Highland Mills, NY Homes for Sale under $400,000

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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
• 

  

  

  /19

  $169,000

  $106K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft

  10 Lookout Trail, Monroe, NY 10950

  Home Needs Some Work, but Offers Great Potential to Make It Your Own! 2-bedroom, 1-bath cottage situated on a private 0.25-acre lot in scenic Blooming Grove. This handyman special offers a peaceful, retreat-like setting with plenty of potential to make it your own. Features include a kitchen, living area with a wood-burning stove, natural light, and a covered deck overlooking the wooded

  

  Ewa Kusmierek

  eXp Realty

  10 Lookout Trail, Monroe, NY 10950
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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
• 

  

  

  /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

  $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
• 

  

  /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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  /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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  /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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  /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
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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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  /41

  $189,900

  • 1 Bed
  • 1 Bath
  • 680 Sq Ft

  36 Paradise Trail, Monroe, NY 10950

  Welcome home to a Cozy Cottage a beautifully cared-for property where comfort, style, and peace of mind come together effortlessly. From the moment you arrive, you’ll appreciate the pride of ownership and thoughtful improvements that make this home truly special. Inside, beautiful Pergo flooring (2024) adds a warm, sophisticated feel, while the many recent updates allow you to simply settle in

  Elsie Nunez Keller Williams Realty

  36 Paradise Trail, Monroe, NY 10950
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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
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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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  /2

  $204,999

  $45K PRICE DROP

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

  47 Tanager Rd Unit 4702, Monroe, NY 10950

  Welcome to Rolling Hills in Monroe! This well-maintained 2-bedroom, 1.5-bath garden-style condominium offers comfortable living in a convenient location. Situated on the lower level, this bright and spacious unit features a functional layout with a welcoming entry foyer, galley kitchen, and generous living space. The primary bedroom is complemented by a full bath, while the additional bedroom and

  Joseph Morello KW Hudson Valley United

  47 Tanager Rd Unit 4702, Monroe, NY 10950
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  /18

  $249,600

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

  14 Tanager Rd Unit 1404, Monroe, NY 10950

  Welcome home to 14 Tanager Road, Unit 1404, a beautifully updated 2 bedroom, 1.5 bathroom garden style condo that combines low maintenance living with stylish modern upgrades! Come inside to discover a bright and open layout featuring fresh, durable flooring and updated windows that flood the living space with natural light. The renovated kitchen boasts upgraded cabinetry, beautiful countertops,

  Nikki Grzegorzewski Keller Williams Realty

  14 Tanager Rd Unit 1404, Monroe, NY 10950
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  /38

  $299,900

  $75K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  17 Underhill Trail, Monroe, NY 10950

  Tucked into a peaceful wooded setting, this home offers the space, character, and privacy that are becoming harder to find. Bright interiors feature hardwood floors, skylights, comfortable bedrooms, and plenty of natural light throughout. Multiple decks create a wonderful connection between indoor and outdoor living, offering plenty of space to relax, entertain, or simply enjoy the surrounding

  Moche Halpern Blooming Realty

  17 Underhill Trail, Monroe, NY 10950
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  /2

  $250,000

  • Land
  • 4.5 Acres
  • $55,556 per Acre

  0 Lake Shore Dr Unit KEYH6217208, Monroe Town, NY 10950

  Dolores Serpe Weichert Realtors

  0 Lake Shore Dr Unit KEYH6217208, Monroe Town, NY 10950
• 

  

  /38

  $249,999

  • 1 Bed
  • 1 Bath
  • 835 Sq Ft

  25 Gloria Trail, Monroe, NY 10950

  Tucked away among the peaceful settings of Mountain Lodge Park in Monroe, NY is this charming cabin-style retreat that offers the perfect blend of rustic character and modern comfort. Featuring 1 bedroom, 1 bathroom, a bonus room and a very cool loft. The 688 square feet of thoughtfully designed living space make this unique home on a quiet trail an ideal setting for those seeking privacy and

  Guy Cusumano Howard Hanna Rand Realty

  25 Gloria Trail, Monroe, NY 10950
• 

  

  /19

  $255,000

  $34K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,047 Sq Ft

  22 Woodycrest Trail, Monroe, NY 10950

  Welcome Home ..... SPACIOUS And CHARMING 2-Bedroom / 1-Bath Raised Ranch Nestled In a Peaceful Residential Neighborhood In Monroe. Blending Comfort, Convenience, And Inviting Living Spaces, This Lovely Home Is Ready For You To Move Right In.Inside Find Beautiful HARDWOOD FLOORS throughout And A BRIGHT, SUN FILLED LIVING ROOM Featuring A LARGE BAY WINDOW that Frames Views Of The Front LAWN

  Crystal Jones Voro LLC

  22 Woodycrest Trail, Monroe, NY 10950
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  /2

  $199,000

  • Land
  • 8.4 Acres
  • $23,690 per Acre

  295 Skyline Dr, Highland Mills, NY 10930

  Presenting 295 Skyline Dr in Highland Mills, NY—a rare opportunity on 8.4 sprawling acres. This exceptional property offers the potential to build two single-family houses, making it ideal for developers, investors, or anyone seeking a private estate. Enjoy the tranquility of expansive land in a desirable location, with the flexibility to create your vision. Discover endless possibilities at 295

  Joseph Schwartz MK Realty Inc

  295 Skyline Dr, Highland Mills, NY 10930
• 

  

  /23

  $345,000

  • 3 Beds
  • 1.5 Baths
  • 1,361 Sq Ft

  9 Heritage Dr Unit B, Harriman, NY 10926

  Welcome to Harriman Hills!This beautifully maintained, move-in-ready 3-bedroom, 1.5-bath townhome offers a comfortable layout, modern updates, and low-maintenance living in a desirable community. The main level features a spacious living and dining area with wood flooring, a convenient powder room, and an updated kitchen with stainless steel appliances, and a peninsula with seating.

  Jonathon Lee KW Hudson Valley United

  9 Heritage Dr Unit B, Harriman, NY 10926
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  /50

  $225,000

  $150K PRICE DROP

  • Land
  • 3 Acres
  • $75,000 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

  Lisa Mulcahy Ellis Sotheby's Intl Realty

  331 Mountain Lodge Rd, Blooming Grove, NY 10914
• 

  

  /28

  $220,000

  $21K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  25 Sylvan Trail, Monroe, NY 10950

  Tucked into the mountainside and ideally located just off Mountain Lodge Road, this charming bungalow offers the perfect combination of privacy, character and modern convenience. Situated as the second home along the trail, the property enjoys a peaceful setting surrounded by natural beauty while remaining easily accessible. Classic cedar shake siding adds timeless curb appeal, while the well

  Donna Gennaro Howard Hanna Rand Realty

  25 Sylvan Trail, Monroe, NY 10950
• 

  

  /16

  $349,000

  • 4 Beds
  • 2 Baths
  • 1,267 Sq Ft

  3 Valley Trail, Monroe, NY 10950

  Beautiful, Spacious 4-Bedroom Newly Renovated Home — Great for Homeowners or Investors!Don’t miss this freshly renovated, move-in-ready home featuring beautiful updates,brand-new finishes, and appliances throughout Plenty of SunlightPerfect for homebuyers and first-time buyers looking for an affordable home in a great community, with shopping, schools, and everyday conveniences

  Abraham Malik A Malik Real Estate

  3 Valley Trail, Monroe, NY 10950

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