garage complete with a cedar-lined closet for long-term storage. Thoughtfully maintained over the years, the home has seen important mechanical updates, including improvements to the boiler, fuel tank, and water system. Kohler Craftsman presents a rare opportunity to own a historic home filled with warmth, character, and enduring craftsmanship while beginning the next chapter of its story.

5026 State Route 52, Jeffersonville

$365,000

3 Beds ⋅ 2 Baths ⋅ PAMC2175758 MLS

COMING SOON - Craftsman Style Cape On Quaint Street With Tall Shade Trees & Great Location! This Expansive Single Enjoys The Mixes Of Some Modern Updates With Tons Of Old World Charm - Including Bright & Sunny Full Length Enclosed Porch, Classic Woodwork & Traditional Solid Wood Doors With Period Hardware & Glass Knobs! Featuring A Pebble-Dash Exterior Finish, The Home Boasts Thermal Windows, Updated Roof (2015 approx.) And Super Efficient 4-Zone Mini-Split System (2021). There's Laundry Hook Ups Available On Both 2nd Floor And Basement Levels Where You'll Be Please To Discover Ample Bonus Storage. Home Is Situated On .21 Acre Lot With Oversize Detached Garage And Off-Street Private Parking For 3 Vehicles. Super Location And Just Minutes To The Scenic Schuylkill River Trail, Restaurants, Shopping & Major Routes. Schedule Your Visit Today!

1924 Juniata Rd, Jeffersonville

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