Homes for Sale near North Main Street School

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  /36

  $839,000

  • 5 Beds
  • 4.5 Baths
  • 3,182 Sq Ft

  1 Cindy Ln, Highland Mills, NY 10930

  NEW!! Discover the epitome of luxury living in this magnificent, one-of-a-kind home!! Nestled in a highly sought-after neighborhood. This stunning property boasts an expansive layout, offering ample space for both relaxation and entertainment. The heart of the home is the magnificent kitchen, featuring elegant granite countertops that blend style and functionality, perfect for culinary

  Joseph Rosenfeld Flag Realty Group

  1 Cindy Ln, Highland Mills, NY 10930
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  /5

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,088 Sq Ft

  172 County Route 105, Highland Mills, NY 10930

  Discover an exceptional investment opportunity! Or make your dream of homeownership a reality with this charming property! Nestled in a prime location, this delightful house boasts an abundance of natural sunlight, creating a warm and inviting atmosphere throughout. Don't miss your chance to secure a bright future in a home that perfectly balances comfort and potential.

  Joseph Rosenfeld Flag Realty Group

  172 County Route 105, Highland Mills, NY 10930
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  /4

  $887,000

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

  5 Tappan Dr, Monroe, NY 10950

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

  Shalom Landau eRealty Advisors, Inc

  5 Tappan Dr, Monroe, NY 10950
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  /28

  $290,000

  • 2 Beds
  • 1 Bath
  • 896 Sq Ft

  1 Whippoorwill Trail, Monroe, NY 10950

  Quiet spot at the end of a short "trail"! You'll enjoy the spacious deck at the rear of the house for any get togethers or just a peaceful family BBQ & play area for the kids! There are 2 bedrooms & a small extra room, living room, & fireplace to enjoy in the winter! Both the kitchen and bathroom are updated. Don't miss out on this move in ready home! Parking is along the front of the lot.

  Kathy Dawson Howard Hanna Rand Realty

  1 Whippoorwill Trail, Monroe, NY 10950
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  /43

  $539,999

  • 4 Beds
  • 2 Baths
  • 1,758 Sq Ft

  10 Tulip Ln, Monroe, NY 10950

  Welcome to this meticulously maintained 4-bedroom, 2-bath raised ranch in a quiet and friendly neighborhood, ideally situated in the highly rated Monroe-Woodbury School District. With thoughtful updates, quality finishes, and a flexible floor plan, this home is ready for its next chapter.The main level features gleaming hardwood floors throughout the living room, dining room, and three

  Philip Szumlaski Keller Williams Realty

  10 Tulip Ln, Monroe, NY 10950
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  /46

  $559,000

  • 4 Beds
  • 2.5 Baths
  • 2,100 Sq Ft

  2 Fawn Ridge Ct, Harriman, NY 10926

  Welcome to this charming house located at 2 Fawn Ridge Court! This 2,100 sq ft home combines beauty and comfort. As you step inside, you’ll instantly fall in love with the spacious layout, which includes a cozy dining room, a large kitchen, four airy bedrooms, and three bathrooms. The large deck outside offers a stunning view of the landscape, making it perfect for outdoor entertaining. This

  David Kraus MK Realty Inc

  2 Fawn Ridge Ct, Harriman, NY 10926
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  /44

  $600,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  22 Ford Ct, Monroe, NY 10950

  Welcome to 22 Ford Court, Monroe – A Turn-Key Gem in Meadow Glen!Move right into this beautifully maintained 3-bedroom, 2.5-bathroom home, nestled on a quiet cul-de-sac within the desirable gated community of Meadow Glen. This property offers the perfect blend of style, modern upgrades, and peace of mind living.Step inside to find gleaming hardwood floors and a bright, open layout. The updated

  Amanda Rivera Sepulveda Keller Williams Realty

  22 Ford Ct, Monroe, NY 10950
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  /40

  $1,199,000

  • 6 Beds
  • 4.5 Baths
  • 4,240 Sq Ft

  219 Maple Ave, Monroe, NY 10950

  Nestled atop nearly 2 acres of park like property, this 6 Bedroom 4.5 Bath Masterpiece is the essence of luxury. Once inside the Entry Foyer, you’ll be greeted to an open floor plan of nearly 6,000 square feet. The Living Room & banquet sized Dining Room will impress the most discerning buyers with custom millwork. Gleaming hardwood floors throughout flow into an welcoming Great Room providing an

  Ryan Sunden Your Home Sold Guaranteed Rlty

  219 Maple Ave, Monroe, NY 10950
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  /42

  $999,000

  • 4 Beds
  • 2.5 Baths
  • 2,391 Sq Ft

  29 Virginia Ave, Monroe, NY 10950

  This thoughtfully cared-for Colonial sits in the heart of South Blooming Grove, surrounded by mature trees and lush landscaping that offer both privacy and curb appeal.A welcoming front deck leads into a spacious foyer, opening to a large living room, formal dining area, bright kitchen, and a cozy family room complete with a fireplace—perfect for gathering in every season.Upstairs features four

  Lazar Schvimmer Blooming Realty

  29 Virginia Ave, Monroe, NY 10950
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  /19

  $485,000

  • 3 Beds
  • 1.5 Baths
  • 1,244 Sq Ft

  5 James St, Harriman, NY 10926

  **Modern Updates, Open Layout & Prime Commuter Location – 5 James Street, Harriman, NY**Welcome to 5 James Street — a beautifully updated 3-bedroom, 1.5-bath home in the heart of Harriman, located within the highly rated Monroe-Woodbury School District.Enjoy a spacious **open-concept layout** that connects the kitchen, dining, and living areas — ideal for modern living and entertaining. The fully

  Kurt Lewis Weichert Realtors

  5 James St, Harriman, NY 10926
• 

  

  /19

  $859,000

  • 4 Beds
  • 2.5 Baths
  • 2,740 Sq Ft

  20 Tanyas Ct, Monroe, NY 10950

  "Ridge Top Knoll" is sited on a beautifully landscaped and improved lot with mature landscaping and mountain views. This four bedroom, two and a half bath home is 2740 square feet (not including basement square footage, currently used as a home gym) and has an open first floor plan. Entrance foyer with coat closet and built in is featured, as well as gorgeous living room with coffered ceiling and

  Susan Rost Tux Park Towne & Country

  20 Tanyas Ct, Monroe, NY 10950
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  /24

  $185,000

  • 2 Beds
  • 1 Bath
  • 588 Sq Ft

  9 Higgins Trail, Monroe, NY 10950

  Welcome to 9 Higgins Trail, 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, or both! The home also features two cozy bedrooms and a beautifully

  Nicholas Cuomo Keller Williams Realty

  9 Higgins Trail, Monroe, NY 10950
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  /27

  $439,000

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

  44 Hilltop Dr, Monroe, NY 10950

  Welcome to this amazing house — it has everything you've been looking for! Enjoy the outdoors with an above-ground pool connected to a 15-ft deck, perfect for summer fun and relaxation. Grow your vegetables and pick fresh fruit from your very own trees and plants! Inside, you'll find a brand-new kitchen with granite countertops tops updated hardwood flooring, ample living space, 2 well-sized

  Jacob Katz Exit Realty Venture

  44 Hilltop Dr, Monroe, NY 10950
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  /18

  $2,429,000

  • Land
  • 7 Acres
  • $350,505 per Acre

  56-58 Still Rd, Monroe, NY 10950

  Prime 6.93-Acre Development Opportunity in Monroe, NY – Orange County’s Largest Available SitePresenting a rare and exceptional opportunity to acquire a 6.93-acre development parcel in the heart of Monroe, NY — the largest available site in the area. Zoned SR-20, this expansive property offers a wide range of permitted residential and community uses, making it ideal for developers seeking

  Jon Cohen Skyline Real Estate Partners

  56-58 Still Rd, Monroe, NY 10950
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  /3

  $119,000

  • Land
  • 1.00 Acre
  • $119,000 per Acre

  0 St Georges Ave Unit KEY874110, Monroe Town, NY 10950

  Rare Opportunity! Lot ready to build + Potential to subdivide! This lot has road frontage to Sunset Terrace & St George Ave! Needs engineering for sewer approval. Great commuter location! Perfect fit for any Homeowner-to-be - Builder - Investor or anyone looking for a Great Buy!

  Nathen Singer MK Realty Inc

  0 St Georges Ave Unit KEY874110, Monroe Town, NY 10950
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  /37

  $585,000

  • 4 Beds
  • 2.5 Baths
  • 2,040 Sq Ft

  78 Pickerel Rd, Monroe, NY 10950

  Welcome to this charming Colonial set in the desirable Trout Brook ll subdivision of Monroe. This lovely home offers the perfect balance of privacy and convenience—just minutes to local shops and the village, and a short 10–15 minute drive to all major highways. Plus, you're only an hour from NYC, making it ideal for commuters or weekend getaways. Outdoor enthusiasts will love the close proximity

  Dylan Piazza Howard Hanna Rand Realty

  78 Pickerel Rd, Monroe, NY 10950
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  /43

  $474,900

  • 4 Beds
  • 2 Baths
  • 1,344 Sq Ft

  16 Robyn Dr, Monroe, NY 10950

  Welcome to this beautifully maintained Cape Cod-style home offering 4 spacious bedrooms and 2 full bathrooms, perfect for growing families or those seeking flexible living space. Step inside to find a warm and inviting layout with sun-filled rooms and hardwood floors. The main level features a bright living room, a kitchen with ample cabinetry and modern appliances. Two bedrooms and a full

  Bradford Lewis Keller Williams Realty

  16 Robyn Dr, Monroe, NY 10950
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  /35

  $649,900

  • 5 Beds
  • 4 Baths
  • 3,715 Sq Ft

  216 Maple Ave, Monroe, NY 10950

  A/O 6/30/2025 - Situated on a cul-de-sac street in the sought-after Round Lake community of Monroe, this 5BR/4BTH masterpiece is sure to impress the most discerning buyers. Upon entering the foyer you will be greeted to over 3,700 square feet of luxury space. The Formal Living Room is drenched in natural light flowing seamlessly into the banquet sized Dining Room. Next, imagine preparing your

  Ryan Sunden Your Home Sold Guaranteed Rlty

  216 Maple Ave, Monroe, NY 10950
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  /37

  $724,000

  • 4 Beds
  • 2.5 Baths
  • 3,977 Sq Ft

  278 Gibson Hill Rd, Chester, NY 10918

  AMAZING PROPERTY -- offers something for everyone! Gorgeously restored 3,977 square foot colonial farmhouse on 5.1 private acres, and with a pool, 5 bay carport, a 38x40 garage (with it's own entrance from road -- can rent out for income), and so much more! . . . Located in the Warwick Valley School District (and just a half mile to the Warwick town line). Just minutes to all downtown Warwick has

  Dean Diltz Keller Williams Realty

  278 Gibson Hill Rd, Chester, NY 10918
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  /13

  $339,000

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft

  107 Highland Ave, Monroe, NY 10950

  This cozy ranch is offering a great size living room, spacious kitchen with granite countertops, 2 bedrooms and a full bathroom. It has almost 0.5 acres with in ground pool and spacious level backyard. Minutes for all the shopping, Woodbury Outlets Mall, NYC buses and trains plus major highways.

  Anita S. Cristiano HomeSmart Homes & Estates

  107 Highland Ave, Monroe, NY 10950
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  /31

  $569,000

  • 5 Beds
  • 4 Baths
  • 2,504 Sq Ft

  19 Hilltop Place, Monroe, NY 10950

  This home is a true Mother daughter home and it can be legally rented as a two family property. Perfect for a big extended family that want to live next to each other or for investors who are looking for great rental income from the 2 units. The main level of this property consists of 4 bedrooms and 3 full baths. The kitchen has granite counter tops, stainless steel appliances and a large island

  Anita S. Cristiano HomeSmart Homes & Estates

  19 Hilltop Place, Monroe, NY 10950
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  /22

  $1,499,999

  • 4 Beds
  • 4 Baths
  • 7,308 Sq Ft

  37 Main St, Chester, NY 10918

  Prime Investment Opportunity in the Heart of Chester Village – 37-39 Main Street & 9 Bank StreetNestled in the charming and historic Village of Chester, this fully updated mixed-use property presents an exceptional investment opportunity. Originally built in 1935, this rustic yet modernized building seamlessly blends timeless character with contemporary upgrades.The property features:• Fully

  James Feldhaus eXp Realty

  37 Main St, Chester, NY 10918
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  /18

  $140,000

  • 3 Beds
  • 2 Baths
  • 980 Sq Ft

  9 Lily Ct, Woodbury, NY 10930

  Discover comfort and convenience in this well-maintained 3-bedroom, 2-bathroom +bonus room, mobile home with a fenced in rear yard. Located in the highly sought-after Monroe School District. This home offers a spacious and open layout, perfect for modern living. The primary suite features an en-suite bathroom for added privacy, while the additional bedrooms provide ample space for family, guests,

  Ivan Carvalho Exit Realty Connections

  9 Lily Ct, Woodbury, NY 10930
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  /27

  $219,000

  • 2 Beds
  • 1 Bath
  • 807 Sq Ft

  16 Arbor Trail, Monroe, NY 10950

  Do you dream of mountain living? Tucked among lush greenery, this 2-bed, 1-bath home offers one of the most private properties in Mountain Lodge Park with .73 of an acre of idyllic land and a second usable structure! The interior features a high ceiling in the living room, which can be overlooked by a loft off one of the bedrooms; a recently refreshed bathroom; and an enclosed porch to enjoy

  Alyssa Woods Howard Hanna Rand Realty

  16 Arbor Trail, Monroe, NY 10950
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  /48

  $875,000

  • 4 Beds
  • 3.5 Baths
  • 3,929 Sq Ft

  7 Gabriels Dr, Chester, NY 10918

  Don’t miss this opportunity to own a beautifully designed Colonial on 3.9 acres in a child-safe cul-de-sac, built with craftsmanship, comfort, and connection to nature in mind. Offering 3,929 sq ft of living space across 10 well-appointed rooms, this 4-bedroom, 3.5-bath home is very well maintained and features a spacious kitchen with granite countertops and stainless steel appliances—perfect for

  Chaim Weiss Exit Realty Venture

  7 Gabriels Dr, Chester, NY 10918
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  /10

  $220,000

  • 1 Bed
  • 1 Bath
  • 813 Sq Ft

  49 Tanager Rd Unit 4905, Monroe, NY 10950

  One bedroom top unit in mint condition. Large living room, oversized bedroom, kitchen and dining area full bath

  Joseph Morello Keller Williams Hudson Valley

  49 Tanager Rd Unit 4905, Monroe, NY 10950
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  /48

  $1,099,000

  • 4 Beds
  • 2.5 Baths
  • 2,722 Sq Ft

  5 Gabriels Dr, Chester, NY 10918

  Exquisite Colonial Estate: Timeless Grandeur Meets Modern LuxuryNestled gracefully on a private cul-de-sac amidst meticulously manicured grounds, this sprawling Colonial estate offers an unparalleled blend of classic elegance and contemporary comfort. From the moment you approach the stately wrought-iron fenced property and enter through the grand foyer, you are greeted by a magnificent staircase

  Beth Palma Keller Williams Realty

  5 Gabriels Dr, Chester, NY 10918
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  /47

  $629,999

  • 4 Beds
  • 2.5 Baths
  • 2,262 Sq Ft

  11 Catskill Ave, Monroe, NY 10950

  The original owners are retiring and want you to find the same happiness they did when they first came to this beautiful community located within the lake region of Monroe. This four bedroom colonial offers lots of space for the entire family. In addition to the living room, dining room and eat in kitchen on the first floor there is also a large bonus room that leads outside to a paver patio

  Theresa Budich Howard Hanna Rand Realty

  11 Catskill Ave, Monroe, NY 10950
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  /49

  $759,000

  • 5 Beds
  • 3.5 Baths
  • 2,462 Sq Ft

  8 Clinton Ct, Monroe, NY 10950

  Live the lakefront lifestyle in this beautifully renovated 5-bedroom, 3-bath home on a peaceful cul-de-sac in Monroe’s Pine Tree Beach community. Enjoy direct access to Pine Tree Lake for kayaking, fishing, and ice skating. The spacious interior features a chef’s kitchen with quartz countertops and lake views, formal dining with wet bar, and multiple living areas perfect for entertaining.

  Moses Zwiebel MS Realty Group USA, Inc

  8 Clinton Ct, Monroe, NY 10950
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  /33

  $799,000

  • Land
  • 15 Acres
  • $52,428 per Acre

  0 Rye Hill Rd Unit KEY866644, Monroe Town, NY 10950

  Beautiful piece of property with plenty of road frontage on Rye Hill Rd. to build a lovely home. Currently zoned RR-1.0AC. The owner does not have a survey and is unsure if the property can be subdivided. There are not any documents available for this lot. All offers will be considered, but no contingencies will be accepted. This property is being sold with two additional lots, both located at

  Lynda Hoss Weichert Realtors

  0 Rye Hill Rd Unit KEY866644, Monroe Town, NY 10950
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  /50

  $1,300,000

  • 4 Beds
  • 2.5 Baths
  • 3,955 Sq Ft

  90 Main St, Chester, NY 10918

  "The House on the Hill" Proudly offered for the first time in over 70 years. This expansive and character-rich home overlooks the heart of the village while offering nearly 10 acres of space, privacy, and endless potential. Set across three separate parcels totaling 9.68 acres, the property features a main house with approximately 4,000 sq ft, a charming 2-bedroom guest cottage, a large dairy

  STEVEN WROBEL JR. Serhant LLC

  90 Main St, Chester, NY 10918
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  /43

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft

  15 Prestwick Dr, Monroe, NY 10950

  PRESTWICK ESTATES! Prime location meets elegance and quality. this home has it all, Large rooms, open, spacious and bright. Beutiful kitchen, All granite counters, thick, solid oak floors, enough windows that allows natrual light to enter, full walkout basement,(unfinished) with many potential, amazing landscaping, A lot of PRIVACY ABOUND all around the property.Come see for yourself.

  Chaya Weiss Master Realty Group Inc.

  15 Prestwick Dr, Monroe, NY 10950
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  /35

  $1,700,000

  • 10 Beds
  • 6.5 Baths
  • 3,512 Sq Ft

  17 Bonnie Brook Rd, Monroe, NY 10950

  Over 20 sprawling acres with serene life, pond frontage, this is a true sanctuary. Located in Monroe-Woodbury this unique property offer two distinct residences and a spacious barn, providing endless possibilities. House 1: Contemporary Modern originally built in 1965. The first home boasts a generous 3,500+ sq ft of premium living space. Designed with a flexible layout, the home features two

  Pamela Henning Keller Williams Hudson Valley

  17 Bonnie Brook Rd, Monroe, NY 10950
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  /31

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,733 Sq Ft

  25 Laura Rd, Monroe, NY 10950

  You have to see this adorably renovated Monroe home with mother-daughter potential. The flexible layout is perfect for providing flexibility for multigenerational living or an additional source of rental income. The possibilities are endless! Upon entering the home, you'll be greeted by a well-lit living area that is perfect for all your gatherings or simply unwinding in the evening. The

  Dennis Clark Howard Hanna Rand Realty

  25 Laura Rd, Monroe, NY 10950
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  /21

  $799,000

  • 2 Beds
  • 2 Baths
  • 2,146 Sq Ft

  102 Cedar Cliff Rd, Monroe, NY 10950

  Beautifully crafted home with hardwood floors, stone fireplace, and original fixtures. Needs some TLC, but you’ll love it! The beautiful setting will steal your heart. There are 2 stone pillars that mark the driveway entrance, a wide step leading into a covered front porch surrounded by amazing mature trees and shrubs, and a newer roof. This home has a comfortable and private country-like

  Lynda Hoss Weichert Realtors

  102 Cedar Cliff Rd, Monroe, NY 10950
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  /35

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,484 Sq Ft

  576 Bull Mill Rd, Chester, NY 10918

  A fantastic opportunity for investors or future homeowners! This well-maintained 3-bedroom, 2-bath home is set on a large, flat lot in a quiet, nature-filled neighborhood and offers strong rental potential with long-term flexibility. Inside, you’ll find a spacious living room, formal dining area, kitchen, and comfortable layout ideal for everyday living. Recent updates include fresh interior

  Lazar Schvimmer Blooming Realty

  576 Bull Mill Rd, Chester, NY 10918
• 

  

  /31

  $669,900

  • 4 Beds
  • 3.5 Baths
  • 3,092 Sq Ft

  36 Pinehurst Cir, Monroe, NY 10950

  Mansion Ridge is located in one of the region's most scenic and dramatic areas...this "Morningside" model overlooks the 6th hole on a world class Jack Nicklaus Signature Golf Course. Premier location within the complex with golf and mountain views. This home has been totally redone and is like brand new. Just place your furniture and make this home yours. Beautifully appointed and shows to

  Meryl Bernstein Weichert Realtors

  36 Pinehurst Cir, Monroe, NY 10950
• 

  

  /23

  $1,350,000

  • 6 Beds
  • 5.5 Baths
  • 4,171 Sq Ft

  18 Pullman Route, Monroe, NY 10950

  Unparalleled Future Luxury in Woodbury Junction.Welcome to your future dream home in the prestigious Woodbury Junction! This to-be-built, almost 4000 sq ft colonial-style residence offers wall-to-wall quality and top-notch finishes. Upon completion, you will be greeted by a grand foyer leading to an elegant dining room that is open to a spacious living room. Imagine an expansive kitchen

  Joel Jeremias eRealty Advisors, Inc

  18 Pullman Route, Monroe, NY 10950
• 

  

  /42

  $999,000

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

  180-184 Pine Tree Rd, Monroe, NY 10950

  Discover an exceptional opportunity at 180-184 Pine Tree Road! This property features two houses on a single lot, making it ideal for living renovated house at 180 Pine Tree Rd, and collecting rent from the next house at 184 Pine Tree Rd, or it can be bought for a great investment! Upon entering the first house at 180 Pine Tree, you'll be greeted by a nicely renovated house in mid-2022 and a

  David Kraus MK Realty Inc

  180-184 Pine Tree Rd, Monroe, NY 10950
• 

  

  /35

  $499,000

  • 4 Beds
  • 2 Baths
  • 2,367 Sq Ft

  279 Mountain Lodge Rd, Monroe, NY 10950

  Step into style and comfort with this renovated gem—just 3 years young and packed with upgrades! This spacious home features 4 generous bedrooms, a warm and inviting kitchen with rich hickory cabinets, and gleaming oak floors that extend into the dining area. Enjoy seamless indoor-outdoor living with two expansive decks—front and back—and a flat, private backyard perfect for relaxing or

  Lazar Schvimmer Blooming Realty

  279 Mountain Lodge Rd, Monroe, NY 10950

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