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Middletown, NY Homes for Sale with Pool

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  • /32

    $1,700,000

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

    3 Bristol Dr, Middletown, NY 10941

    PRICE REDUCTION FOR FASTER SALE...OWNER RELOCATING.....HURRY UP....WILL NOT LAST.............................Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft 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

    Agent Photo

    Mohamed Elgoarany

    All American Realty Management

    (329) 215-0309

    3 Bristol Dr, Middletown, NY 10941
  • /48

    $483,900

    • 3 Beds
    • 3.5 Baths
    • 2,521 Sq Ft

    53 Cornwall Ln, Middletown, NY 10940

    Beautifully renovated 3-bedroom, 3.5-bathroom townhouse with a 2-car garage, located in the highly desirable Woodside Knolls community. This spacious home offers modern updates throughout, providing comfort, style, and functionality for today’s living. Conveniently situated just minutes from the Garnet Health Medical Center, Galleria Mall, Metro-North, shops, supermarkets, and major highways,

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 217-0628

    53 Cornwall Ln, Middletown, NY 10940
  • /50

    $620,000

    • 3 Beds
    • 2 Baths
    • 3,080 Sq Ft

    179 Reservoir Rd, Middletown, NY 10940

    Warmth, comfort & space in the Hudson Valley. Welcome home to this spacious Colonial on 2.8 acres offering 3–4 bedrooms, 2 full baths, and a detached 2-car garage with oversized loft. The heart of the home is the large family room — cathedral ceilings, a stunning stone fireplace, and beautiful hardwood floors — the perfect place to gather. The private second-floor primary suite has its own full

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 207-0914

    179 Reservoir Rd, Middletown, NY 10940
  • /46

    $489,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 2,427 Sq Ft

    59 Woodside Knolls Dr, Middletown, NY 10940

    Welcome home to this impeccably maintained, tri-level townhouse nestled in the heart of the scenic Hudson Valley. Boasting over 2,400 sq. ft. of modern living space, this home features 9' ceilings, gleaming hardwood floors, and an open layout. The kitchen shines with countertops, stainless steel appliances, and a charming breakfast area. Retreat to the spacious primary suite with a walk-in closet

    Agent Photo

    Donna Reese

    Keller Williams Hudson Valley

    (329) 209-9797

    59 Woodside Knolls Dr, Middletown, NY 10940
  • /33

    $499,000

    • 3 Beds
    • 2.5 Baths
    • 2,211 Sq Ft

    60 Magnolia Park Rd, Middletown, NY 10940

    Beautifully cared-for 3 bedroom, 2.5-bath townhouse in the heart of Middletown! Spanning three levels, this home offers comfortable, versatile living with hardwood floors throughout both the main and second levels. The bright main floor features an open-concept living area featuring a fireplace, a dining area, along with a modern kitchen complete with granite countertops and ample cabinet space.

    Sandra Laramore Redfin Real Estate

    60 Magnolia Park Rd, Middletown, NY 10940
  • /34

    $640,000 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    235 Maples Rd, Middletown, NY 10940

    This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

    Shernette Hall VYLLA Home

    235 Maples Rd, Middletown, NY 10940
  • /36

    $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
  • /43

    $594,900

    • 3 Beds
    • 2.5 Baths
    • 2,008 Sq Ft

    180 Ridge Dr, Middletown, NY 10940

    180 Ridge Drive is a beautifully maintained 3 bedroom, 2 1/2 bath pool house located in the Town of Mt. Hope. This outstanding property is situated on a quiet country road in the Minisink School District and just a short drive to shopping, fine restaurants and public transportation. This home has everything one could wish for in their forever home; Bamboo hardwood floors, tile in the kitchen and

    Tom Pahucki Keller Williams Realty

    180 Ridge Dr, Middletown, NY 10940
  • /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
  • /44

    $605,000

    • 4 Beds
    • 3 Baths
    • 2,132 Sq Ft

    125 White Bridge Rd, Middletown, NY 10940

    This home offers so much more than a new build. Enjoy 2,132 square feet of well maintained, comfortable living space, topped with a brand new roof. Set on 2.6 beautiful acres in a serene country setting, the property’s signature feature is its fully owned solar array. No roof penetrations, no lease agreements — just clean energy and real savings. Electric bills as low as $28 per month speak for

    Anthony Spadaro RE/MAX Benchmark Realty Group

    125 White Bridge Rd, Middletown, NY 10940
  • /21

    $560,000

    • 4 Beds
    • 3 Baths
    • 2,162 Sq Ft

    77 Upper Rd, Middletown, NY 10940

    This beautiful ranch-style property is ready to move in. Amazing upgrades were made to this home with beautiful hardwood floors, 4 bedrooms, 3 bathrooms, a huge finished basement with 3 additional rooms for storage or home office, and it also has space for a personal gym with access to an amazing backyard that features a beautiful above-ground pool, a tennis court, volleyball court, or basketball

    Yajaira Silva Madison Allied LLC

    77 Upper Rd, Middletown, NY 10940
  • /21

    $485,000

    • 2 Beds
    • 2.5 Baths
    • 2,084 Sq Ft

    1 High Ridge Ln, Middletown, NY 10940

    Welcome to refined, low maintenance living in one of Middletown’s most sought after gated communities. This beautifully maintained end unit townhouse offers the perfect balance of space, comfort, and convenience, with over 2,000 square feet of living space designed for today’s lifestyle. Step inside to find a bright and inviting layout featuring two spacious bedrooms, each with generous closet

    Jason Madison eXp Realty

    1 High Ridge Ln, Middletown, NY 10940
  • /46

    $489,999

    • 2 Beds
    • 2 Baths
    • 1,612 Sq Ft

    10 Cyprus Dr, Middletown, NY 10940

    Welcome to 10 Cyprus at Wildflowers at Wallkill, where comfort, style, and easy living come together in one beautiful home. This meticulously maintained 2-bedroom, 2 full bath residence offers the convenience of single-level living with a bright, open-concept layout designed for both everyday living and effortless entertaining. Sunlight pours through oversized windows, filling the space with

    Hilary Ryan Goldman Howard Hanna Rand Realty

    10 Cyprus Dr, Middletown, NY 10940
  • /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
  • /27

    $199,000

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft

    326 Concord Ln, Middletown, NY 10940

    Buttonwood Hills Condominiums now offers a 2 bedroom/2 bath unit for your purchase & to call home! A ground level end unit with open floor 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 with a Suite with double closets and a private full

    Sandra Arnez Keller Williams Hudson Valley

    326 Concord Ln, Middletown, NY 10940
  • /35

    $499,900

    • 2 Beds
    • 2 Baths
    • 1,868 Sq Ft

    19 Sunflower St, Middletown, NY 10940

    Welcome to easy, carefree living in the highly sought-after 55+ community of Wildflower at Wallkill. This beautifully maintained two-bedroom ranch offers the perfect blend of comfort, style, and convenience, all set within a vibrant, amenity-rich neighborhood. This home has been meticulously cared for, including fresh paint and new carpeting, ensuring a move-in-ready experience. Step inside to

    Patricia Sassi RE/MAX Benchmark Realty Group

    19 Sunflower St, Middletown, NY 10940
  • /40

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 2,427 Sq Ft

    3 Arden Ct, Middletown, NY 10940

    Welcome to 3 Arden Court, a well-maintained townhouse-style single-family home located on a quiet cul-de-sac in Middletown. Built in 2008, this home offers 3 bedrooms, 2.5 baths, and over 2,400 square feet of living space across three finished levels, providing flexibility for everyday living, working from home, or entertaining. The main level features an open layout with hardwood floors, a

    Justin Jordan Keller Williams Realty

    3 Arden Ct, Middletown, NY 10940
  • /4

    $470,000

    • 3 Beds
    • 2.5 Baths
    • 1,723 Sq Ft

    22 Atwood Dr, Middletown, NY 10940

    Coming Soon! Beautiful 3 BR, 2.5 baths.

    Kelly Roebuck Curasi Realty, Inc.

    22 Atwood Dr, Middletown, NY 10940
  • /36

    $499,900

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

    65 Maureen Dr, Middletown, NY 10940

    Welcome to the perfect place to purchase your home in the highly sought-after Minisink Valley School District! Perfectly situated in the desirable Robins Meadows community, this lovingly maintained raised ranch offers the ideal balance of comfort, style, and everyday convenience, all set within a peaceful, friendly neighborhood.Step inside to discover gleaming hardwood floors that flow

    Frank Muccari Cronin & Company Real Estate

    65 Maureen Dr, Middletown, NY 10940
  • /39

    $490,000

    • 3 Beds
    • 2.5 Baths
    • 2,167 Sq Ft

    76 Magnolia Park Rd, Middletown, NY 10940

    Now available in the sought-after Magnolia Park Community. This well-maintained 3-bedroom, 2.5-bath townhouse in the heart of Middletown offers three spacious levels, a sun-filled main floor featuring hardwood floors, an open-concept living and dining area, and a modern kitchen with granite countertops and generous cabinet space. The primary suite boasts a walk-in closet and a luxurious bath with

    Ryan Degnan Howard Hanna Rand Realty

    76 Magnolia Park Rd, Middletown, NY 10940
  • /48

    $850,000

    • 3 Beds
    • 3 Baths
    • 4,090 Sq Ft

    464 Union School Rd, Middletown, NY 10941

    Nestled on a private 5.1-acre property, this custom contemporary Cape-style home offers the perfect balance of luxury, comfort, and natural beauty. Thoughtfully designed with refined finishes and exceptional living spaces, this residence creates an inviting retreat while still being close to the many attractions of the Hudson Valley. Step inside to discover a bright and spacious main level

    Colin Seitz RE/MAX Benchmark Realty Group

    464 Union School Rd, Middletown, NY 10941
  • /23

    $490,000

    • 3 Beds
    • 2.5 Baths
    • 2,191 Sq Ft

    19 Magnolia Park Rd, Middletown, NY 10940

    Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen with granite

    Daniel Amodeo AMO Realty

    19 Magnolia Park Rd, Middletown, NY 10940
  • /22

    $329,000

    • 2 Beds
    • 2.5 Baths
    • 1,473 Sq Ft

    209 Deer Ct Dr, Middletown, NY 10940

    Welcome to Deer Run, this inviting condo in the heart of Middletown, NY, where convenience meets comfort. Perfectly situated for commuters, this home offers easy access to major highways, shopping, dining, and transportation, making daily travel a breeze. Enjoy the best of suburban living with a peaceful atmosphere, all while being close to everything you need. Whether you're starting out,

    Beverly Huaman Howard Hanna Rand Realty

    209 Deer Ct Dr, Middletown, NY 10940
  • /20

    $225,000

    • 2 Beds
    • 2 Baths
    • 1,000 Sq Ft

    366 Concord Ln, Middletown, NY 10940

    NEW JUST RENOVATED in August 2024. Spacious 2 bedroom. 2 full bath condo. INVESTOR? THIS CAN BE RENTED IMMEDIATELY AFTER CLOSING. 1st FLOOR Private entrance, all new appliances in 2024, all new floors throughout, new washer/ dryer in unit! Spacious unit with en suite primary bedroom and additional full bath . Large second bedroom. Walk in closet. Lovely breakfast bar. Plenty of parking. Lovely

    Yolanda Hoey More and More Real Estate

    366 Concord Ln, Middletown, NY 10940

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$401,500
Median Single Family Sale Price
$425,000
Median Townhouse Sale Price
$441,250
Median 2 Bedroom Sale Price
$275,730
Median 1 Bedroom Sale Price
$180,000
Average Price Per Sq Ft
$247
Number of Homes for Sale
90
Last 12 months Home Sales
490
Months of Supply
2.20
Median List Price
$405,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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