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Homes for Sale in 12529

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  • /19

    $325,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    Welcome to THE UPSTATE RETREAT--where every day feels like a vacation on Copake Lake, the largest lake in Columbia County, spanning approximately 425 acres. Whether you're searching for the perfect weekend escape, a summer lake house, or a year-round getaway, this charming 2-bedroom, 1-bath bungalow offers the quintessential upstate lifestyle just over two hours from New York City. Beyond the

    Agent Photo

    Mark Saxby

    Berkshire Hathaway HomeService

    81 SW Colony Rd, Hillsdale, NY 12529
  • /5

    $225,000

    • Land
    • 6 Acres
    • $37,500 per Acre

    L135.2 Rockledge Rd, Hillsdale, NY 12529

    Escape to your own private sanctuary in the heart of Columbia County's coveted Hudson Valley. This 6 acre wooded parcel on scenic Rockledge Road offers the perfect canvas for your dream retreat, with mature trees providing natural privacy and a peaceful, secluded setting that feels worlds away from the everyday. Ideally situated in the Town of Hillsdale -- one of the region's most sought-after

    Agent Photo

    Jamie Mazuryk

    Venture Fox Realty Group LLC

    L135.2 Rockledge Rd, Hillsdale, NY 12529
  • /36

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 1,977 Sq Ft

    3493 County Route 7, Hillsdale, NY 12529

    Escape to your own private retreat where lake living, outdoor adventure, and timeless country charm come together! Just steps from scenic Copake Lake, this property offers access to one of Columbia County's premier recreational destinations. The 410-acre, motorboat-friendly lake is perfect for boating, waterskiing, kayaking, paddleboarding, and excellent fishing, while nearby Copake Country Club

    Agent Photo

    Sabrina Puppolo

    Corcoran Country Living

    3493 County Route 7, Hillsdale, NY 12529
  • /75

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    0 Anthony St Unit LotWP001, Copake, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25 acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin Whitetail Properties Real Estate

    0 Anthony St Unit LotWP001, Copake, NY 12529
  • /42

    $900,000

    $200K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,495 Sq Ft

    309 Pine Ridge Ln, Hillsdale, NY 12529

    Nestled on a wooded hillside on one of Hillsdale's prettiest country roads is where you will discover this exceptional 2,500 sq.ft. custom-built home. The 5.5-acre parcel sits above Pine Ridge Lane; a lightly travelled country road located just off Mitchell Street in the heart of Hillsdale. Surrounded by nature in every direction, the peaceful, park-like setting is unique and as beautiful as any

    Margaret Bower Avenia Columbia County RE Specialist

    309 Pine Ridge Ln, Hillsdale, NY 12529
  • /43

    $1,350,000

    New Construction $125K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,350 Sq Ft

    501 Birch St, Craryville, NY 12521

    Newly constructed and thoughtfully designed, this home is ideally located within the Copake Lake community-Columbia County's only high-speed motorboat lake-and built by one of the area's most respected contractors. The property reflects quality craftsmanship throughout.The home offers 3 bedrooms and 3 full bathrooms, including two primary suites on the main level. The third bedroom is on the

    John Barbato Compass, Hillsdale

    501 Birch St, Craryville, NY 12521
  • /6

    $175,000

    $120K PRICE DROP
    • Land
    • 33.31 Acres
    • $5,254 per Acre

    50 Dugway Rd, Hillsdale, NY 12529

    Escape to 33.31 acres of untouched beauty in Columbia County, NY. This stunning parcel of wooded land offers complete privacy with no neighbors in sight, just you and the tranquility of nature. Imagine the possibilities as you explore the lush, wooded landscape teeming with wildlife. This parcel features a dynamic topography of hills that reach an elevation of over 1,000 feet. With this parcel,

    Jeffrey McKinney Beach & Bartolo Realtors

    50 Dugway Rd, Hillsdale, NY 12529
  • /33

    $389,000

    • 4 Beds
    • 1 Bath
    • 2,229 Sq Ft

    1953 County Road 11, Claverack, NY 12513

    Step into a home that feels like it has been quietly telling its story since the 1800's, where every beam and board carries the charm of a bygone era. This classic colonial residence preserves its original character with exposed beams stretching across the main floor and a layout that balances simplicity with purpose. The kitchen is modest yet functional, anchored by a traditional wood store that

    Karen Davala Davala Real Estate, LLC

    1953 County Road 11, Claverack, NY 12513
  • /13

    $325,000

    • Land
    • 24.4 Acres
    • $13,320 per Acre

    120 Dugway Rd, Hillsdale, NY 12529

    If the home you dream of building includes a private setting, on a hill that's surrounded by nature, and valuable infrastructure already in place, then this is the land for you. The lot is 24.40 acres of beautiful, mostly wooded land with a cleared one-acre meadow BUILD SITE that is located high on the hill and far from the road. There's a roughed-in DRIVEWAY that starts at the road with a bridge

    Jeffrey McKinney Beach & Bartolo Realtors

    120 Dugway Rd, Hillsdale, NY 12529
  • /50

    $949,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 State Route 23, Hillsdale, NY 12529

    Steeped in Hillsdale’s rich history, this extraordinary property began its life as one of the area’s original grist mills, situated in the area of Hillsdale once known as Murray’s Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 State Route 23, Hillsdale, NY 12529
  • /40

    $859,000

    $120K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,293 Sq Ft

    44 SW Colony Rd, Hillsdale, NY 12529

    Set on the shores of Copake Lake, this charming waterfront home blends classic lake character with thoughtful modern updates. Offering three bedrooms and 1.5 baths, the home features a bright open kitchen, living, and dining area designed for easy lake living and entertaining. Recent renovations, including HVAC, septic system, and expansion to main floor, bring fresh style and comfort while

    Austin Urban Venture Fox Realty Group

    44 SW Colony Rd, Hillsdale, NY 12529
  • /24

    $575,000

    $40K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 864 Sq Ft

    5 Adams Dr, Hillsdale, NY 12529

    This charming 3 BR, 1.5 Bath cottage is located across the street from Copake Lake and the HOA Waterfront, Marina and Beach area. Unlike some of the other homes in the area, the house is situated on an elevated, oversized lot with a big front yard and spectacular sunset views. Inside, the house features real wood paneling and a wood burning stove in the living room, a cozy kitchen with a new gas

    Russ Stein Compass Greater NY LLC

    5 Adams Dr, Hillsdale, NY 12529
  • /6

    $3,490,000

    • 3 Beds
    • 4 Baths
    • 7,571 Sq Ft

    351 Lakeview Rd, Craryville, NY 12521

    Welcome to Mickey's Marina, a rare waterfront opportunity located at 351 Lakeview Road. Set along the shoreline with beautiful lake views, this unique property blends recreation, income potential, and lifestyle in one exceptional offering. The marina features direct water access with multiple boat slips, making it an ideal destination for boating enthusiasts and seasonal visitors alike. With its

    Austin Urban Venture Fox Realty Group

    351 Lakeview Rd, Craryville, NY 12521
  • /44

    $1,485,000

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    51 Taconic Creek Rd, Hillsdale, NY 12529

    This perfect modern farmhouse retreat is tucked away on one of Columbia County's most quiet and beautiful roads guaranteeing a tranquil respite from the city. Being one of just a handful of properties on the road creates a sense of peace and quiet that is unmatched. While a feeling of simplicity emanates throughout the land there is a clear level of sophistication in the design details. The

    Thomas Pawlowski Four Seasons Sotheby's Int.

    51 Taconic Creek Rd, Hillsdale, NY 12529
  • /41

    $2,195,000

    • 3 Beds
    • 3 Baths
    • 2,755 Sq Ft

    292 White Hill Rd, Hillsdale, NY 12529

    Sited at the highest point in Hillsdale this modern home captures the world around while being incredibly private. Main house has tall ceilings tremendous natural light and doors bringing you outside from every space. Music room on the east side captures the Berkshire hills with doors out to the breakfast patio. Office with en suite is off the entry. Second floor is the primary suite; everywhere

    Jen Harvey COMPASS MASSACHUSETTS , LLC GB

    292 White Hill Rd, Hillsdale, NY 12529
  • /26

    $1,100,000

    $175K PRICE DROP
    • 1 Bed
    • 2 Baths
    • 1,700 Sq Ft

    401 Collins St, Hillsdale, NY 12529

    Discover a truly singular retreat: a 1,700-square-foot, octagonal contemporary barn residence designed and built by a noted architectural designer. Set deep within more than four acres of pristine woodlands on one of Columbia County’s most coveted roads, this home offers the rare combination of modern architecture, privacy, and effortless living. Expansive pivoting picture windows invite a

    Pamela King-Belfor Four Seasons Sothebys Intl

    401 Collins St, Hillsdale, NY 12529
  • /30

    $619,000

    $30K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,500 Sq Ft

    416 Whippoorwill Rd, Hillsdale, NY 12529

    This one checks all of the boxes. Our newly listed two bedroom, two bath Cape Cod style home in Hillsdale has been meticulously maintained and is in excellent condition inside and out. The main level features a functional kitchen, dining area, bathroom, and living room centered around a propane fireplace; all with hardwood floors. A 12x12 great room with hardwood floors was added to provide

    Margaret Bower Avenia Columbia County RE Specialist

    416 Whippoorwill Rd, Hillsdale, NY 12529
  • /5

    $259,000

    • Land
    • 15.47 Acres
    • $16,742 per Acre

    191 Berkshire Rd, Hillsdale, NY 12529

    Discover the perfect opportunity to build your dream home on this expansive 15.47-acre parcel at 191 Berkshire Road, bordering Copake Country Club and just minutes from Copake Lake. This fully undeveloped property is part of the desirable Sam Hill Road community, offering shared waterfront access through the HOA. Ideally located just 25 minutes from Hudson and Great Barrington, MA, you'll enjoy

    Austin Urban Venture Fox Realty Group

    191 Berkshire Rd, Hillsdale, NY 12529
  • /24

    $675,000

    • Land
    • 9.57 Acres
    • $70,533 per Acre

    109-Lot 4 Lake Ridge Ln, Copake Lake, NY 12521

    The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. Access the waterfront from your individually appointed boat slip on the 99ft of private water frontage owned by the Association. A special opportunity to enjoy lake

    John Barbato Compass, Hillsdale

    109-Lot 4 Lake Ridge Ln, Copake Lake, NY 12521
  • /26

    $650,000

    • Land
    • 10.55 Acres
    • $61,611 per Acre

    162-Lot 10 Lake Ridge Ln, Copake Lake, NY 12521

    The Ridge at Copake Lake is a gated private road of 11 ready-to-build lots nestled in the lush landscape of an untouched mountain top. Each designated building site has been artfully tailored to visually isolate one home from another. A special opportunity to enjoy lake living within a uniquely private setting. The 10+ acres of Lot 10 embrace direct views of the Taconic mountains to the east.

    John Barbato Compass, Hillsdale

    162-Lot 10 Lake Ridge Ln, Copake Lake, NY 12521
  • /7

    $257,000

    $2K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,304 Sq Ft

    9249 Route 22 Rd, Hillsdale, NY 12516

    Mixed Residential/Commercial building, with 3 rentable spaces. Current RR 30,540. One side of building has commercial reception area down and 1BR apartment above. Rental 1395/m. Other side is studio apartment up and storefront down. Can be rented to same party for commercial downstairs. Current rental is 795 + 550. Ideal for live/work. Building in excellent condition, roof less than 5 years old.

    David Birch Barns & Farms Realty, LLC

    9249 Route 22 Rd, Hillsdale, NY 12516
  • /19

    $392,500

    • 2 Beds
    • 2 Baths
    • 1,494 Sq Ft

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529

    Colonial Home on a Beautiful Country Parcel with New Garage Nestled on a peaceful country road, this charming two-bedroom Colonial offers the perfect blend of privacy, comfort, and convenience. Set back from the road on a beautiful parcel, the home welcomes you into a bright, open-concept living and dining area filled with natural light and complemented by attractive hardwood floors. The

    Jonathan Scarinzi Elyse Harney Real Estate

    155 Pumpkin Hollow Rd N, Hillsdale, NY 12529
  • /51

    $729,900

    • 3 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    417 Overlook Dr, Hillsdale, NY 12529

    Discover Your Dream Cape-Style Home: A Serene Escape on 2.1 Acres Nestled in a tranquil setting, this stunning Cape-style home offers the perfect blend of comfort and luxury, with 2.1 acres of nature at your doorstep. Imagine sipping your morning coffee on the spacious front porch while listening to the gentle rustle of leaves around you. Step inside to an inviting and dramatic living room, where

    Barbara Robinson Red Apple Realty

    417 Overlook Dr, Hillsdale, NY 12529
  • /7

    $95,000

    • Land
    • 12.95 Acres
    • $7,336 per Acre

    00 Stone Ledge Rd, Hillsdale, NY 12529

    Quiet location next to the Berkshires. Dead end road with a 12 acre parcel. Hiking trails throughout. Glorious views off the top. Great value. More land available.

    Tracy Tassinari Gabel Real Estate

    00 Stone Ledge Rd, Hillsdale, NY 12529
  • /36

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,040 Sq Ft

    695 Wolf Hill Rd, Hillsdale, NY 12529

    This country home is nestled on 8.7 private acres just five miles from the center of Hillsdale, this charming retreat offers the perfect blend of comfort, character, and natural beauty. A meandering driveway winds through the woods, leading to a welcoming cottage-style home surrounded by perennial gardens filled with native ferns and plantings.The inviting covered front porch opens to a

    Kimberly Baker BHHS Hudson Valley Properties

    695 Wolf Hill Rd, Hillsdale, NY 12529
  • /13

    $595,000

    • Land
    • 30 Acres
    • $19,833 per Acre

    0 Labranch Unit 20252234, Hillsdale, NY 12529

    Wonderful southern exposure on one of the most scenic byways in Columbia County. Large parcels and restrictive covenants on abutting land. High fields and ancient tree lines dotted with maples and old stone walls. Nice mix of open and wooded to tuck your home into the hedge row without another home in site. Distant views of Catamount Mountain. Close to Hawthorne Valley School and the Berkshires.

    Tracy Tassinari Gabel Real Estate

    0 Labranch Unit 20252234, Hillsdale, NY 12529
  • /21

    $346,900

    $53K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,381 Sq Ft

    9659 New York 22, Hillsdale, NY 12529

    Come see the new me!. I've had a face lift and you are sure to enjoy the gleaming hardwood floors and the updated kitchen with granite counters and new appliances. It's one level of easy living, and offers many wonderful features. Enjoy the spacious living room framed by a fireplace, or the cozy den which has one as well..The middle bedroom features sliders that open onto a deck, great to enjoy

    Tammy Molinski Coldwell Banker Advisor Realty

    9659 New York 22, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    400 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    400 Overlook Dr, Hillsdale, NY 12529
  • /22

    $365,000

    • 1 Bed
    • 1 Bath
    • 684 Sq Ft

    251 Overlook Dr, Hillsdale, NY 12529

    Are you dreaming of times spent tucked away in a rustic cabin, preferably wrapped in a cozy blanket in front of a roaring fireplace? Or maybe you're dreaming of barefoot in the stream that feds into the Green River and sunbathing with rays of sunshine beaming through the trees? Welcome to 251 Overlook, Hillsdale NY! Cira 1900 Cottage in the woods, built on the side of a mountain, on 4.5 Acres. A

    Margaret Bower Avenia Columbia County RE Specialist

    251 Overlook Dr, Hillsdale, NY 12529
  • /16

    $3,600,000

    • 4 Beds
    • 2 Baths
    • 3,200 Sq Ft

    90 W End Rd, Hillsdale, NY 12529

    For the first time on the market in 50 years, Underwood Farm, with its late 18th century cedar shake 3200 square foot salt box house, is 281 acres of primo hilltop exposure. Driving the property, the entire expanse is the high ground between West End Road and Rockledge Road with its equal parts woods, open meadows and fields with the rolling Taconics to the East. Below, the neighborhood is

    Parker Meyer Four Seasons Sotheby's Int.

    90 W End Rd, Hillsdale, NY 12529
  • /19

    $850,000

    • Land
    • 150 Acres
    • $5,667 per Acre

    0 Overlook Dr, Hillsdale, NY 12529

    Situated in Hillsdale, this extraordinary 150-acre hilltop offers an opportunity to create a private or legacy estate. Rising to over 1,300 feet, the parcel provides for sweeping panoramic views of the Berkshires and Taconic Range. Established logging roads and trails wind through the landscape past historic stone walls, dramatic rock outcroppings, seasonal streams and waterfalls. Combined with

    MATTHEW CAREY Rouse + Co Real Estate

    0 Overlook Dr, Hillsdale, NY 12529
  • /20

    $299,000

    $26K PRICE DROP
    • Land
    • 22.84 Acres
    • $13,091 per Acre

    0 County Route 21, Hillsdale, NY 12529

    Welcome to DREAMLAND.Set along a quiet country road, this exceptional 22 acre parcel offers the rare combination of privacy, curated natural beauty, and effortless access from New York City. Just minutes from the Taconic State Parkway, the property is ideally positioned for seamless weekend escapes or full-time living. A sun-drenched open meadow--perfectly oriented for southern

    Pamela King-Belfor Four Seasons Sotheby's Int.

    0 County Route 21, Hillsdale, NY 12529
  • /58

    $3,300,000

    • 4 Beds
    • 3 Baths
    • 5,760 Sq Ft

    124 Syre Ln, Hillsdale, NY 12529

    PRIVATE & QUIET ~ 124 Syre Lane, Hillsdale NYFederal Style Colonial home in Hillsdale, perched on the top of the mountain, pairing historical accuracy with state-of-the-art modern conveniences. This stately country home offers unparalleled, endless views in every direction of the valley and Catskill Mountains. Offering Immeasurable beauty, from every window and large back deck, perfect for

    Margaret Bower Avenia Columbia County RE Specialist

    124 Syre Ln, Hillsdale, NY 12529
  • /37

    $695,000

    New Construction
    • 3 Beds
    • 3 Baths
    • 1,824 Sq Ft

    30 Ridge Ln, Hillsdale, NY 12529

    Offering privacy, quality construction, and an ideal location. Set in the heart of the Roe-Jan region of the Hudson Valley and at the edge of the Berkshires, this home is tucked privately among mature trees on nearly eight acres while remaining close to the center of town. Recently constructed by one of the region's top builders, the residence was designed with both quality and longevity in mind.

    John Barbato Compass, Hillsdale

    30 Ridge Ln, Hillsdale, NY 12529
  • /58

    $949,900

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    2955 New York 23, Hillsdale, NY 12529

    Steeped in Hillsdale's rich history, this extraordinary property began its life as one of the area's original grist mills, situated in the area of Hillsdale once known as Murray's Corner. Thoughtfully transformed over the years into a distinctive residence, it seamlessly blends historic character with the tranquility of a private country retreat. Set on 8.7 enchanting acres, the property feels as

    Jason Walch Coldwell Banker Advisor Realty

    2955 New York 23, Hillsdale, NY 12529
  • /33

    $890,000

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    49 Knapp Hollow Ln, Hillsdale, NY 12529

    On 5 park-like acres this well maintained and thoughtfully designed home overlooks a tranquil pond and offers a serene getaway. Designed by architect Dennis Wedlick to maximize space and ease of living the home features 3-4 bedrooms and 3 full baths of which one is a separate guest suite. A renovated kitchen and updated bathrooms blend seamlessly with gleaming wood floors. A striking double sided

    marylou Kersten COPAKE LAKE REALTY CORP.

    49 Knapp Hollow Ln, Hillsdale, NY 12529
  • /43

    $795,000

    • 3 Beds
    • 2.5 Baths
    • 2,400 Sq Ft

    65 Meadow Ln, Hillsdale, NY 12529

    With a view as far as the eye can see, 65 Meadow Lane, Hillsdale never fails to amaze from sunrise to sunset, as a full moon lights up your bedroom; hawks fly past wandering clouds, the fiery yellow and burnt red leaves of autumn and the pine trees dripping with snow like confectionary sugar in a winter wonderland. The only sounds you hear are woodpeckers and wild turkeys and your heartbeat

    Margaret Bower Avenia Columbia County RE Specialist

    65 Meadow Ln, Hillsdale, NY 12529
  • /31

    $725,000

    Open Sat 10AM - 1PM
    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    2999 New York 23, Hillsdale, NY 12529

    2999 Route 23, Hillsdale, New York - Historic Country Estate on 12.5 Acres Step into a piece of living history with this beautifully preserved 1915 home, perfectly situated on a private 12.5-acre parcel in the heart of the Berkshires. Offering four generous bedrooms and three baths (2 full, 1 Half), this classic residence blends timeless charm with everyday comfort, creating an ideal setting for

    Tyler Bervy Stone House Properties, LLC

    2999 New York 23, Hillsdale, NY 12529
  • /34

    $649,000

    $70K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 1,475 Sq Ft

    81 Black Grocery Rd, Hillsdale, NY 12529

    On a quiet country road, sit's the prettiest sunshine yellow house you've ever seen.Welcome to a property where outdoor splendor and indoor comfort merge seamlessly, where everything has been taken care of, and all you need to do is arrive and exhale. Rolling hills and open farmland stretch out before you, and they're all yours to enjoy.Inside, the dining room flows into an open kitchen

    Shaina Marron Houlihan Lawrence Inc.

    81 Black Grocery Rd, Hillsdale, NY 12529
  • /66

    $290,000

    • Land
    • 40.25 Acres
    • $7,205 per Acre

    00WTP Anthony St, Hillsdale, NY 12529

    Located within the Town of Hillsdale itself, this unique 40.25± acre offering presents a rare opportunity to own a sizable tract of land in one of Columbia County's most desirable communities. While the property enjoys immediate access to the restaurants, shops, services, and amenities that make Hillsdale such a sought-after destination, its layout and surrounding landscape create a surprisingly

    Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

    00WTP Anthony St, Hillsdale, NY 12529

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