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Homes for Sale in Orange County NY with 5-Bedrooms & a Private Pool

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  • /48

    $1,780,000

    • 6 Beds
    • 4.5 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 French Second Empire Late

    Agent Photo

    Joseph Paoli

    Howard Hanna Rand Realty

    (845) 400-8382

    395 Sarah Wells Trail, Goshen, NY 10924
  • /47

    $964,999

    • 5 Beds
    • 4 Baths
    • 3,154 Sq Ft

    43 Greenwich Ave, Central Valley, NY 10917

    Welcome to 43 Greenwich Avenue, a beautifully appointed 5-bedroom, 4-bath Colonial nestled in the highly sought-after Greens community of Central Valley. Offering over 3,100 square feet of living space, this home features a spacious and sun-filled layout, perfect for both everyday living and entertaining. The inviting family room showcases soaring ceilings, skylights, and a cozy fireplace, while

    Agent Photo

    Alexandra Zinko

    Century 21 Realty Center

    (845) 205-7672

    43 Greenwich Ave, Central Valley, NY 10917
  • /32

    $1,799,000

    • 5 Beds
    • 9 Baths
    • 7,794 Sq Ft

    3 Bristol Dr, Middletown, NY 10941

    Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 square feet of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday

    Agent Photo

    Mohamed Elgoarany

    All American Realty Management

    (329) 215-0309

    3 Bristol Dr, Middletown, NY 10941
  • /36

    $949,900

    • 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
  • /58

    $575,000

    • 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
  • /47

    $765,000

    • 5 Beds
    • 5 Baths
    • 4,518 Sq Ft

    1 Far Horizons Dr, Newburgh, NY 12550

    Set on nearly 2 acres in the Marlboro School District, this expansive 4,518-square-foot Hudson Valley farmhouse offers space, style, and versatility at every turn. With 5 oversized bedrooms and 5 full bathrooms, it’s perfect for multi-generational living, extended guests, or work-from-home lifestyles. The dramatic two-story living room is a showstopper, featuring a floor-to-ceiling stone

    Wendy Beck Krumpfer Realty Group, LLC

    1 Far Horizons Dr, Newburgh, NY 12550
  • /35

    $599,900

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

    669 Mountain Rd, Middletown, NY 10940

    Country Escape of 6 spacious bedrooms offers space, privacy, and a serene setting on 3.38 acres. Just about 75 miles from New York City, it’s close enough for convenient weekend escapes yet far enough to feel like a true retreat feels like a private estate—perfect for those seeking a refined escape from city life A grand foyer opens to a bright, airy layout with high ceilings, large windows, and

    Michelle Gruberger Real Estate Circuit Inc

    669 Mountain Rd, Middletown, NY 10940
  • /48

    $925,000

    • 5 Beds
    • 3.5 Baths
    • 3,680 Sq Ft

    21 Bull Mine Rd, Chester, NY 10918

    Welcome to this distinguished colonial residence offering five bedrooms and three and a half baths, gracefully positioned on 2.3 acres of private, scenic grounds. Set back from the road, the home is surrounded by expansive green lawns, providing an unparalleled sense of privacy and sophistication. The inviting front porch presents an ideal space to enjoy your morning coffee while taking in the

    Donna Gennaro Howard Hanna Rand Realty

    21 Bull Mine Rd, Chester, NY 10918
  • /50

    $1,395,000

    • 5 Beds
    • 4.5 Baths
    • 5,802 Sq Ft

    18 Almond Tree Ln, Warwick, NY 10990

    WOW . . . STUNNING 5,802 square foot colonial/country hilltop estate with gorgeous360 degree mountain views, full/finished walkout basement, 3-car attached garage, plus a 2-car detached garage/carriage house with partially finished loft space, AND a backyard oasis complete with in-ground pool and hot tub . . . Located in the fabulous Waterbury Estates neighborhood -- offering privacy, yet

    Dean Diltz Keller Williams Realty

    18 Almond Tree Ln, Warwick, NY 10990
  • /50

    $2,995,000

    • 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
  • /47

    $1,750,000

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    106 Post Rd, Slate Hill, NY 10973

    A Private Mini-Estate of Architectural Distinction in the Goshen School District. Set within the quiet preserve of over 17 acres of wooded grounds, this fully renovated architectural geodesic dome residence—known locally as The Wooden Igloo—offers a rare opportunity to own a true mini-estate that blends iconic design, modern luxury, and exceptional flexibility. Thoughtfully reimagined from top to

    Joseph Frullaney Real Broker NY LLC

    106 Post Rd, Slate Hill, NY 10973
  • /48

    $869,000

    • 5 Beds
    • 2 Baths
    • 1,900 Sq Ft

    11 Merriewold Ln N, Monroe, NY 10950

    Discover this beautiful colonial in the sought-after Merriewold section of the Village of South Blooming Grove. With 5 bedrooms and 2 bathrooms, this home offers plenty of space for a growing family. The spacious interior features a kitchen breakfast bar, a formal dining room, and an inviting living area. The level, private lot offers plenty of room for outdoor activities. The backyard is

    Shalom Landau eRealty Advisors, Inc

    11 Merriewold Ln N, Monroe, NY 10950
  • /50

    $5,950,000

    • 6 Beds
    • 9 Baths
    • 9,051 Sq Ft

    43 Ontio Rd, Tuxedo Park, NY 10987

    The Kingsbury-Curtis House | Tuxedo Park, NY. An extraordinary historic estate in the private, gated community of Tuxedo Park, commanding elevated vistas over both Wee Wah Lake and Tuxedo Lake, with the Ramapo Mountains and a partial New York City skyline forming a dramatic backdrop. Nestled on a prominent summit, this distinguished residence c.1886 is crafted in fieldstone, brick, and limestone

    Elizabeth Broderick Tuxedo Hudson Realty Corp

    43 Ontio Rd, Tuxedo Park, NY 10987
  • /50

    $1,395,000

    • 6 Beds
    • 7 Baths
    • 8,180 Sq Ft

    5 Trinity Place, Cornwall, NY 12518

    Set at the end of a private road and backing directly to the Storm King Golf Club, this mansion-style residence offers rare privacy, scale, and presence on 1.6 acres in Cornwall. The home spans approximately 8,180 square feet and showcases timeless architecture with classic, old-world character. Grand formal spaces balance nicely with more relaxed living areas, all highlighted by four fireplaces

    STEVEN WROBEL JR. Serhant LLC

    5 Trinity Place, Cornwall, NY 12518
  • /34

    $999,000

    • 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
  • /31

    $649,999

    • 5 Beds
    • 6 Baths
    • 3,568 Sq Ft

    7 Cherrywood Dr, Goshen, NY 10924

    This beautiful, spacious contemporary split-level home is perfect for the in-laws, featuring a separate apartment. The main house boasts 5 bedrooms and 4 bathrooms, with an entrance foyer leading to a large entertaining room with Fireplace. From there, you can move into the media room and then onto separate entrance to pool areaOn the main level, features hardwood floors threw out home. Large

    Joseph Brown RE/MAX Real Property Group

    7 Cherrywood Dr, Goshen, NY 10924
  • /50

    $1,450,000

    • 5 Beds
    • 3.5 Baths
    • 3,472 Sq Ft

    106 Post Rd, Slate Hill, NY 10973

    A Private Mini-Estate of Architectural Distinction in the Goshen School District. Set within the quiet preserve of over 10 acres of wooded grounds, this fully renovated architectural geodesic dome residence—known locally as The Wooden Igloo—offers a rare opportunity to own a true mini-estate that blends iconic design, modern luxury, and exceptional flexibility. Thoughtfully reimagined from top to

    Joseph Frullaney Real Broker NY LLC

    106 Post Rd, Slate Hill, NY 10973
  • /34

    $999,000

    • 5 Beds
    • 4 Baths
    • 3,136 Sq Ft

    12 Damian Ct, Chester, NY 10918

    Welcome to 12 Damian Court, a spacious Colonial set on a quiet cul-de-sac. This well-maintained home offers 5 bedrooms and 4 bathrooms, with four bedrooms on the upper level and one additional bedroom in the finished basement. The main level features generous living and dining areas, perfect for everyday living and entertaining. The finished basement adds excellent flexibility with a second

    Elimelech Kremer MS Realty Group USA, Inc

    12 Damian Ct, Chester, NY 10918
  • /44

    $895,000 Open Sat 1PM - 3PM

    • 6 Beds
    • 7 Baths
    • 4,890 Sq Ft

    10 Willys Ct, Rock Tavern, NY 12575

    PRICE IMPROVEMENT | Two Homes in One on 2.2 Acres | Nearly 5,000 SF | 90 Minutes to Manhattan. Some homes offer space. This one offers true multigenerational living with privacy, flexibility, and estate-scale comfort. Privately set at the end of a quiet cul-de-sac in Rock Tavern, this exceptional dual-residence colonial spans 2.2 private acres and offers nearly 5,000 square feet of luxury living

    Sal Rajput Coldwell Banker Realty

    10 Willys Ct, Rock Tavern, NY 12575
  • /28

    $849,000

    • 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
  • /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
  • /37

    $425,000

    • 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
  • /20

    $665,000

    • 5 Beds
    • 3 Baths
    • 2,573 Sq Ft

    94 Mearns Ave, Highland Falls, NY 10928

    5 Bedroom 3 Bathroom12 Rooms including basement.2,573 sq ft home within a 0.537 acres is an entertainers dream!! Central Air/2 zonesNatural GasMunicipal Water and SewerStand up full accessible attic4 2nd floor large bedroomsensuite walk-in closet/large full bath2nd floor laundry1st floor bedroom with French DoorsLarge Yard with spectacular

    Jennifer Gargiulo Corcoran Baer & McIntosh

    94 Mearns Ave, Highland Falls, NY 10928
  • /4

    $850,000

    • 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
  • /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
  • /40

    $799,900

    • 5 Beds
    • 5 Baths
    • 4,089 Sq Ft

    20 Bernadette Way, Washingtonville, NY 10992

    Welcome to a one of a kind opportunity in the heart of Washingtonville. This expansive raised ranch with a stunning two story contemporary addition offers the perfect blend of space, style, and flexibility. With five bedrooms and four full baths this property is ideal for multi generational living or as an income producing multi unit setup. The home showcases gourmet kitchens with granite

    Anesha Nesbitt eXp Realty

    20 Bernadette Way, Washingtonville, NY 10992
  • /50

    $875,000

    • 5 Beds
    • 4 Baths
    • 3,103 Sq Ft

    4 Makan Rd, Monroe, NY 10950

    Ridgetop Estates, Monroe NY, Features 5 Bedrooms • 4 Full Bathrooms • Mountain Views and Room for Expansion. Set on a gently elevated homesite gives way for sweeping views of the neighboring countryside. Your new sun-filled home delivers the space, flexibility, and comfort today’s buyers want. The main level blends comfortable gathering spaces with an easy flow: a gracious living room, a formal

    Chris Carbone HomeSmart Homes & Estates

    4 Makan Rd, Monroe, NY 10950
  • /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
  • /50

    $1,750,000

    • 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
  • /50

    $29,500,000

    • 19 Beds
    • 22 Baths
    • 22,400 Sq Ft

    120 Ridge Rd, Tuxedo Park, NY 10987

    Renamor is a spectacular estate blending history, grandeur and modern sustainability in a truly unique way. It is situated on the largest piece of property ever to be sold in historic Tuxedo Park, 151 acres! The fact that it’s now on the market for the first time in over 30 years makes it even more enticing for a discerning buyer seeking a one-of-a-kind property. Built circa 1928 in the romantic

    Richard Ellis Ellis Sotheby's Intl Realty

    120 Ridge Rd, Tuxedo Park, NY 10987
  • /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
  • /50

    $1,980,000

    • 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, 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
  • /48

    $620,000

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

    33 Winchester Dr, Monroe, NY 10950

    HUGE PRICE REDUCTION- 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

    Dennis Clark Howard Hanna Rand Realty

    33 Winchester Dr, Monroe, NY 10950
  • /36

    $1,300,000

    • 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
  • /50

    $4,499,000

    • 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
  • /43

    $765,000 Pre-Foreclosure

    • 5 Beds
    • 3 Baths
    • 2,923 Sq Ft

    18 Coach House Ct, New Windsor, NY 12553

    Welcome to this stunning 4-bedroom, 3-full-bath Colonial tucked away on a quiet cul-de-sac, where resort-style outdoor living takes center stage. This home offers the perfect blend of classic charm, modern comfort, and an entertainer’s dream backyard.Step outside to a spectacular private oasis featuring an in-ground pool with swim-up bar, waterfall, and waterslide, surrounded by mature,

    Christopher Kimiecik Keller Williams Realty

    18 Coach House Ct, New Windsor, NY 12553
  • /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
  • /2

    $525,000 Coming Soon

    • 5 Beds
    • 2 Baths
    • 1,965 Sq Ft

    171 Wawayanda Ave, Middletown, NY 10940

    Spacious and versatile split-level home offering 5 bedrooms and 2 full bathrooms with a home office, perfect for extended living or flexible space needs. This well-maintained property features a bright and inviting layout with two large family rooms, generously sized bedrooms, and an updated kitchen with Silestone countertops, wooden cabinets, and energy-efficient stainless steel appliances.

    Tiasha Coakley Keller Williams Hudson Valley

    171 Wawayanda Ave, Middletown, NY 10940
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