Highland Mills, NY Homes

• 

  $445,000

  Sold Oct 07, 2025

  271 and 231 Smith Clove Rd, Woodbury, NY 10930

  • Land
  • 25.6 Acres
  • $17,383 per Acre

  Last Sold Summary

  • 1% Below List Price
  • 331 Days On Market

  Last Listing Agent Karin Poggio HomeSmart Homes & Estates

  271 and 231 Smith Clove Rd, Woodbury, NY 10930
• 

  Est $345,220

  Not Listed For Sale

  1006 Cypress Ct, Highland Mills, NY 10930

  • 2 Beds
  • 1.5 Baths
  • 1,084 Sq Ft
  • Built 1990

  1006 Cypress Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 40 Days On Market

  Last Listing Agent Aneudy Rosa Keller Williams Realty
• 

  

  

  /50

  $949,000

  $41K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,570 Sq Ft

  10 Greenwich Ave, Central Valley, NY 10917

  A slice of Provence in the Hudson Valley. Locally revered as "The Castle on the Hill," Le Chateau des Verts offers a rare combination: the grand soul of a French estate with the easy, accessible flow of a ranch-style home. Sitting on over an acre of lush, mature grounds just 30 miles from Manhattan, it’s the ultimate escape for anyone looking to trade city noise for country quiet—without

  Micaela Stanaland Howard Hanna Rand Realty

  10 Greenwich Ave, Central Valley, NY 10917
• 

  $413,000

  Sold Apr 23, 2026

  23 Crotty Ct, Monroe, NY 10950

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft
  • Built 1955

  Last Sold Summary

  • 13% Below List Price
  • $430/SF
  • 72 Days On Market

  Current Estimated Value $422,786

  Last Listing Agent Stephen Ramundo Keller Williams Valley Realty

  23 Crotty Ct, Monroe, NY 10950
• 

  Est $328,432

  Not Listed For Sale

  806 Cypress Ct, Highland Mills, NY 10930

  • 2 Beds
  • 2 Baths
  • 998 Sq Ft
  • Built 1990

  806 Cypress Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Edward Scully ARC Realty 1 in Sales
• 

  

  /47

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  11 Country Hollow, Highland Mills, NY 10930

  Beautifully maintained and thoughtfully updated, this exceptional home is set on professionally landscaped grounds with outstanding curb appeal and a resort-style backyard designed for both relaxation and entertaining. The inviting interior features a grand entry foyer, a stunning chef's kitchen with custom cabinetry, granite countertops, and stainless steel appliances, along with spacious living

  Moche Halpern Blooming Realty

  11 Country Hollow, Highland Mills, NY 10930
• 

  $151,000

  Sold Sep 11, 2025

  167/171 Route 17s, Hillburn, NY 10953

  • Land
  • 13,939 Sq Ft
  • $471,875 per Acre

  Last Sold Summary

  • 4% Above List Price
  • 35 Days On Market

  Last Listing Agent Kevin L. Brentnall Howard Hanna Rand Realty

  167/171 Route 17s, Hillburn, NY 10953
• 

  Est $327,807

  Not Listed For Sale

  405 Ruby Ct, Highland Mills, NY 10930

  • 2 Beds
  • 2 Baths
  • 1,084 Sq Ft
  • Built 1990

  405 Ruby Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Nathalie Sessoms Howard Hanna Rand Realty
• 

  

  /32

  $289,000

  $10K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  13 Redwood Dr, Highland Mills, NY 10930

  Welcome home to this beautifully updated 2-bedroom end-unit townhouse offering the perfect blend of comfort, style, privacy, and convenience. This move-in ready home presents a rare opportunity to own a residence that has been lovingly maintained and thoughtfully updated throughout the years. Featuring gorgeous new flooring, a stunning new kitchen with modern finishes, beautifully renovated

  Jackie Siracuse Absolute Real Estate of NY Inc

  13 Redwood Dr, Highland Mills, NY 10930
• 

  $889,000

  Sold Feb 10, 2026

  20 Winding Ln, Central Valley, NY 10917

  • 5 Beds
  • 4.5 Baths
  • 3,608 Sq Ft
  • Built 2019

  Last Sold Summary

  • 10% Below List Price
  • $246/SF
  • 55 Days On Market

  Current Estimated Value $913,864

  Last Listing Agent Tristen Sierra Coldwell Banker Realty

  20 Winding Ln, Central Valley, NY 10917
• 

  Est $329,797

  Not Listed For Sale

  1903 Rosewood Ct, Highland Mills, NY 10930

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft
  • Built 1990

  1903 Rosewood Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Annmarie Kovacs Howard Hanna Rand Realty
• 

  

  /27

  $255,000

  Pending

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  27 Lexington Hill Unit 8, Harriman, NY 10926

  Welcome to this beautifully maintained first-floor end-unit condominium in the highly desirable Lexington Hills community. Offering the ease and convenience of one-level living, this bright and spacious home welcomes you with an inviting foyer that leads to an open-concept living room featuring a cozy fireplace and sliding glass doors opening to a patio—perfect for relaxing or enjoying the

  Rose Roper Howard Hanna Rand Realty

  27 Lexington Hill Unit 8, Harriman, NY 10926
• 

  $655,000

  Sold Jan 13, 2026

  11 Whitman Place, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,278 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 83 Days On Market

  Current Estimated Value $685,247

  Last Listing Agent David Kraus MK Realty Inc

  11 Whitman Place, Monroe, NY 10950
• 

  Est $640,942

  Not Listed For Sale

  6 Liberty Dr, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 1998

  6 Liberty Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 26 Days On Market

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /45

  $11,000,000

  $3M PRICE DROP

  • 16 Beds
  • 16 Baths
  • 15,252 Sq Ft

  14 Castleton Dr, Highland Mills, NY 10930

  R1A zoned, R3A zoned, agriculture zone approved, infinity pool, tennis and basketball court, gazebo and private lake set across gated 39.1 acresMAIN HOUSE - 10 bedrooms, 6 full baths, 3 half baths, 10 fireplaces, Kitchen has Miele Steam unit, Viking warming drawer, Viking microwave, 3 Viking ovens, including 6-burner and grill, 2 dishwashers, walk-in refrigerator, custom-designed and

  Laura Denberg Corcoran Baer & McIntosh

  14 Castleton Dr, Highland Mills, NY 10930
• 

  $446,000

  Sold Mar 05, 2026

  27 Forshee St, Monroe, NY 10950

  • 2 Beds
  • 2 Baths
  • 1,384 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Above List Price
  • $322/SF
  • 84 Days On Market

  Current Estimated Value $451,004

  Last Listing Agent Susan Giordano Hudson Premium Realty

  27 Forshee St, Monroe, NY 10950
• 

  Est $643,912

  Not Listed For Sale

  2 Liberty Dr, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 1997

  2 Liberty Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Catherine Eichner Eichner Realty Group Inc.
• 

  

  /23

  $599,000

  $51K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,402 Sq Ft

  4 Mack Place, Monroe, NY 10950

  Beautifully maintained and thoughtfully updated Colonial set in a prime location close to shopping, restaurants, parks, and major commuter routes. This spacious home offers bright sun-filled living areas, gleaming hardwood floors, and an inviting open layout perfect for everyday living and entertaining.The expansive kitchen features abundant cabinetry, generous counter space, and a seamless

  Joseph Rosenfeld Flag Realty Group

  4 Mack Place, Monroe, NY 10950
• 

  $350,000

  Sold Jul 28, 2026

  11 Boulder Dr, New Windsor, NY 12553

  • 2 Beds
  • 1.5 Baths
  • 1,487 Sq Ft
  • Built 1955

  Last Sold Summary

  • $235/SF
  • 62 Days On Market

  Last Listing Agent Hershel Mittelman The Middleman Team

  11 Boulder Dr, New Windsor, NY 12553
• 

  Est $715,251

  Not Listed For Sale

  40 Liberty Dr, Highland Mills, NY 10930

  • 4 Beds
  • 3.5 Baths
  • 2,682 Sq Ft
  • Built 1995

  40 Liberty Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 94 Days On Market

  Last Listing Agent Tamara LaBarbera Howard Hanna Rand Realty
• 

  

  /30

  $519,000

  $6K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,688 Sq Ft

  8 Roberts Dr, Monroe, NY 10950

  Welcome to your dream home nestled in a peaceful location, offering a park-like setting that provides the perfect backdrop for your growing family. This charming residence is set back off a quiet country road, ensuring tranquility and privacy for you and your loved ones. As you approach the property, you'll notice its idyllic, elevated placement, which adds to the natural aesthetics of the home.

  Moses Schreiber MS Realty Group USA, Inc

  8 Roberts Dr, Monroe, NY 10950
• 

  $270,000

  Sold Sep 16, 2025

  110 Mineral Springs Rd, Highland Mills, NY 10930

  • 3 Beds
  • 1 Bath
  • 1,164 Sq Ft
  • Built 1932

  Last Sold Summary

  • 10% Below List Price
  • $232/SF
  • 57 Days On Market

  Current Estimated Value $276,611

  Last Listing Agent Kelly Beary Keller Williams Realty

  110 Mineral Springs Rd, Highland Mills, NY 10930
• 

  Est $594,801

  Not Listed For Sale

  42 Liberty Dr, Highland Mills, NY 10930

  • 3 Beds
  • 2.5 Baths
  • 1,948 Sq Ft
  • Built 1995

  42 Liberty Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent William Bergin RE/MAX Benchmark Realty Group
• 

  

  /25

  $1,499,999

  • 3 Beds
  • 2 Baths
  • 3,450 Sq Ft

  283 Prospect Rd, Monroe, NY 10950

  An extraordinary property offering the perfect balance of privacy, comfort, and natural beauty. While the photos showcase its appeal, the true scale and atmosphere can only be experienced in person. Don't miss the opportunity to tour this exceptional home and see firsthand what makes it so special.

  Lazar Schvimmer Mount Realty

  283 Prospect Rd, Monroe, NY 10950
• 

  

  /34

  $475,000

  Sold Nov 25, 2025

  20 Amy Rd, Washingtonville, NY 10992

  • 4 Beds
  • 2 Baths
  • 1,662 Sq Ft
  • Built 1981

  Last Sold Summary

  • 14% Below List Price
  • $286/SF
  • 39 Days On Market

  Current Estimated Value $503,930

  Last Listing Agent Scott Alvarez Coldwell Banker Prime Properties

  20 Amy Rd, Washingtonville, NY 10992
• 

  Est $569,806

  Not Listed For Sale

  12 Lexington Ave, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1993

  12 Lexington Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Anita S. Cristiano HomeSmart Homes & Estates
• 

  

  /48

  $459,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  39 Overlook Rd, Monroe, NY 10950

  Welcome to Sky View Hills 39 Overlook Rd, Monroe, NY. Nestled on a spacious lot, this classic Cape Cod offers 3 bedrooms and 2 full baths in one of Orange County's most convenient and desirable locations. With timeless curb appeal and a versatile floor plan, this home is ready for its next chapter. The Cape Cod layout delivers comfortable main-level living with generous natural light throughout.

  Meralda Moehrle Keller Williams Hudson Valley

  39 Overlook Rd, Monroe, NY 10950
• 

  $485,000

  Sold Sep 04, 2025

  10 Cliffside Ct, Highland Mills, NY 10930

  • 3 Beds
  • 2.5 Baths
  • 1,569 Sq Ft
  • Built 2000

  Last Sold Summary

  • 4% Above List Price
  • $309/SF
  • 18 Days On Market

  Current Estimated Value $486,191

  Last Listing Agent Courtney HILBURG Realty Guild LLC

  10 Cliffside Ct, Highland Mills, NY 10930
• 

  Est $639,790

  Not Listed For Sale

  8 Lexington Ave, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,095 Sq Ft
  • Built 1993

  8 Lexington Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Steve Moreau Tactical Realty LLC
• 

  

  /33

  $575,000

  $50K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,988 Sq Ft

  333 Oakland Ave, Monroe, NY 10950

  A beautiful and spacious Cape Cod–style home set on a hill overlooking the Village of Monroe. Ideally located for commuting, this home offers close proximity to the ShortLine bus to NYC’s Port Authority Terminal, as well as just 3.7 miles to the train station-blending convenience with a peaceful setting. Enjoy nearby ponds, local dining, or time outdoors on the porch. Bright, airy, and well

  Eileen Hughes Howard Hanna Rand Realty

  333 Oakland Ave, Monroe, NY 10950
• 

  $630,000

  Sold Apr 28, 2026

  31 Newbury St, Monroe, NY 10950

  • 4 Beds
  • 3 Baths
  • 2,433 Sq Ft
  • Built 1984

  Last Sold Summary

  • 1% Below List Price
  • $259/SF
  • 25 Days On Market

  Current Estimated Value $640,691

  Last Listing Agent Joel Winkler Preferred Properties Real Esta

  31 Newbury St, Monroe, NY 10950
• 

  Est $687,042

  Not Listed For Sale

  2 Lexington Ave, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 2,439 Sq Ft
  • Built 1992

  2 Lexington Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 30 Days On Market

  Last Listing Agent Gzim Hakanjin Coldwell Banker Realty
• 

  

  /33

  $549,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 2 Baths
  • 1,580 Sq Ft

  12 Sunset Heights, Monroe, NY 10950

  CEDAR & STONE CRAFTSMAN COLONIAL — MUNICIPAL WATER, SEWER AND NATURAL GAS.TIMELESS CHARACTER WITH MODERN UPDATESThis beautifully maintained 4-bedroom, 2-bath Craftsman-style Colonial blends historic charm with thoughtful modern enhancements. Rich in character, the home showcases ORIGINAL MOLDINGS, architectural details, and HARDWOOD FLOORS THROUGHOUT, complemented by 9-FOOT CEILINGS on

  Mary Ann Mitchell eXp Realty

  12 Sunset Heights, Monroe, NY 10950
• 

  $1,350,000

  Sold Apr 30, 2026

  18 Pullman Route, Monroe, NY 10950

  • 6 Beds
  • 5.5 Baths
  • 4,171 Sq Ft
  • Built 2025

  Last Sold Summary

  • $324/SF
  • 138 Days On Market

  Current Estimated Value $1,339,000

  Last Listing Agent Joel Jeremias eRealty Advisors, Inc

  18 Pullman Route, Monroe, NY 10950
• 

  Est $461,316

  Not Listed For Sale

  23 Ridge Rd, Highland Mills, NY 10930

  • 3 Beds
  • 1 Bath
  • 1,332 Sq Ft
  • Built 1984

  23 Ridge Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Brian Smith River Realty Services, Inc.
• 

  

  /49

  $549,900

  • 3 Beds
  • 2 Baths
  • 1,254 Sq Ft

  21 Midland Ave, Central Valley, NY 10917

  Picturesque One-Level Living in Central ValleyConveniently located on a quiet street in the charming hamlet of Central Valley, this brick-faced ranch is the epitome of turn-key perfection. From the flawlessly manicured grounds to the immaculate interior, it is clear that every detail of this home has been meticulously maintained.The main level boasts gleaming hardwood floors, bright and

  Theresa Budich Howard Hanna Rand Realty

  21 Midland Ave, Central Valley, NY 10917
• 

  $929,000

  Sold Jun 03, 2026

  4 Mountain Brook Rd, Cornwall, NY 12518

  • 4 Beds
  • 2.5 Baths
  • 2,436 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $381/SF
  • 22 Days On Market

  Current Estimated Value $904,771

  Last Listing Agent Alicia Goldman Christie's Int. Real Estate

  4 Mountain Brook Rd, Cornwall, NY 12518
• 

  Est $781,988

  Not Listed For Sale

  107 Jefferson St, Highland Mills, NY 10930

  • 5 Beds
  • 3 Baths
  • 2,958 Sq Ft
  • Built 2002

  107 Jefferson St, Highland Mills, NY 10930

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent David Katina ESTMAX REALTY
• 

  

  /40

  $849,000

  • 6 Beds
  • 4.5 Baths
  • 3,857 Sq Ft

  155 Roselawn Rd, Highland Mills, NY 10930

  This high-impact, move-in-ready luxury home delivers instant appeal on 1.5 private, park-like acres. Designed to impress, it features vaulted ceilings, rich Brazilian wood floors, a granite kitchen, and a fireplace that anchors the space with warmth and style.The flexible layout offers 2 bedrooms plus an office on the main level—perfect for guests or extended living—while upstairs includes a

  Jacob Katz MS Realty Group USA, Inc

  155 Roselawn Rd, Highland Mills, NY 10930
• 

  $400,000

  Sold Aug 03, 2026

  22 Plum Ct, Highland Mills, NY 10930

  • 3 Beds
  • 2.5 Baths
  • 1,363 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $293/SF
  • 36 Days On Market

  Current Estimated Value $414,794

  Last Listing Agent Maurice Bailey Neighborhood Assistance Corp

  22 Plum Ct, Highland Mills, NY 10930

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