Homes for Sale near Highland High 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
• 

  Explore Highland High 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
• 

  

  

  /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 17, 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.

  

  Hayes Clement

  Compass Greater NY, LLC

  (845) 378-9916

  660 N Chodikee Lake Rd, Highland, NY 12528
• 

  

  

  /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
• 

  

  

  /26

  $599,000

  • 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

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
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  /24

  $575,000

  • 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
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  /44

  $1,299,000

  • 3 Beds
  • 2.5 Baths
  • 3,068 Sq Ft

  243 Hawleys Corners Rd, Highland, NY 12528

  Discover the perfect blend of craftsmanship, comfort and opportunity in this stunning custom-built Craftsman home, offering over 3,000 square feet of living space on 20 picturesque acres. Previously subdivided with six additional parcels, this property offers exceptional potential for expansion, development or a private gathering retreat. Inside, you will find cathedral ceilings, custom woodwork,

  Melissa Pettinella Century 21 Alliance Realty Grp

  243 Hawleys Corners Rd, Highland, NY 12528
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  /44

  $869,000

  • 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 countertops,

  Lindsay Stevens eXp Realty

  1 Janine Place, Highland, NY 12528
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  /48

  $529,900 Open Sat 11AM - 1PM

  • 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
• 

  

  /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
• 

  

  /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
• 

  

  /23

  $295,000

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

  48 Sunny Brook Cir, Highland, NY 12528

  Welcome to 48 Sunny Brook Circle, where easy living meets effortless style. This sun-drenched, single-level end unit offers 1,056 square feet of comfort and charm, designed for those who crave simplicity without compromise. Step inside and you'll find a bright, open layout featuring a spacious eat-in kitchen, a welcoming living room, a private primary suite, and a versatile converted den (legal

  Leigh Wagner-Quintana Keller Williams Realty HV Nort

  48 Sunny Brook Cir, Highland, NY 12528
• 

  

  /17

  $245,000

  • 2 Beds
  • 2 Baths
  • 1,456 Sq Ft

  16 Trout Brook Ln, Highland, NY 12528

  Beautiful Hudson Valley location encompassed by apple orchards, farms, colleges, yet still close to trains and airports. Immaculate 2017 1456 sq. ft. manufactured home includes central air, forced hot air propane heat, stainless steel appliances, front and side porches, and large shed with electric. Upgrades include custom walk-in closet, Rapid Wall insulated skirting with side access door, vinyl

  Lisa Cozzolino Cronin & Company Real Estate

  16 Trout Brook Ln, Highland, NY 12528
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  /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 Highlanding 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
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  /7

  $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-NP

  TBD Hawleys Corners Rd, Highland, NY 12528
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  /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
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  /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
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  /47

  $399,900

  • 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
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  /33

  $434,900 Open Sat 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 1,728 Sq Ft

  6 Smith Terrace, Highland, NY 12528

  Welcome to this beautifully updated four-bedroom, three-bath contemporary ranch which includes a rentable 1 bedroom accessory apartment in Highland, Ulster County. With over 1,700 square feet of living space on a third of an acre, this home offers a thoughtful blend of style, function, income potential and flexibility. Inside, the open layout highlights hardwood and tile flooring, exposed

  Virginia Corbett eXp Realty

  6 Smith Terrace, Highland, NY 12528
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  /10

  $110,000

  • Land
  • 2.1 Acres
  • $52,381 per Acre

  748 State Route 44 55, Highland, NY 12528

  This expansive 2.1-acre lot is fully surveyed and features a perk-test-approved septic—offering peace of mind as you plan and build your dream home. Nestled along a picturesque country road, the property provides a perfect balance of privacy and convenience. Enjoy easy access to the Mid-Hudson Bridge, NYS Thruway, shopping, local eateries, and all the natural beauty and charm the Hudson Valley

  Ashley Olson Minard eXp Realty

  748 State Route 44 55, 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
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  /68

  $1,500,000

  • 3 Beds
  • 3.5 Baths
  • 3,472 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
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  /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
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  /5

  $485,000

  • Land
  • 6.3 Acres
  • $76,984 per Acre

  76 Bellevue Rd, Lloyd, NY 12528

  *Drone footage of building site and potential driveway available.*Welcome to 76 Bellevue road. A 6.3 acre lot along one of the Hudson Valley's most sought-after waterfront roads. This offering presents an opportunity to build a dream home with sweeping Hudson River views. Create a meandering driveway through lush, private woodlands leading to a flat, elevated site perfectly situated to

  Theodore Chazkel Four Seasons Sotheby's Int'l R

  76 Bellevue Rd, Lloyd, NY 12528
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  /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
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  /29

  $1,850,000

  • 3 Beds
  • 4 Baths
  • 2,884 Sq Ft

  226 Burroughs Dr, West Park, NY 12493

  Perched above the Hudson with sweeping river views, this beautifully renovated home offers 3 bedrooms, 4 full baths, and two versatile rooms ideal for a home office or study. This property blends timeless charm with modern comforts, featuring interiors bathed in natural light from expansive windows and skylights. Original details from the early 1900s are thoughtfully preserved, giving the home a

  Juliana Botta Four Seasons Sotheby's Int.

  226 Burroughs Dr, West Park, NY 12493
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  /43

  $525,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3 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

  $499,900

  • 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
• 

  

  /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
• 

  

  /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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  /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
• 

  

  /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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  /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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  /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 Hudson Valley

  334 Pancake Hollow Rd, Highland, NY 12528
• 

  

  /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 Four Seasons Sotheby's Int'l R

  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
• 

  

  /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
• 

  

  /19

  $395,000

  • Land
  • 7.2 Acres
  • $54,861 per Acre

  75 Palazzo Ln, Clintondale, NY 12528

  Build your dream home or investment property on this exceptional 7.2-acre parcel of land, ideally situated in the heart of the Hudson Valley. Just 5 miles from the New Paltz Thruway exit (I-87), 6 miles to SUNY New Paltz, and 7 miles to the vibrant New Paltz Village, this location offers the perfect balance of privacy and accessibility.The property features a producing apple orchard with

  Michele Richards Four Seasons Sotheby's Int.

  75 Palazzo Ln, Clintondale, NY 12528
• 

  

  /33

  $2,000,000

  • 3 Beds
  • 2.5 Baths
  • 2,322 Sq Ft

  70 Floyd Ackert Rd, West Park, NY 12493

  A Rare Hudson Riverfront Opportunity - Historic Stone Home with Unmatched Views and Endless Potential It's not often a property like this becomes available—a one-of-a-kind 1870s stone ferry house, set on 3.3 private acres right at the edge of the Hudson River. With sweeping, unobstructed views and a direct connection to the water, this is a chance to create something truly extraordinary.Step

  Jeanne Rakowski Corcoran Country Living

  70 Floyd Ackert Rd, West Park, NY 12493

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