Highland Mills Real Estate

Welcome to Highland Mills, a charming hamlet nestled in the heart of Orange County, New York. This picturesque community is part of the Town of Woodbury and offers a serene escape from the hustle and bustle of city life while still being conveniently located just a short drive from New York City. Surrounded by the breathtaking beauty of the Hudson Valley, Highland Mills is known for its stunning landscapes, friendly atmosphere, and rich history.

One of the most appealing aspects of Highland Mills is its strong sense of community. Residents take pride in their neighborhood, fostering a welcoming environment where families can thrive. The hamlet is home to a variety of local businesses, parks, and recreational facilities, providing ample opportunities for outdoor activities, such as hiking, biking, and picnicking. The nearby Bear Mountain State Park and Harriman State Park offer endless trails and natural beauty, perfect for nature enthusiasts.

Highland Mills also boasts a selection of excellent schools, making it an ideal location for families looking to settle down in a nurturing environment. The area is well-connected, with easy access to major highways and public transportation, ensuring that commuting to nearby cities is a breeze.

With its blend of quaint charm, vibrant community spirit, and natural beauty, Highland Mills is a hidden gem in Orange County. Whether you're seeking a peaceful retreat or a place to raise a family, this delightful hamlet has something for everyone. Discover the warmth of Highland Mills and make it your new home today!

Newest Listings in Highland Mills

$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

$749,000

4 Beds ⋅ 3 Baths ⋅ 1032361 MLS

CLASSIC COLONIAL on a cul de sac, and in the dramatic shadows of the Schunnemunk Mountains & State Park (the highest peaks in Orange County) -- oh those views! Built in 2008, this 2,926 square foot stunner features curb appeal galore with a classic wraparound front porch, along with 4 bedrooms, a fenced in backyard with an above-ground pool, and a full unfinished walk-out basement which must be seen to be truly appreciated! . . . . . . Cornwall School District! . . . . . . AND ON 3.3 LEVEL ACRES, which is a mixture of a wide-open backyard space beyond the fenced in portion, in addition to an awesome wooded area in the back of the property which ends at the Woodbury Creek, and includes bucolic & peaceful trails for walking, quads, etc.! . . . . . . Enter to foyer area with soaring 18 foot ceilings, while main floor also features a formal living room, open floor plan family room with gas fireplace and leading into breakfast nook & chef's kitchen with all the bells & whistles, and oversized formal dining room with gorgeous bay windows . . . . . . UPSTAIRS is highlighted by the primary en suite featuring more bay windows, a separate sitting area leading into a huge walk-in closet, and a primary bathroom with dual sinks, soaking tub and shower. Washer/dryer on second floor. NEW hot water heater. Central AC handler in attic just 2 years old. There's also a FULL HOUSE GENERATOR . . . . . . On a publicly-maintained cul de sac with just two other homes, and walk next door to Sweet Clover Farm (the former Palaia Winery), which features a distillery & tasting room, food, live music & a Sunday Farmer's Market, among other offerings! . . . . . . Fantastic commuter spot just minutes to the New York State Thruway, commuter train into Manhattan, bus -- also minutes to renowned Woodbury Commons Shopping Outlets, as well as everything else this wonderful area has to offer!

7 Seaman Court, Highland Mills

$440,000

3 Beds ⋅ 2 Baths ⋅ 1031034 MLS

Welcome to this charming single-family retreat set on a breathtaking, park-like lot surrounded by mature trees and lush, vibrant greenery. Inside, the home is bright, neutral, and move-in ready. Hardwood floors flow throughout, catching the natural light that pours in from generous windows in every room. The formal dining room is a true standout — featuring elegant crown molding and a graceful curved bay window it's the perfect setting for everything from weeknight dinners to holiday gatherings. Three large windows frame gorgeous views of the lush backyard, bringing the outdoors in. The kitchen is both functional and full of character, offering granite countertops, natural oak cabinetry, stainless steel appliances, and a large picture window overlooking the serene, tree-lined yard. Spacious bedrooms continue the home's warm, comfortable feel — hardwood floors, abundant natural light, generous closet space, and a versatile layout. Outside, the expansive grassy lot is truly the crown jewel. Mature trees provide shade, privacy, and a peaceful, retreat-like atmosphere that's rare to find. A charming wooden arbor, additional outbuilding for storage or a workshop, and a paved driveway round out this exceptional property. Homes this special don't stay on the market long. Schedule your private tour today — you'll fall in love the moment you pull up.

10 Park Avenue, Highland Mills

$524,999

4 Beds ⋅ 2 Baths ⋅ 1030332 MLS

Welcome to this beautifully renovated raised ranch nestled on a picturesque 1/2 acre lot in the highly desirable community of Highland Mills! Offering 1,528 square feet of thoughtfully updated living space, this move-in ready home combines modern comfort with timeless appeal. Step inside and discover a bright, inviting interior featuring 4 spacious bedrooms and 1.5 bathrooms, providing plenty of room for loved ones, or a dedicated home office. Recent renovations give this home a fresh, contemporary feel, allowing you to move in and start enjoying it from day one. Outside, the generous half-acre lot offers endless possibilities—from summer barbecues and outdoor entertaining to gardening, play areas, or simply relaxing while surrounded by mature trees that provide beauty and privacy. Conveniently located near shopping, restaurants, parks, major commuter routes, and everything the Hudson Valley has to offer, this home delivers the perfect balance of peaceful suburban living and everyday convenience. Whether you're searching for your first home, need more space for a growing family, or simply want a beautifully updated property in a sought-after location, this Highland Mills gem checks all the boxes. Don't miss your opportunity to make this exceptional home your own—schedule your private showing today before it's gone!

246 Skyline Drive, Highland Mills

$999,998

5 Beds ⋅ 4 Baths ⋅ 1029095 MLS

Welcome to 190 Ridge Road in the heart of Highland Mills! Nestled on a beautiful 1-acre lot in the highly sought-after Monroe-Woodbury School District, this spacious 4-bedroom, 3.5-bath split-level home offers over 2,500 square feet of comfortable living space designed for both everyday living and entertaining. Step inside to discover an inviting open floor plan featuring cathedral and high ceilings, a stunning kitchen with a center island, granite countertops, stainless steel appliances, pantry, and eat-in dining area. The formal dining room and bright living spaces provide the perfect setting for gatherings with family and friends. The primary suite offers a private retreat with a walk-in closet and en-suite bath featuring a double vanity and soaking tub. A versatile office can easily serve as a fifth bedroom, guest room, or sitting room. The entry level features a formal living room with a masonry fireplace and pellet stove, ideal for relaxing on cool evenings. There is a huge family room on the lower level - great for entertaining or hanging with the family and friends! Additional features include central air, recessed lighting, ceiling fans, skylights, abundant storage, and a spacious laundry room. Enjoy the community town pool located in Central Valley or the "Rez" located within walking distance. Outside, your backyard oasis awaits! Spend summers enjoying the in-ground pool, while the expansive yard provides plenty of room for entertaining, gardening, or simply enjoying the peaceful surroundings. Watch the fireworks from your deck when the "Rez" Celebrates 4th of July! An oversized garage and private driveway offer ample parking and storage. Conveniently located just minutes from major highways, shopping, parks, and schools, this home combines privacy with everyday convenience. Don’t miss the opportunity to make this exceptional Highland Mills property your forever home!

190 Ridge Road, Highland Mills

$459,000

3 Beds ⋅ 3 Baths ⋅ 1018634 MLS

Welcome to this beautifully maintained end-unit townhome in the desirable Timber Ridge community. Featuring 3 bedrooms, 3 full baths and a finished basement. The gorgeous, updated stairs is the first thing you notice as you walk up to this great home and you will be WOWed from there! **Thoughtfully designed layout, eat-in kitchen with SS appliances and charming banquette seating, dedicated dining room, beautiful hardwood floors, custom doors, living room with vaulted ceilings and skylights as well as a cozy fireplace and a private patio**are just some features that impress as soon as you enter. Upstairs you will fall in love with the bright landing, extra deep closet, a bonus room as well as a very large bedroom with full bath. The finished basement offers lots of storage, an additional room that lends itself perfectly for a media room and a 2 car garage. Owning this home gives you access to the community pool and newly renovated playground as well as town amenities that include "The Rez" lake and the J.Burk town pool. Great commuter location near bus stops, major highways, Woodbury Commons, dining and Monroe Woodbury schools. ** Improvements: Roof replaced in March 2022; Water Heater Jan 2026; Kitchen Appliances Jan 2023**

15 Ash Court, Highland Mills

$498,000

3 Beds ⋅ 3 Baths ⋅ 1027087 MLS

Nestled on a quiet cul-de-sac, this beautifully maintained townhome offers spacious rooms, thoughtful details, and a wonderful townhome community setting. The open plan living and dining room combination features a marble gas fireplace, wood floors and walls of windows. The eat-in kitchen provides abundant counter space; sliding glass doors leading out to the enormous Trex deck make three seasons entertaining easy. Upstairs, the primary bedroom suite features 9-foot ceilings, a lovely palladian window, en suite private bath, and walk-in closet. Two additional bedrooms offer generous double closets, and the hall bath serves both. A finished lower level family room adds great additional space and is currently used as a music studio. The two car garage has added built in storage plus a custom closet was added under the stairs. Over $80k of improvements in the past few years include renovated kitchen with granite/stainless/new backsplash, water softener, new roof, new widened driveway (2025) with Belgian block and parking for 2+ additional cars. Enjoy a community filled with activities for family and friends, including scenic walking trails, lake access with a sandy beach, and a peaceful country feel, all while remaining close to shopping, dining, and conveniences, including the destination mecca Woodbury Common. Commuting to NYC is easy by train or bus. Taxes with STAR approximately $9,919.

1 Ledger View Court, Highland Mills

$999,000

1025743 MLS

Rare mixed-use opportunity in the heart of Highland Mills with outstanding visibility along Route 32. This beautifully maintained two-story property offers approximately 2,750 square feet of flexible space, a detached two-car garage and/or workshop, approximately 17 parking spaces, public water and sewer, and excellent potential for an owner-user or investor. The approximately 1,300-square-foot first floor is currently configured as professional office space featuring a welcoming waiting room, reception area, private office, half bathroom, kitchen and breakroom. Large windows provide abundant natural light, while an accessibility ramp offers added convenience. The approximately 1,450-square-foot second floor features a fully renovated two-bedroom, one-bath apartment with high ceilings, oversized custom windows and a bright, open layout. The spacious kitchen includes quartz countertops, stainless steel appliances, recessed lighting and under-cabinet lighting. The kitchen opens directly to a Trex deck with vinyl railings and an electric awning overlooking the fenced backyard. A comfortable family room, two well-proportioned bedrooms and a full bathroom complete the residence. The building underwent extensive renovations in 2018, including a whole-building generator, irrigation system, upgraded electrical, substantial plumbing improvements, a new water heater and two heating and air-conditioning systems, with one serving each floor. The second-floor apartment was also fully renovated at that time. Additional features include basement and attic storage, French drains and a sump system installed in 2006, one electric meter, two gas meters and a landscaped exterior with decorative stonework. The detached garage and workshop is heated and cooled and includes a dedicated 220-volt outlet, making it ideal for a contractor, tradesperson, hobbyist or additional workspace. Conveniently located near major highways, Woodbury Common Premium Outlets, local businesses, offices and residential neighborhoods. Rent the spaces separately, occupy one floor while generating income from the other, or explore combining the property for a larger commercial operation. A versatile and highly visible property offering professional space, residential accommodations and exceptional owner-user potential.

531 State Route 32, Highland Mills

$925,000

4 Beds ⋅ 3 Baths ⋅ 1023811 MLS

Luxury, comfort, and exceptional craftsmanship define this stunning four-bedroom Center Hall Colonial. Thoughtfully designed with superior craftsmanship and premium finishes throughout, this impressive residence offers the perfect blend of sophistication, comfort, and functionality for the discerning buyer. At the heart of the home is a spectacular custom chef's kitchen featuring Travertine marble flooring, handcrafted cabinetry, a center island, Wolf built-in oven with warming drawer, Wolf microwave/convection oven, Sub-Zero refrigerator, Thermador induction cooktop, and Miele dishwasher—an extraordinary space designed for everyday living and effortless entertaining. The sun-filled living and dining rooms offer an elegant setting for both formal gatherings and everyday enjoyment. The inviting great room features soaring cathedral ceilings, a custom cherry built-in entertainment wall with surround sound, and seamless access to the backyard, where the outdoor amenities are second to none. Step outside to your own private backyard oasis featuring a stunning Cypress pergola, elegant stone patio, heated saltwater in-ground pool with exposed aggregate decking, and a separate hot tub. Weather entertaining guests or enjoying a peaceful evening under the stars, this exceptional outdoor living space is designed for year-round enjoyment. Additional highlights include a distinctive stucco front exterior with a covered front porch, an oversized three-car garage, two large storage sheds, and generously sized secondary bedrooms, each with dedicated study or play areas. The finished basement provides substantial additional living and entertaining space and is not included in the home's reported square footage, adding exceptional value and versatility. Also close to West Point, Woodbury Commons, Wineries, Hiking Trails, NYC transportation and with Woodbury Recreation access. From its exceptional craftsmanship to its resort-style outdoor amenities, every detail of this remarkable home reflects quality, elegance, and pride of ownership. A rare opportunity to own a residence of this caliber—one you won't want to miss.

10 Sutherland Drive, Highland Mills

$795,000

4 Beds ⋅ 3 Baths ⋅ 1023481 MLS

Welcome to this Custom Colonial offering almost 3,100 finished SQFT of beautifully designed living space perched up on a hill in Timber Crest Estates, an enclave of 15 homes in the heart of Highland Mills, town of Woodbury. This 4-bedroom, 3-full bath home features an open and inviting layout with 9-foot ceilings, freshly painted throughout, hardwood floors, and an abundance of natural light from oversized windows throughout. The main level offers a spacious eat-in kitchen with stainless steel appliances, a formal dining room, a dedicated office/den, and a full bath, providing flexibility for guests or multigenerational living. The dramatic two-story great room is the heart of the home, centered around a cozy gas fireplace, while sliding doors off the kitchen lead to a deck overlooking the backyard—perfect for outdoor dining and entertaining. Upstairs, the expansive primary suite serves as a private retreat with tray ceilings, a large walk-in closet and an ensuite bath featuring a Jacuzzi tub. Three additional generously sized bedrooms and a full hall bath complete the second level. The full unfinished walk-out basement offers endless possibilities for future finished living space, a home gym, or recreation area. Additional highlights include municipal water, sewer, and natural gas, as well as owned solar panels for increased energy efficiency and cost free electric! This exceptional home combines space, comfort, and convenience in one outstanding total package. This will not last, PRICED TO SELL!

5 Sherwood Court, Highland Mills

$535,000

3 Beds ⋅ 3 Baths ⋅ 1020871 MLS

….. Desperate Seller – Bring All Offers!! The seller is highly motivated and ready to make a deal! Don't miss this opportunity. Submit all offers—every offer will be presented and considered. Welcome to this beautifully updated home offering the perfect blend of modern style, comfort, and functionality. Set on a spacious property in the heart of Highland Mills, this move-in-ready home features an open-concept layout with abundant natural light, creating a warm and inviting atmosphere. The stunning renovated kitchen is the centerpiece of the home, showcasing elegant wood cabinetry, beautiful stone countertops, stainless steel appliances, ample cabinet space, and a large peninsula that's perfect for everyday living and entertaining. The kitchen flows seamlessly into the dining and living areas, making gatherings effortless. The home offers generously sized bedrooms, updated bathrooms, hardwood and ceramic flooring, and a flexible lower level that provides additional living space ideal for a family room, home office, gym, playroom, or guest area. A charming stone fireplace adds warmth and character to the lower level. Outside, enjoy a level backyard with a brick patio, perfect for outdoor dining, relaxing, or entertaining. The oversized driveway and attached garage provide plenty of parking and storage. Conveniently located just minutes from Woodbury Common Premium Outlets, major highways, parks, schools, restaurants, and public transportation, this home offers an easy commute while maintaining a peaceful suburban setting. Property Highlights: Beautifully updated throughout Spacious open-concept living Renovated kitchen with stone countertops and stainless steel appliances wood cabinetry with abundant storage Flexible finished lower level with stone fireplace Large driveway and attached garage Brick patio and spacious backyard Convenient Orange County location near shopping, dining, and major commuter routes Move right in and enjoy everything this exceptional Highland Mills home has to offer! Schedule a showing!

249 Ridge Road, Highland Mills

$649,000

4 Beds ⋅ 3 Baths ⋅ 1005912 MLS

4 Sequoia Trail is a beautifully renovated 2,004 sq ft residence that seamlessly blends comfort, style, and convenience. Set on landscaped grounds with plenty of outdoor space, it offers a peaceful retreat while being near local attractions. The bright living room, featuring oversized windows and an elegant fireplace, flows into a delightful dinette area. The kitchen boasts contemporary cabinetry and a spacious deck for entertaining. The home includes four bedrooms with great storage, two modernized bathrooms, and a finished basement providing extra living space. A two-car garage and a well-kept yard round out this move-in-ready property, ideal for modern living.

4 Sequoia Trail, Highland Mills

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