Highland Mills, NY Homes for Sale

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  /45

  $680,000

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  28 Sutherland Dr, Highland Mills, NY 10930

  "Hike Up Your Own Mountain" – A Serene and Spacious Woodland RetreatWelcome to your private sanctuary nestled on 2.4 acres of lush woods and cultivated gardens, where nature and modern living harmoniously intertwine. This beautifully updated home invites you in with a charming front porch, perfect for morning coffee or evening relaxation, offering a warm welcome to all who arrive.Inside,

  

  Regina Wittosch

  Howard Hanna Rand Realty

  (845) 868-6382

  28 Sutherland Dr, Highland Mills, NY 10930
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  /41

  $649,000

  • 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 has to offer. Step inside to discover a bright and spacious interior featuring a stylish

  

  Zachary Leentjes

  Wansor Realty

  (329) 201-2257

  300 Mountain Lodge Rd, Monroe, NY 10950
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  /2

  $799,000

  • 4 Beds
  • 1 Bath
  • 1,400 Sq Ft

  24 Laura Ln, Woodbury, NY 10917

  The ol' poultry farm.... a cozy Arts and Craft style home with 4 bedrooms 1 bathroom and a walkout basement! Located at the end of a dead end street saturated by commercial neighbors! Value is in the land... Ideal use is for commercial business right in Central Valley! Call for other details and ideas- Taxes are Town and County $2,100; Village $1,400; School $5,200 Survey will be uploaded when

  

  Erin Connolly

  Artisan Realty

  (845) 205-7720

  24 Laura Ln, Woodbury, NY 10917
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  /31

  $285,000

  • 2 Beds
  • 1 Bath
  • 838 Sq Ft

  9 Ludwig Dr, Monroe, NY 10950

  Welcome to this cozy and well-maintained 2-bedroom ranch located on a quiet residential street in Monroe. The home features a bright living room highlighted by a beautiful bay window, a spacious eat-in kitchen with access to the rear deck, and a functional one-level layout. Enjoy a level, generously sized backyard ideal for outdoor use. Additional features include a one-car attached garage and

  

  Alison Orlando

  Keller Williams Hudson Valley

  (329) 219-1180

  9 Ludwig Dr, Monroe, NY 10950
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  /50

  $699,999

  • 4 Beds
  • 2.5 Baths
  • 2,448 Sq Ft

  120 Pine Tree Rd, Monroe, NY 10950

  Welcome to 120 Pine Tree Road, a beautifully maintained Colonial in Monroe offering over 2,450 sq ft of comfortable living in the Monroe-Woodbury School District. This home features a sunken living room with hardwood floors, an elegant flow into the dining area, and marble flooring throughout the kitchen and dining room for a refined finish. The second level provides four generous bedrooms,

  

  Alison Orlando

  Keller Williams Hudson Valley

  (329) 777-5921

  120 Pine Tree Rd, Monroe, NY 10950
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  /38

  $794,999

  • 5 Beds
  • 4 Baths
  • 4,615 Sq Ft

  108 Circle Dr, Monroe, NY 10950

  ** New Heating System***This stunning contemporary Cape Cod offer's nearly 5,000 Sqft of elegant living space sitting pretty on 2.1 Acres with Monroe Woodbury Schools. Perfect for a large or multi-generational families, step inside to find three spacious living/sitting/family rooms, gleaming hardwood floors, and a luxurious stone mantle with gas fireplace. The bedrooms are oversized including a

  

  Alexandra Zinko

  Century 21 Realty Center

  (329) 215-0421

  108 Circle Dr, Monroe, NY 10950
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  /15

  $369,000

  • 2 Beds
  • 1.5 Baths
  • 1,284 Sq Ft

  26 Linden Dr, Highland Mills, NY 10930

  PRIME end unit Townhouse style home with detached garage and upgrades galore...Prime and pristine are just the start to describe this very rare Townhouse style home! Offering 2 bedrooms 1 1/2 baths and modern Kitchen area with a sun drenched living room and dining room open floor plan! It gets better! BONUS END UNIT & A BETTER BONUS... GARAGE !! Central Air Municipal Water / Sewer with a Pool and

  

  Erin Connolly

  Artisan Realty

  (845) 310-0399

  26 Linden Dr, Highland Mills, NY 10930
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  /44

  $795,000

  • 3 Beds
  • 2 Baths
  • 2,175 Sq Ft

  17 Merriewold Ln N, Monroe, NY 10950

  Nestled in nature, welcome to your private sanctuary in the heart of the highly desirable Merriewold Lake community in South Blooming Grove—where serenity meets thoughtful design and comfort. From the moment you arrive, the attention to detail is unmistakable. The home’s inviting front elevation features a covered porch with solid mahogany decking and recessed lighting—creating a warm and

  

  Christina Rowan

  Howard Hanna Rand Realty

  (845) 379-3531

  17 Merriewold Ln N, Monroe, NY 10950
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  /12

  $259,900

  • 3 Beds
  • 1 Bath
  • 784 Sq Ft

  22 Sylvan Trail, Monroe, NY 10950

  Location, location, location! Great opportunity to own this fully renovated Single Family house in the heart of Monroe!! Schedule your appointment before it's gone!

  

  Santiago Jaraba

  P R O Links Realty Inc

  (329) 217-0156

  22 Sylvan Trail, Monroe, NY 10950
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  /20

  $525,000

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

  5 Seeley Bull St, Monroe, NY 10950

  Introducing Hidden Creek Community. A private oasis of modern developed Townhomes. Here we have a bi-level , 3 bedroom 2 and a 1/2 balf, with basement and 2 car garage, sophisticatedly laid out across over 2100 sqft. A home outfitted with all the swanky finishes from stainless steal appliances, contrast gold kitchen faucet and cabinetry handles grounded by most luxurious marble flooring. Master

  Michael George Nest Seekers LLC

  5 Seeley Bull St, Monroe, NY 10950
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  /41

  $810,000

  • 6 Beds
  • 3.5 Baths
  • 4,517 Sq Ft

  3 Caledonia Cir, Highland Mills, NY 10930

  Welcome to 3 Caledonia Circle: A Luxurious Haven in the Brigadoon Community Imagine stepping into a stunning home that exudes elegance and sophistication. The beautiful big house boasts a majestic double-ceiling entryway with big chandeliers that sparkle and shine, setting the tone for a luxurious living experience. The expansive living room is a bright and airy space with double ceilings and

  Yakov Winkler Preferred Properties Real Esta

  3 Caledonia Cir, Highland Mills, NY 10930
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  /43

  $599,999

  • 3 Beds
  • 2 Baths
  • 1,755 Sq Ft

  106 Maple Ave, Monroe, NY 10950

  WELCOME TO 106 MAPLE AVE AND LOOK NO FURTHER! Finally, your forever home! This very spacious (circa 1900) colonial served as home to a lovely family for over 45 years where their pride in ownership is evident to this day. The well-manicured property and charming wrap-around porch with field stone pillars lend to this home’s incredible curb appeal. Wrap-around porches are highly desirable and

  Vincent McAteer Terrie OConnor

  106 Maple Ave, Monroe, NY 10950
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  /39

  $819,000

  • 4 Beds
  • 3.5 Baths
  • 3,235 Sq Ft

  46 Woodland Rd, Monroe, NY 10950

  Tucked away in a peaceful, tree-lined neighborhood, 46 Woodland Rd offers the perfect balance of tranquil suburban living and modern comfort. This beautifully maintained home sits on a generous lot, surrounded by mature trees — giving you that secluded, “upstate getaway” vibe, while still being just minutes from Monroe’s shops, restaurants, and top-rated schools.Step inside to find a

  Alejandra Fermin Empire Fine Homes

  46 Woodland Rd, Monroe, NY 10950
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  /50

  $929,000

  • 4 Beds
  • 4.5 Baths
  • 3,410 Sq Ft

  208 Oakland Ave, Monroe, NY 10950

  Welcome to this beautifully maintained 3 bedroom 2.5 bath Center Hall Colonial with a 1 bedroom 2 bath plus kitchen accessory apartment, where pride of ownership shines through every detail. Nestled in the heart of the Village of Monroe, this special home offers timeless charm, modern amenities, and a luxurious accessory apartment—perfect for extended family or guests.Step into the elegant

  Claudia Lepore Keller Williams Realty

  208 Oakland Ave, Monroe, NY 10950
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  /2

  $325,000

  • Land
  • 0.23 Acre
  • $1,413,043 per Acre

  8 First Ave, Monroe, NY 10950

  This spacious lot offers an excellent opportunity to build a custom home in a sought-after neighborhood. Ample space allows for both a personalized residence and outdoor living areas. The adjacent lot at 10 First Ave is also available, providing options to expand your property or accommodate others nearby. The site is fully serviced with sewer, water, natural gas, and electricity, streamlining

  Moshe Kaufman MK Realty Inc

  8 First Ave, Monroe, NY 10950
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  /49

  $1,490,000

  • 4 Beds
  • 2.5 Baths
  • 3,150 Sq Ft

  421 Spring St, Monroe, NY 10950

  Introducing The Spring Hill House, a rare gem in the heart of Monroe, a short stroll to Kiryas Joel Gate shopping & conveniences. Set on 2.6 serene, park-like acres, this Queen Ann estate, offers both a grand main house & a potential accessory home. The elegant interior boasts a custom kitchen w/ luxurious marble & onyx backsplashes & countertops hardwood floors, formal dining room, living room,

  Harry Donofrio Town and Village Real Estate

  421 Spring St, Monroe, NY 10950
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  /32

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 2,002 Sq Ft

  300 Estrada Rd, Central Valley, NY 10917

  Tucked away at the end of a quiet street in Central Valley, this rare 22.6-acre property offers an incredible opportunity just one hour from NYC. These owners have built the home in 1975; the land and home have been lovingly owned by the same family—and now it's ready for its next chapter. Whether you're dreaming of your own private retreat or seeking a unique investment opportunity, this

  Rosalie Cook Weichert Realtors

  300 Estrada Rd, Central Valley, NY 10917
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  /13

  $559,888

  • 4 Beds
  • 3 Baths
  • 2,156 Sq Ft

  1 Grant Ct, Highland Mills, NY 10930

  UPDATED 4 BEDROOM, 3 F BATH, 2456 SQ. FT. HI-RANCH WITH 2 KITCHENS, 2 CAR ATTACHED GARAGE, AND A BEAUTIFUL POOL IN THE BEST SCHOOL DISTRICT IN ORANGE COUNTY........................LAYOUT- 1ST FLOOR, SUMMER KITCHEN, FULL BATH, BEDROOM, LR, FIREPLACE................ 2ND FLOOR, 3 BEDS, MASTER WITH A F BATH, KIT, LR, DR, ANOTHER F BATH............... THIS IS PRIME REAL ESTATE LOCATED IN THE TOWN OF

  Joseph Lombardo Listing by Lombardo Homes & Estates

  

  1 Grant Ct, Highland Mills, NY 10930
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  /50

  $899,000

  • 4 Beds
  • 3 Baths
  • 4,231 Sq Ft

  8 Alloway Crescent, Highland Mills, NY 10930

  Welcome to this beautiful center hall colonial in Highland Mills' Brigadoon Community. Proudly offered by the original owners of over two decades years, this wonderful home features a custom layout that makes it truly special. A welcoming front porch invites you into the main foyer, where you’ll find a spacious living room to the left and a formal dining room to the right — perfect for gatherings

  Claudia Lepore Keller Williams Realty

  8 Alloway Crescent, Highland Mills, NY 10930
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  /30

  $660,000

  • 3 Beds
  • 2 Baths
  • 1,987 Sq Ft

  39 Peddler Hill Rd, Monroe, NY 10950

  Welcome to your dream home in the heart of Monroe, NY—where modern elegance meets everyday convenience. This beautifully appointed 1,987 sq ft raised ranch offers a perfect blend of contemporary design, generous living space, and a prime location just one hour from New York City. With 3 spacious bedrooms, 2 updated bathrooms, and a layout crafted for both comfort and style, this home is ready to

  Jessica Evans Keller Williams Hudson Valley

  39 Peddler Hill Rd, Monroe, NY 10950
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  /24

  $165,000

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft

  9 Higgins Trail, Monroe, NY 10950

  Ready to secure your Spring/Summer getaway home in the Hudson Valley? 9 Higgins Trail is just that! A newly renovated, turn-key retreat nestled in the heart of Mountain Lodge Park! Step inside to a spacious recreation room that sets the tone for easy flow throughout the home. The living area connects to the kitchen via a charming breakfast bar, creating a perfect space for entertaining, relaxing,

  Nicholas Cuomo Keller Williams Realty

  9 Higgins Trail, Monroe, NY 10950
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  /39

  $499,000

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  46 Quaker Hill Rd, Monroe, NY 10950

  Welcome to 46 Quaker Hill Road – your dream retreat! This beautifully updated three-bedroom, two-bath Cape Cod seamlessly blends charm, comfort, and modern living. Step inside to discover a warm and inviting interior featuring a classic brick fireplace—perfect for cozy nights—and a thoughtful layout designed for both relaxation and entertaining. Just off the living room, a newly renovated bedroom

  Deneen Rispo eXp Realty

  46 Quaker Hill Rd, Monroe, NY 10950
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  /10

  $223,500

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  34 Laurel Trail, Monroe, NY 10950

  Blooming Grove! SELLER IS VERY MOTIVATED. THE OWNER IS SEEKING A QUICK CLOSING. THIS PRESENTS AN EXCELLENT OPPORTUNITY FOR A GREAT DEAL.Fully available!! Affordable ranch with ADJOING LOT INCLLUDED! Great ranch featuring a welcoming interior and a good-sized living room. Very good condition with fresh paint. Eat in kitchen with door leading to the back deck. Other features: central air, shed,

  Mordechai Jacobs Q Home Sales

  34 Laurel Trail, Monroe, NY 10950
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  /15

  $200,000

  • 2 Beds
  • 1 Bath
  • 550 Sq Ft

  20 Oakwood Trail N, Monroe, NY 10950

  Nature Lovers Paradise! 2 Bedroom, 1 Bath Cottage, 550 Sq. Ft. Good Condition, Recently Painted, Two Living Room Skylights. Washer-Dryer in Unit. Now ONLY $200000. Near the top of Schunnemunk Mt., Nice Views. Very Private Area. Great Hiking Area, thousands of acres of NY State, preserved land at this location. Baseboard, Gas Heat system and wood stove to heat home. Large Deck. Previously Used as

  Charles J. Izzo Coldwell Banker Realty

  20 Oakwood Trail N, Monroe, NY 10950
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  /26

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  1 Tappan Dr, Monroe, NY 10950

  Welcome to 1 Tappan Drive, a charming lakefront home nestled in the Village of South Blooming Grove. This inviting 4-bedroom, 2-bathroom residence offers comfortable living and stunning lake views. The main level provides ample space for relaxation and entertaining, while the finished walk-out basement features a separate unit. Situated on a spacious 0.53-acre lot, this home enjoys central air

  Shalom Landau eRealty Advisors, Inc

  1 Tappan Dr, Monroe, NY 10950
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  /35

  $599,999

  • 3 Beds
  • 2.5 Baths
  • 1,880 Sq Ft

  77 Woodbury Rd, Highland Mills, NY 10930

  Nestled in the coveted Cornwall School District, this home is in Highland Mills and offers a perfect blend of convenience and charm. Ideal for commuters, the property is situated just minutes away from both the NYS Thruway and Route 17, making it an excellent choice for those traveling to NYC as well as for access to public transportation. This traditional home has three spacious bedrooms, and

  Annie Hansen Howard Hanna Rand Realty

  77 Woodbury Rd, Highland Mills, NY 10930
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  /38

  $678,999

  • 3 Beds
  • 2.5 Baths
  • 2,386 Sq Ft

  35 Depalma Dr, Highland Mills, NY 10930

  Opportunity & LOCATION! Renovated and well maintained split-level style home in Highland Mills/Woodbury NY. This impressive home offers over 2300 sqft. Bright dining/living/family rooms with lots of spotlights and loaded with windows throughout. Large eat in kitchen features granite countertops, and costume wood cabinetry. 3 spacious and sunny bedrooms 2.5 baths, master with jetted tub and

  Eliezer Safdie Sage Realty Center LLC

  35 Depalma Dr, Highland Mills, NY 10930
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  /40

  $799,900

  • 5 Beds
  • 5 Baths
  • 4,089 Sq Ft

  20 Bernadette Way, Washingtonville, NY 10992

  Welcome to a one of a kind opportunity in the heart of Washingtonville. This expansive raised ranch with a stunning two story contemporary addition offers the perfect blend of space, style, and flexibility. With five bedrooms and four full baths this property is ideal for multi generational living or as an income producing multi unit setup. The home showcases gourmet kitchens with granite

  Anesha Nesbitt eXp Realty

  20 Bernadette Way, Washingtonville, NY 10992
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  /35

  $369,000

  • 2 Beds
  • 1 Bath
  • 1,500 Sq Ft

  72 Smith Clove Rd, Central Valley, NY 10917

  Discover the charm of this country-style house in Central Valley, situated in the historic village area. You'll be close to shopping, restaurants, Woodbury Commons, and the Monroe-Woodbury School District. This two-story colonial features a freshly painted interior with cozy accents, a beautiful staircase, an enclosed front porch, and an updated kitchen. Enjoy the spacious rear yard deck

  Chaim Gluck eRealty Advisors, Inc

  72 Smith Clove Rd, Central Valley, NY 10917
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  /11

  $579,000

  • 5 Beds
  • 2.5 Baths
  • 2,288 Sq Ft

  3 Carroll Dr, Highland Mills, NY 10930

  You won't believe your eyes! Come and see this stunning, newly renovated cozy house located in a quiet neighborhood, yet close to all community amenities and shopping areas. This property sits on nearly half an acre of land and features brand new stone countertops in the kitchen, which is designed with elegant spotlights throughout the house. The home boasts five oversized bedrooms, each with a

  Joel Basch eRealty Advisors, Inc

  3 Carroll Dr, Highland Mills, NY 10930
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  /2

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 2,500 Sq Ft

  15 Prag Blvd Unit 411, Monroe, NY 10950

  Welcome to convenient living in the heart of Kiryas Joel. This home is perfect for growing families and anyone seeking seamless accessibility. The secure, elevator-accessed building ensures ease of movement, while the interior boasts a spacious, light-filled open floor plan. The unit features a generous 9 rooms, 5 bedrooms, and 3 full bathrooms, with a flexible layout offering 6 rooms on the

  Shalom Landau eRealty Advisors, Inc

  15 Prag Blvd Unit 411, Monroe, NY 10950
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  /12

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  30 Sycamore Ct, Highland Mills, NY 10930

  Welcome to this charming corner-lot townhome in the desirable Town of Woodbury! This spacious 3-bedroom, 2-full-bath home offers the perfect blend of comfort, convenience, and style. The bright and inviting living area features a semi-open layout ideal for both everyday living and entertaining. The kitchen offers plenty of counter space and cabinetry, while the dining area flows seamlessly to the

  Danielle Riggs Keller Williams Hudson Valley

  30 Sycamore Ct, Highland Mills, NY 10930
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  /48

  $780,000

  • 4 Beds
  • 3.5 Baths
  • 3,046 Sq Ft

  115 Brigadoon Blvd, Highland Mills, NY 10930

  wow! welcome to this stunning beautiful colonial on brigadoon blvd! this charming home is a dream come true for those seeking comfort, style, and functionality for living or entertaining! by entering the house, you'll step into a stunning big foyer that WOWS you with its elegance and grandeur! the foyer sets the tone for the beautiful home with its tasteful design and flow into the rest of the

  Yakov Winkler Preferred Properties Real Esta

  115 Brigadoon Blvd, Highland Mills, NY 10930
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  /29

  $435,000

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

  13 Butternut Ct, Highland Mills, NY 10930

  The BEST IN TIMBER RIDGE ! Now you can have it ALL! Spacious townhome with ATTACHED GARAGE! NOT ALL HOMES in TIMBER RIDGE have interior access from the private GARAGE, right into FINISHED BASEMENT! Now that winter is here, you will LOVE this convenience! Perfect home for entertaining large groups of friends and family in your BEAUTIFUL LIVING ROOM/GREAT ROOM WITH GORGEOUS WOOD FLOORS AND CUSTOM

  Joanne Cooper Hudson Heritage Realty

  13 Butternut Ct, Highland Mills, NY 10930
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  /38

  $520,000

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft

  2 Charlotte Place, Monroe, NY 10950

  Welcome to your own private paradise in Monroe! This charming 1,512-square-foot Cape Cod home is a peaceful retreat for modern living. With three bedrooms, two full bathrooms, and a versatile office space that can double as a fourth bedroom, there's plenty of room for everyone to thrive. The true highlight of this property is its 0.55-acre backyard, a secluded oasis perfect for entertaining and

  Hershel Mittelman The Middleman Team

  2 Charlotte Place, Monroe, NY 10950
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  /31

  $725,000

  • 4 Beds
  • 2.5 Baths
  • 2,004 Sq Ft

  4 Sequoia Trail, Highland Mills, NY 10930

  Nestled in the desirable Highland Mills community, 4 Sequoia Trail presents a beautifully updated 2,004 sq ft residence offering comfort, style, and modern convenience. Set on nicely landscaped grounds with generous outdoor space, this home provides a serene escape while remaining close to everything the area has to offer. The upper level features a bright, inviting living room with oversized

  Hershy Niederman Loop Realty Inc

  4 Sequoia Trail, Highland Mills, NY 10930
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  /29

  $568,000

  • 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. Step inside to a bright and open living area featuring a cozy wood

  Claude Brischoux Keller Williams Realty

  9 Kings Point Ln, Washingtonville, NY 10992
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  /40

  $447,000

  • 4 Beds
  • 1 Bath
  • 1,225 Sq Ft

  2 Cedar Rd, Highland Mills, NY 10930

  Charming Cape in Highland Mills – A Gardener’s Paradise with Modern Upgrades! Nestled in the scenic mountains of Highland Mills, this enchanting “Little Yellow House” sits proudly on a corner lot, offering the perfect blend of character, comfort, and modern convenience. Boasting 4 bedrooms and 1 bath, this Cape-style home is a true retreat for gardeners, entertainers, and families alike. Step

  Zakia Wisdom Z Wisdom Realty Inc.

  2 Cedar Rd, Highland Mills, NY 10930
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  /35

  $379,000

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

  19 Grandview Trail, Monroe, NY 10950

  Welcome to this stunning newly renovated home located in the heart of Monroe, offering the perfect blend of modern comfort and convenience. Situated within the highly sought-after Washingtonville School District, this 3-bedroom, 2-bathroom property is designed to impress. Step inside to an inviting open-concept layout filled with natural sunlight, gleaming hardwood floors, and vaulted ceilings

  Courtney Tablante Keller Williams Realty

  19 Grandview Trail, Monroe, NY 10950
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  /27

  $14,000,000

  • 14 Beds
  • 6.5 Baths
  • 10,041 Sq Ft

  Unlisted Address

  142 acres with municipal services available. One of the last large lots available in the area. Lots of rental income potential. Caretakers house is occupied. Bring your imagination and restore this house and property to it's former glory. This has been in the same family for almost 100 years. Property is on both sides of Route 32. The eastern side goes all the way down to the train tracks.

  Susan Walski Keller Williams Hudson Valley

  Unlisted Address

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