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5-Bedroom Homes for Sale in Orange County NY with Private Pool

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  • /50

    $999,999

    • 5 Beds
    • 4 Baths
    • 4,116 Sq Ft

    50 Maple Ave, Goshen, NY 10924

    VINTAGE VIBES REVITALIZED. This isn't just a house, it's a statement. Nestled on 8.7 sprawling acres, this 5-bedroom, 4-bathroom magical mini-estate, built in 1760, fuses old-world charm with sleek modern vibes. Think timeless meets trendy in a way that feels effortless. The original wide-plank hardwood floors, exposed beams, and four fireplaces all tell stories from the past, while new-age

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    (845) 373-5801

    50 Maple Ave, Goshen, NY 10924
  • /40

    $1,249,000

    • 6 Beds
    • 4 Baths
    • 2,600 Sq Ft

    14 Robalene Dr, Goshen, NY 10924

    Finally a home that has everything you're looking for. Better than NEW CONSTRUCTION! All of the dreaded settlement issues that found in ALL new construction homes have been addressed here. Come enjoy this freshly painted "turn-key" home. This 5 yrs young, center hall colonial has it all. Nestled on a very private but extremely convenient cul-de-sac. Min to all your wants & needs. 5 min to the

    David White Owner Entry.com

    14 Robalene Dr, Goshen, NY 10924
  • /40

    $1,200,000

    • 5 Beds
    • 3.5 Baths
    • 4,570 Sq Ft

    10 Greenwich Ave, Central Valley, NY 10917

    "LE CHÂTEAU des VERTS": Unparalleled, Unprecedented and Poised...Inspired by castles on the rolling hills of the French countryside and perfectly perched here in the Hudson Valley, there's no wonder why this custom-built one-of-a-kind French Château is known to its neighborhood residents as 'The Castle on the Hill'. Incredibly designed inside and out with no detail spared, this 4,500+

    Micaela Stanaland Howard Hanna Rand Realty

    10 Greenwich Ave, Central Valley, NY 10917
  • /44

    $989,000

    • 5 Beds
    • 3 Baths
    • 3,926 Sq Ft

    10 Sutton Ln, Goshen, NY 10924

    Nestled on nearly 10 peaceful acres in the heart of scenic Goshen, this stunning Colonial offers the rare opportunity to embrace a life of beauty, balance, and ease. With 4 generous bedrooms, 3 full baths, and a bonus den/home office, this home is designed for the way you live today — where comfort meets elegance and every space tells a story. Step inside and immediately feel at home in the

    Jason Madison eXp Realty

    10 Sutton Ln, Goshen, NY 10924
  • /48

    $969,999

    • 7 Beds
    • 5.5 Baths
    • 5,500 Sq Ft

    7 van Keuren Ave, Pine Bush, NY 12566

    Welcome to your dream property in the Pine Bush School District!!! This exceptional estate offers space, versatility, and privacy on just over 11 acres of beautifully maintained land. At the heart of the property is a classic colonial-style homeboasting 5 bedrooms and 3.5 bathrooms, with a total of approximately 3,600 square feet of living space. Whether you're entertaining guests or enjoying a

    Vincent Reda Keller Williams Realty

    7 van Keuren Ave, Pine Bush, NY 12566
  • /43

    $1,195,000

    • 8 Beds
    • 7 Baths
    • 5,625 Sq Ft

    10 Wyllys Ct, Rock Tavern, NY 12575

    Tucked away at the end of a quiet cul-de-sac, this stunning 8-bedroom, 7-bathroom Colonial mega-mansion offers more than 5,600 square feet of elegant living space on a level 2.2-acre lot. Built in 2005, the home features a flexible mother-daughter layout with two expansive kitchens, dual staircases to both the second floor and finished walk-out basement, and plenty of room for multigenerational

    Sal Rajput Joseph Baratta Company Realty

    10 Wyllys Ct, Rock Tavern, NY 12575
  • /40

    $1,199,000

    • 6 Beds
    • 4.5 Baths
    • 4,240 Sq Ft

    219 Maple Ave, Monroe, NY 10950

    Nestled atop nearly 2 acres of park like property, this 6 Bedroom 4.5 Bath Masterpiece is the essence of luxury. Once inside the Entry Foyer, you’ll be greeted to an open floor plan of nearly 6,000 square feet. The Living Room & banquet sized Dining Room will impress the most discerning buyers with custom millwork. Gleaming hardwood floors throughout flow into an welcoming Great Room providing an

    Ryan Sunden Your Home Sold Guaranteed Rlty

    219 Maple Ave, Monroe, NY 10950
  • /49

    $1,075,000

    • 5 Beds
    • 4.5 Baths
    • 4,997 Sq Ft

    3 Josephine Dr, Washingtonville, NY 10992

    Offered for the Very First Time – Meticulous Blooming Grove EstateWelcome to this stunning 5-bedroom, 4.5-bathroom custom home offering nearly 5,000sqft of living space, all set on 1.4 beautifully manicured acres in the heart of Blooming Grove. Perfectly maintained and thoughtfully designed, this exceptional property blends timeless craftsmanship with modern updates and resort-style

    Celina Rofer Howard Hanna Rand Realty

    3 Josephine Dr, Washingtonville, NY 10992
  • /41

    $899,000

    • 6 Beds
    • 4 Baths
    • 3,957 Sq Ft

    48 South St, Goshen, NY 10924

    Seller Financing Available!! Nestled in the coveted Village of Goshen in the heart of Orange County, this stunning estate combines historic charm with modern luxury. Set on a sprawling 1.7-acre lot, the home offers 4,000 square feet of elegantly designed living space, featuring six bedrooms, four bathrooms, hardwood floors, three wood-burning fireplaces, a private home office, and an expansive

    Kelvin Cordero Curasi Realty, Inc.

    48 South St, Goshen, NY 10924
  • /33

    $924,000

    • 5 Beds
    • 4 Baths
    • 4,366 Sq Ft

    1010 Pine View, New Windsor, NY 12553

    HIGHLY MOTIVATED SELLER, PRICE NEGOTIABLE..."Home Sweet Home", Almost an acre, YES HONEY STOP THE CAR!!! CORNWALL SCHOOLS and right around the corner from all stores, grocery and Woodbury Commons Shopping Outlets plus gas stations. Not to mention you are 5 minutes from all MAJOR HIGHWAYS INCLUDING PALISADES PKWY! Salisbury Mills TRAIN station as well!!! For a peaceful ride into Hoboken then NYC!

    Tameeka Williams KFortuna All Aspects Realty

    1010 Pine View, New Windsor, NY 12553
  • /37

    $999,999

    • 5 Beds
    • 3 Baths
    • 4,958 Sq Ft

    75 Monahan Rd, Port Jervis, NY 12771

    Discover the essence of Hudson Valley living with this extraordinary property! Nestled in a serene, wooded landscape, this home has almost 5,000 sqf, 5 bedrooms, 3 bathrooms, 2 bonus rooms (use as gym, 2nd office, etc.) and an office. This contemporary home offers unparalleled privacy and a canvas to create your dream lifestyle. Enjoy breathtaking sunrises and sunsets with perfect lighting

    Christian Zube Realty Executives Exceptional

    75 Monahan Rd, Port Jervis, NY 12771
  • /45

    $749,000

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

    254 Orrs Mills Rd, New Windsor, NY 12553

    Discover the Best of New Windsor & Cornwall – Right at Your Doorstep! Cornwall SchoolsWelcome to 254 Orrs Mills Road, where comfort, character, and convenience meet in this stunning Contemporary Colonial. Nestled in nature’s lush landscape, this spacious multi-level home offers scenic views from every angle, vaulted ceilings, and sunlit interiors enhanced by skylights and Andersen

    Valerie Moldow Howard Hanna Rand Realty

    254 Orrs Mills Rd, New Windsor, NY 12553
  • /50

    $585,000

    • 5 Beds
    • 3.5 Baths
    • 4,364 Sq Ft

    529 Prospect Hill Rd, Cuddebackville, NY 12729

    Traveling along a quiet county road and gradually ascending in elevation, you’ll arrive at your destination: 529 Prospect Hill Road – A Storied Hudson Valley Estate. Without question, this is one of the most captivating properties you will ever have the chance to own. The natural grounds boast varied topography and lush greenery, including the striking dawn redwood—gracefully positioned between

    Frank Muccari Cronin & Company Real Estate

    529 Prospect Hill Rd, Cuddebackville, NY 12729
  • /46

    $849,900

    • 5 Beds
    • 3 Baths
    • 3,485 Sq Ft

    284 Bull Mill Rd, Chester, NY 10918

    Monroe's Stunning Mini Mansion Awaits Its New Owner!This exquisite home offers everything you've been dreaming of in an ideal location. Step into this 5-bedroom, 3-bath residence featuring a beautiful double-height entrance and a striking palladium window, welcoming you with its elegant double-sided luxury staircase.Before heading upstairs, prepare to be impressed by the spacious chef's

    Jayne Mangieri Keller Williams Valley Realty

    284 Bull Mill Rd, Chester, NY 10918
  • /50

    $3,000,000

    • 5 Beds
    • 5 Baths
    • 3,732 Sq Ft

    94 Cliff Rd, Tuxedo Park, NY 10987

    Welcome to sun infused Hill House, created in 1988 by designer Geoffrey Bradfield for himself. Inspired by his visit to Villa Pisani outside Vicenza, the home is pleasingly symmetrical. From the entrance foyer, direct views of the infinity pool and Ramapo Mountains. To the right of the foyer is a bungalow chique den/bedroom. The entrance hall is flanked on the right by an emerald green "winter

    Anna Shaw Compass Greater NY, LLC

    94 Cliff Rd, Tuxedo Park, NY 10987
  • /42

    $849,000

    • 7 Beds
    • 3.5 Baths
    • 3,821 Sq Ft

    312 Rye Hill Rd, Monroe, NY 10950

    Come and experience the extraordinary, unparalleled opportunity that awaits you at 312 Rye Hill! This is a chance you certainly don't want to overlook. Nestled within stunning grounds and encircled by lush, green trees, this property offers a serene retreat where you can fully immerse yourself in the beauty of nature.As you step inside, you're greeted by a charming foyer adorned with a modern

    David Kraus MK Realty Inc

    312 Rye Hill Rd, Monroe, NY 10950
  • /36

    $839,000

    • 5 Beds
    • 4.5 Baths
    • 3,182 Sq Ft

    1 Cindy Ln, Highland Mills, NY 10930

    NEW!! Discover the epitome of luxury living in this magnificent, one-of-a-kind home!! Nestled in a highly sought-after neighborhood. This stunning property boasts an expansive layout, offering ample space for both relaxation and entertainment. The heart of the home is the magnificent kitchen, featuring elegant granite countertops that blend style and functionality, perfect for culinary

    Joseph Rosenfeld Flag Realty Group

    1 Cindy Ln, Highland Mills, NY 10930
  • /4

    $887,000

    • 5 Beds
    • 2 Baths
    • 2,000 Sq Ft

    5 Tappan Dr, Monroe, NY 10950

    Don't miss out on this opportunity to own your lakefront dream home situated on a quiet, half acre, cul-de-sac in the village of South Blooming Grove.You will be minutes away from major highways, close to supermarkets and everything this neighborhood has to offer. Whether you're lookingto move in, build you own dream home or invest, this is the home for you!

    Shalom Landau eRealty Advisors, Inc

    5 Tappan Dr, Monroe, NY 10950
  • /50

    $2,490,000

    • 6 Beds
    • 5.5 Baths
    • 5,450 Sq Ft

    395 Sarah Wells Trail, Goshen, NY 10924

    Twin Oaks is a one-of-a-kind gem located on one of the most picturesque roads in Orange County. Situated on a park-like 8.3 acre estate on the border of the Village of Goshen, the 5250sqft Victorian residence features 6 bedrooms, 5.5 bathrooms and recently has been extensively renovated and updated - while very tastefully maintaining its original charm and character. Receive and entertain your

    Joseph Paoli Howard Hanna Rand Realty

    395 Sarah Wells Trail, Goshen, NY 10924
  • /50

    $2,275,000

    • 5 Beds
    • 4.5 Baths
    • 7,200 Sq Ft

    560 Grand Ave, Newburgh, NY 12550

    Overlooking the Hudson River in the esteemed hamlet of Balmville, this Gothic Revival masterpiece, The Rest is a rare and remarkable offering—an enduring symbol of 19th-century architecture, masterfully adapted for modern living.Commissioned in the 1860s by Daniel Bennett St. John— Congressman, Senator, and a founding editor of The New York Times—this estate was brought to life by Frederick

    Zebee Amy Voss Julia B Fee Sothebys Int. Rlty

    560 Grand Ave, Newburgh, NY 12550
  • /35

    $649,900

    • 5 Beds
    • 4 Baths
    • 3,715 Sq Ft

    216 Maple Ave, Monroe, NY 10950

    A/O 6/30/2025 - Situated on a cul-de-sac street in the sought-after Round Lake community of Monroe, this 5BR/4BTH masterpiece is sure to impress the most discerning buyers. Upon entering the foyer you will be greeted to over 3,700 square feet of luxury space. The Formal Living Room is drenched in natural light flowing seamlessly into the banquet sized Dining Room. Next, imagine preparing your

    Ryan Sunden Your Home Sold Guaranteed Rlty

    216 Maple Ave, Monroe, NY 10950
  • /31

    $569,000

    • 5 Beds
    • 4 Baths
    • 2,504 Sq Ft

    19 Hilltop Place, Monroe, NY 10950

    This home is a true Mother daughter home and it can be legally rented as a two family property. Perfect for a big extended family that want to live next to each other or for investors who are looking for great rental income from the 2 units. The main level of this property consists of 4 bedrooms and 3 full baths. The kitchen has granite counter tops, stainless steel appliances and a large island

    Anita S. Cristiano HomeSmart Homes & Estates

    19 Hilltop Place, Monroe, NY 10950
  • /50

    $6,995,000

    • 8 Beds
    • 9 Baths
    • 8,250 Sq Ft

    22 Brook Farm Rd, Tuxedo Park, NY 10987

    Upon entering Tuxedo Park and driving past its historic stone gatehouse and original architectural splendor, one drives around Tuxedo Lake and over a stone bridge with a babbling brook to arrive at Brook Farm. About 55 minutes to Manhattan and on the train line! Brook Farm is an ultra-luxurious, tranquil estate on six acres combining minimalist style and elegance with the serene aesthetic of an

    Richard Ellis Ellis Sotheby's Intl Realty

    22 Brook Farm Rd, Tuxedo Park, NY 10987
  • /26

    $880,000

    • 5 Beds
    • 3.5 Baths
    • 3,456 Sq Ft

    87 Mill St, Wallkill, NY 12589

    Welcome to your private Hudson Valley retreat! This stunning 4-bedroom colonial is set on two separate parcels totaling 32.7 acres—a rare offering that includes a 29.8-acre main parcel and a 2.9-acre adjacent lot, providing endless possibilities and privacy.A long, gated driveway leads to the elegant home, nestled in a serene and lush setting ideal for those seeking peace and space. The spacious

    Amy Liu Douglas Elliman Real Estate

    87 Mill St, Wallkill, NY 12589
  • /50

    $849,000

    • 5 Beds
    • 3.5 Baths
    • 4,462 Sq Ft

    140 Powelton Cir, Newburgh, NY 12550

    This stunning ranch-style home offers 4,460 square feet of thoughtfully designed living space on a beautifully landscaped one-acre lot. Located just minutes from major highways and shopping. Featuring 5 spacious bedrooms and 4 bathrooms, and a completely remodeled primary bedroom with a professionally designed en-suite bathroom and dual walk-in closets.Inside, you’ll find multiple living areas

    Abdelrahim Ibrahim Coldwell Banker Realty

    140 Powelton Cir, Newburgh, NY 12550
  • /35

    $689,000

    • 6 Beds
    • 3.5 Baths
    • 2,948 Sq Ft

    669 Mountain Rd, Middletown, NY 10940

    Nestled in the Minisink School District | 6 bedrooms, |3 bathrooms| chef’s kitchen| perfect for those who love to cook and entertain. The double-sided fireplace*adds a cozy touch, while the inground pool makes it an ideal retreat.Set on 3.38 acres the home is surrounded by lush greenery, providing a peaceful and private atmosphere. The Colonial and Contemporary architectural style blends

    Michelle Gruberger Real Estate Circuit Inc

    669 Mountain Rd, Middletown, NY 10940
  • /50

    $1,375,000

    • 12 Beds
    • 9 Baths
    • 8,856 Sq Ft

    23 Maple Rd, Cornwall On Hudson, NY 12520

    Step into the past & dance into your future in this singular marvel of what can be enjoyed as a family compound or purposed as an investment for you to create a business or add to your portfolio. Have you dreamed of owning an assemblage of homes (or homes away from home) that sits just over an an hour from the city? You can own it all. An 8 bedroom main house to gather with family and friends, a

    Michael Taraboulos Christie's Int. Real Estate

    23 Maple Rd, Cornwall On Hudson, NY 12520
  • /50

    $1,375,000

    • 8 Beds
    • 4.5 Baths
    • 6,594 Sq Ft

    23 Maple Rd, Cornwall On Hudson, NY 12520

    Step into the past & dance into your future in this singular marvel of what can become your family compound or an opportunity to create a lifestyle that combines` business with country living. Have you dreamed of owning a a home (or home away from home) that is just over an an hour from the city? A place to gather with family and friends….a place to swim in your own pool, play tennis on your own

    Michael Taraboulos Christie's Int. Real Estate

    23 Maple Rd, Cornwall On Hudson, NY 12520
  • /49

    $799,000

    • 6 Beds
    • 3.5 Baths
    • 3,439 Sq Ft

    97 Ludlam Rd, Monroe, NY 10950

    Are you looking for an easy summer home where you can host and relax in privacy yet stay close by? Located on a quiet road, This house features six bedrooms including 18 beds! Also has an additional detached double garage for your potential. Enjoy the fully private backyard featuring lush greenery, Amish made playset with a gated Olympic size pool. Also a separate pool house for changing, shower

    Avi Samet Avion

    97 Ludlam Rd, Monroe, NY 10950
  • /27

    $399,999

    • 5 Beds
    • 3 Baths
    • 3,024 Sq Ft

    75 Main St, Otisville, NY 10963

    Welcome to your dream home in the charming village of Otisville, New York! This spacious 5-bedroom, 3-bathroom residence offers a rare and versatile side-by-side mother-daughter layout — perfect for multi-generational living or anyone seeking separate yet connected spaces. Each side features its own private entrance and distinct living areas, providing comfort, privacy, and flexibility for modern

    Kewin Garabito eXp Realty

    75 Main St, Otisville, NY 10963
  • /40

    $845,000

    • 5 Beds
    • 3.5 Baths
    • 3,525 Sq Ft

    423 Jackson Ave, New Windsor, NY 12553

    Nestled on this 1.4 acre picturesque lot sits this Grand Center Hall Colonial. Step in to find so much space to accommodate your entire family even to include your extended family or In-Home Office. Enter through your front door to find your Formal Dining & Living Rooms with crown molding, Floor to Ceiling windows & Custom Pillars. A tiled ½ bath has been renovated to perfection. To the back

    Michele Rios BHHS Hudson Valley Properties

    423 Jackson Ave, New Windsor, NY 12553
  • /50

    $2,895,000

    • 5 Beds
    • 6 Baths
    • 6,435 Sq Ft

    16 State School Rd, Warwick, NY 10990

    Longhouse Farm is a breathtakingly restored farmhouse that seamlessly blends historic elegance with luxurious modern upgrades. Nestled on over 11 acres of scenic beauty, this equestrian estate offers a perfect balance of sophistication and tranquility. The property includes a stunning main house, a charming guest house (which comes fully furnished), a 9-stall barn, and a 4-stall run-in

    Jason Kerwar William Raveis-New York, LLC

    16 State School Rd, Warwick, NY 10990
  • /44

    $649,000 Open Sat 1PM - 4PM

    • 5 Beds
    • 2.5 Baths
    • 2,988 Sq Ft

    52 Gregory Dr, Goshen, NY 10924

    Welcome to this bright and spacious 5-bedroom, 3-bathroom colonial home nestled in the desirable Spring Glen neighborhood of Goshen. Spanning 2,988 square feet, this residence boasts an inviting layout perfect for modern living and entertaining. The main floor includes an additional versatile bedroom ideal for an office, in-law suite, or nanny’s quarters. Enjoy cozy evenings by the fireplace and

    Adrian Burgos John J Lease REALTORS Inc

    52 Gregory Dr, Goshen, NY 10924
  • /49

    $2,695,000

    • 10 Beds
    • 5.5 Baths
    • 6,090 Sq Ft

    157 Arcadia Rd, Goshen, NY 10924

    This stunning 8100 plus square foot stone and stucco Manor Home sits on 5.1 park like acres has been meticulously updated to blend historic charm with modern convenience. This estate offers a unique opportunity for both luxurious living. The home has been extensively renovated, featuring energy-efficient geothermal heating and central air, all-new plumbing and bathrooms, updated insulation, a new

    Mary Rice Israelski Howard Hanna Rand Realty

    157 Arcadia Rd, Goshen, NY 10924
  • /29

    $650,000

    • 5 Beds
    • 2 Baths
    • 1,872 Sq Ft

    27 Rose Hill Park, Cornwall, NY 12518

    Beautifully-maintained and updated raised ranch home on a quiet cul-de-sac in Cornwall! Featuring over a half acre of land and a gorgeous fenced in-ground pool, mature landscaping, 5 bedrooms and ample storage, 2 full bathrooms, new heating/water systems, new flooring, open concept kitchen with mobile island and granite counters, new appliances including oven/range, refrigerator, dishwasher and

    John Willis Howard Hanna Rand Realty

    27 Rose Hill Park, Cornwall, NY 12518
  • /58

    $699,000

    • 12 Beds
    • 11 Baths
    • 5,004 Sq Ft

    5 Wawayanda Place, Middletown, NY 10940

    Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 11 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

    Jamie Sittner Oxford Property Group USA

    5 Wawayanda Place, Middletown, NY 10940
  • /36

    $915,175

    • 5 Beds
    • 5 Baths
    • 3,130 Sq Ft

    30 Werner Ave Unit MAIN HOUSE, Florida, NY 10921

    This is the ULTIMATE OPPORTUNITY to own an INCOME PRODUCING PROPERTY and live in a LUXURIOUS HOME with an open, flowing floor plan with plenty of private living spaces for multigenerational living, flexible entertaining or home office spaces with the added BONUS of a legal 1 bedroom cottage which currently rents for $1700.00 a month to cover your taxes on this GRAND ESTATE.The 1st floor of the

    Patricia Brady Keller Williams Realty

    30 Werner Ave Unit MAIN HOUSE, Florida, NY 10921
  • /49

    $5,499,000

    • 6 Beds
    • 5 Baths
    • 3,762 Sq Ft

    349 Sarah Wells Trail, Goshen, NY 10924

    The nicest Equine Boarding Facility in Orange County could be yours; located on 103+ Acres with ample privacy, multiple residential houses, 3 separate Garages, a 100' By 200' Indoor Steel Equestrian Riding Arena and 30-Stall Double-Breezeway Horse Barn. The State of the art Horse Barn features a heated riders lounge, tack room and full hayloft. Horse owners know what a flex 14' by 14' horse

    Deb Cor Exclusively Equine Prop LLC

    349 Sarah Wells Trail, Goshen, NY 10924
  • /2

    $525,000

    • 6 Beds
    • 2 Baths
    • 2,100 Sq Ft

    10 Congress Dr, Washingtonville, NY 10992

    Opportunity awaits in this expansive 6-bedroom, 2-bathroom home nestled in the desirable community of Washingtonville. With generous square footage, a brand-new renovated kitchen, and a large backyard, this property offers incredible potential for families, investors, or those looking to create their dream home.The heart of the home is the stunning new kitchen, featuring a large center island,

    Danielle Russodivito New and Modern Group, LLC

    10 Congress Dr, Washingtonville, NY 10992
  • /2

    $1,300,000

    • 5 Beds
    • 5 Baths
    • 5,113 Sq Ft

    11 Hedges Rd, Warwick, NY 10990

    Property to be placed at auction xomeBidding event start date - 5/31/25Bidding end date - 6/3/25

    Andrea Rose Keller Williams Hudson Valley

    11 Hedges Rd, Warwick, NY 10990
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