Homes for Sale near Monroe-Woodbury Middle School

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  /31

  $1,199,900

  • 4 Beds
  • 5 Baths
  • 4,624 Sq Ft

  16 Lori Ln, Chester, NY 10918

  Indulge in luxury living at this resort-style residence in Chester, NY, within the prestigious Monroe Woodbury School District. Set on a tranquil cul-de-sac, this home graces one of MW Schools' most beautiful streets. Crafted with precision by Paul Janus Building Arts, custom millwork, arched windows, and detailed moldings evoke the charm of Westchester and Bergen County homes. From the

  

  Randolph Rogers

  eXp Realty

  (845) 681-2264

  16 Lori Ln, Chester, NY 10918
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  Explore Monroe-Woodbury Middle School

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  /27

  $499,000

  • 4 Beds
  • 4 Baths
  • 2,800 Sq Ft

  4 Linden Dr, Highland Mills, NY 10930

  Welcome to this rare 4-bedroom, 4-bathroom townhome in the sought-after Timber Ridge community of Woodbury, NY—offering many updates, and a versatile location! This spacious multi-level home features a brand new roof (installed June 2025) and an open-concept main level with vaulted ceilings, skylights, and sun-drenched interiors. The oversized kitchen flows into the dining area, which opens to a

  

  Erin Connolly

  Artisan Realty

  (845) 393-6635

  4 Linden Dr, Highland Mills, NY 10930
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  /32

  $489,999

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

  93 Weygant Hill, Highland Mills, NY 10930

  Move-in ready with recent updates! Start your day with expansive, picturesque views of the valley, stretching as far as the eye can see. This delightful 3-bedroom, 2-bath home features a first-floor primary suite, an additional bedroom and full bath on the main level, and a spacious upper-level bedroom that offers privacy and versatility.Step outside to your backyard retreat, which backs up to

  

  Kristen Velez

  RE/MAX Benchmark Realty Group

  (845) 412-8180

  93 Weygant Hill, Highland Mills, NY 10930
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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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  /2

  $68,800

  • Land
  • 1.00 Acre
  • $68,800 per Acre

  0 Margaret Rd Unit KEY862335, Monroe Town, NY 10950

  Close to transportation, shopping, and dining. Residential Lot. Need variance.

  

  John Olivero

  Keller Williams Realty

  (845) 373-3537

  0 Margaret Rd Unit KEY862335, Monroe Town, NY 10950
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  /37

  $445,000

  • 4 Beds
  • 2 Baths

  34 Round Lake, Monroe, NJ 10950

  

  Franklyn Crowe

  WEICHERT REALTORS

  (845) 606-6760

  

  34 Round Lake, Monroe, NJ 10950
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  /49

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 1,560 Sq Ft

  63 Fawn Hill Rd, Tuxedo Park, NY 10987

  Welcome to your private haven in the heart of the Laurel Ridge community, nestled amid the scenic landscapes of Tuxedo Park, NY. Surrounded by nature and tucked into a peaceful, well-established neighborhood with no HOA, this beautifully updated 3-bedroom, 2.5 bath ranch-style home blends high-end interior updates with stunning outdoor living and seasonal mountain views—just 40 miles from NYC.

  

  Christina Rowan

  Howard Hanna Rand Realty

  (845) 684-9899

  63 Fawn Hill Rd, Tuxedo Park, NY 10987
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  /49

  $475,000

  • 2 Beds
  • 4 Baths
  • 1,777 Sq Ft

  14 Hidden Creek Blvd, Monroe, NY 10950

  Look No Further... Your Ideal End Unit Townhome Awaits!Welcome to this beautifully maintained 2-bedroom END unit townhome in the Hidden Creek community. Move-in ready and filled with natural light, this tri-level residence offers comfort, convenience, and a versatile layout that adapts to your lifestyle.Step inside to find a spacious eat-in kitchen with sliders that open to a

  

  Jennifer DiCostanzo

  RE/MAX Town & Country

  (845) 328-4387

  14 Hidden Creek Blvd, Monroe, NY 10950
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  /29

  $564,000

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  391 Bull Mill Rd, Chester, NY 10918

  Welcome home to this storybook setting, where a majestic weeping cherry blossom greets you with it's graceful cascade of blossoms each spring. This beautifully preserved historical farmhouse set on 1.7 acres along a scenic country road just down the lane from a local farm where the soft "mooing" adds to the peaceful rural charm. Sitting pretty on a corner lot with a circular driveway, this home

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
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  /38

  $445,000

  • 4 Beds
  • 2 Baths
  • 1,356 Sq Ft

  34 Round Lake Ave, Monroe, NY 10950

  Your Retreat Awaits in the Exclusive Round Lake Community!Discover the perfect blend of comfort, charm, and potential in this inviting 4-bedroom, 2-bathroom home nestled in one of the area's most sought-after private lake communities. With exclusive access to a members-only lake, you’ll enjoy tranquil mornings, peaceful paddleboarding, or weekend escapes just steps from your

  

  Franklyn Crowe

  Weichert Realtors

  (845) 273-3305

  34 Round Lake Ave, Monroe, NY 10950
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  /48

  $579,000

  • 4 Beds
  • 3 Baths
  • 2,774 Sq Ft

  10 Sunset Heights, Monroe, NY 10950

  Welcome to this beautifully maintained Custom Cape Cod located in the heart of the Village! Thoughtfully designed for modern living, this move-in-ready home features a spacious bedroom and full bath on the main floor—perfect for guests, extended family, or convenient one-level living.The kitchen and bathrooms were masterfully designed by Masterworks, featuring high-end finishes

  Peter Sisca Real Broker NY LLC

  10 Sunset Heights, Monroe, NY 10950
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  /29

  $369,000

  • 3 Beds
  • 2.5 Baths
  • 1,585 Sq Ft

  252 Heritage Ln, Monroe, NY 10950

  Welcome to this beautifully maintained 3 bedroom, 2.5-bath townhouse located in a highly sought after community within the Monroe-Woodbury School District. This move-in ready home features an open-concept main level with a spacious living room and kitchen area, perfect for entertaining. Enjoy the convenience of private in-unit laundry and assigned parking, with plenty of additional parking

  Brenda Wiley Howard Hanna Rand Realty

  252 Heritage Ln, Monroe, NY 10950
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  /50

  $995,000

  • 4 Beds
  • 3 Baths
  • 2,700 Sq Ft

  893 Laroe Rd, Monroe, NY 10950

  When you walk in the front door, the artful design and carefully curated surroundings immediately banish the outside world. The open floor plan and copious windows bring in the sunshine and natural light. Begin in the spacious living room with woodburning fireplace that opens into the family room. The living room flows naturally to the family room with its own fireplace, and it is surrounded by

  Lisa Fountain Corcoran Country Living

  893 Laroe Rd, Monroe, NY 10950
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  /45

  $999,000

  • 2 Beds
  • 2 Baths
  • 2,073 Sq Ft

  25 Union Transfer, Monroe, NY 10950

  Welcome to your golden age in a wonderful, brand-new home set in a gated community, surrounded by breathtaking scenic mountain views! Step inside to this single-floor ranch with boasting 10 Ft ceilings, hardwood floor, and high-end finishes. Complete with many upgrades such as rough plumbing for a second kitchen, granite countertops and vanities, huge walk-in closet, and expansive deck. Nestled

  Dovid Hoffman MK Realty Inc

  25 Union Transfer, Monroe, NY 10950
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  /50

  $849,900

  • 5 Beds
  • 3 Baths
  • 3,485 Sq Ft

  284 Bull Mill Rd, Chester, NY 10918

  Monroe's Stunning Mini Mansion Awaits Its New Owner!This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase.Before heading upstairs, prepare to be impressed by the spacious chef's

  Jayne Mangieri Keller Williams Valley Realty

  284 Bull Mill Rd, Chester, NY 10918
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  /33

  $349,000

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

  9 Heritage Dr Unit B, Harriman, NY 10926

  Welcome to the Harriman Hill Community! This move-in ready 3-bedroom, 1 full and half bathroom townhome offers comfortable living in a highly convenient location. The main level features a spacious living and dining area with wood flooring, sliding glass doors open to a cozy porch area, powder room, and an updated kitchen with stainless steel appliances. Freshly painted throughout! The upper

  Nicole Isaacs Century 21 Full Service Realty

  9 Heritage Dr Unit B, Harriman, NY 10926
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  /39

  $799,900

  • 3 Beds
  • 2.5 Baths
  • 2,969 Sq Ft

  4 Ainsley Ct, Highland Mills, NY 10930

  BRIGADOON ESTATES!! MINT CONDITION! IT'S A BEAUTY!! Open Floor Plan! 3 Bedrooms! 2 1/2 Bathrooms! 2 Car Garage! Eat in Kitchen with Granite Counter Tops, New Stainless Steel Appliances & Breakfast Nook! Dramatic Two Story Living Room with Gas Fireplace! Master Bedroom Suite with Two Walk In Closets & Tray Ceilings! Dining Room! Family Room! Jack & Jill Bathroom! Grand Foyer! Full Walk Out

  Amanda Dnistrian ARC Realty 1 in Sales

  4 Ainsley Ct, Highland Mills, NY 10930
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  /21

  $789,000

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

  65 Hawxhurst Rd, Monroe, NY 10950

  Discover your dream home with this stunning property that perfectly blends modern elegance and comfort. This beautifully designed house boasts a fresh, contemporary interior that invites you to experience luxury living at its finest. With spacious rooms flooded with natural light, you'll enjoy an open layout that is perfect for both entertaining and everyday family life. The expansive lot offers

  Joseph Rosenfeld Flag Realty Group

  65 Hawxhurst Rd, Monroe, NY 10950
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  /37

  $675,000

  • 5 Beds
  • 3 Baths
  • 2,983 Sq Ft

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a peaceful cul-de-sac, this lovingly maintained 5-bedroom, 3-full-bath home offers 3,000 square feet of light-filled living space and a layout designed for comfort and flexibility. Owned by the original homeowner since day one, this property has been thoughtfully cared for and is ready for its next chapter.Inside, you’ll find big, bright rooms and an easy flow perfect for

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
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  /49

  $945,000

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

  9 Roselawn Rd, Highland Mills, NY 10930

  Luxury Awaits AT AN UNBELIEVABLE PRICE! Almost totally redone in the past seven years. Open all of your back sliding doors to...Your own private "Country Club"!!! Exquisite heated 20 x 40’ pool with fiberglass coating ( no vinyl liner), and "Sunshelf", surrounded by an oversized deck of beautiful pavers, AND a POOL HOUSE with kitchenette, 1/2 bath, and sitting room! Tall trees line the back of

  Joanne Cooper Hudson Heritage Realty

  9 Roselawn Rd, Highland Mills, NY 10930
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  /47

  $649,000

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  229 Orchard Dr, Monroe, NY 10950

  Step into luxury with this fully renovated 4-bedroom, 3-bathroom home, transformed in 2023 with the finest finishes and attention to detail. The expansive living room invites you to relax by the natural gas fireplace, creating a cozy yet elegant atmosphere. The chef's kitchen is a dream, featuring sleek stainless steel appliances, stunning granite countertops, and custom cabinetry, seamlessly

  Moche Halpern Blooming Realty

  229 Orchard Dr, Monroe, NY 10950
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  /48

  $665,000

  • 4 Beds
  • 2.5 Baths
  • 2,229 Sq Ft

  61 Peter Bush Dr, Monroe, NY 10950

  Well-Maintained & Beautifully Updated 4-Bedroom Split-Level Home!Welcome to this spacious and thoughtfully updated 4-bedroom, 2.5-bath split-level home that offers the perfect blend of comfort, style, and functionality. From the moment you arrive, you’ll notice the pride of ownership throughout.Inside, you’ll find gleaming hardwood floors, a beautifully updated kitchen with modern

  Patricia Hyer Howard Hanna Rand Realty

  61 Peter Bush Dr, Monroe, NY 10950
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  /46

  $679,000

  • 4 Beds
  • 2.5 Baths
  • 2,278 Sq Ft

  11 Whitman Place, Monroe, NY 10950

  Welcome to 11 Whitman Place, an exquisite property that perfectly balances comfort and style. Spanning an impressive 2,278 square feet, this home features a thoughtfully designed layout with 8 spacious rooms, making it ideal for everyday living. As you step inside, you’ll be greeted by a bright and inviting atmosphere. The heart of the home is a beautiful kitchen that seamlessly flows into the

  David Kraus MK Realty Inc

  11 Whitman Place, Monroe, NY 10950
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  /50

  $620,000

  • 4 Beds
  • 2 Baths
  • 3,330 Sq Ft

  114 Old Mansion Rd, Chester, NY 10918

  Charming Colonial with 4 Bedrooms on Nearly an Acre – Prime Location!Welcome to this beautifully maintained Colonial-style home nestled on a generous 0.92-acre lot, offering space, comfort, and convenience. This freshly painted home features 4 spacious bedrooms, 2 full bathrooms, and a versatile layout perfect for modern living.The first floor boasts gleaming hardwood floors, a

  Hershel Lowy Master Realty Group Inc.

  114 Old Mansion Rd, Chester, NY 10918
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  /42

  $615,000

  • 5 Beds
  • 3 Baths
  • 2,948 Sq Ft

  152 Fawn Hill Rd, Tuxedo Park, NY 10987

  TUXEDO! – Mid-Century Scenic Country Retreat--Nestled among the trees in the sought-after Laurel Ridge community, this custom home blends rustic charm with contemporary design. Featuring 5 bedrooms and 3 full baths, it offers a spacious, open floor plan perfect for both entertaining and embracing the tranquility of nature. At the heart of the home lies a stunning living room, where SOARING

  Mary Ann Mitchell eXp Realty

  152 Fawn Hill Rd, Tuxedo Park, NY 10987
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  /27

  $699,000

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft

  284 W Mombasha Rd, Monroe, NY 10950

  Welcome to your dream home! Nestled on 5.4 acres of serene privacy, this meticulously renovated colonial blends timeless charm with modern luxury. Tons of natural sunlight throughout the home. Step inside to gleaming hardwood floors throughout both levels and a spacious open-concept layout perfect for today’s lifestyle. The heart of the home is a bright and airy kitchen, formal dining room and

  Jaime Dicembri Century 21 Full Service Realty

  284 W Mombasha Rd, Monroe, NY 10950
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  /21

  $735,000

  • 4 Beds
  • 2.5 Baths
  • 2,566 Sq Ft

  3 Moorefield Cir, Highland Mills, NY 10930

  Welcome to the highly desirable Brigadoon community, ideally situated on a quiet cul-de-sac! This elegant colonial home offers 4 spacious bedrooms and 2.5 bathrooms, along with a 2-car garage. The sunlit eat-in kitchen is a chef’s dream, featuring granite countertops, a center island, ceramic tile flooring, and a convenient butler’s pantry—perfect for entertaining. The expansive primary suite

  Jacob Fried Keller Williams Realty

  3 Moorefield Cir, Highland Mills, NY 10930
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  /33

  $670,000

  • 4 Beds
  • 2.5 Baths
  • 2,960 Sq Ft

  38 Buena Vista Terrace, Central Valley, NY 10917

  Short walk to the Woodbury community pool !!!This charming residence offers 4 bedrooms and 3 bathrooms, encompassing 2,960 square feet of living space on a one-acre lot. Spacious kitchen featuring granite countertops and oak cabinetry. Living Areas: Hardwood floors throughout; family room with a fireplace and French doors leading to a 1000 SQ FT deck. Parking:

  Hermann Kabore Exit Realty Group

  38 Buena Vista Terrace, Central Valley, NY 10917
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  /18

  $629,000

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

  162 Fawn Hill Rd, Tuxedo Park, NY 10987

  Rare Mid-Century Modern Gem in Tuxedo, NY – Just 1 Hour from NYCStep back in time with this beautifully preserved 1968 Mid-Century home, offering 4 spacious bedrooms, 2.5 baths, and set on a private and scenic .57-acre lot. Filled with original architectural details, including the vintage kitchen and classic design elements, this home is a rare find for lovers of authentic mid-century style.Enjoy

  Laura Denberg Tuxedo Hudson Realty Corp

  162 Fawn Hill Rd, Tuxedo Park, NY 10987
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  /49

  $629,999

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

  11 Catskill Ave, Monroe, NY 10950

  Brand new oversized driveway. Parking for 6-8 cars easily plus a two car garage. This beautiful 4 bedroom, plus first floor private study is located in a community of well kept homes within the lake region of Monroe. You can swim, fish and use a non motorized boat all season long. This is a large home perfect for family and friend gatherings. . In addition to the living room, dining room and

  Theresa Budich Howard Hanna Rand Realty

  11 Catskill Ave, Monroe, NY 10950
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  /46

  $650,000

  • 7 Beds
  • 3 Baths
  • 2,504 Sq Ft

  117 Woodland Rd, Highland Mills, NY 10930

  This colonial style Mother-daughter home has plenty of room for everyone! Large 7-bedroom home with legal accessory apartment in desirable Woodbury has many recent updates. The main level was re-done in 2024. Enter from the covered front entry into the living room which has new LVP flooring that extends into the kitchen and hall. The main level bedroom has an ensuite bath with beautifully tiled

  Karin Poggio HomeSmart Homes & Estates

  117 Woodland Rd, Highland Mills, NY 10930
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  /39

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,959 Sq Ft

  55 Midland Ave, Central Valley, NY 10917

  Welcome Home! This beautifully expanded, and meticulously maintained home is wrapped in elegance and warmth. Nestled on a serene half acre lot, this property combines classic charm with high end modern updates that are perfect for today's lifestyle. After a significant addition in 2014, that added a primary suite with vaulted ceilings, luxurious full bath with soaking tub and double walk in

  Debbie Goldstein Howard Hanna Rand Realty

  55 Midland Ave, Central Valley, NY 10917
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  /24

  $695,000

  • 3 Beds
  • 2.5 Baths
  • 2,402 Sq Ft

  4 Mack Place, Monroe, NY 10950

  Discover this charming colonial home in the heart of Monroe, perfectly located and full of warmth and comfort. Step inside to find hardwood floors, vaulted ceilings, and a cozy wood-burning fireplace—ideal for family time and entertaining. The spacious kitchen with lots of cabinets, formal dining room, and family areas open to a large deck, perfect for summer BBQs and relaxing in a private

  Shayndel Moore Keller Williams Hudson Valley

  4 Mack Place, Monroe, NY 10950
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  /48

  $694,900

  • 4 Beds
  • 1.5 Baths
  • 2,220 Sq Ft

  33 Winchester Dr, Monroe, NY 10950

  Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room.

  Dennis Clark Howard Hanna Rand Realty

  33 Winchester Dr, Monroe, NY 10950
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  /27

  $639,000

  • 4 Beds
  • 3 Baths
  • 2,048 Sq Ft

  71 Fawn Hill Rd, Tuxedo Park, NY 10987

  Motivated sellers and reduction of price from $680,000 to $639,000! Exquisitely updated 4 bedroom, 3 bathroom ranch in prestigious Laurel Ridge development in Tuxedo, NY. This residence provides a private, serene retreat while maintaining convenient train and bus access to metropolitan amenities. A newer gourmet kitchen (2022) features contemporary finishes and premium appliances. The kitchen and

  Jodi Caliciotti Terrie OConnor

  71 Fawn Hill Rd, Tuxedo Park, NY 10987
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  /50

  $649,900

  • 4 Beds
  • 2.5 Baths
  • 2,290 Sq Ft

  11 Mountain Park Rd, Monroe, NY 10950

  This well maintained colonial has a unique and open floor plan that also maximizes living space. The impressive mahogany front door will give you a good indication of what awaits you when you enter the home. The entire house including all the bedrooms have hardwood oak floors and the entry and baths are tiled. The first floor has crown and box moulding accents. The Kraftmaid cabinetry is

  Theresa Budich Howard Hanna Rand Realty

  11 Mountain Park Rd, Monroe, NY 10950
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  /18

  $620,000

  • 5 Beds
  • 2 Baths
  • 2,298 Sq Ft

  129 Franklin Ave, Monroe, NY 10950

  Opportunity & LOCATION! Renovated colonial style home in the Village of Monroe NY. All rooms are spacious and sunny, with all Municipal services, plenty of space to entertain, near all Conveniences, Public Transportation, Major Highways, and Shopping malls, here is so much more in this wonderful neighborhood, Just Waiting for You.

  Eliezer Safdie Sage Realty Center LLC

  129 Franklin Ave, Monroe, NY 10950
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  /50

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,555 Sq Ft

  165 Fawn Hill Rd, Tuxedo Park, NY 10987

  Set high on a peaceful acre with a stunning mountain backdrop, this fully remodeled contemporary in Tuxedo is your everyday escape. With over 2,500 sq ft of beautifully designed living space, the home blends modern updates with the warmth of nature and total privacy.Soaring ceilings, rich hardwood floors, and oversized windows let the light pour in across the open-concept main level. The

  Jon Paul Molfetta Keller Williams Valley Realty

  165 Fawn Hill Rd, Tuxedo Park, NY 10987
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  /34

  $550,000

  • 3 Beds
  • 3 Baths
  • 1,940 Sq Ft

  28 Catskill Ave, Monroe, NY 10950

  Welcome to your upgraded sanctuary—this fully renovated country colonial sits proudly on a half-acre with a freshly reimagined in-ground pool, three designer-grade full bathrooms, and exclusive deeded access to Walton Lake just down the road.Curb appeal? Locked in. With brand-new vinyl siding, updated windows and doors, a full fencing package, custom paver walkways, and pro landscaping,

  Richard Frierson Hollingsworth Real Estate Grp.

  28 Catskill Ave, Monroe, NY 10950
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  /4

  $250,000

  • 4 Beds
  • 2 Baths
  • 1,756 Sq Ft

  24 Summit Ave, Harriman, NY 10926

  CALLING ALL INVESTORS! LOCATION, LOCATION, LOCATION. Investment Property in Desirable Harriman Neighborhood, Monroe-Woodbury School District. This is a STRICTLY AS-IS Estate Sale. Four car garage. House was condemned due to a fire. Full Rehab or tear down required to gain certificate of occupancy. Perched in a prestigious established neighborhood minutes to Interstates, shopping, Woodbury

  Brenda Guttenberg RE/MAX Benchmark Realty Group

  24 Summit Ave, Harriman, NY 10926

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