Homes for Sale near Highland Middle School

• 

  

  

  /19

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,707 Sq Ft

  38 Roxanne Blvd, Highland, NY 12528

  A/O 9/27/2025 (no available showings at this time) Opportunity knocks with this three bedroom, two bathroom split ranch situated on one acre, on a quiet cul-de-sac road. Beautiful hardwood floors and desirable floor plan. Bring your vision as this home is full of potential! The lower level walkout area of the home is finished with a full bathroom. Conveniently located just minutes to the Village

  

  Amy Hawks

  Berardi Realty

  (845) 203-3694

  38 Roxanne Blvd, Highland, NY 12528
• 

  Explore Highland Middle School

• 

  

  /2

  $185,000

  • Land
  • 0.24 Acre
  • $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.

  

  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.

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 584-7833

  0 Vineyard Ave Unit 20256184, Highland, NY 12528
• 

  

  

  /52

  $3,950,000

  • 9 Beds
  • 12 Baths
  • 10,500 Sq Ft

  9 Chambers Rd, West Park, NY 12493

  A great legacy meets true luxury: Hudson Shore Estate, formerly home to one of Eleanor Roosevelt's early passion projects, a pioneering vocational school for women, has now been masterfully restored to its former glory and offers the perfect setting for a multi-generational family compound. A unique example of Arts & Craft design amongst its peer group of renowned Hudson River mansions, the

  

  Hayes Clement

  Compass Greater New York, LLC

  (845) 712-3840

  9 Chambers Rd, West Park, NY 12493
• 

  

  

  /25

  $365,000

  • 2 Beds
  • 2 Baths
  • 1,300 Sq Ft

  241 Upper Rd N, Highland, NY 12528

  Welcome to 241 Upper North Road - Where Comfort Meets Convenience! This beautifully maintained modern double-wide mobile home offers the charm and functionality of a modular home, nestled on a spacious 0.78-acre lot. With an inviting open floor plan, this residence features 2 bedrooms, a versatile den with a cozy gas fireplace, and 2 full bathrooms, offering ample space for both relaxation and

  

  Isabel Alves

  RE/MAX Town & Country

  (845) 493-3607

  241 Upper Rd N, 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 TownThis 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,

  

  Danielle Carlson-murphy

  Start Home Smart, Inc.

  (845) 581-7956

  224 Vineyard Ave, Highland, NY 12528
• 

  

  /65

  $1,250,000

  • 3 Beds
  • 3.5 Baths
  • 4,572 Sq Ft

  74 Bellevue Rd, Highland, NY 12528

  Hudson River Views! This inviting home combines comfort, character, and convenience with a dramatic two-story foyer and open floor plan. Enjoy a cozy living room with a gas fireplace, formal dining area overlooking the river, and a kitchen with custom cherry cabinets, granite counters, and Jenn Air cooktop. A flexible room with French doors makes a great office or fourth bedroom. Bathroom and

  Hollis Dukler Coldwell Banker Village GreenN

  74 Bellevue Rd, Highland, NY 12528
• 

  

  /35

  $4,600,000

  • 16 Beds
  • 10.5 Baths
  • 11,160 Sq Ft

  35 Washington Lake Rd, Highland, NY 12792

  Amazing One-of-a-kind Lakefront Home! This magnificent 11,000+ SF home features massive 2 story great room w/ stone fireplace, floating staircase & spiral staircase, commercial kitchen w/ walk in freezer & refrigerator, huge dining area/ game room/ wet bar. The home also offers 16 bedrooms, 10.5 baths, theater room, office, enclosed porch, huge patio featuring outdoor kitchen w/ wood fired pizza

  Jill Barnes Cabins & Canoes Real Estate

  35 Washington Lake Rd, Highland, NY 12792
• 

  

  /19

  $138,500

  • 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
• 

  

  /7

  $219,900

  • 2 Beds
  • 1 Bath
  • 1,096 Sq Ft

  18 Hillside Place, Highland, NY 12528

  Cozy two bedroom home within walking distance to the village shops and restaurants in Highland. Great location on a dead end street and great opportunity for the saavy buyer. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer

  Brian Smith River Realty Services, Inc.

  18 Hillside Place, Highland, NY 12528
• 

  

  /6

  $44,000

  • Land
  • 2.9 Acres
  • $15,172 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  This property is located in a desirable area that offers a balance of privacy and convenient access to key attractions in the Hudson Valley. Its location is situated just a few miles from the heart of downtown New Paltz and with Kingston also close by, you'll have easy access to all the vibrant shops, restaurants, and cultural scene. The site is also 6 miles from the Mid-Hudson Bridge and the

  Dominick Martorana Century 21 Alliance Rlty Group

  TBD Hawleys Corners Rd, Highland, NY 12528
• 

  

  /3

  $4,400,000

  • Land
  • 73.7 Acres
  • $59,701 per Acre

  00 Vineyard Ave, Highland, NY 12528

  Multi family property consisting of R-1/4, R-1/2 and R-1 zoning. Totaling 73 plus acres with two access points along Rte 44, Vineyard Avenue, in the Town of Lloyd, Ulster County, NY. One on the South end of the property with 150 feet of frontage along Vineyard Avenue and one on the North end of the property with 50 feet of frontage along Vineyard Avenue. Property slopes gently upward from road

  Robert Vitanza Rand Commercial

  00 Vineyard Ave, Highland, NY 12528
• 

  

  /13

  $500,000

  • 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
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  /24

  $130,000

  • 2 Beds
  • 1.5 Baths
  • 952 Sq Ft

  1069 Route 44 55, Clintondale, NY 12515

  Step into the potential of this 952 sq ft railroad-style home, featuring 2 cozy bedrooms and 1.5 bathroom. This classic layout, known for its linear flow and vintage character, offers a unique opportunity for those looking to restore or reimagine a timeless space.While the home needs renovation, its solid structure and charming original details provide the perfect canvas for

  John Quinn Quinn Realty Group Inc.

  1069 Route 44 55, Clintondale, NY 12515
• 

  

  /50

  $990,000

  • Land
  • 215.12 Acres
  • $4,602 per Acre

  00 Rt 44 55, Clintondale, NY 12515

  This is a hard-to-find large acreage consisting of four parcels located on both sides of Route 44/55 in the hamlet of Clintondale. Being sold as one sale leaves the opportunity for investors and builders looking for their next project, or the potential for a single or multi family homestead. You can keep it all for yourself or sell off what you don't need. The largest parcel is approximately

  Clint Carlson WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

  00 Rt 44 55, Clintondale, NY 12515
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  /8

  $60,000

  • Land
  • 0.48 Acre
  • $125,000 per Acre

  0 Route 9w Unit KEYH6287477, Lloyd, NY 12528

  Centrally located .48 acre lot on Rt. 9W just outside the quaint village of Highland. Lot is zoned GB and is situated next to a local bank, major fast food establishments, gas stations and assorted businesses.

  John Quinn Quinn Realty Group Inc

  0 Route 9w Unit KEYH6287477, Lloyd, NY 12528
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  /32

  $450,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 1.5 Baths
  • 3,140 Sq Ft

  668 U S 44, Highland, NY 12528

  With its over 100-year-old history, this home has only changed hands once before, a testament to its enduring appeal and the kind of place that's been lovingly maintained for generations.Set on 1.2 scenic acres, this charming three-story, 4-bedroom, 1.5-bath Colonial offers classic style and beautiful surroundings. A wraparound paved driveway with river stone posts leads to a two-car garage,

  Heather Hughes Hudson Dwellings Realty

  668 U S 44, Highland, NY 12528
• 

  

  /19

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  8 Sunny Brook Cir, Highland, NY 12528

  Tastefully updated 2 bedroom, 1.5 bath townhouse features renovated kitchen w/modern styling includes stainless appliances, pantry & open shelving. Spacious living room leads upstairs to primary bedroom w/walk-in closet, well proportioned second bedroom and office alcove. Two renovated bathrooms, new flooring & new a/c compressor. Large fenced bluestone patio for outdoor living enjoyment. Complex

  Dan Axtmann BHHS Hudson Valley Properties

  8 Sunny Brook Cir, Highland, NY 12528
• 

  

  /18

  $349,000

  • 2 Beds
  • 2 Baths
  • 992 Sq Ft

  451 New Paltz Rd, Highland, NY 12528

  INVESTMENT PROPERTYThis 2 family property is conveniently located in Highland. Less than 10 minutes to the Village of New Paltz, and 15 minutes to the Mid-Hudson bridge.The location is just steps away from the Hudson Valley Rail Trail, which is a 7 mile paved trail from the Walkway over the Hudson to New Paltz.Each unit is a one bedroom one bath apartment. Private parking lot has

  Jaynie Aristeo Ridgeline Realty

  451 New Paltz Rd, Highland, NY 12528
• 

  

  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 207, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 207, 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
• 

  

  /25

  $397,000

  • 3 Beds
  • 3 Baths
  • 1,661 Sq Ft

  7 River Rd, Highland, NY 12528

  Charming 1830s Eyebrow Colonial. Spacious Living Area with formal Dining Room and updated Kitchen. Laundry and one bedroom on first floor. 3 bedrooms, 3 Bathrooms. Walk to the Hamlet of Highland and the Highland Landing Park on the mighty Hudson River. Many restaurants and shops nearby as well as the Hudson Vallely Rail Trail. Soothing sounds from babbling Twaalfskill stream across the street.

  Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, Highland, NY 12528
• 

  

  /23

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,296 Sq Ft

  67 Picnic Woods Rd, Clintondale, NY 12515

  Nestled on peaceful Picnic Woods Road, this charming three-bedroom, two-bathroom home offers 1,296 square feet of thoughtfully designed living space and energy efficiency. The well-maintained property features an inviting open-concept layout where the spacious living room flows seamlessly into the kitchen and dining area. Step outside to the expansive deck, overlooking a large, level backyard and

  Anna Barcone Berkshire Hathaway Homeservice

  67 Picnic Woods Rd, Clintondale, NY 12515
• 

  

  /7

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft

  29 Oakes Rd, Highland, NY 12528

  An exceptional and rare opportunity to own a piece of the Hudson Riverfront between two of the region’s most iconic landmarks, the Mid-Hudson Bridge and the Walkway Over the Hudson. Located on the Highland side, presenting a blend of natural beauty and historic charm. At the heart of the property is a c.1840s two bedroom, one bath home, offering timeless character and panoramic views of the

  Anthony DeGelormo Century 21 Alliance Rlty Group

  29 Oakes Rd, Highland, NY 12528
• 

  

  /22

  $2,100,000

  • Land
  • 70.5 Acres
  • $29,787 per Acre

  243 Vineyard Ave Unit 251, Highland, NY 12528

  Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

  John Quinn Quinn Realty Group Inc

  243 Vineyard Ave Unit 251, Highland, NY 12528
• 

  

  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 206, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 206, Highland, NY 12528
• 

  

  /47

  $389,000

  • 4 Beds
  • 1.5 Baths
  • 1,458 Sq Ft

  22 Washington Ave, Highland, NY 12528

  Lovely home within walking distance to center Village Highland & Walkway Over the Hudson Bridge. 3BR/1.5BA home located at the end of quiet Cul de Sac with private backyard. Beautiful front porch up front and a rustic 2 story barn over looking private backyard with stream and forest. Enjoy the coziness and charm of this lovingly cared for home built in 1840. Detached 2 car garage with small paved

  CAROL MC RITCHIE Thomas Zengen

  22 Washington Ave, Highland, NY 12528
• 

  

  /17

  $50,000

  • Land
  • 1.36 Acres
  • $36,765 per Acre

  0 White St, Highland, NY 12528

  Looking for the perfect lot for your new home? This lovely 1.36-acre wooded lot is situated on a gentle rise above an established community in historic Highland. It offers the best of both worlds; peace, privacy, and appealing elevated views, with convenient access to all amenities and the security of having neighbors nearby. Easy access to the Walkway Over the Hudson, Empire State Rail

  Carolyn Michelle KW MidHudson

  0 White St, Highland, NY 12528
• 

  

  /12

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 104, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 104, Highland, NY 12528
• 

  

  /26

  $549,000

  • 4 Beds
  • 2 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
• 

  

  /31

  $399,000

  • 3 Beds
  • 2.5 Baths
  • 1,104 Sq Ft

  534 U S 44, Highland, NY 12528

  Set high on a hill with mountain views, this fully remodeled home is turn-key and ready to enjoy. The open floor plan connects the kitchen, dining, and living areas—ideal for both everyday living and entertaining. The first floor also features a convenient half bath and laundry room, while upstairs offers three bedrooms and two baths, including a primary bedroom with ensuite. A full attic

  Sally Sprogis Four Seasons Sotheby's Int'l R

  534 U S 44, Highland, NY 12528
• 

  

  /31

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft

  10 Carly Dr, Highland, NY 12528

  Discover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained 4-bedroom, 2-bathroom single-level home, tucked away in a peaceful cul-de-sac in sought-after Highland, NY. Sitting on a full acre, this property offers endless possibilities space to entertain, relax, and enjoy outdoor living. Cool off all summer long in the above-ground pool, or take in the privacy

  Megan Krusen eXp Realty

  10 Carly Dr, Highland, NY 12528
• 

  

  /5

  $125,000

  • Land
  • 0.9 Acre
  • $138,889 per Acre

  120 Floyd Ackert Rd, Esopus, NY 12429

  Bring your plans! Here is your blank canvas for the home of your dreams. Located a short distance from Route 9W in West Park for easy commuting to Kingston or south to Highland and Metro North. Property is located on .9 acres with lots road frontage.

  Dawn Passante Coldwell Banker Village Green

  120 Floyd Ackert Rd, Esopus, NY 12429
• 

  

  /50

  $1,250,000

  • 14 Beds
  • 9 Baths
  • 6,406 Sq Ft

  346 Crescent Ave, Highland, NY 12528

  The Historic “Clintondale Elixir Spring House”A timeless treasure, the historic Clintondale Elixir Spring House—originally built in 1790—is a rare and remarkable offering to the market. Encompassing over 6,400 square feet of living space, this distinguished residence invites you to create your forever home amid rich character and architectural beauty.Step through the welcoming

  Artur Galustyan Century 21 Alliance Rlty Group

  346 Crescent Ave, Highland, NY 12528
• 

  

  /24

  $565,000

  • 3 Beds
  • 1 Bath
  • 2,086 Sq Ft

  269 Orchard Rd, Highland, NY 12528

  Nestled among scenic orchards is this beautiful, updated nineteenth century farm house situated on almost 20 acres of beautiful pasture land and woods. This charming 3 bedroom home has a lovely full bath and plenty of living space for both humans and horses alike. The current owner keeps her horses on the property which is equipped with 2 run-in sheds and 7 shed row stalls which all have power

  Daniel Balassone VYLLA Home

  269 Orchard Rd, Highland, NY 12528
• 

  

  /6

  $249,000

  • Land
  • 4 Acres
  • $62,250 per Acre

  27 Picnic Woods Rd, Clintondale, NY 12515

  Absolutely beautiful 4 acre Board of Health Approved building lot that's ready for your dream home! This wonderful property features a level building site with it's own gorgeous pond views from the front, and another water view from the rear of the proposed homesite! You'll love the rural feel and privacy, yet will have the convenience of close proximity to Rte 9W. Maps are available--you'll love

  Diane Crittenden Century 21 Alliance Realty Grp

  27 Picnic Woods Rd, Clintondale, NY 12515
• 

  

  /15

  $399,000

  • Land
  • 8.7 Acres
  • $45,862 per Acre

  3748 Us Highway 9w, Highland, NY 12528

  8.7 acres of untouched land just south of the Mid Hudson Bridge. Current plan was to build a church. Site plan and survey attached with the docs. Property is next to Walgreens and will allow many uses. Zoning Examples to be confirmed by buyer agent, Light Business Use, Convenience store, day care adult or child, funeral home, office, skating rink, bowling alley, Vet office, warehouse, park,

  Jason Madison eXp Realty

  3748 Us Highway 9w, Highland, NY 12528
• 

  

  /4

  $150,000

  • Land
  • 1.5 Acres
  • $100,000 per Acre

  0 Haviland Rd Unit KEY899872, Highland, NY 12528

  Discover the potential of this rare 1.5 acre non-conforming lot with breathtaking views of the Hudson River. This vacant parcel offers the perfect canvas for your dream build. Whether you envision a serene weekend retreat or a year round residence immersed in natures beauty. This property provides a gloriuos vantage point for sunrise coffee, sunset gatherings and endless water views. While the

  Anthony DeGelormo Century 21 Alliance Rlty Group

  0 Haviland Rd Unit KEY899872, Highland, NY 12528
• 

  

  /6

  $275,000

  • Land
  • 6.2 Acres
  • $44,355 per Acre

  9 Lumen Ln, Highland, NY 12528

  Prime Development Opportunity. 6.2 acres of strategically located vacant land in Highland, NY. Zoned for General Business and packed with potential. This plot is situated just off highly traveled Route 9W. The parcel offers both visibility and accessibility, ideal for a wide range of commercial or mixed-use developments.This property has an array of permitted uses, including retail,

  Theodore Chazkel Four Seasons Sotheby's Int'l R

  9 Lumen Ln, Highland, NY 12528
• 

  

  /30

  $500,000

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

  0 Lily Lake Rd Unit KEY908782, Lloyd, 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

  0 Lily Lake Rd Unit KEY908782, Lloyd, NY 12528

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