Orange County NY Homes for Sale with Private Pool

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  $625,000 Pre-Foreclosure

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

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 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 Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
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  /37

  $474,999

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

  10 Congress Dr, Washingtonville, NY 10992

  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 investors, or those looking to create their dream home. The heart of the home is the stunning new kitchen, featuring a large center island, modern cabinetry, and updated appliances –

  Danielle Russodivito New and Modern Group, LLC

  10 Congress Dr, Washingtonville, NY 10992
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  /50

  $699,000

  • 3 Beds
  • 3 Baths
  • 3,000 Sq Ft

  360 Prospect Rd, Chester, NY 10918

  B"H Grab this opportunity!!! Cozy Home in great condition sitting on a 3.2 ACER Property!!! Enjoy the above ground pool !!!Wonderful neighborhood and calm area. Open living room with wood burning fireplace, The kitchen offers a breakfast bar, Center island, Stainless steel appliances, Multiple counter space and cabinets. Finished lower level with a Den/office, Family room and full bathroom.

  Joseph Mendlowitz eRealty Advisors, Inc

  360 Prospect Rd, Chester, NY 10918
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  /27

  $700,000

  • 6 Beds
  • 2 Baths
  • 2,216 Sq Ft

  121 Renwick St, Newburgh, NY 12550

  3-PROPERTY PACKAGE SALE...Next to each other on a corner location with all municipal services. Affordable two family brick 3-bedrooms each unit attached home on two levels in City of Newburgh with small rear yard/parking, sidewalks and all municipal services. Walking distance to George Washington Headquarters, Newburgh Brewing Company, a variety of restaurants & shops, the Newburgh waterfront &

  George Koudounas RE/MAX Benchmark Realty Group

  121 Renwick St, Newburgh, NY 12550
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  $629,000

  • 5 Beds
  • 2 Baths
  • 2,368 Sq Ft

  52 Woodland Rd, Highland Mills, NY 10930

  Wow! This enlarged Highland Mills raised ranch boasts 5 bedrooms and two full baths situated on a corner lot next to designated Town green space. Its grassy front, back and side yards contain mature trees and perennial plants that create a serene, relaxing environment. Inside the home is a lovely living room with a newer Anderson bow window that lets in tons of afternoon light. There is original

  Derek Greene Greene Realty Group

  52 Woodland Rd, Highland Mills, NY 10930
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  /47

  $499,000 Open House 2/14

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  14 Rdean Place, Middletown, NY 10940

  Nestled in a quiet Residential neighborhood of Middletown sits this spacious 3 bedroom, 2.5 bath Gem ready for its new owners! A front porch with a brick facade leads you to the front door entrance of your forever home. Enter into an oversized formal living room with vaulted ceilings on one side and a formal dining room with natural window light on the other with hardwood floors throughout. The

  Sandra Arnez Keller Williams Hudson Valley

  14 Rdean Place, Middletown, NY 10940
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  /37

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  2066 Route 6, Middletown, NY 10940

  Set on over 5 acres and beautifully landscaped, this inviting home delivers space, comfort, and resort-style living at home. A true backyard oasis designed for relaxation and entertaining. Step outside to your private retreat featuring an above-ground heated pool with surrounding deck, an extended patio with a pergola swim-up bar, and multiple spaces to gather, unwind, and enjoy the outdoors. A

  Juliska Martino Compass Greater NY, LLC

  2066 Route 6, Middletown, NY 10940
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  /50

  $829,500

  • 4 Beds
  • 2.5 Baths
  • 3,413 Sq Ft

  83 High Hope Dr, Otisville, NY 10963

  This spectacular home which can be used as a weekend retreat or an ideal home nestled on over 25 private acres with a serene pond, offering unmatched peace, beauty, and breathtaking eastern views of the sunrise from its expansive wrap-around porch. The property invites you to take walks or hikes through the woods and enjoy the sights and sounds of nature in complete privacy. Inside, custom

  Gail Rachlin Keller Williams Hudson Valley

  83 High Hope Dr, Otisville, NY 10963
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  /39

  $948,888

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

  14 Robalene Dr, Goshen, NY 10924

  Better-than-new 6BR/4BA Colonial just over 5yrs young with over $400K in upgrades and resort-style amenities. Gourmet kitchen with granite countertops, stainless steel appliances, hardwood floors, and fireplace. First floor also includes dining room, flex room/den/playroom or possible 6th BR and full bath. Second floor boasts primary suite with custom walk-in closet and spa bath featuring steam

  David White Owner Entry.com

  14 Robalene Dr, Goshen, NY 10924
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  /50

  $1,850,000

  • 5 Beds
  • 5.5 Baths
  • 6,348 Sq Ft

  7 Paiges Way, Warwick, NY 10990

  Discover this stunningly appointed 5-bedroom, 5.5-bath home nestled on 4.1 acres in beautiful Warwick, New York. This elegant and turnkey residence is perfect for both comfortable living and entertaining guests. Enjoy the luxurious in-ground pool, expansive living areas, and a beautifully serene yard. The lower level features gaming area, a custom bar, and a luxurious bathroom, creating an ideal

  Steve Vinti Weichert Realtors

  7 Paiges Way, Warwick, NY 10990
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  /48

  $649,900

  • 5 Beds
  • 2 Baths
  • 2,220 Sq Ft

  33 Winchester Dr, Monroe, NY 10950

  Located in the desirable Monroe-Woodbury School District, this classic 2,220 sq ft colonial offers a rare combination of space, comfort, and future potential. Set on a gentle hill in a picturesque, sidewalk-lined neighborhood, the property features four spacious bedrooms, two bathrooms, and a well-balanced layout that includes a formal dining room, a living room, and a separate family room. The

  Dennis Clark Howard Hanna Rand Realty

  33 Winchester Dr, Monroe, NY 10950
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  /27

  $514,900

  • 3 Beds
  • 2 Baths
  • 972 Sq Ft

  32 Highland Ave, Warwick, NY 10990

  First time on the market in 35 years! This well-maintained ranch home offers pride of ownership throughout. Featuring gleaming hardwood floors across the entire home, this property includes three spacious bedrooms and two full bathrooms, providing comfortable one-level living. Possible Mother/Daughter house. Step outside to enjoy a private deck and above-ground pool, perfect for relaxing or

  Karen Teverbaugh Maureen B Maloney

  32 Highland Ave, Warwick, NY 10990
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  /50

  $699,999

  • 5 Beds
  • 4 Baths
  • 3,858 Sq Ft

  254 Orrs Mills Rd, New Windsor, NY 12553

  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

  Bryan Dale eXp Realty

  254 Orrs Mills Rd, New Windsor, NY 12553
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  /17

  $439,999

  • 3 Beds
  • 2.5 Baths
  • 1,976 Sq Ft

  9 Carpenter Rd, Port Jervis, NY 12771

  This spacious 3-bedroom, 2.5-bath ranch offers 1,976 sq. ft. of one-level living on a beautiful corner lot in Deer Park, just minutes from Port Jervis. Enjoy the charm of a mid-century layout with modern updates including a new roof (2021), mini-split A/C units (2023), updated 200-amp electrical service, new well pump, and a pellet stove serviced yearly for efficient heating. The property

  Rachel Hunt Realty Promotions Inc

  9 Carpenter Rd, Port Jervis, NY 12771
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  /24

  $530,000

  • 4 Beds
  • 2 Baths
  • 1,322 Sq Ft

  5 Berkley Terrace, Monroe, NY 10950

  Lake Rights! Low Taxes! Welcome home to this lovely cape, beautifully situated on a double lot allowing for plenty of yard space for peace and privacy. This home features 4 bedrooms and 2 full bathrooms with a large eat-in kitchen, wood floors and a spacious unfinished, walk-out basement. Walk-out from the kitchen onto a lovely deck for grilling, dining and relaxing as you take in the tree-top

  Layla Rose Boyles Century 21 Realty Center

  5 Berkley Terrace, Monroe, NY 10950
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  /41

  $169,548 Open Fri 11AM - 4PM

  • 2 Beds
  • 1 Bath
  • 400 Sq Ft

  197 Wheeler Rd Unit 101, Florida, NY 10921

  Serenity Ridge Mountain Club is Your Home Away from Home...Where Life Slows Down Enough for Joy to Catch Up. Embrace the best of the outdoors without giving up the comforts you love. Serenity Ridge blends nature, recreation, and relaxation into one unforgettable escape. At Serenity Ridge, your Mountain Cottage is designed for seasonal enjoyment—including The Warwick model, which features 2

  Vanessa Wight BHG Real Estate Green Team

  197 Wheeler Rd Unit 101, Florida, NY 10921
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  /28

  $694,500

  • 4 Beds
  • 2.5 Baths
  • 2,372 Sq Ft

  13 Hopkins Ct, Washingtonville, NY 10992

  Property back on market due to buyer's financing falling through. Located in the desirable Highgrove community in Washingtonville, this stunning colonial sits on a premium tree-lined homesite with sun-drenched rooms throughout. Its southern exposure fills every space with beautiful natural light and the open floor plan offers a seamless flow, ideal for both everyday living and entertaining.

  TINA TOWNSEND BHHS Hudson Valley Properties

  13 Hopkins Ct, Washingtonville, NY 10992
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  /39

  $430,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,704 Sq Ft

  13 Butternut Ct, Highland Mills, NY 10930

  If the roads are icy, call for a private tour. A contemporary and updated 3-story townhouse with an attached garage. Upgrades include: Anderson windows, hardwood floors, granite countertops, kitchen appliances (stainless steel), recessed lighting, and millwork surrounding the wood-burning fireplace. The updated kitchen was refreshed with granite counters, tile backsplash, open shelving, stainless

  Lynda Hoss Weichert Realtors

  13 Butternut Ct, Highland Mills, NY 10930
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  /10

  $1,095,000

  • 4 Beds
  • 2.5 Baths
  • 2,311 Sq Ft

  11 Cliff Ct, Monroe, NY 10950

  Welcome to your private retreat in the heart of Monroe! Tucked into a serene neighborhood, this charming 4 bedroom, 2.5 bath offers the perfect blend of indoor comfort and outdoor enjoyment. Set on a beautifully landscaped lot, the home greets you with a long driveway leading to the attached 2 car garage. Enter to find a bright and inviting home with hardwood floors, recessed lighting and a cozy

  Avrahom Lewinson Keller Williams Realty

  11 Cliff Ct, Monroe, NY 10950
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  /20

  $599,000

  • 3 Beds
  • 2 Baths
  • 2,180 Sq Ft

  252 Round Hill Rd, Florida, NY 10921

  This three-bedroom farmhouse is situated on 2.1 acres and features a large barn, an in-ground swimming pool, a basketball court, gardens, and fruit trees. The kitchen boasts granite countertops, ample cabinet space, a large pantry, stainless steel appliances, and a center island with a wet bar. A breakfast nook, featuring French doors, leads to a deck that overlooks the 20x40 in-ground pool,

  Jeanmarie Valentin HomeSmart Homes & Estates

  252 Round Hill Rd, Florida, NY 10921
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  $2,999,999

  • 4 Beds
  • 4.5 Baths
  • 4,461 Sq Ft

  101 Mountain Lodge Rd, Washingtonville, NY 10992

  "Sunset Lodge," carefully curated and impeccibly maintained, is available for only the third time. This once in a lifetime estate comprises 38 acres, yet is only 7 minutes from Metro North NJ Transit. Exquisite main home, two ponds, 20 acres fenced (+10 wooded acres), a six stall horse barn with apartment, spectacular warm weather entertaining area with stunning 18 x 65 foot infinity pool, 8

  Susan Rost Tux Park Towne & Country

  101 Mountain Lodge Rd, Washingtonville, NY 10992
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  /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
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  /50

  $3,195,000

  • 4 Beds
  • 6 Baths
  • 7,669 Sq Ft

  12 Mountain Brook Rd, Cornwall, NY 12518

  Welcome to Mountain Brook Estate, an ultra-private, luxurious mountaintop retreat encompassing 26+ acres on one of the highest elevations in the Hudson Valley. An hour from New York City and minutes from West Point, this nearly 8,000 square foot contemporary estate has been meticulously renovated to showcase commanding views of the Hudson River, Storm King Mountain, and the surrounding Catskill

  Jake Garay Serhant LLC

  12 Mountain Brook Rd, Cornwall, NY 12518
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  /18

  $299,000

  • 2 Beds
  • 1.5 Baths
  • 1,072 Sq Ft

  3120 Whispering Hills, Chester, NY 10918

  Welcome to this charming 2-bedroom condo in the desirable Whispering Hills community! This unit faces green space and trees for added privacy as well as comfortable living spaces. The home features a cozy living room with a fireplace, a dining area, and a full kitchen ready for everyday meals or weekend entertaining. Enjoy the convenience of having your own in-unit washer and dryer, plus a

  Bente Brown John J Lease REALTORS Inc

  3120 Whispering Hills, Chester, NY 10918
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  /48

  $550,000

  • 4 Beds
  • 3.5 Baths
  • 2,064 Sq Ft

  22 The Dr, Westtown, NY 10998

  Imagine a stunning center hall colonial, with a walkout basement boasting four generous bedrooms, with the possibility of two more, complemented by 3.5 elegant baths. The breathtaking yard features an above-ground pool, a gorgeous two-tier brick patio, 2 sheds and more storage with an oversized two-car garage, perfect side door for a home office. Hardwood floors add warmth throughout, while

  Sheri Chablis Sohn Real Estate Corp

  22 The Dr, Westtown, NY 10998
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  /48

  $1,925,000

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

  395 Sarah Wells Trail, Goshen, NY 10924

  Welcome to Twin Oaks – A Masterfully Restored Hudson Valley Estate.Nestled along one of the most scenic and desirable roads in the Hudson Valley, Twin Oaks is a truly exceptional residence, offering a rare blend of historic grandeur and modern refinement. Set on a tranquil, park-like 8.2-acre estate at the edge of the charming Village of Goshen, this stately 5,450-square-foot Victorian

  Joseph Paoli Howard Hanna Rand Realty

  395 Sarah Wells Trail, Goshen, NY 10924
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  /29

  $340,000

  • 2 Beds
  • 2.5 Baths
  • 1,535 Sq Ft

  57 Winding Brook Dr, Walden, NY 12586

  This 2 bedroom 2.5 bath townhouse is being offered for the first time since the originalowner purchased it over 30 years ago.Enter the house through the front door or through the remote control garage door entry. No need to worry about bad weather.The kitchen has a glass tiled backsplash that brings a vivid splash of color to theroom. A small nook with two windows makes for cute

  Jaynie Aristeo Ridgeline Realty

  57 Winding Brook Dr, Walden, NY 12586
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  /28

  $499,000

  • 4 Beds
  • 2 Baths
  • 1,744 Sq Ft

  421 Nelson Rd, Monroe, NY 10950

  WELCOME TO 421 NELSON ROAD, YOUR PRIVATE RETREAT WITH ENDLESS POTENTIAL! SET ON 1.2 ACRES OF LEVEL LAND IN THE SOUGHT AFTER GREENWOOD LAKE/MONROE AREA, THIS SPACIOUS 4 BDRM, 2 BATH RANCH BLENDS CLASSIC CHARM WITH MODERN UPDATES. FROM THE MOMENT YOU ARRIVE, YOU'LL APPRECIATE THE TWO DRIVEWAYS AND A HEATED 2 CAR GARAGE W/WORKSHOP SPACE, PERFECT FOR HOBBYISTS, CAR ENTHUSIASTS, OR ANYONE WHO LOVES

  Paul Christman ARC Realty 1 in Sales

  421 Nelson Rd, Monroe, NY 10950
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  /38

  $275,000

  • 2 Beds
  • 1 Bath
  • 814 Sq Ft

  19 Lewis St, Otisville, NY 10963

  Welcome to 19 Lewis St! Discover the perfect blend of charm and comfort in this quaint 2-bedroom cottage, nestled in the heart of Otisville's Village. This home features 2 cozy bedrooms and 1 full bathroom, with sufficient closet space. The bright living room boasts exceptional natural lighting, making it ideal for relaxation and recreation. Additional amenities include ample attic space for

  Travis Thompson Keller Williams Hudson Valley

  19 Lewis St, Otisville, NY 10963

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