Highland Mills, NY Homes for Sale

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  $850,000

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

  5 Tappan Dr, Monroe, NY 10950

  Don't miss out on this opportunity to own your lakefront dream home situated on a quiet, half acre, cul-de-sac in the village of South Blooming Grove.You will be minutes away from major highways, close to supermarkets and everything this neighborhood has to offer. Whether you're lookingto move in, build you own dream home or invest, this is the home for you!

  Shalom Landau eRealty Advisors, Inc

  5 Tappan Dr, Monroe, NY 10950
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  $999,000

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

  12 Damian Ct, Chester, NY 10918

  Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

  Elimelech Kremer MS Realty Group USA, Inc

  12 Damian Ct, Chester, NY 10918
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  $565,000

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

  20 Jones Dr, Highland Mills, NY 10930

  Welcome to Majestic 20 Jones Drive in Highland Mills NY. This Gorgeous home features a very Large Living Rm with Bay window, Formal Dining rm with crown molding, Gourmet Eat in Kitchen offering lots of built in cabinetry, counter space and appliances. New stove and Dishwasher. Newer Full bathroom. Spacious Primary Bedroom suite that includes a nice bathroom and lots of closet space. 2 additional

  John Biasi Howard Hanna Rand Realty

  20 Jones Dr, Highland Mills, NY 10930
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  $625,000

  • 4 Beds
  • 3 Baths
  • 2,270 Sq Ft

  46 Moulton Cir, Monroe, NY 10950

  Don’t miss out on this opportunity to own your dream home in the desired Monroe-Woodbury school district. Nesting on .26 acres, spanning an impressive 2,270 square feet, and locating only 5 minutes away from downtown Monroe, this home features a thoughtfully designed layout with 9 spacious rooms, making it a private sanctuary like no other. As you step inside, you’ll be greeted by a bright and an

  Louis Octobre Weichert Realtors

  46 Moulton Cir, Monroe, NY 10950
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  $869,000

  • 5 Beds
  • 2 Baths
  • 1,900 Sq Ft

  11 Merriewold Ln N, Monroe, NY 10950

  Discover this beautiful colonial in the sought-after Merriewold section of the Village of South Blooming Grove. With 5 bedrooms and 2 bathrooms, this home offers plenty of space for a growing family. The spacious interior features a kitchen breakfast bar, a formal dining room, and an inviting living area. The level, private lot offers plenty of room for outdoor activities. The backyard is

  Shalom Landau eRealty Advisors, Inc

  11 Merriewold Ln N, Monroe, NY 10950
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  $299,000

  • 2 Beds
  • 1 Bath
  • 1,078 Sq Ft

  215 Old Route 32, Highland Mills, NY 10930

  Calling all car enthusiasts, contractors, landscapers, excavators and dreamers — this is the kind of property that doesn’t come around often. Set on over 2 acres in the highly sought-after Cornwall school district, this property offers endless potential for someone with vision. Let’s talk about the showstopper — a massive pole barn that’s every hobbyist or business owner’s dream. Whether you need

  Tristen Sierra Coldwell Banker Realty

  215 Old Route 32, Highland Mills, NY 10930
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  $559,000

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

  3 Webster Ct, Monroe, NY 10950

  Enjoy this spacious 3-bedroom townhouse in gated community. well maintained complex- Great open floor plan that will be perfect for gatherings. Gas fireplace adds to the beauty of the living room. Sliding doors lead to a rear yard deck. New bathroom - Plenty of closet space- Unfinished basement with sliding door and windows. Can possibly be finished. Monroe-Woodbury Schools - Close to

  Kevin Abrams Hudson Heritage Realty

  3 Webster Ct, Monroe, NY 10950
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  $299,000

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft

  5 Beverly Trail, Monroe, NY 10950

  BACK ON THE MARKET — better than ever. Step into a home where the hard work is already done. After an extensive renovation, this 3-bedroom, 2-bath property feels fresh, bright, and inviting, featuring a brand-new kitchen, new floors, new foundation, new deck, fresh paint throughout, and new sheetrock. Sunlight fills the open dining area, flowing effortlessly from the updated kitchen perfect for

  Tulay Erdem Christie's Int. Real Estate

  5 Beverly Trail, Monroe, NY 10950
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  /38

  $749,000

  • 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
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  $259,000

  • 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
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  $769,000

  • 3 Beds
  • 2 Baths
  • 1,794 Sq Ft

  9 Merriewold Ln S, Monroe, NY 10950

  Welcome to 9 Merriewold Lane South – a charming 3-bedroom, 2-bathroom ranch in the heart of Monroe’s desirable South Blooming Grove community. Nestled on a tranquil tree-lined street, this well-maintained home greets you with one-level convenience and a warm, inviting atmosphere. Step inside to a bright living room filled with natural light, perfect for relaxing or entertaining. The adjoining

  Isaac Rottenberg Realty Blue Corp

  9 Merriewold Ln S, Monroe, NY 10950
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  $199,000

  • Land
  • 0.23 Acre
  • $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
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  $199,000

  • Land
  • 0.2 Acre
  • $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
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  $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
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  $999,999

  • 6 Beds
  • 3 Baths
  • 2,350 Sq Ft

  15 Duelk Ave, Monroe, NY 10950

  15 Duelk Ave, Monroe, NY — Enjoy a refreshing lifestyle with your own swimming pool at this charming single-family home. Offering 6 bedrooms and 3 bathrooms, this property features a finished basement, an attached garage, and a spacious yard perfect for gatherings and relaxation. Nestled in a quiet residential neighborhood and conveniently close to schools, shopping, and local amenities—this is a

  Chaim Reich eRealty Advisors, Inc

  15 Duelk Ave, Monroe, NY 10950
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  /23

  $499,900

  • 2 Beds
  • 1.5 Baths
  • 1,120 Sq Ft

  157 Stage Rd, Monroe, NY 10950

  Village living at 157 Stage Road delivers charm, walkability, and carefully preserved character paired with thoughtful, modern upgrades. Located in the heart of the Village of Monroe, this sidewalk neighborhood home features updated vinyl siding and has been meticulously and masterfully renovated while maintaining its warm historic appeal. Inside, beautiful pine floors, exposed brickwork, and

  Rosalie Cook Weichert Realtors

  157 Stage Rd, Monroe, NY 10950
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  $835,000

  • 5 Beds
  • 3.5 Baths
  • 3,022 Sq Ft

  4 Carlisle Ct, Highland Mills, NY 10930

  Distinguished 5 bedroom, 3.5 bath colonial located in the prestigious and coveted Brigadoon community! This stately colonial offers over 4,000 square feet of refined living space set on a sprawling .60 acre lot. With classic charm and modern comfort, this home is designed to impress! Step inside to a grand foyer that leads to beautifully appointed formal living and dining rooms, perfect for

  Patricia Tompkins Weichert Realtors

  4 Carlisle Ct, Highland Mills, NY 10930
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  $799,999 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 2,544 Sq Ft

  5 Bens Way, Chester, NY 10918

  On Market Monday 2/9/2026

  Anthony Rivas Keller Williams Hudson Valley

  5 Bens Way, Chester, NY 10918
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  $59,000

  • Land
  • 0.22 Acre
  • $272,015 per Acre

  11 Olympus Rd, Woodbury Town, NY 10930

  Wonderful vacant lot in a developed community with CORNWALL SCHOOLS. The wooded lot has outstanding mountain views and is similar in size to the other lots in the neighborhood. Builders can take advantage of nearby municipal water and sewer. Make an offer today.

  Dennis Clark Howard Hanna Rand Realty

  11 Olympus Rd, Woodbury Town, NY 10930
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  $25,000

  • Land
  • 0.24 Acre
  • $104,559 per Acre

  0 Emerald Trail, Blooming Grove, NY 10950

  Land for Sale in The Mountain Lodge Park Lots 20-308 through 20-320, Silver Falls Section. No Access. Do not walk on property.

  Maritza Sanchez HomeSmart Homes & Estates

  0 Emerald Trail, Blooming Grove, NY 10950
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  $300,000

  • Land
  • 3 Acres
  • $100,000 per Acre

  331 Mountain Lodge Rd, Blooming Grove, NY 10914

  Only 90 minutes from NYC. Reminiscent of the iconic swimming holes of the Catskills, let the sounds of nature soothe you from your private stream and 20-foot waterfall. Fully engineered for a 3 bedroom, 3 bath home, the leg work has already been done. Complete survey with topography, perk test, soil samples and well and septic engineering were done. The 3-acre lot spans across a cleared homesite,

  Lisa Mulcahy Ellis Sotheby's Intl Realty

  331 Mountain Lodge Rd, Blooming Grove, NY 10914
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  $489,000

  • Land
  • 0.46 Acre
  • $1,070,490 per Acre

  304 Round Lake Terrace, Monroe, NY 10950

  Discover the rare opportunity to own 105 ft of pristine lakefront property. Watch sunrise and sunset views each morning and evening. This is a one of a kind parcel on Round Lake. This natural setting offers direct shoreline access and a peaceful setting surrounded by nature to provide you with both privacy and breathtaking scenery year-round. Whether you are seeking your dream home, private

  Carol Scully Keller Williams Realty

  304 Round Lake Terrace, Monroe, NY 10950
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  $500,000

  • 3 Beds
  • 1,272 Sq Ft

  20 N Main St, Monroe, NY 10950

  Don’t miss this rare opportunity to own a two-family home in one of the area's most sought-after neighborhoods. Ideal for savvy investors or owner-occupants for home replacement, this property offers exceptional potential for strong future appreciation and long-term value. Whether you're looking to expand your portfolio or secure a smart investment in a thriving community, this versatile property

  Rivky Klagsbrun Catskills Home Services

  20 N Main St, Monroe, NY 10950
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  $699,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, Chester, NY 10918
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  $429,900

  • 3 Beds
  • 2.5 Baths
  • 1,575 Sq Ft

  3 Laurel Ct, Highland Mills, NY 10930

  TIMBER RIDGE!! BEAUTIFUL END UNIT! 3 Bedrooms! 2 1/2 Updated Bathrooms! Car Port with Storage Closet! Eat In Kitchen with Stainless Steel Appliances! Master Bedroom Suite! Large Living Room with Sliders to a New Oversized Privacy Deck! New Furnace! New Central Air! Updated Flooring! Recessive Lighting! Ceiling Fans! Full Finished Basement for Endless Possibilities! New Cedar Siding! Enjoy the

  Amanda Dnistrian ARC Realty 1 in Sales

  3 Laurel Ct, Highland Mills, NY 10930
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  $629,000

  • 5 Beds
  • 2 Baths
  • 2,368 Sq Ft

  52 Woodland Rd, Highland Mills, NY 10930

  Wow! This enlarged Highland Mills raised ranch boasts 5 bedrooms and two full baths situated on a corner lot next to designated Town green space. Its grassy front, back and side yards contain mature trees and perennial plants that create a serene, relaxing environment. Inside the home is a lovely living room with a newer Anderson bow window that lets in tons of afternoon light. There is original

  Derek Greene Greene Realty Group

  52 Woodland Rd, Highland Mills, NY 10930
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  $999,999

  • 4 Beds
  • 3 Baths
  • 2,764 Sq Ft

  Unlisted Address

  Are you looking for a 3+ ACRE getaway from the city that is 5 minutes to the Thruway, and 50 minutes from the GWB? Or, how about a professional home office, organic garden hobbyist, & perhaps extended. The approximate total finished sq ftge is 4800 not including the finished basement in the house. It is worthwhile to see this original 4 bedroom farmhouse that has been UPDATED with genuine

  Naomi Streicher Q Home Sales

  Unlisted Address
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  $485,500

  • 3 Beds
  • 2 Baths
  • 1,472 Sq Ft

  12 Mid Oaks Dr, Monroe, NY 10950

  Lovely and classic ranch perfectly perched up high with beautiful, peaceful views of the mountains. This home is bright and airy featuring three bedrooms, two full bathrooms, large formal dining room, sun-filled living room and a kitchen that walks out onto a deck overlooking the quiet back yard. You'll love the rich oak floors throughout. Delivered freshly painted and deep cleaned, this house is

  Layla Rose Boyles Century 21 Realty Center

  12 Mid Oaks Dr, Monroe, NY 10950
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  $560,000

  • 4 Beds
  • 2 Baths
  • 1,721 Sq Ft

  58 James Rd, Monroe, NY 10950

  Escape the city without giving up convenience! Just 45 minutes from NYC, this Village of Monroe home offers the perfect blend of space, flexibility, and opportunity. Sitting on a .41-acre lot, the property is ideal for entertaining, relaxing, or enjoying outdoor activities. Inside, you’ll find a bright kitchen leading to a patio and a large backyard that’s perfect for summer gatherings. The main

  Justina Estrada Keller Williams Hudson Valley

  58 James Rd, Monroe, NY 10950
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  $449,000

  • 3 Beds
  • 3 Baths
  • 1,779 Sq Ft

  36 Weygant Hill, Highland Mills, NY 10930

  Welcome to 36 Weygant Hill Road – a Charming Cape Cod Gem in Highland Mills!Discover this wonderful Cape Cod–style home nestled in the heart of Highland Mills. Situated on a spacious 0.40-acre lot (17,424 sq. ft.), this property offers plenty of room to enjoy the outdoors, complete with a detached garage for added convenience.Step inside to find a warm and inviting kitchen, a cozy living

  David Kraus MK Realty Inc

  36 Weygant Hill, Highland Mills, NY 10930
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  $649,900

  • 5 Beds
  • 2 Baths
  • 2,220 Sq Ft

  33 Winchester Dr, Monroe, NY 10950

  Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room. The

  Dennis Clark Howard Hanna Rand Realty

  33 Winchester Dr, Monroe, NY 10950
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  /19

  $197,500

  • 2 Beds
  • 1 Bath
  • 540 Sq Ft

  50 Woodland Cir S, Monroe, NY 10950

  Discover the perfect blend of classic charm and contemporary style in this beautifully updated 2 bedroom 1 bathroom bungalow. Whether you are seeking a peaceful full time residence or rejuvenating weekend getaway, this home is a turnkey sanctuary in a truly serene setting. Step into an airy, light-filled interior featuring fresh neutral paint and brand-new flooring that flows seamlessly

  Samantha McCrory Exit Realty Connections

  50 Woodland Cir S, Monroe, NY 10950
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  $8,995,000

  • Land
  • 56.2 Acres
  • $160,053 per Acre

  55 Claire Dr, Monroe, NY 10950

  Own the entire neighborhood! 10 buildings, 7 homes, a swimmable, private lake and 56 acres bordering the Village in the Town of Monroe! It's a a meticulously maintained park-like property owned by the same family for many decades. Set-back off of Quaker Hill Road, this Oasis sits at the end of a quaint private road which opens up to a beautiful community of over 11,000sf of housing. Endless

  Layla Rose Boyles Century 21 Realty Center

  55 Claire Dr, Monroe, NY 10950
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  $999,000

  • 3 Beds
  • 1 Bath
  • 1,148 Sq Ft

  168 Prospect Rd, Monroe, NY 10950

  Welcome to your dream home! Lovingly maintained and nestled in a peaceful community, this charming ranch sits on a picturesque one-acre lot.Step inside to a warm and inviting living space, highlighted by a cozy wood-burning stove—perfect for chilly evenings. The home features three comfortable bedrooms and a well-appointed bathroom, offering both comfort and functionality.Enjoy

  Salvatore Girgenti Ben Bay Realty of Staten Isl.

  168 Prospect Rd, Monroe, NY 10950
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  $749,000

  • 3 Beds
  • 4 Baths
  • 2,016 Sq Ft

  220 Prospect Rd, Monroe, NY 10950

  Welcome to this delightful Colonial-style home ideally situated in a desirable Monroe neighborhood. Set on a generous and private lot, this residence offers a comfortable and functional layout with plenty of opportunity for personalization and expansion. Featuring multiple living areas, well-proportioned bedrooms, and an unfinished attic ready for storage or future improvement, this home blends

  Lazar Schvimmer Blooming Realty

  220 Prospect Rd, Monroe, NY 10950
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  $219,900

  • 1 Bed
  • 1 Bath
  • 598 Sq Ft

  36 Paradise Hill, Highland Mills, NY 10930

  Tucked away on a private road in the Town of Cornwall, this charming 600 sq ft cottage offers the perfect blend of privacy, tranquility, and convenience. Whether you’re seeking a full-time residence or a peaceful weekend getaway, this home delivers mountain views and a secluded setting that feels like a true escape. The interior features a spacious living room with large window overlooking the

  Jennifer Gold RE/MAX Benchmark Realty Group

  36 Paradise Hill, Highland Mills, NY 10930
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  $505,000

  • 4 Beds
  • 1.5 Baths
  • 1,528 Sq Ft

  246 Skyline Dr, Highland Mills, NY 10930

  4 Bedroom, 1.5 Bathroom Raised Ranch in Woodbury! Close to I-87 & Woodbury Commons, Sold as-is. Buyer to pay NYS and any local transfer taxes. Cash offers only with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

  Ernie Acampora River Realty Services, Inc.

  246 Skyline Dr, Highland Mills, NY 10930
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  $430,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  13 Butternut Ct, Highland Mills, NY 10930

  If the roads are icy, call for a private tour. A contemporary and updated 3-story townhouse with an attached garage. Upgrades include: Anderson windows, hardwood floors, granite countertops, kitchen appliances (stainless steel), recessed lighting, and millwork surrounding the wood-burning fireplace. The updated kitchen was refreshed with granite counters, tile backsplash, open shelving, stainless

  Lynda Hoss Weichert Realtors

  13 Butternut Ct, Highland Mills, NY 10930
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  $355,000

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  37 Aldo Ct, Monroe, NY 10950

  This unit is conveniently located on the first floor with a ramp for easy access. Experience the ease of single-level living in this home featuring generous rooms, plentiful natural light, and an open floor plan that’s ideal for both relaxation and entertaining. Step through the inviting entryway into a spacious, sun-filled living and dining area that radiates warmth and charm. The kitchen offers

  Donna Gennaro Howard Hanna Rand Realty

  37 Aldo Ct, Monroe, NY 10950
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  /42

  $770,000

  • 4 Beds
  • 2 Baths
  • 1,763 Sq Ft

  10 Lemberg Ct Unit 401, Monroe, NY 10950

  Welcome to this Bright two-floor home corner apartment at an affordable price — a true must-see. A home with a spacious, open layout, a sunny kitchen/dinette with many windows, and an upgraded tiled kitchen with granite countertops and large drawers, plus more. Enjoy multiple rooms: five bedrooms + office room and three full bathrooms + big playroom with lots of spotlights, 9ft ceiling on the

  Jacob Katz MS Realty Group USA, Inc

  10 Lemberg Ct Unit 401, Monroe, NY 10950

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