Highland Mills, NY Homes

• 

  

  

  /27

  $519,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  11 Oxford Depot, Chester, NY 10918

  Welcome to 11 Oxford Depot Rd, Chester, NY — a unique 3-bedroom, 2-bath home that perfectly blends charm, space, and modern updates. Featuring beautiful hardwood floors throughout, multiple living and entertaining areas, spacious bedrooms, updated bathrooms, and flexible bonus space ideal for a home office, playroom, or guest setup. The finished lower level adds even more versatility with

  Aneudy Rosa Keller Williams Realty

  11 Oxford Depot, Chester, NY 10918
• 

  $103,000 Sold Jun 20, 2025

  5 Lily Ct, Woodbury, NY 10930

  • 3 Beds
  • 2 Baths
  • 884 Sq Ft
  • Built 2013

  Last Sold Summary

  • 6% Below List Price
  • $117/SF
  • 21 Days On Market

  Last Listing Agent Ivan Carvalho Exit Realty Connections

  5 Lily Ct, Woodbury, NY 10930
• 

  Est $441,924 Not Listed For Sale

  5 Stone Gate Rd, Central Valley, NY 10917

  • 3 Beds
  • 1 Bath
  • 1,845 Sq Ft
  • Built 1910

  5 Stone Gate Rd, Central Valley, NY 10917

  Last Sold Summary

  • 21% Above List Price
  • $198/SF
  • 46 Days On Market

  • Last Sold Price $365,000
  • Jun 20, 2024

  Last Listing Agent Lauren Kelly Howard Hanna Rand Realty
• 

  

  /2

  $650,000

  • 4 Beds
  • 1.5 Baths
  • 1,668 Sq Ft

  24 Pearsall Dr, Monroe, NY 10950

  4 bedroom Bilevel! So lovingly maintained! Sun-filled living room! Formal dining room with hardwood flooring Eat-in-kitchen leading to new Trex Deck with vinyl railing to completely fenced backyard with patio for gatherings! Outstanding beautiful backyard with park-like setting! Master bedroom w/2 closets! Family room Wonderful Monroe Village location & "sidewalks" included! Centrally located for

  Isaac Friedrich MS Realty Group USA, Inc

  24 Pearsall Dr, Monroe, NY 10950
• 

  $77,000 Sold Jul 14, 2025

  33 Lakeside Dr, Woodbury, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1987

  Last Sold Summary

  • 14% Below List Price
  • $45/SF
  • 4 Days On Market

  Last Listing Agent Ivan Carvalho Exit Realty Connections

  33 Lakeside Dr, Woodbury, NY 10930
• 

  Est $540,733 Not Listed For Sale

  3 Burrow Dr, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 1,752 Sq Ft
  • Built 1990

  3 Burrow Dr, Highland Mills, NY 10930

  Last Sold Summary

  • 2% Below List Price
  • $314/SF
  • 17 Days On Market

  • Last Sold Price $550,000
  • Sep 26, 2024

  Last Listing Agent Karen Taphorn Howard Hanna Rand Realty
• 

  

  /39

  $259,900

  • 2 Beds
  • 2 Baths
  • 960 Sq Ft

  15 Lexington Hill Unit 11, Harriman, NY 10926

  Beautifully Maintained Top Floor Unit! Mint Condition! 2 Bedrooms! 2 Full Bathrooms! Kitchen with Granite Counter Tops! Master Bedroom Suite with Walk In Closet! Living Room with Cathedral Ceilings, Sky Lights and Fireplace! Updated Bathrooms! Hardwood Floors! Private Deck with Mountain Views! Perfect Commuter Location! Walk to NYC Bus! Close to. Major Highways, Trains & Shopping!

  Amanda Dnistrian ARC Realty 1 in Sales

  15 Lexington Hill Unit 11, Harriman, NY 10926
• 

  $315,000 Sold Mar 21, 2026

  1306 Rosewood Ct, Highland Mills, NY 10930

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

  Last Sold Summary

  • 4% Below List Price
  • $291/SF
  • 80 Days On Market

  Current Estimated Value $317,313

  Last Listing Agent Martin Remo RE/MAX Prime Properties

  1306 Rosewood Ct, Highland Mills, NY 10930
• 

  Est $554,898 Not Listed For Sale

  30 Cindy Ln, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,336 Sq Ft
  • Built 1967

  30 Cindy Ln, Highland Mills, NY 10930

  Last Sold Summary

  • 76% Above List Price
  • $135/SF
  • 36 Days On Market

  • Last Sold Price $315,000
  • Nov 08, 2023

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

  

  /5

  $380,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,788 Sq Ft

  261 Spring St, Monroe, NY 10950

  Property has structure but is currently not accessible, property was inherited but neglected over many years, we are working on providing access but yet to be determined, house would need to be emptied and is most likely a tear-down, utilities not operational, seller is open to all reasonable offers and is negotiable, place all offers for consideration. Property is zoned as SR-20 (Suburban

  Eric Vazquez Keller Williams Realty

  261 Spring St, Monroe, NY 10950
• 

  $221,000 Sold Aug 22, 2025

  2 Lexington Hill Unit 10, Harriman, NY 10926

  • 2 Beds
  • 2 Baths
  • 964 Sq Ft
  • Built 1985

  Last Sold Summary

  • 3% Below List Price
  • $229/SF
  • 35 Days On Market

  Current Estimated Value $234,087

  Last Listing Agent Donna Reese Keller Williams Hudson Valley

  2 Lexington Hill Unit 10, Harriman, NY 10926
• 

  Est $613,727 Not Listed For Sale

  14 Cindy Ln, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,486 Sq Ft
  • Built 1967

  14 Cindy Ln, Highland Mills, NY 10930

  Last Sold Summary

  • 1% Above List Price
  • $245/SF
  • 88 Days On Market

  • Last Sold Price $610,000
  • Nov 04, 2024

  Last Listing Agent Esther Schwimmer Rock Realty Group USA Inc
• 

  

  /38

  $749,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  32 Dallas Dr, Monroe, NY 10950

  Motivated Sellers!! Bring Your offers!! Beautifully 5-Bedroom Home In The Village Of South Blooming Grove Welcome to this beautifully 5-bedroom, 2.5-bath home with Many Upgrades, This 3 Story Home is offering 2,204 sq. ft. of comfortable living space on a 0.3-acre lot. Pride of ownership shows throughout, with numerous updates and modern features. The main floor features a bright kitchen, dining,

  Hershel Lowy Master Realty Group Inc.

  32 Dallas Dr, Monroe, NY 10950
• 

  $155,000 Sold Aug 29, 2025

  55 Orchard Trail, Monroe, NY 10950

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft
  • Built 1935

  Last Sold Summary

  • 3% Above List Price
  • $258/SF
  • 72 Days On Market

  Current Estimated Value $168,812

  Last Listing Agent Joel Ayala HomeSmart Homes & Estates

  55 Orchard Trail, Monroe, NY 10950
• 

  Est $799,196 Not Listed For Sale

  1 Cindy Ln, Highland Mills, NY 10930

  • 5 Beds
  • 4.5 Baths
  • 3,182 Sq Ft
  • Built 1967

  1 Cindy Ln, Highland Mills, NY 10930

  Last Sold Summary

  • 6% Above List Price
  • $236/SF
  • 37 Days On Market

  • Last Sold Price $751,000
  • Aug 16, 2024

  Last Listing Agent Rosalie Cook Weichert Realtors
• 

  

  /24

  $245,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,116 Sq Ft

  8 Pioneer Trail, Monroe, NY 10950

  Welcome to 8 Pioneer Trail — a fully gut-renovated mountain retreat in the peaceful Mountain Lodge Park community. Please follow these instructions to get the house. 1.Enter Glenwood Rd as the destination2.From Clove Rd, turn onto Glenwood Rd until the end3.At the parking lot, turn left onto Mountain Lodge Rd4.After one block (250ft), turn right onto Sylvan Trail5.After about

  Arya Rabinovits eRealty Advisors, Inc

  8 Pioneer Trail, Monroe, NY 10950
• 

  $715,000 Sold Dec 12, 2025

  2 Mockingbird Ln, Washingtonville, NY 10992

  • 6 Beds
  • 4 Baths
  • 2,384 Sq Ft
  • Built 1968

  Last Sold Summary

  • 5% Below List Price
  • $300/SF
  • 61 Days On Market

  Current Estimated Value $716,072

  Last Listing Agent Naomi Catania Picture It Sold, LLC

  2 Mockingbird Ln, Washingtonville, NY 10992
• 

  Est $557,731 Not Listed For Sale

  19 Cindy Ln, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 2,240 Sq Ft
  • Built 1967

  19 Cindy Ln, Highland Mills, NY 10930

  Last Sold Summary

  • 12% Above List Price
  • $223/SF
  • 94 Days On Market

  • Last Sold Price $500,000
  • Aug 24, 2023

  Last Listing Agent Virginia Corbett eXp Realty
• 

  

  /44

  $625,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  93 Dunderberg Rd, Central Valley, NY 10917

  One of Woodbury’s Finest Homes – Exceptional Location, Stunning Yard, and Move-In Ready!Welcome to one of the most desirable homes in Woodbury—where impeccable curb appeal, thoughtful updates, and an extraordinary outdoor retreat come together to create something truly special. From the moment you arrive, you’ll be captivated by the home’s inviting exterior, featuring a brand-new driveway,

  Karin Poggio HomeSmart Homes & Estates

  93 Dunderberg Rd, Central Valley, NY 10917
• 

  $412,000 Sold Apr 27, 2026

  9 Hillside Terrace, Monroe, NY 10950

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft
  • Built 1957

  Last Sold Summary

  • $477/SF
  • 7 Days On Market

  Current Estimated Value $406,219

  Last Listing Agent Lazar Schvimmer Blooming Realty

  9 Hillside Terrace, Monroe, NY 10950
• 

  Est $492,266 Not Listed For Sale

  10 Hollis St, Highland Mills, NY 10930

  • 3 Beds
  • 2.5 Baths
  • 1,840 Sq Ft
  • Built 1905

  10 Hollis St, Highland Mills, NY 10930

  Last Sold Summary

  • $266/SF
  • 121 Days On Market

  • Last Sold Price $490,000
  • Feb 18, 2025

  Last Listing Agent Mike Santoianni Tuxedo Park Aff Realty Ltd
• 

  

  /7

  $199,000

  • Land
  • 9,966 Sq Ft
  • $869,755 per Acre

  29 Westend Dr, Woodbury Town, NY 10930

  Build Your Dream Home! FULLY APPROVED PLAND-SHOVAL READY! plans can be amended for a smaller house if you want, Welcome to 29 Westend Dr This exceptional opportunity offers a rare chance to build your own stunning colonial-style home on a serene cul-de-sac, providing a tranquil retreat from the hustle and bustle of everyday life. With fully approved plans and shovel-ready conditions, you can

  Yakov Winkler Preferred Properties Real Esta

  29 Westend Dr, Woodbury Town, NY 10930
• 

  $670,000 Sold Dec 05, 2025

  55 Midland Ave, Central Valley, NY 10917

  • 4 Beds
  • 3 Baths
  • 2,959 Sq Ft
  • Built 1962

  Last Sold Summary

  • 1% Below List Price
  • $226/SF
  • 133 Days On Market

  Current Estimated Value $686,187

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

  55 Midland Ave, Central Valley, NY 10917
• 

  Est $453,908 Not Listed For Sale

  21 Elm St, Highland Mills, NY 10930

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft
  • Built 1920

  21 Elm St, Highland Mills, NY 10930

  Last Sold Summary

  • 8% Above List Price
  • $197/SF
  • 17 Days On Market

  • Last Sold Price $420,000
  • Aug 21, 2023

  Last Listing Agent Elizabeth Muniz Howard Hanna Rand Realty
• 

  

  /42

  $599,000

  • 4 Beds
  • 3 Baths
  • 2,048 Sq Ft

  300 Mountain Lodge Rd, Monroe, NY 10950

  Welcome to 300 Mountain Lodge Road — a beautifully updated and move-in-ready bilevel home offering the perfect blend of modern comfort and functional space. This 4-bedroom, 3-bathroom residence is set on a serene and scenic lot, providing peace and privacy while still being just minutes from all Monroe and Washingtonville has to offer. Step inside to discover a bright and spacious interior

  Zachary Leentjes Wansor Realty

  300 Mountain Lodge Rd, Monroe, NY 10950
• 

  $435,000 Sold Jun 24, 2025

  25 Woodward Terrace, Central Valley, NY 10917

  • 4 Beds
  • 1.5 Baths
  • 1,688 Sq Ft
  • Built 1952

  Last Sold Summary

  • 13% Above List Price
  • $258/SF
  • 17 Days On Market

  Current Estimated Value $451,059

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group

  25 Woodward Terrace, Central Valley, NY 10917
• 

  Est $582,629 Not Listed For Sale

  58 Sunset Terrace, Highland Mills, NY 10930

  • 4 Beds
  • 2.5 Baths
  • 1,928 Sq Ft
  • Built 1980

  58 Sunset Terrace, Highland Mills, NY 10930

  Last Sold Summary

  • 11% Above List Price
  • $272/SF
  • 64 Days On Market

  • Last Sold Price $525,000
  • May 16, 2023

  Last Listing Agent Kim Chiapperino RE/MAX Benchmark Realty Group
• 

  

  /42

  $499,000 Pending

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

  32 Peter Turner Rd, Monroe, NY 10950

  Rare Hidden Creek end-unit luxury! This sun-drenched 2-bedroom condo features 2 full and 2 half baths, an open-concept layout, and gleaming hardwood floors throughout. The stylish kitchen is a chef’s delight with stainless appliances, granite countertops, and a breakfast bar. Step through the sliders to your private back deck, perfect for alfresco dining. Upstairs, the spacious primary suite

  Beth Palma Keller Williams Realty

  32 Peter Turner Rd, Monroe, NY 10950
• 

  $675,000 Sold Jan 16, 2026

  158 Harriman Heights Rd, Monroe, NY 10950

  • 4 Beds
  • 2.5 Baths
  • 2,732 Sq Ft
  • Built 1935

  Last Sold Summary

  • 3% Below List Price
  • $247/SF
  • 30 Days On Market

  Current Estimated Value $681,881

  Last Listing Agent Ernie Acampora River Realty Services, Inc.

  158 Harriman Heights Rd, Monroe, NY 10950
• 

  Est $505,937 Not Listed For Sale

  27 Hickory St, Highland Mills, NY 10930

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft
  • Built 1965

  27 Hickory St, Highland Mills, NY 10930

  Last Sold Summary

  • 12% Above List Price
  • $281/SF
  • 23 Days On Market

  • Last Sold Price $449,900
  • Jul 31, 2023

  Last Listing Agent John Biasi Howard Hanna Rand Realty
• 

  

  /49

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 2,786 Sq Ft

  18 Reynolds Rd, Monroe, NY 10950

  Your dream home has finally hit the market and you don't have to wait for it to be built! Why pay for new construction when you can get so much more in this prime location in the village of Monroe. Rocking chair front porch welcomes you and leads you inside to find nearly 2800 square feet of living space and a bright neutral interior. Hardwood floors run throughout most of the main floor and an

  Laurel Lustgarten Howard Hanna Rand Realty

  18 Reynolds Rd, Monroe, NY 10950
• 

  $710,000 Sold Mar 11, 2026

  16 Prag Blvd Unit 201, Monroe, NY 10950

  • 3 Beds
  • 1.5 Baths
  • 1,800 Sq Ft
  • Built 2012

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 97 Days On Market

  Current Estimated Value $728,938

  Last Listing Agent Moses Zwiebel MS Realty Group USA, Inc

  16 Prag Blvd Unit 201, Monroe, NY 10950
• 

  Est $378,003 Not Listed For Sale

  14 Rock Ave, Highland Mills, NY 10930

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1926

  14 Rock Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 14% Above List Price
  • $369/SF
  • 23 Days On Market

  • Last Sold Price $332,500
  • Aug 01, 2023

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

  

  /9

  $199,000

  • Land
  • 8,568 Sq Ft
  • $1,011,693 per Acre

  27 Westend Dr, Woodbury Town, NY 10930

  Build Your Dream Home! FULLY APPROVED PLAND-SHOVAL READY! plans can be amended for a smaller house if you want, Welcome to 27 Westend Dr This exceptional opportunity offers a rare chance to build your own stunning colonial-style home on a serene cul-de-sac, providing a tranquil retreat from the hustle and bustle of everyday life. With fully approved plans and shovel-ready conditions, you can

  Yakov Winkler Preferred Properties Real Esta

  27 Westend Dr, Woodbury Town, NY 10930
• 

  $330,000 Sold Sep 12, 2025

  27 Revere Rd, Monroe, NY 10950

  • 3 Beds
  • 2 Baths
  • 1,048 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Above List Price
  • $315/SF
  • 39 Days On Market

  Current Estimated Value $345,108

  Last Listing Agent Priscilla Chang-Staley Howard Hanna Rand Realty

  27 Revere Rd, Monroe, NY 10950
• 

  Est $416,521 Not Listed For Sale

  11 Rock Ave, Highland Mills, NY 10930

  • 3 Beds
  • 1.5 Baths
  • 1,918 Sq Ft
  • Built 1900

  11 Rock Ave, Highland Mills, NY 10930

  Last Sold Summary

  • 15% Above List Price
  • $189/SF
  • 97 Days On Market

  • Last Sold Price $363,000
  • Aug 08, 2023

  Last Listing Agent Robert 'Bob' & Frances 'Fran' Murray Howard Hanna Rand Realty
• 

  

  /50

  $1,290,000

  • 4 Beds
  • 4.5 Baths
  • 5,142 Sq Ft

  221 Smith Clove Rd, Highland Mills, NY 10930

  Introducing one of Highland Mills’ most impressive estates—an architectural statement set on 6.5 private acres in the Monroe–Woodbury School District. Built by a seasoned general contractor for his own family, this 5,140+ sq ft residence pairs exceptional craftsmanship with the scale and sophistication of a true luxury home. A sun-filled two-story foyer welcomes you with a sweeping handcrafted

  Jamie Aisenstat Serhant LLC

  221 Smith Clove Rd, Highland Mills, NY 10930
• 

  $405,000 Sold Feb 11, 2026

  15 Freeland St, Monroe, NY 10950

  • 3 Beds
  • 1 Bath
  • 1,274 Sq Ft
  • Built 1956

  Last Sold Summary

  • 6% Below List Price
  • $318/SF
  • 71 Days On Market

  Current Estimated Value $410,710

  Last Listing Agent Joel Ayala HomeSmart Homes & Estates

  15 Freeland St, Monroe, NY 10950
• 

  Est $444,760 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

  • 3% Above List Price
  • $280/SF
  • 19 Days On Market

  • Last Sold Price $430,000
  • Aug 01, 2024

  Last Listing Agent Nathen Singer MK Realty Inc
• 

  

  /49

  $815,000

  • 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 Azure Realty Group NY LLC

  20 Tanyas Ct, Monroe, NY 10950

Showing Results 601 - 640, Page 16 of 18