Orange County NY Homes for Sale with Private Pool

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  /32

  $550,000

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

  27 Rose Hill Park, Cornwall, NY 12518

  Pride of ownership is evident throughout this updated Cornwall home tucked away on a peaceful cul-de-sac. Sitting on over a half acre, the property offers the kind of outdoor space that is becoming increasingly difficult to find. The fenced in-ground pool serves as the centerpiece of the backyard, complemented by mature landscaping and a multi-level deck designed for gatherings, quiet evenings,

  Andrew Delgado RE/MAX Select

  27 Rose Hill Park, Cornwall, NY 12518
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  /48

  $729,000

  • 4 Beds
  • 3.5 Baths
  • 3,092 Sq Ft

  38 Pinehurst Cir, Monroe, NY 10950

  Welcome to an unparalleled lifestyle of luxury and leisure in Mansion Ridge, Orange County’s premier gated community. Nestled alongside a pristine Jack Nicklaus Signature Golf Course, this spectacular, completely renovated (2021) three-level townhouse offers the perfect blend of sophisticated design and resort-style amenities. Step inside to an airy, light-filled main level with hardwood floors

  Martha Randazzo Howard Hanna Rand Realty

  38 Pinehurst Cir, Monroe, NY 10950
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  /30

  $844,000

  $5K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 3,764 Sq Ft

  238 S Centerville Rd, Middletown, NY 10940

  Spacious Country Retreat on 22.6 Acres in Minisink Valley School District This exceptional property offers privacy, comfort, and extensive amenities set on 22.6 picturesque acres. The master bedroom and bathroom were updated in 2016, complemented by a wet bar in the family room—perfect for entertaining. The home features three fireplaces and a wood stove, creating warmth and character throughout.

  Linda VanDeWeert BHG Real Estate Green Team

  238 S Centerville Rd, Middletown, NY 10940
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  /50

  $1,145,000

  $50K PRICE DROP

  • 9 Beds
  • 6.5 Baths
  • 4,965 Sq Ft

  19 High St, Chester, NY 10918

  Own a true piece of history with the iconic Hambletonian House, a one-of-a-kind Victorian estate built in the 19th century by William Rysdyk, original owner of Hambletonian 10—the legendary sire that shaped nearly all modern Standardbred racehorses. Perfectly positioned on nearly three private acres atop a knoll in the heart of Chester, New York, this meticulously maintained property offers a

  Beth Palma Keller Williams Realty

  19 High St, Chester, NY 10918
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  /50

  $975,000

  $15K PRICE DROP

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

  10 Greenwich Ave, Central Valley, NY 10917

  A slice of Provence in the Hudson Valley. Locally revered as "The Castle on the Hill," Le Chateau des Verts offers a rare combination: the grand soul of a French estate with the easy, accessible flow of a ranch-style home. Sitting on over an acre of lush, mature grounds just 30 miles from Manhattan, it’s the ultimate escape for anyone looking to trade city noise for country quiet—without

  Micaela Stanaland Howard Hanna Rand Realty

  10 Greenwich Ave, Central Valley, NY 10917
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  /47

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 2,314 Sq Ft

  11 Country Hollow, Highland Mills, NY 10930

  Beautifully maintained and thoughtfully updated, this exceptional home is set on professionally landscaped grounds with outstanding curb appeal and a resort-style backyard designed for both relaxation and entertaining. The inviting interior features a grand entry foyer, a stunning chef's kitchen with custom cabinetry, granite countertops, and stainless steel appliances, along with spacious living

  Moche Halpern Blooming Realty

  11 Country Hollow, Highland Mills, NY 10930
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  /38

  $824,900

  $24K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,488 Sq Ft

  19 Aimee Ct, Warwick, NY 10990

  This home sits at the end of a quiet cul-de-sac of lush lawns and executive homes. The large porch welcomes you into the two story foyer. Huge dining room gives you room for all. The open kitchen/family room with fireplace and stone feature wall continues the airy feel. Well appointed kitchen has tall cabinets, wine refrigerator, Frigidaire professional appliances including 5 burner range. The

  Kimberly Corkum Keller Williams Realty

  19 Aimee Ct, Warwick, NY 10990
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  /37

  $764,900

  $24K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,145 Sq Ft

  89 W Ridge Rd, Warwick, NY 10990

  Nestled in a picturesque park-like country setting, this sprawling ranch offers the kind of timeless appeal with mature landscaping, established gardens, and a refreshing in-ground pool. The property's solid construction and “good bones” provides the perfect canvas for your personal updates and design vision. Enjoy the benefits of a setting that would take years to recreate with new construction,

  Kimberly Starks Howard Hanna Rand Realty

  89 W Ridge Rd, Warwick, NY 10990
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  /45

  $11,000,000

  $3M PRICE DROP

  • 16 Beds
  • 16 Baths
  • 15,252 Sq Ft

  14 Castleton Dr, Highland Mills, NY 10930

  R1A zoned, R3A zoned, agriculture zone approved, infinity pool, tennis and basketball court, gazebo and private lake set across gated 39.1 acresMAIN HOUSE - 10 bedrooms, 6 full baths, 3 half baths, 10 fireplaces, Kitchen has Miele Steam unit, Viking warming drawer, Viking microwave, 3 Viking ovens, including 6-burner and grill, 2 dishwashers, walk-in refrigerator, custom-designed and

  Laura Denberg Corcoran Baer & McIntosh

  14 Castleton Dr, Highland Mills, NY 10930
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  /20

  $429,900

  • 3 Beds
  • 1.5 Baths
  • 1,276 Sq Ft

  342 Coldenham Rd, Walden, NY 12586

  Just Listed 3 bedroom one and a half bath with a 2-car spacious garage with a storage area above the garagethat is nestled on a 1.2 acre of a well-manicured lawn. The property is located close to train station as well the New York State Thruway. It's a ready to move in home on one level just add your personal touch to make it a complete home. This home would make a great home for your family

  Lou Shorette Century 21 E & M Williams Rlty

  342 Coldenham Rd, Walden, NY 12586
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  /31

  $799,900

  • 5 Beds
  • 3.5 Baths

  161 West St, Warwick, NY 10990

  Beautifully maintained Colonial by its original owners, in the highly desirable Village of Warwick, set on 1.42 acres with municipal water, sewer, and natural gas. This move-in-ready home features 5 bedrooms and 3.5 baths, including a first-floor bedroom and full bath ideal for guests or a home office. Updated eat-in kitchen with granite countertops, quartz breakfast bar, and new dishwasher opens

  Lisa Holmes Keller Williams Village Square Realty

  

  161 West St, Warwick, NY 10990
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  /25

  $1,499,999

  • 3 Beds
  • 2 Baths
  • 3,450 Sq Ft

  283 Prospect Rd, Monroe, NY 10950

  An extraordinary property offering the perfect balance of privacy, comfort, and natural beauty. While the photos showcase its appeal, the true scale and atmosphere can only be experienced in person. Don't miss the opportunity to tour this exceptional home and see firsthand what makes it so special.

  Lazar Schvimmer Mount Realty

  283 Prospect Rd, Monroe, NY 10950
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  /50

  $975,000

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

  309 Beattie Rd, Washingtonville, NY 10992

  Welcome to your own private retreat. Set on beautifully landscaped grounds, this impressive custom Colonial offers 6 bedrooms, 4 full baths, plus a dedicated office that can easily function as a 7th bedroom. A winding driveway leads to the stately residence, where mature trees, manicured lawns, and colorful gardens create an exceptional first impression.Inside, you'll find over three levels

  Janet Rendle Weichert Realtors

  309 Beattie Rd, Washingtonville, NY 10992
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  /14

  $294,925

  $45K PRICE INCREASE

  • 3 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  12 Redwood Dr, Highland Mills, NY 10930

  Roomy 3 Bedroom townhome in Timber Ridge, offering an open layout on the first floor. Living Room has sliding glass doors to a private deck facing the woods. Second floor offers 3 good size bedrooms and a full hallway bath. The lower level has mechanicals, laundry room with potential for additional living space, over 600 square feet.This is a short sale, third party approval needed. Realtor

  Patricia Cannizzaro Century 21 Alliance Rlty Group

  12 Redwood Dr, Highland Mills, NY 10930
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  /36

  $800,000

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

  985 Craigville Rd, Chester, NY 10918

  Welcome to your own private retreat, where timeless design, exceptional outdoor living, and over three acres of peaceful surroundings come together to create an unforgettable place to call home.Inside, the heart of the home is anchored by a stunning double sided fireplace that effortlessly connects the main living areas, creating warmth, character, and an inviting atmosphere for both everyday

  DAVID DEBERARDINIS Serhant LLC

  985 Craigville Rd, Chester, NY 10918
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  /50

  $749,999

  $50K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,718 Sq Ft

  58 Nancy Ln, Chester, NY 10918

  Imagine ending everyday watching the sun set from your front porch, experiencing views that change with every season. Sunset views, fenced yard, brand new Trex deck, pool, home office and room for four sleeping spaces make this the perfect property. Perched at the top of the highly sought-after Fieldcrest subdivision, this stunning Colonial captures breathtaking panoramic views and unforgettable

  Gina Dudgeon Howard Hanna Rand Realty

  58 Nancy Ln, Chester, NY 10918
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  /32

  $599,000

  • 2 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  739 Hewitt Ln, New Windsor, NY 12553

  Experience refined riverfront living in this stunning two-bedroom, two-and-a-half-bath condominium with sweeping, unobstructed views of the Hudson River. Designed with both elegance and functionality in mind, this exceptional residence blends high-end finishes with thoughtful craftsmanship throughout.The open-concept main living space is anchored by a stone-clad facade wall with built in

  Eve Carnevalla Muhlfeld Tactical Realty LLC

  739 Hewitt Ln, New Windsor, NY 12553
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  /24

  $499,900

  • 4 Beds
  • 2 Baths
  • 2,005 Sq Ft

  13 Lakeview Dr, Warwick, NY 10990

  Spacious high Ranch with endless possibilities set on 1 level acre in a highly desirable Warwick.This 4 Bedroom 2,005 square foot home offers a generous living space and a layout designed for comfort and flexibility.On the main level you will find the Master bedroom with walk-in closet, 2nd bedroom, and full bathroom. The kitchen features a small island, eat-in area, new stainless steel

  Nicole Manfredo Cole Prime Realty

  13 Lakeview Dr, Warwick, NY 10990
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  /50

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 3,008 Sq Ft

  14 Wagner Dr, Rock Tavern, NY 12575

  VACATION EVERY DAY, WITHOUT EVER LEAVING HOME! Welcome to 14 Wagner Drive, Rock Tavern More than a home, this is a private retreat where exceptional outdoor living, timeless craftsmanship, and everyday tranquility come together. Nestled within a peaceful, established neighborhood, 14 Wagner Drive is the property you have been waiting for. Meandering pathways, mature trees, award winning

  Frank Muccari Cronin & Company Real Estate

  14 Wagner Dr, Rock Tavern, NY 12575
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  /27

  $185,000

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  326 Concord Ln, Middletown, NY 10940

  PRICED TO SELL!!! Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase. Add your final touches and make it yours! A ground level end unit with open floor plan from living room to dining room with sliders that lead to a seating area where you can enjoy the outdoors. Beautiful kitchen with stainless steel appliances & plenty of cabinet space. Spacious bedrooms, one

  Sandra Arnez KW Hudson Valley United

  326 Concord Ln, Middletown, NY 10940
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  /50

  $899,000

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,894 Sq Ft

  114 Last Rd, Middletown, NY 10941

  Distinctive 11-Acre Country Retreat - More than a home, this property delivers a lifestyle defined by space, privacy, and ease. Set across two parcels totaling 11.1 acres, this distinctive Cape Cod combines thoughtful design and easy, everyday living. From the expansive covered front porch to the farmhouse-style entry, the home immediately feels airy and inviting. Inside, the home balances warmth

  Michelle Genatempo Howard Hanna Rand Realty

  114 Last Rd, Middletown, NY 10941
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  /46

  $299,000

  $41K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,320 Sq Ft

  607 Mountain Laurel Dr, Monroe, NY 10950

  Monroe-Woodbury Schools Townhouse with Low Taxes — Zoned for highly sought-after Pine Tree & Sapphire Elementary Schools. Step into this inviting 3-bedroom, 2.5-bath townhouse in the desirable Windridge community where space, light, and thoughtful updates come together. The spacious living room showcases younger laminate flooring that looks beautiful and cleans like a dream, while front-facing

  Rosalie Cook Weichert Realtors

  607 Mountain Laurel Dr, Monroe, NY 10950
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  /24

  $729,000

  Pre-Foreclosure

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

  27 Grosso Ct, Montgomery, NY 12549

  Private 6.5-acre Victorian retreat with heated salt water pool! Tucked away on a quiet cul-de-sac, this impressive home features a dramatic two-story foyer, soaring ceilings, creates a grand first impression and leads to spacious living areas throughout the home and a flexible floor plan with exceptional potential on each floor including the walk out basement. Enjoy scenic views, generous indoor

  Camelia Pena-Rivera RE/MAX Distinguished Hms.&Prop

  27 Grosso Ct, Montgomery, NY 12549
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  /50

  $4,499,000

  $1K PRICE DROP

  • 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
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  /42

  $749,000

  • 3 Beds
  • 3 Baths
  • 2,826 Sq Ft

  99 Whitlock Rd, Otisville, NY 10963

  Imagine waking up to sweeping views, stepping onto your expansive deck with a morning coffee, and spending warm summer afternoons by your private pool surrounded by nearly 16 acres of open countryside. 99 Whitlock Road offers the space and freedom that many dream about but rarely find. Combining classic Cape Cod and Colonial charm with contemporary design elements, this inviting home delivers a

  Arya Rabinovits eRealty Advisors, Inc

  99 Whitlock Rd, Otisville, NY 10963
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  /21

  $420,000

  • 4 Beds
  • 2.5 Baths
  • 1,644 Sq Ft

  114 Prospect Ave, Maybrook, NY 12543

  Welcome to this spacious 3-bedroom, 2-bath home in the heart of the Village of Maybrook. Offering a versatile layout with two bonus rooms, this home provides plenty of space for a home office, playroom, gym, or guest area to fit your lifestyle. Enjoy year-round relaxation in the bright sunroom overlooking the large backyard, perfect for entertaining. Summer fun awaits with the above-ground pool

  Lisa Wade-Sebring Hudson Valley Home Connection

  114 Prospect Ave, Maybrook, NY 12543
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  /50

  $2,895,000

  $100K PRICE DROP

  • 6 Beds
  • 9 Baths
  • 6,415 Sq Ft

  198 Corbett Rd, Montgomery, NY 12549

  A Private Hudson Valley Estate 48.5 Acres of Luxury and Recreation Set across 48.5 breathtaking acres in Montgomery, New York, this extraordinary 6,415-square-foot estate offers a rare opportunity to own a private retreat where luxury, nature, and recreation exist in perfect harmony. Thoughtfully designed for both grand entertaining and comfortable living, the residence features six spacious

  Nissim Levy Keller Williams Realty Liberty

  198 Corbett Rd, Montgomery, NY 12549
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  /50

  $1,750,000

  $525K PRICE DROP

  • 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, The Rest is a rare and remarkable offering—a Gothic Revival masterpiece and enduring symbol of 19th-century architecture, masterfully adapted for modern living.The Rest was designed as both a living work of art and an inviting home and celebrates the ethos of High Victorian Gothic Revival showcasing soaring tracery ceilings,

  Zebee Amy Voss Julia B Fee Sothebys Int. Rlty

  560 Grand Ave, Newburgh, NY 12550
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  /47

  $665,000

  • 3 Beds
  • 2 Baths
  • 1,984 Sq Ft

  233 Hill Rd, Goshen, NY 10924

  Welcome to your private country retreat on 2 beautifully level acres in the heart of Goshen. Offering the perfect balance of peaceful privacy and everyday convenience, this spacious home is designed for comfortable living and effortless entertaining.The heart of the home is a stunning open-concept chef's kitchen featuring rich cherry wood cabinetry, granite countertops, a butcher block

  Kevin Grier KW Hudson Valley United

  233 Hill Rd, Goshen, NY 10924
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  /34

  $899,000

  $100K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 2,620 Sq Ft

  4 Lambros Dr, Monroe, NY 10950

  Stop searching, because you have just found your dream home. Situated on over an acre of land, this gorgeous home has over 2600 sqft. of space to call your own. Living area, kitchen with granite countertops, and finished basement. With less than 15 minutes drive to Woodbury Commons shopping center, this is a gem of a house. Whether it's for you or your family, this is a place you can make your

  Avrahom Lewinson Keller Williams Realty

  4 Lambros Dr, Monroe, NY 10950
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  /46

  $845,000

  • 4 Beds
  • 2.5 Baths
  • 2,392 Sq Ft

  77 Houston Rd, Goshen, NY 10924

  Nestled amid the rolling landscapes of Goshen, New York, 77 Houston Road offers a graceful blend of modern elegance and serene country living. This beautifully appointed colonial home sits proudly on a pristine 4.3 acre lot of manicured lawn. Its classic front porch welcoming you with timeless charm and tranquil views. Step inside to discover an open-concept living space featuring a spacious

  Rafael Luciano Luciano Rios Property Grp, Inc

  77 Houston Rd, Goshen, NY 10924
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  /34

  $349,999

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  3414 Whispering Hills, Chester, NY 10918

  Welcome home to this beautifully updated 3-bedroom, 2-bathroom condominium with a 1-car garage, perfectly situated in the highly sought-after Whispering Hills community. Offering modern upgrades, spacious living, and resort-style amenities, this home is truly move-in ready. Step inside to discover a bright, open floor plan featuring gleaming hardwood floors, an updated chef-inspired kitchen with

  Kevin Grier KW Hudson Valley United

  3414 Whispering Hills, Chester, NY 10918
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  /22

  $562,000

  $13K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,968 Sq Ft

  2 Sycamore Ln, Goshen, NY 10924

  Charming Split-Level fenced in property located in the highly sought-after Chester School District in Goshen, New York. Don't miss the opportunity to preview this beautiful home featuring an open and inviting floor plan designed for comfortable everyday living and entertaining. Step outside to a spacious rear yard complete with an above-ground pool and gazebo, creating the perfect setting for

  Jeanette Santory Howard Hanna Rand Realty

  2 Sycamore Ln, Goshen, NY 10924
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  /50

  $925,000

  Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,308 Sq Ft

  10 Sutherland Dr, Highland Mills, NY 10930

  Luxury, comfort, and exceptional craftsmanship define this stunning four-bedroom Center Hall Colonial. Thoughtfully designed with superior craftsmanship and premium finishes throughout, this impressive residence offers the perfect blend of sophistication, comfort, and functionality for the discerning buyer. At the heart of the home is a spectacular custom chef's kitchen featuring Travertine

  Richard Froehlich RE/MAX Benchmark Realty Group

  10 Sutherland Dr, Highland Mills, NY 10930
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  /49

  $2,595,000

  $155K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,059 Sq Ft

  26 Roberson Ave, Pine Bush, NY 12566

  Welcome to the Daniel Bull House, a remarkable 1787 estate and one of the Hudson Valley’s finest examples of early American stone architecture. Originally built by one of Hudson Valley’s founding families, this historic stone residence has been masterfully restored, blending old world craftsmanship with modern luxury. Ideally located just minutes from town yet offering the serenity of a private

  Shaina Marron Houlihan Lawrence, Inc

  26 Roberson Ave, Pine Bush, NY 12566
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  /33

  $850,000

  Pre-Foreclosure

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

  1010 Pine View, New Windsor, NY 12553

  Tucked away on a private street within the desirable Forest Glen community, this tastefully updated 5-bedroom, 4-bath modern Colonial offers the perfect balance of privacy, space, and convenience—just 6 minutes to the Salisbury/Cornwall Metro-North station and moments from major shopping and everyday amenities. Set on a beautifully level and fenced 0.51-acre property, the home features an

  Samuel Berek Serhant LLC

  1010 Pine View, New Windsor, NY 12553
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  /50

  $5,500,000

  $1K PRICE INCREASE

  • 3 Beds
  • 3.5 Baths
  • 2,929 Sq Ft

  165 Hasbrouck Rd, Goshen, NY 10924

  This 88-acre Hudson Valley equestrian estate, privately nestled down a long drive in an area of fine homes, offers a magnificent retreat featuring two unique residences and premier horse facilities. Meticulously crafted to balance luxury with functionality, the property was designed to provide ultimate comfort for both horse and human. The estate’s rustic stone and wood main house, set amidst

  Michelle Genatempo Howard Hanna Rand Realty

  165 Hasbrouck Rd, Goshen, NY 10924
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  /38

  $989,900

  • 4 Beds
  • 3.5 Baths
  • 5,440 Sq Ft

  32 Pearce Dr, Highland Mills, NY 10930

  Stunning Luxury Home with Resort-Style Amenities:Welcome to this exceptional 5,440 sq ft residence offering the perfect blend of elegance, comfort, and modern upgrades. This spacious home features 4 generously sized bedrooms, including a luxurious primary suite with a private balcony, beautiful views, and a spacious walk-in closet.The primary bathroom is a true retreat, showcasing a spa-like

  Jean DiMatteo DiMatteo Realty LLC

  32 Pearce Dr, Highland Mills, NY 10930
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  /30

  $379,000

  • 3 Beds
  • 1.5 Baths
  • 884 Sq Ft

  42 Old Route 208, Montgomery, NY 12549

  Come see this well maintained and charming 3 bedroom, 1.5 bath ranch that's truly move in ready! This inviting home has been updated with a newer roof, siding, windows, flooring, and features a beautiful above ground pool that's perfect for relaxing on hot summer days. The spacious basement offers plenty of room for a recreation area, home gym, workshop, or additional living space. Step outside

  Larry Curasi Curasi Realty, Inc.

  42 Old Route 208, Montgomery, NY 12549
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  /45

  $698,000

  • 4 Beds
  • 2 Baths
  • 4,020 Sq Ft

  23 Peach Terrace, Newburgh, NY 12550

  Step inside and feel the sense of space and possibility in this extraordinary 4,000+ sq. ft. contemporary designed for gathering, celebrating, and creating lasting memories. From the moment you enter through the dramatic double doors, you’re welcomed by a sweeping foyer that sets the tone for the grand scale and thoughtful design found throughout. At the heart of the home is a stunning oversized

  Susan Todd BHHS Hudson Valley Properties

  23 Peach Terrace, Newburgh, NY 12550

Showing Results 81 - 120, Page 3 of 6