Highland New York homes for sale starting at Fifty Thousand Dollars

$995,000 - Highland, NY

370 N Elting Corners Road Highland, NY - Tucked away on a peaceful hilltop just 7 minutes from the heart of New Paltz, this stunning 1930s Dutch Colonial has been completely reimagined—where old-world charm meets modern craftsmanship and curated design. Renovated from top to bottom by ANVO Construction with deep intentionality, this is more than a home—it’s a legacy project. Set in Highland with New Paltz schools, it offers the best of both worlds: rural tranquility and easy access to restaurants, trails, Metro-North, and the Thruway (just 20 minutes to MTA and Amtrak). The main level features a warm, light-filled layout designed for both daily life and effortless entertaining: a ground-floor bedroom, a gorgeous living room with wood stove and custom built-ins, a dining room with exposed wood beam ceilings, a fully remodeled full bathroom, and an incredible sunroom that blurs the line between indoors and out. The kitchen has been thoughtfully updated while maintaining the home’s timeless charm. Upstairs, you’ll find three additional bedrooms, a second fully renovated full bathroom, and a bonus den/office that easily functions as a fifth bedroom. A walk-up third-floor attic serves as a creative playroom or retreat, complete with a climbing wall and chill-out zone. The basement is a woodworker’s dream—fully dry, spacious, and already equipped as a full workshop. Inside, original character remains intact: ingrained hardwood floors, wood-paneled ceilings, and rich original moldings. Yet every inch has been thoughtfully modernized. Central heating and cooling, a hemlock-screened porch addition, fully insulated walls, and opened ceilings elevate the space without losing its soul. And then there’s the barn. Dating back to the 1850s and now fully transformed into a year-round creative space, it’s a rare Hudson Valley gem. With water, WiFi, electric HVAC, and a drain system already in place, it’s primed for conversion to guest quarters or a private live/work studio. A new driveway leads directly to it for easy access and future flexibility. The grounds have been equally considered. Landscapers and permaculture designers regraded the land, added swales, planted over 30 trees, and uncovered three natural streams—creating a landscape that’s both stunning and sustainable. This home wasn’t built to sell. It was built with care, vision, and long-term purpose—over five years of thoughtful craftsmanship. Sunsets, mountain views, a flat lawn for play, and gardens ready to bloom—just minutes from Mohonk, rail trails, and all the best of the Hudson Valley. This is more than a property. It’s a place to live, create, and build something that lasts.

$769,000 - Highland, NY

2 Fieldstone Court Highland, NY - Stunning colonial with contemporary flair gem boasts 4 large spacious bedrooms and 2.5 luxurious bathrooms, providing ample space for comfortable living. Step inside to discover a beautifully updated interior with modern finishes throughout. The 2-story living room creates an inviting space for gatherings, while the chef's kitchen features a sleek open layout, ideal for entertaining guests. Have family gatherings in the partially finished basement, offering additional living or Dive into relaxation in your very own inground heated saltwater pool, perfect for year-round enjoyment. Never worry about power outages with the added convenience of a whole house generator. Enjoy the beautifully landscaped 1.57 acres complete with sprinkler system. This home is your castle and only 1 hour from NYC and close to all major highways, Stewart international airport and all other mass transportation.

$729,000 - Highland, NY

$625,000 - Highland, NY

11 Fieldstone Court Highland, NY - Built in 2018, this home is like new construction without all of the challenges, decisions and delayed timelines! Located on a cul de sac, well set back from the road with an abundance of privacy. Ideal as your full time residence or an escape from the hectic day to day. A trafficless drive could get you there in under 2 hours from NYC and is located an hour from the Catskill Mountains. Since buying new the seller paved the driveway, installed whole house Generac generator, put in Central Air, built two large pristine sheds, installed privacy fencing and much more. The security features of the home are sure to impress anyone seeking some extra piece of mind. Crimsafe window/door screens, top notch exterior camera system (included) and Cornell garage doors are just the beginning of the security here. Minutes to the Mid-Hudson Bridge, just off 9W and close to all the Hudson Valley has to offer.

$600,000 - Highland, NY

191 Bedell Avenue Highland, NY - Welcome to 191 Bedell Ave in Highland, a move-in ready gem blending classic charm with modern updates! This beautifully maintained home features cathedral ceilings, hardwood floors, abundant natural light, and spacious living areas perfect for relaxing or entertaining. This sprawling raised ranch includes 5 bedrooms, 3 baths, and tons of living space on 1.46 Acres! Sit back and relax in the fully screened in porch, or large living room featuring a wood-burning stove, cathedral ceilings, and mountain views. Enjoy the updated kitchen with a center island with built in cooktop, stainless steel appliances, and loads of storage! Outside boasts a large, level yard ideal for gardening, pets, or entertainment. The large greenhouse and 2 fenced in gardens are ready for their next caretaker. Located on a quiet street just minutes from shops, schools, and major highways. This is the one you’ve been waiting for. Don’t miss it!

$595,000 - Highland, NY

745 State Route 44 55 Highland, NY - Now Fully Available — Modern Farmhouse in Prime Highland Location This beautifully restored farmhouse perfectly balances historic charm with modern upgrades. Set on a scenic acre in the Highland School District, the home offers sun-filled interiors, soaring ceilings, and an open-concept layout designed for easy living. The first-floor primary suite adds comfort and convenience, while three upstairs bedrooms surround a loft-style balcony overlooking the main living space. A sleek, modern kitchen and central home office make it ideal for today’s lifestyle. Enjoy peace of mind with a brand-new roof, high-efficiency hot water heater, upgraded electrical, and mini-split systems in every room. A central wood stove adds warmth and character. Outside, a covered front porch with elevated views sets the tone for tranquil living, while the manicured yard offers plenty of space to relax or entertain. Minutes from the Walkway Over the Hudson and local rail trails, this is Hudson Valley living at its finest. Don't miss out—schedule your private showing today.

$575,000 - Highland, NY

17 Dogwood Knolls Highland, NY - Incredible home with stunning renovations; this one of a kind raised ranch has over 2,200 sq.ft. featuring 3/4 bedrooms two and a half baths, PLUS bonus room and 2 car garage. Located in a peaceful setting of 3.3 private acres on the dead-end road; you get the "best of both worlds" a residential neighborhood that's also easily accessible to main roads, shopping and restaurants! This home has upgrades galore and is ready to move right in! High end vinyl floors beautifully flow throughout both levels adding elegance and durability. The entry way foyer is wide with a gorgeous light fixture immediately setting the tone for the warmth ahead. You'll love the open floor plan with combined living room, dining and eat in Kitchen; accented by vaulted ceilings and fresh paint. The Kitchen is a dream! Stunning modern cabinetry, with soft close drawers, quartz counters, range hood and an expanded center island (great perk!), tile back=splash and all new appliances complete this space. Nearby you'll have the advantage of the private backyard and adjacent side yard combining plenty of space for total outdoor enjoyment. The expansive deck is brand new and it has stairs leading to the yard helping make entertaining a breeze! All three bathrooms have been redone to perfection! Notice the details in tile-work and overall design the current owner has selected. All three vanities were custom chosen. A unique blend of modern style while preserving charm and a welcoming environment. Additional updates include: new roof, new furnace, new above ground oil tank, newly installed water treatment system, updated light fixtures and fresh paint throughout, totally redone driveway. Come and take a look at all there is to appreciate here. This immaculate home is inviting and offers a relaxing ambiance...you'll love coming home here!

$575,000 - Highland, NY

27 Salk Drive Highland, NY - Welcome to this beautifully maintained 4-bedroom, 2.5-bath Colonial perfectly blending timeless charm with modern conveniences. Located in a great commuter location, just minutes from the Mid-Hudson Bridge and local shopping, this home offers space, comfort, and unbeatable accessibility. The inviting living room features a cozy fireplace, ideal for relaxing evenings, while the family room and formal dining room provide flexible space for entertaining and everyday living. The heart of the home is the updated eat-in kitchen, complete with stainless steel appliances, a center island, and plenty of counter space for cooking and gathering. Upstairs, the primary suite features a walk-in closet and a private bath. Three additional bedrooms and a convenient second-floor laundry add everyday ease. Step outside to the back deck with a retractable awning, perfect for enjoying your morning coffee or evening downtime in any weather. The private backyard offers a peaceful retreat with space for gardening, entertaining, or simply relaxing. Pride of ownership shows throughout, from the meticulous upkeep to thoughtful updates. Additional features include an oversized 2-car garage, rocking chair covered front porch and a full unfinished basement with endless potential for storage or future living space. This move-in ready home truly has it all—style, comfort, and location!

$549,000 - Highland, NY

42 Bell Drive Highland, NY - Welcome to 42 Bell Drive, a beautifully sited, oversized Raised Ranch nestled in the magical hamlet of Highland. Perched atop a gentle hill and surrounded by mature trees, this 2,100+ square foot home offers a perfect blend of space, light, and serenity. The main level features vaulted ceilings, a fireplace, and a bright, open-concept living and dining area that flows effortlessly into a large, well-appointed kitchen — ideal for entertaining or everyday living. The thoughtfully designed floor plan offers separation and privacy, with a generously sized primary suite with en suite bath on one side of the home, and two additional bedrooms and a full guest bath on the other. Downstairs, a sprawling family room, separate den or office, and a third full bath provide flexible space for guests, work-from-home needs, or multi-generational living. Head back upstairs to the sliding doors that lead to a deck overlooking the pool and 1.5 acres of peaceful, sun-drenched property — perfect for gardening, outdoor play, or simply relaxing in nature. Set in a quiet neighborhood just minutes from the Mid-Hudson Bridge, Route 9W, and all the best of Highland and New Paltz, this home offers exceptional value, privacy, and lifestyle — whether you're searching for a full-time residence or a spacious weekend retreat.

$525,000 - Highland, NY

19 Oak Crest Drive Highland, NY - Blending comfort and style, this thoughtfully refreshed home is ready to welcome you. Major upgrades bring peace of mind, including a 50-year architectural roof (installed 2023) brand new bathrooms and beautiful new flooring throughout, including warm red oak hardwood that elevates the interior. The upstairs features all new carpeting, two fully renovated bathrooms, walk in primary closet, new heat pump and compressor system for efficient heating and cooling with the added option of using oil baseboard on both levels, if preferred. The renovated eat-in kitchen flows seamlessly to a brand-new cedar deck – ideal for morning coffee while enjoying the fenced yard and tranquil wooded backdrop. The perfect setting for private outdoor enjoyment. Additional upgrades include SS appliances (featuring a Bosch dishwasher,) newer (2021) washer and dryer, water softener, UV light, whole-house water filtration and new garage doors. The generator adds further peace of mind when storms roll in. Tucked in a quiet, no-through-traffic neighborhood just 10 minutes from the creative, vibrant energy of New Paltz and the historic charm of Poughkeepsie, this home combines a sense of retreat with convenient access to everything you need. The work has already been done for you - step right into your next chapter! Video avail. Documentation attached to listing for further information. Please note: by no intention of listing agent or seller, kitchen proportions are not entirely accurate due to photographer lens choice.

Highland, New York listings for sale

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