Homes for Sale near Highland Middle School

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  /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
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  Explore Highland Middle School

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  /27

  $585,000

  • 3 Beds
  • 2 Baths
  • 2,386 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  Spacious, secluded and close to New Paltz: This roomy ranch features key technical updates while retaining its bright 1970s vibe. Privately set at the end of a long driveway flanked on each side by stacked-bluestone walls, the house sits at the center of the historic Stonewall Farm on its own 19 wooded acres. Entered through a pergola-topped courtyard into a symmetrical blue-stoned foyer

  

  Hayes Clement

  Compass Greater New York, LLC

  (845) 327-2488

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /34

  $495,000

  • 5 Beds
  • 4 Baths
  • 2,366 Sq Ft

  258 Martin Ave, Highland, NY 12528

  ACCEPTED OFFER AS OF SEPT 2, 2025. INSPECTIONS COMPLETE. Major space meets major opportunity: This versatile 2-family home nestled on 2 sunny acres offers privacy plus big potential for comfortable living and extra income. Perfectly adaptable, you can rent both units, live in one while renting the other, or knock down a wall to create a spacious single-family residence. The first unit is an extra

  

  Hayes Clement

  Compass Greater NY, LLC

  (845) 377-4797

  258 Martin Ave, Highland, NY 12528
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  /50

  $1,175,000

  • 7 Beds
  • 5 Baths
  • 5,730 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  ACCEPTED OFFERS ON BOTH HOUSES AS OF SEPT 3, 2025. Welcome to Stonewall Farm, a rare 40-acre retreat featuring not one but TWO architecturally distinctive houses less than two hours from Manhattan and minutes from the New Paltz village center. Privately set at the end of a long driveway flanked on each side by its namesake stacked-bluestone walls, the property features both meadows and woods. The

  

  Hayes Clement

  Compass Greater NY, LLC

  (845) 378-9916

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /29

  $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
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  /14

  $225,000

  • 1 Bed
  • 1 Bath
  • 762 Sq Ft

  534 New Paltz Rd, Highland, NY 12528

  Welcome to 534 New Paltz Rd, Lloyd, NY — a fully renovated and fully furnished home designed for modern living and investment potential. Every detail has been upgraded: New Septic System, New Roof, New Electrical, New plumbing, New Well Pump, New Pressure Tank, New Water Filter, New Water Heater, New Windows, New Heaters, New Doors, New Sump Pump, New Kitchen, New Bathroom Vanity, New Flooring,

  Jonathan Minerick HomeCoin.com

  534 New Paltz Rd, Highland, NY 12528
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  /26

  $479,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  41 Penny Ln, Highland, NY 12528

  Welcome to 41 Penny Lane, this ranch style home is situated on a quiet dead-end road named after the Beatles’ hit song. This 3-bedroom, 2.5-bath, 1,844 sq ft home sits on .52 acres and offers a bonus room that can flex as a 4th bedroom. The open kitchen, updated in 2013, features Brazilian cherry hardwood flooring, and just off it is a massive walk-in pantry with space for a washer/dryer. The

  Jacob Cohen eXp Realty

  41 Penny Ln, Highland, NY 12528
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  /44

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,368 Sq Ft

  123 Vineyard Ave, Highland, NY 12528

  Charming 1900s Home with Character and Versatility! Step into timeless elegance with this beautifully preserved early 20th-century residence, ideally located just a few doors from the vibrant hamlet of Highland. Surrounded by quaint restaurants and shops, this home offers both historic charm and modern convenience. Exterior highlights include a wrap-around covered porch, a classic feature that's

  Dawn Passante Coldwell Banker Village GreenN

  123 Vineyard Ave, Highland, NY 12528
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  /33

  $550,000

  • 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
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  /44

  $899,999

  • 4 Beds
  • 3 Baths
  • 2,600 Sq Ft

  1 Janine Place, Highland, NY 12528

  Just 90 minutes from New York City, this extraordinary turnkey farmhouse has been completely reimagined with meticulous attention to detail, blending timeless Hudson Valley charm with modern luxury living.Step inside to soaring ceilings, wide-plank wood floors, and sunlit spaces that flow effortlessly. At the heart of the home, the custom chef’s kitchen features a gas range, quartz

  Lindsay Stevens eXp Realty

  1 Janine Place, Highland, NY 12528
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  /48

  $539,900 Open Sun 11AM - 2PM

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  62 Clearwater Rd, Highland, NY 12528

  Discover unparalleled privacy in this beautifully maintained home, set on its own serene acreage. Step inside to find a warm and inviting interior featuring hardwood floors throughout the main living areas and plush carpet in the bedrooms for comfort. The living room is anchored by a gorgeous stone fireplace, creating the perfect gathering spot for cozy evenings or entertaining guests. The

  Patricia Lucey Picture It Sold, LLC

  62 Clearwater Rd, Highland, NY 12528
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  /55

  $750,000

  • 3 Beds
  • 3 Baths
  • 2,596 Sq Ft

  1 Jonathan Ct, Highland, NY 12528

  Charming Colonial on 1.39 Acres with Resort-Style AmenitiesWelcome to this beautifully maintained Colonial nestled on 1.39 acres of mature, professionally landscaped grounds. This inviting 3-bedroom, 3 full-bath home offers the perfect blend of timeless charm and modern amenities in a sought-after location near the Mid-Hudson Bridge.Step inside to find a spacious layout featuring

  Danielle Carlson-murphy Start Home Smart, Inc.

  1 Jonathan Ct, Highland, NY 12528
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  /36

  $769,000

  • 4 Beds
  • 2.5 Baths
  • 3,253 Sq Ft

  2 Fieldstone Ct, Highland, NY 12528

  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

  Joseph Brown RE/MAX Real Property Group

  2 Fieldstone Ct, Highland, NY 12528
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  /46

  $525,000

  • 5 Beds
  • 3 Baths
  • 2,024 Sq Ft

  191 Bedell Ave, Highland, NY 12528

  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

  Michael Cahill HomeSmart Homes & Estates

  191 Bedell Ave, Highland, NY 12528
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  /25

  $950,000 Open Sat 2PM - 3PM

  • 10 Baths
  • 8,985 Sq Ft

  10-32 S Roberts Rd, Highland, NY 12528

  Tremendous 27k+ daily commercial & personal car traffic with great street frontage and sign visibility! Significant current net income producing five family home consisting of one bedroom and one full bathroom per unit with a total of around 3,510 sq ft and a two family home with two bedrooms and one full bathroom per unit for a total of around 1,125 sq ft. Both homes are fully occupied and built

  Mi Ryoung Chong HANMI REALTY

  10-32 S Roberts Rd, Highland, NY 12528
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  /29

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft

  39 Sunny Brook Cir, Highland, NY 12528

  Move right in to this bright and refreshing 3 bedroom townhouse with many new upgrades! Brand new flooring throughout, upgraded baths, freshly painted. The kitchen hosts new cabinets, appliances and washer and dryer. Newer oversized central air condenser. Park right outside your home. Beautiful fenced in deck area adds privacy while sitting outside. This Townhouse has everything you’re looking

  Dawn Passante Coldwell Banker Village Green

  39 Sunny Brook Cir, Highland, NY 12528
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  /28

  $315,000

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft

  39 Sunnybrook Cir, Highland, NY 12528

  Move right in to this bright and refreshing 3 bedroom townhouse with many new upgrades! Brand new flooring throughout, upgraded baths, freshly painted. The kitchen hosts new cabinets, appliances and washer and dryer. Newer oversized central air condenser. Park right outside your home. Beautiful fenced in deck area adds privacy while sitting outside. This Townhouse has everything you're looking

  Dawn Passante Coldwell Banker Village GreenN

  39 Sunnybrook Cir, Highland, NY 12528
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  /25

  $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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  /26

  $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
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  /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.

  224 Vineyard Ave, Highland, NY 12528
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  /25

  $375,000

  • 2 Beds
  • 1 Bath
  • 1,050 Sq Ft

  27 Amato Ln, Highland, NY 12528

  Tucked away on a peaceful dead-end road in Highland, this inviting 2-bedroom, 1-bath home offers the perfect blend of charm, updates, and convenience. Whether you're searching for a starter home or a weekend retreat, this property checks all the boxes. The main level welcomes you with an open layout, rustic exposed beams, and a stylishly renovated kitchen featuring sleek soapstone countertops.

  Jacob Cohen eXp Realty

  27 Amato Ln, Highland, NY 12528
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  /6

  $235,000

  • Land
  • 11 Acres
  • $21,364 per Acre

  TBD Hawleys Corners Rd, Highland, NY 12528

  11 acres offering privacy and potential. The land is ideal for building a secluded estate, nature retreat located on a country road yet close to Route 299 leading to NYS Thruway. Mid Hudson Bridge 5 miles away. The parcels break down as follows:Parcel 1: 3.5 acresParcel 2: 4 acresParcel 3: 3.7 acresKey Features:Peaceful rural setting with minimal trafficSurrounded by woods

  Dawn Passante Coldwell Banker Village GreenN

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /50

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,934 Sq Ft

  4 Salk Dr, Highland, NY 12528

  Welcome Home to Comfort, Style & Mountain Views This beautifully renovated split-level home is tucked away in a well-kept neighborhood, offering picturesque mountain views from the front elevation. With flexible living space, modern updates, and inviting outdoor areas, it's ready for you to move right in. Inside, you'll find 3 plus bedrooms (including a flexible bonus space) and two full baths.

  Barbara Korabel FOUR SEASONS REALTY GROUP

  4 Salk Dr, Highland, NY 12528
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  /43

  $419,000

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft

  20 Lauretta Dr, Highland, NY 12528

  Tucked away on a quiet dead-end road, set high with scenic mountain views, this well-kept Raised Ranch is ready for your next chapter in the Hudson Valley. Freshly painted and move-in ready, the home offers 3 bedrooms, 2 bathrooms, a wood-burning fireplace, and a fenced-in backyard. The updated kitchen and spacious, finished lower level—with oversized windows framing the views—provide comfort and

  Peter Ilani BHHS Hudson Valley Properties

  20 Lauretta Dr, Highland, NY 12528
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  /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
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  /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
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  /13

  $329,999

  • 3 Beds
  • 1 Bath
  • 1,372 Sq Ft

  365 Crescent Ave Unit 367, Highland, NY 12528

  Welcome to this charming and beautifully updated home, nestled in a spacious corner lot in a quiet neighborhood. This inviting property offers the perfect blend of country charm and modern conveniences. Step inside to find a warm and welcoming country-style kitchen featuring a cozy coffee bar and breakfast nook, perfect for starting your mornings. The kitchen boasts newer appliances and flows

  Ronnie Rebis Grist Mill Real Estate

  365 Crescent Ave Unit 367, Highland, NY 12528
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  /14

  $265,000

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft

  53 Sunny Brook Cir, Highland, NY 12528

  Welcome to this inviting 2-bedroom end-unit townhouse, perfectly situated in one of Highland's most desirable and affordable communities. Offering both comfort and convenience, this home features a spacious layout, one-level living and a rare sense of privacy. Step outside to your own fenced-in patio — an ideal space for relaxing, gardening, or entertaining. Inside, you'll find two well-sized

  Danielle Bartula Howard Hanna Rand Realty

  53 Sunny Brook Cir, Highland, NY 12528
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  /45

  $325,000

  • 2 Beds
  • 2.5 Baths
  • 1,396 Sq Ft

  87 Sterling Place, Highland, NY 12528

  Welcome to 87 Sterling Place in Highland, located right over the Mid Hudson Bridge. The home features 2 spacious rooms and a loft for a possible office or guest space. There is an attached 1 car garage perfect for sheltering you from the elements outside. Go shopping at Hannafords right next door and pull into your garage to unload the car – no more being out in the rain and snow unloading

  Mark Snyder eXp Realty

  87 Sterling Place, Highland, NY 12528
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  /17

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,816 Sq Ft

  283 Hawleys Corners Rd, Highland, NY 12528

  Nestled on a quiet country road in Highland, this inviting old-style home offers peaceful living on a cleared, and leveled, one-acre lot. Surrounded by nature, the property blends timeless charm with essential exterior modern updates. Including durable new siding, a freshly built deck perfect for relaxing or entertaining, a new roof, and updated gutters—ensuring years of worry-free enjoyment.

  Dawn Passante Coldwell Banker Village GreenN

  283 Hawleys Corners Rd, Highland, NY 12528
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  /8

  $129,000

  • 2 Beds
  • 1 Bath
  • 1,225 Sq Ft

  69 North Rd, Highland, NY 12528

  Yup! It's a bunch of work, but it'll be the cutest house around! This is located just outside of the charming, Historic Hamlet of Highland! Driveway & garage for off street parking. Close to the Mid Hudson Bridge, the Walkway over the Hudson, New Paltz, the Thruway/87, and so much more! Hike the ''Gunks'' and even the Catskills are so close! Love to eat out? There are sweet restaurants nearby!

  Kathy Dawson Howard Hanna Rand Realty

  69 North Rd, Highland, NY 12528
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  /29

  $388,000

  • 3 Beds
  • 1.5 Baths
  • 1,670 Sq Ft

  46 Brescia Blvd, Highland, NY 12528

  Discover your upstate oasis at 46 Brescia Blvd — a beautifully renovated 3-bedroom, 1.5-bath home offering the perfect mix of comfort, style, and indoor-outdoor living in the heart of the Hudson Valley.Located just 90 minutes from NYC and minutes from the Hudson Valley Rail Trail, wineries, and local farm markets, this move-in-ready home features modern upgrades, smart home touches, and

  Heather Bragg ReAttached

  46 Brescia Blvd, Highland, NY 12528
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  /24

  $350,000

  • 4 Beds
  • 1.5 Baths
  • 1,524 Sq Ft

  153 Upper Grand St, Highland, NY 12528

  Charming Cape Cod home ideally located outside the downtown of Highland is waiting for it's new owners! This quaint home is centrally located minutes from both NYS Thruway as well as Metro-North Railways, making commuting to work a breeze and is conveniently situated near local shops, restaurants, breweries/wineries, the Walkway Over the Hudson, and all that the vibrant areas that the Hudson

  John Quinn Quinn Realty Group Inc

  153 Upper Grand St, Highland, NY 12528
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  /33

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,715 Sq Ft

  334 Pancake Hollow Rd, Highland, NY 12528

  With 3 bedrooms, 2 full bathrooms, and 2,715 square feet of flexible living space, this turnkey home is ready for you to move right in and make it your own.At the heart of the home is a spacious open-concept kitchen and living room — perfect for everyday living and effortless entertaining. The generously sized primary suite offers both privacy and potential, with space to add an

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  334 Pancake Hollow Rd, Highland, NY 12528
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  /16

  $799,000

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

  104 North Rd, Highland, NY 12528

  Come explore this once in a lifetime oppurtunity! New construction duplex/2 family home located right in Highland on North Road. Will be a great investment property, rent both sides or live in one and rent the other. Both units include 3 bedrooms, 2 1/2 baths, full unfinished basement and approximately 1550 sq. ft. This home features stone front with large windows, lots of natural light, upgraded

  Marisa Bellacicco Century 21 Alliance Rlty Group

  104 North Rd, Highland, NY 12528
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  /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
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  /21

  $450,000

  • 4 Beds
  • 2 Baths
  • 2,266 Sq Ft

  12 Woodside Place, Highland, NY 12528

  Come see this home that offers a perfect combination of charm, convenience, and community. This beautiful 4-bedroom, 2-bath home is full of character, featuring original hardwood floors and elegant French doors. The spacious living and dining areas are ideal for family gatherings, while the kitchen boasts stunning granite countertops, perfect for cooking and entertaining. Enjoy peaceful mornings

  Geraldine Gaudioso Century 21 Alliance-NP

  12 Woodside Place, 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 BHHS HUDSON VALLEY PROP-NP

  9 Lumen Ln, Highland, NY 12528
• 

  

  /49

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,092 Sq Ft

  13 Sharon Dr, Highland, NY 12528

  Beautiful Ranch totally renovated ,new roof 2025 ,new siding 2025.Offer 3 bath and 1.5 Bath .Welcome to this charming ranch style home featuring 3 cozy bedrooms. As you step inside you will be greeted by beautiful commerce 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

  Drita Shala Howard Hanna Rand Realty

  13 Sharon Dr, Highland, NY 12528
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  /26

  $950,000

  • Land
  • 45.6 Acres
  • $20,833 per Acre

  73 Peach Ln, Clintondale, NY 12515

  One Beautiful Apple Orchard with Pond. Mountain View with a Million Dollar View. Mature Apple Trees will be ready to pick this fall. Two parcels 20.9 Acres and 24.7 Acres for a total Acres of 45.6 Acres each lot tax is $1000 both a year is $2000. one mile county road frontage.can access the property from two county roads. At the highest area of the orchard. is a clearing.no apple Trees. just

  John Melchior Howard Hanna Rand Realty

  73 Peach Ln, Clintondale, NY 12515

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