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Homes for Sale in 12529

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  • /44

    $1,475,000 New Construction

    • 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. A legal third bedroom on the

    John Barbato Compass, Hillsdale

    501 Birch St, Craryville, NY 12521
  • /77

    $1,695,000

    • 4 Beds
    • 3 Baths
    • 2,608 Sq Ft

    46 Collins St, Hillsdale, NY 12529

    Welcome to Nobletown Farmhouse, a circa 1850 home on 2+ peaceful acres in prime Hillsdale, on one of Columbia County's prettiest country roads. This beautifully updated four-bedroom, three-bath antique farmhouse showcases the elegant proportions and craftsmanship of mid-19th century architecture, with designer finishes, modern systems, and a full complement of additional structures that make it a

    Anthony D'Argenzio Houlihan Lawrence Inc.

    46 Collins St, Hillsdale, NY 12529
  • /40

    $979,000

    • 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
  • /37

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,574 Sq Ft

    407 Lakeview Rd, Craryville, NY 12521

    A rare year-round Lakefront Opportunity on Copake Lake. Just 2 Hours from NYC -Charming Log Home with Private Dock and deck. Swim, boat, ski, and relax year-round at this lakefront home.Ideally located between Hudson and Great Barrington in the heart of the Hudson Valley-Berkshires region. Turn-key four-season log home with sweeping lake views, a 46-foot private waterfront deck and

    Maria DiSalvo Coldwell Banker Prime

    407 Lakeview Rd, Craryville, NY 12521
  • /32

    $875,500

    • 4 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    2999 New York 23, Hillsdale, NY 12529

    Classic Country Home with Pond, Pool & Barns Located just minutes from Catamount Ski Area, Hudson, NY, and Great Barrington, MA. Steeped in history and charm, this distinctive residence—believed to date back to the late 1800s—offers timeless character with thoughtful updates and plenty of space to enjoy country living.This 4 BR, 2.5 BA, 2,225± sq. ft. home is sited on 12+ acres. The rocking

    Lindsay Lebrecht Copake Lake Realty Corp.

    2999 New York 23, Hillsdale, NY 12529
  • /28

    $1,275,000

    • 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
  • /25

    $799,800 New Construction

    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    801 Rodman Rd, Hillsdale, NY 12529

    New listing in Hillsdale, set high on a quiet dirt road where privacy, peace, and panoramic views define your backdrop. Why wait a year and a half for a new house to be built? This brand-new construction is being sold as it stands today, as a blank unfinished canvas ready for you to make it your own. The structure is in place with a brand-new drilled well, septic system, and 200-amp electrical

    Michael Castellano Gilcrest Properties

    801 Rodman Rd, Hillsdale, NY 12529
  • /28

    $810,000

    • 6 Beds
    • 2 Baths
    • 2,998 Sq Ft

    60 Anthony St, Hillsdale, NY 12529

    1800s farm house. Just waiting for some TLC. This property consists of the main farm house. one very large barn. Addtional 3 out building. One of the back building contains an attractive apartment.The property butts up to the Harlem Valley Rail Trail. Walking distant to the Hamlet of Hillsdale. Including the Roe Jan Brewing Co. IGA, The Hillsdale House, The town park. Less then 5 min ride to

    Gerard Meenagh The Meenagh Group Realty

    60 Anthony St, Hillsdale, NY 12529
  • /44

    $1,295,000

    • 4 Beds
    • 3 Baths
    • 3,282 Sq Ft

    9960 New York 22, Hillsdale, NY 12529

    Step into a world of timeless charm and understated luxury with this impeccably restored 18th-century farmhouse, nestled on over 6 acres of landscaped lawns, flowering gardens, and river frontage along the trout-rich Roe-Jan Kill. The residence exudes warmth and authenticity, offering luminous interiors and inviting outdoor living spaces ideal for entertaining or quiet retreat.The grand

    Pamela King-Belfor Four Seasons Sotheby's Int.

    9960 New York 22, Hillsdale, NY 12529
  • /13

    $1,100,000

    • Land
    • 9.01 Acres
    • $122,087 per Acre

    197 Lk Rdg Ln, Copake Lake, NY 12521

    A special opportunity to enjoy lake living within a uniquely private setting. 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. The 9+ acres of Lot 8 embrace direct views of the Catskill mountains to the west, and

    John Barbato Compass, Hillsdale

    197 Lk Rdg Ln, Copake Lake, NY 12521
  • /6

    $199,000

    • Land
    • 33.31 Acres
    • $5,974 per Acre

    50 Dugway Rd, Hillsdale, NY 12529

    Create Your Own Vision.Escape to 33.31 acres of untouched beauty in Columbia County, NY, and close to Great Barrington, MA. 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. Over 1,677 feet of road frontage, and an old roadway that

    Jeffrey McKinney Beach & Bartolo Realtors

    50 Dugway Rd, Hillsdale, NY 12529
  • /23

    $290,000

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    9377 New York 22, Hillsdale, NY 12529

    WELCOME HOME to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a

    Ronald Green KW Mid-Hudson

    9377 New York 22, Hillsdale, NY 12529
  • /24

    $615,000

    • 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
  • /46

    $3,350,000

    • 4 Beds
    • 4 Baths
    • 4,000 Sq Ft

    411 Texas Hill Rd, Hillsdale, NY 12529

    411 Texas Hill Road is an exemplary portrait of a Mid-Century home, set on 40 private acres. The home is positioned on one of the highest points in Columbia County, with views of both the Taconic and the Helderberg ranges. Located just 20 minutes from Hudson and surrounded by all the wonderful amenities of the Hudson Valley. Set on a quiet one-lane, town-maintained road, this private sanctuary is

    Marina Tatistcheff Compass Greater NY LLC

    411 Texas Hill Rd, Hillsdale, NY 12529
  • /23

    $290,000

    • 2 Beds
    • 1 Bath
    • 925 Sq Ft

    9377 State Route 22, Hillsdale, NY 12529

    WELCOME HOME to this charming and stylishly updated retreat situated on a spacious, level lot in beautiful Hillsdale, NY! Offering a perfect blend of modern character and country appeal, this home is ideal for those looking for a peaceful getaway with fantastic outdoor space. As you arrive, the striking dark grey exterior, crisp white accents, and charming fenced-in front yard lead you to a

    Scott Zobre KW MidHudson

    9377 State Route 22, Hillsdale, NY 12529
  • /20

    $5,100,000

    • Land
    • 517 Acres
    • $9,865 per Acre

    4 W Hill Rd, Austerlitz, NY 12017

    517 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

    Michael Tellerday Houlihan Lawrence Inc.

    4 W Hill Rd, Austerlitz, NY 12017
  • /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

    $364,900

    • 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
  • /15

    $2,999,000

    • Land
    • 242 Acres
    • $12,393 per Acre

    00 Dugway Rd, Austerlitz, NY 12017

    242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

    Michael Tellerday Houlihan Lawrence Inc.

    00 Dugway Rd, Austerlitz, NY 12017
  • /31

    $1,695,000

    • Land
    • 127.1 Acres
    • $13,336 per Acre

    0 Mitchell St Unit 20251360, Hillsdale, NY 12529

    Mitchell St is one of the most picturesque roads in Hillsdale and this property has a beautiful gentleness to it. Comprising of three separate contiguous lots (35.2 acres, 43.1 acres and 48.8 acres per assessor); access comes in off the southern most lot (43.10) and meanders through the property by a pond site, open meadows, old fruit trees and views of the hills around. The middle lot takes you

    Jennifer Harvey Compass Greater NY LLC

    0 Mitchell St Unit 20251360, Hillsdale, NY 12529
  • /10

    $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
  • /36

    $595,000

    • 3 Beds
    • 2 Baths
    • 2,057 Sq Ft

    2657 State Route 23, Hillsdale, NY 12529

    Proudly offering one of Hillsdale's most iconic and enduring homes—an exquisite piece of the Hudson Valley's heritage, perfectly positioned at the crossroads between Hudson, NY and Great Barrington, MA. Set in the vibrant and historic hamlet center, this timeless 3-bedroom, 2-bathroom residence is simply beautiful colonial charm.Thoughtfully renovated from top to bottom, the home retains its

    John Barbato Compass, Hillsdale

    2657 State Route 23, Hillsdale, NY 12529
  • /13

    $325,000

    • Land
    • 49.91 Acres
    • $6,512 per Acre

    61 Dugway Rd, Hillsdale, NY 12529

    Discover Your Dream Retreat: 49+ Acres of Serenity and Potential!Nestled between the charming towns of Chatham, NY, and Great Barrington, MA, this stunning parcel of over 49 acres offers a unique blend of privacy and accessibility. With impressive road frontage on two roads, this property is easily accessible while still providing a tranquil escape.Imagine waking up to the soothing sounds of the

    Jeffrey McKinney Beach & Bartolo Realtors

    61 Dugway Rd, 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
  • /34

    $589,900

    • 3 Beds
    • 2 Baths
    • 2,300 Sq Ft

    66 Anthony St, Hillsdale, NY 12529

    This home on almost 4 acres with a private pond and scenic mountain and sunset views year-round, also abuts the Harlem Valley Rail Trail. It is withinwalking distance to the village of Hillsdale. Including the Roe Jan Brewing Co. IGA, the Hillsdale House, and the town park. Less then 5-min driveto Catamount; 25 min to Hudson NY, and 20 min to Great Barrington MA.

    Susan Calkins STONE HOUSE PROPERTIES, LLC

    66 Anthony St, Hillsdale, NY 12529
  • /23

    $495,000 New Construction

    • 3 Beds
    • 2 Baths
    • 1,375 Sq Ft

    217 Anthony St, Hillsdale, NY 12529

    A newly built home ideally located on the edge of the charming hamlet of Hillsdale, NY, this home offers the convenience of true walkability--just steps to everyday essentials including the local hardware store, grocery market, wine shop, post office, town hall, coffee shops, restaurants, and boutique shops. With 3-bedrooms and 2-bathrooms, the home spans approximately 1,350 square feet of modern

    John Barbato Compass, Hillsdale

    217 Anthony St, Hillsdale, NY 12529
  • /18

    $2,999,000

    • Land
    • 242 Acres
    • $12,393 per Acre

    2 Dugway Rd, Austerlitz, NY 12017

    242 ACRES. Country living and hunter's paradise within a stone's throw of the famous Berkshire and Catskill Mountains. This property is the perfect location for the active outdoorsman or nature enthusiast. With miles of forestry, trails, and privacy, excellent fishing, ATV, and Snowmobile trails in the area, making this a haven for year-round recreation. Private, level, sloping, and wooded, this

    Michael Tellerday Houlihan Lawrence, Inc.

    2 Dugway Rd, Austerlitz, NY 12017
  • /25

    $1,250,000

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

    161 Stagecoach Rd, Hillsdale, NY 12529

    Architecture meets nature in Hillsdale. A fully secluded getaway at the end of a private dead-end road on 7.3 pristine acres. This sunny 3-bedroom, 2-1/2 bath house is inspired by Scandinavian design and features 3 outdoor decks, with views of a spring-fed stream, a crystal clear pond, and deep green woodlands. Central AC for summer days and a wood stove for snowy nights. An ideal layout for

    Owen Davidson Brown Harris Stevens HV LLC

    161 Stagecoach Rd, Hillsdale, NY 12529
  • /11

    $319,000

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    15 Melvin Rd, Craryville, NY 12521

    Move right into this 1960 Copake Lake cottage with deeded lake rights! On a quiet road just a five minute walk to the lake is your quaint oasis lovingly restored in 2023. Upgrades include a new open concept kitchen, living and dining area. Bathroom completely remodeled with walk-in shower. Upgraded mechanicals include furnace, oil tank, hot water heater, well pump and plumbing. The backyard

    John Peterson THE TRUSS GROUP LLC

    15 Melvin Rd, Craryville, NY 12521
  • /27

    $690,000

    • 3 Beds
    • 2.5 Baths
    • 2,093 Sq Ft

    149 Julianna Dr, Copake, NY 12516

    This approximately 2,100-square-foot ranch is sited on ~10 acres within The Birches HOA. The home offers three bedrooms and two-and-a-half bathrooms, an eat-in kitchen, and a dining room that opens to the living room. Both a wood-burning fireplace and a wood stove provide warmth and character. The land is a standout feature, with established fruit-bearing trees and a fenced vegetable garden. An

    Lindsay Lebrecht Copake Lake Realty Corp.

    149 Julianna Dr, Copake, NY 12516
  • /24

    $347,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Colony Rd, Hillsdale, NY 12529

    Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake! Property

    Margaret Avenia COLUMBIA COUNTY REAL ESTATE SPECIALISTS LLC

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

    $1,250,000

    • 5 Beds
    • 3 Baths
    • 2,708 Sq Ft

    1 van Bueran Dr, Hillsdale, NY 12529

    Tucked away at Copake Lake! This fully renovated home is set on a private 5-acre lot and features an open floor plan with a spacious eat-in kitchen and large island, a dining area that seats 10, and a living room with a grand fireplace and custom built-in benches. French doors open to a large screened-in porch on a wrap-around deck, offering sweeping views of the surrounding landscape. A second,

    John Barbato Compass, Hillsdale

    1 van Bueran Dr, Hillsdale, NY 12529
  • /28

    $1,275,000

    • 1 Bed
    • 2 Baths
    • 1,700 Sq Ft

    401 Collins St Unit Stop 11, 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 Sotheby's Int.

    401 Collins St Unit Stop 11, Hillsdale, NY 12529
  • /19

    $225,000

    • 2 Beds
    • 2 Baths
    • 794 Sq Ft

    2227 County Route 21, Hillsdale, NY 12529

    Tucked away on over 17 serene, subdividable acres in the Town of Kinderhook, this rare offering includes a half-finished 2-bedroom home (a shell awaiting your vision) with a brand-new raised-bed septic system and drilled well (newer pump) & new pressure tank already in place. With frontage on two quiet country roads; County Route 21 and Fowler Lake Rd. this land is a mix of old stone walls,

    Michael Castellano Gilcrest Properties

    2227 County Route 21, Hillsdale, NY 12529
  • /21

    $1,650,000

    • 2 Beds
    • 2 Baths
    • 1,419 Sq Ft

    75 Upper Hollow Rd, Hillsdale, NY 12529

    A rare 193-acre estate in Austerlitz/Hillsdale, very close to the Berkshire border. The charming 3-bed cottage overlooks a pristine pond with a bordering creek. The wooded land has clearly marked and maintained hiking trails. Recently renovated, the cottage features an updated bathroom and an expanded living room, blending modern comfort with rustic charm. Geothermal heating and air conditioning

    Janet Kain The Kinderhook Group, Inc.

    75 Upper Hollow Rd, Hillsdale, NY 12529
  • /13

    $1,080,000

    • Land
    • 72 Acres
    • $15,000 per Acre

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529

    Picturesque farmland located close to the Village of Hillsdale, only 1.8 to Catamount Ski Area, and 9.5 miles to Great Barrington. Extensive road frontage, totaling 3979 feet on Yonderview Road and Route 23. Barn complex. This parcel is zoned RU in the Town of Hillsdale. Property currently enjoys an agricultural exemption. Survey available. Inspect Now!

    Robert D Ferris R. Ferris Real Estate, LLC

    0 Yonderview Rd Unit ONEH6300032, Hillsdale, NY 12529
  • /69

    $2,995,000

    • 4 Beds
    • 3 Baths
    • 3,641 Sq Ft

    88 Mac Brown Rd, Claverack-Red Mills, NY 12513

    Welcome to Wolverton Creative Compound, a 119-acre estate in Claverack, NY, offering total privacy, wide southern light, integrated live-work studios, and a large swimmable pond with pebble beach. The 1830s farmhouse features four bedrooms, two baths, original moldings and Dutch doors, a whole-house water filter, and a bright layout for indoor-outdoor living. A fully insulated studio barn is

    Anthony D'Argenzio Houlihan Lawrence

    88 Mac Brown Rd, Claverack-Red Mills, NY 12513
  • /17

    $499,000

    • Land
    • 83.22 Acres
    • $5,996 per Acre

    50 - 61 Dugway Rd, Hillsdale, NY 12529

    Two Large Parcels Combine Offering Serenity & Great Potential. Located between the charming towns of Chatham, NY, and Great Barrington, MA, this 83 acre parcel offers you exceptional potential awaiting your vision, and ideal escape.Two adjoining proprieties come together to form this large property that is a unique blend of privacy and accessibility. Enjoy impressive road frontage on two roads

    Jeffrey McKinney Beach & Bartolo Realtors

    50 - 61 Dugway Rd, Hillsdale, NY 12529
  • /19

    $325,000

    • 2 Beds
    • 1 Bath
    • 736 Sq Ft

    81 SW Sw Colony Rd, Hillsdale, NY 12529

    Welcome to Copake Lake!! Sweet two-bedroom, one bath cottage, eat in kitchen, views of the lake from living room and one of the two bedrooms, nice big yard to enjoy outdoor fun. All appliances included. PLUS (As per Seller) water rights along that 20-foot stretch, a buyer may be able to agree with others in the area to extend the existing dock, which could be up to 60 feet into the lake! Property

    Margaret Bower Avenia Columbia County RE Specialist

    81 SW Sw Colony Rd, Hillsdale, NY 12529
  • /8

    $375,000

    • Land
    • 90 Acres
    • $4,167 per Acre

    0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529

    On a bucolic country by-way you will find this very private wooded hilltop parcel with Catskill Mountain views. Gorgeous mature timber and beautiful rocky outcrops dot this parcel. Access is via a brief right-of-way and along a pretty private lane. Note reduced taxes due to a power line easement to the rear of the property. Suitable for a single main residence.

    James Male HOUSE Hudson Valley Realty

    0 Harlemville Rd Unit 20254229, Hillsdale, NY 12529

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