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Highland, NY Homes for Sale under $400,000

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  • /8

    $195,000

    • Land
    • 22.3 Acres
    • $8,744 per Acre

    0 Crawford Rd Unit KEY821449, Highland, NY 12528

    Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan, Barryville, Narrowsburg and the Delaware River.

    Agent Photo

    Rosemarie DeCristofaro

    Callicoon Real Estate LLC

    (845) 681-6170

    0 Crawford Rd Unit KEY821449, Highland, NY 12528
  • /2

    $185,000

    • Land
    • 10,454 Sq Ft
    • $770,833 per Acre

    224 Vineyard Ave, Highland, NY 12528

    Recent home demolished and removed. .24 acre lot with town water and sewer (Natural gas on the street but not to the lot). 1.5 miles to the Hamlet of Highland. Ask us about our custom home affordability program.

    Agent Photo

    Danielle Carlson-murphy

    Start Home Smart, Inc.

    (845) 713-8132

    224 Vineyard Ave, Highland, NY 12528
  • /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
  • /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
  • /19

    $138,500

    $20K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,096 Sq Ft

    18 Hillside Place, Highland, NY 12528

    Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our bpo/tax describe the property as a SFR (ranch) built in 1950. It has a GLA of approx. 1096 and has 2 bedrooms and 1bath,

    Christopher Rose Listing by REALHome Services & Solutions

    18 Hillside Place, 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
  • /24

    $179,000

    Pre-Foreclosure
    • 4 Beds
    • 1.5 Baths
    • 1,404 Sq Ft

    687 Whitley Ln, Highland, NY 12528

    Investor opportunity in the Town of Lloyd! Situated on 1.4 private acres, this 4-bedroom home offers tremendous potential for renovation, customization, or resale. The property is in need of significant rehabilitation and is ready for its next owner to bring it back to life. Features include a full basement, attached garage, and a desirable location just minutes from New Paltz, the Mid-Hudson

    Philip Szumlaski Keller Williams Realty

    687 Whitley Ln, 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
  • /37

    $335,000

    • 2 Beds
    • 1.5 Baths
    • 1,270 Sq Ft

    107 Sterling Place, Highland, NY 12528

    Investment Opportunity – Desirable Bridgeview Townhome Community Come join the wonderful Bridgeview community—Tucked away for privacy, yet conveniently located with a small shopping plaza out front and scenic wooded trails in the back, Bridgeview offers both comfort and convenience. This well-maintained home features recent updates, including brand-new flooring throughout, a 7 year roof, a new

    JULIA MULLEN K. Fortuna Realty, Inc.

    107 Sterling Place, 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
  • /24

    $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
  • /30

    $165,000

    $14K PRICE DROP
    • Land
    • 3.02 Acres
    • $54,636 per Acre

    44 Vineyard Ave, Highland, NY 12528

    Gorgeous wooded 3 acre flag lot with view potential to the east and south. Great commuter location minutes from the NYC trains and the NYS Thruway. Driveway has been roughed in for you and the septic approval will need to be redone. Power and cable will be brought in around 350' by the seller. Excellent location for a full time or weekend home. Old stone walls line the southern and western edges.

    Bruce Stalnaker Coldwell Banker Village GreenN

    44 Vineyard Ave, Highland, NY 12528
  • /6

    $199,000

    • Land
    • 11 Acres
    • $18,091 per Acre

    TBD Hawleys Corners Rd, Highland, NY 12528

    11 acres offering privacy and potential. The land is ideal for building a secluded estate or your own nature retreat. Located on a country road, yet close to Route 299 leading to the NYS Thruway. The Mid-Hudson Bridge is only 5 miles away. The parcels break down as follows: Parcel 1: 3.5 acres, Parcel 2: 4 acres, and Parcel 3: 3.7 acres. Key features include a peaceful rural setting with minimal

    Dawn Passante Coldwell Banker Village Green

    TBD Hawleys Corners Rd, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /20

    $175,000

    • 4 Beds
    • 3 Baths
    • 2,962 Sq Ft

    25 Phillips Ave, Highland, NY 12528

    Opportunity awaits at 25 Phillips Avenue in the heart of Highland! Situated on a spacious and private lot surrounded by mature trees, this 3-family property offers endless potential for investors, contractors, or buyers looking to restore and customize a large multi-unit home in a desirable Ulster County location. Offering approximately 2,962 square feet, the property features expansive living

    Ronald Green KW MidHudson

    25 Phillips Ave, Highland, NY 12528
  • /15

    $175,000

    • Land
    • 5.84 Acres
    • $29,966 per Acre

    0 Crawford Rd Unit KEY983986, Highland, NY 12528

    Escape to the peace and beauty of the Sullivan County Catskills with this lovely 5.8-acre parcel on Crawford Rd in the Town of Highland. Partially cleared and very private, this property offers the perfect setting to build your dream home in the country. Imagine relaxing on your future front porch or back deck while watching eagles soar overhead, enjoying star-filled skies, and taking in the

    Dominick Tufano RE/MAX Benchmark Realty Group

    0 Crawford Rd Unit KEY983986, Highland, NY 12528
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