Highland Mills, NY Homes

• 

  

  

  /24

  $450,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,388 Sq Ft

  515 High St, Monroe, NY 10950

  Charming three-bedroom, two-bath home in the desirable Monroe-Woodbury School District. This inviting residence offers ample living and dining rooms, a kitchen with warm wood cabinetry, and convenient access to a covered patio—perfect for relaxing or entertaining. The lower level features a den, additional storage space, plus a utility and laundry area. Outside, you’ll find generous front and

  Annie Hansen Howard Hanna Rand Realty

  515 High St, Monroe, NY 10950
• 

  $570,000

  Sold Aug 11, 2025

  10 Cregan Place, Monroe, NY 10950

  • 4 Beds
  • 2 Baths
  • 1,844 Sq Ft
  • Built 1972

  Last Sold Summary

  • 2% Above List Price
  • $309/SF
  • 20 Days On Market

  Current Estimated Value $585,687

  Last Listing Agent Jayne M. Prechtel Keller Williams Valley Realty

  10 Cregan Place, Monroe, NY 10950
• 

  Est $918,628

  Not Listed For Sale

  23 Country Hollow, Highland Mills, NY 10930

  • 4 Beds
  • 3 Baths
  • 3,964 Sq Ft
  • Built 2000

  23 Country Hollow, Highland Mills, NY 10930

  Last Sold Summary

  • 155 Days On Market

  Last Listing Agent Esther Schwimmer Rock Realty Group USA Inc
• 

  

  

  /49

  $599,000

  $20K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,834 Sq Ft

  29 Olympus Rd, Highland Mills, NY 10930

  I am pleased to share the details for this immaculate, move-in-ready home in the Cornwall School District. The bright, open-concept layout features a sun-drenched living room and a sunken formal dining room with vaulted ceilings, both offering deck access. The updated kitchen includes granite countertops, stainless appliances, and a center island. The main level provides two bedrooms and a full

  Maurice Duarte Howard Hanna Rand Realty

  29 Olympus Rd, Highland Mills, NY 10930
• 

  $530,000

  Sold Jul 08, 2026

  22 Thompson Dr, Washingtonville, NY 10992

  • 3 Beds
  • 1.5 Baths
  • 1,816 Sq Ft
  • Built 1967

  Last Sold Summary

  • 8% Above List Price
  • $292/SF
  • 31 Days On Market

  Current Estimated Value $523,121

  Last Listing Agent Matthew Warbet Keller Williams Hudson Valley

  22 Thompson Dr, Washingtonville, NY 10992
• 

  Est $501,744

  Not Listed For Sale

  30 Scaglione Ct, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,632 Sq Ft
  • Built 1985

  30 Scaglione Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 72 Days On Market

  Last Listing Agent Hilary Ryan Goldman Howard Hanna Rand Realty
• 

  

  /23

  $650,000

  $49K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft

  35 Peddler Hill Rd, Monroe, NY 10950

  "High-Value Property – Exceptional Location, Endless Potential" Discover an exceptional investment opportunity in a highly sought-after area! This charming home sits on over half an acre of prime real estate, making it perfect for investors, builders, or anyone looking to secure a valuable asset. With its spacious lot and desirable location, this property promises not only immediate returns but

  Joseph Rosenfeld Flag Realty Group

  35 Peddler Hill Rd, Monroe, NY 10950
• 

  $227,000

  Sold Nov 14, 2025

  40 Tanager Rd Unit 4002, Monroe, NY 10950

  • 2 Beds
  • 1.5 Baths
  • 1,025 Sq Ft
  • Built 1970

  Last Sold Summary

  • 5% Below List Price
  • $221/SF
  • 85 Days On Market

  Current Estimated Value $235,884

  Last Listing Agent Dvora E. Price eXp Realty

  40 Tanager Rd Unit 4002, Monroe, NY 10950
• 

  Est $796,902

  Not Listed For Sale

  10 College Dr, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,608 Sq Ft
  • Built 2005

  10 College Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 65 Days On Market

  Last Listing Agent Lazar Schvimmer Blooming Realty
• 

  

  /37

  $289,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,222 Sq Ft

  3 Echo Trail, Monroe, NY 10950

  Welcome to 3 Echo Trail! Nestled in a peaceful mountain setting, this lovingly maintained home offers the perfect blend of privacy and convenience. Located just minutes from Washingtonville and Monroe, you'll enjoy easy access to shopping, restaurants, schools, houses of worship, and commuter transportation to NYC. Owned and cared for by the same family for nearly 40 years, the home showcases

  Jacqueline Manzolillo-Blais Keller Williams Realty

  3 Echo Trail, Monroe, NY 10950
• 

  $875,000

  Sold Jul 21, 2026

  24 Union Transfer, Monroe, NY 10950

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2026

  Last Sold Summary

  • $468/SF
  • 152 Days On Market

  Current Estimated Value $912,583

  Last Listing Agent Dovid Hoffman MK Realty Inc

  24 Union Transfer, Monroe, NY 10950
• 

  Est $565,703

  Not Listed For Sale

  11 Columbia Cir, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 1995

  11 Columbia Cir, Highland Mills, NY 10930

  Last Sold Summary

  • 107 Days On Market

  Last Listing Agent Richard Froehlich RE/MAX Benchmark Realty Group
• 

  

  /10

  $430,000

  • 4 Beds
  • 2 Baths
  • 1,296 Sq Ft

  10 Maplewood Rd, Highland Mills, NY 10930

  Location, lifestyle, and space all come together in this charming 4-bedroom, 2 full bath Cape— conveniently located near major highways for easy commuting and just minutes from Woodbury Commons shopping, dining, and entertainment. Step inside to a bright and airy living room featuring a large bay window that fills the space with natural light. The spacious eat-in kitchen offers plenty of room for

  Maria Murdie Picture It Sold, LLC

  10 Maplewood Rd, Highland Mills, NY 10930
• 

  $299,000

  Sold Sep 24, 2025

  8 Brookside Dr W, Harriman, NY 10926

  • 3 Beds
  • 2.5 Baths
  • 1,588 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $188/SF
  • 16 Days On Market

  Current Estimated Value $357,625

  Last Listing Agent Craig Watters Compass Greater NY, LLC

  8 Brookside Dr W, Harriman, NY 10926
• 

  Est $600,910

  Not Listed For Sale

  4 Stanford Dr, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,932 Sq Ft
  • Built 1996

  4 Stanford Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent David Katina ESTMAX REALTY
• 

  

  /41

  $760,000

  • 4 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  20 Tanyas Ct, Monroe, NY 10950

  Set on a beautifully landscaped lot with mountain views, this refined Colonial delivers space, light, and a smart, functional layout. This 4-bedroom, 2.5-bath Colonial (built in 2012) offers 2,740 square feet of beautifully proportioned space, plus a basement with high ceilings currently enjoyed as a home gym. Inside, the home balances elegance and comfort: a classic foyer entry, a

  Lismarie Santiago Highline Real Estate Services

  20 Tanyas Ct, Monroe, NY 10950
• 

  $579,900

  Sold Dec 22, 2025

  22 Ford Ct, Monroe, NY 10950

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Below List Price
  • $297/SF
  • 92 Days On Market

  Current Estimated Value $596,474

  Last Listing Agent Amanda Rivera Sepulveda Keller Williams Realty

  22 Ford Ct, Monroe, NY 10950
• 

  Est $722,143

  Not Listed For Sale

  8 Cambridge Rd, Highland Mills, NY 10930

  • 5 Beds
  • 3.5 Baths
  • 2,840 Sq Ft
  • Built 1995

  8 Cambridge Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 64 Days On Market

  Last Listing Agent Theresa Budich Howard Hanna Rand Realty
• 

  

  /12

  $360,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft

  4 Revere Rd, Monroe, NY 10950

  Welcome to 4 Revere Road, Monroe, NY! This newly renovated, inviting property features 3 spacious bedrooms among a total of 5 well-appointed rooms, offering plenty of space for comfortable living. Enjoy abundant natural light streaming through large, bright windows that create a warm and welcoming atmosphere throughout the home. Step outside onto the deck, perfect for relaxing or entertaining

  Samuel Posen MK Realty Inc

  4 Revere Rd, Monroe, NY 10950
• 

  $999,000

  Sold Dec 29, 2025

  29 Virginia Ave, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,391 Sq Ft
  • Built 1973

  Last Sold Summary

  • $418/SF
  • 95 Days On Market

  Current Estimated Value $976,370

  Last Listing Agent Lazar Schvimmer Blooming Realty

  29 Virginia Ave, Monroe, NY 10950
• 

  Est $806,515

  Not Listed For Sale

  2 Dartmouth Rd, Highland Mills, NY 10930

  • 5 Beds
  • 3 Baths
  • 3,362 Sq Ft
  • Built 1996

  2 Dartmouth Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /50

  $849,000

  Open Sun 11:30AM - 1:30PM $25K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 3,510 Sq Ft

  208 Oakland Ave, Monroe, NY 10950

  208 Oakland, MonroeSpecifications: 4 Bedrooms | 4.5 Bathrooms | 2 Kitchens | 2-Car GarageKey Layout Features: Interior Residential Elevator(Basement to First Floor)l Lower-Level Accessory Apartment with Walk-OutWelcome to 208 Oakland, a beautifully maintained 2004 residence offering private living and exceptional layout flexibility. Spanning three finished levels, this property is

  Yakov Winkler Preferred Properties Real Esta

  208 Oakland Ave, Monroe, NY 10950
• 

  $375,000

  Sold Apr 07, 2026

  19 Grandview Trail, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1945

  Last Sold Summary

  • 1% Below List Price
  • $357/SF
  • 92 Days On Market

  Current Estimated Value $348,877

  Last Listing Agent Courtney Tablante Keller Williams Realty

  19 Grandview Trail, Monroe, NY 10950
• 

  Est $733,153

  Not Listed For Sale

  19 Dartmouth Rd, Highland Mills, NY 10930

  • 4 Beds
  • 3 Baths
  • 2,824 Sq Ft
  • Built 1997

  19 Dartmouth Rd, Highland Mills, NY 10930

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Nathen Singer MK Realty Inc
• 

  

  /15

  $355,000

  • 2 Beds
  • 2 Baths
  • 1,032 Sq Ft

  3 Barnett Dr Unit 3, Monroe, NY 10950

  Amazing opportunity to own in Barnett Hills! This beautifully renovated second-floor condominium offers two spacious bedrooms and two full bathrooms, combining modern updates with low-maintenance living. This unit features an updated kitchen with contemporary finishes along with two updated bathrooms designed for both style and comfort. The bright functional layout provides generous living space,

  Michelle Getty HVG Realty, Inc.

  3 Barnett Dr Unit 3, Monroe, NY 10950
• 

  $569,500

  Sold Nov 13, 2025

  4 Genny Dr, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,108 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $270/SF
  • 87 Days On Market

  Current Estimated Value $581,763

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  4 Genny Dr, Highland Mills, NY 10930
• 

  Est $338,239

  Not Listed For Sale

  2102 Rosewood Ct, Highland Mills, NY 10930

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

  2102 Rosewood Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 73 Days On Market

  Last Listing Agent Aneudy Rosa Keller Williams Realty
• 

  

  /50

  $585,000

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  116 Barr Ln, Monroe, NY 10950

  Welcome to Meadow Glen, Monroe's premier gated community, where luxury, comfort, and convenience come together in one exceptional home. This beautifully maintained and extensively upgraded largest-model end unit offers an abundance of natural light through 24 oversized windows, each enhanced with elegant Hunter Douglas Country Wood blinds, creating a bright and inviting atmosphere throughout.

  Richard Froehlich RE/MAX Benchmark Realty Group

  116 Barr Ln, Monroe, NY 10950
• 

  $335,000

  Sold May 04, 2026

  1408 Rosewood Ct, Highland Mills, NY 10930

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

  Last Sold Summary

  • 1% Below List Price
  • $309/SF
  • 19 Days On Market

  Current Estimated Value $334,996

  Last Listing Agent Patricia Tompkins Weichert Realtors

  1408 Rosewood Ct, Highland Mills, NY 10930
• 

  Est $348,593

  Not Listed For Sale

  2101 Rosewood Ct Unit 93, Highland Mills, NY 10930

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

  2101 Rosewood Ct Unit 93, Highland Mills, NY 10930

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Jennifer Molino Keller Williams Realty
• 

  

  /20

  $345,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,170 Sq Ft

  1 Windsor Rd, Monroe, NY 10950

  Great opportunity for both homeowners and investors! This well-maintained ranch offers comfortable one-level living with a spacious layout, bright interiors, and a large backyard deck ideal for entertaining. Situated on a private fenced property with mature trees, the home provides a peaceful setting while remaining close to shopping, schools, and major conveniences. Whether you’re looking for a

  Joseph Rosenfeld Flag Realty Group

  1 Windsor Rd, Monroe, NY 10950
• 

  $264,500

  Sold Dec 30, 2025

  5 Orchard Trail, Monroe, NY 10950

  • 2 Beds
  • 1 Bath
  • 963 Sq Ft
  • Built 1948

  Last Sold Summary

  • 2% Below List Price
  • $275/SF
  • 81 Days On Market

  Current Estimated Value $267,794

  Last Listing Agent Ewa Kusmierek eXp Realty

  5 Orchard Trail, Monroe, NY 10950
• 

  Est $329,928

  Not Listed For Sale

  1506 Rosewood Ct, Highland Mills, NY 10930

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

  1506 Rosewood Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /49

  $999,998

  • 5 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  190 Ridge Rd, Highland Mills, NY 10930

  Welcome to 190 Ridge Road in the heart of Highland Mills! Nestled on a beautiful 1-acre lot in the highly sought-after Monroe-Woodbury School District, this spacious 4-bedroom, 3.5-bath split-level home offers over 2,500 square feet of comfortable living space designed for both everyday living and entertaining. Step inside to discover an inviting open floor plan featuring cathedral and high

  Rosemarie Morello KW Hudson Valley United

  190 Ridge Rd, Highland Mills, NY 10930
• 

  $580,000

  Sold Mar 03, 2026

  19 Sunset Terrace, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,136 Sq Ft
  • Built 1969

  Last Sold Summary

  • 7% Below List Price
  • $272/SF
  • 80 Days On Market

  Current Estimated Value $588,654

  Last Listing Agent Angela Paul Century 21 Alliance Rlty Group

  19 Sunset Terrace, Highland Mills, NY 10930
• 

  Est $336,484

  Not Listed For Sale

  1404 Honey Locust Ct, Highland Mills, NY 10930

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

  1404 Honey Locust Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 34 Days On Market

  Last Listing Agent Richard Froehlich RE/MAX Benchmark Realty Group
• 

  

  /36

  $729,000

  • 4 Beds
  • 2.5 Baths
  • 3,424 Sq Ft

  23 Cunningham Dr, Monroe, NY 10950

  Discover this stunning 5-bedroom colonial home nestled in the highly desirable Highland Mills area, offering the perfect blend of classic charm and comfort. Spanning over 3,400 square feet of sun-filled living space, this meticulously maintained residence features elegant architectural details, spacious formal and informal entertaining areas, and a versatile finished basement with a private

  David Kraus MK Realty Inc

  23 Cunningham Dr, Monroe, NY 10950
• 

  $396,550

  Sold Mar 20, 2026

  20 Woodbine Dr, Highland Mills, NY 10930

  • 2 Beds
  • 1.5 Baths
  • 1,474 Sq Ft
  • Built 1993

  Last Sold Summary

  • 1% Below List Price
  • $269/SF
  • 141 Days On Market

  Current Estimated Value $396,562

  Last Listing Agent Soleenne Desravines-Lafontant Exit Realty Connections

  20 Woodbine Dr, Highland Mills, NY 10930
• 

  Est $336,539

  Not Listed For Sale

  1203 Honey Locust Ct, Highland Mills, NY 10930

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

  1203 Honey Locust Ct, Highland Mills, NY 10930

  Last Sold Summary

  • 90 Days On Market

  Last Listing Agent Sharon Forsythe David L Russell Realty
• 

  

  /3

  $59,900

  $13K PRICE DROP

  • Land
  • 38,001 Sq Ft
  • $68,661 per Acre

  73 Sylvan Trail, Monroe, NY 10950

  This property includes 3 separate parcels 28-4-2, 29-3-1 and 29-3-3-Lots combined with possible variance will offer a 1.1 acre building lot. This level lot is located in the Mountain Lodge Community. Both full time and summer residents reside in this community. Building is subject to engineering, building approvals and permits and utilities on the property. Buyer will be responsible. 2 acre

  Jo-Ann Merla Howard Hanna Rand Realty

  73 Sylvan Trail, Monroe, NY 10950

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