Highland Mills, NY Homes

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  /43

  $949,000

  • 4 Beds
  • 2.5 Baths
  • 3,332 Sq Ft

  19 Bull Mine Rd, Chester, NY 10918

  Set on 2.3 acres in Chester, this impressive property offers space, versatility, and scenic surroundings. The residence features approximately 3,332 square feet of living space with 4 bedrooms, 2 full baths and 1 half bath, thoughtfully designed for comfortable everyday living and entertaining. Interior highlights include generously sized living areas, a fireplace, abundant natural light, and

  James Cosenza BHG Real Estate Green Team

  19 Bull Mine Rd, Chester, NY 10918
• 

  $750,000

  Sold Apr 27, 2026

  15 Cranberry Dr, Highland Mills, NY 10930

  • 5 Beds
  • 3 Baths
  • 4,136 Sq Ft
  • Built 1978

  Last Sold Summary

  • $181/SF
  • 59 Days On Market

  Current Estimated Value $747,097

  Last Listing Agent Rosemarie Morello KW Hudson Valley United

  15 Cranberry Dr, Highland Mills, NY 10930
• 

  Est $448,812

  Not Listed For Sale

  8 Hill Ave, Highland Mills, NY 10930

  • 4 Beds
  • 2 Baths
  • 1,538 Sq Ft
  • Built 1920

  8 Hill Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Nathen Singer MK Realty Inc
• 

  

  

  /50

  $575,000

  • 3 Beds
  • 2.5 Baths
  • 2,190 Sq Ft

  2 Buena Vista Terrace, Central Valley, NY 10917

  Welcome to the next chapter of your story. Lovingly maintained and meticulously cared for over the years, this exceptional **3-bedroom, 2.5-bath home** reflects true pride of ownership from the moment you arrive. Ideally located in the heart of Central Valley, it offers the perfect blend of timeless charm, everyday comfort, and one of Orange County's most desirable commuter

  Rosalie Cook Weichert Realtors

  2 Buena Vista Terrace, Central Valley, NY 10917
• 

  $799,000

  Sold Jul 22, 2026

  37 Southfield Falls, Monroe, NY 10950

  • 2 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $372/SF
  • 1 Day On Market

  Current Estimated Value $832,971

  Last Listing Agent Dovid Hoffman MK Realty Inc

  37 Southfield Falls, Monroe, NY 10950
• 

  Est $601,754

  Not Listed For Sale

  49 Pine Hill Rd, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 1972

  49 Pine Hill Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Veronica Rodriguez Keller Williams Realty
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  /50

  $985,000

  $100K PRICE DROP

  • 4 Beds
  • 5 Baths
  • 3,674 Sq Ft

  93 Horton Rd, Washingtonville, NY 10992

  The Jeremiah Horton House, circa 1700s, represents a singular opportunity to steward a piece of Hudson Valley history. Crafted by renowned 18th-century stonemason Jeremiah Horton and held within his family for generations, this extraordinary residence stands as a masterwork of early American stone architecture, thoughtfully preserved and seamlessly elevated with modern amenities.Set on 1.1

  Donna Brooks Compass Greater NY, LLC

  93 Horton Rd, Washingtonville, NY 10992
• 

  $175,000

  Sold Feb 26, 2026

  4 Lily Ct, Woodbury, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1993

  Last Sold Summary

  • $103/SF
  • 51 Days On Market

  Last Listing Agent Ivan Carvalho Exit Realty Connections

  4 Lily Ct, Woodbury, NY 10930
• 

  Est $651,581

  Not Listed For Sale

  55 Pine Hill Rd, Highland Mills, NY 10930

  • 5 Beds
  • 2.5 Baths
  • 2,020 Sq Ft
  • Built 1971

  55 Pine Hill Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Layla Rose Boyles Century 21 Realty Center
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  /24

  $519,000

  $21K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  25 Hollis St, Highland Mills, NY 10930

  Welcome to 25 Hollis Street, this beautiful 3-bedroom, 2 full and 1 half bathroom Colonial, perfectly situated in a highly desirable location that blends comfort, convenience, and lifestyle. This charming home offers spacious living areas, a functional layout, and timeless appeal—ideal for both everyday living and entertaining.Enjoy being just 5 minutes from the renowned Woodbury Common

  Theodore Wells OverSouth LLC

  25 Hollis St, Highland Mills, NY 10930
• 

  $450,000

  Sold Sep 24, 2025

  16 Robyn Dr, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 1959

  Last Sold Summary

  • 10% Below List Price
  • $335/SF
  • 66 Days On Market

  Current Estimated Value $464,276

  Last Listing Agent Bradford Lewis Keller Williams Realty

  16 Robyn Dr, Monroe, NY 10950
• 

  Est $393,129

  Not Listed For Sale

  612 State Route 32, Highland Mills, NY 10930

  • 3 Beds
  • 1,448 Sq Ft
  • Built 1875

  612 State Route 32, Highland Mills, NY 10930

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Jacob Katz MS Realty Group USA, Inc
• 

  

  /22

  $259,000

  • 2 Beds
  • 2 Baths
  • 964 Sq Ft

  2 Lexington Hill Unit 12, Harriman, NY 10926

  PRICED TO SELL - 2 Bed | 2 Bath | Top-End Unit | Monroe-Woodbury Schools | Stunning Views condo with some of the best views in the Lexington Hills community. Prime Location - Perfect for commuters and outdoor enthusiasts alike: 45 minutes to NYC by train (train station within walking distance), 55 minutes to NYC by car 10 min to Grocery/shop's New updates in the last 2 years 1) New Deck 2) New

  David White Owner Entry.com

  2 Lexington Hill Unit 12, Harriman, NY 10926
• 

  $880,000

  Sold Dec 03, 2025

  8 Tanyas Ct, Monroe, NY 10950

  • 4 Beds
  • 3.5 Baths
  • 3,614 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $243/SF
  • 59 Days On Market

  Current Estimated Value $896,917

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates

  8 Tanyas Ct, Monroe, NY 10950
• 

  Est $588,470

  Not Listed For Sale

  72 Pine Hill Rd, Highland Mills, NY 10930

  • 4 Beds
  • 2 Baths
  • 1,914 Sq Ft
  • Built 1968

  72 Pine Hill Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 80 Days On Market

  Last Listing Agent Steve Moreau Tactical Realty LLC
• 

  

  /19

  $239,000

  Pending

  • 2 Beds
  • 2 Baths
  • 968 Sq Ft

  27 Lexington Hill Unit 10, Harriman, NY 10926

  Enjoy peaceful, low-maintenance living in this bright and inviting 2-bedroom, 2-bath middle end-unit condo perfectly positioned in one of the area’s most convenient and scenic communities. A quaint porch offering a quiet spot to relax and enjoy the surroundings. The interior features a comfortable layout with updated appliances, plus an updated furnace and hot water heater for added efficiency

  BRIDGET CAPAWANA Exit Realty Connections

  27 Lexington Hill Unit 10, Harriman, NY 10926
• 

  $525,000

  Sold Dec 10, 2025

  12 Case Ct, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $282/SF
  • 62 Days On Market

  Current Estimated Value $538,986

  Last Listing Agent Donna Gray Redfin Real Estate

  12 Case Ct, Monroe, NY 10950
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  Not Listed For Sale

  15 Overlook Dr, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 2,144 Sq Ft
  • Built 1968

  15 Overlook Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Desiree Beecham River Realty Services, Inc.
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  /41

  $499,900

  • 2 Beds
  • 2.5 Baths
  • 1,777 Sq Ft

  20 Peter Turner Rd, Monroe, NY 10950

  The home you have been waiting for! A perfect offering in the highly sought after Hidden Creek community, this spectacular, sun-filled Harriman Model END unit—clean as a whistle—is the epitome of upscale townhouse living. Impeccably maintained and beautifully appointed from top to bottom, this move-in-ready residence is perfectly positioned to capture tranquil views of mature trees, while

  Lisa DaRos Houlihan Lawrence Inc.

  20 Peter Turner Rd, Monroe, NY 10950
• 

  $850,000

  Sold Jul 31, 2026

  5 Tappan Dr, Monroe, NY 10950

  • 5 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1959

  Last Sold Summary

  • 2% Below List Price
  • $425/SF
  • 185 Days On Market

  Current Estimated Value $787,760

  Last Listing Agent Shalom Landau eRealty Advisors, Inc

  5 Tappan Dr, Monroe, NY 10950
• 

  Est $543,266

  Not Listed For Sale

  76 Skyline Dr, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft
  • Built 1967

  76 Skyline Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Joseph Paoli Howard Hanna Rand Realty
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  /3

  $1,950,000

  • 5 Beds
  • 4 Baths

  348 Route 32, Other Areas, NY OTHER

  2 Acres Frontage Property Available! Calling all builders, investors, and primary users. This sale is comprised of approximately 2 acres in Woodbury, New York. Four-family property, with approved variance for commercial usage for street-adjacent section of parcels allows for future mixed-use development. Property can be delivered vacant or with tenants in place per purchaser's preference. Located

  Edmond Yoo Coldwell Banker, Fort Lee

  

  348 Route 32, Other Areas, NY OTHER
• 

  $815,000

  Sold Feb 17, 2026

  5 Lizensk Blvd, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $340/SF
  • 70 Days On Market

  Last Listing Agent Moshe Kaufman MK Realty Inc

  5 Lizensk Blvd, Monroe, NY 10950
• 

  Est $424,729

  Not Listed For Sale

  11 Ryan Place, Highland Mills, NY 10930

  • 5 Beds
  • 1.5 Baths
  • 1,204 Sq Ft
  • Built 1968

  11 Ryan Place, Highland Mills, NY 10930

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Avi Samet Avion
• 

  

  /8

  $1,200,000

  • 4 Beds
  • 2.5 Baths
  • 2,397 Sq Ft

  12 Arlington Dr, Monroe, NY 10950

  This is your opportunity to own a diamond that's needs a little polish. This large 4 bedroom 2.5 bath ranch is surrounded by brand new upscale homes and is in a convenient location. There are hardwood floors in every room. The HVAC (heat and A/C) along with the hot water heater has been recently replaced. The basement offers nearly 2300 sf of space for that can be finished in the future for

  Theresa Budich Howard Hanna Rand Realty

  12 Arlington Dr, Monroe, NY 10950
• 

  $585,000

  Sold Apr 29, 2026

  7 Ford Ct, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2004

  Last Sold Summary

  • 4% Below List Price
  • $282/SF
  • 30 Days On Market

  Current Estimated Value $588,141

  Last Listing Agent Amanda Rivera Sepulveda Keller Williams Realty

  7 Ford Ct, Monroe, NY 10950
• 

  Est $530,974

  Not Listed For Sale

  35 Skyline Dr, Highland Mills, NY 10930

  • 4 Beds
  • 1.5 Baths
  • 1,734 Sq Ft
  • Built 1976

  35 Skyline Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 54 Days On Market

  Last Listing Agent Maria Morales de Osorio Century 21 Elite Realty
• 

  

  /31

  $415,000

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  22 Valley Ave, Central Valley, NY 10917

  Welcome home to this charming 3-bedroom, 2-bath home nestled on a spacious lot with mature trees and a welcoming front porch. This well-maintained home offers a bright and inviting layout, featuring comfortable living spaces, generously sized bedrooms, and two full bathrooms. Enjoy relaxing mornings on the covered porch or entertaining in the private backyard. The dual driveways provide ample

  Jennifer Gillett Howard Hanna Rand Realty

  22 Valley Ave, Central Valley, NY 10917
• 

  $575,000

  Sold Dec 09, 2025

  27 Dorothy Dr, Monroe, NY 10950

  • 4 Beds
  • 1.5 Baths
  • 1,752 Sq Ft
  • Built 1965

  Last Sold Summary

  • 3% Below List Price
  • $328/SF
  • 63 Days On Market

  Current Estimated Value $580,260

  Last Listing Agent Shimon Weber Flag Realty Group

  27 Dorothy Dr, Monroe, NY 10950
• 

  Est $689,566

  Not Listed For Sale

  17 Sunny Ln, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,277 Sq Ft
  • Built 1961

  17 Sunny Ln, Highland Mills, NY 10930

  Last Sold Summary

  • 178 Days On Market

  Last Listing Agent Frank Tangredi Frank Tangredi Realty Company
• 

  

  /50

  $675,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,680 Sq Ft

  7 Paisley Ct, Highland Mills, NY 10930

  Welcome to the Prestigious Brigadoon Community in Highland Mills. Discover the perfect blend of style, space, and serenity in this contemporary gem, ideally situated at the end of a quiet cul-de-sac in the highly sought-after Brigadoon community. Located within the Monroe-Woodbury School District, this bright and beautiful home offers comfort and breathtaking mountain views throughout. The main

  Rosalie Cook Weichert Realtors

  7 Paisley Ct, Highland Mills, NY 10930
• 

  $750,000

  Sold Nov 21, 2025

  20 Calico Ln, Highland Mills, NY 10930

  • 4 Beds
  • 3 Baths
  • 2,660 Sq Ft
  • Built 2025

  Last Sold Summary

  • $282/SF
  • 19 Days On Market

  Current Estimated Value $801,962

  Last Listing Agent Donna Brunell RE/MAX Benchmark Realty Group

  20 Calico Ln, Highland Mills, NY 10930
• 

  Est $565,878

  Not Listed For Sale

  18 Lexington Ave, Highland Mills, NY 10930

  • 4 Beds
  • 1.5 Baths
  • 1,732 Sq Ft
  • Built 1966

  18 Lexington Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Jacob Fried Keller Williams Realty
• 

  

  /12

  $899,000

  • 4 Beds
  • 1.5 Baths
  • 1,596 Sq Ft

  251 Prospect Rd, Monroe, NY 10950

  Beautifully maintained home offering a bright, welcoming atmosphere and a thoughtfully designed layout. Spacious living areas and generously sized bedrooms provide comfort and flexibility for everyday living. The attractive front yard creates wonderful curb appeal, while the expansive backyard offers plenty of space for entertaining, recreation, and outdoor enjoyment. Combining charm,

  Lazar Schvimmer Mount Realty

  251 Prospect Rd, Monroe, NY 10950
• 

  $630,000

  Sold Aug 28, 2025

  14 Smith Clove Rd, Central Valley, NY 10917

  • 4 Beds
  • 2.5 Baths
  • 2,994 Sq Ft
  • Built 1890

  Last Sold Summary

  • 16% Below List Price
  • $210/SF
  • 49 Days On Market

  Current Estimated Value $655,211

  Last Listing Agent Patricia Spagna Century 21 Realty Center

  14 Smith Clove Rd, Central Valley, NY 10917
• 

  Est $711,094

  Not Listed For Sale

  73 Washington Dr, Highland Mills, NY 10930

  • 5 Beds
  • 2.5 Baths
  • 2,750 Sq Ft
  • Built 1966

  73 Washington Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 93 Days On Market

  Last Listing Agent Brian Bunsen Houlihan Lawrence Inc.
• 

  

  /4

  $589,000

  $61K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,698 Sq Ft

  3 Lizensk Blvd Unit 414, Monroe, NY 10950

  Rare opportunity in the heart of Kiryas Joel! This spacious top-floor corner unit offers approx. 1,698 sq ft, windows on two sides, high ceilings, a nice porch with beautiful views, and a walk-in attic for extra storage. Recently refreshed with fresh paint and scraped floors, giving it a clean, move-in-ready feel. The layout also offers flexibility with a possible setup for two smaller 2-bedroom

  Joel Brach Keller Williams Realty

  3 Lizensk Blvd Unit 414, Monroe, NY 10950
• 

  $693,000

  Sold Feb 23, 2026

  12 Edgewood Dr, Harriman, NY 10926

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Above List Price
  • $322/SF
  • 109 Days On Market

  Last Listing Agent Nathen Singer MK Realty Inc

  12 Edgewood Dr, Harriman, NY 10926
• 

  Est $611,634

  Not Listed For Sale

  88 Washington Dr, Highland Mills, NY 10930

  • 4 Beds
  • 1.5 Baths
  • 1,920 Sq Ft
  • Built 1968

  88 Washington Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /31

  $579,000

  • 3 Beds
  • 2.5 Baths
  • 1,761 Sq Ft

  13 Gillian Ct, Monroe, NY 10950

  Beautifully maintained and thoughtfully designed, thiswarm and inviting home is nestled within a sought-aftergated community on a quiet, private cul-de-sac. From themoment you step inside, you’ll feel the light, and positiveenergy that fills this inviting home. Sunlight pours throughthe windows, creating a bright and airy atmosphere thatfeels both uplifting and

  Chedva Dahan Q Home Sales

  13 Gillian Ct, Monroe, NY 10950

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