Monroe-Woodbury Homes under $400,000

Welcome to the Monroe-Woodbury School District, a vibrant and nurturing educational community nestled in the heart of Orange County, NY. Renowned for its commitment to academic excellence and holistic development, Monroe-Woodbury serves a diverse population of students from the charming towns of Monroe, Woodbury, and surrounding areas. With a focus on fostering critical thinking and creativity, the district offers a rich curriculum complemented by a variety of extracurricular activities, ensuring that every child can thrive both inside and outside the classroom.

Parents will appreciate the district's strong emphasis on community engagement and support, with numerous resources available to assist families in navigating their educational journey. From dedicated teachers to innovative programs, Monroe-Woodbury is passionate about cultivating a love for learning, preparing students for success in an ever-evolving world.

For those looking to settle in this exceptional district, the real estate market has exciting opportunities! Homes under $400,000 are available, making it an attractive option for first-time buyers, families, and anyone looking to enjoy the benefits of suburban living without breaking the bank. Whether you prefer a cozy single-family home or a charming townhouse, you’ll find a variety of options that cater to different tastes and lifestyles.

Living in the Monroe-Woodbury School District means more than just a great education; it’s about becoming part of a welcoming community with access to parks, recreational facilities, and a strong sense of local pride. Explore your options today and discover the perfect home in this delightful area!

Newest Monroe-Woodbury Homes under $400,000

$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

$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

$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

$359,999

2 Beds ⋅ 3 Baths ⋅ 1049811 MLS

A place to feel right at home! This 2-bedroom, 2.5-bathroom Timber Hills condo in the Monroe-Woodbury School District offers the perfect combination of comfort, convenience, and room to grow. The spacious primary suite features a walk-in closet and private ensuite bath, while the full basement gives you plenty of space for storage or the potential for a bar, office, gym, or recreation room. Enjoy your morning coffee on the private deck or relax in the spacious living room at the end of the day. When it’s time to get outside, owners have access to the community pool, clubhouse, parks, tennis courts, and basketball courts. Conveniently located close to town, shopping, dining, and public transportation to NYC, this is an easy place to settle in and enjoy all that the area has to offer.

14 Giovanni Court, Monroe

$339,900

2 Beds ⋅ 1 Baths ⋅ 1046033 MLS

Discover the charm of 18 Schueler Road, an inviting 2-bedroom, 1-bath home in the Monroe-Woodbury School District. Tucked along a private road with a road maintenance agreement in place, this cozy home offers a peaceful Hudson Valley setting. Step inside to a comfortable living space and an adorable, colorful kitchen that brings warmth, personality and character to the home. Two bedrooms and a full bath complete the easy-to-manage layout. The recently re-stained exterior adds to the home’s fresh, well-cared-for appeal. Conveniently located near shopping, dining, recreation and major commuter routes, 18 Schueler Road is a charming opportunity for first-time buyers, those looking to simplify, or anyone searching for a home with personality and room to make it their own.

18 Schueler Road, Chester

$399,900

3 Beds ⋅ 1 Baths ⋅ 1049008 MLS

Sun-filled from the moment you enter, this 3-bedroom home offers a warm, welcoming interior surrounded by spacious property, with Sapphire Lake access only a 3-minute walk away. The bright entryway opens into the living room, where a beautiful stone fireplace with an energy-efficient wood stove insert brings character to the heart of the home. An eat-in kitchen plus formal dining room provide space for everyday meals and gatherings. Recent improvements include a newer roof, new hot water heater, updated appliances, water softener, washer/dryer, and new leach fields. A one-car garage, multiple parking spaces, and large shed add valuable storage. Lake rights offer access to swimming, kayaking, fishing, and non-motorized boating. Conveniently located near the Village of Harriman, Woodbury shopping, dining, Metro-North, and major commuter routes, with NYC approximately one hour away. Easy commute to NYC by bus or train. Located in the Monroe-Woodbury School District.

101 Highland Road, Monroe

$389,000

4 Beds ⋅ 1 Baths ⋅ 1046180 MLS

Welcome to 4 Grove St, a charming and private residence nestled in the heart of Harriman, NY. This inviting home offers 4 spacious bedrooms and a total of 7 bright, versatile rooms—perfect for living, entertaining guests, or creating your ideal home office or playroom. Set on a generous 0.7-acre lot, the property provides ample outdoor space for relaxing, gardening, or enjoying gatherings in your own secluded oasis. Enjoy the peace and privacy of a standalone house while being conveniently located near local amenities and major routes. Discover comfort, space, and tranquility at 4 Grove St—your next place to call home. 3 Minute drive to major to Woodbury Common Mall! Rare opportunity to find, less than 400k!

4 Grove Street, Harriman

$350,000

2 Beds ⋅ 1 Baths ⋅ 1046861 MLS

Discover the possibilities in this charming 2-bedroom, 1-bath home situated on a spacious .37-acre lot in Monroe, NY. Whether you're searching for the perfect weekend retreat, first home, downsizing opportunity, or investment property, this home offers flexibility and potential to fit a variety of lifestyles. Enjoy the convenience of being close to major highways, shopping, dining, schools, and everyday amenities, while still having your own space to relax and unwind. The manageable size and generous lot make this property an appealing option for those looking for a simpler lifestyle without sacrificing location. With its desirable Monroe location and multiple possibilities for use, this home is an opportunity not to be missed. Come see how you can make this property your own!

33 E Crossman Avenue, Monroe

$369,900

2 Beds ⋅ 2 Baths ⋅ 1039455 MLS

Luxury Living at its very Best! 45 min to NYC. This Gorgeous Home features Bamboo Flooring Throughout, New Windows, Doors and Water Softener. Inviting Entry with Vaulted Ceilings and Skylight. Designer High End Kemper Kitchen, with beautiful Granite Countertops with breakfast Bar, with Pendulum lighting, Tumbled Marble Backsplash, Top of the Line Jen Air Refrigerator & Dishwasher, Capital Commercial Stove with Gas Grill, 1200 CFM Blower, and Recessed Lighting. Living Rm with Custom Stone Gas. Spacious Formal Dining Rm, Laundry Rm. Bathroom with custom tiled stone inlay floor, Maple Vanity with Granite Countertop and Maintenance Free Tub / Shower. Generous size bedroom. Huge Master Br Suite with recessed lighting, Spacious Walk in Closet and Additional Closet. Spa Bathroom that offers Marble Flooring, Cherry Vanity with Marble top, 2 Person Marble Shower that includes a Bench seat, Waterfalls, and a rain Shower Head. Private Backyard that backs up to woods. Additional Information: Amenities: Tennis, ParkingFeatures:1 Car Attached,

7 Ironwood Drive, Highland Mills

$345,000

3 Beds ⋅ 2 Baths ⋅ 1043714 MLS

Welcome to Harriman Hills! This beautifully maintained, move-in-ready 3-bedroom, 1.5-bath townhome offers a comfortable layout, modern updates, and low-maintenance living in a desirable community. The main level features a spacious living and dining area with wood flooring, a convenient powder room, and an updated kitchen with stainless steel appliances, and a peninsula with seating. Sliding glass doors open to a private balcony/porch—perfect for enjoying your morning coffee or relaxing outdoors. The upper level offers three bedrooms, a full bathroom, and ample closet space. The lower level includes an attached one-car garage, in-unit washer and dryer, and additional storage. Harriman Hills has recently been updated with new siding and a new roof. Community amenities include a swimming pool and tennis courts. Conveniently located near shopping, restaurants, parks, and public transportation, with an easy commute to surrounding areas. A wonderful opportunity to own a well-maintained home in a convenient and amenity-rich community!

9 Heritage Drive Unit #B, Harriman

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