Highland, NY Homes

/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

Est $654,429 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 2,713 Sq Ft
131 Baileys Gap Rd, Highland, NY 12528

131 Baileys Gap Rd, Highland, NY 12528

/38
$475,000 Pending
- 3 Beds
- 1.5 Baths
- 1,633 Sq Ft
224 Martin Ave, Highland, NY 12528

Welcome to this charming ranch style home featuring 3 cozy bedrooms. The primary bedroom has a large full bath, perfect for comfortable living. As you step inside you will be greeted by beautiful wood 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 spot for casual dining or

Dawn Passante Coldwell Banker Village Green

224 Martin 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 $759,194 Not Listed For Sale
- 3 Beds
- 4 Baths
- 3,275 Sq Ft
326 Perkinsville Rd, Highland, NY 12528

326 Perkinsville Rd, Highland, NY 12528

/30
$450,000 Pending
- 4 Beds
- 2 Baths
- 2,121 Sq Ft
723 New Paltz Rd, Highland, NY 12528

First Time Ever on the Market, this wonderful 4 bedroom home! Welcome to 723 New Paltz Road — Lovingly maintained by the original owners, this charming home is being offered for sale for the very first time. Set on a spacious lot with a large deck overlooking a level backyard. The property combines comfort, convenience, and untapped potential.Inside, you'll find a warm and inviting layout

Christopher Baker K. Fortuna Realty, Inc.

723 New Paltz Rd, 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

/49
Est $642,692 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,658 Sq Ft
30 Grand St, Highland, NY 12528

30 Grand St, Highland, NY 12528

/50
$450,000 Pending
- 5 Beds
- 4 Baths
- 1,890 Sq Ft
155 Tuckers Corners Rd, Highland, NY 12528

Welcome to 155 Tuckers Corners Rd – a charming 1928 Craftsman Bungalow nestled on 3.37 private acres in Highland. This spacious home offers 5 bedrooms and 1.5 bathrooms in the main residence, along with a walk-out basement featuring a full in-law suite complete with its own kitchen, living room, bedroom, and full bath. Please note: the square footage does not include the finished lower-level

Anais O'Connor Compass Greater NY, LLC

155 Tuckers Corners Rd, 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 $576,737 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,470 Sq Ft
25 Lauretta Dr, Highland, NY 12528

25 Lauretta Dr, Highland, NY 12528

/36
$425,000 Pending
- 4 Beds
- 1.5 Baths
- 1,449 Sq Ft
136 Chapel Hill Rd, Highland, NY 12528

Beautifully blending timeless character with modern upgrades, this thoughtfully updated four-bedroom farmhouse offers the perfect balance of charm, comfort, and convenience. Original woodwork, wide-board flooring, and classic architectural details preserve the home's historic soul, while a series of recent renovations enhance everyday living. The fully updated kitchen and dining room are designed

Sally Sprogis Four Seasons Sotheby's Int'l R

136 Chapel Hill Rd, 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

/26
Est $592,709 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,400 Sq Ft
21 Spring Meadow Ct, Highland, NY 12528

21 Spring Meadow Ct, Highland, NY 12528

/27
$499,999 Pending
- 3 Beds
- 2 Baths
- 1,560 Sq Ft
290 Tuckers Corners Rd, Highland, NY 12528

Discover the perfect blend of comfort, convenience, and potential in this well-maintained ranch-style home, built just eight years ago and nestled on 15 subdividable, buildable acres in Highland, NY. Whether you’re a builder, investor, or simply seeking a peaceful retreat with room to expand, this property is an exceptional find. The move-in ready home features central air, a heat pump, and a

Virginia Corbett eXp Realty

290 Tuckers Corners Rd, 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

/27
Est $758,300 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,657 Sq Ft
19 Amanda Cir, Highland, NY 12528

19 Amanda Cir, Highland, NY 12528

/32
$459,000 Pending
- 3 Beds
- 2 Baths
- 2,418 Sq Ft
57 Mayer Dr, Highland, NY 12528

Stunning Contemporary Split level. The perfect home for entertaining. Open concept living room, kitchen, dining area. Hardwood floors as seen. All new carpeting in bedrooms, Great room, and finished basement. Two fireplaces, one woodburning in family room, gas fireplace in Great room. Multi-level decks overlooking lush backyard with a woodburning pizza oven, concrete pad perfect for firepit. A

CAROLYN DE MICHELE

57 Mayer Dr, 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

Est $425,045 Not Listed For Sale
- 5 Beds
- 2 Baths
- 2,344 Sq Ft
548 South St, Highland, NY 12528

548 South St, Highland, NY 12528

/42
$419,000 Under Contract
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
20 Lauretta Dr, Highland, NY 12528

Tucked away on a quiet dead-end road, set high with scenic mountain views, this well-kept Raised Ranch is ready for your next chapter in the Hudson Valley. Freshly painted and move-in ready, the home offers 3 bedrooms, 2 bathrooms, a wood-burning fireplace, and a fenced-in backyard. The updated kitchen and spacious, finished lower level—with oversized windows framing the views—provide comfort and

Peter Ilani BHHS HUDSON VALLEY PROP-R

20 Lauretta Dr, Highland, NY 12528
/31
$425,000 Sold Jul 08, 2025
- 1,444 Sq Ft
- $294/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 $463,658 Not Listed For Sale
- 4 Beds
- 3 Baths
- 1,750 Sq Ft
799 State Route 44 55, Highland, NY 12528

799 State Route 44 55, Highland, NY 12528

/25
$950,000
- 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 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 home with two bedrooms and one full bathroom per unit for a total of around 1,125 sq ft. Both homes are fully occupied and built

Mi Ryoung Chong HANMI REALTY

10-32 S Roberts Rd, Highland, NY 12528
/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

/11
Est $414,621 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,420 Sq Ft
269 Tuckers Corners Rd, Highland, NY 12528

269 Tuckers Corners Rd, Highland, NY 12528

/26
$500,000
- Land
- 97 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
$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

Est $356,510 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,152 Sq Ft
6 Mandia Ln, Highland, NY 12528

6 Mandia Ln, Highland, NY 12528

/13
$180,000
- Land
- 16 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
/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

/2
Est $436,649 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,518 Sq Ft
359 Crescent Ave, Highland, NY 12528

359 Crescent Ave, Highland, NY 12528

/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
/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

/28
Est $243,008 Not Listed For Sale
- 2 Beds
- 1 Bath
- 895 Sq Ft
355 Crescent Ave, Highland, NY 12528

355 Crescent Ave, Highland, NY 12528

/25
$375,000
- 2 Beds
- 1 Bath
- 1,050 Sq Ft
27 Amato Ln, Highland, NY 12528

Tucked away on a peaceful dead-end road in Highland, this inviting 2-bedroom, 1-bath home offers the perfect blend of charm, updates, and convenience. Whether you're searching for a starter home or a weekend retreat, this property checks all the boxes. The main level welcomes you with an open layout, rustic exposed beams, and a stylishly renovated kitchen featuring sleek soapstone countertops.

Jacob Cohen eXp Realty

27 Amato Ln, Highland, NY 12528
/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

/16
Est $448,825 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,810 Sq Ft
397 Crescent Ave, Highland, NY 12528

397 Crescent Ave, Highland, NY 12528

/6
$235,000
- Land
- 11 Acres
- $21,364 per Acre
TBD Hawleys Corners Rd, Highland, NY 12528

11 acres offering privacy and potential. The land is ideal for building a secluded estate, nature retreat located on a country road yet close to Route 299 leading to NYS Thruway. Mid Hudson Bridge 5 miles away. The parcels break down as follows:Parcel 1: 3.5 acresParcel 2: 4 acresParcel 3: 3.7 acresKey Features:Peaceful rural setting with minimal trafficSurrounded by woods

Dawn Passante Coldwell Banker Village GreenN

TBD Hawleys Corners Rd, 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

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