Highland Mills, NY Homes for Sale under $500,000

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  /6

  $270,000

  $45K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 760 Sq Ft

  32 Cedar Trail, Monroe, NY 10950

  Step into a home where the hard work is already done. Welcome to this 3-bedroom, 1-bath property freshly painted and move-in ready. Nicely flowing layout with updated hardwood flooring, kitchen cabinets with quartz counter, and tiled bathroom were all updated in 2022. New furnace and water heater. Ample space in the backyard.

  

  Jack Yao

  Realmart Realty LLC

  32 Cedar Trail, Monroe, NY 10950
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  /25

  $219,999

  Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  26 East Ave, Washingtonville, NY 10992

  Welcome to this spacious 1,200-square-foot, 3-bedroom, 2-bathroom manufactured home with convenient driveway parking, nestled in the desirable Brookside Acres community within the Town of Blooming Grove and the Washingtonville School District. The heart of the home features a well-appointed kitchen boasting a plethora of oak cabinetry, a full suite of white appliances, and abundant counter space,

  

  Richard Baxter

  Keller Williams Realty

  26 East Ave, Washingtonville, NY 10992
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  /7

  $270,000

  $15K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 704 Sq Ft

  36 Claremont Trail, Monroe, NY 10950

  This charming 2-bedroom ranch has been fully refreshed and is ready for your next chapter. Ideal as a peaceful starter home or a weekend getaway just 60 miles from NYC. Relax on your property and take in the fantastic mountain views that makes this neighborhood one of Orange County’s best-kept secrets. You’re a short drive from Woodbury Common Premium Outlets, local farm-to-table dining, and the

  

  Mindy Skelly

  1 Oak Real Estate Hub Inc

  36 Claremont Trail, Monroe, NY 10950
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  /31

  $395,000

  • 4 Beds
  • 1 Bath
  • 1,132 Sq Ft

  13 Whippoorwill Trail, Monroe, NY 10950

  Your dream home in the cozy Mountain Lodge is here! Come see this beautiful, well kept home in the well sought after Monroe, with Washingtonville schools! Brand new roof! outdoor decking is new, bathroom is new! Call today for a viewing.

  

  Joel Ayala

  HomeSmart Homes & Estates

  13 Whippoorwill Trail, Monroe, NY 10950
• 

  

  

  /23

  $245,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 950 Sq Ft

  18 Lexington Hill Unit 8, Harriman, NY 10926

  Find your perfect home in the heart of Lexington Hills with this desirable lower-level Unit. Experience the best of community living with the added benefit of a secluded, quiet location. Ideal for simplifying life, this unit offers turn-key readiness and is situated just moments from local dining, shopping, and major commuter routes. Enjoy the ease of a lower-level residence with excellent

  

  Donna Reese

  KW Hudson Valley United

  18 Lexington Hill Unit 8, Harriman, NY 10926
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  /34

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,928 Sq Ft

  10 Woodycrest Trail, Monroe, NY 10950

  Welcome home to 10 Woodycrest Trail- tucked away on a quiet no-outlet road with only two homes, this lovingly maintained 4-bedroom, 2 full bathroom home offers the perfect blend of privacy, comfort, and convenience in the heart of Blooming Grove. Owned and meticulously cared for by the same family for 40 years, this property radiates warmth and pride of ownership throughout. The home features an

  Hayley Butterfield LPT Realty Tri-State, LLC

  10 Woodycrest Trail, Monroe, NY 10950
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  /27

  $324,900

  $15K PRICE DROP

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

  308 Magnolia Ct, Highland Mills, NY 10930

  Welcome to 308 Magnolia Court in Highland Mills—a beautifully renovated 2-bedroom, 2-bath condo offering modern finishes and easy, low-maintenance living. This top-floor, second-story unit features an open-concept kitchen with new cabinetry, countertops, appliances, and fixtures. Both bathrooms have been completely updated, while new flooring, fresh paint, and contemporary lighting create a

  Devon King HomeSmart Homes & Estates

  308 Magnolia Ct, Highland Mills, NY 10930
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  /25

  $450,000

  Open Sun 1PM - 3PM $50K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,924 Sq Ft

  22 Center Hill Rd, Monroe, NY 10950

  From the inviting front porch to the flexible upper-level loft, this 4-bedroom, 3-bathroom home in Monroe offers a layout full of warmth, character, and space to make your own. Originally built in 1935, the home was thoughtfully expanded and updated in 2004, blending timeless charm with modern functionality. Step through the front door into the open living and dining area, where hardwood floors

  Trudi Iglesias Howard Hanna Rand Realty

  22 Center Hill Rd, Monroe, NY 10950
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  /25

  $375,000

  • 2 Beds
  • 1 Bath
  • 616 Sq Ft

  24 Round Lake Ave, Monroe, NY 10950

  Nestled on a beautifully maintained lot, this move-in-ready ranch offers timeless charm, hardwood floors, abundant natural light, and an inviting layout perfect for everyday living. The bright kitchen features gas cooking, plenty of cabinetry, and opens seamlessly to the main living area, making entertaining effortless. A welcoming enclosed front porch provides additional living space perfect for

  Kewin Garabito eXp Realty

  24 Round Lake Ave, Monroe, NY 10950
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  /2

  $255,000

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

  31 Tanager Rd Unit 3103, Monroe, NY 10950

  Welcome to 31 Tanager Road, Unit 3103, a brand new construction 2 bedroom, 1.5 bathroom garden-style condo offering the rare opportunity to own brand new living in the established Rolling Hills community! Enjoy pristine, brand new flooring throughout, energy efficient windows, and a kitchen complete with contemporary cabinetry, polished countertops, and brand new appliances. Both bedrooms offer

  Nikki Grzegorzewski Keller Williams Realty

  31 Tanager Rd Unit 3103, Monroe, NY 10950
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  /25

  $399,500

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,551 Sq Ft

  5 Maple Ave, Monroe, NY 10950

  Beautiful Colonial home located in one of the most desirable locations in all of Harriman. A Commuter's dream. 2 Minutes to the Metro North Train Station. 2 Minutes to ALL major commutating Routes including NYS Thruway and the Palisades Parkway. 45 Minutes to NYC. This wonderful home features a NEW ROOF, SIDING,and GUTTERS, UPGRADED ELECTRIC, inviting foyer, Wrap around enclosed porch. Large

  John Biasi Howard Hanna Rand Realty

  5 Maple Ave, Monroe, NY 10950
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  /27

  $450,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  10 Rockridge Dr, Highland Mills, NY 10930

  Welcome to this beautifully sun-filled townhouse located on a cul-de-sac in the desirable Town of Woodbury, Highland Mills, NY. Nestled in a highly sought-after neighborhood, this spacious home offers two primary suites, each featuring walk-in closets and private primary baths. The open floor plan features a bright living room, formal dining area, and convenient half bath. The kitchen offers an

  Idalmis Perrone Aguero Exit Realty DKC

  10 Rockridge Dr, Highland Mills, NY 10930
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  /23

  $310,000

  • 2 Beds
  • 1 Bath
  • 852 Sq Ft

  47 Orchard Lake Dr, Monroe, NY 10950

  This sweet 2-bed, 1-bath ranch offers a bigger feel than you might expect. Inside, you'll find not one, but two living areas, providing plenty of versatility to spread out and make the home work for whatever fits your lifestyle. The first living room greets you as you step through the door, with the bedrooms and bathroom located just off of it, while the more expansive second living room sits on

  Alyssa Woods Howard Hanna Rand Realty

  47 Orchard Lake Dr, Monroe, NY 10950
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  /30

  $349,500

  $50K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,124 Sq Ft

  7 Crestwood Trail, Monroe, NY 10950

  Welcome to this charming 3-bedroom home in Blooming Grove, located within the desirable Washingtonville School District and featuring low taxes. Step into a welcoming living room complete with a cozy, wood-burning fireplace. The space flows seamlessly into a modern eat-in kitchen boasting beautiful granite countertops and abundant cabinetry, highlighted by gleaming wood floors throughout.The

  Olivia Cappelli Donna Ruffino Realty Corp

  7 Crestwood Trail, Monroe, NY 10950
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  /16

  $285,000

  • 2 Beds
  • 1 Bath
  • 1,004 Sq Ft

  5 Point O Pine, Monroe, NY 10950

  Welcome home to this gorgeous, 2-bedroom, possible 3 B/R house. Offering comfortable living space and solid updates. Features a large, comfortable living room, Dining room, open to an efficient kitchen layout, and two well-sized bedrooms. A new roof was installed 3 years ago. The home is located at the end of Point O Pine. Quiet, private location in a nice rural setting. VERY PRIVATE LOCATION

  Yosef Flohr eRealty Advisors, Inc

  5 Point O Pine, Monroe, NY 10950
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  /30

  $249,900

  $30K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 801 Sq Ft

  8 Heritage Dr Unit E, Harriman, NY 10926

  Welcome to this beautifully maintained 1-bedroom, 1-bath condominium in excellent condition. This bright and inviting home features, brand new bathroom, new flooring, new windows and a new sliding glass door that opens to a nice size patio—perfect for relaxing or enjoying your morning coffee. Kitchen features granite countertops and tile backsplash. Lots of closet space. Also there are two new

  Agnes Burch Howard Hanna Rand Realty

  8 Heritage Dr Unit E, Harriman, NY 10926
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  /2

  $375,000

  • Land
  • 1.2 Acres
  • $312,500 per Acre

  188 Roselawn Rd, Highland Mills, NY 10930

  Discover the perfect opportunity to build your dream home on this spacious 1.2-acre parcel of land located at 188 Roselawn Rd in the desirable community of Highland Mills. Tucked away in a peaceful setting, this property offers the ideal blend of privacy and convenience. Situated between County Route 105 & Woodbury Junction, you’ll have easy access to main roads while still enjoying the

  Nathen Singer MK Realty Inc

  188 Roselawn Rd, Highland Mills, NY 10930
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  /50

  $350,000

  Open Sun 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,003 Sq Ft

  4 Hillside Trail, Monroe, NY 10950

  Welcome to 4 Hillside Trail in Monroe!This charming 3-bedroom, 1-bath home offers comfortable living with plenty of space both inside and out. Situated on a desirable corner lot, the property features a fenced-in yard, providing privacy and a great space for pets, play, gardening, or simply enjoying the outdoors. The large patio is perfect for entertaining guests, summer gatherings, or

  Amanda Rivera Sepulveda Keller Williams Realty

  4 Hillside Trail, Monroe, NY 10950
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  /27

  $479,999

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,924 Sq Ft

  124 Barnes Rd, Washingtonville, NY 10992

  WELCOME TO 124 BARNES Rd.! Explore this beautifully kept Extended hi range home nestled in a serene, sought after neighborhood. The home is airy and light filled with a practical layout and convenient living spaces. It features 3 nicely sized bedrooms with a large dining room/ living area, kitchen and finished basement. schedule your tour today!

  Yaakov Bluming MS Realty Group USA, Inc

  124 Barnes Rd, Washingtonville, NY 10992
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  /27

  $459,900

  $108K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,621 Sq Ft

  9 Kings Point Ln, Washingtonville, NY 10992

  Welcome home to this inviting chalet-style property built in 1979, offering 1,620 square feet of comfortable living space on a peaceful 0.96-acre lot. Nestled in the heart of Blooming Grove, this home combines rustic charm with modern convenience—perfect for families looking for space, character, and a warm community setting. This has had a brand new deck added to the large open living area.

  Claude Brischoux Keller Williams Realty

  9 Kings Point Ln, Washingtonville, NY 10992
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  /15

  $205,000

  • 1 Bed
  • 1 Bath
  • 813 Sq Ft

  26 Tanager Rd Unit 2601, Monroe, NY 10950

  NEWLY RENOVATED Summer 2026! New Kitchen and appliances, new quality composite floors throughout, New bathroom and freshly painted. Turn key! Enjoy a sunny and spacious new home. Heat and Hot water included! Located close to the HOA amenities including an inground community pool, play ground, sports areas and more. Sidewalk-lined streets make it safe and relaxing for walks to the pool and the

  Layla Rose Boyles Century 21 Realty Center

  26 Tanager Rd Unit 2601, Monroe, NY 10950
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  /3

  $485,000

  $36K PRICE INCREASE

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft

  10 Meron Dr Unit 113, Monroe, NY 10950

  Get your dream new homes in the HEART OF KIRYAS JOEL. Welcome to this desirable basement, offering privacy and light. The beautiful dining room provides an elegant space for gatherings, while the spacious kitchen offers plenty of room to cook, host, and enjoy everyday living comfortably.

  Moses Zwiebel MS Realty Group USA, Inc

  10 Meron Dr Unit 113, Monroe, NY 10950
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  /30

  $449,555

  Open Sat 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,751 Sq Ft

  132 Ridge Rd, Highland Mills, NY 10930

  Welcome to this beautiful and inviting Colonial! This charming 3-bedroom, 1.5-bath home offers the perfect blend of comfort, style, and modern updates in a highly desirable area.Step inside to find brand-new, high-quality vinyl flooring and recessed lighting throughout the home, creating a fresh, modern, and welcoming atmosphere. The spacious eat-in kitchen features brand-new cabinetry,

  Jessenia Acosta Century 21 Full Service Realty

  132 Ridge Rd, Highland Mills, NY 10930
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  /21

  $499,000

  Open Sat 11AM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,884 Sq Ft

  10 Andre Dr, Highland Mills, NY 10930

  Welcome to 10 Andre Drive, a spacious four-bedroom, two-bath split level home situated on 0.35 beautifully landscaped acres in Highland Mills. In addition to the home’s three bedrooms, the finished lower level features two additional rooms, providing valuable flexible space for home offices, a gym, recreation room, guest space, hobby room, or other uses to fit your needs. An attached garage and

  Warren Mitchell Opulence Realty Group

  10 Andre Dr, Highland Mills, NY 10930
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  /24

  $479,999

  • 3 Beds
  • 2.5 Baths
  • 1,963 Sq Ft

  19 Helene Cir, Highland Mills, NY 10930

  Welcome home to this beautifully custom-renovated 3-bedroom, 2.5-bath townhouse nestled on a quiet cul-de-sac in the highly sought-after Timber Ridge III community of Highland Mills. Offering approximately 1,963 square feet of living space, including the finished basement with an impressive oversized his-and-hers walk-in closet, this move-in-ready home combines modern style, comfort, and

  Jarel Carroll Exit Realty DKC

  19 Helene Cir, Highland Mills, NY 10930
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  /50

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,215 Sq Ft

  42 Natale Ct, Monroe, NY 10950

  Welcome home to this inviting 3-bedroom, 2-full-bath condominium in the Town of Monroe! Featuring a comfortable layout with a cozy fireplace and a kitchen that opens directly to the deck, creating the perfect space for morning coffee, outdoor dining, or relaxing after a long day. The full basement offers excellent potential to create additional living space, a home office, recreation room, gym,

  Sammy Zambrano Keller Williams Realty

  42 Natale Ct, Monroe, NY 10950
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  /2

  $250,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 944 Sq Ft

  21 Grandview Trail, Monroe, NY 10950

  Set in the heart of Mountain Lodge Park, this well-maintained 2-bedroom home offers a peaceful setting surrounded by nature while remaining close to everything you need. The backyard provides a private outdoor escape, perfect for entertaining, gardening, or simply unwinding after a long day. Inside, the home features a comfortable floor plan, forced-air heat, and a full basement with excellent

  Martin Remo RE/MAX Prime Properties

  21 Grandview Trail, Monroe, NY 10950
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  /20

  $339,999

  $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,302 Sq Ft

  12 Cascade Trail, Monroe, NY 10950

  Escape to your own private woodland retreat with this beautifully renovated year-round home in Mountain Lodge Park. Surrounded by mature trees and offering a true cabin-like feel, this charming property combines rustic character with modern conveniences.Inside, you'll find two generously sized bedrooms and a stunning newly renovated full bathroom featuring double rainfall shower heads for

  Jennifer Rivera Keller Williams Realty

  12 Cascade Trail, Monroe, NY 10950
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  /49

  $329,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,902 Sq Ft

  2 Echo Trail, Monroe, NY 10950

  Welcome to this charming 3-bedroom colonial home, offering comfort and modern updates throughout. The home features three nicely sized bedrooms filled with natural light and ample closet space.The main level includes a spacious kitchen and a large dining/living room, perfect for everyday living and entertaining. A bright home office with a cozy fireplace adds warmth and character to the

  Avi Samet Avion

  2 Echo Trail, Monroe, NY 10950
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  /5

  $225,000

  $25K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 947 Sq Ft

  23 Grandview Trail, Monroe, NY 10950

  Surrounded by nature in Mountain Lodge Park, this charming 1-bedroom home offers a peaceful setting without sacrificing convenience. The private backyard, framed by mature trees, provides the perfect place to relax, entertain, or simply enjoy the tranquility of the outdoors. Inside, you'll find a functional single-level layout featuring a first-floor bedroom and full bath, forced-air heat, a

  Martin Remo RE/MAX Prime Properties

  23 Grandview Trail, Monroe, NY 10950
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  /6

  $249,900

  $49K PRICE DROP

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

  7 Summit Trail, Monroe, NY 10950

  Ready to sell. Charming 3 bedroom, 2 bath ranch home on beautiful flat property. Extra room off of the kitchen. Updated flooring. New roof being installed currently.

  Elly Walden Howard Hanna Rand Realty

  7 Summit Trail, Monroe, NY 10950
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  /50

  $425,000

  • 2 Beds
  • 2.5 Baths
  • 1,569 Sq Ft

  60 Rockridge Dr, Highland Mills, NY 10930

  Welcome to this beautifully maintained townhouse in Highland Mills offering 2 bedrooms, 2.5 baths, and 1,569 square feet of thoughtfully designed living space. Built in 2001, the home features an open-concept main level with hardwood floors, a spacious kitchen with white cabinetry, stainless-steel appliances and dark countertops, and a bright dining area that opens directly to the rear deck.

  Virginia Corbett eXp Realty

  60 Rockridge Dr, Highland Mills, NY 10930
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  /39

  $285,000

  • 2 Beds
  • 1 Bath
  • 799 Sq Ft

  21 Woodycrest Trail, Monroe, NY 10950

  Monroe now offers this BEAUTIFUL 2 Bedroom 1 Bath Ranch that sits on a quiet trail with Washingtonville School District. A front deck where you can enjoy morning coffee welcomes you into your new home! Enter into a tiled eat in kitchen with plenty of cabinet space and beautiful stainless steel appliances. This open concept kitchen has all the space you need allowing for a large dining area to

  Sandra Arnez KW Hudson Valley United

  21 Woodycrest Trail, Monroe, NY 10950
• 

  

  /22

  $425,000

  Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 2,120 Sq Ft

  14 Helms Hill Rd, Washingtonville, NY 10992

  Unlock the Potential of This Spacious Raised Ranch in Washingtonville!Set on over an acre in a desirable Washingtonville location, this large raised ranch offers plenty of space, privacy, and opportunity to create the home you’ve been envisioning. With a generous layout and great bones, this property is ready for someone with a vision to bring it back to its full potential. The lower

  Lauren Kelly Howard Hanna Rand Realty

  14 Helms Hill Rd, Washingtonville, NY 10992
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  /45

  $389,000

  • 4 Beds
  • 1 Bath
  • 1,432 Sq Ft

  4 Grove St, Harriman, NY 10926

  Welcome to 4 Grove St, a charming and private residence nestled in the heart of Harriman, NY. This inviting home offers 4 spacious bedrooms and a total of 7 bright, versatile rooms—perfect for living, entertaining guests, or creating your ideal home office or playroom. Set on a generous 0.7-acre lot, the property provides ample outdoor space for relaxing, gardening, or enjoying gatherings in your

  David Kraus MK Realty Inc

  4 Grove St, Harriman, NY 10926
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  /24

  $436,000

  • 2 Beds
  • 1 Bath
  • 1,125 Sq Ft

  10 Forshee St, Monroe, NY 10950

  Gorgeous Turn-Key Ranch – One-Level Living at Its Finest. Move right into this beautifully renovated 2-bedroom, 1-bath home, perfectly situated on a lush, well-maintained property surrounded by mature trees and abundant natural light. Meticulously updated and thoughtfully designed, this home offers comfort, style, and convenience.Features Include: Updated eat-in kitchen with granite

  Amanda Dnistrian ARC Realty 1 in Sales

  10 Forshee St, Monroe, NY 10950
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  /24

  $479,999

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  172 Ridge Rd, Highland Mills, NY 10930

  Welcome to 172 Ridge Road, a delightful 3-bed, 2-bath split-level home offering 1,600 sq ft of comfortable living space in the heart of Highland Mills. With plenty of space to possibly expand both above and behind the house, the opportunities here are endless. Park easily in your two-car garage and driveway, then step into a home situated on nearly half an acre of yard that invites backyard

  JOHN SCARANO Keller Williams Realty

  172 Ridge Rd, Highland Mills, NY 10930
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  /11

  $349,000

  • 3 Beds
  • 1 Bath
  • 882 Sq Ft

  65 Glenwood Rd, Monroe, NY 10950

  Welcome home to this beautifully redone, move-in-ready ranch-style single-family home!Combining one-level efficiency with high-end modern features, this bright and inviting 3-bedroom, 1-full-bath residence has undergone a full, top-to-bottom renovation.Key Features & Highlights* Open & Sunlit Living Space: Bathed in natural light from abundant wide windows.* Cozy

  Abraham Malik A Malik Real Estate

  65 Glenwood Rd, Monroe, NY 10950
• 

  

  /25

  $430,000

  $35K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 952 Sq Ft

  21 Shuit Place, Central Valley, NY 10917

  Make This cozy comfortable House Yours Today!! Introducing a stunningly renovated 3-bedroom, 1-bathroom detached home that embodies both comfort and style. this beautifully updated property features a spacious garden, perfect for gardening enthusiasts or those who cherish outdoor relaxation. Completely transformed in 2023, everything inside has been updated to reflect modern living standards

  Aron Ungar eRealty Advisors, Inc

  21 Shuit Place, Central Valley, NY 10917
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  /39

  $369,900

  $25K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,334 Sq Ft

  7 Ironwood Dr, Highland Mills, NY 10930

  Luxury Living at its very Best! 45 min to NYC. This Gorgeous Home features Bamboo Flooring Throughout, New Windows, Doors and Water Softener. Inviting Entry with Vaulted Ceilings and Skylight. Designer High End Kemper Kitchen, with beautiful Granite Countertops with breakfast Bar, with Pendulum lighting, Tumbled Marble Backsplash, Top of the Line Jen Air Refrigerator & Dishwasher, Capital

  John Biasi Howard Hanna Rand Realty

  7 Ironwood Dr, Highland Mills, NY 10930

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