Homes for Sale near Highland High School

• 

  

  

  /35

  $675,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,656 Sq Ft

  14 Tina Dr, Highland, NY 12528

  Nestled on a serene, wooded acre, this thoughtfully renovated 3-bedroom, 2-bathroom home offers a harmonious blend of mid-century charm and modern comfort. Its distinctive double gambrel roofline and A-frame silhouette set it apart, creating an inviting retreat just minutes from the quaint village of Highland and the vibrant communities of New Paltz and Poughkeepsie, providing easy access to

  Monica Schwerberg Compass Greater NY, LLC

  14 Tina Dr, Highland, NY 12528
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• 

  

  

  /27

  $525,000

  • 4 Beds
  • 2.5 Baths
  • 2,184 Sq Ft

  19 Oak Crest Dr, Highland, NY 12528

  Blending comfort and style, this thoughtfully refreshed home is ready to welcome you. Major upgrades bring peace of mind, including a 50-year architectural roof (installed 2023) brand new bathrooms and beautiful new flooring throughout, including warm red oak hardwood that elevates the interior. The upstairs features all new carpeting, two fully renovated bathrooms, walk in primary closet, new

  Sandi Park Coldwell Banker Realty

  19 Oak Crest Dr, Highland, NY 12528
• 

  

  

  /47

  $559,900

  • 3 Beds
  • 2.5 Baths
  • 2,681 Sq Ft

  9 Lisa Dr, Highland, NY 12528

  Nestled on a picturesque one-acre lot at the beginning of a tranquil cul-de-sac in desirable Highland, New York, this extremely well-maintained raised Ranch offers an exceptional opportunity for comfortable and stylish living. Situated in a very highly thought of school district, this home boasts 2,681 square feet of thoughtfully designed space, featuring three bedrooms, two full bathrooms, and a

  JoAnn Ellis SUMMERSET REALTY

  9 Lisa Dr, Highland, NY 12528
• 

  

  

  /19

  $550,000

  • 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, this unique offering includes five individual parcels, presenting a blend of natural beauty, development potential, and historic charm. At the heart of the property is a c.1840s two

  Anthony DeGelormo Century 21 Alliance Rlty Group

  29 Oakes Rd, Highland, NY 12528
• 

  

  

  /33

  $499,000

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

  6 Smith Terrace, Highland, NY 12528

  Discover the perfect blend of modern style, flexible living, and serene surroundings in this beautifully updated ranch-style home, ideally located in the scenic town of Highland. Offering 1,728 sq ft of thoughtfully designed space, this 4-bedroom, 3-bathroom gem includes a fully legal 1-bedroom accessory apartment—making it as functional as it is stunning.From the moment you arrive, you’ll be

  Virginia Corbett eXp Realty

  6 Smith Terrace, Highland, NY 12528
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  /37

  $729,000

  • 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
• 

  

  /31

  $595,000

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  745 State Route 44 55, Highland, NY 12528

  Now Fully Available — Modern Farmhouse in Prime Highland LocationThis beautifully restored farmhouse perfectly balances historic charm with modern upgrades. Set on a scenic acre in the Highland School District, the home offers sun-filled interiors, soaring ceilings, and an open-concept layout designed for easy living.The first-floor primary suite adds comfort and convenience,

  Ashley Olson Minard eXp Realty

  745 State Route 44 55, Highland, NY 12528
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  /51

  $1,395,000

  • 7 Beds
  • 5 Baths
  • 4,630 Sq Ft

  660 N Chodikee Lake Rd, Highland, NY 12528

  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, with frontage on Chodikee Lake reached just across a

  Hayes Clement Compass Greater NY, LLC

  660 N Chodikee Lake Rd, Highland, NY 12528
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  /35

  $548,000

  • 5 Beds
  • 5 Baths
  • 2,382 Sq Ft

  20-22 Milton Ave, Highland, NY 12528

  Move-in ready and close to all the best amenities: This spacious two-unit Victorian in the heart of the village of Highland is just steps from popular restaurants and shops, and only minutes by car or bicycle to the Walkway Over the Hudson, New Paltz, and NYC-bound Metro-North service at Poughkeepsie. The first-floor unit features 2 bedrooms, 1 bath, a private deck, and 2 separate entrances,

  Hayes Clement Compass Greater NY, LLC

  20-22 Milton Ave, Highland, NY 12528
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  /48

  $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 NY, LLC

  9 Chambers Rd, West Park, NY 12493
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  /36

  $449,500

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

  67 Picnic Woods Rd, Clintondale, NY 12515

  Welcome to your dream ranch home in Clintondale, NY—where comfort, style, and convenience come together in perfect harmony. This clean, well-maintained home set on a serene 1-acre lot is relaxing and inviting, making it the perfect retreat. Imagine waking up to the serenity of the beautiful pond as you enjoy your breakfast on the rear deck or before sunset when the sun is low on the horizon—a

  JANICE CARRASCO Nexthome NOVACARR Realty

  67 Picnic Woods Rd, Clintondale, NY 12515
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  /6

  $247,000

  • Land
  • 3.90 Acres
  • $63,333 per Acre

  5 Elbow Ln, Highland, NY 12528

  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 this 9 lot sub division have been built with an eye on design and privacy.

  Elizabeth Decker Hello Dolly Real Estate

  5 Elbow Ln, Highland, NY 12528
• 

  

  /31

  $385,000

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft

  10 Perkinsville Rd, Highland, NY 12528

  Opportunity Knocks in Highland, NY! This well-cared-for 3 bedroom, 2 full bathroom raised ranch is tucked into an established neighborhood right off Route 9W in the Town of Highland. With a spacious layout and a peaceful, wooded backdrop, you’ll enjoy beautiful views right from your back deck — perfect for morning coffee or evening relaxation.The home offers solid bones and has been lovingly

  Eva Kusmierek eXp Realty

  10 Perkinsville Rd, Highland, NY 12528
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  /5

  $125,000

  • Land
  • 0.90 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
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  /25

  $420,000

  • 3 Beds
  • 1.5 Baths
  • 3,124 Sq Ft

  8 Perkinsville Rd, Highland, NY 12528

  Discover your perfect Hudson Valley escape with this beautifully maintained raised ranch located in the heart of Highland, NY. Nestled on a quiet street and just minutes from the Mid-Hudson Bridge and NYS Thruway, this home offers both convenience and tranquility. This well-maintained 3-bedroom, 1.5-bath raised ranch combines classic charm with standout features—most notably, a sun-drenched

  Kelly Martin Michael A. Martin

  8 Perkinsville Rd, Highland, NY 12528
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  /12

  $95,000

  • Land
  • 5.00 Acres
  • $19,000 per Acre

  Lot 55 Timber Lake Dr, Eldred, NY 12528

  Build your dream home on Private 5 acre parcel with lake rights down the road in lovely gated community. Lake access, beach, boating, fishing within walking distance from the Lake.

  Jane Panico Realty Promotions Inc

  Lot 55 Timber Lake Dr, Eldred, NY 12528
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  /10

  $95,000

  • Land
  • 5 Acres
  • $18,555 per Acre

  Lot 53 Timber Lake Dr, Eldred, NY 12528

  Build your dream home on Private 5 acre parcel with lake rights down the road in lovely gated community. Lake access, beach, boating, fishing within walking distance from the Lake.

  Jane Panico Realty Promotions Inc

  Lot 53 Timber Lake Dr, Eldred, NY 12528
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  /42

  $379,000

  • 3 Beds
  • 2 Baths
  • 2,314 Sq Ft

  312 Crescent Ave, Highland, NY 12528

  A Romantic Restoration Opportunity | New Paltz NY Area 3BD | 2BA | Victorian w/ Carriage House Located in the beautiful hamlet of Clintondale Tucked in the rolling farm country of the Hudson Valley, (lots of farms equals low taxes) just 90 minutes from NYC by car bus or train. Metro north and Amtrak 14 mins away this quintessential Victorian offers a rare opportunity to restore something truly

  Machree Quaker The Machree Group, LLC

  312 Crescent Ave, Highland, NY 12528
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  /17

  $329,000 Open Sun 12PM - 1:30PM

  • 3 Beds
  • 2.5 Baths
  • 1,121 Sq Ft

  37 Maple Ave, Highland, NY 12528

  Freshly redone, Colonial style house 1,000 feet to the Hudson & Highland Landing Park. The open floor plan downstairs gives that airy fresh touch. Beautiful all new kitchen and appliances. Lots of windows. Upstairs, 3 spacious bedrooms and 2 full bathrooms. Make this opportunity your home and enjoy the beauties of the Hudson and this sweet contemporary home.

  Meyer Stoessel Keller Williams Hudson Valley

  37 Maple Ave, Highland, NY 12528
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  /19

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,470 Sq Ft

  460 Vineyard Ave, Highland, NY 12528

  This property in Highland is a charming two-story home that offers a blend of comfort and modern amenities. This spacious residence features a dedicated office space, perfect for remote work or study. The kitchen has been newly renovated, boasting beautiful granite countertops and elegant wood cabinetry, making it both functional and stylish. For those who appreciate organization, a large pantry

  Dawn Passante Coldwell Banker Village GreenN

  460 Vineyard Ave, Highland, NY 12528
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  /6

  $825,000

  • Land
  • 16 Acres
  • $50,000 per Acre

  TBD South St, Lloyd, NY

  Prime property. This parcel is flat, mostly cleared, has a pond, sweeping views of the Shawangunk Mountains and borders the 27 hole Apple Greens Golf Course. 1,400 feet of the property adjoins the course. If golf is your game, it doesn't get any more convenient than this. Perfect for a community that grew up here, wants to stay here and are ready to downsize and become ''snow birds''. Here for

  Dennis Cooper Corcoran Country Living

  TBD South St, Lloyd, NY
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  /18

  $375,000

  • 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
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  /15

  $75,000

  • 2 Beds
  • 1 Bath
  • 840 Sq Ft

  107 Floyd Ackert Rd Unit 10, Hyde Park, NY 12538

  This home has been completely updated from top to bottom and is located in a highly desirable and conveniently located park with very low lot rent. Updates include kitchen with stainless steel appliances, bathroom with jacuzzi tub, vinyl siding, low E windows, deck, furnace, hot water heater, and new flooring throughout. Freshly painted. Washer/Dryer hookups. Large lot with shed.

  AARON VIGNOGNA Century 21 Alliance Rlty Group

  107 Floyd Ackert Rd Unit 10, Hyde Park, NY 12538
• 

  

  /22

  $425,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  618 N Chodikee Lake Rd, Highland, NY 12528

  WOW! Stunning Renovation! This beautifully updated 3-bedroom 2 bath ranch, set on 1 acre on a country road, offers modern elegance throughout. The brand-new kitchen features quartz countertops, a marble backsplash, and new appliances. Gorgeous gleaming hardwood floors, updated lighting, and NEW bathrooms with the latest designer tiles. With NEW windows, vinyl siding, a full basement, and a

  Naomi Streicher Q Home Sales

  618 N Chodikee Lake Rd, Highland, NY 12528
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  /43

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 4,798 Sq Ft

  1535 Route 9w, West Park, NY 12493

  Exquisite waterfront estate located on the majestic Hudson River. Discover an extraordinary waterfront estate offering approximately 4,800 sqft of luxurious living space, accompanied by a private 1,000 sqft guest houseâ€both offering panoramic, breathtaking Hudson River views and an array of unparalleled amenities. Nestled on 800 feet of private river frontage, this

  Eliana Amodio Amodio Real Estate & Prop

  1535 Route 9w, West Park, NY 12493
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  /48

  $2,950,000

  • 4 Beds
  • 3 Baths
  • 4,798 Sq Ft

  1535 Route 9w, Hyde Park, NY 12538

  Exquisite waterfront estate located on the majestic Hudson River. Discover an extraordinary waterfront estate offering approximately 4,800 sqft of luxurious living space, accompanied by a private 1,000 sqft guest house‚ both offering panoramic, breathtaking Hudson River views and an array of unparalleled amenities.Nestled on 400 feet of private river frontage, this stunning 4-bedroom,

  Mary Spinac Amodio Real Estate & Prop

  1535 Route 9w, Hyde Park, NY 12538
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  /6

  $825,000

  • Land
  • 16 Acres
  • $50,000 per Acre

  tbd South St, Highland, NY 12528

  Prime property. This parcel is flat, mostly cleared, has a pond, sweeping views of the Shawangunk Mountains and borders the 27 hole Apple Greens Golf Course. 1,400 feet of the property adjoins the course. If golf is your game, it doesn't get any more convenient than this. Perfect for a community that grew up here, wants to stay here and are ready to downsize and become ''snow birds''. Here for

  Dennis Cooper Corcoran Country Living

  tbd South St, Highland, NY 12528
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  /14

  $75,000

  • Land
  • 1.36 Acres
  • $55,147 per Acre

  0 White St, Highland, NY 12528

  Looking for the perfect lot for your new home? This lovely 1.36-acre lightly 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

  Carolyn Michelle Keller Williams Realty Partner

  0 White St, Highland, NY 12528
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  /21

  $415,000

  • 3 Beds
  • 1.5 Baths
  • 1,683 Sq Ft

  15 Toc Dr, Highland, NY 12528

  This charming raised ranch offers three spacious bedrooms, one and a half bathrooms, and approximately 1,683 square feet of living space on a generous 0.36-acre lot. Located in a desirable neighborhood, this home provides comfort, convenience, and a fantastic location near Highland’s best amenities.The main level features a bright and inviting living room that flows into the dining area and

  John Quinn Quinn Realty Group Inc

  15 Toc Dr, Highland, NY 12528
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  /6

  $249,000

  • Land
  • 4.00 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
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  /34

  $349,900

  • 3 Beds
  • 1.5 Baths
  • 1,360 Sq Ft

  94 Sunny Brook Cir, Highland, NY 12528

  Lovely 3 bedroom townhouse nestled on a private walkway at the end of Sunny Brook Circle. The inviting front door opens into a nicely sized livingroom that looks out on trees and flowering bushes. At the back of the home are the large dining area and kitchen which is equipped with new stainless appliances including a French door refrigerator, gas range, microwave, and dishwasher. A laundry

  ROSLYN RALSTON HomeSmart Homes & Estates

  94 Sunny Brook Cir, Highland, NY 12528
• 

  

  /22

  $325,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft

  16 Fair St, Highland, NY 12528

  Pack your bags, you've found the one! With a little TLC this could be your "home sweet home". This 4-bedroom, 2 full bath home has room for all. Rocking chair front porch and level yard at the end of a cul-de-sac location add to the appeal of this property. Centrally located, just over the west end of the Mid-Hudson Bridge. Close to parks, schools, shopping, public transportation, medical

  Lynne Riccoboni BHHS Hudson Valley Properties

  16 Fair St, Highland, NY 12528
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  /13

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft

  8 Marie, Highland, NY 12528

  Don't miss out on this incredible Opportunity! A Stunning Duplex in the Heart of Highland with 2 units, one with 2 bedrooms, 1 bath and one with 1 bedroom, 1 bath. First floor unit has open floor plan and both units have many upgrades such as mini splits, new bathrooms, updated plumbing, new roof and much more. This beautifully maintained home is a rare find. This home can be easily turned into a

  Angela Paul Century 21 Alliance Rlty Group

  8 Marie, Highland, NY 12528
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  /15

  $399,000

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

  3748 Route 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,

  Lindsay Stevens eXp Realty

  3748 Route 9w, Highland, NY 12528
• 

  

  /15

  $399,000

  • Land
  • 9 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
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  /7

  $25,000

  • Land
  • 0.13 Acre
  • $192,308 per Acre

  0 New York 299, Highland, NY 12528

  Property located on 299 in the DB zone. Call Building Department is Highland to find out what type of usage is allowed.

  JoAnn Ellis Summerset Realty

  0 New York 299, Highland, NY 12528
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  /7

  $25,000

  • Land
  • 0.13 Acre
  • $192,308 per Acre

  0 Route 299 New Paltz Unit KEY816284, Highland, NY 12528

  Property located on 299 by Kisor Road. Located in the DB district. Contact building department in town of Lloyd to verify use of property.

  JoAnn Ellis Summerset Realty

  0 Route 299 New Paltz Unit KEY816284, Highland, NY 12528
• 

  

  /7

  $25,000

  • Land
  • 0.13 Acre
  • $192,308 per Acre

  0 Route 299 New Paltz Unit 11413322, Highland, NY 12528

  Property located on 299 by Kisor Road. Located in the DB district. Contact building department in town of Lloyd to verify use of property.

  JoAnn Ellis SUMMERSET REALTY

  0 Route 299 New Paltz Unit 11413322, Highland, NY 12528
• 

  

  /14

  $239,900

  • 1 Bed
  • 1 Bath
  • 762 Sq Ft

  534 New Paltz Rd, Highland, NY 12528

  Step into this completely renovated 1-bedroom, 1-bath home designed for comfort and convenience. The entire house has been fully renovated featuring new countertops and cabinets in the kitchen, new stainless steel appliances, and stylish laminated wood floors, together with the roof and septic system.The 762 sq. ft. layout is versatile and functional, making it ideal for any stage of life.

  Stefan Bolz Hello Dolly Real Estate

  534 New Paltz Rd, Highland, NY 12528
• 

  

  /21

  $475,000

  • 4 Beds
  • 1.5 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

  Angela Chenery Century 21 Alliance Rlty Group

  12 Woodside Place, Highland, NY 12528

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