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Highland, NY Homes for Sale under $500,000

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  • /2

    $200,000

    • Land
    • 6.2 Acres
    • $32,258 per Acre

    0 Vineyard Ave Unit 20256184, Highland, NY 12528

    Rare find. 6.2 acres with town water, sewer and gas. 1/2 zoning can have single family, multi family and multiple units.

    Agent Photo

    Danielle Carlson-murphy

    Start Home Smart, Inc.

    (845) 584-7833

    0 Vineyard Ave Unit 20256184, Highland, NY 12528
  • /3

    $469,000

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    224 Vineyard Ave, Highland, NY 12528

    Ready-To-Build 3-Bedroom Home with Mountain Views - Prime Location Near Town This won't last long ready to-built. Still time to customize the floor plan, pick colors, countertops and more. 3-bedroom, 2-bathroom home on a scenic .24-acre lot with stunning Illinois Mountain views. Perfectly situated just minutes from town, you'll enjoy close proximity to restaurants, the train station, wineries,

    Agent Photo

    Danielle Carlson-murphy

    Start Home Smart, Inc.

    (845) 581-7956

    224 Vineyard Ave, Highland, NY 12528
  • /9

    $249,000

    • Land
    • 6.38 Acres
    • $39,028 per Acre

    0 Browning Blvd Unit 27248900, Highland, NY 12719

    Escape to the beauty of lake living with this stunning 6.38-acre property in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

    Cathy Nation Premier Land Hub

    0 Browning Blvd Unit 27248900, Highland, NY 12719
  • /23

    $340,000

    • 2 Beds
    • 1 Bath
    • 1,117 Sq Ft

    128 Vineyard Ave Unit 202, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 1,117-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 202, Highland, NY 12528
  • /6

    $227,000

    • Land
    • 3.9 Acres
    • $58,205 per Acre

    5 Elbow Ln, Highland, NY 12528

    Seasonal Hudson River Views. This lot was approved for an in ground septic system and engineered for a 4 bedroom home in 2011. Will need to be updated. Virgin land! Beautiful building lot in fairly new subdivision with underground electric service. Only minutes to the Mid Hudson Bridge, The Walkway Over the Hudson and many other attractions. Easy access to train and plane. Current new homes in

    Elizabeth Decker Hudson Dwellings Realty

    5 Elbow Ln, Highland, NY 12528
  • /23

    $355,000

    • 2 Beds
    • 1 Bath
    • 1,230 Sq Ft

    128 Vineyard Ave Unit 102, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 1,230-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 102, Highland, NY 12528
  • /14

    $399,000

    • Land
    • 7.47 Acres
    • $53,414 per Acre

    0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719

    Gorgeous lakefront property with possible owner financing! Build your dream waterfront retreat. This rare, southern-exposure lakefront property offers the ultimate canvas for your dream home, tucked within a private gated community. Spanning over 7.47 extraordinary acres along the shores of a pristine glacial lake, this secluded retreat is designed for those who value privacy, nature, and

    Dawn Payne Payne Team LLC

    0 York Lake Estates Rd Unit KEY987214, Highland, NY 12719
  • /21

    $355,000

    • 2 Beds
    • 1 Bath
    • 1,234 Sq Ft

    128 Vineyard Ave Unit 110, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 1,234-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 110, Highland, NY 12528
  • /10

    $300,000

    • 4 Beds
    • 2 Baths
    • 1,450 Sq Ft

    87 Vineyard Ave, Highland, NY 12528

    Village of Highland two family w/two bedroom units. Hardwood floors throughout. Separate utilities with natural gas for heat & hot water. Centrally located with easy access to village amenities, commuter routes & Mid-Hudson Bridge. Attractively low taxes. Ideal for investor or owner occupant.

    Dan Axtmann BHHS Hudson Valley Properties

    87 Vineyard Ave, Highland, NY 12528
  • /13

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 207, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 207, Highland, NY 12528
  • /13

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 208, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 208, Highland, NY 12528
  • /13

    $500,000

    $195K PRICE DROP
    • Land
    • 11.5 Acres
    • $43,478 per Acre

    TBD Rt 9w, Highland, NY 12528

    Attention Investors! 11.5 acres located just minutes from the Mid-Hudson Bridge in desirable Highland, NY ready for developing. Ideally located on a high traffic state highway with over 1,000 feet of road frontage and tons of visibility. This lot sits directly across the highway from the future river front development named 'The Hudson Valley Wine Village' which is proposed to have 800 new

    John Quinn Quinn Realty Group Inc.

    TBD Rt 9w, Highland, NY 12528
  • /31

    $500,000

    • Land
    • 97.1 Acres
    • $5,149 per Acre

    TBD Lily Lake Rd, Highland, NY 12528

    A rare opportunity to own a breathtaking 97-acre property featuring the very lake that gives Lily Lake Road its name. Tucked away in the beautiful countryside of Highland, New York, this one-of-a-kind parcel offers unmatched privacy, natural beauty, and endless potential for your dream retreat or legacy estate. At the heart of the property lies Lily Lake — a serene, private body of water

    John Quinn Quinn Realty Group Inc.

    TBD Lily Lake Rd, Highland, NY 12528
  • /17

    $370,000

    • 4 Beds
    • 2 Baths

    81 Kisor Rd, Highland, NY 12528

    Welcome to 81 Kisor Rd in the heart of Highland, NY — a strong investment opportunity featuring two occupied rental units with leases secured through April 2027, offering immediate and stable income for the next owner, while also presenting excellent future potential for an owner-occupier once the current leases expire.This two-family property consists of a spacious 3-bedroom apartment on the

    Dan Gilbert Brick and Mortar RE LLC

    81 Kisor Rd, Highland, NY 12528
  • /14

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 201, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 201, Highland, NY 12528
  • /10

    $249,000

    • Land
    • 6.38 Acres
    • $39,028 per Acre

    0 Browning Blvd Unit KEY997085, Highland, NY 12719

    Escape to the beauty of lake living with this stunning 6.38-acre property in the private gated community of York Lake Shores. Enjoy boating, sailing, swimming, and fishing on the pristine lake while surrounded by peace and nature. Ideally located just two hours from New York City and under 20 minutes to the Metro-North train, this property offers the perfect balance of seclusion and convenience.

    Dawn Payne Payne Team LLC

    0 Browning Blvd Unit KEY997085, Highland, NY 12719
  • /25

    $375,000

    $22K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,661 Sq Ft

    7 River Rd, Highland, NY 12528

    UNIQUE FLOOR PLAN in this updated eyebrow colonial creates an ideal setup for a bed-and-breakfast use of this property. Each bedroom features it's own full bath, offering comfort and privacy for all. The spacious living area includes a formal dining room and updated kitchen. A first- floor bedroom and convenient laundry add to the home's flexibility. Enjoy a short walk to the Hamlet of Highland

    Elizabeth Decker Hudson Dwellings Realty

    7 River Rd, Highland, NY 12528
  • /13

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 206, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 206, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 106, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 106, Highland, NY 12528
  • /31

    $429,900

    $20K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,382 Sq Ft

    52 Phillips Ave, Highland, NY 12528

    This one checks all the boxes! Welcome to 52 Phillips Ave where you have the best a home can offer having been recently renovated, inside and out and with direct access to the Hudson Valley Rail Trial. It is close to downtown amenities and just two minutes to the Mid-Hudson Bridge. This home was lovingly renovated to include modern updates while maintaining charm throughout. The main level

    Amy Hawks Berardi Realty

    52 Phillips Ave, Highland, NY 12528
  • /15

    $425,000

    • 3 Beds
    • 2 Baths
    • 2,100 Sq Ft

    60 Mayer Dr, Highland, NY 12528

    Beautifully situated in a lovely Highland neighborhood, this raised ranch home offers warmth, space, and incredible potential in one of the Hudson Valley’s most desirable commuter locations. Featuring hardwood floors, an updated kitchen with stainless steel appliances and modern cabinetry, comfortable bedrooms, and bright living spaces filled with natural light, the home provides a flexible

    Nicholas Cuomo Keller Williams Realty

    60 Mayer Dr, Highland, NY 12528
  • /13

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 205, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 205, Highland, NY 12528
  • /42

    $499,000

    • 3 Beds
    • 2 Baths
    • 1,862 Sq Ft

    85 Bellevue Rd, Highland, NY 12528

    Nestled on a quiet road in the heart of the Hudson Valley, this well maintained raised ranch at 85 Bellevue Road in Highland offers comfortable living with a spacious layout and peaceful surroundings. Built in 1987, the home features approximately 1,800+ square feet of living space with 3 bedrooms and 2 full bathrooms on over a half acre of property. The main level offers a bright and inviting

    Geraldine Gaudioso Century 21 Alliance Rlty Group

    85 Bellevue Rd, Highland, NY 12528
  • /33

    $485,000

    $65K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,640 Sq Ft

    98 North Rd, Highland, NY 12528

    This charming 1900 farmhouse in Highland, New York, offers a comfortable and spacious living space with original wide custom moldings and beautiful oak hardwood flooring. Enjoy the beautiful sunlight in the fully finished sunroom. The kitchen is open with plenty of counter space and new appliances. Large dining area. The primary bedroom is on the first floor with windows facing three sides. enjoy

    Dawn Passante Coldwell Banker Village GreenN

    98 North Rd, Highland, NY 12528
  • /32

    $485,000

    $114K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,510 Sq Ft

    340 Vineyard Ave, Highland, NY 12528

    Step back in time with this spacious Victorian home full of original charm and character. Nestled on 41.10 acres of scenic land with mountain views. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restoration or creative retreat spaces. Inside you will find hardwood floors, birch cabinets with amazing stainless retro

    Ronnie Rebis Grist Mill Real Estate

    340 Vineyard Ave, Highland, NY 12528
  • /23

    $340,000

    • 2 Beds
    • 1 Bath
    • 1,116 Sq Ft

    128 Vineyard Ave Unit 209, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 1116-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 209, Highland, NY 12528
  • /40

    $450,000

    • 4 Beds
    • 2.5 Baths
    • 2,260 Sq Ft

    573 Plutarch Rd, Highland, NY 12528

    *Multiple offers - highest and best by 6/3 at 5pm* A rare opportunity awaits at this striking contemporary estate, nestled on over 11 acres of absolute privacy within the highly desirable New Paltz School District. Situated on a quiet country road, this four-bedroom, two and a half bathroom home is a true diamond in the rough, offering the perfect canvas for a buyer with the vision and means to

    Kristen Zigouras eXp Realty

    573 Plutarch Rd, Highland, NY 12528
  • /12

    $400,000

    • 5 Beds
    • 3 Baths
    • 2,700 Sq Ft

    19-21 Church St, Highland, NY 12528

    Village of Highland three family comprised of (2) two bedroom units and (1) one bedroom unit. Spacious apartments with well proportioned rooms. Natural gas for heat & hot water. Separate utilities & off street parking. Centrally located with easy access to village amenities, Route 9W & Mid-Hudson Bridge.

    Dan Axtmann BHHS Hudson Valley Properties

    19-21 Church St, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 104, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 104, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 108, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 108, Highland, NY 12528
  • /40

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    104 New Paltz Rd, Highland, NY 12528

    Convenient oversized raised ranch with spacious rooms. The main floor features a full eat-in kitchen with beautiful retro appliances and a living room with a large bay window that allows plenty of light to flow inside. There’s a spacious dining room that’s perfect for entertaining and 3 bedrooms for all your needs. The primary bedroom has its own full bath. The lower level is inviting with a

    Dawn Passante Coldwell Banker Village Green

    104 New Paltz Rd, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 101, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 101, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 103, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 103, Highland, NY 12528
  • /14

    $270,000

    • 1 Bed
    • 1 Bath
    • 803 Sq Ft

    128 Vineyard Ave Unit 107, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 803-square-foot first-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The custom

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 107, Highland, NY 12528
  • /24

    $465,000

    • 3 Beds
    • 2 Baths
    • 1,820 Sq Ft

    11 Cuomo Dr, Highland, NY 12528

    Timeless Charm: Authentic Log Ranch Home LivingEmbrace the perfect blend of rustic warmth and modern convenience in this captivating three-bedroom, two-full-bath log ranch home. Nestled on over an acre of beautifully manicured land, this property offers a peaceful retreat without sacrificing accessibility. The heart of the home features a spectacular double-faced stone fireplace, seamlessly

    JoAnn Ellis Summerset Realty

    11 Cuomo Dr, Highland, NY 12528
  • /8

    $450,000

    • Land
    • 2.04 Acres
    • $220,588 per Acre

    0 Lake View Dr Unit KEY857198, Highland, NY 12743

    Discover your dream retreat on this stunning lakefront vacant land located on Highland Lake, one of Sullivan County's premier motorboat lakes. With an established driveway and dock already in place, this property offers easy access to endless recreational opportunities, from fishing to boating to everything in between. Imagine building your perfect getaway, surrounded by breathtaking views and

    Dawn Payne Payne Team LLC

    0 Lake View Dr Unit KEY857198, Highland, NY 12743
  • /15

    $399,999

    • 4 Beds
    • 3 Baths
    • 2,104 Sq Ft

    6 Bell Dr, Highland, NY 12528

    Great investment opportunity in the heart of downtown Highland. This well-maintained 2-family property features one fully renovated unit and one unit with value-add potential—ideal for investors or owner-occupants looking to increase rents over time. Situated on a generous .75-acre lot on a quiet street, the property offers plenty of space to entertain, relax, and enjoy the surrounding setting.

    Joseph Sala McGrath Realty Inc

    6 Bell Dr, Highland, NY 12528
  • /13

    $265,000

    • 1 Bed
    • 1 Bath
    • 730 Sq Ft

    128 Vineyard Ave Unit 204, Highland, NY 12528

    Welcome to Highbridge Crossing, a modern river-town condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, N.Y. This 730-square-foot second-floor residence blends smart design, comfort and easy outdoor living--ideal for low-maintenance living without sacrificing style. The open-concept layout features large windows and seamless flow throughout. The

    Andrea Babcock Onyx Property Management LLC

    128 Vineyard Ave Unit 204, Highland, NY 12528
  • /13

    $500,000

    $195K PRICE DROP
    • Land
    • 11.5 Acres
    • $43,478 per Acre

    TBD Route 9w, Highland, NY 12528

    Attention Investors! 11.5 acres located just minutes from the Mid-Hudson Bridge in desirable Highland, NY ready for developing. Ideally located on a high traffic state highway with over 1,000 feet of road frontage and tons of visibility. This lot sits directly across the highway from the future river front development named "The Hudson Valley Wine Village" which is proposed to have 800 new

    John Quinn Quinn Realty Group Inc

    TBD Route 9w, Highland, NY 12528
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