Highland, New York listings for sale

​
$499,999 - Highland, NY
290 Tuckers Corners Road Highland, NY - Discover the perfect blend of comfort, convenience, and potential in this well-maintained ranch-style home, built just eight years ago and nestled on 15 subdividable, buildable acres in Highland, NY. Whether you’re a builder, investor, or simply seeking a peaceful retreat with room to expand, this property is an exceptional find. The move-in ready home features central air, a heat pump, and a full-house generator, ensuring year-round comfort and reliability. Inside, you’ll find a bright, welcoming layout with modern finishes, while outside, the expansive acreage offers limited farming capabilities, including space for horses. An attached two-car garage adds to the convenience, and with nothing to do but move in, this is a rare opportunity to own a turnkey property with incredible development potential. The sellers are highly motivated, so don’t miss out on this chance to make it yours! Schedule a showing today!
2018 | 3 | 2 | 1,560 sqft.
​
$475,000 - Highland, NY
224 Martin Avenue Highland, NY - Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom has a large full bath, perfect for comfortable living. As you step inside you will be greeted by beautiful wood floors that flow seamlessly throughout the living spaces. The spacious kitchen boasts a charming breakfast area with sliders leading to the stone patio, making it the ideal spot for casual dining or morning coffee. The inviting living room complete with fireplace and vaulted ceilings creates a warm atmosphere for relaxation and entertaining. The upstairs loft area overlooking the living room extends into a perfect third bedroom. Step outside to enjoy beautiful open manicured grounds with garden area and stone patio. Take a summer’s swim in your own pool with wrap around decking. This home is your perfect country retreat.
1940 | 3 | 2 | 1,633 sqft.
​
$464,900 - Highland, NY
6 Smith Terrace Highland, NY - Discover the perfect blend of modern style, flexible living, and serene surroundings in this beautifully updated ranch-style home, ideally located in the scenic town of Highland. Offering 1,728 sq ft of thoughtfully designed space, this 4-bedroom, 3-bathroom gem includes a fully legal 1-bedroom accessory apartment—making it as functional as it is stunning. From the moment you arrive, you’ll be impressed by the home’s fresh, contemporary façade—featuring brand-new windows, a spacious front deck, and multiple outdoor living areas perfect for morning coffee, weekend gatherings, or simply soaking in the peaceful vibe. Step inside to an open-concept layout drenched in natural light, where hardwood and tile flooring, wood-accented ceilings, and tasteful finishes create a warm and inviting atmosphere throughout. Every inch of this home has been designed with comfort and style in mind. The renovated kitchen is a true centerpiece, boasting sleek black cabinetry, butcher block countertops, open shelving, and brand-new stainless-steel appliances. Whether you're a culinary enthusiast or a casual cook, this space combines beauty with functionality. The adjacent dining area is framed by large windows and sliding glass doors, offering tranquil views and direct access to the front deck—perfect for al fresco dining. Need flexible living space? The newly added 1-bedroom accessory apartment features a separate entrance, kitchenette, and full bath—ideal for additional living space, guests, a home office, or potential rental income. Plus, it’s ready to be metered separately, giving you ultimate control and value. Two of the three bathrooms have been completely renovated with new plumbing, electrical, and on-trend fixtures. The third bath is move-in ready but offers a unique chance to add your personal touch. Enjoy two spacious decks, a partially level yard surrounded by mature trees, and plenty of space to entertain or relax in nature. A new French drain system ensures peace of mind, and the property is pre-wired for three mini-splits—making energy efficiency easy and attainable. Nestled in a residential neighborhood, you’ll enjoy quick access to local amenities, dining, shopping, hiking trails, and major commuter routes. Just minutes from the Mid-Hudson Bridge and everything the vibrant Hudson Valley has to offer.
1956 | 4 | 3 | 2,100 sqft.
​
$425,000 - Highland, NY
59 South Street Highland, NY - Charming 1900 Two-Story Farmhouse with Vintage Character... Step into timeless charm with this lovingly cared for two-story farmhouse, built circa 1900 and brimming with original character. Featuring authentic hardwood floors, this 2-bedroom home offers cozy living spaces, walk-in closets, and a woodstove perfect for those crisp Hudson Valley evenings. Enjoy peaceful mornings on the classic closed-in porch and relaxed afternoons on the spacious back porch, overlooking an open back yard adorned with mature plantings and vibrant flower beds—a gardener’s dream. A barn-style detached garage adds rustic charm and practical storage space, ideal for hobbies, vehicles, or a workshop. Perfectly situated just minutes from retail shopping, the NYS Thruway, Walkway Over the Hudson, and scenic biking trails, this home offers a unique blend of country living with easy access to modern conveniences. Don’t miss your chance to own a slice of Hudson Valley history—schedule your tour today!
1900 | 2 | 1 | 1,365 sqft.
​
$399,900 - Highland, NY
546 South Street Highland, NY - Located in the heart of the Hudson Valley, this spacious 2,500 sq ft home in Highland blends classic charm with modern upgrades—perfect for those who crave room to grow and a connection to the outdoors. The first floor features a warm and inviting living room, a large dining area ideal for gatherings, an efficient kitchen ready for your personal touch, a private laundry room, and a convenient first-floor bedroom. Upstairs, you’ll find four additional bedrooms and a full bathroom, offering flexibility for home offices, guest space, or creative studios. Recent upgrades bring peace of mind and comfort, including spray foam insulation, brand-new siding, a new roof, and all-new windows—so the heavy lifting has been done for you. Set on a generous lot with space to play, garden, or simply unwind, this home is a true gateway to the best of the Hudson Valley. Just minutes from the Shawangunk Ridge, Mohonk Mountain House, and endless rail trails, it offers adventure out your front door and small-town charm all around. With easy access to New Paltz, Kingston, and the Metro-North line, you can enjoy both weekend escapes and everyday convenience.
1932 | 5 | 2 | 2,500 sqft.
​
$329,000 - Highland, NY
37 Maple Avenue Highland, NY - Freshly redone, Colonial style house 1,000 feet to the Hudson & Highland Landing Park. The open floor plan downstairs gives that airy fresh touch. Beautiful all new kitchen and appliances. Lots of windows. Upstairs, 3 spacious bedrooms and 2 full bathrooms. Make this opportunity your home and enjoy the beauties of the Hudson and this sweet contemporary home.
1800 | 3 | 2 | 1,121 sqft.
​
$299,000 - Highland, NY
460 Vineyard Avenue Highland, NY - This property in Highland is a charming two-story home that offers a blend of comfort and modern amenities. This spacious residence features a dedicated office space, perfect for remote work or study. The kitchen has been newly renovated, boasting beautiful granite countertops and elegant wood cabinetry, making it both functional and stylish. For those who appreciate organization, a large pantry provides ample storage for all your kitchen essentials. The home is adorned with laminate flooring throughout, giving it a contemporary and low maintenance appeal. Convenience is at its best with a designated washer and dryer area, ensuring laundry days are hassle-free. The property includes a one-car garage, offering protected parking or additional office space. Outside, the nice backyard provides a relaxing outdoor space, ideal for gatherings, gardening, or simply unwinding in the fresh air. Overall, this property is an excellent blend of practicality and modern living. The perfect commuter location, just minutes to Metro North.
1950 | 2 | 2 | 1,470 sqft.
​
$299,000 - Highland, NY
460 Vineyard Avenue Highland, NY - This property in Highland is a charming two-story home that offers a blend of comfort and modern amenities. This spacious residence features a dedicated office space, perfect for remote work or study. The kitchen has been newly renovated, boasting beautiful granite countertops and elegant wood cabinetry, making it both functional and stylish. For those who appreciate organization, a large pantry provides ample storage for all your kitchen essentials. The home is adorned with laminate flooring throughout, giving it a contemporary and low maintenance appeal. Convenience is at its best with a designated washer and dryer area, ensuring laundry days are hassle-free. The property includes a one-car garage, offering protected parking or additional office space. Outside, the nice backyard provides a relaxing outdoor space, ideal for gatherings, gardening, or simply unwinding in the fresh air. Overall, this property is an excellent blend of practicality and modern living. The perfect commuter location, just minutes to Metro North.
1950 | 2 | 2 | 1,470 sqft.
​
$239,900 - Highland, NY
534 New Paltz Road Highland, NY - Move-in Ready Gem-Perfect for Easy Living in Highland, NY Step into this completely renovated 1-Bedroom, 1-Bath home designed for comfort and convenience. The entire house has been fully renovated featuring New Septic System, New Roof, New Electrical, New Plumbing, New Washer/Dryer hook up, New water heater, New Electrical panel 200 amp, New Sheetrock, New wall and ceiling insulation, New Windows and trim, New heaters, New baseboards, New doors, hinges, knobs, trim, New kitchen cabinets, New butcherblock, New kitchen farmhouse sink, and faucet, New Bathroom vanity and faucet, New Shower door, New Range, New Over the Range Microwave, New refrigerator, New dishwasher, New Interior Paint, Newly exterior paint, New Blinds, New Privacy Fence, New Bilco Door, New gutter and downspouts, New Flooring, New bathroom fixture and accessories, New toilet seat, New light fixtures. The layout is versatile and functional, making it ideal for any stage of life. Whether you're starting fresh, simplifying your lifestyle, or just looking for a space that's easy to maintain, this home offers the perfect balance of style and practicality. The low-maintenance lot ensures you can spend less time on upkeep and more time enjoying what matters most. Located just 5 minutes from the NYS Thruway and a short drive to the Poughkeepsie train station, this home provides easy access to all the Hudson Valley has to offer—from scenic outdoor activities to great dining and local attractions like the Walkway Over the Hudson and access to the Hudson Valley Rail Trail only a few hundred feet up the road. Ready for simple, stylish living in a prime location? This fully updated home is move-in ready and waiting for you to make it your own. Don't wait—come see it and make it yours!
1960 | 1 | 1 | 762 sqft.
​
$165,750 - Highland, NY
854 New Paltz Road Highland, NY - **Multiple offer situation. Seller requesting highest, best and final offers 8am, 4/10/2025.** Seclusion awaits you in this bird watcher's paradise. Feel like you're miles away from everything but only a short trip to the town center. Great weekend getaway! Cottage with balcony overlooking huge living room. Several outbuildings, barns, garages, etc. Over 10 acres of privacy! SUV is recommended to access - long and curvy driveway through the woods (currently snow covered) to the house. Sold as-is. Buyer to pay NYS and any local transfer taxes. Cash offers only with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**
1900 | 1 | 1 | 1,596 sqft.