Highland, NY Homes

/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

(845) 552-0012

13 Sharon Dr, Highland, NY 12528
/50

$2,727 - $6,488 per month

Vineyard Commons

2 - 3 Beds

6142 Merlot Dr, Highland, NY 12528

Vineyard Commons offers a fresh approach to active adult living, combining comfort, convenience and style. Our spacious two and three bedroom apartments feature vaulted ceilings, abundant closet space and gourmet kitchens with granite countertops and stainless steel appliances, all on a single level for effortless living. Enjoy the freedom to do as much or as little as you like with amenities

6142 Merlot Dr, Highland, NY 12528
/29
$344,900 Sold Jul 18, 2025

124 Half Moon Rd, Highland, NY 12528
- 3 Beds
- 2 Baths
- 1,681 Sq Ft
- Built 1962
Last Sold Summary
- $205/SF
- 56 Days On Market
Current Estimated Value $369,137

Last Listing Agent Paige McClintock Howard Hanna Rand Realty

124 Half Moon Rd, Highland, NY 12528

Est $584,541 Not Listed For Sale

288 Baileys Gap Rd, Highland, NY 12528
- 4 Beds
- 4 Baths
- 2,478 Sq Ft
- Built 2009
288 Baileys Gap Rd, Highland, NY 12528

Last Sold Summary
- 9% Above List Price
- $216/SF
- 59 Days On Market
Last Sold Price $535,000

Last Listing Agent Ryan Sylvestri RE/MAX

/14
$295,000 Pending
- 2 Beds
- 1 Bath
- 946 Sq Ft
787 Gregory Ct, Highland, NY 12528

Modern Hudson Valley Living Starts Here. Welcome to this stunningly updated 1ST FLOOR 2-bedroom, 1-bathroom condo located in the highly sought-after community in Bridgeview. From the moment you step inside, you’ll notice the meticulous care and contemporary finishes that make this unit truly move-in ready. The chef-inspired kitchen is a showstopper, featuring sleek granite countertops, high-end

Eugene Valoy

BHHS Hudson Valley Properties

(845) 719-4972

787 Gregory Ct, Highland, NY 12528
/9
$1,550 per month
- 1 Bath
- 3,712 Sq Ft
- Apartment for Rent
4 Milton Ave Unit 1, Highland, NY 12528

Beautiful, Sun-Filled Studio in the Heart of the Town of Lloyd Bright, updated studio with hardwood floors, recessed lighting, wrap-around windows, and a modern kitchen with stainless steel appliances and quartz counters. Fully updated bathroom, two large closets, mini-split heating/cooling, and off-street parking. 500 Square-feet. Utilities not included.

Etnik Berisha K. Fortuna Realty, Inc.

4 Milton Ave Unit 1, Highland, NY 12528
/31
$425,000 Sold Jul 08, 2025

831 N Chodikee Lake Rd, Highland, NY 12528
- 3 Beds
- 2 Baths
- 2,524 Sq Ft
- Built 1994
Last Sold Summary
- $168/SF
- 10 Days On Market
Current Estimated Value $497,687

Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

831 N Chodikee Lake Rd, Highland, NY 12528

Not Listed For Sale

32 Timber Lake Dr, Highland, NY 12792
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
- Built 2007
32 Timber Lake Dr, Highland, NY 12792

Last Sold Summary
- $297/SF
- 14 Days On Market
Last Sold Price $525,000

Last Listing Agent Erik Freeland Country House Realty Inc

/18
$59,900
- Land
- 6.09 Acres
- $9,836 per Acre
Lot 28 Summit Dr, Highland, NY 12792

Beautiful 6+/- acres in gated community! This peaceful property is a nice corner parcel with a lot of road frontage that is mostly level and wooded. This is a great place to build your dream home with lake rights to Timber Lake Estates. Close to Eldred, Barryville and the Delaware River. Come take a look at this property before it's gone!

Dawn Curreri

Eagle Valley Realty

(845) 412-9934

Lot 28 Summit Dr, Highland, NY 12792
/13

$2,300 per month

Trailview Place

2 Beds

42 Toc Dr, Highland, NY 12528

Welcome to your new home in the heart of Highland, NY! This apartment community offers comfort and convenience in a prime location. Situated just steps away from the scenic rail trail and the iconic Mid-Hudson Bridge, outdoor enthusiasts will love the easy access to biking, walking, and breathtaking views. If you're a commuter, the nearby train station provides a stress-free option for travel.

42 Toc Dr, Highland, NY 12528
$185,000 Sold Jan 21, 2026

16 Trout Brook Ln, Highland, NY 12528
- 2 Beds
- 2 Baths
- 1,456 Sq Ft
- Built 2017
Last Sold Summary
- 24% Below List Price
- $127/SF
- 58 Days On Market
Last Listing Agent Lisa Cozzolino Cronin & Company Real Estate

16 Trout Brook Ln, Highland, NY 12528

Est $574,284 Not Listed For Sale

274 Fosler Rd, Highland, NY 12528
- 4 Beds
- 3 Baths
- 2,197 Sq Ft
- Built 2023
274 Fosler Rd, Highland, NY 12528

Last Sold Summary
- 15% Above List Price
- $228/SF
- 78 Days On Market
Last Sold Price $499,999

Last Listing Agent Richard Baxter Keller Williams Realty

/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
/14
$1,500 per month
- 1 Bed
- 1 Bath
- 540 Sq Ft
- Apartment for Rent
55 Pancake Hollow Rd Unit 3, Highland, NY 12528

Freshly painted one bedroom apartment on the second floor of a multi unit building. Landlord provides heat, hot water, trash and snow removal, and lawn care. Tenant is responsible for their electric, any internet or cable, and propane for cooking. Coin operated washer and dryer located on premises. Centrally located to the Village of Highland, Rail Trail, Walkway Over the Hudson, and Metro North

Kathleen Mackey Summerset Realty

55 Pancake Hollow Rd Unit 3, Highland, NY 12528
$327,000 Sold Nov 20, 2025

283 Hawleys Corners Rd, Highland, NY 12528
- 3 Beds
- 1 Bath
- 1,816 Sq Ft
- Built 1900
Last Sold Summary
- 9% Below List Price
- $180/SF
- 74 Days On Market
Current Estimated Value $342,559

Last Listing Agent Dawn Passante Coldwell Banker Village Green

283 Hawleys Corners Rd, Highland, NY 12528

Est $635,229 Not Listed For Sale

321 Perkinsville Rd, Highland, NY 12528
- 3 Beds
- 2.5 Baths
- 2,214 Sq Ft
- Built 2010
321 Perkinsville Rd, Highland, NY 12528

Last Sold Summary
- 19% Above List Price
- $242/SF
- 32 Days On Market
Last Sold Price $535,000

Last Listing Agent Pamela Kandel

/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
/24

$2,500 per month

Hudson Place

2 Beds

1300 Hudson Place, Highland, NY 12528

Welcome to Hudson Place, where your dream lifestyle becomes a reality. This community offers more than just a place to live - it provides a true sense of belonging and convenience featuring an onsite gym, community room and BBQ area. One of the crowning jewels of this location is its proximity to the Walkway Over the Hudson. Take leisurely strolls or invigorating jogs while relishing the scenic

1300 Hudson Place, Highland, NY 12528
$50,000 Sold Nov 17, 2025

0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719
- Land
- 7.33 Acres
- $6,821 per Acre
Last Sold Summary
- 29% Below List Price
- 154 Days On Market
Last Listing Agent Loretta Wolff NexLvl Real Estate Inc.

0 Yulan-Barryville Rd Unit KEY857000, Highland, NY 12719

Est $594,593 Not Listed For Sale

94 Glen Rock Cir, Highland, NY 12528
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
- Built 2012
94 Glen Rock Cir, Highland, NY 12528

Last Sold Summary
- 15% Above List Price
- $245/SF
- 21 Days On Market
Last Sold Price $515,000

Last Listing Agent JOHN SCARANO Keller Williams Realty

/8
$195,000
- Land
- 22.3 Acres
- $8,744 per Acre
0 Crawford Rd Unit KEY821449, Highland, NY 12528

Beautiful wooded 22.3 acre parcel along quaint Crawford Road just outside of the charming Delaware river hamlet of Barryville. Close to Eldred, Yulan, Barryville, Narrowsburg and the Delaware River.

Rosemarie DeCristofaro

Callicoon Real Estate LLC

(845) 681-6170

0 Crawford Rd Unit KEY821449, Highland, NY 12528
/7
$2,300 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- Apartment for Rent
70 New Paltz Rd Unit 1 B, Highland, NY 12528

Beautiful new 2-bedroom, 1 bath open concept apartment, Fully equipped with sleek stainless-steel appliances in the spacious kitchen with beautiful cabinetry. Hardwood floors throughout the modern floor plan. Big and bright windows creating an airy, sun filled living space. First level with private porch. Lot parking. Located close to New Paltz and 5 miles from Poughkeepsie for easy commute to

Pamela Di Martino Curasi Realty, Inc.

70 New Paltz Rd Unit 1 B, Highland, NY 12528
$559,000 Sold Dec 09, 2025

19 Emerson Terrace, Highland, NY 12528
- 3 Beds
- 3 Baths
- 2,668 Sq Ft
- Built 2021
Last Sold Summary
- $210/SF
- 87 Days On Market
Current Estimated Value $554,507

Last Listing Agent Susan Todd BHHS Hudson Valley Properties

19 Emerson Terrace, Highland, NY 12528

/17
Not Listed For Sale

119 Tuckers Corners Rd, Highland, NY 12528
- 2 Beds
- 1 Bath
- 1,080 Sq Ft
- Built 1982
119 Tuckers Corners Rd, Highland, NY 12528

Last Sold Summary
- $119/SF
- 15 Days On Market
Last Sold Price $129,000

Last Listing Agent Daniel Winn Halter Associates Realty

/16
$159,000
- Land
- 5.05 Acres
- $31,485 per Acre
Lot 1 Zane Grey Way, Highland, NY 12719

Fantastic opportunity to own a prime, buildable property with access to beautiful York Lake. Located in the exclusive private community of York Lake Shores, York Lake is a pristine 103-acre, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. This lovely 5.05 acre lot is as close as one can be to the community’s lake access

Edward Rabon

Compass Greater NY, LLC

(845) 448-8745

Lot 1 Zane Grey Way, Highland, NY 12719
/15

$2,200 - $2,250 per month

Orchard Hills

2 Beds

Orchard Hill Cir, Highland, NY 12528

Explore the ideal sanctuary in Highland, New York! This vibrant community boasts a mix of 2 and 3 bedroom townhouses and 1 bedroom studios. Revel in the convenient proximity to local boutiques, dining establishments, and the full spectrum of Highland's amenities. Furthermore, the nearby rail trail beckons outdoor enthusiasts and nature admirers, creating an exceptional refuge for strolls, jogs,

Orchard Hill Cir, Highland, NY 12528
$365,000 Sold Mar 03, 2025

325 Perkinsville Rd, Highland, NY 12528
- 3 Beds
- 2 Baths
- 1,458 Sq Ft
- Built 1996
Last Sold Summary
- 19% Below List Price
- $250/SF
- 88 Days On Market
Current Estimated Value $391,942

Last Listing Agent Geraldine Gaudioso Century 21 Alliance Rlty Group

325 Perkinsville Rd, Highland, NY 12528

Est $458,926 Not Listed For Sale

625 Milton Turnpike, Highland, NY 12528
- 2 Beds
- 1.5 Baths
- 1,672 Sq Ft
- Built 1920
625 Milton Turnpike, Highland, NY 12528

Last Sold Summary
- 28% Above List Price
- $214/SF
- 39 Days On Market
Last Sold Price $358,000

Last Listing Agent Lori Rheingold

/32
$450,000
- 4 Beds
- 1.5 Baths
- 3,140 Sq Ft
668 State Route 44 55, 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,

Stefan Bolz

Hudson Dwellings Realty

(845) 272-5945

668 State Route 44 55, Highland, NY 12528
/12
$2,600 per month
- 2 Beds
- 2 Baths
- 1,200 Sq Ft
- Apartment for Rent
42 Maple Ave Unit 2, Highland, NY 12528

Beautiful country setting, just up the street from the The Ridge by Mill House (previously THe Gunk House Restaurant) in Clintondale, houses this picturesque stately Victorian three family home. The available two bedroom offers a full galley kitchen, formal dining room, spacious living room both with beamed ceiling, half bath and main bedroom and full bath on the main level. The second level

Laurie Dellavilla Miller Professional Realty Group

42 Maple Ave Unit 2, Highland, NY 12528
$620,000 Sold Jan 05, 2026

93 Glen Rock Cir, Highland, NY 12528
- 4 Beds
- 2.5 Baths
- 2,270 Sq Ft
- Built 2008
Last Sold Summary
- 9% Above List Price
- $273/SF
- 26 Days On Market
Current Estimated Value $568,513

Last Listing Agent Randy Spiesman Weichert REALTORS

93 Glen Rock Cir, Highland, NY 12528

/35
Est $617,388 Not Listed For Sale

135 Chapel Hill Rd, Highland, NY 12528
- 3 Beds
- 2.5 Baths
- 2,650 Sq Ft
- Built 2018
135 Chapel Hill Rd, Highland, NY 12528

Last Sold Summary
- 13% Above List Price
- $206/SF
- 31 Days On Market
Last Sold Price $545,000

Last Listing Agent Lindsay Stevens eXp Realty

/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
/15

$1,500 per month

Highland Crossing

1 Bed

3501 9w Route, Highland, NY 12528

Welcome to Highland Crossing Community in Highland, New York! Our newly renovated one-bedroom apartments, nestled near the charming village of Highland, provide cozy living for those who love small-town life. Each unit is modern and comfortable, offering a touch of rustic charm. Located near the village, you'll have easy access to local shops, restaurants, and community events, while enjoying the

3501 9w Route, Highland, NY 12528
/38
$380,000 Sold Oct 03, 2025

399 New Paltz Rd, Highland, NY 12528
- 4 Beds
- 3 Baths
- 2,700 Sq Ft
- Built 1992
Last Sold Summary
- 9% Above List Price
- $141/SF
- 18 Days On Market
Current Estimated Value $381,170

Last Listing Agent Dawn Passante Coldwell Banker Village GreenN

399 New Paltz Rd, Highland, NY 12528

Est $126,243 Not Listed For Sale

10 Sollazzo Ln, Highland, NY 12528
10 Sollazzo Ln, Highland, NY 12528

Last Sold Summary
- 5% Above List Price
- 234 Days On Market
Last Sold Price $120,000

Last Listing Agent Margareta Schmoll Curasi Realty, Inc.

/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
/9
$1,500 per month
- 0.5 Baths
- 750 Sq Ft
- Apartment for Rent
199 State Route 299 Unit 103, Highland, NY 12528

Prime Route 299 Commercial Space – High Visibility | Move-In ReadyRare opportunity to secure a high-exposure commercial space on busy Route 299 in Highland — perfect for a salon, professional office, boutique retail shop, or wellness practice.If you’re looking for visibility, easy access, and a manageable space to grow your business, this is it.Features include:• Private

Ashley Olson Minard eXp Realty

199 State Route 299 Unit 103, Highland, NY 12528
$315,000 Sold Aug 04, 2025

7 Sunny Brook Cir, Highland, NY 12528
- 3 Beds
- 1.5 Baths
- 1,160 Sq Ft
- Built 1974
Last Sold Summary
- 15% Above List Price
- $272/SF
- 14 Days On Market
Current Estimated Value $313,530

Last Listing Agent Daniel Amone BHHS Hudson Valley Properties

7 Sunny Brook Cir, Highland, NY 12528

Est $225,500 Not Listed For Sale

9 Elbow Ln, Highland, NY 12528
9 Elbow Ln, Highland, NY 12528

Last Sold Summary
- 7% Above List Price
- 229 Days On Market
Last Sold Price $210,000

Last Listing Agent Christopher Acuti RE/MAX

Showing Results 1 - 40, Page 1 of 18

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