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New Windsor, NY Homes for Sale with Acreage

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  • /50

    $979,999

    $19K PRICE DROP
    • 7 Beds
    • 7 Baths
    • 5,625 Sq Ft

    10 Willys Ct, Rock Tavern, NY 12575

    Welcome to 10 Willys Court, an extraordinary custom colonial offering over 5,600 square feet of thoughtfully designed living space on a private 2.2-acre cul-de-sac in the heart of Rock Tavern. Combining exceptional size, versatility, and modern amenities, this one-of-a-kind residence features a truly authentic mother-daughter design—one of the area's rarest opportunities for multigenerational

    Agent Photo

    Joao Rodrigues

    Preferred Properties Real Esta

    10 Willys Ct, Rock Tavern, NY 12575
  • /46

    $820,000

    $5K PRICE INCREASE
    • 4 Beds
    • 3.5 Baths
    • 3,188 Sq Ft

    84 Pin Oak Dr, New Windsor, NY 12553

    **A Private Resort-Style Retreat in the Heart of the Hudson Valley**Welcome to 84 Pin Oak Drive, a beautifully appointed custom ranch tucked away on nearly two private acres at the end of a quiet cul-de-sac in one of New Windsor's most desirable neighborhoods. Offering over 3,100 square feet of thoughtfully designed living space, this exceptional home combines luxurious one-level living with

    Agent Photo

    Heather Bragg

    River to Ridge Rlty Associates

    84 Pin Oak Dr, New Windsor, NY 12553
  • /3

    $140,000

    • Land
    • 2.5 Acres
    • $56,000 per Acre

    35 Otterkill Rd, New Windsor, NY 12553

    The thing that stops most people from building is never the house. It is the year that comes before it, the soil testing and the septic engineering and the permitting, all of it paid for months before anyone can tell you whether the answer is yes. Here, that year has already happened, and someone else already paid for it.These 2.5 acres come with an engineered plan in hand. Perc tests and

    Agent Photo

    Brian Caplicki

    KW Hudson Valley United

    35 Otterkill Rd, New Windsor, NY 12553
  • /45

    $475,000

    Open Sun 12PM - 2PM $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 3,064 Sq Ft

    126 Lincolndale Acres, Washingtonville, NY 10992

    Private Hudson Valley Retreat – Just an Hour from NYC. Tucked at the end of a private road and surrounded by 5 wooded acres, this charming log cabin offers the kind of quiet, back-to-nature escape that's increasingly hard to find so close to the city. Settle into the swing on the wide covered front porch - your first taste of the slower pace that awaits you. Watch the surrounding woods blaze with

    Agent Photo

    Dana Posner

    Howard Hanna Rand Realty

    126 Lincolndale Acres, Washingtonville, NY 10992
  • /3

    $899,900

    • 4 Beds
    • 2.5 Baths
    • 2,778 Sq Ft

    1 Forest Ln, Salisbury Mills, NY 12577

    Nestled in the heart of the Hudson Valley, this new four-home enclave in the Town of Cornwall offers a rare blend of modern luxury and preserved natural beauty. These custom homes are uniquely positioned against the backdrop of the iconic Storm King Mountains and one of the nation’s tallest railroad trestles, providing a dramatic landscape that will remain pristine thanks to the surrounding Land

    Theresa Budich Howard Hanna Rand Realty

    1 Forest Ln, Salisbury Mills, NY 12577
  • /5

    $899,000

    New Construction
    • 6 Beds
    • 4.5 Baths
    • 4,500 Sq Ft

    131 Riley Rd, New Windsor, NY 12553

    NEW CONSTRUCTION!!! Targeted completion, August of 2026 !!! - 6 bedrooms / 4 bath home with unique, functional layout with well-appointed finishes!! Custom gourmet kitchen with eating area, Hardwood Floors, Dining Room, Bedroom count includes 3 master en-suites; 1 on first floor & 2 on second floor, which is perfect for guests. Perfect Location !!! Close to Schools, Shops, Major Roadways,

    Rafael Luciano Luciano Rios Property Grp, Inc

    131 Riley Rd, New Windsor, NY 12553
  • /16

    $499,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths

    1110 -1114 Route 94, New Windsor, NY 12553

    The Market is changing This area in the five corners in New Windsor is moving rapidly Fully Available Great Location Location ,Locations Time to buy when the Price is Great .This is a very fast growing area Many new business coming There are Two buildings included in the sale one is a 3 -4 bedroom house can be a great Mother daughter or plenty of room for the family the other building is a one

    Rhoda Ciancio Real Estate Connection Corp

    1110 -1114 Route 94, New Windsor, NY 12553
  • /44

    $599,000

    Open Sun 12PM - 4PM
    • 3 Beds
    • 2.5 Baths
    • 1,947 Sq Ft

    2 Lilac Hill Rd, New Windsor, NY 12553

    Amazing opportunity in New Windsor with Cornwall Schools! Set on 1.4 beautiful private acres along a peaceful private road, this three-bedroom, two-and-a-half-bath Colonial offers the space, updates and setting buyers are looking for. A beautifully landscaped front yard with mature gardens and four stately columns creates wonderful curb appeal, while inside you’ll find a warm, inviting home with

    Rosalie Cook Weichert Realtors

    2 Lilac Hill Rd, New Windsor, NY 12553
  • /27

    $189,900

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft

    10 Oakwood Terrace Unit 107, New Windsor, NY 12553

    ***Oakwood Terrace*** second-floor, one-level co-op features 2 bedrooms and 1 updated bathroom. The spacious primary bedroom offers generous closet space. Great sized living room has a sliding door to a private balcony overlooking the woods for a peaceful view. Dining room can easily accommodate a table for 6-8 and even be extended into the living room for the entertainer's dinner or game night!

    Celina Rofer Howard Hanna Rand Realty

    10 Oakwood Terrace Unit 107, New Windsor, NY 12553
  • /23

    $1,500,000

    • Land
    • 29 Acres
    • $51,724 per Acre

    0 Mt Airy Rd Unit KEY913137, New Windsor, NY 12553

    Be a visionary! This is 29 acres in the Hudson Valley—prime land where luxury living meets unmatched opportunity. Picture a new community of high-end homes, an equestrian estate development, or a luxury retreat destination. With open meadows, mature woodlands, and multiple building sites with ample frontage, the groundwork is already here. This property offers privacy and natural beauty—yet it’s

    Donna Ramundo Keller Williams Valley Realty

    0 Mt Airy Rd Unit KEY913137, New Windsor, NY 12553
  • /46

    $899,000

    • 8 Beds
    • 4 Baths

    9 Benedict Ln Unit 5-7, New Windsor, NY 12553

    Income-producing multi-property asset offered at approximately an 8% cap rate with $75,900 NOI. This unique offering includes three separate residences on one 1.4 acre parcel, delivering multiple income streams and long-term upside potential. Ideal for investors seeking yield, value-add opportunity, or a hybrid owner-occupant strategy. Located across the street from Cornwall High School and near

    Virginia Corbett eXp Realty

    9 Benedict Ln Unit 5-7, New Windsor, NY 12553
  • /33

    $1,100,000

    $150K PRICE INCREASE
    • 4 Beds
    • 3 Baths
    • 3,100 Sq Ft

    4 Jefferson Ave, New Windsor, NY 12553

    CORNWALL SCHOOLS ~ TO BE BUILT BY LOCAL ESTABLISHED REPUTABLE BUILDER ON THIS BEAUTIFUL PRIVATE LOT WITH VIEWS ON 5.1 ACRES. New construction & to be completed in 2027 approximately 11 months after fully executed contracts, weather permitting . Time to customize w/own colors. Approximately 3100' sq. ft. with central air throughout, 4-bedroom, 3 full bathroom colonial. Finished 344' sq. ft. bonus

    George Koudounas RE/MAX Benchmark Realty Group

    4 Jefferson Ave, New Windsor, NY 12553
  • /46

    $535,000

    • 3 Beds
    • 3 Baths
    • 2,338 Sq Ft

    600 Twin Arch Rd, Rock Tavern, NY 12575

    Welcome to this beautiful home located at 600 Twin Arch, situated on a spacious 1.3-acre lot. The main level features a bright and inviting living room, an eat-in kitchen, a primary bedroom with a full bath, and 2 additional bedrooms. The finished basement offers additional flexible living space, including a playroom, a living room, a storage room, and an additional full bathroom. A one-car

    Aron Ungar eRealty Advisors, Inc

    600 Twin Arch Rd, Rock Tavern, NY 12575
  • /33

    $1,200,000

    • 4 Beds
    • 3.5 Baths
    • 3,100 Sq Ft

    8 Jefferson Ave, New Windsor, NY 12553

    CORNWALL SCHOOLS ~ HOUSE TO BE BUILT AND TO BE COMPLETED APPROXIMATELY BY END OF 2026 ~ 1 ADDITIONAL LOT AVAILABLE READY TO BUILD. LOCAL REPUTABLE BUILDER. PRICE MAY ALTER IF SIZE CHANGES...FOR THE OTHER LOT BUILDER CAN MODIFY THE PLANS FOR UP TO 3300' SQ. FT. FOR A DIFFERENT PRICE. 8 Jefferson Ave. new construction to be completed 10-12 months after fully executed contracts, weather permitting.

    George Koudounas RE/MAX Benchmark Realty Group

    8 Jefferson Ave, New Windsor, NY 12553
  • /50

    $829,900

    $95K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,694 Sq Ft

    268 Lake Rd, Salisbury Mills, NY 12577

    Exceptional Spacious Colonial with Lake Views & Lake Rights. Set on a picturesque one-acre lot with views of Beaver Dam Lake and deeded lake rights, this meticulously crafted 4-bedroom, 3-full-bath, 2,700 sq. ft. Colonial offers the perfect blend of luxury, comfort, and thoughtful design. As the builder’s own home, no detail was overlooked. From the moment you arrive, you’ll appreciate the

    Paul Biagini Biagini Realty

    268 Lake Rd, Salisbury Mills, NY 12577
  • /32

    $899,000

    • 4 Beds
    • 3 Baths
    • 3,161 Sq Ft

    66 Pin Oak Dr, New Windsor, NY 12553

    Welcome to this stunning custom colonial offering over 3000 square feet of thoughtfully designed living space in one of the area’s most desirable neighborhoods. this does not include the basement. From the moment you enter, you’ll be captivated by the soaring two-story great room featuring a dramatic wall of windows that floods the home with natural light. The open-concept layout seamlessly

    Stephen Ramundo Keller Williams Valley Realty

    66 Pin Oak Dr, New Windsor, NY 12553
  • /49

    $765,000

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,566 Sq Ft

    464 Bull Rd, Rock Tavern, NY 12575

    New Construction! Welcome to this beautifully crafted 4-bedroom, 3-bathroom home offering the perfect blend of modern design, quality finishes and functional living spaces. Thoughtfully designed with today's lifestyle in mind, this home features an open-concept floor plan ideal for both everyday living and entertaining. The main level showcases a spacious living room anchored by a stunning

    Donna Gennaro Howard Hanna Rand Realty

    464 Bull Rd, Rock Tavern, NY 12575
  • /6

    $249,000

    $100K PRICE DROP
    • Land
    • 2.3 Acres
    • $108,261 per Acre

    0 Silver Stream Rd Unit KEY1020788, New Windsor, NY 12553

    Prime Commercial Development Opportunity in New Windsor! This 2.3-acre commercially zoned parcel offers exceptional potential in one of Orange County’s fastest-growing corridors. Located minutes from New York Stewart International Airport, major retailers, restaurants, Amazon fulfillment center, and the I-84, I-87, Route 9W, and Route 207 interchanges.The property is an ideal candidate

    Lazar Schvimmer Mount Realty

    0 Silver Stream Rd Unit KEY1020788, New Windsor, NY 12553
  • /40

    $572,000

    • 3 Beds
    • 2 Baths
    • 1,807 Sq Ft

    17 Old Hemlock Dr, New Windsor, NY 12553

    Perched atop a beautiful hilltop setting, this inviting three-bedroom High Ranch offers beautiful views, a warm and welcoming atmosphere, and an exceptionally convenient location. Enjoy the peaceful surroundings of an elevated property while remaining just minutes from shopping, schools, major highways, restaurants, and everyday conveniences.The upper level features a charming living

    Heidi Oliver Houlihan Lawrence Inc.

    17 Old Hemlock Dr, New Windsor, NY 12553
  • /38

    $689,000

    • 5 Beds
    • 3.5 Baths
    • 2,776 Sq Ft

    13 James Wilkinson Rd, Rock Tavern, NY 12575

    AMAZING 1.8 ACRE LEVEL PROPERTY! Stunning setting with fully fenced in INGROUND SALT WATER POOL! Extended updated bi-level! Impressive, family room with fireplace, cathedral ceilings and access to trex deck overlooking the park-like backyard with mature trees! Spacious home featuring 5 bedrooms, 4 FULL bathrooms! Kitchen features granite countertops, abundant wood cabinetry, pantry with custom

    Sharon Kushner eXp Realty

    13 James Wilkinson Rd, Rock Tavern, NY 12575
  • /42

    $860,000

    Open Sun 12PM - 3PM $30K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,998 Sq Ft

    27 Wild Turkey Ln, Rock Tavern, NY 12575

    Welcome to 27 Wild Turkey Lane—where every wish feels within reach.This beautifully maintained five-bedroom, three-bath Colonial blends timeless charm with modern sophistication, offering a lifestyle of comfort, elegance, and possibility.Step through the grand open foyer into a flowing, open-concept design that invites you to explore. The main level features gleaming hardwood floors, a

    Carlos Infante Coldwell Banker Realty

    27 Wild Turkey Ln, Rock Tavern, NY 12575
  • /2

    $1,275,000

    $525K PRICE DROP
    • Land
    • 15.5 Acres
    • $82,258 per Acre

    0 Silver Stream Rd Unit ONEH6282502, New Windsor, NY 12553

    MAJOR PRICE REDUCTION motivated seller! 15.5 Acre land for Commercial/Industrial uses on Silver Stream Rd New Windsor NY. Next to the expanding Stewart International Airport (SWF). Some engineering complete, zoned PI, site is in the town/municipal sewer district, municipal water nearby, the parcel would be appropriate for over 100,000 sqft logistics facility/warehouse with many possibilities for

    Eliezer Safdie Sage Realty Center LLC

    0 Silver Stream Rd Unit ONEH6282502, New Windsor, NY 12553
  • /37

    $750,000

    • 4 Beds
    • 2.5 Baths
    • 3,030 Sq Ft

    58 Moores Hill Rd, New Windsor, NY 12553

    Welcome to this stunning brick colonial on a private 1.5 acre yard! The spatial layout is remarkable -- office/den on main floor away from everything with french doors, crackline propane fireplace in the living room, impressive entry foyer ceiling with tiered and coiffered ceilings throughout, 4 full bedrooms upstairs with a bonus media room, and expert finishes around the entire home. Hardwood

    Lance Pahucki William Raveis-New York LLC

    58 Moores Hill Rd, New Windsor, NY 12553
  • /48

    $549,900

    • 5 Beds
    • 4 Baths
    • 2,790 Sq Ft

    150 Mount Airy Rd, New Windsor, NY 12553

    Oldie But Goodie with Endless Possibilities!What an unbelievable property! Nestled on 2 private acres, this unique offering features a spacious two-story home plus a separate one-bedroom apartment—perfect for extended family, guests, rental income, or a home office setup.Enjoy the privacy and tranquility of having no homes behind you, providing a peaceful backdrop and added peace of mind.

    Jane Alfidi Howard Hanna Rand Realty

    150 Mount Airy Rd, New Windsor, NY 12553
  • /28

    $869,900

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,770 Sq Ft

    3 Forest Ln, Salisbury Mills, NY 12577

    Nestled in the heart of the Hudson Valley, this new four-home enclave in the Town of Cornwall offers a rare blend of modern luxury and preserved natural beauty. These custom homes are uniquely positioned against the backdrop of the iconic Storm King Mountains and one of the nation’s tallest railroad trestles, providing a dramatic landscape that will remain pristine thanks to the surrounding Land

    Theresa Budich Howard Hanna Rand Realty

    3 Forest Ln, Salisbury Mills, NY 12577
  • /49

    $725,000

    • 4 Beds
    • 2.5 Baths
    • 2,268 Sq Ft

    1 Sean Ct, Rock Tavern, NY 12575

    Welcome home to this beautiful 4-bedroom, 2.5-bath Colonial set on 3.8 picturesque acres in Rock Tavern! Offering a versatile floor plan, inviting spaces, and an incredible collection of outbuildings, this property provides the perfect blend of comfort, functionality, and country living. A charming rocking-chair front porch welcomes you into a spacious home featuring an open-concept layout,

    Kyla Thomas Howard Hanna Rand Realty

    1 Sean Ct, Rock Tavern, NY 12575
  • /2

    $80,000

    • Land
    • 41.5 Acres
    • $1,928 per Acre

    64 Shalimar Dr, New Windsor, NY 12553

    Online Bankruptcy Auction: 40+ Acres of Vacant Land: 3 Lot Assemblage. Bulk Sale Only. Bidding opens 10/13/26 at 11:00 am & ends 10/15/26 at 11:00 am (appx). The listing price of $80,000 exclusively represents the Opening Bid Amount Only and not the asking price. Please conduct independent due diligence as the property sells “AS-IS " and the information provided is not guaranteed to be accurate.

    David Constantino David R Maltz And Co Inc

    64 Shalimar Dr, New Windsor, NY 12553
  • /13

    $270,000

    $50K PRICE DROP
    • Land
    • 2.87 Acres
    • $94,077 per Acre

    0 Moores Hill Rd Unit KEY942803, New Windsor, NY 12553

    .This is the first time this land is offered, and it is in the Cornwall School District. Excellent new construction opportunity. This 2.9-acre lot offers a scenic view of Brown’s Pond, a quiet .3-mile reservoir providing a peaceful setting and attractive backdrop for a custom home. Boating is not permitted, preserving the natural views and tranquility. The parcel provides generous buildable area

    Deborah Warner Keller Williams Valley Realty

    0 Moores Hill Rd Unit KEY942803, New Windsor, NY 12553
  • /32

    $299,000

    $16K PRICE DROP
    • 2 Beds
    • 1 Bath
    • 1,085 Sq Ft

    95 Riley Rd, New Windsor, NY 12553

    Welcome to 95 Riley Road in New Windsor, NY! Set on approximately 2.2 acres, this charming property offers a wonderful combination of privacy, outdoor space, and a convenient Hudson Valley location.From the moment you arrive, you’ll appreciate the peaceful setting and spacious property surrounding the home. Inside, the home offers comfortable living spaces with plenty of opportunity to

    Anthony Minieri KW Hudson Valley United

    95 Riley Rd, New Windsor, NY 12553
  • /29

    $600,000

    $299K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,118 Sq Ft

    158 Sycamore Dr, New Windsor, NY 12553

    Beautifully maintained home located in the highly desirable Cornwall Central School District and set on over 6 acres of level, usable property offering privacy, space, and endless possibilities. This charming residence features 3 spacious bedrooms, a finished playroom perfect for recreation or a home office, and a cozy fireplace creating a warm and inviting atmosphere. Elegant hardwood flooring

    Syed Wasim American Dream Homes 110 Inc

    158 Sycamore Dr, New Windsor, NY 12553

Home Price Trends

Median Sale Price
$445,000
Median Single Family Sale Price
$479,500
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$312,000
Median 1 Bedroom Sale Price
$200,000
Average Price Per Sq Ft
$257
Number of Homes for Sale
60
Last 12 months Home Sales
265
Months of Supply
2.70
Median List Price
$450,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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