New Windsor Real Estate

Welcome to New Windsor, New York – a charming town nestled in the heart of Orange County. With its rich history, stunning landscapes, and vibrant community, New Windsor offers a delightful blend of small-town charm and modern conveniences.

Situated just a stone’s throw from the Hudson River, New Windsor boasts a picturesque setting with scenic views and ample outdoor recreational opportunities. The town is surrounded by lush parks, including the expansive Washington Lake Park, where residents can enjoy picnicking, hiking, and fishing in a serene environment. The nearby Storm King Art Center, one of the largest sculpture parks in the country, adds a cultural flair, inviting art enthusiasts from near and far to explore its breathtaking grounds.

New Windsor is not only known for its natural beauty but also for its rich historical significance. The area played a crucial role during the Revolutionary War, and visitors can explore historical sites like the New Windsor Cantonment, where American soldiers camped during the winter of 1782-1783.

Families will appreciate the excellent schools in the New Windsor district, as well as the friendly community atmosphere that makes it easy to connect with neighbors. With convenient access to major highways, commuting to nearby cities like New York City is a breeze, making New Windsor an ideal location for those who seek a peaceful suburban lifestyle without sacrificing urban accessibility.

Whether you’re looking to settle down or invest, New Windsor presents a unique opportunity to be part of a thriving community steeped in history and natural beauty. Come and discover why so many are proud to call New Windsor home!

Newest Listings in New Windsor

$699,999

4 Beds ⋅ 4 Baths ⋅ 1032874 MLS

This custom-built Contemporary Colonial captures breathtaking mountain views from every direction and features cathedral-style ceilings, a gas fireplace in the great room, and gorgeous daily sunset views. Set on a private 2-acre property, the home offers over 4,000 sq ft of sunlit living space with vaulted ceilings, skylights, Andersen windows, three fireplaces, two dens with Brazilian hardwood floors, and a bright modern eat-in kitchen that opens to an expansive three-tier deck system overlooking the stunning landscape. The fully finished walk-out lower level provides private exterior access—ideal for extended family, guests, or a home office—and includes a large media room and an oversized 3-car garage with exceptional storage or workshop capability, plus additional parking for over 10 vehicles. Perfectly located just minutes to Salisbury Mills train, I87, Route 9W, West Point, Stewart Airport, Moodna Creek trails, Storm King Art Center, Woodbury Commons, Resorts World Casino, Legoland, Bear Mountain, and historic Hudson Valley sites, this home offers a rare blend of sweeping views, space, and convenience in a setting that truly stands out.

254 Orrs Mills Road, New Windsor

$750,000

1032698 MLS

A great opportunity awaits you to open your own business in this great, refreshed and remodeled, approx. 3600 sq. ft office building with caretakers quarters upstairs in a prime, booming location in New Windsor. Close to major shopping, restaurants & Hudson riverfront. It was formerly a thriving medical office with 8/9 rooms, large waiting room, reception area, offices, exam rooms and recreation lounge. There is ample parking in the front & rear of the building. Buy it and make it your own successful, prosperous business enterprise.

270 Quassaick Avenue, New Windsor

$315,000

2 Beds ⋅ 2 Baths ⋅ 1031728 MLS

Welcome to easy, low-maintenance living in the desirable Washington Green community! This bright and inviting ground-level 2-bedroom, 2-bath condo offers the perfect blend of comfort and convenience. Filled with abundant natural light, the spacious layout features a welcoming living room complete with a gas fireplace accented by a marble surround, a generous dining area, a galley kitchen, and carpeting throughout. The primary suite includes a walk-in closet and a private full bath, while the second bedroom and additional full hall bath provide flexibility for guests, a home office, or additional living space. A stackable washer and dryer are conveniently located right in the unit. Step outside to your private patio and enjoy the beautifully maintained grounds. Washington Green residents have access to outstanding community amenities, including a pool, tennis courts, playground, and clubhouse, all while being just minutes from shopping, dining, major highways, Stewart International Airport, and the Hudson River waterfront. Don't miss this opportunity to own a move-in-ready condo in one of New Windsor's most sought-after communities!

1002 Washington Green Unit #AG2, New Windsor

$515,000

3 Beds ⋅ 4 Baths ⋅ 1030988 MLS

Enjoy the luxury of moving into this recently built town home located in the sought after town of New Windsor! At a boasting 2550 square feet, this spacious airy home features a one of a kind kitchen with a center island, stainless steel appliances, high ceilings and recessed lighting. The open floor plan is perfect for entertaining, with a lovely patio overlooking the spacious backyard. The upscale primary suite features an elegant en-suite bathroom, walk in closet with ample amount of space for relaxation. The finished walkout basement is an added perk that has a airy family room or fourth bedroom with a powder bath with 1 car garage. Perfect commuter location, close to Woodbury Commons, West Point and just minutes away from major highways, I-84, I-87, Route 9W, Stewart Airport, Beacon Metro North, Newburgh waterfront, shopping and just 60 miles North of NYC! Pack your bags and call this your new home!

501 Iron Forge Lane, New Windsor

$850,000

4 Beds ⋅ 3 Baths ⋅ 1019242 MLS

Welcome to this stunning center hall Colonial set on over 2 acres of pristine, level property in the highly sought-after Washingtonville School District. A grand two-story foyer is flanked by a formal living room and dining room, leading into an open-concept family room with a fireplace, spacious kitchen featuring granite countertops, stainless steel appliances, and a breakfast nook. The first floor also offers a versatile bonus room ideal as a home office, a half bath, second laundry room, and access to the attached two-car garage. Sliding glass doors open to an exceptional backyard with a patio, in-ground pool, hot tub, gazebo, expansive entertaining area, and an enormous grassy lawn. Upstairs you’ll find four spacious bedrooms and two full baths, while the home’s generous layout lives like a six-bedroom residence. Conveniently located just minutes from the Cornwall Metro-North station, parks, shopping, and major commuter routes.

33 Luthien Forest Road, New Windsor

$488,888

3 Beds ⋅ 2 Baths ⋅ 1030142 MLS

Welcome to 42 Keats Dr, New Windsor! This 3 bedroom, 2 full bath home offers 1,764 sq ft of living space in a convenient, established neighborhood off Temple Hill Rd. Located in the Newburgh City School District, with easy access to Rt 32, I-84, and Stewart International Airport. Under 60 miles to NYC. Great layout with room to personalize — perfect for buyers looking to add their own touches. Don't miss this opportunity in a sought-after New Windsor location! MLS remarks are usually capped around 750-1000 characters depending on the board, so this fits comfortably. But it's still generic — MLS listings sell on specifics (updates, sq ft breakdown, taxes, lot size, garage). If you give me the price, updates, and any standout features, I can tighten this into something that actually competes and ranks well in search.

42 Keats Drive, New Windsor

$385,000

3 Beds ⋅ 2 Baths ⋅ MDCR2036150 MLS

Welcome home to this charming 3-bedroom, 2-full-bath residence that offers the perfect blend of comfort, style, and convenience. Relax with your morning coffee on the inviting front porch or unwind in the spacious screened-in back porch overlooking your private backyard oasis. Step outside to enjoy the beautiful in-ground pool, perfect for entertaining family and friends or cooling off on warm summer days. Inside, you'll find a functional layout with comfortable living spaces designed for everyday living. Conveniently located in a desirable area close to shopping, dining, schools, and major commuter routes, this home combines a peaceful setting with easy access to everything you need. Whether you're looking for a place to entertain or simply enjoy everyday living, this home is ready to welcome you.

315 College Ave, New Windsor

$349,000

4 Beds ⋅ 1 Baths ⋅ 1022051 MLS

Welcome to 28 Hilltop Drive. This lovely home is priced to sell, so come and see for yourself! Starting with the front of home with its curb appeal and property, you can see it is very well maintained and inviting. The backyard with its large and sturdy deck is a perfect place to relax, be peaceful or entertain friends and family. As you turn onto Hilltop Drive you will appreciate the handsome neighborhood and your new neighbors. Entering front door there is a good-sized living room with attractive laminate flooring and sunshine. Kitchen has ample space, an easy flow to maneuver, a pass-through opening to dining room as well as brand new flooring. The dining room has enough room to easily accommodate. Bathroom tastefully updated 2020. Two roomy bedrooms on 1st floor and two sizable bedrooms on second level with storage space. Very large walkout basement that has potential for future living space. Garage at present was used as workshop. Short drive from property to Newburgh Waterfront which is a vibrant dining and entertainment hub on the shore of the Hudson River. Waterfront has beautiful unobstructed views of the river and mountains. Also, a convenient location for commuters.

28 Hilltop Drive, New Windsor

$99,900

2 Beds ⋅ 2 Baths ⋅ 1029336 MLS

Amazing end lot with privacy! Imagine your bright and modern new home to be ready for occupancy approx 8/1! This lovely home offers comfort, convenience and affordability. The home features a bright and airy open layout. The kitchen cabinets are white and it offers a crisp contemporary feel with tons of cabinets and appliances. You'll find two nice bedrooms situated on opposite ends of the home, offering privacy. The primary bedrooms features its own private bathroom. Enjoy a super convenient location – just a quick 5-minute drive to town and less than 10 minutes to both I-84 and I-87. Plus, you're only about an hour from the New York City! This spot is also close to West Point, Stewart Airport, the Beacon Bridge, the Newburgh-Beacon Ferry, Metro-North, and both major highways. Please note: The photos shown are from a similar home from the same manufacturer. The home is on order and is expected soon!

11 Square Hill Road Unit ##27, New Windsor

$550,000

5 Beds ⋅ 5 Baths ⋅ MDCR2036556 MLS

Coming Soon! Welcome to 2828 Graybill Court in New Windsor, MD—a spacious and versatile property offering endless possibilities for today's evolving lifestyle. With 5 bedrooms, 4.5 bathrooms, two full kitchens, 2 living rooms, two washers, and two dryers, this unique home is thoughtfully designed to accommodate a variety of living arrangements while providing comfort, privacy, and flexibility. The functional floor plan allows for separate living areas, making it ideal for households seeking additional privacy, long-term guests, or extended living space. The second kitchen and dedicated laundry areas offer convenience and independence, which can enhance everyday comfort for everyone in the home. The partially finished basement provides even more potential, with ample space to create additional rooms for recreation areas, offices, hobby rooms, or storage to suit your needs. Whether you're looking for room to grow, space for home-based activities, or a property that can adapt to changing circumstances, this home offers exceptional versatility. Investors and buyers seeking flexible living arrangements will appreciate the layout's potential for creating separate 2 living spaces, subject to local zoning and permitting requirements and possible use as assisted living facility or other shared living home. The generous design also offers opportunities for those exploring shared living configurations or future customization. Located on a quiet cul-de-sac in desirable New Windsor, this property combines generous square footage with the flexibility to meet a wide range of housing needs. If you've been searching for a home that can evolve with your lifestyle, this home is ready to welcome your vision.

2828 Graybill Ct, New Windsor

$444,000

3 Beds ⋅ 2 Baths ⋅ 1027849 MLS

Welcome to 19 Farmstead Road! This centrally located 3 Bedroom, 2 bath home is awaiting its next chapter. With 2 bedrooms and full bath on the first floor, there's also a bedroom and bathroom on the second floor. The kitchen and living room is open and ready for entertaining with a wood burning fireplace and slider to the wrap around porch. The back yard is fenced in for the pets and kids with a level spot with electric to install an above ground pool if desired. The garage is located under the house or could also function as a workshop. With access to the main house from garage, the basement has room for storage and more. Located 18 minutes from Beacon train station, 20 minutes to West Point, 13 minutes to I-87/I-84 interchange.

19 Farmstead Road, New Windsor

$330,000

2 Beds ⋅ 2 Baths ⋅ 1025920 MLS

Welcome to 309 Gazebo Court in Windsor Crest, a thoughtfully updated first-floor condominium offering comfortable single-level living with a peaceful wooded backdrop. Freshly painted and move-in ready, this two-bedroom, two-bath home features updated bathroom vanities, toilets, lighting, stainless steel appliances, newer carpeting, and a recently updated water heater. The owners also made practical improvements throughout, including motion-activated closet lighting and relocated HVAC filter access for easier everyday maintenance. Enjoy a private patio overlooking a lawn and mature woods, along with generous storage, a walk-in closet, and in-unit laundry. Community amenities include a pool, clubhouse, and tennis and pickleball courts, all conveniently located just minutes from shopping, restaurants, Stewart International Airport, major commuter routes, and the Beacon waterfront. Most of the existing furniture can also remain, offering a convenient turnkey opportunity for the next owner.

309 Gazebo Court, New Windsor

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