Highland, NY Homes

/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
/36

$1,350 - $1,875 per month

Discover Peaceful Living at Black Creek Ap...

Studio-2 Beds

30 Black Creek Rd, Highland, NY 12528

Experience a new chapter in refined living at 30 Black Creek Apartments, nestled in the peaceful beauty of Esopus, New York. Now under new ownership and professional management, this reimagined community is committed to delivering exceptional service and an elevated living experience.Set against the backdrop of the Hudson Valley’s natural charm, 30 Black Creek offers charming and peaceful

30 Black Creek Rd, Highland, NY 12528
$689,901 Sold Jul 28, 2025
- 2,661 Sq Ft
- $259/SF
- 30 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2005
6 Wellington Place, Highland, NY 12528

Gorgeous, newly updated center hall colonial, adorned with a picturesque, winding stone walkway, and lush landscaping, leading to front porch with trex decking. As you open the front door, you're greeted by an open concept floor plan. This home is situated on almost 2 acres of privacy, on a cul de sac, surrounded by lush forest, and a backyard to die for! Inground "L" shaped pool with new cabana,

Danielle Oliva RE/MAX Classic Realty

6 Wellington Place, Highland, NY 12528

/20
Est $424,373 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,374 Sq Ft
195 Pancake Hollow Rd, Highland, NY 12528

195 Pancake Hollow Rd, Highland, NY 12528

/21
$290,000
- 2 Beds
- 1 Bath
- 1,200 Sq Ft
19 North Rd, Highland, NY 12528

Fully available, and completely renovated, this home is perfect! Starting with the front porch, where you can sit and relax, work, nap, chat, etc. and enjoy the peaceful surroundings. Enter the home on the ground floor. From the minute you walk in, you'll notice how light and bright things are. On this level the laundry room as well as a few additional finished spaces that can be used for a

Nicole Gold

RE/MAX Benchmark Realty Group

(845) 683-5805

19 North Rd, Highland, NY 12528
/12
$3,125 per month
- 3 Beds
- 1 Bath
- 1,200 Sq Ft
- House for Rent
121 North Rd, Highland, NY 12528

Nestled in the heart of Highland, NY, this recently updated three bedroom, one bath home combines timeless character with modern functionality. The sunlit living room offers generous space for both relaxation and entertaining, while the fully renovated kitchen features sleek stainless steel appliances, ample cabinetry, and expansive counter space perfect for everyday cooking or hosting. Step

Matthew Cave Hudson Property Services, LLC

121 North Rd, Highland, NY 12528
$335,000 Sold Jul 28, 2025
- 1,360 Sq Ft
- $246/SF
- 82 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1974
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

/33
Est $411,805 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,340 Sq Ft
110 Weeds Mill Rd, Highland, NY 12528

110 Weeds Mill Rd, Highland, NY 12528

/16
$179,000
- Land
- 5 Acres
- $35,446 per Acre
Lot 1 Zane Grey Way, Highland, NY 12719

Fantastic opportunity to own a prime, buildable lake access property in Sullivan County’s beautiful York Lake in the exclusive, private community of York Lake Shores. York Lake is a 103-acre pristine, natural, non-motor boat, spring-fed lake that is only accessible to residents within the two communities that surround it. While not lakefront, this 5.05 acre lot is the closest one can be

Edward Rabon

Century 21 Geba Realty

(845) 622-8776

Lot 1 Zane Grey Way, Highland, NY 12719
/35

$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
$526,000 Sold Jul 24, 2025
- 2,186 Sq Ft
- $241/SF
- 19 Days On Market
- 3 Beds
- 4 Baths
- Built 2017
6 Emerson Terrace, Highland, NY 12528

This beautiful home blends luxury and practicality throughout. The first floor features a chef-inspired kitchen with stainless steel appliances, abundant cabinetry, and a 6' island with quartz countertops. The adjoining living room boasts a two-story ceiling and a double-sided gas fireplace, creating an inviting, open atmosphere. The spacious first-floor master suite offers a luxury shower with a

John Olivero Keller Williams Realty

6 Emerson Terrace, Highland, NY 12528

Est $582,540 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,478 Sq Ft
288 Baileys Gap Rd, Highland, NY 12528

288 Baileys Gap Rd, Highland, NY 12528

/7
$195,000
- Land
- 22 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 and the Delaware River.

Rosemarie DeCristofaro

Callicoon Real Estate LLC

(845) 671-5361

0 Crawford Rd Unit KEY821449, Highland, NY 12528
/31
$2,350 per month
- 2 Beds
- 2.5 Baths
- 1,300 Sq Ft
- Apartment for Rent
794 South St, Highland, NY 12528

Welcome to 794 South Street Unit #2 — a modern townhouse-style apartment built in 2017 and thoughtfully refreshed for today’s renter. This spacious 2-bedroom, 2.5-bath home spans two floors and offers the perfect blend of comfort, convenience, and privacy. Enjoy ground-level entry, a generous parking area, and your own private back patio that opens to a peaceful yard surrounded by light woods —

Felix Pena RE/MAX Benchmark Realty Group

794 South St, Highland, NY 12528
/19
$285,000 Sold Jul 23, 2025
- 1,470 Sq Ft
- $194/SF
- 52 Days On Market
- 2 Beds
- 1.5 Baths
- Built 1950
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

Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,768 Sq Ft
32 Timber Lake Dr, Highland, NY 12792

32 Timber Lake Dr, Highland, NY 12792

/9
$39,900
- Land
- 2.82 Acres
- $14,149 per Acre
Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791

Looking for a spot to build your dream home, look no further! This nice mostly level property is wooded with some open space. There is 288' of road frontage and the property is approximately 400' deep. Located close to the towns of Barryville and Yulan. Close to the Delaware River. Land is selling quickly, so schedule your appointment today!

Dawn Curreri

EAGLE VALLEY REALTY

(845) 524-9107

Lot 57.1 Yulan-Barryville Rd, Highland, NY 12791
/35

$1,500 - $1,795 per month

Brookside Apartments

1-2 Beds

210 Vineyard Ave, Highland, NY 12528

Located minutes from the Mid-Hudson Bridge, 4 miles from Vassar Hospital. Quiet brookside location. One mile from the quaint shops in the town of Highland.

210 Vineyard Ave, Highland, NY 12528
/19
$325,000 Sold Jul 22, 2025
- 1,296 Sq Ft
- $251/SF
- 151 Days On Market
- 3 Beds
- 1 Bath
- Built 1958
183 Pancake Hollow Rd, Highland, NY 12528

Life is easy in this sweet single level ranch style home. The covered front porch is perfect for relaxing. Inside enjoy the large living room with bay window and fireplace just off the updated kitchen. Entertain friends in the dining room which is open to additional living space. Just off the dining room is a screened in porch for comfortable summer nights. The lower level features full basement

Dawn Passante Coldwell Banker Village GreenN

183 Pancake Hollow Rd, Highland, NY 12528

Est $539,621 Not Listed For Sale
- 4 Beds
- 3 Baths
- 2,197 Sq Ft
274 Fosler Rd, Highland, NY 12528

274 Fosler Rd, Highland, NY 12528

/15
$225,000
- 1 Bed
- 1 Bath
- 762 Sq Ft
534 New Paltz Rd, Highland, NY 12528

Move-in Ready Gem-Perfect for Easy Living in Highland, NYStep into this completely renovated 1-Bedroom, 1-Bath home designed for comfort and convenience. The entire house has been fully renovated featuring New Septic System, New Roof, New Electrical, New Plumbing, New Washer/Dryer hook up, New water heater, New Electrical panel 200 amp, New Sheetrock, New wall and ceiling insulation, New

Sandra Rosario Hello Dolly Real Estate

534 New Paltz Rd, Highland, NY 12528
/12
$2,200 per month
- 2 Beds
- 1 Bath
- 1,654 Sq Ft
- Apartment for Rent
8 Marie Unit 2, Highland, NY 12528

Picaresque Country Charmer is set on 2 plus acres of lush greenery. Updated and fresh appeal makes this spacious 2nd floor 2 Bedrooms a great choice. if you're looking to relocate this summer, you don't want to miss this one. offers an eat in kitchen with nook, living room, pantry and updated full bath. Each apartment has its own driveway and plenty of extra parking for guests in the common

Michelle Ayala BHHS HUDSON VALLEY PROP-L

8 Marie Unit 2, Highland, NY 12528
/21
$410,000 Sold Jul 21, 2025
- 1,683 Sq Ft
- $244/SF
- 69 Days On Market
- 3 Beds
- 1.5 Baths
- Built 1987
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

Est $629,503 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,000 Sq Ft
5 Clearwater Rd, Highland, NY 12528

5 Clearwater Rd, Highland, NY 12528

/37
$495,000
- 5 Beds
- 4 Baths
- 2,366 Sq Ft
258 Martin Ave, Highland, NY 12528

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 roomy, one-level home featuring three bedrooms and two

Hayes Clement Compass Greater New York, LLC

258 Martin Ave, Highland, NY 12528
/8

$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
/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 $612,693 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 2,214 Sq Ft
321 Perkinsville Rd, Highland, NY 12528

321 Perkinsville Rd, Highland, NY 12528

/29
$399,000
- 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
/23
$2,750 per month
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
- Apartment for Rent
140 Pancake Hollow Rd Unit A, Highland, NY 12528

Available September 1st! Gorgeous 3 bedroom, 2.5 bathroom, 1500 sq ft rental located in Highland. Beautiful home with covered front porch and a back patio where the outdoors can be enjoyed. The first floor of the rental has an open concept living room, modern kitchen, laundry area with hook-ups, and a half bath. The second floor features three bedrooms, two full baths, including a primary suite

Marisa Bellacicco Century 21 Alliance Rlty Group

140 Pancake Hollow Rd Unit A, 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

Est $524,431 Not Listed For Sale
- 3 Beds
- 2.5 Baths
- 1,682 Sq Ft
9 Emerson Terrace, Lloyd, NY 12528

9 Emerson Terrace, Lloyd, NY 12528

/33
$475,000
- 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
/9

$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
/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 $552,147 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,100 Sq Ft
94 Glen Rock Cir, Highland, NY 12528

94 Glen Rock Cir, Highland, NY 12528

/19
$469,000
- 3 Beds
- 3 Baths
- 1,656 Sq Ft
12 Summit Dr, Highland, NY 12792

Escape to your own private sanctuary! This stunning retreat sits on 5.5 acres of pristine woodland within the exclusive gated community of Timber Lake Estates. Paved roads wind through the community, leading you around the sparkling centerpiece - Timber Lake itself.Four seasons of recreation await right outside your door. Summer brings endless lake adventures: fishing from the shore,

Joann Alvis Coldwell Banker Village GreenN

12 Summit Dr, Highland, NY 12792
/28
$3,000 per month
- 6 Beds
- 3 Baths
- 1,316 Sq Ft
- House for Rent
269 Pancake Hollow Rd, Highland, NY 12528

This beautifully renovated 6-bedroom, 3-bath home offers the perfect blend of space, comfort, and convenience—set on over 7 peaceful acres with plenty of room to relax, explore, and enjoy nature. Inside, you’ll find an updated eat-in kitchen, a formal dining room, and a spacious living area complete with a wood-burning stove and luxury vinyl plank flooring. The home also features three fully

Margaret Thorne Keller Williams Hudson Valley

269 Pancake Hollow Rd, 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

/17
Not Listed For Sale
- 2 Beds
- 1 Bath
- 1,080 Sq Ft
119 Tuckers Corners Rd, Highland, NY 12528

119 Tuckers Corners Rd, Highland, NY 12528

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