Jeffersonville Homes for Sale

Welcome to Jeffersonville, Indiana – a vibrant city that beautifully blends the charm of a small town with the conveniences of modern living. Nestled along the banks of the Ohio River, Jeffersonville is part of the greater Louisville metropolitan area, offering residents easy access to the bustling city life just across the river while maintaining its own unique character.

Rich in history and culture, Jeffersonville is known for its stunning historic architecture, including the iconic Big Four Bridge, which connects to Louisville and serves as a scenic pedestrian walkway. The city boasts an array of parks, delightful local eateries, and a burgeoning arts scene, making it an ideal place for families, young professionals, and retirees alike. With its friendly community atmosphere and a variety of recreational activities, Jeffersonville truly embodies the essence of Midwestern hospitality.

For those considering a move to this charming city, there are a variety of homes for sale that cater to diverse lifestyles and budgets. From quaint bungalows nestled in tree-lined neighborhoods to modern townhomes with stunning river views, Jeffersonville offers a wide array of real estate options. Whether you’re looking for a cozy starter home or a spacious family residence, you’ll find properties that suit your needs and preferences.

Explore the possibilities of calling Jeffersonville home, where you can enjoy a rich community life, beautiful surroundings, and a range of amenities right at your fingertips. Discover your dream home in this delightful city and become part of a community that welcomes you with open arms!

Newest Jeffersonville Homes for Sale

$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

$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

$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

$349,900

3 Beds ⋅ 2 Baths ⋅ PAMC2175758 MLS

Craftsman style Cape in need of TLC and being sold in "As-Is" condition. Nice location and situated on quaint street with tall shade trees & great location, this expansive single enjoys tons of old world charm with a full length enclosed porch, large living room & traditional dining room. The main level also features a sizeable 1st floor bedroom, full bath, and kitchen. The upper level offers two (2) large bedrooms, multiple closet/storage areas, laundry hook-ups and half bath! The home has thermal window updates, updated roof (approx. 2015), and efficient 4-zone mini-split system (installed approx. 2021). In the basement is an additional laundry hook-up as well ample bonus storage space! Home is situated on a .21 acre lot with detached garage and off-street private parking aside garage for 3 vehicles. Home is convenient to major routes, restaurants & shopping, and just minutes to the Schuylkill River Trail - call & schedule your visit today!

1924 Juniata Rd, Jeffersonville

$549,000

4 Beds ⋅ 3 Baths ⋅ 982657 MLS

Enjoy unforgettable sunsets from this beautifully renovated 4 bedroom, 3 bath home set on 1.5 acres. Designed for both comfort and entertaining, the home features oversized double back decks that seamlessly extend your living space outdoors. Inside, warm wood floors, recessed lighting, and spacious rooms create a bright and inviting atmosphere, complemented by large walk in closets and a practical layout. A 2 car garage and easy main road access add everyday convenience. The home's accessible location means easy winter access without long winding driveways to maintain. You’ll enjoy a quick connection to main roads while still appreciating a peaceful sense of privacy from inside the home and from the backside of the home that feels like you're miles away from everything. This home is the perfect blend of comfort and style, making it an ideal retreat. Buy now and be in by summer. Start making unforgettable memories. Minutes from village of Jeffersonville's charming main street offering restaurants, shops and everyday essentials. Not far from Bethelwoods Performing Arts Center, Resorts World Casino and Kartrite Indoor Water Park. Buyer to do due diligence and verify all information.

4741 State Route 52, Jeffersonville

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