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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  /29

  $550,000

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

  391 Bull Mill Rd, Chester, NY 10918

  Motivated Seller!! 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

  

  Alexandra Zinko

  Century 21 Realty Center

  (845) 412-9860

  391 Bull Mill Rd, Chester, NY 10918
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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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  /36

  $599,000

  • 3 Beds
  • 3 Baths
  • 2,198 Sq Ft

  10 Karen Dr, Monroe, NY 10950

  Unique layout with a modern flare! 10 Karen Dr. Monroe, NY is the perfect home for a multigenerational set up! This 3/4 bedroom 3 bath home is in PRIME condition offering improvements galore! Brand new European Style custom kitchen ( too much to list) New Sliders lead to a huge composite deck with built in benches and island with granite countertops! Large Master en-suite with huge closets

  

  Erin Connolly

  Artisan Realty

  (329) 217-0507

  10 Karen 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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  /23

  $629,900

  • 3 Beds
  • 3 Baths
  • 2,226 Sq Ft

  6 Autumn Ln, Monroe, NY 10950

  Welcome to 6 Autumn Lane, a charming Monroe retreat set on 2.3 private acres surrounded by nature. This inviting home offers 3 spacious bedrooms and 3 full bathrooms, along with a large open living room ideal for gatherings. The beautifully updated kitchen features granite countertops, a Sub-Zero refrigerator, and a cozy eat-in area with views of the scenic outdoors. Enjoy the peaceful setting

  

  Haakim Byrd

  HomeSmart Homes & Estates

  (329) 219-0350

  6 Autumn Ln, Monroe, NY 10950
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  /42

  $575,000

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft

  12 Juniper Ln, Monroe, NY 10950

  Welcome to this 4-bedroom, 3 full bath raised ranch offering a flexible and spacious layout designed for comfortable everyday living. Hardwood floors run throughout the main level, adding warmth and character to the home's living spaces. The primary bedroom features a private en-suite bath, creating a quiet and comfortable retreat. Three additional bedrooms provide plenty of room for family,

  

  Shaylene Neumann

  Houlihan Lawrence Inc.

  (329) 208-1641

  12 Juniper Ln, Monroe, NY 10950
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  /27

  $469,999

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

  4 Linden Dr, Highland Mills, NY 10930

  Priced to MOVE.....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

  

  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

  

  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 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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  /50

  $979,000

  • 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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  /29

  $549,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,865 Sq Ft

  12 Case Ct, Monroe, NY 10950

  Beautifully maintained home offering comfort, space, and modern updates throughout. Features three separate zones for heating and air conditioning. The fully finished walk-out lower level provides additional living space, access to a private patio, and a wooded backdrop for added privacy. Enjoy updated laminate flooring on the lower level, newer carpeting throughout (approx. 3 years old), and

  Donna Gray Redfin Real Estate

  12 Case Ct, Monroe, NY 10950
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  /43

  $649,999 Open Sun 11AM - 3PM

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

  106 Maple Ave, Monroe, NY 10950

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  Vincent McAteer Terrie OConnor

  106 Maple Ave, Monroe, NY 10950
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  /48

  $724,999 Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 2,796 Sq Ft

  420 Rye Hill Rd, Monroe, NY 10950

  MONROE-WOODBURY SCHOOLS!!! Welcome to this beautifully maintained 4-bedroom, 2.5-bath Contemporary Colonial, perfectly situated in the highly desirable Town of Monroe and within the award-winning Monroe-Woodbury School District. This home is just minutes from the Village of Monroe, offering local restaurants, shopping plazas, and scenic parks. With convenient access to Route 17M, Route 6,

  Richard Baxter Keller Williams Realty

  420 Rye Hill Rd, Monroe, NY 10950
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  /47

  $649,000 Open House 9/27

  • 5 Beds
  • 2 Baths
  • 2,368 Sq Ft

  52 Woodland Rd, Highland Mills, NY 10930

  Wow! This enlarged Highland Mills raised ranch boasts 5 bedrooms and two full baths situated on a corner lot next to designated Town green space. Its grassy front, back and side yards contain mature trees and perennial plants that create a serene, relaxing environment. Inside the home is a lovely living room with a newer Anderson bow window that lets in tons of afternoon light. There is

  Derek Greene Greene Realty Group

  52 Woodland Rd, Highland Mills, NY 10930
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  /49

  $850,000

  • 4 Beds
  • 3 Baths
  • 3,479 Sq Ft

  9 Prestwick Dr, Monroe, NY 10950

  Welcome to 9 Prestwick Dr – a home that truly stands out. As you approach, the charming covered front porch offers a warm welcome, setting the stage for what lies inside. Step through the front door into a grand two-story entrance that immediately captures attention. The spacious formal living room is perfect for entertaining, while the elegant dining room, with its gleaming hardwood floors,

  Richard Froehlich RE/MAX Benchmark Realty Group

  9 Prestwick Dr, Monroe, NY 10950
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  /49

  $850,000

  • 2 Beds
  • 2 Baths
  • 2,150 Sq Ft

  37 Southfield Falls, 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

  37 Southfield Falls, Monroe, NY 10950
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  /35

  $869,000

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

  46 Woodland Rd, Monroe, NY 10950

  Discover the perfect blend of luxury, comfort, and entertainment in this stunning contemporary home, elegantly renovated and designed by its owner, a professional interior designer. This home offers a serene escape surrounded by lush trees.A pergola entrance welcomes you into a grand foyer, leading to an open-concept living space bathed in natural light, thanks to three expansive sliding

  Alejandra Fermin Empire Fine Homes

  46 Woodland Rd, Monroe, NY 10950
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  /49

  $989,900 Open Sat 12PM - 2PM

  • 4 Beds
  • 4.5 Baths
  • 3,523 Sq Ft

  36 Deangelis Dr, Monroe, NY 10950

  Come fall in love with this luxurious Lennar Built house, nestled in the prestigious Estates of Briarcliff, and make it your forever home! Upon entering, you will be warmly greeted by hardwood floors, and a dramatic two story foyer. The dual staircase adds a touch of elegance, while the oversized windows flood the interior with natural light. To the right of the entry way, you will find a formal

  Chris Scibelli Keller Williams Realty

  36 Deangelis Dr, Monroe, NY 10950
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  /27

  $799,000

  • 4 Beds
  • 3 Baths
  • 1,716 Sq Ft

  23 Rabbit Hill Rd, Monroe, NY 10950

  Calling all Investors 3.4 acres of private propertyMain house two bedrooms two baths Cottage one bedroom one bath Plenty of storage areasSOLD AS IS !

  Rosemarie Franzese Howard Hanna Rand Realty

  23 Rabbit Hill Rd, Monroe, NY 10950
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  /13

  $679,888

  • 4 Beds
  • 3 Baths
  • 2,456 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, F 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 LOMBARDO HOMES & ESTATES

  1 Grant Ct, Highland Mills, NY 10930
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  /45

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 1,817 Sq Ft

  23 Eagle St, Monroe, NY 10950

  This beautifully upgraded Cape-style home in the top-rated Monroe-Woodbury School District features 3 bedrooms and 2 full baths with modern comfort and style. The primary suite boasts a walk-in closet and custom shower, while upstairs laundry, wide plank floors, and a cozy fireplace add convenience and charm. The 16x20 chef's kitchen includes a commercial oven, modern appliances, and a 4x8

  Patricia Culianos Joseph Baratta Company Realty

  23 Eagle St, Monroe, NY 10950
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  /44

  $674,999

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

  9 Mount Ridge Ct, Monroe, NY 10950

  Tucked away on a quiet cul-de-sac, 9 Mount Ridge Court offers a rare opportunity to own a lovingly maintained 5-bedroom, 3-bath home with 3,000 square feet of light-filled living space. Owned and cared for by the original homeowner since day one, this residence combines warmth, comfort, and flexibility—ready for its next chapter.Step inside to find spacious, sun-filled rooms with an easy

  James Feldhaus eXp Realty

  9 Mount Ridge Ct, Monroe, NY 10950
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  /3

  $685,000

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  12 Edgewood Dr, Harriman, NY 10926

  Welcome to this stunning new construction being built at 12 Edgewood Dr, located in the charming Town of Monroe. This beautiful Hi-Range style home features 4 spacious bedrooms and boasts a total of 7 well-designed rooms, offering ample space for family living. With three full baths, convenience will be prioritized for your daily routines. The home spans an impressive 2,150 sq ft, with the full

  Nathen Singer MK Realty Inc

  12 Edgewood Dr, Harriman, NY 10926
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  /2

  $699,000

  • 2 Beds
  • 1.5 Baths
  • 1,006 Sq Ft

  252 Schunnemunk Rd, Monroe, NY 10950

  Charming Opportunity Awaits!** Discover the perfect blend of privacy and potential with this beautifully maintained cozy home, nestled on a spacious, flat lot with ample frontage. Located in a highly sought-after area, this property offers a fantastic opportunity to build your dream home or even consider a subdivision, Currently, you can design and construct a stunning 3,500 sq. ft. residence,

  Joel Basch eRealty Advisors, Inc

  252 Schunnemunk Rd, Monroe, NY 10950
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  /35

  $690,000

  • 3 Beds
  • 3 Baths
  • 3,200 Sq Ft

  23 Renies Rd, Chester, NY 10918

  Escape to your own sanctuary in this stunning 3 bedroom 3 full bath contemporary cedar home, perfectly blending modern comfort with natural charm. Inside you'll find an open-concept layout with soaring ceilings, large windows, and natural wood finishes that create a warm, modern vibe. The spacious kitchen features stainless appliances, hickory cabinets and an island ideal for entertaining. Two

  Kristie Jacques Century 21 Full Service Realty

  23 Renies Rd, Chester, NY 10918
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  /34

  $645,000

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

  4 Mack Place, Monroe, NY 10950

  Check this out!! Are you looking high n low for that exclusive HOME? Well, you've found it!!This exceptional, move-in ready home perfectly combines space, style, and a prime location!Boasting a bright, open floor plan, generous bedrooms, and versatile living areas, this property is ideal for both entertaining and comfortable daily life. It has been meticulously maintained and is

  Joseph Rosenfeld Flag Realty Group

  4 Mack Place, Monroe, NY 10950
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  /10

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,376 Sq Ft

  264 Heritage Ln, Monroe, NY 10950

  Move-In Ready 3-Bedroom Condo in the Monroe-Woodbury School District. Discover comfort, convenience, and community in this 3-bedroom, 1.5-bath condo located in one of the most desirable areas of the Hudson Valley. The open-concept main level features a bright and spacious living room, a dining area, and a well-appointed kitchen—perfect for everyday living and entertaining. Upstairs, you’ll find

  Frank Golio Howard Hanna Rand Realty

  264 Heritage Ln, Monroe, NY 10950
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  /45

  $674,999

  • 5 Beds
  • 2.5 Baths
  • 3,115 Sq Ft

  507 Bull Mill Rd, Chester, NY 10918

  Welcome to this beautifully maintained colonial with a charming wrap-around front porch, set on 1.5 private acres within the sought-after Monroe-Woodbury School District. Offering over 3,100 square feet of living space, this 5-bedroom, 2.5-bath home blends timeless style with thoughtful design.Step inside the two-story foyer and you’ll find a bright, flowing layout designed for both

  Alison Orlando Keller Williams Hudson Valley

  507 Bull Mill Rd, Chester, NY 10918
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  /33

  $344,000

  • 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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  /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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  /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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  /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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  /46

  $650,000

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

  117 Woodland Rd, Highland Mills, NY 10930

  This beautifully updated Colonial-style home offers space, flexibility, and modern comfort—perfect for multi-generational living or added rental income. With 6–7 bedrooms, 3 full bathrooms, and 2 full kitchens, there’s room for everyone!Located in the desirable Monroe-Woodbury School District, the main level of the home was renovated in 2024. The kitchen now features stainless steel

  Karin Poggio HomeSmart Homes & Estates

  117 Woodland Rd, Highland Mills, NY 10930
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  /48

  $739,900

  • 4 Beds
  • 2.5 Baths
  • 2,434 Sq Ft

  33 Sutherland Dr, Highland Mills, NY 10930

  Welcome to Greenway Estates – Highland Mills, NYThe desirable Greenway Estates, this beautifully maintained Colonial is nestled on a serene 1.2-acre lot in a quiet cul-de-sac. The perfect blend of elegance, comfort, and privacy. Boasting 4 bedrooms and 2.5 baths across 2,500 sq. ft. of living space, this home is surrounded by mature trees and lush landscaping for a tranquil

  Kim Chiapperino RE/MAX Benchmark Realty Group

  33 Sutherland Dr, Highland Mills, NY 10930
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  /33

  $699,000

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

  4 Sequoia Trail, Highland Mills, NY 10930

  Located in the charming neighborhood of Highland Mills, the newly renovated 2004 sq ft house at 4 Sequoia Trail offers a perfect blend of comfort and modern living. With beautifully landscaped grounds and ample outdoor space, this home provides a peaceful retreat from everyday life. As you ascend to the top level, you are welcomed by a spacious living room. Bright and airy, this space features

  Moshe Kaufman MK Realty Inc

  4 Sequoia Trail, Highland Mills, NY 10930
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  /48

  $669,900

  • 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
• 

  

  /4

  $570,000

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft

  12 Yale Dr, Highland Mills, NY 10930

  Nice, Four bedroom house in Highland Lake Estates. Set on a hill, this home feature an open floor plan with cathedral ceilings in the kitchen, dining and living rooms. Primary bedroom with fill bath plus two more spacious bedrooms and main bath on first level. The lower level is home to the fourth bedroom, family room and half bath, plus laundry room. Large two car garage, park like property

  Richard Froehlich RE/MAX Benchmark Realty Group

  12 Yale Dr, Highland Mills, NY 10930
• 

  

  /11

  $375,000

  • Land
  • 4.9 Acres
  • $76,531 per Acre

  8 Camelback Rd, Chester, NY 10918

  Nestled at the end of a private cul-de-sac, this 5 acre homesite offers breathtaking mountain and valley views in the sought-after Bull Mill Road area of Monroe/Chester, NY.The property’s gentle slopes create the perfect opportunity for a walkout lower level, allowing you to capture spectacular sunsets.This shovel-ready, fully approved, and engineered building lot features Belgian

  James Feldhaus eXp Realty

  8 Camelback Rd, Chester, NY 10918

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