Highland, NY Homes

Est $374,551 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,464 Sq Ft
9 Argent Dr, Highland, NY 12528

9 Argent Dr, 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
/29
$344,900 Sold Jul 18, 2025
- 1,681 Sq Ft
- $205/SF
- 56 Days On Market
- 3 Beds
- 2 Baths
- Built 1962
124 Half Moon Rd, Highland, NY 12528

Discover the potential of this charming brick ranch nestled on a serene 8 acre property offering seasonal mountain views. Conveniently located, this property presents a unique opportunity for those seeking a tranquil retreat with ample room for expansion and renovation.Inside, envision creating your dream home with a thoughtful remodel. The spacious layout includes an oversized laundry

Paige McClintock Howard Hanna Rand Realty

124 Half Moon Rd, Highland, NY 12528

Est $284,961 Not Listed For Sale
- 2 Beds
- 1 Bath
- 946 Sq Ft
769 Gregory Ct, Highland, NY 12528

769 Gregory Ct, Highland, NY 12528

/13
$500,000
- Land
- 11.5 Acres
- $43,478 per Acre
TBD Route 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 Route 9w, Highland, NY 12528
$277,000 Sold Jul 15, 2025
- 1,272 Sq Ft
- $218/SF
- 102 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1985
23 Toc Dr, Highland, NY 12528

Chance to own a 3 bedroom 1.5 bath home in the Hamlet of Highland. Includes an enclosed porch and a fenced in yard with 2 storage units. This is a rowhouse style home and there are no HOA fees as it is an attached single family. Close to the train station in Poughkeepsie, the walkway over the Hudson and many biking and hiking trails.

Randy Spiesman Weichert REALTORS

23 Toc Dr, Highland, NY 12528

/19
Est $283,285 Not Listed For Sale
- 2 Beds
- 1 Bath
- 940 Sq Ft
561 Gregory Ct Unit 611, Highland, NY 12528

561 Gregory Ct Unit 611, Highland, NY 12528

/2
$29,000
- Land
- 0.79 Acre
- $36,709 per Acre
0 Hartung Rd Unit H6242040, Highland, NY 12732

Fantastic level lot. Minutes walk to Sand Beach. Close to lots of great local restaurants, Bethel Woods performing arts center and the Delaware river.

Dawn Payne Payne Team LLC

0 Hartung Rd Unit H6242040, Highland, NY 12732
/23
$295,000 Sold Jul 09, 2025
- 1,220 Sq Ft
- $242/SF
- 110 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1974
4 Sunnybrook Cir, Highland, NY 12528

Welcome home to this well-maintained townhouse in Highland's Sunnybrook community. Whether buying your first home or looking to downsize, this bright 3-bedroom, 1.5 bath residence has much to offer. The open kitchen and dining area features a convenient pantry closet with washer and dryer, and flows through sliding glass doors to your private fenced deck—perfect for summer gatherings or your

Anita Cunniff Boxwood Realty and Design

4 Sunnybrook Cir, Highland, NY 12528

Est $308,523 Not Listed For Sale
- 2 Beds
- 1 Bath
- 946 Sq Ft
549 Gregory Ct Unit 68, Highland, NY 12528

549 Gregory Ct Unit 68, 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
/31
$425,000 Sold Jul 08, 2025
- 2,524 Sq Ft
- $168/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1994
831 N Chodikee Lake Rd, Highland, NY 12528

Charming 3-Bedroom Chalet with Seasonal Lake Views! Nestled at the end of a quiet dead-end road, this cozy 3-bedroom chalet offers the perfect blend of comfort, charm, and convenience—with stunning seasonal views of beautiful Chodikee Lake. Step into the warm and inviting first floor, where an open-concept living room, kitchen, and dining area create a bright and airy space ideal for everyday

Dawn Passante Coldwell Banker Village GreenN

831 N Chodikee Lake Rd, Highland, NY 12528

Est $297,868 Not Listed For Sale
- 2 Beds
- 1 Bath
- 946 Sq Ft
555 Gregory Ct Unit 603, Highland, NY 12528

555 Gregory Ct Unit 603, 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
$727,000 Sold Jul 08, 2025
- 1,600 Sq Ft
- $454/SF
- 43 Days On Market
- 3 Beds
- 2 Baths
- Built 2025
9 White Pine Ln, Highland, NY 12719

A refined oasis awaits you at White Pines, just two hours from NYC in serene Barryville, NY. Tucked away on the banks of Beaver Brook, this newly constructed three bedroom, two bathroom modern cabin is the private, light-drenched retreat you’ve been looking for. An open concept living space features soaring ceilings and an abundance of oversized windows, making the most of the surrounding

Megan Kinealy-Hill Country House Realty Inc

9 White Pine Ln, Highland, NY 12719

/27
Est $298,916 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,027 Sq Ft
434 Gregory Ct, Highland, NY 12528

434 Gregory Ct, Highland, NY 12528

/5
$35,000 Pending
- Land
- 6.06 Acres
- $5,776 per Acre
0 Split Rock Dr Unit ONEH6305826, Highland, NY 12719

This peaceful and serene 6+ acre lot in Pyne Ayre Subdivision in Barryville, NY offers seclusion and a quiet place to build your dream home. Just bring your house plans and imagine sitting on your deck, listening to mother nature. Driveway is already in place. Close to Delaware River access, rafting, fishing and hiking trails, restaurants and you can even catch a concert at the nearby Bethel

Gibson McKean Payne Team LLC

0 Split Rock Dr Unit ONEH6305826, Highland, NY 12719
/31
$369,000 Sold Jul 07, 2025
- 1,311 Sq Ft
- $281/SF
- 29 Days On Market
- 3 Beds
- 2 Baths
- Built 1987
10 Perkinsville Rd, Highland, NY 12528

Opportunity Knocks in Highland, NY! This well-cared-for three-bedroom, two-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 surranding, 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, LLC

10 Perkinsville Rd, Highland, NY 12528

Est $289,881 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,027 Sq Ft
444 Gregory Ct, Highland, NY 12528

444 Gregory Ct, Highland, NY 12528

/13
$950,000 Pending
- 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 fully occupied 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 fully occupied home with two bedrooms and one full bathroom per unit for a total of around 1,125 sq ft. Both

Diane Mi Ryoung Chong HANMI REALTY

10-32 S Roberts Rd, Highland, NY 12528
$370,000 Sold Jul 02, 2025
- 1,956 Sq Ft
- $189/SF
- 108 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1987
45 Cotter Rd, Highland, NY 12528

Nestled on a picturesque 5.2-acre lot in Highland, NY, this charming 3-bedroom, 2.5-bathroom home offers a perfect blend of comfort and natural beauty. Spanning 1,956 sq ft, this inviting residence provides plenty of space for families or anyone looking for a serene retreat. The lush, expansive grounds feature open areas perfect for outdoor activities, gardening, or simply enjoying the tranquil

Virginia Corbett eXp Realty

45 Cotter Rd, Highland, NY 12528

/16
Est $288,883 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,027 Sq Ft
428 Gregory Ct, Highland, NY 12528

428 Gregory Ct, Highland, NY 12528

/41
$579,900 Pending
- 4 Beds
- 2.5 Baths
- 2,480 Sq Ft
30 Mayer Dr, Highland, NY 12528

Welcome to this beautifully maintained home offering a spacious, light-filled layout designed for both comfort and style. The main level features a stunning eat-in kitchen with granite countertops, a classic tiled backsplash, stainless steel appliances, a pantry, and a generous center island — perfect for cooking, casual dining, and gathering. Seamlessly connected is the inviting living room with

Margaret Thorne Keller Williams Hudson Valley

30 Mayer Dr, Highland, NY 12528
/18
$350,000 Sold Jul 01, 2025
- 1,900 Sq Ft
- $184/SF
- 64 Days On Market
- 3 Beds
- 2 Baths
- Built 1986
25 Deller Rd, Highland, NY 12528

Comfortable single level ranch home with 3 bedrooms and two full bathrooms. The one car garage has been converted into a beautiful light-filled family room for additional living space. Enjoy the large eat-in kitchen, just off the dining room. Sliders lead out to back deck with its private yard that's perfect for entertaining and summer barbecues. There's even a full unfinished basement for extra

Dawn Passante Coldwell Banker Village GreenN

25 Deller Rd, Highland, NY 12528

/22
Est $272,253 Not Listed For Sale
- 2 Beds
- 1 Bath
- 946 Sq Ft
204 Gregory Ct, Highland, NY 12528

204 Gregory Ct, Highland, NY 12528

/12
$265,000 Pending
- 2 Beds
- 1 Bath
- 1,056 Sq Ft
53 Sunny Brook Cir, Highland, NY 12528

Welcome to this inviting 2-bedroom townhouse unit, 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
/35
$680,000 Sold Jun 27, 2025
- 1,656 Sq Ft
- $411/SF
- 20 Days On Market
- 3 Beds
- 2 Baths
- Built 1974
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

Est $284,439 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,027 Sq Ft
210 Gregory Ct, Highland, NY 12528

210 Gregory Ct, Highland, NY 12528

/13
$180,000 Pending
- Land
- 16.45 Acres
- $10,942 per Acre
0 Zane Grey Way Unit KEY906582, Highland, NY 12719

Suspended in the clouds, a thousand feet above the Delaware River, this serene 16-acre legacy homesite cradles sweeping river views winding through the protected Pennsylvania State Game Lands beyond. Colossal stone formations sculpt the bluff, from which ancient pines ascend skyward, their roots woven into stone as if carved by time itself. Balancing raw natural grandeur with the privilege of

Owen Boller Boller Properties

0 Zane Grey Way Unit KEY906582, Highland, NY 12719
/23
$678,734 Sold Jun 27, 2025
- 1,754 Sq Ft
- $387/SF
- 25 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1998
368 Plutarch Rd, Highland, NY 12528

Privately sited among mature and flowering trees with plenty of open space to play is this well-maintained home located minutes to the vibrant towns of New Paltz and Highland. New Paltz School District. Upon entering you'll find gleaming oak floors, a light-filled open living room with wood-burning fireplace and dining area overlooking the back yard and large deck. The kitchen is central

Helen Coyle Bergstein Helen Coyle Bergstein

368 Plutarch Rd, Highland, NY 12528

/8
Est $269,189 Not Listed For Sale
- 2 Beds
- 1 Bath
- 964 Sq Ft
202 Gregory Ct, Highland, NY 12528

202 Gregory Ct, Highland, NY 12528

/28
$315,000 Pending
- 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
/14
$392,000 Sold Jun 27, 2025
- 1,720 Sq Ft
- $228/SF
- 119 Days On Market
- 3 Beds
- 2 Baths
- Built 1900
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 Past Member

8 Marie, Highland, NY 12528

/32
Est $331,749 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,175 Sq Ft
162 Sterling Place, Highland, NY 12528

162 Sterling Place, Highland, NY 12528

/13
$329,999 Pending
- 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
/18
$165,000 Sold Jun 25, 2025
- Land
- 12.81 Acres
- $12,881 per Acre
- 98 Days On Market
274 Swartekill Rd, Highland, NY 12528

If you have been looking for that beautifully wooded and secluded parcel of land to build your home in the country, look no further. Located on Swarte Kill Road, one of the most quiet and picturesque rural roads in the Town of Esopus, you'll find 12.81 acres of pristine conifer and hardwood Forest, which is largely bounded by stunning hand laid stone walls. The property is accessed by an old

Brian Cafferty Halter Associates Realty

274 Swartekill Rd, Highland, NY 12528

Est $334,994 Not Listed For Sale
- 3 Beds
- 1.5 Baths
- 1,302 Sq Ft
154 Sterling Place, Highland, NY 12528

154 Sterling Place, Highland, NY 12528

/8
$129,000 Pending
- 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
$260,000 Sold Jun 24, 2025
- 1,040 Sq Ft
- $250/SF
- 141 Days On Market
- 3 Beds
- 1 Bath
- Built 1963
411 Vineyard Ave, Highland, NY 12528

Three bedroom, one bathroom ranch with easy access to the Village of Highland! Cute brick home with covered front porch great for a hammock or rocking chair. Hardwood floors on the main level. Updated mechanicals. Basement area has additional rooms not included in finished square footage. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes.

Brian Smith River Realty Services, Inc.

411 Vineyard Ave, Highland, NY 12528

/32
Est $353,223 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,270 Sq Ft
116 Sterling Place, Highland, NY 12528

116 Sterling Place, Highland, NY 12528

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