Highland Mills Homes with Pool Amenities

Welcome to Highland Mills, New York – a hidden gem nestled in the heart of Orange County that perfectly blends serene suburban living with easy access to urban conveniences. This charming community is surrounded by picturesque landscapes, providing residents with a tranquil retreat while still being just a short drive from the bustling cities of New York and New Jersey. With its rich history, friendly neighborhoods, and an abundance of outdoor recreational opportunities, Highland Mills is an ideal place for families, retirees, and everyone in between.

One of the most enticing features of homes in Highland Mills is the availability of properties with luxurious pool amenities. Imagine stepping into your backyard oasis on a warm summer day, where you can relax by your private pool, host barbecues with friends, or simply unwind with a good book. These homes offer not just a place to live, but a lifestyle filled with leisure and enjoyment. Whether you prefer a contemporary design or a classic style, you’ll find a variety of options that cater to your personal taste.

In addition to the allure of poolside living, Highland Mills boasts excellent schools, vibrant community events, and an array of parks and hiking trails for the outdoor enthusiast. With its perfect blend of nature and community spirit, Highland Mills truly feels like home. Explore the possibilities of your dream home with a pool in this enchanting town, and start creating memories that will last a lifetime!

Newest Highland Mills Homes with Pool Amenities

$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

$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

$289,000

2 Beds ⋅ 2 Baths ⋅ 1014150 MLS

Welcome home to this beautifully updated 2-bedroom end-unit townhouse offering the perfect blend of comfort, style, privacy, and convenience. This move-in ready home presents a rare opportunity to own a residence that has been lovingly maintained and thoughtfully updated throughout the years. Featuring gorgeous new flooring, a stunning new kitchen with modern finishes, beautifully renovated bathrooms, gas heat, and gas cooking, central air, every detail has been carefully curated for today's lifestyle. Now let's discuss LOCATION! Step outside to your own private outdoor retreat featuring an exceptional custom paver patio with brilliant hardscaping, creating the perfect setting for entertaining, dining al fresco, or simply relaxing while enjoying peaceful wooded views and added privacy. As an end unit backing to the woods, you'll appreciate the added sense of space and tranquility rarely found. You will also love your own carport. An exclusive space w/ added storage area. Additional parking is also available. Located in a highly desirable community with amenities galore, residents enjoy access to Woodbury Recreation, swimming pools, the reservoir, beach areas, playgrounds, sports courts, walking trails, and a variety of year-round activities and events. New York City commuter-friendly and ideally situated just minutes from Woodbury Common Premium Outlets, West Point Military Academy, Bear Mountain State Park, Harriman State Park, major highways, dining, shopping, and recreation. Whether you're searching for a full-time residence or a weekend retreat, this exceptional townhouse offers low-maintenance living and an unbeatable Hudson Valley lifestyle in a picturesque setting. Opportunities to purchase a one-owner home with this level of care, updates, privacy, and location are truly rare.

13 Redwood Drive, 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

$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

$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

$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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