30

Middletown, NY Homes for Sale with Pool

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  • /25

    $160,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 735 Sq Ft

    226 Concord Ln, Middletown, NY 10940

    Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has

    Agent Photo

    Lynelle Alessi

    KW Hudson Valley United

    226 Concord Ln, Middletown, NY 10940
  • /32

    $1,680,000

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

    3 Bristol Dr, Middletown, NY 10941

    Welcome to 3 Bristol Drive, 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 suits, 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

    3 Bristol Dr, Middletown, NY 10941
  • /50

    $550,000

    $70K PRICE DROP
    • 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

    KW Hudson Valley United

    179 Reservoir Rd, Middletown, NY 10940
  • /43

    $399,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    83 Deer Ct Dr, Middletown, NY 10940

    Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located in the highly desirable Deer Run complex. This move-in-ready home features laminate flooring throughout, with tile flooring in the kitchen and bathrooms. The kitchen was tastefully updated in 2020, along with the heating and cooling system, which is electronically controlled and offers a high-efficiency SEER

    Agent Photo

    Dulce M Ferrera

    KW Hudson Valley United

    83 Deer Ct Dr, Middletown, NY 10940
  • /45

    $464,999

    Open Sat 12PM - 2PM
    • 3 Beds
    • 2.5 Baths
    • 1,966 Sq Ft

    45 Brola Rd, Middletown, NY 10940

    Welcome to this inviting bilevel home situated on 1.2 level acres in the Minisink School District. The property offers a wonderful combination of space, comfort, and outdoor enjoyment, featuring a fully fenced backyard, spacious deck, and above-ground pool, perfect for relaxing or entertaining.Inside, hardwood flooring runs throughout the main living areas, creating a warm and inviting feel.

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    45 Brola Rd, Middletown, NY 10940
  • /2

    $359,000

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

    21 Black Stallion Ct, Middletown, NY 10940

    Welcome to this inviting, freshly painted, updated 3-bedroom, 1.5-bathroom home in The Meadows community~Main floor offers kitchen-with brand new cabinets, new stainless steel appliances, granite countertops, tile backsplash, roomy dining area, bright and expansive living room with large bay window and half bath~Door from the kitchen leads to the large deck perfect for relaxing or entertaining

    Liene Kasparsons Keller Williams Realty

    21 Black Stallion Ct, Middletown, NY 10940
  • /50

    $999,500

    $101K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,787 Sq Ft

    441 Scotchtown Collabar Rd, Middletown, NY 10941

    Colonial Masterpiece - This one-of-a-kind Hudson Valley residence artfully combines authentic, historic character with flawless contemporary design set on a bucolic, level parcel. The c. 1790’s antique colonial portion of the home features a timeless natural stone facade, standing seam roof, and welcoming red front door evoking true period charm. An architecturally inspired contemporary wing clad

    Jacob Matthews Ellis Sotheby's Intl Realty

    441 Scotchtown Collabar Rd, Middletown, NY 10941
  • /49

    $579,000

    • 4 Beds
    • 3 Baths
    • 2,368 Sq Ft

    34 Hawthorne Dr, Middletown, NY 10940

    Welcome to Wildflower at Wallkill, Orange County's premier 55+ community! Something Special! This 4 BR, 3 bath beauty is open and sun filled with vaulted ceilings and lovely detailed chair railings! 10 ft. ceilings and new wood floors throughout 1 st floor! Large LR opens to DR! Kitchen with island and undercounter lighting opens to vaulted family room with gas fireplace! Primary suite is on

    Linda Clark Hudson Valley Griffith

    34 Hawthorne Dr, Middletown, NY 10940
  • /27

    $399,900

    $50K PRICE DROP
    • 5 Beds
    • 3 Baths

    37 Monhagen Ave, Middletown, NY 10940

    Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and

    Isaiah Lopez KW Hudson Valley United

    37 Monhagen Ave, Middletown, NY 10940
  • /32

    $559,000

    $40K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,929 Sq Ft

    1 Parkview Dr, Middletown, NY 10940

    Welcome to 1 Parkview Dr. in beautiful Presidential Park in Middletown, NY. Located on a corner lot, this expanded raised ranch shines. Gleaming hardwood floors and spacious room size are only some if it's great features. Eat in kitchen boasts an atrium that looks out to its lovely landscaped backyard. Spend time in this space and you'll feel like you're on vacation. Beautiful inground pool is

    Marie Altieri Howard Hanna Rand Realty

    1 Parkview Dr, Middletown, NY 10940
  • /36

    $579,000

    $21K PRICE DROP
    • 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 lifeA grand foyer opens to a bright, airy layout with high ceilings, large windows,

    Michelle Gruberger Real Estate Circuit Inc

    669 Mountain Rd, Middletown, NY 10940
  • /30

    $839,000

    $10K 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
  • /47

    $799,900

    Open Sat 11:30AM - 1:30PM
    • 4 Beds
    • 2.5 Baths
    • 2,956 Sq Ft

    158 Reiss Rd, Middletown, NY 10940

    Built in 2019, this modern farmhouse colonial pairs timeless style with thoughtful design, custom details and an exceptional setting in the Minisink Valley School District. Inside, rustic elegance takes center stage with beautiful wood accents, barn doors and warm finishes throughout. Designed with entertaining in mind, the chef’s kitchen features quartz countertops, an oversized island,

    Danielle Bartula Howard Hanna Rand Realty

    158 Reiss Rd, Middletown, NY 10940
  • /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
  • /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
  • /49

    $370,000

    • 3 Beds
    • 2.5 Baths
    • 1,692 Sq Ft

    15 Old Anvil Ln, Middletown, NY 10940

    Welcome to 15 Old Anvil Ln, Middletown, a lovingly cared for end unit townhouse in the sought after "The Meadows" community. This unit has been lived in and cared for by the same owners for approximately 40 years. The owner is a builder so he has not skipped on his own improvements and care. The unit offers 3 bedrooms and 2.5 bathrooms, a kitchen and formal dining room with a slider to a

    Valeria Rios KW Hudson Valley United

    15 Old Anvil Ln, Middletown, NY 10940
  • /39

    $505,000

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

    111 Jasmine Dr, Middletown, NY 10940

    Welcome to Wildflower at Wallkill, one of the Hudson Valley's premier 55+ communities, where beautifully maintained grounds, outstanding amenities, and a true sense of community create an exceptional place to call home. Residents enjoy a beautiful clubhouse, fitness center, business center, indoor and outdoor swimming pools, tennis courts, recreation facilities, gated entry, and professionally

    Christina D'Altilio Coldwell Banker Choice Prop.

    111 Jasmine Dr, Middletown, NY 10940
  • /50

    $499,900

    • 3 Beds
    • 2.5 Baths
    • 1,781 Sq Ft

    37 Meadow View Dr, Middletown, NY 10940

    Welcome to this beautifully updated end-unit townhouse with numerous upgrades completed in 2023! The bright and open main level features hardwood flooring, a spacious kitchen with granite countertops, a complementary tile backsplash, stainless steel appliances, abundant cabinetry, a large center island, pendant lighting, and recessed lighting. The kitchen flows seamlessly into the dining area and

    Jie Liu KW Hudson Valley United

    37 Meadow View Dr, Middletown, NY 10940
  • /50

    $625,000

    • 3 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    8 Green Ct, Middletown, NY 10940

    Welcome to this well-maintained 3-level townhome in The Fairways, a gated community conveniently located next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, restaurants, and everyday conveniences. This home offers a 2-car garage, a finished lower level with direct garage access, and a functional floor plan designed for comfortable everyday living.

    Jie Liu KW Hudson Valley United

    8 Green Ct, Middletown, NY 10940
  • /9

    $275,000

    • 3 Beds
    • 1.5 Baths
    • 1,188 Sq Ft

    18 Black Stallion Ct, Middletown, NY 10940

    This inviting 3-bedroom, 1.5-bath townhome offers comfort, space and a welcoming layout. Owned by the same family for over 50 years, this home is now ready for its next chapter. Inside, you’ll find a large, comfortable living room that’s perfect for gathering and relaxing. The eat-in kitchen has been updated with new flooring and appliances, making it both functional and stylish. New carpeting

    Jennifer Kubler eRealty Advisors, Inc

    18 Black Stallion Ct, Middletown, NY 10940
  • /37

    $525,000

    • 3 Beds
    • 2.5 Baths
    • 1,952 Sq Ft

    24 Beth Dr, Middletown, NY 10941

    Your home is this fully renovated 3-bedroom property that seamlessly blends modern interior elegance with an extraordinary backyard oasis! Step inside to an airy, light-filled open-concept floor plan showcasing fresh updates throughout, including sleek new flooring, modern lighting fixtures, and spa-inspired renovated bathrooms. The open gourmet kitchen serves as the heart of the home,

    Marc Cineus Howard Hanna Rand Realty

    24 Beth Dr, Middletown, NY 10941
  • /19

    $560,000

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

    77 Upper Rd, Middletown, NY 10940

    Accepted Offer- Continue Showing for Back up. 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 partially finished basement with enough 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
  • /33

    $499,999

    Open Sat 1PM - 3PM
    • 4 Beds
    • 2 Baths
    • 1,861 Sq Ft

    678 Prosperous Valley Rd, Middletown, NY 10940

    Welcome to 678 Prosperous Valley Road, a beautifully renovated Colonial nestled on 0.80 acres in the desirable Town of Middletown. Combining timeless character with modern upgrades, this move-in-ready home offers 4 spacious bedrooms, 2 full bathrooms, and approximately 1,861 square feet of thoughtfully updated living space.Recent improvements include a stunning remodeled kitchen, fully

    Yonauris Gonzalez Then eXp Realty

    678 Prosperous Valley Rd, Middletown, NY 10940
  • /45

    $795,000

    $30K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,276 Sq Ft

    34 Stapleton Ct, Middletown, NY 10940

    Seller ready to go! This stunning four-bedroom Colonial is nestled on 1.3 acres at the end of a peaceful cul-de-sac, backing up to the scenic Hunter Nature Preserve. Solar panels owned, utility bills less than $25/month. Enjoy relaxing evenings on the spacious rocking chair front porch. The updated kitchen features beautiful granite countertops and a custom backsplash, perfect for culinary

    Annie Hansen Howard Hanna Rand Realty

    34 Stapleton Ct, Middletown, NY 10940
  • /20

    $146,900

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 735 Sq Ft

    394 Concord Ln, Middletown, NY 10940

    A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy

    Carol Scully Keller Williams Realty

    394 Concord Ln, Middletown, NY 10940
  • /23

    $490,000

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

    19 Magnolia Park Rd, Middletown, NY 10940

    BACK ON MARKET: 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

    Daniel Amodeo AMO Realty

    19 Magnolia Park Rd, Middletown, NY 10940
  • /49

    $1,750,000

    • 3 Beds
    • 3.5 Baths
    • 3,108 Sq Ft

    704 Mountain Rd, Middletown, NY 10940

    At 1,070 feet atop the Shawangunk Ridge, the view is the first thing that gets you. A sweeping panorama of valleys, ridgelines, and endless sky that shifts by the hour and somehow never stops feeling dramatic. It’s the kind of setting that instantly slows your pulse.The approach sets the tone: steep dark gables, a gated entry, and a herringbone brick courtyard leading to double doors tucked

    Monica Schwerberg Compass Greater NY, LLC

    704 Mountain Rd, Middletown, NY 10940
  • /31

    $278,000

    $12K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,146 Sq Ft

    66 Deer Ct Dr, Middletown, NY 10940

    Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and good natural light. Building entry with controlled access and interior access to the second-floor unit. The living and dining areas are combined and connect to a galley kitchen with a pass-through opening. The primary bedroom features a walk-in closet and a private full bathroom. New carpet was installed in

    Jie Liu KW Hudson Valley United

    66 Deer Ct Dr, Middletown, NY 10940
  • /47

    $599,000

    Open Sat 2PM - 4PM
    • 4 Beds
    • 2.5 Baths
    • 2,832 Sq Ft

    1215 Route 211 W, Middletown, NY 10940

    Situated on 2.8 private acres in Mount Hope, NY, within the highly regarded Minisink Valley School District, this 4-bedroom, 2.5-bath Colonial offers 2,832 square feet of living space designed for light, space, and ultimate flexibility. Intentionally selected and custom-sited using Frank Lloyd Wright design principles, the modular home is strategically oriented on the land to maximize natural

    Matthew Gibbs KW Hudson Valley United

    1215 Route 211 W, Middletown, NY 10940
  • /41

    $369,900

    $79K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    202 Concord Ln Unit 202, Middletown, NY 10940

    Welcome to Buttonwood Hills! This spacious 3-bedroom, 2.5-bath townhouse offers comfortable, low-maintenance living in one of Middletown's most convenient locations. Featuring a bright and functional layout, the main level includes a generous living room, dining area, updated kitchen, convenient half bath, and in-unit laundry. Upstairs, you'll find a spacious primary bedroom along with two

    Soleil Jackman Howard Hanna Rand Realty

    202 Concord Ln Unit 202, Middletown, NY 10940

Home Price Trends

Median Sale Price
$415,000
Median Single Family Sale Price
$430,000
Median Townhouse Sale Price
$441,250
Median 2 Bedroom Sale Price
$302,500
Median 1 Bedroom Sale Price
$165,000
Average Price Per Sq Ft
$252
Number of Homes for Sale
147
Last 12 months Home Sales
472
Months of Supply
3.70
Median List Price
$419,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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