Monroe-Woodbury Homes under $300,000

Welcome to the Monroe-Woodbury School District, a vibrant and nurturing educational community located in the heart of Orange County, New York. Known for its commitment to academic excellence, Monroe-Woodbury serves a diverse population of students from the charming towns of Monroe, Woodbury, and surrounding areas. The district is recognized for its innovative programs, dedicated faculty, and a wide array of extracurricular activities that foster both personal and academic growth.

Families in the Monroe-Woodbury area benefit from a strong educational foundation, with schools that prioritize student achievement and well-being. The district boasts a range of resources, including state-of-the-art facilities, advanced placement courses, and a focus on STEM education. With a supportive community and active parental involvement, students are encouraged to explore their interests and develop their talents.

For those looking to settle in this picturesque region, there are beautiful homes available for under $300,000, making it an ideal choice for first-time buyers, young families, or anyone seeking a peaceful retreat with excellent educational opportunities. These homes offer a perfect blend of affordability and comfort, often featuring spacious layouts, modern amenities, and proximity to local parks and recreational facilities.

Living in the Monroe-Woodbury area means enjoying a sense of community, access to top-notch schools, and a variety of housing options that fit your budget. Discover the charm of this thriving district and find your perfect home today!

Newest Monroe-Woodbury Homes under $300,000

$259,000

2 Beds ⋅ 2 Baths ⋅ 1050249 MLS

LEXINGTON HILLS! 2ND FLOOR LOCATION! ENJOY RESORT-STYLE LIVING WITH POOL AND TENNIS COURTS POSITIONED AT YOUR DOORSTEP! Unlike the standard denser phases of the complex, this premium unit is situated within a COMPLETELY INDEPENDENT BUILDING. Tucked away from the heavier traffic loops, it offers the quiet feel of an isolated retreat while keeping the community pool and tennis courts right outside your door. Enjoy SINGLE LEVEL LIVING in this immaculate 2-bedroom, 2-full-bathroom condo which is completely move-in ready, boasting stunning LAMINATE FLOORING THROUGHOUT, NEWER BOILER and IN-UNIT WASHER/DRYER for ultimate everyday convenience. The heart of the home features a spacious living room and dining area, highlighted by a cozy WOOD BURNING FIREPLACE that adds incredible warmth and character to the space. This bright and airy living area is bathed in natural light, with TWO BRAND NEW WINDOWS and a NEW GLASS SLIDER that leads to the OUTDOOR BALCONY! The seamlessly connected kitchen comes fully equipped with a NEWER STOVE, ready for your culinary creations. Both bedrooms are generously sized, highlighted by a serene PRIMARY SUITE complete with its own PRIVATE FULL BATH and LARGE WALK-IN CLOSET with ample storage space. A second full bathroom and bedroom serve guests beautifully. For added logistics, a newly installed, easily ACCESSIBLE INTERIOR WATER SHUT-OFF VALVE is strategically located in the bathroom. Amenities include: Outdoor Pool, Tennis & Pickleball Courts and Clubhouse. This home offers simplistic practicality and EASY ACCESS TO TRANSPORTATION for commuting/leisure trips and is just minutes away from world-class shopping at the Woodbury Common Premium Outlets. Close to MAJOR SHOPPING and RESTAURANTS! Located within the AWARD-WINNING Monroe-Woodbury School District.

4 Lexington Hill Unit #3, Harriman

$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

$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

$299,900

3 Beds ⋅ 3 Baths ⋅ 1042633 MLS

**Potential short sale, subject to third-party approval. Opportunity knocks in Walton Park. 72 Lake Region Blvd is a 3-bedroom, 2 bath home offering 1,854 square feet on a 9,690 square foot lot, and it has the one thing you cannot renovate into a house: excellent bones. Hardwood floors, a solid structure, a 2-car garage, and a layout worth restoring. The home needs renovation including a new roof, and it is priced accordingly at 399,000. Oil heat and a whole house water softener in place. Live minutes from Walton Lake, 117 acres stocked with trout each spring, and the paved Orange County Heritage Trail. Woodbury Common Premium Outlets is about 5 miles away. Harriman Metro-North and Thruway Exit 16 are roughly 10 minutes out, and the Monroe Park and Ride runs direct to Port Authority. Monroe-Woodbury Central School District. Bring your contractor and your vision. This one is priced to sell.

72 Lake Region Boulevard, Monroe

$250,000

3 Beds ⋅ 3 Baths ⋅ 1037650 MLS

Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing windows open toward the porch and offer seasonal lake views — a lovely everyday backdrop. Sunlight flows easily throughout the main living area, creating a warm and comfortable setting. The newer designer-style eat-in kitchen features tall white cabinetry with crown moldings, tile backsplash, and quartz countertops. White appliances maintain the bright, clean aesthetic, and a younger sliding door leads to the patio for relaxing outdoor enjoyment. The first floor includes an updated half bath too. The spacious and bright primary suite offers two closets for excellent storage, and the primary bath includes a shower updated within the past five years. Two additional bedrooms share their own guest bathroom, providing comfortable separation and functionality for household members or visitors. A meaningful financial benefit — heat is included in the common charges, eliminating furnace maintenance or replacement expenses and simplifying monthly budgeting. A large basement is unfinished and has your washer and dryer set up. Great for storage and laundry. Windridge residents enjoy access to a pool, clubhouse, playgrounds, and a serene lake where you can fish from the dock or enjoy non-motorized boating. Ideal for walking, biking, or jogging, the enclosed neighborhood has no through traffic unless you live in Windridge, providing a peaceful setting. Located in the Town of Chester within the Monroe-Woodbury School District — known for sought-after schools while benefiting from some of the lowest school taxes per square foot. The roof and the siding were replaced in 2023 too! A wonderful opportunity to enjoy community living with recreation, convenience, and everyday comfort.

607 Mountain Laurel Drive, Monroe

$265,000

2 Beds ⋅ 1 Baths ⋅ 1036803 MLS

Charming and low-maintenance living awaits in this delightful 2-bedroom, 1-bathroom ranch home, nestled between two beautiful lakes, located in the heart of Monroe, NY. Perfectly sized for first-time homebuyers, downsizers, or anyone seeking the ease of single-level living, this property combines cozy comfort with an unbeatable location. Step inside to a bright and welcoming living space that flows seamlessly into an efficient kitchen, ideal for preparing home-cooked meals. Both bedrooms offer comfortable accommodations and share a centrally located, full bathroom. The classic ranch layout ensures maximum functionality with no stairs to navigate. Outside, the property features a manageable yard perfect for weekend barbecues, gardening, or relaxing in the fresh air. Located just minutes away from local shopping, dining, parks, and major commuter routes. Bring your personal touches to make this lovely house your home!

92 Walton Terrace, Monroe

$300,000

2 Beds ⋅ 1 Baths ⋅ 1034445 MLS

Situated in a quiet neighborhood on level corner property. House is in need of complete renovation. A suitable project for experienced contractor/builder.

102 Hillcrest Avenue, Monroe

$242,000

1 Beds ⋅ 1 Baths ⋅ 1018246 MLS

Welcome to this beautifully maintained 1-bedroom, 1-bath condominium in excellent condition. This bright and inviting home features, brand new bathroom, new flooring, new windows and a new sliding glass door that opens to a nice size patio—perfect for relaxing or enjoying your morning coffee. Kitchen features granite countertops and tile backsplash. Lots of closet space. Also there are two new a/c units, washer and dryer in unit and large storage room in basement area of building. Conveniently located near major highways, public bus routes, the train station, and a variety of shopping, dining, and everyday conveniences, this condo offers the ideal combination of comfort, quality, and accessibility. Whether you're a first-time buyer, downsizing, or looking for a low-maintenance lifestyle, this move-in-ready home is a wonderful opportunity.

8 Heritage Drive Unit #E, Harriman

$250,000

2 Beds ⋅ 1 Baths ⋅ 1006554 MLS

Welcome Home! Well maintained two bedroom unit with lake and mountain views. Spacious living room with access to a private balcony. Eat in kitchen has updated counter tops and new appliances. Both bedrooms have ample closet space. Windridge is a quiet community conveniently located minutes from town. Great commuter location. Amenities include pool, playground, tennis and basketball courts, clubhouse. Heat and Hot Water included in the HOA & Low Taxes

804 Swan Hollow Road, Monroe

$245,000

2 Beds ⋅ 2 Baths ⋅ 984536 MLS

Find your perfect home in the heart of Lexington Hills with this desirable lower-level Unit. Experience the best of community living with the added benefit of a secluded, quiet location. Ideal for simplifying life, this unit offers turn-key readiness and is situated just moments from local dining, shopping, and major commuter routes. Enjoy the ease of a lower-level residence with excellent accessibility offering unparalleled convenience and quiet living. This end unit is perfect for buyers seeking an accessible, easy-to-manage home or a smart investment opportunity. Enjoy hassle-free living in a desirable community setting.

18 Lexington Hill Unit #8, Harriman

$275,000

1 Beds ⋅ 1 Baths ⋅ H6317833 MLS

Welcome Home! This uniquely styled 1st floor condo features comfort, convenience & privacy. This end unit features a large eat-in-kitchen with updated appliances, pantry and walk-out to your own rear deck. Beautiful crown molding throughout with custom blinds and unique stone wall with mantel fireplace & firebox. Large second room features custom cabinetry and can be used as 2nd bedroom with some modification or dining room with very large closet storage. Upgraded radiators, thermostats, switches and outlets. Andersen windows and Silver Line sliding doors. Interior doors have all been replaced and entry door is steel, fire rated. Custom bathroom shower and wall enclosure. Hardwood Floors under carpeting. You'll enjoy the oversized Garage with new overhead door which is also heated and dehumidified. Great commuter location with access to all major highways, train station, bus stop, Harriman St. Park, & Woodbury Common. This pet friendly complex also has a playground. Schedule your showing today!! Additional Information: Amenities:Storage,ParkingFeatures:1 Car Attached,1 Car Detached,

407 Old Mill Road, Southfields

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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.