Homes for Sale near North Main Street School

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  /48

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 5,312 Sq Ft

  53 Gibson Hill Rd, Chester, NY 10918

  Tucked away on over 3 private acres, this recently renovated custom residence offers a rare blend of seclusion, craftsmanship, and elevated living. Surrounded by hundreds of acres of protected state land, the setting ensures unmatched privacy with direct access to nature, including trails that connect to the Appalachian Trail just beyond your backyard. A natural waterfall adds to the serene

  

  Ammar Iqbal

  eXp Realty

  53 Gibson Hill Rd, Chester, NY 10918
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  Explore North Main Street School

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  /37

  $789,900

  • 5 Beds
  • 4 Baths
  • 4,697 Sq Ft

  19 Grand View Terrace, Chester, NY 10918

  Welcome to 19 Grand View Terrace in Chester, NY, an impressive Colonial offering approximately 4,697 square feet, five bedrooms, and four full bathrooms. Set on approximately 0.42 acres, this expansive Orange County residence provides the space, comfort, and flexibility needed for everyday living, entertaining, working from home, and hosting guests.The generous interior features multiple

  

  Randolph Rogers

  eXp Realty

  19 Grand View Terrace, Chester, NY 10918
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  /49

  $700,000

  • 4 Beds
  • 2.5 Baths
  • 3,296 Sq Ft

  13 Bianca Blvd, Chester, NY 10918

  Gracious Colonial home features the best of the traditional style with the appeal of a contemporary open floor plan in the kitchen - family room area. Meticulously maintenance and stylish updates create easy living spaces that are great for daily relaxation as well as entertainment. The full-length deck, large seating area around the fire pit and expansive yard provide outdoor areas to relax,

  Theresa Powers

  Keller Williams Realty

  13 Bianca Blvd, Chester, NY 10918
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  /32

  $860,000

  $20K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,431 Sq Ft

  43 Greenwich Ave, Central Valley, NY 10917

  INCREDIBLE VALUE IN THE GREENS OF WOODBURY! This is your opportunity to own a spacious Colonial in one of the Hudson Valley's most sought-after neighborhoods at an exceptional new price. Offering over 3,400 square feet of living space, this 5-bedroom, 4-full-bath home is ideal for buyers looking to build equity while creating their dream home. Situated in the highly desirable town of Woodbury,

  

  Alexandra Zinko

  Century 21 Realty Center

  43 Greenwich Ave, Central Valley, NY 10917
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  /50

  $825,000

  $14K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,031 Sq Ft

  4 Augusta Ct, Monroe, NY 10950

  Welcome to Mansion Ridge, one of Orange County's premier gated golf course communities, where scenic surroundings, exceptional amenities, and a convenient Hudson Valley location come together. Situated within the sought-after Mansion Ridge community, home to the renowned Jack Nicklaus Signature Golf Course, this spacious 4-bedroom Colonial offers an ideal blend of comfort, functionality, and

  

  Ewa Kusmierek

  eXp Realty

  4 Augusta Ct, Monroe, NY 10950
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  /36

  $749,900

  • 4 Beds
  • 4 Baths
  • 3,080 Sq Ft

  20 Mountainside Dr, Chester, NY 10918

  20 Mountainside Drive, Chester, NY offers a spacious Colonial-style single-family home on approximately 1.6 acres with 4 bedrooms, 2 full baths, 2 half baths, 10 total rooms, and approximately 3,080 sq. ft. of above-ground living space. Built in 2021, this Chester residence features central cooling, gas heat, a full basement, fireplace, covered porch, patio, and Attached garage. Located in Orange

  

  Randolph Rogers

  eXp Realty

  20 Mountainside Dr, Chester, NY 10918
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  /38

  $529,000

  • 4 Beds
  • 2 Baths
  • 1,702 Sq Ft

  171 Barnes Rd, Washingtonville, NY 10992

  Space, character and some unexpected extras come together in this 4-bedroom, 2-bath Colonial in Washingtonville This comfy home offers plenty of space, along with some great features and a few unexpected extras! Hardwood floors run throughout the first floor, which includes a comfortable family room. Central air keeps things comfortable during the warmer months, and the approximately 10-year-old

  

  Carole McCann

  Hudson Heritage Realty

  171 Barnes Rd, Washingtonville, NY 10992
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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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  /19

  $179,000

  $96K 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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  /34

  $550,000

  Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,216 Sq Ft

  16 Cambridge Cir, Monroe, NY 10950

  From the covered front porch to the spacious backyard, this four-bedroom, two-and-a-half-bath home offers plenty of room to live, gather and enjoy. Inside, hardwood floors flow through the bright living and dining rooms, while the kitchen features ample cabinetry, generous counter space and a center island. The vaulted family room with fireplace is the heart of the home, creating a warm and

  

  Kassandra Mott

  KW Hudson Valley United

  16 Cambridge Cir, 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
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  /23

  $500,000

  $499K PRICE INCREASE

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  74 Heaton Rd, Monroe, NY 10950

  Welcome to the town of Chester New York! Step inside to hardwood floors and a welcoming eat-in kitchen featuring stainless steel appliances, ceramic tile flooring and soft-close cabinetry and drawers. Both full bathrooms have been beautifully updated with newer showers, tile and fixtures, plus the everyday luxury of HEATED FLOORS. Includes the rights to use Walton Lake Park.The major

  

  Barbara Bloch

  Coldwell Banker Realty

  74 Heaton Rd, Monroe, NY 10950
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  /56

  $3,999,999

  • 15 Beds
  • 24 Baths
  • 12,000 Sq Ft

  43 Freeland St, Monroe, NY 10950

  Multi-Use Investment Opportunity - Village of Monroe, NY Approx. 12,000 sq ft multi-use building situated on a private gated 2.9-acre property in the Village of Monroe. Built in 2020, the property offers modern construction and flexible layout suitable for a variety of permitted uses. Property currently being used as a private high school with dormitory and both residential units as residence.

  

  Nazma Sooknanan

  Nazma Real Estate LLC

  43 Freeland St, 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
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  /44

  $769,000

  $30K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,505 Sq Ft

  1199 E Mombasha Rd, Monroe, NY 10950

  Truly one of a kind, fully renovated home. Offers privacy, yet close to everything, set on a hilltop overlooking a bubbling brook and Little Dam Lake! Commuters dream with just a short ride to Route 17 and the Thruway.Home features an oversized master bedroom with its own private bath and a wood sauna, library and decks on every floor.

  

  Inna Sobel

  Atelier Properties LLC

  1199 E Mombasha Rd, Monroe, NY 10950
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  /35

  $349,999

  $50K PRICE DROP Pre-Foreclosure

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  241 Meadow Ave, Chester, NY 10918

  Discover the timeless charm and endless potential of this classic Colonial farmhouse, ideally situated on just under one level acre in the heart of Chester, NY. Offering approximately 1,560 square feet of living space, this 4 bedroom, 2 bath home is filled with character and craftsmanship.Step inside to find original hardwood floors, a cozy wood-burning stove, and an artistic, welcoming

  

  Chativa Bowen

  Keller Williams Realty

  241 Meadow Ave, Chester, NY 10918
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  /34

  $649,000

  • 5 Beds
  • 3 Baths
  • 3,448 Sq Ft

  67 Carol Dr, Monroe, NY 10950

  Large & Spacious expanded 5-bedroom, 3 bath raised ranch sits on a private level acre in Monroe, offering exceptional potential for its next owner. The home features a generous floorplan with 4 bedrooms on the main level, a bright kitchen, formal livingroom, central air, fireplace, hardwood-floors in the living room, roof (2019) Furnace (2018) and newer Hot Water Heater (2021). The primary

  

  Joan Wortmann

  Weichert Realtors

  67 Carol Dr, Monroe, NY 10950
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  /29

  $619,990

  Open Sat 12PM - 2PM $49K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,012 Sq Ft

  95 Pine Hill Rd, Highland Mills, NY 10930

  Welcome to 95 Pine Hill Rd. in Highland Mills, NY! This spacious 4-bedroom, 2.5-bath Colonial is located in a highly sought after area offers the perfect blend of comfort, convenience, and outdoor enjoyment. The kitchen features granite countertops, stainless steel appliances, and plenty of cabinet space, making it ideal for everyday living and entertaining. Enjoy summer days in your private

  

  Haakim Byrd

  HomeSmart Homes & Estates

  95 Pine Hill Rd, Highland Mills, NY 10930
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  /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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  /2

  $4,850,000

  • 52 Beds
  • 25 Baths
  • 20,211 Sq Ft

  Unlisted Address

  Rare 20-Property Rental Portfolio | Approximately 40 Parcels | Mountain Lodge ParkOffered for the first time in decades, this unique portfolio includes 20 rental properties across approximately 40 parcels, concentrated within the Mountain Lodge Park community.Investors can acquire decades of accumulated ownership and capital investment in a single transaction. Numerous properties

  

  Joseph Frullaney

  Serhant LLC

  Unlisted Address
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  /35

  $575,000

  $24K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,327 Sq Ft

  4 Ironworks Rd, Monroe, NY 10950

  Welcome to this spacious Colonial nestled on over half an acre in one of Monroe's established neighborhoods. Offering over 2,300 square feet of living space, this 4 bedroom, 2.5 bathroom home features a functional layout designed for everyday living and entertaining. The main level includes a bright living room, formal dining room, eat in kitchen, and an inviting family room with a fireplace.

  

  Kassandra Mott

  KW Hudson Valley United

  4 Ironworks Rd, Monroe, NY 10950
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  /30

  $750,000

  • 4 Beds
  • 3 Baths
  • 2,280 Sq Ft

  1 Sanford Ave, Chester, NY 10918

  Welcome to 1 Sanford Avenue, a beautifully designed 4-bedroom, 3-bath Bilonial offering over 2,200 square feet of thoughtfully finished living space in Chester. The inviting exterior features a welcoming entry, attached 2-car garage, and attractive curb appeal.Inside, the open-concept layout is enhanced by soaring high ceilings, hardwood floors throughout, and a tiled foyer. The spacious

  Danielle Hinton Redfin Real Estate

  1 Sanford Ave, Chester, NY 10918
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  /50

  $780,000

  • 4 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  17 Oldwyck Crescent, Highland Mills, NY 10930

  Check out the 3D walk through from the entire house on zillow you can find it by FACTS & FEATUES Virtual tour! 17 Oldwyck Cres - Original Owner Estate, Meticulously Maintained This is the one you’ve been waiting for. Loved since day one by its original owner, 17 Oldwyck Cres offers timeless quality, generous space, and thoughtful updates at every turn. Step InsideYou are greeted by a grand

  Yakov Winkler Preferred Properties Real Esta

  17 Oldwyck Crescent, Highland Mills, NY 10930
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  /35

  $919,000

  Open House 9/26 $60K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 4,044 Sq Ft

  5 Gleneagles Ct, Monroe, NY 10950

  Fully renovated 5-bedroom, 3.5-bath Colonial built in 2017 offering approximately 4,044 sq. ft. of living space on over half an acre. Features include a finished basement, fireplace, attached 2 car garage, solar panels that are paid off. average electric bill is $25.00 amazing saving for a home this size, spacious deck, beautiful in-ground pool, and a large private yard. A perfect blend of

  David Matos Premium Choice INC

  5 Gleneagles Ct, Monroe, NY 10950
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  /49

  $1,099,000

  $300K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,174 Sq Ft

  15 Arlington Dr, Monroe, NY 10950

  This exceptional residence offers an ideal blend of tranquility and luxury. Situated in a prime location, the property provides significant privacy on a generous, serene landscape. The expansive grounds are anchored by a pristine pool, serving as an idyllic retreat for refined outdoor leisure. The harmonious blend of vast outdoor space and unmatched tranquility defines this residence as an

  Joel Schwartz eRealty Advisors, Inc

  15 Arlington Dr, Monroe, NY 10950
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  /41

  $900,000

  • 5 Beds
  • 3.5 Baths
  • 2,956 Sq Ft

  32 Virginia Ave Unit 101, Monroe, NY 10950

  This 5-bedroom, 4-bath home in the beautiful village of South Blooming Grove offers a perfect blend of comfort, privacy, and modern luxury. Nestled in a prime location, it offers a serene lifestyle surrounded by green grass, trees, and fresh country air, all while being within walking distance to grocery stores and amenities. The main floor includes a large dining area with custom upgrades, a

  Joel Schwartz eRealty Advisors, Inc

  32 Virginia Ave Unit 101, 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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  /29

  $412,000

  Open Thu 4PM - 6PM

  • 3 Beds
  • 1 Bath
  • 1,288 Sq Ft

  21 Midway Dr, Monroe, NY 10950

  Built for easy, manageable living. Set on a corner lot, this 3-bed, 1-bath ranch has a welcoming presence from the moment you approach, complemented by an oversized driveway and front deck. Inside, the main living spaces feel open and connected while maintaining a sense of distinction, offering a comfortable layout with functionality in mind. A nicely-sized entrance foyer invites you in before

  Alyssa Woods Howard Hanna Rand Realty

  21 Midway Dr, Monroe, NY 10950
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  /25

  $649,000

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,863 Sq Ft

  289 Seven Springs Mountain Rd, Monroe, NY 10950

  Nestled on beautifully maintained grounds in a peaceful countryside setting, this charming home offers warmth, comfort, and timeless character. Situated on .59 of an acre, the property features inviting outdoor space perfect for relaxing or entertaining while enjoying the fresh country air. Inside a cozy fireplace creates the perfect ambiance, complemented by a warm and welcoming kitchen and

  Meyer Stoessel Keller Williams Hudson Valley

  289 Seven Springs Mountain Rd, Monroe, NY 10950
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  /37

  $1,175,000

  $100K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,400 Sq Ft

  556 Lakes Rd, Monroe, NY 10950

  Whether you're searching for a year-round residence or the perfect lakeside getaway, Walton Lake offers an exceptional opportunity. This spacious home features 4 bedrooms and 3 full bathrooms, blending comfort, charm, and functionality throughout.The beautifully designed kitchen is truly the heart of the home, showcasing rich mahogany cabinetry, elegant quartz countertops, and ample space for

  Ann Marie Hahr Keller Williams Realty

  556 Lakes Rd, Monroe, NY 10950
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  /25

  $450,000

  $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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  /32

  $1,199,000

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 5,712 Sq Ft

  16 Sunset Ridge, Monroe, NY 10950

  NEW PRICE! Ready to sell! Highly motivated seller. Sold as-is. Recent updates include fresh paint in select areas and new pavers for enhanced curb appeal. Located approximately one hour from NYC with convenient access to major roadways.Welcome to this secluded Colonial in desirable Trout Brook Estates, set on nearly 6 private acres with over 5,700 sq ft of living space. This spacious

  Carmela Lopez Borrazas Serhant LLC

  16 Sunset Ridge, 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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  /49

  $1,485,000

  $10K PRICE DROP

  • 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, .04 mile stroll to Kiryas Joel Gate. Shopping & conveniences. 200 yards from the Shul and Women's Yeshiva. 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

  Harry Donofrio Town and Village Real Estate

  421 Spring St, Monroe, NY 10950
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  /33

  $685,000

  $35K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,794 Sq Ft

  235 Sunset Terrace, Monroe, NY 10950

  If you’re searching for a truly exceptional, turn-key home in the Monroe area, look no further. This 2003 custom-built Colonial boasts nearly 3,000 square feet of immaculately maintained living space. Aside from its obvious curb appeal, this well-manicured home is in pristine condition throughout. Step inside to a two-story entrance foyer featuring a beautiful oak staircase, a stunning glass

  Vincent McAteer Terrie OConnor

  235 Sunset Terrace, Monroe, NY 10950
• 

  

  /23

  $824,900

  • 4 Beds
  • 3.5 Baths
  • 4,290 Sq Ft

  9 Roselawn Rd, Highland Mills, NY 10930

  Welcome to your “Private Country Club”! THE POOL and pool house are now open, but only for two more weeks! This gorgeous home is priced to sell! There is attention to detail and decorator touches throughout! First, you’ll enter the large, two-story foyer, which welcomes your guests with its soaring, vaulted ceiling, Palladium window, inlaid wood floor, and custom picture moldings! The lovely

  Joanne Cooper Howard Hanna Rand Realty

  9 Roselawn Rd, Highland Mills, NY 10930
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  /34

  $694,900

  $4K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,408 Sq Ft

  205 High St, Monroe, NY 10950

  Welcome to 205 High Street in the heart of Monroe, where timeless craftsmanship meets modern comfort in this truly one-of-a-kind Colonial located within the highly sought-after Monroe-Woodbury School District. Situated on a beautiful corner lot, this exceptional property offers a rare opportunity to purchase separately or together with the neighboring custom-built home at 23 Sweezy Place,

  Sandra Spector Howard Hanna Rand Realty

  205 High St, Monroe, NY 10950
• 

  

  /4

  $10,000

  $15K PRICE DROP

  • Land
  • 2,051 Sq Ft
  • $212,314 per Acre

  48 Paradise Trail, Mountain Lodge Park, NY 10950

  Vacant lot with adjacent parcel also available. Great opportunity for investment or future build.

  Michelle Levant Ellis Sotheby's Intl Realty

  48 Paradise Trail, Mountain Lodge Park, NY 10950
• 

  /2

  $749,000

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  4 Merriewold Ln S, Monroe, NY 10950

  Not your typical listing. There’s a presence here you don’t come across often the space, the flow, and the setting all line up. Ready to use today, with clear potential to take it further and unlock even more value. Whether you keep it as is or bring your own vision, this is the kind of property that can go in multiple strong directions. A standout opportunity with real upside. Feel free to send

  Moche Halpern Blooming Realty

  4 Merriewold Ln S, Monroe, NY 10950
• 

  

  /25

  $399,900

  $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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