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$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
$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
$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
$999,000
4 Beds ⋅ 3 Baths ⋅ 1012714 MLS
Spacious Colonial situated on a beautiful private lot featuring oversized bedrooms, updated baths, and a bright open floor plan. The impressive primary suite includes a spa-like bathroom, while multiple living areas provide flexibility for today's lifestyle. Enjoy a large deck, patio, expansive yard, and peaceful surroundings. Conveniently located near shopping, schools, parks, and major commuter routes. A wonderful opportunity to own a move-in-ready home with space both inside and out.

14 Apple Hill Drive, Highland Mills
$899,000
4 Beds ⋅ 3 Baths ⋅ 996875 MLS
Beautifully maintained and thoughtfully updated, this exceptional home is set on professionally landscaped grounds with outstanding curb appeal and a resort-style backyard designed for both relaxation and entertaining. The inviting interior features a grand entry foyer, a stunning chef's kitchen with custom cabinetry, granite countertops, and stainless steel appliances, along with spacious living and dining areas ideal for everyday living and gatherings alike. Generously sized bedrooms and versatile living spaces provide comfort and flexibility throughout. Step outside to your own private retreat, complete with a sparkling in-ground pool, cascading waterfall, expansive deck, hot tub, and beautifully manicured grounds surrounded by mature trees. Meticulously cared for inside and out, this move-in-ready property offers the perfect balance of elegance, comfort, privacy, and outdoor living. A truly special home that must be seen to be fully appreciated.

11 Country Hollow, Highland Mills
$675,000
3 Beds ⋅ 3 Baths ⋅ 1011652 MLS
Welcome to the Prestigious Brigadoon Community in Highland Mills. Discover the perfect blend of style, space, and serenity in this contemporary gem, ideally situated at the end of a quiet cul-de-sac in the highly sought-after Brigadoon community. Located within the Monroe-Woodbury School District, this bright and beautiful home offers comfort and breathtaking mountain views throughout. The main level features a spacious primary suite with his-and-her closets and vaulted ceilings that flood the space with natural light. A large bonus room adds valuable flexibility, perfect as a home office, playroom, or media space. The airy, open floor plan includes a dramatic two-story living room with a modern flair and a cozy fireplace, creating a warm and inviting atmosphere. The open floor plan kitchen is outfitted with granite countertops and stainless-steel appliances, ideal for both everyday living and entertaining. Upstairs, generously sized guest bedrooms feature ample closet space, with a walk-up attic offering even more storage potential. There's also a walk-out basement—complete with windows and a door—ready to be finished to suit your needs. Enjoy outdoor living at its finest with a picture-perfect covered front porch, mature landscaping on your .34 acres, and a spacious back deck with sweeping mountain views. Additional highlights include a two-car garage, and the central air condenser was replaced just two years ago. Priced to sell quickly, this home is a rare opportunity in one of Highland Mills' most desirable neighborhoods. Besides having your own community Pool and playground, the Town of Woodbury offers a Lake/Res for summer camp, swimming, boating, fishing, a Gorgeous Town Pool Facility where you can enjoy Residents of Woodbury Only Summer Fun!!! Playground etc. Take a ride to see what Woodbury has to offer its residents.

7 Paisley Court, Highland Mills
$699,000
4 Beds ⋅ 3 Baths ⋅ 1015588 MLS
Welcome home to this bright, beautifully maintained colonial tucked into a quiet corner of Brigadoon. A welcoming foyer leads into an open, airy main floor with gleaming hardwood floors throughout. The formal dining room connects to the kitchen via a convenient butler's pantry, perfect for entertaining, while the living room centers around a cozy fireplace for those cooler months. A flexible main floor room offers space for a home office or whatever suits your needs, and the main floor laundry connects directly to the 2-car garage for everyday convenience. Upstairs, the spacious primary suite impresses with two walk-in closets and a beautifully renovated master shower, joined by three additional well-sized bedrooms and a full bath. The walk-out basement adds valuable extra living area, and the private yard backs up to a peaceful, wooded view, all on a low-traffic circular street that's ideal for kids and quiet evenings alike. Residents enjoy community amenities including a pool, tennis courts, and playground, plus easy access to Woodbury's parks, beaches, and reservoir. With NYC transportation, Woodbury Common, and West Point all just minutes away, this home offers the perfect balance of comfort, space, and convenience.

5 Oldwyck Crescent, Highland Mills
$785,000
5 Beds ⋅ 5 Baths ⋅ 1012601 MLS
Discover this exceptional luxury residence located in a highly sought-after neighborhood. This one-of-a-kind property offers an expansive layout designed for comfortable living and entertainment. The home features a magnificent kitchen with elegant granite countertops and a family room characterized by cathedral ceilings and a fireplace. The residence includes five generously sized bedrooms and five bathrooms. Notably, the primary suite features a whirlpool tub, while an additional upstairs bedroom also included an ensuite full bathroom. Furthermore, the ground level contains a mother-in-law suite complete with a kitchenette, dinette, and full bath. The exterior serves as a private oasis, featuring a heated inground pool, a paver patio, and meticulously landscaped front and back yards. Additional amenities include central air conditioning and a beautiful, private setting conveniently located just minutes from Woodbury Common and transportation to New York City. Don't miss out, schedule your showing today!

1 Cindy Lane, 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
$379,900
3 Beds ⋅ 2 Baths ⋅ 1002400 MLS
Welcome to this spacious 3-bedroom, 2-bath townhouse in the desirable Timber Ridge Community of Highland Mills, located within the Monroe-Woodbury School District. This home combines comfortable interior living, valuable updates, and access to an impressive collection of community amenities. Buyers searching for a townhouse with a finished basement, home with a walk-in closet, property with a deck, or townhome near commuter transportation will appreciate everything this home has to offer. The main level features an open-concept living and dining area with updated flooring, recessed lighting, and a functional layout designed for everyday living and entertaining. Sliding glass doors lead to a private deck surrounded by mature trees, creating an inviting outdoor space to relax, dine outdoors, or enjoy the natural wooded setting. The spacious primary suite offers a walk-in closet and direct access to a full bath, while two additional bedrooms provide flexibility for guests, a home office, or other household needs. The finished lower level expands the living space with the third bedroom, a large recreation room that can serve as a media room, fitness area, playroom, home office, or multi-purpose gathering space, and laundry room. An expansive unfinished storage area offers excellent room for seasonal items, hobbies, workshop space, or future customization. Residents enjoy Timber Ridge's private community amenities, including a pool, tennis and basketball courts, playground, and recreational areas, as well as access to the Town of Woodbury's resident-only recreation facilities featuring beach and lake access at Earl Reservoir, the John P. Burke Memorial Pool, sports fields, walking trails, and more. Conveniently located near shopping, parks, schools, train service, and major commuter routes, this property offers an exceptional opportunity to enjoy the Highland Mills lifestyle.

2 Acorn Court, Highland Mills
$599,999
4 Beds ⋅ 2 Baths ⋅ 1006054 MLS
Welcome to 5 Columbia Circle, a turn-key raised ranch tucked inside the gated Highland Lake Estates community in Highland Mills. From the moment you arrive, this home delivers what most listings only promise: modern updates, real peace of mind, and a backyard that earns its keep. Four bedrooms plus an office/den give you room to live and work without compromise. Two full bathrooms, California Closets in every upstairs bedroom, Pella doors, and Andersen 400 Series windows reflect a home maintained with discipline, not shortcuts. The mechanicals back it up: hot water heater (2021), whole-house water softener and filtration system (2023), and an upgraded back deck (2019) built for those gorgeous Hudson Valley sunsets. Comfort and security are handled. A heated garage with its own thermostat means projects don't stop in January. A central-station monitoring system covers fire, burglary, low-temperature, and carbon monoxide, plus camera coverage for complete confidence. The fenced backyard and lawn sprinkler system round out a property that's genuinely move-in ready. Location is the quiet advantage here. The Metro-North Harriman station sits under 10 minutes away, with NYC roughly 50 miles and about an hour out via I-87 and Route 17. Woodbury Common Premium Outlets, grocery, and everyday essentials are a short drive down Route 32. Weekends open up fast: Harriman State Park and Bear Mountain for hiking, nearby golf, and local wineries and farms that make Orange County living what it is. This is the rare home where the big ticket items are already done and done right. All that's left is to move in, relax and watch the sun go down right off your back deck.

5 Columbia Circle, Highland Mills
$819,000
5 Beds ⋅ 3 Baths ⋅ 1004118 MLS
On Zillow the virtual 3D tour you can find it by facts and features, 8 Allaway Crescent - 4,231 SQ FT + Full Unfinished Basement 4,231 SQ FT + Full Unfinished Basement | 5 Bedrooms Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath | Mountain Views, Welcome to 8 Alloway Crescent. This 4,231 square foot home offers functional layout and impressive scale, plus a full unfinished basement ready for your vision. Main Level You enter through a big, wide foyer with hardwood flooring extending throughout the main level. Dining Room: To the right of the foyer is a big dining room with ample space for entertaining. Living Room: To the left of the foyer is a nice, big living room, well suited for formal seating or quiet conversation. Family Room: The beautiful big family room is open to the kitchen and open to the dinette area, accommodating large furniture arrangements and everyday living. Dinette: Adjacent to the kitchen, there is beautiful space for a dinette with room to put a table. This area has a walkout to the deck and access to the beautiful views. Kitchen: The big kitchen features a large center island, marble countertops, two sinks, abundant cabinetry, and stainless steel appliances. The layout flows directly into the family room and dinette for ease of daily use and hosting. Main Floor Bedroom & Full Bath: The main level includes a den or bedroom plus a full bathroom. This provides flexibility for guests, a home office, or multi-generational living. Garage & Views: A two-car garage is accessed from the main level. Beautiful scenery and views are visible from multiple rooms. Second Level Primary Suite: The master bedroom features a cathedral ceiling and beautiful mountain views. The en-suite bathroom includes a combined soaking tub with jetted jacuzzi, dual vanities, and a stall shower. A walk-in closet is included. The second bedroom is connected to the master with open doors. This layout works well as a baby room, office, or additional bedroom. The third bedroom is a nice size bedroom with closet space. The fourth bedroom is a nice size bedroom with closet space. Fifth Bedroom / Bonus Room: functions as a bonus room and provides additional flexibility for use as a bedroom, playroom, or media room. Laundry is located upstairs for convenience, near the bedrooms. Hall Bathroom: A full hall bathroom serves the additional bedrooms. Additional Levels Walk-Up Attic: A finished walk-up attic is accessed from the second floor and includes a window. The space is suitable for storage, studio, or playroom use. The home includes a full unfinished basement ready for future build-out. Key Specifications: 4,231 Sq Ft Above Grade | Full Unfinished Basement | 6 Total Bedrooms, 5 Upstairs | Upstairs Laundry | Main Floor Bedroom + Full Bath |2-Car Garage | Cathedral Ceiling in Primary | Walk-Up Attic with Window | Mountain Views

8 Alloway Crescent, Highland Mills
$599,000
3 Beds ⋅ 3 Baths ⋅ 1005423 MLS
I am pleased to share the details for this immaculate, move-in-ready home in the Cornwall School District. The bright, open-concept layout features a sun-drenched living room and a sunken formal dining room with vaulted ceilings, both offering deck access. The updated kitchen includes granite countertops, stainless appliances, and a center island. The main level provides two bedrooms and a full bath, while the upstairs primary suite offers a walk-in closet and a luxury en-suite with a Jacuzzi tub. The finished lower level adds 1,182 square feet of living space, including a recreation area, flex room, and full bathroom. Recent upgrades include a new HVAC system, hot water heater, and oil tank. The property features a private deck, brick patio, level yard and a Mobile Charging Port for Electric Vehicles for easy convenience. Access to Woodbury Reservoir and community pool amenities.

29 Olympus Road, Highland Mills
$675,000
4 Beds ⋅ 3 Baths ⋅ 1004321 MLS
Experience the perfect blend of modern elegance and suburban tranquility in this beautiful Colonial, perfectly positioned on 1.2 acres of manicured grounds. Inside, rich hardwood floors and walls of windows create an airy, light-filled atmosphere. The heart of the home is the efficiently designed kitchen, boasting a breakfast bar, pantry and stainless-steel appliances. It flows seamlessly into both a large family room and a spacious composite deck overlooking your private backyard—ideal for summer BBQs. For formal gatherings, the sophisticated living and dining rooms with crown molding and wainscotting provide a serene backdrop for entertaining. Upstairs, the primary suite serves as a peaceful retreat, complete with a walk-in closet and a double-sink vanity. The additional bedrooms are generously scaled for sleep, study, or play. These bedrooms share a hall bathroom with marble countertops. As an exclusive bonus, residents enjoy premium access to the Woodbury Pool and The Earl Reservoir. Minutes from shopping, schools, and commuter transit.

33 Sutherland Drive, Highland Mills
$895,000
4 Beds ⋅ 4 Baths ⋅ 997814 MLS
Welcome to this beautifully maintained Colonial located in the highly desirable Brigadoon neighborhood, perfectly situated on a quiet cul-de-sac and set on 1.9 private acres. This spacious and move-in-ready home offers 4 bedrooms, 3.5 bathrooms, and an ideal layout for both everyday living and entertaining. The main level features a stunning great room, formal living room, cozy family room, private office, and an expansive eat-in kitchen complete with granite countertops, cherry wood cabinets and flooring, stainless steel appliances, center island, and a convenient butler’s service area. Step outside to your own backyard retreat featuring two decks and a beautiful paver patio — perfect for entertaining or enjoying peaceful outdoor living. Additional highlights include crown molding throughout, a newly renovated finished basement ideal for gatherings or recreation, security system, sprinkler system, two-car garage, and ample street parking. Combining space, comfort, and an unbeatable location, this exceptional home is truly a must-see.

3 Braemar Way, Highland Mills
$689,999
3 Beds ⋅ 3 Baths ⋅ 1002671 MLS
Set against a picturesque one acre property with peaceful views of Woodbury Creek, this stunning modern stucco raised ranch offers the perfect blend of space, style, and comfort in the desirable Cornwall School District. With over 2,800 square feet of thoughtfully designed living space, this exceptional home features 3 bedrooms, 3 full bathrooms, vaulted ceilings, and an abundance of natural light throughout. Step inside to discover gleaming hardwood floors, plush carpeting in the bedrooms, with grand cathedral ceilings in the primary bedroom, relaxing jetted soaking tub and a spacious living room, complete with a custom built-in fireplace and charming window seats, creating a warm and inviting atmosphere ideal for everyday living and entertaining. The updated kitchen is a true centerpiece with granite countertops, stainless steel appliances, a wall oven, pantry, and a large island with built-in storage. The lower level offers incredible versatility with a cozy pellet stove, a full bathroom, and a bonus space ideal for a home office, gym, playroom, or recreational area. Additional highlights include updated central air, ample closet space throughout, and a fully updated septic system completed in 2023. Outdoors, enjoy a double deck overlooking the partially fenced yard, retaining walls, and an enclosed above-ground pool, perfect for entertaining, relaxing, or taking in the peaceful creek views. This property also offers exceptional practicality with a two car garage, oversized driveway, carport, generator, and owned solar panels for added energy efficiency and peace of mind. Perfectly situated for commuting, this home is just minutes from Routes 9W, 17, I-84, and I-87, approximately 60 miles to NYC, and conveniently close to the Beacon Bridge, NJ Transit, and Metro-North. A rare opportunity to own a spacious, move-in-ready home in one of Orange County’s most convenient locations. Schedule your showing today!

1649 State Route 32, Highland Mills
$649,990
4 Beds ⋅ 3 Baths ⋅ 1000710 MLS
Welcome to 95 Pine Hill Rd. in Highland Mills, NY! This spacious 4-bedroom, 2.5-bath Colonial is located in a highly sought after area offers the perfect blend of comfort, convenience, and outdoor enjoyment. The kitchen features granite countertops, stainless steel appliances, and plenty of cabinet space, making it ideal for everyday living and entertaining. Enjoy summer days in your private backyard oasis complete with an inground pool. Conveniently located close to shopping, major highways including I-87, and just minutes to Woodbury Common Premium Outlets, this home is perfect for commuters and anyone looking to enjoy all the Hudson Valley has to offer. Don’t miss this opportunity to own a beautiful home in a prime location.

95 Pine Hill Road, Highland Mills
$349,900
3 Beds ⋅ 2 Baths ⋅ 997661 MLS
Welcome to this charming corner-lot townhome in the desirable Town of Woodbury! This spacious 3-bedroom, 2-full-bath home offers the perfect blend of comfort, convenience, and style. The bright and inviting living area features a semi-open layout ideal for both everyday living and entertaining. The kitchen offers plenty of counter space and cabinetry, while the dining area flows seamlessly to the outdoors—perfect for summer gatherings or relaxing evenings. The primary bedroom suite provides a peaceful retreat with its own full bath, and two additional bedrooms offer flexibility for guests, a home office, or hobby space. Situated on a corner lot, the home enjoys extra yard space and added privacy. Located in a prime area of Woodbury, you’ll have access to the Woodbury Recreation facilities, Monroe-Woodbury schools, and an easy commute via major highways, shopping, and restaurants just minutes away. Don’t miss this opportunity to own a beautiful, well-maintained townhome in one of Orange County’s most sought-after communities!

30 Sycamore Court, Highland Mills
$11,000,000
16 Beds ⋅ 16 Baths ⋅ 974021 MLS
R1A zoned, R3A zoned, agriculture zone approved, infinity pool, tennis and basketball court, gazebo and private lake set across gated 39.1 acres MAIN HOUSE - 10 bedrooms, 6 full baths, 3 half baths, 10 fireplaces, Kitchen has Miele Steam unit, Viking warming drawer, Viking microwave, 3 Viking ovens, including 6-burner and grill, 2 dishwashers, walk-in refrigerator, custom-designed and renovated in 2005, radiant heat. Main house has generator with auto transfer switch, 2 zones heat (1 zone radiant in kitchen) 4 zones central air and oil heat. BALLROOM - 4 bedrooms all with en-suite bathrooms, 2 half baths, 5 fireplaces, full kitchen with dishwasher, refrigerator and washer/dryer. Gilded age ballroom with plaster ceiling, 6 zones AC and heat (all new) each room has its own thermostat. GUEST HOUSE - 2 bedrooms, 1 full bathroom, original wood burning stove in kitchen. Guest house has 3 car-garage with a Tiffany clocktower clad in glazed ceramic. Guest house has 275 gallon oil heat, forced air, central air. Home has oil heat, 1 septic for main house & guest house. Separate septic for ballroom. Water is municipal, but there is also a well on site. Welcome to Rushmore estate. Set across over 39 acres of pristine woodland in the lower Hudson Valley. It is a rare offering of historic elegance and complete privacy. Originally commissioned in 1908 by financier/attorney Charles E. Rushmore, this Spanish Colonial-style mansion was designed as a secluded retreat. A long tree-lined 1/4 mile brick pavers driveway opens to a breathtaking estate centered around a grand Gilded-Age ballroom, vaulted hand-plastered ceilings, French doors, Palladian windows and an oversized fireplace creating an iconic setting. The home has incredible historic details throughout. The grounds are equally compelling with rolling lawns, a private lake with beachfront, a 60-foot infinity pool overlooking the water and a network of wooded trails that wind through the untouched landscapes of abundant wildlife. The trails connect to Shawangunk mountains. A romantic original gazebo, waterfall and multiple outdoor entertaining spaces create a true estate experience rarely found this close to Manhattan. This is a destination property equally suited as a private compound, legacy estate or event-driven retreat that offers a level of privacy, beauty and history that is increasingly rare in the Hudson Valley. Rushmore Estate is not just a home, it is a gilded-age masterpiece completely and historically in tact. Home is approved and zoned for event venue, house of worship, school, horses, cemetery, among others.

14 Castleton Drive, Highland Mills
$499,999
3 Beds ⋅ 2 Baths ⋅ 993892 MLS
Welcome to 172 Ridge Road, a delightful 3-bed, 2-bath split-level home offering 1,600 sq ft of comfortable living space in the heart of Highland Mills. Park easily in your two-car garage and driveway, then step into a home situated on nearly half an acre of yard that invites backyard barbecues, spontaneous play or quiet evenings outdoors. The living and dining areas flow together with relaxed ease, while the structured split-level layout gives each space its own purpose—ideal for guests and everyday life. Located in a warm and welcoming community with easy access to local schools, parks and commuter routes, this home blends suburban comfort with real-world practicality.

172 Ridge Road, Highland Mills
$424,999
3 Beds ⋅ 3 Baths ⋅ 987125 MLS
Welcome to this beautifully maintained end-unit townhouse in Highland Mills, offering the perfect blend of space, privacy, and modern updates. As an end unit, the home enjoys added natural light and enhanced privacy. Thoughtfully updated and well cared for, this property is ideal for buyers seeking low-maintenance living with high-end improvements. This 3-bedroom home features two spacious en-suite bedrooms, each with its own recently renovated bathroom showcasing stylish, contemporary finishes. Common bathroom is fully gutted and currently undergoing a complete renovation, this bathroom will be delivered entirely brand new from top to bottom. Planned updates include all-new walls, a modern shower, new vanity, mirror, and toilet—offering a fresh, clean, and contemporary space for the future owner. Perfect opportunity to enjoy a fully updated bathroom with no detail overlooked. This home has already been updated throughout, this home features brand-new flooring, fresh paint, modern ceiling fans, and newly installed closet systems, offering a stylish and is move-in-ready. Located within the Monroe-Woodbury Central School District, residents also have access to Woodbury Parks and Recreation—exclusively available to Woodbury residents—offering parks, pools, sports programs, and year-round community activities. Perfect for commuters, this home is just minutes to public transportation, minutes away to the New York State Thruway (I-87), and to the Palisades Parkway, and less than 5 miles to Woodbury Common Premium Outlets. New York City is approximately 50 miles away, making this an ideal location for both convenience and lifestyle. Enjoy all that the Hudson Valley has to offer with close proximity to United States Military Academy, Legoland, World Resort Casino, and Harriman State Park. Explore countless scenic hiking and biking trails, nearby ski mountains, charming local farms, distilleries, and wineries—offering year-round recreation and a true lifestyle destination right at your doorstep.

8 Laurel Court, Highland Mills
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