Monroe-Woodbury Homes under $750,000

Welcome to the Monroe-Woodbury School District, a cornerstone of educational excellence nestled in the heart of Orange County, New York. This vibrant community is not only known for its scenic beauty and welcoming neighborhoods but also for its commitment to fostering a nurturing learning environment for students of all ages. With a strong emphasis on academic achievement, the Monroe-Woodbury School District boasts a variety of programs designed to cater to diverse learning styles and interests, ensuring that every child has the opportunity to thrive.

Families looking to settle in this desirable area will be pleased to discover a range of charming homes available for under $750,000. From cozy single-family residences to spacious modern townhouses, there’s something to fit every lifestyle and budget. The real estate market here offers a unique blend of affordability and quality, making it an ideal choice for first-time homebuyers, growing families, or anyone looking to enjoy the tranquility of suburban living without sacrificing access to urban conveniences.

Living in Monroe-Woodbury means not only enjoying a beautiful home but also being part of a community that values education and growth. With top-rated schools, dedicated teachers, and a wealth of extracurricular activities, your children will have access to the tools they need to succeed. Plus, with the stunning backdrop of the Hudson Valley, outdoor enthusiasts can enjoy hiking, biking, and exploring nature right at their doorstep.

Discover the charm of Monroe-Woodbury, where excellent schools and affordable homes come together to create a perfect place for families to flourish.

Newest Monroe-Woodbury Homes under $750,000

$280,000

2 Beds ⋅ 2 Baths ⋅ 1058123 MLS

Welcome to 41 Berwynn Road #2D, a beautifully maintained 2-bedroom, 1.5-bath condo nestled in a quiet, sought-after community in Harriman, NY. Step inside to discover soaring ceilings with skylights that flood the space with natural light. The open-concept living and dining area features direct access to your own private balcony—perfect for morning coffee or evening relaxation. The layout includes two spacious bedrooms, a full bathroom, and a convenient half-bath for guests. Whether you're looking for a starter home, a downsizing opportunity, or a low-maintenance investment, this unit delivers. Enjoy the peace and privacy of this quiet community, all while being just minutes from local shops, dining, and public transportation—ideal for commuters or anyone who enjoys easy access to amenities.

41 Berwynn Road Unit #2D, Harriman

$549,000

3 Beds ⋅ 3 Baths ⋅ 1056648 MLS

Located in the gated community of Meadow Glen, this end unit 3 bedroom townhouse has all the amenities you possibly want. Conveniently located near shopping, trains, hiking paths in Monroe, NY. The first floor has more than ample living space with both a formal living room and family room that has a gas fireplace. The kitchen with it's stainless steel appliances has lots of natural light through the sliding glass doors which lead to your own patio. The primary bedroom is oversized with plenty of closet space. 2 other bedrooms along with a full bath and laundry room complete the 2nd floor. This home comes with a full basement that is perfect for storage. Community offers a swimming pool, club house and tennis courts. Easy access to highways and shopping. Plenty of guest parking is available.

24 Ford Court, Monroe

$565,000

3 Beds ⋅ 3 Baths ⋅ 1056905 MLS

Ask how you can get a Mortgage with a 4.5%- 5% start rate! Welcome to Meadow Glen—Monroe’s premier gated community! With over 2500 sq ft including the finished basement, this beautifully maintained and extensively upgraded largest-model end-unit offers an exceptional combination of space, style, privacy, and convenience. With 24 oversized windows, this home is filled with natural light, while Hunter Douglas Country Wood blinds throughout add a touch of timeless elegance. Step inside to a spacious and inviting layout designed for both comfortable everyday living and entertaining. The dramatic two-story family room creates an impressive focal point, complemented by a formal living room and elegant dining room. The beautifully appointed kitchen features Corian countertops, breakfast bar, GE Profile stainless steel appliances, 42-inch cabinetry, convenient pull-out drawers, and a classic subway-tile backsplash. Rich hardwood flooring flows throughout the first and second levels. Upstairs, the luxurious primary suite is a true retreat, featuring a soaring cathedral ceiling, two walk-in closets, and a spa-like ensuite bath with dual sinks, a large soaking tub, and frameless glass shower. Two additional generously sized bedrooms offer double closets, along with a full hallway bath and the highly desirable convenience of second-floor laundry. The fully finished walk-out basement adds an approximately additional 600 sq ft of flexible living space, complete with full-size windows, sliding glass doors to a private patio, a spacious recreation/media area, and additional storage. Whether you envision a home theater, game room, home office, gym, or entertaining space, the possibilities are endless. Plus a storage room. Additional highlights include an attached garage with direct first-floor entry and no stairs, plus a double-wide driveway providing plenty of parking for family and guests. Enjoy all that Meadow Glen has to offer, including beautifully maintained grounds, gated security, and a convenient location close to shopping, restaurants, parks, wineries, major highways, and commuter transportation. If you’ve been waiting for a spacious, upgraded end-unit in one of Monroe’s most desirable communities, this is the one to see! Schedule your private showing today.

116 Barr Lane, Monroe

$750,000

4 Beds ⋅ 4 Baths ⋅ 1057348 MLS

Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home. Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday living and entertaining. Sunlight pours into the beautiful sunroom, offering the perfect place to enjoy your morning coffee, unwind with a good book, or simply take in the tranquil views of the property throughout every season. Step outside and discover the true highlight of this remarkable property. Designed with entertaining in mind, the backyard is a private oasis featuring a sparkling inground pool, beautifully integrated outdoor living spaces, a custom built fire pit, and built in seating that invites family and friends to gather long after the sun goes down. Whether you're hosting summer pool parties, enjoying crisp fall evenings by the fire, or simply relaxing in your own backyard retreat, this outdoor space delivers an exceptional lifestyle year round. Set on over three private acres, the property offers the perfect balance of open space and privacy. There is plenty of room to explore, play, garden, or simply enjoy the serenity of nature, all while being just minutes from the conveniences of the Hudson Valley. Offering 4 bedrooms, inviting living spaces, and an outdoor setting that feels like your own private resort, this is more than just a home. It is a place where memories are made, weekends are enjoyed, and every season brings something special.

985 Craigville Road, Chester

$299,900

2 Beds ⋅ 2 Baths ⋅ 1057334 MLS

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 bright, cohesive feel throughout. Enjoy central air conditioning and a private deck—an inviting spot for morning coffee or relaxing outdoors. Residents also have access to the community pool. With thoughtful updates from top to bottom, this move-in-ready condo is ready to welcome its next owner.

308 Magnolia Court, Highland Mills

$330,000

2 Beds ⋅ 2 Baths ⋅ 1056467 MLS

Welcome to 1108 Evergreen Court in Woodbury! This desirable end-unit condo offers added privacy and a great location next to the community pool. Enter through the foyer before heading upstairs to the main living area, where you’ll find a bright and inviting layout. The living room opens to a private deck, providing a great spot to relax and enjoy the outdoors. The galley-style kitchen offers convenient seating and opens to a separate dining area, perfect for everyday meals or entertaining. A detached garage with electric provides additional parking and storage, plus there is plenty of unassigned parking for residents and guests. Enjoy low-maintenance living with community amenities and convenient access to shopping, dining, recreation, and major roadways. With its end-unit location, deck, garage, ample parking, and proximity to the pool, 1108 Evergreen Court has plenty to offer!

1108 Evergreen Court Unit #65, Woodbury

$599,000

4 Beds ⋅ 5 Baths ⋅ 1049653 MLS

Perched beautifully atop a scenic hill, this lovingly maintained home has been cherished by its original owners and offers a rare combination of privacy, space, and timeless charm. Set on a stunning property in a desirable Chester location, the home contains unique features including a beautiful sunroom, a detached three-car garage, and an additional one-car attached garage, providing exceptional parking and storage. Inside, the home has been kept in immaculate condition and offers an excellent opportunity for its next owner to personalize and make it their own. A wonderful opportunity to own a spacious home on a beautiful piece of property in a great location.

111 Ayr Road, Chester

$549,000

4 Beds ⋅ 2 Baths ⋅ 1056405 MLS

Lovely 4-bedroom, 2-bathroom home in quiet, tree-lined neighborhood, cared for by the same owners for the past 50 years! This large corner lot property invites you to make memories! The lower level family room, bathroom, additional bedroom, as well as the upstairs bathroom have all recently been renovated. Walk out from the eat-in kitchen to a large deck that invites to al fresco dining; leased solar panels provide substantial energy cost savings. Conveniently located near shopping and dining, commuter bus and train service. Come and see what this home, located in the beautiful Hudson Valley has to offer!

50 Lincoln Road, Monroe

$569,900

3 Beds ⋅ 3 Baths ⋅ 1056824 MLS

Rare Lehigh End-Unit Townhome in Gated Meadow Glen Welcome to an exceptional opportunity in the sought-after gated community of Meadow Glen! This gorgeous Lehigh model end-unit is one of only 10 Lehighs in the entire Meadow Glen development and offers the highly desirable combination of larger bedrooms, abundant natural light, an end-unit location, and a two-car garage. From the moment you enter, you’ll appreciate the impressive sense of space created by the high ceilings, oversized windows, beautiful hardwood floors, crown molding, and tremendous natural light throughout the home. The current owners immediately fell in love with this model because the bedrooms are larger than those in other Meadow Glen models, while the end-unit location provides additional windows, privacy, and light. The beautifully appointed kitchen features granite countertops, a gorgeous breakfast bar, and a five-burner gas range. The KitchenAid stainless-steel dishwasher complements the kitchen, while the refrigerator and microwave were replaced in 2024 and the gas stove was replaced in 2023. A convenient slider off the kitchen leads directly to the patio, creating an ideal flow for morning coffee, entertaining, or relaxing outdoors. The spacious family room is warm and inviting, featuring a gas fireplace, beautiful ceiling fan, hardwood floors, and plenty of natural light. The formal living room and dining room are equally impressive, with hardwood floors, elegant lighting, additional recessed lighting, and custom details throughout. All existing light fixtures stay, along with the home’s beautiful custom Hunter Douglas window treatments. Upstairs, the generously sized primary suite spans the full width of the unit, offering an exceptional retreat with recessed lighting, beautiful Hunter Douglas shades, and a large walk-in closet. The luxurious primary bath features a soaking tub, double sinks, and Corian countertops. Convenience is built right in with an upstairs laundry area featuring a washer and dryer, laundry base, and slop sink—all of which stay. The home also offers central vacuum, making everyday living even easier. The home’s mechanicals have been thoughtfully maintained. The HVAC system is approximately five years old, and the hot water heater was installed just over two years ago. Even better, the owner is willing to pay the current roof assessment, meaning the community will soon have a brand-new roof without that assessment becoming the buyer’s expense. Enjoy all that Meadow Glen has to offer, including a community pool, clubhouse, tennis courts, playground, and beautifully maintained grounds. This is a wonderful, gated community offering both amenities and a strong sense of privacy. And the location is truly special. Set in the beautiful Hudson Valley, Meadow Glen is conveniently located near West Point, Harriman Train Station, major highways, Stewart International Airport, and Storm King Art Center, making commuting, travel, recreation, hiking and exploring the region remarkably convenient. Woodbury Common Premium Outlets and LEGOLAND New York are also close by. For outdoor enthusiasts, miles of hiking trails and lakes await nearby at Harriman State Park, Sterling Forest, and the Heritage Trail. With its rare Lehigh model, end-unit position, two-car garage, oversized bedrooms, exceptional natural light, high ceilings, extensive hardwood flooring, custom Hunter Douglas shades, upgraded kitchen, newer appliances, fireplace, patio, and desirable Hudson Valley location, this home truly stands apart. A rare opportunity to own one of Meadow Glen’s limited Lehigh end units—beautifully maintained, thoughtfully upgraded, and ready to welcome its next owner.

105 Barr Lane, Monroe

$385,000

3 Beds ⋅ 2 Baths ⋅ 1055830 MLS

AFFORDABLE, CONVENIENT & FULL OF POTENTIAL IN MONROE. With home prices continuing to rise, 25 Oreco Terrace offers a fantastic opportunity to own a single-family home in the Town of Monroe for under $386,000—complete with low taxes and plenty of potential to make it your own. Set atop a hill on a quiet dead-end street with minimal traffic, this charming bungalow offers simple, convenient single-floor living. The main level features a country kitchen, spacious living room with a wood-burning stove, three comfortably sized bedrooms, and 1.5 bathrooms. Need more room? The partially finished basement provides valuable bonus space along with laundry and storage. Create a home office, family room, game room, gym, hobby space, or den—the possibilities are yours. One of the home's standout features is the expansive nearly 700-square-foot composite deck, overlooking the treetops and quarter-acre yard. Whether you're enjoying your morning coffee, hosting friends and family, or simply relaxing outdoors, this is a wonderful space to enjoy the peaceful surroundings. The location offers exceptional convenience. Situated across from Town of Monroe O&R Park, Twin Lakes, and the Park & Ride, you're also just minutes from the village center and close to shopping, restaurants, groceries, big box stores, schools, parks, medical offices, houses of worship, Woodbury Common Premium Outlets and much more. Commuters will appreciate the nearby Park & Ride and easy access to Route 208, with Route 17 just seconds away and convenient connections to the NYS Thruway, Route 6, and other major roadways. The Bear Mountain Bridge is approximately 20 minutes away, and NYC is roughly an hour by car. Additional highlights include natural gas, municipal water and sewer, Monroe-Woodbury School District, and low taxes that include garbage pickup. Whether you're a first-time buyer searching for an affordable place to call home, looking to downsize without sacrificing outdoor space, or an investor seeking an opportunity to expand your portfolio, 25 Oreco Terrace is worth a look. After years of raising their family here, the current owners are ready to pass this home along to its next chapter. Come see the possibilities and discover the potential this Monroe gem has to offer.

25 Oreco Terrace, Monroe

$398,500

3 Beds ⋅ 1 Baths ⋅ 1054704 MLS

Welcome to 57 Osseo Park Road, a charming 3-bedroom ranch offering lake rights and access to beautiful Walton Lake. Lovingly maintained by its longtime owner, this inviting home offers comfortable one-level living in a peaceful lake community. A welcoming enclosed porch provides additional space to relax and enjoy the surroundings, while the fenced yard and corner lot offer plenty of room for outdoor entertaining, gardening or simply unwinding. Recent improvements include a newer roof, furnace, hot water heater, refrigerator and cooktop. Additional features include a partial basement, oil heat, community well and a paved driveway with parking for two cars. Located in the Monroe-Woodbury School District, this home offers the opportunity to enjoy the recreation and natural beauty of Walton Lake while still being convenient to all that Monroe has to offer. Whether you're looking for a year-round home or a relaxing weekend retreat, 57 Osseo Park Road is ready for its next chapter.

57 Osseo Park Road, Monroe

$489,900

2 Beds ⋅ 4 Baths ⋅ 1055610 MLS

Welcome to 2 Seeley Bull St, a stunning townhome nestled in the charming town of Monroe, NY. Built in 2013, this modern and well-maintained property boasts a sleek design and ample living space for a growing family or those who love to entertain. Located in the very desirable sought after community Hidden Creek. Amenities include sparkling in ground pool, elegant clubhouse, fitness center, basketball courts, playground, and steps away from Orange County’s beloved walking and biking Heritage trail. Upon entering the home, you are greeted by a spacious and bright living area that is perfect for relaxing or hosting guests. The open floor plan seamlessly flows into the dining area and gourmet kitchen, complete with high-end appliances, granite countertops, and plenty of storage space. Whether you are whipping up a meal for guest or hosting a dinner party, this kitchen is sure to impress. The home features two full bathrooms and two half bathrooms, providing convenience and privacy for all residents and guests. The bathrooms are beautifully designed with modern fixtures and finishes, creating a luxurious spa-like atmosphere. With a total finished area of 1,777 sq.ft., this three-story home offers plenty of room for everyone to spread out and find their own space. The upper levels feature spacious bedrooms with ample closet space and large windows that let in plenty of natural light. The lower level can be used as a family room, home office, or gym – the possibilities are endless. Situated on a 436 sq.ft. lot, the property also includes outdoor space for relaxing and enjoying the fresh air. Whether you want to sip your morning coffee on the rear deck or host a barbecue in the backyard, this home has it all. This townhome offers a two car garage with ample storage space. Located in a desirable neighborhood, 2 Seeley Bull St is just a short drive away from local schools, parks, shopping, and dining options. With easy access to major highways and public transportation, commuting to nearby cities is a breeze. Don't miss your chance to own this beautiful home in Monroe, NY. Make 2 Seeley Bull St your new address.

2 Seeley Bull Street, Monroe

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.