Highland Mills Homes with Detached Parking features

Welcome to Highland Mills, a picturesque gem nestled in the heart of Orange County, New York. This charming hamlet is part of the Town of Woodbury and is known for its serene landscapes, friendly community, and convenient access to both nature and urban amenities. With its rolling hills and lush greenery, Highland Mills offers a tranquil escape from the hustle and bustle of city life, making it an ideal location for families and individuals seeking a peaceful retreat.

One of the standout features of homes in Highland Mills is the availability of detached parking. This thoughtful addition not only enhances the functionality of your property but also provides added convenience and privacy. Imagine coming home after a long day to find your vehicle securely parked just steps away from your front door, free from the worries of street parking or congestion. Detached garages and parking spaces are perfect for those who value their vehicles or need extra storage for outdoor gear, tools, or recreational equipment.

In addition to its practical amenities, Highland Mills boasts a vibrant community spirit. Residents enjoy a variety of local parks, hiking trails, and recreational activities that celebrate the natural beauty of the area. With its close-knit atmosphere and rich history, Highland Mills is more than just a place to live; it's a community where you can truly feel at home. Whether you're looking for a cozy cottage or a spacious family home, Highland Mills offers a diverse range of properties with the added benefit of detached parking, making it the perfect place to start your next chapter. Come discover the charm of Highland Mills today!

Newest Highland Mills Homes with Detached Parking features

$750,000

3 Beds ⋅ 3 Baths ⋅ 1030855 MLS

Historic Charm. Timeless Character. Endless Possibilities. Steeped in local history and rich with original character, this remarkable 1800s home offers the rare opportunity to own a piece of the past while enjoying the privacy and space today's buyers crave. Nestled on 3.4 picturesque acres, this peaceful property feels like a private country retreat, yet is just a short drive to town, offering a balance of seclusion and convenience. Adding to its unique story, this historic residence was once home to renowned American artist Winslow Homer, the grounds and surrounding landscape inspiring the most recognized work of his Hudson Valley period and giving the property a fascinating connection to one of America's most celebrated painters. From the moment you arrive, the stately farmhouse, inviting wraparound porch, and beautifully landscaped grounds create an unforgettable first impression. Surrounded by towering mature trees, the property is a haven for nature lovers. Throughout the seasons, stunning hydrangeas provide vibrant blooms, a graceful weeping cherry tree welcomes spring with breathtaking color, and the magnificent Persian Silk Tree (Mimosa) is a favorite gathering place for butterflies and hummingbirds, creating a peaceful setting you'll enjoy from the porch or while strolling the grounds. Inside, timeless craftsmanship has been lovingly preserved with oversized windows, elegant millwork, an exquisite carved marble fireplace, and a classic clawfoot soaking tub that reflects the home's rich history and enduring character. Currently recognized as a 3-bedroom home, the spacious and flexible floor plan offers abundant opportunity to create up to five bedrooms, making it ideal for a growing family, multigenerational living, dedicated home offices, guest accommodations, or creative studio space. Whether you're sipping coffee on the wraparound porch, entertaining beneath the shade of mature trees, watching hummingbirds dance through the gardens, or simply enjoying the quiet surroundings, every corner of this property invites you to slow down and appreciate a lifestyle that is increasingly difficult to find. Historic homes offering this combination of architectural character, documented history, beautiful gardens, privacy, acreage, and future potential rarely come to market. Whether you're searching for a forever home, a weekend retreat, or a property with a story worth preserving, this exceptional residence presents a truly rare opportunity. Come experience the history, beauty, and timeless charm for yourself. Some homes are simply places to live. This one is a place to be inspired.

250 Old St Rte 32, Highland Mills

$574,000

3 Beds ⋅ 2 Baths ⋅ 965720 MLS

43 Sunset Terrace | Highland Mills, NY. Offered for the first time in 58 years, this thoughtfully maintained 3-bedroom, 2-bath home sits atop a quiet neighborhood with beautiful mountain views. Carefully cared for through the decades, it offers a special opportunity for a new owner to bring their own style while benefiting from the stewardship and improvements already in place. Natural light fills the main living spaces, where hardwood floors run throughout the main level and expansive windows frame the surrounding landscape. Recent owner updates include the roof, windows, gutters, and generator. Just off the kitchen, a beautiful bluestone patio creates an extension of the living space, ideal for outdoor dining and entertaining. An oversized detached two-car garage is exceptional for vehicles, storage, hobbies, workshop space, or recreational equipment. The lower level expands the home's versatility with two large living rooms, one featuring a wood-burning fireplace. An additional room with a closet and a full bathroom on this level provides flexible space for guests, a home office, a fitness area, or creative pursuits. An oversized mudroom and laundry area with abundant storage adds everyday practicality and helps keep the main living areas organized. Located in the Town of Woodbury and within the Monroe-Woodbury School District, residents also enjoy access to exclusive town amenities, including the John P. Burke Memorial Pool and Earl Reservoir. The property also offers exceptional access to the best of Hudson Valley living, with nearby hiking trails, outdoor recreation, and cultural destinations, including Storm King Art Center. Conveniently located approximately five miles from rail service to New York City, about 51 miles from Midtown Manhattan, seven miles from Storm King Art Center, and six miles from Schunnemunk State Park, the home offers a wonderful balance of natural beauty and commuter accessibility. Additional features include transferable leased solar panels. With its elevated setting, mountain views, flexible living spaces, access to Woodbury's exceptional recreational amenities, and location within the Monroe-Woodbury School District, 43 Sunset Terrace offers a special opportunity to create a home that balances comfort, community, and Hudson Valley living.

43 Sunset Terrace, Highland Mills

$875,000

6 Beds ⋅ 3 Baths ⋅ 1010358 MLS

Explore this great opportunity located at 27 Van Tassel in Highland Mills, offering an impressive 2.6-acre property with expansive grounds, privacy, and a peaceful, calm setting. This beautiful home spans 3,058 square feet and is filled with rich features and amenities designed for both comfort and everyday living. As you enter, you are welcomed by an elegant formal dining room and a spacious kitchen, along with a separate dining nook that creates the perfect space for relaxed meals and gatherings. The home includes 6 well-appointed bedrooms, 3 bathrooms, a laundry room and a double vanity that adds both convenience and style. Additionally the house includes a beautifully airy sunroom filled with natural light to enjoy nature! The roof is brand new as of year 2024. Outside, the property truly shines with its beautifully maintained grassy backyard and two comfortable patios, providing ideal spaces for entertaining, outdoor dining, or simply enjoying the serene surroundings and a natural pond beside the house, offering a peaceful place to enjoy nature. Besides for the attached garage, this property also offers a detached carport and a 14x16 shed for added storage. This property offers the perfect blend of space, privacy, and charm in a highly desirable setting. Don't miss this great opportunity! Schedule your showing today, to make this home yours!

27 Van Tassel Court, Highland Mills

$175,000

1 Beds ⋅ 1 Baths ⋅ 952623 MLS

Tucked away on a private road in the Town of Cornwall, this charming 600 sq ft cottage offers the perfect blend of privacy, tranquility, and convenience. Whether you’re seeking a full-time residence or a peaceful weekend getaway, this home delivers mountain views and a secluded setting that feels like a true escape. The interior features a spacious living room with large window overlooking the backyard, a convenient kitchen, and a flexible layout offering 1–2 bedrooms plus an office—ideal for remote work or guest space. A full bath completes the main level, while the unfinished basement provides abundant storage options. Significant mechanical updates include a new furnace (January 2025), newer hot water heater (2022), well pressure tank (2020), updated electric with a new electric meter, and two 275-gallon oil tanks, offering peace of mind for years to come. Located in the highly sought-after Cornwall School District, this home is just minutes from the train station, I-87, restaurants, shops, and everyday conveniences—making it as practical as it is peaceful. A rare opportunity to enjoy privacy, mountain views, and easy commuter access in one of Cornwall’s most desirable locations. (Home needs a new septic tank. Selling as is.)

36 Paradise Hill, Highland Mills

$1,040,000

5 Beds ⋅ 4 Baths ⋅ 900348 MLS

237 Mineral Springs Rd, Highland Mills, NY 10930 – 5,700 sq ft | 5 Beds | 3.5 Baths | 2.5 Acres | Cornwall Central School District Exceptional 5,700 sq ft colonial on 2.5 landscaped acres, less than one hour from NYC. Located in the Cornwall Central School District, this home offers high-end finishes, vaulted ceilings, and extensive indoor/outdoor entertaining spaces. Interior Features: • Chef’s kitchen with Viking stove and custom cabinetry • Indoor brick pizza oven • Vaulted ceilings in main living areas • Huge primary suite with 2 walk-in closets and master bath • Multiple fireplaces • Home gym • Entertainment/media room • Sunroom with mountain views • Central air conditioning • Whole-house water filtration with built-in UV light (artesian well) Exterior Features: • 2.5 private acres • Blue stone patio with built-in outdoor kitchen and fire pit • 4-car garage (3 detached + 1 attached) • Barn/workshop • Chicken coop • Backup generator Location: Minutes to I-87, Route 32, and Woodbury Commons. Close to parks, wineries, Storm King Art Center, and Hudson Valley attractions.

237 Mineral Springs Road, Highland Mills

Start Your Search

© 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.

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.