Highland, NY Homes

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  /32

  Est $363,059

  Not Listed For Sale

  116 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,270 Sq Ft
  • Built 1988

  116 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 8 Days On Market

  Last Listing Agent Antonio Parrotta Coldwell Banker Village GreenN
• 

  

  

  /24

  $530,900

  • 3 Beds
  • 3 Baths
  • 2,050 Sq Ft

  452 Vineyard Ave, Highland, NY 12528

  This home is completely remodeled. New roof, new siding new windows new Insulation all new electrical all new plumbing. All new flooring throughout the home. Brand new kitchen with quartz countertops, completely remodeled bathrooms. Brand new central air unit brand new furnace ,brand new hot water heater. This Home is just minutes away from the mid Hudson Bridge and the Minnewaska mountains.

  Derek Greene Greene Realty Group

  452 Vineyard Ave, Highland, NY 12528
• 

  $342,500

  Sold Aug 04, 2026

  128 Vineyard Ave Unit 209, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 1,116 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Above List Price
  • $307/SF
  • 87 Days On Market

  Last Listing Agent Andrea Babcock Onyx Property Management LLC

  128 Vineyard Ave Unit 209, Highland, NY 12528
• 

  Est $316,880

  Not Listed For Sale

  82 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,396 Sq Ft
  • Built 1988

  82 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Philip Bisesto HomeSmart Homes & Estates
• 

  

  

  /15

  $135,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,172 Sq Ft

  499 State Route 299, Highland, NY 12528

  Well maintained 2-Bedroom Mobile Home in Desirable Highland Woods Community - Welcome to easy, comfortable living in this delightful 2-bedroom, 2-bathroom home located in the peaceful Highland Woods Mobile Home Park. Featuring modern laminate flooring throughout, this move-in-ready residence offers a bright and functional layout. Highlights include a versatile three-season room-ideal for a

  JoAnn Ellis Summerset Realty

  499 State Route 299, Highland, NY 12528
• 

  $375,000

  Sold May 26, 2026

  493 State Route 44-55, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 2,076 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Above List Price
  • $181/SF
  • 23 Days On Market

  Last Listing Agent Stacie Romanelli BHHS Hudson Valley Properties

  493 State Route 44-55, Highland, NY 12528
• 

  Est $356,901

  Not Listed For Sale

  80 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,270 Sq Ft
  • Built 1988

  80 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Kristen Zigouras eXp Realty
• 

  

  /32

  $485,000

  $114K PRICE DROP

  • 4 Beds
  • 2.5 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 mountainviews. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restorationor 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
• 

  

  /37

  $491,000

  Sold Oct 31, 2025

  258 Martin Ave, Highland, NY 12528

  • 5 Beds
  • 4 Baths
  • 2,366 Sq Ft
  • Built 1983

  Last Sold Summary

  • 1% Below List Price
  • $208/SF
  • 74 Days On Market

  Current Estimated Value $530,614

  Last Listing Agent Hayes Clement Compass Greater New York, LLC

  258 Martin Ave, Highland, NY 12528
• 

  

  /19

  Est $373,769

  Not Listed For Sale

  72 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,400 Sq Ft
  • Built 2018

  72 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Dawn Passante Coldwell Banker Village GreenN
• 

  

  /13

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 208, Highland, NY 12528

  Welcome to Highbridge Crossing, a newly established 20-unit condominium community built in 2018, where modern industrial design, energy efficiency, and convenient Hudson Valley living come together. Thoughtfully constructed with contemporary finishes and ideally situated directly along the Hudson Valley Rail Trail, offering convenient access to the Walkway Over the Hudson—one of the region’s most

  Alejandra Filiciotto Corcoran Country Living

  128 Vineyard Ave Unit 208, Highland, NY 12528
• 

  $450,000

  Sold Apr 17, 2026

  10 Carly Dr, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • Built 1998

  Last Sold Summary

  • $315/SF
  • 103 Days On Market

  Current Estimated Value $467,088

  Last Listing Agent Megan Krusen eXp Realty

  10 Carly Dr, Highland, NY 12528
• 

  Est $386,879

  Not Listed For Sale

  253 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 2.5 Baths
  • 1,396 Sq Ft
  • Built 1987

  253 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Cindy Schoenleber HomeSmart Homes & Estates
• 

  

  /5

  $25,000

  Pending

  • Land
  • 1.03 Acres
  • $24,272 per Acre

  0 Park Ln Unit KEY984771, Highland, NY 12792

  BUILDING LOT IN YULAN, NY - This is a cleared one acre parcel with the driveway and parking area installed. Electric is at the road and can easily be brought into the site. This little neighborhood is tucked away in the country with a ball field just down the road, makes this a special location for a new home. Approximately 2.5 hrs from NYC, makes this special property a very easy commute. Close

  Caroline Akt Caroline Akt Realty LLC

  0 Park Ln Unit KEY984771, Highland, NY 12792
• 

  

  /37

  $535,000

  Sold Apr 16, 2026

  132 Weeds Mill Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,488 Sq Ft
  • Built 1974

  Last Sold Summary

  • 8% Above List Price
  • $360/SF
  • 17 Days On Market

  Current Estimated Value $518,016

  Last Listing Agent HARRY HELEOTIS Illustrated Properties Group

  132 Weeds Mill Rd, Highland, NY 12528
• 

  Est $336,713

  Not Listed For Sale

  93 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,047 Sq Ft
  • Built 1988

  93 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent DANA LYNN HERRINGTON Dana Lynn Real Estate, LLC
• 

  

  /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 rocking-chair

  Artur Galustyan Century 21 Alliance Rlty Group

  346 Crescent Ave, Highland, NY 12528
• 

  $50,000

  Sold Oct 27, 2025

  Lot#26 Timber Lake Dr, Highland, NY 12792

  • Land
  • 5.63 Acres
  • $8,881 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 51 Days On Market

  Last Listing Agent Jane Panico Realty Promotions Inc

  Lot#26 Timber Lake Dr, Highland, NY 12792
• 

  Est $373,282

  Not Listed For Sale

  167 Sterling Place, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,302 Sq Ft
  • Built 1998

  167 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Suzanne DeCosta Houlihan Lawrence Inc.
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  /47

  $474,000

  • 3 Beds
  • 2 Baths
  • 1,492 Sq Ft

  4 Alex Ct, Highland, NY 12528

  Delightful Ranch in welcoming Mountainside Woods features an inviting rocking-chair front porch overlooking neighbor-friendly streets with sidewalks. Mountainside offers the perfect blend of community and location, nestled in nature at the foot of beautiful Illinios Mtn with easy access to numerous walking and hiking trails, parks, farmers markets, and area attractions. This popular Taconic model

  Susan Todd BHHS Hudson Valley Properties

  4 Alex Ct, Highland, NY 12528
• 

  $315,000

  Sold Dec 01, 2025

  39 Sunny Brook Cir, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,220 Sq Ft
  • Built 1976

  Last Sold Summary

  • $258/SF
  • 13 Days On Market

  Current Estimated Value $341,865

  Last Listing Agent Dawn Passante Coldwell Banker Village Green

  39 Sunny Brook Cir, Highland, NY 12528
• 

  

  /21

  Est $373,122

  Not Listed For Sale

  169 Sterling Place, Highland, NY 12528

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft
  • Built 1998

  169 Sterling Place, Highland, NY 12528

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Dylan Taft Taft Street Realty, Inc.
• 

  

  /6

  $110,000

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

  748 State Route 44 55, Highland, NY 12528

  BOHA 2.1-acre parcel ready to build and approved for a 4-bedroom home in beautiful Ulster County. Ideally located just 1 mile from Rocking Horse Ranch Resort, with convenient access to the Mid-Hudson Bridge and NY State Thruway. This exceptional property offers the perfect blend of seclusion and accessibility. The approved homesite is nestled well back from the road, creating a peaceful, secluded

  Darci Russo KW MidHudson

  748 State Route 44 55, Highland, NY 12528
• 

  $100,000

  Sold May 15, 2026

  0 Haviland Rd Unit KEY899872, Highland, NY 12528

  • Land
  • 1.5 Acres
  • $66,667 per Acre

  Last Sold Summary

  • 33% Below List Price
  • 191 Days On Market

  Last Listing Agent Anthony DeGelormo Century 21 Alliance Rlty Group

  0 Haviland Rd Unit KEY899872, Highland, NY 12528
• 

  Est $736,827

  Not Listed For Sale

  6 Wellington Place, Highland, NY 12528

  • 4 Beds
  • 2.5 Baths
  • 2,661 Sq Ft
  • Built 2005

  6 Wellington Place, Highland, NY 12528

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Danielle Oliva Serhant LLC
• 

  

  /12

  $400,000

  • 5 Beds
  • 3 Baths
  • 2,700 Sq Ft

  19-21 Church St, Highland, NY 12528

  Village of Highland three family comprised of (2) two bedroom units and (1) one bedroom unit. Spacious apartments with well proportioned rooms. Natural gas for heat & hot water. Separate utilities & off street parking. Centrally located with easy access to village amenities, Route 9W & Mid-Hudson Bridge.

  Dan Axtmann BHHS Hudson Valley Properties

  19-21 Church St, Highland, NY 12528
• 

  

  /6

  $248,000

  Sold Feb 01, 2026

  9 Lumen Ln, Highland, NY 12528

  • Land
  • 6.2 Acres
  • $40,000 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 223 Days On Market

  Last Listing Agent Theodore Chazkel BHHS HUDSON VALLEY PROP-NP

  9 Lumen Ln, Highland, NY 12528
• 

  Est $413,791

  Not Listed For Sale

  235 Perkinsville Rd, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1930

  235 Perkinsville Rd, Highland, NY 12528

  Last Sold Summary

  • 60 Days On Market

  Last Listing Agent Kismet Johnson eXp Realty
• 

  

  /32

  $459,000

  $30K PRICE DROP 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 Houlihan Lawrence Inc.

  57 Mayer Dr, Highland, NY 12528
• 

  $308,000

  Sold Aug 13, 2026

  549 Gregory Ct Unit 68, Highland, NY 12528

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $326/SF
  • 17 Days On Market

  Current Estimated Value $298,731

  Last Listing Agent Syndi Acampora eXp Realty

  549 Gregory Ct Unit 68, Highland, NY 12528
• 

  Est $398,412

  Not Listed For Sale

  231 Perkinsville Rd, Highland, NY 12528

  • 2 Beds
  • 1.5 Baths
  • 1,476 Sq Ft
  • Built 1954

  231 Perkinsville Rd, Highland, NY 12528

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Kismet Johnson eXp Realty
• 

  $481,900

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  Taconic Home Plan at Mountainside Woods, Highland, NY 12528

  Meadow Creek Development Builder

  2 Benjamin Dr Unit 42035521, Highland, NY 12528
• 

  $329,000

  Sold Oct 09, 2025

  37 Maple Ave, Highland, NY 12528

  • 3 Beds
  • 2.5 Baths
  • 1,121 Sq Ft
  • Built 1800

  Last Sold Summary

  • $293/SF
  • 78 Days On Market

  Current Estimated Value $338,585

  Last Listing Agent Meyer Stoessel Keller Williams Hudson Valley

  37 Maple Ave, Highland, NY 12528
• 

  Est $429,983

  Not Listed For Sale

  325 Perkinsville Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,458 Sq Ft
  • Built 1996

  325 Perkinsville Rd, Highland, NY 12528

  Last Sold Summary

  • 88 Days On Market

  Last Listing Agent Geraldine Gaudioso Century 21 Alliance Rlty Group
• 

  

  /46

  $575,000

  $24K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft

  105 S Chapel Hill Rd, Highland, NY 12528

  Welcome to this spacious and inviting ranch home in the heart of Highland, conveniently located near the iconic Mid-Hudson Bridge and just minutes from shopping, restaurants, commuter routes, and all that the Hudson Valley has to offer. The main level features three comfortable bedrooms and a bright, open layout designed for everyday living. The spacious kitchen offers abundant cabinet and

  Dawn Passante Coldwell Banker Village GreenN

  105 S Chapel Hill Rd, Highland, NY 12528
• 

  $362,000

  Sold Jul 07, 2026

  609 New Paltz Rd, Highland, NY 12528

  • 3 Beds
  • 1 Bath
  • 1,448 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Below List Price
  • $250/SF
  • 68 Days On Market

  Current Estimated Value $373,479

  Last Listing Agent Kyla Thomas Howard Hanna Rand Realty

  609 New Paltz Rd, Highland, NY 12528
• 

  

  /33

  Est $433,519

  Not Listed For Sale

  441 Vineyard Ave, Highland, NY 12528

  • 4 Beds
  • 2 Baths
  • 1,919 Sq Ft
  • Built 1950

  441 Vineyard Ave, Highland, NY 12528

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Leigh Wagner-Quintana Past Member
• 

  

  /42

  $799,000

  • 5 Beds
  • 5 Baths

  239-241 Fosler Rd, Highland, NY 12528

  Beautiful well maintained multi-family property offer, a rare opportunity for both owner-occupant & investors. Two houses that sit on 15 acres with endless revenue generating opportunities. The deed allows for the property to be subdivided & extending the private road along northern property line. The main house is a single family that features 2 bedrooms, 2.5 bathrooms with a full finished

  Maurice Bailey Neighborhood Assistance Corp

  239-241 Fosler Rd, Highland, NY 12528
• 

  $724,500

  Sold Jun 04, 2026

  668 N Chodikee Lake Rd, Highland, NY 12528

  • 4 Beds
  • 1.5 Baths
  • 2,244 Sq Ft
  • Built 1820

  Last Sold Summary

  • 13% Above List Price
  • $323/SF
  • 27 Days On Market

  Current Estimated Value $717,223

  Last Listing Agent Hayes Clement Compass Greater NY, LLC

  668 N Chodikee Lake Rd, Highland, NY 12528
• 

  

  /29

  Est $390,945

  Not Listed For Sale

  124 Half Moon Rd, Highland, NY 12528

  • 3 Beds
  • 2 Baths
  • 1,681 Sq Ft
  • Built 1962

  124 Half Moon Rd, Highland, NY 12528

  Last Sold Summary

  • 56 Days On Market

  Last Listing Agent Paige McClintock Howard Hanna Rand Realty

Showing Results 241 - 280, Page 7 of 18