Highland Falls Real Estate

Welcome to Highland Falls, New York, where education and community spirit come together to create a vibrant environment for families. Nestled in the picturesque Hudson Valley within Orange County, Highland Falls is home to a dedicated and thriving school district that prioritizes student success and community involvement.

The Highland Falls-Fort Montgomery Central School District serves students from pre-kindergarten through high school, offering a comprehensive and nurturing educational experience. With a strong emphasis on academic excellence, the district is committed to providing a well-rounded curriculum that encourages critical thinking, creativity, and collaboration. The schools are equipped with modern facilities and resources, ensuring that students have access to the tools they need to thrive.

The district boasts a range of extracurricular activities, including sports, arts, and clubs, allowing students to explore their passions and develop essential life skills. The dedicated faculty and staff are not only committed to academic achievement but also to fostering a supportive and inclusive environment where every student feels valued and empowered.

Highland Falls is also known for its strong sense of community, where parents, teachers, and local organizations work hand-in-hand to support the educational journey of children. This collaborative spirit enhances the learning experience and creates lasting connections among families.

Living in Highland Falls means being part of a community that values education and invests in the future of its children. With its scenic beauty and welcoming atmosphere, Highland Falls is the perfect place for families seeking a nurturing environment where education flourishes. Discover the charm of Highland Falls and see why it’s an ideal location for your family’s next chapter!

Newest Listings in Highland Falls

$475,000

3 Beds ⋅ 2 Baths ⋅ 1043721 MLS

Welcome to this recently renovated Cape Cod in Highland Falls, offering 3-4 bedrooms, 2 baths, and 1,797 square feet of living space on a 0.32-acre lot. The bright interior features hardwood and tile flooring, a spacious living room with a large picture window, and an open flow into the dining area. The kitchen offers ample cabinetry, quartz counters and stainless-steel appliances, while 2 den/office areas provide flexibility for working from home, hobbies, storage or guest rooms. Spacious bedrooms with large windows bring in plenty of sunlight, while the tiled bathroom features a tub/shower combination. The unfinished basement provides substantial storage capacity and includes a roughed-in bath for added future flexibility. The outdoor spaces are a standout feature, with a large Trex deck offering multiple areas for dining, lounging, and entertaining. A separate firepit area creates another space to enjoy the property, while mountain views can be seen from the grounds and deck. The home also features an updated roof (2022), a new Navian boiler (2023), an upgraded 200-amp electrical box (2022), new siding (2022), and a Ring doorbell. Conveniently located in Highland Falls near Main Street's shops and restaurants, local parks, schools, West Point, and access toward Bear Mountain and the surrounding Hudson Valley.

16 Hillside Avenue, Highland Falls

$450,000

2 Beds ⋅ 3 Baths ⋅ 1043477 MLS

Welcome to this beautifully maintained 2-bedroom, 2.5-bath townhouse style condominium offering approximately 2,000 square feet of comfortable living space in the intimate Winhaven Park Condominiums, a community of approximately 20 residences. The main level features a spacious open floor plan designed for easy everyday living and entertaining. A bright and inviting den filled with natural light provides flexible space for a home office, sitting room, or reading area. The living room features sliding glass doors leading to the deck, creating a seamless connection to the outdoors. Upstairs, you'll find two generously sized bedrooms, including a spacious primary suite with its own private en-suite full bathroom. An additional full bathroom and conveniently located second-floor washer and dryer complete this level. Pull-down attic access provides even more storage space. The finished walk-out basement adds valuable additional living space with a comfortable family room featuring a Murphy bed, making it ideal for overnight guests or flexible multi-purpose use. A mudroom provides interior access to the one-car garage, and throughout the home you'll find an impressive amount of storage. Ideally located near West Point Military Academy, Highland Falls Preserve, and Bear Mountain State Park, this home offers convenient access to recreation, hiking, scenic destinations, and the surrounding Hudson Valley. Meticulously cared for and offering plenty of space across three finished levels, this home is ready for its next owner to move in and enjoy. Community pet policy: No dogs permitted; up to two cats allowed.

26 Winhaven Court, Highland Falls

$240,000

2 Beds ⋅ 1 Baths ⋅ 1040293 MLS

Opportunity awaits at 83 Center Street in the Village of Highland Falls! This 2-bedroom, 1-bath Ranch offers 816 square feet of living space plus a full unfinished walk-out basement. Repairs and improvements have been started but are not complete, offering the next owner the opportunity to finish the home to their own taste. Conveniently located close to West Point, as well as village shops, restaurants and amenities. Whether you’re looking for a primary residence or investment opportunity, this property offers plenty of potential. Priced to sell in its current condition and being sold AS IS.

83 Center Street, Highland Falls

$549,000

4 Beds ⋅ 2 Baths ⋅ 1041268 MLS

Lovely high ranch set in private setting on hill with spectacular Hudson Valley views within village of Highland Falls. Walk to all villages conveniences, shops, restaurants, Cafe, West Point. Enjoy History, culture and sports in this town. Just a 55 minute commute to city via Garrison or Peekskill train lines. 3 Bedroom, optional 4th bedroom, den, office or family room. Spcious open kitchen, dining room, living room. Outdoor decks for relaxing/entertaining or enjoying nature, gardens. The Hudson Valley boasts the scenic outdoors of Bear Mountain/Harriman state parks. Its trails for hiking, lakes for kayaking. Skiing etc. Can't go wrong in this sweet town!

21 Kleitz Avenue, Highland Falls

$85,000

2 Beds ⋅ 2 Baths ⋅ 1038916 MLS

Bring your vision to life in the quaint Hudson View Terrace community! This 2-bedroom, 2-full-bath manufactured home offers an affordable entry into first-time homeownership or a low-maintenance, main-level lifestyle. The primary bedroom features an en-suite full bathroom with both a shower stall and soaking tub, flowing seamlessly into a spacious living room ideal for entertaining. The cozy kitchen provides a warm space for everyday meals, while the second bedroom offers convenient access to the dedicated laundry room and second full bathroom. Updates include a newer refrigerator and boiler. After a short flight of stairs, enjoy main-level living featuring an open-concept on the main floor, plus a convenient storage shed outside. Central air details available in remarks. The land is not included in the sale. Owner in the process of packing. Property being sold as is. Note photos enhanced by AI. In addition to the sale, buyers are subject to final park/property management approval process. Schedule your private tour today!

9 Rivercrest Road Unit #22, Highland Falls

$399,000

2 Beds ⋅ 2 Baths ⋅ 1036855 MLS

Welcome to 30 Villa Parkway in Highland Falls, NY! This well-maintained home offers comfortable living, plenty of storage, and numerous updates throughout. Situated on a spacious 10,075-square-foot lot, this 2-bedroom, 1.5-bath home offers approximately 720 square feet of living space and has been thoughtfully maintained and improved by the current owners. The kitchen features a new electric stove installed in 2022 along with a gas cooktop. The Samsung LP-gas washer and dryer were also installed in 2022 and offer convenient app access. The home is equipped with an LP-gas water heater installed in 2024, while the oil heating system is maintained annually for continued reliability. Additional improvements include new basement windows installed in 2024, a new kitchen door and screen door installed in 2024, and new windows in both the bathroom and kitchen. Outside, the spacious backyard provides room to enjoy the outdoors and features a new retaining wall installed in 2023 and a new shed installed in 2024, offering additional storage for tools, equipment, and outdoor items. Located in Highland Falls, this home provides convenient access to local amenities, shopping, restaurants, parks, and major transportation routes. With its spacious lot, comfortable layout, and numerous recent updates, 30 Villa Parkway is a wonderful opportunity for a buyer looking for a well-cared-for home in the Hudson Valley. Schedule your private showing today and come see everything this home has to offer!

30 Villa Parkway, Highland Falls

$750,000

4 Beds ⋅ 2 Baths ⋅ 1025294 MLS

Be the first to live in this home that was completely reimagined by architect Jorge B. Hernandez, R.A., A.I.A and constructed within the original footprint. Nestled in the Hudson Highlands with seasonal Hudson River views this home offers the quality, efficiency, systems and functionality of true new construction while preserving the character of an established Hudson Highlands neighborhood. Featuring and open concept floor plan with four generous sized bedrooms and two gorgeous full bathrooms. Main level living room with stone surround electric fireplace opens to a stunning center island designer kitchen with premium shaker cabinetry, quartz counters, stylish ceramic tile backsplash and GE Stainless Steel appliance package. Main level has 3 bedrooms and full bathroom offering flexibility for guests, multi-generational living or a home office. Spacious primary suite with walk-in closet and full bath en-suite occupies the 2nd floor, creating ultimate privacy. Premium hand-scraped solid hardwood flooring throughout, Whole house has Andersen 400 Series windows, all new roofing, siding, plumbing, 200 amp electric, LED recessed lighting, new insulation and HVAC systems, insulation, drywall, and wired Cat-6 ethernet throughout. Enjoy seasonal Hudson River views and entertain in style on your expansive covered patio or enjoy your morning coffee on the new maintenance free trex deck. Partial basement for mechanicals and storage, outdoor shed and a covered carport complete this special home in the Highland Falls Fort Montgomery Central School District is just minutes from West Point Academy, Bear Mountain, Harriman State Park, Metro-North, the Bear Mountain Bridge and major commuter routes. Approximately 1 hour to Manhattan and 10 minutes to Peekskill Metro North station. Every phase of construction was fully permitted, inspected and completed with a final certificate of occupancy. This is a home that offers the quality, efficiency and peace of mind that is associated with new construction, Truly move-in-ready condition, see it today!

16 Wayne Avenue, Fort Montgomery

$325,000

2 Beds ⋅ 1 Baths ⋅ 1033075 MLS

Welcome to this charming Ranch in Fortmongomery NY!!! Offering a flexible layout, hardwood floors, abundant natural light and plenty of potential for its next owner. This home features a comfortable living room, a separate dining area, an eat-in kitchen with stainless-steel appliances, and a full bathroom. A spacious bonus room with a dramatic stone fireplace providing additional living space and access to the backyard; where you can enjoy a private yard with room for gardening, relaxing or outdoor dining & entertaining. The property has served as a rental for more than 20 years, presenting an opportunity for investors, first-time buyers or those looking to personalize a home of their own. Conveniently located near West Point, Woodbury Common Premium Outlets, Harriman State Park, Bear Mountain State Park and the Garrison Metro-North train station, with easy access to shopping, recreation and transportation.

6 Cherry Street, Fort Montgomery

$574,999

5 Beds ⋅ 3 Baths ⋅ 1032620 MLS

An entertainer's dream in the heart of Highland Falls! This five bedroom, three bath home offers space and amenities that are hard to find in this community. Spread across three plus levels, you'll find a home perfect for entertaining, hosting, and everyday living. Step outside to a large deck built for hosting, with a pool and a hot tub pad already wired with electrical situated above on the hillside, plus a spectacular yard with views. The chef's kitchen features a large peninsula, granite counters, and an open layout that flows perfectly for entertaining, complemented by beautiful hardwood floors on the main level. The two car garage plus private driveway offers parking that's tough to find in this area, giving you the space and convenience buyers are looking for. Set on over half an acre, this home also boasts a prime location just minutes from West Point and within easy commuting distance to New York City, whether by car or by rail. Nearby, residents also enjoy access to the adjacent community park. Homes with this much space and these amenities rarely come on the market in Highland Falls, call today before it's gone!

94 Mearns Avenue, Highland Falls

$550,000

4 Beds ⋅ 2 Baths ⋅ 1023994 MLS

Meticulously maintained two-family home - just unpack your bags as this duplex is move-in ready. Great investment or opportunity to live in one unit while generating income in the 2nd unit. First Level Unit offers an open concept living with updated kitchen boasting stainless steel appliances, tiled backsplash, breakfast island overlooking the living room. 2 spacious bedrooms, fully renovated bathroom, and private laundry. The 2nd floor level offers open concept living with vaulted ceilings, updated kitchen boasting stainless steel appliances, tiled backsplash, breakfast island overlooking the living room. 2 spacious bedrooms with vaulted ceilings, fully renovated bathroom and private laundry. Separate electric meters, gas meters and hot water heaters. Recessed lighting, luxury vinyl floors, ductless AC units, vinyl siding, gated parking for 5 cars. Conveniently located near West Point Military Academy and just minutes from the charming Village of Highland Falls, local shops and restaurants. Enjoy Hudson Valley views and nearby hiking and outdoor recreation. Easy commuting location with nearby Route 9W, Palisades Interstate Parkway and Metro-North train stations just a short drive away. Currently generating $4500 in rental income. Taxes T&C $1,735, Village $2,210, School $4,108- Trash included in tax- Annual Water $430(approx.) Annual Sewer$750(approx.).

23 Tobins Lane, Highland Falls

$499,000

5 Beds ⋅ 2 Baths ⋅ 1010893 MLS

Looking for an investment property? This unique multi-family opportunity is located in a charming, established neighborhood within walking distance of both United States Military Academy at West Point and historic downtown Highland Falls. The property features two separate residences, each with its own private entrance, making it an attractive option for investors or owner-occupants seeking rental income. The lower level offers a 3-bedroom unit, while the upper level features a 2-bedroom unit. Conveniently located just 14 minutes (approximately 9.5 miles) from the nearest Metro-North Railroad station and only 13 minutes from Woodbury Common Premium Outlets. Property highlights include: Roof and windows approximately 10 years old Two furnaces (1 of which was installed 18 months ago) Two electric meters Two water heaters Garage Basement Spacious backyard Annual operating expenses include taxes, insurance, sewer, and lawn care. Tenants are responsible for all remaining utilities and expenses. HOUSE BEING SOLD AS IS. Please allow 48 hours' notice for showings to accommodate the current tenants.

7 Sweezy Avenue, Highland Falls

$325,000

1000922 MLS

Tucked away at the end of a quiet cul-de-sac in Fort Montgomery, this 12.5-acre parcel offers a rare opportunity to own a significant piece of land in the Hudson Highlands bordering Bear Mountain State Park. Surrounded by natural beauty and protected parkland, the property provides exceptional privacy and a peaceful wooded setting with dramatic mountain terrain. Whether envisioned as a private estate, multi-generational retreat, or potential development opportunity, the property offers a unique canvas in one of the Hudson Valley’s most scenic locations. Existing access improvements and curb cut appear to already be in place, providing a valuable starting point for future planning. Preliminary due diligence indicates potential for subdivision or other residential development concepts, subject to municipal approvals and buyer verification. Conveniently located near Bear Mountain, West Point, the Hudson River, and major commuter routes, the property combines seclusion with accessibility — a rare combination in today’s market. Buyer to independently verify all zoning, engineering, subdivision potential, and intended uses.

4 Weyant Road, Fort Montgomery

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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.