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Middletown, NY Homes for Sale with Pool

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  • /30

    $525,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,229 Sq Ft

    17 Juniper Cir, Middletown, NY 10940

    Prepare to be impressed! This meticulously maintained home features a bright open floor plan, vaulted ceilings, and formal living and dining spaces that flow beautifully for everyday living and entertaining. A den offers flexible space for work, hobbies, or guests. Enjoy a peaceful setting that's tucked away yet conveniently close to the clubhouse and pool. Pride of ownership is evident at every

    Agent Photo

    John Olivero

    Keller Williams Realty

    (845) 448-2237

    17 Juniper Cir, Middletown, NY 10940
  • /7

    $239,888

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    218 Concord Ln, Middletown, NY 10940

    Welcome to this charming first-floor condo located in Buttonwood Hills community! With 2 bedrooms, 2 baths, and a patio, this well-maintained unit offers a galley kitchen, dining area, and living room. Enjoy access to clubhouse amenities and a community poolhouse. Ideal for those seeking convenience and community living. InteriorFeatures: Built-in Features,

    Agent Photo

    John Olivero

    Keller Williams Realty

    (845) 475-0808

    218 Concord Ln, Middletown, NY 10940
  • /36

    $630,000

    • 4 Beds
    • 2.5 Baths
    • 2,316 Sq Ft

    360 New Vernon Rd, Middletown, NY 10940

    Welcome to 360 New Vernon Rd in Middletown, a beautifully maintained home nestled on 2 acres of serene land—perfect for those seeking space, comfort, and privacy. This spacious 4-bedroom, 2.5-bath home offers over 2,300 square feet of living space with modern upgrades throughout, including a brand-new central air system, new washer & dryer, and a whole-home water purification system with reverse

    Felix Pena RE/MAX Benchmark Realty Group

    360 New Vernon Rd, Middletown, NY 10940
  • /44

    $572,000

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

    2017 Mt Hope Rd, Middletown, NY 10940

    Welcome home to this beautifully maintained, move-in-ready Colonial in a quiet country setting, just 4 miles from the Otisville Metro-North station – a commuter's dream! This spacious home offers an easy flow and open concept living, perfect for modern living. The updated kitchen is a chef's delight, featuring a large two-tiered center island with breakfast bar seating and ample storage, a large

    Sandra Spector Howard Hanna Rand Realty

    2017 Mt Hope Rd, Middletown, NY 10940
  • /58

    $760,000

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

    5 Wawayanda Place, Middletown, NY 10940

    Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 11 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 Oxford Property Group USA

    5 Wawayanda Place, Middletown, NY 10940
  • /36

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 3,088 Sq Ft

    168 S Centerville Rd, Middletown, NY 10940

    This is one of the Kind property in the Minisink School District . This Beautiful Colonial is seated on about 6.1 level acres of land all landscaped with a stream running through the back of the property allowing for fishing and relaxation either from a fantastic patio or the two decks and above ground pool to provide plenty of enjoyment of its natural surroundings.including fishing and

    Elizabeth Nemeth John J Lease REALTORS Inc

    168 S Centerville Rd, Middletown, NY 10940
  • /36

    $285,000

    • 2 Beds
    • 2 Baths
    • 1,110 Sq Ft

    110 Sycamore Dr, Middletown, NY 10940

    The wait is over! The ONLY unit currently available in Clemson Park Condominiums and lucky you ... it is a second floor unit for REALLY easy living with no neighbors above! Fresh neutral paint, brand new carpet, two year old HVAC system and all new windows are just the beginning of what you will find. One level floor plan offers an eat in kitchen with crisp white cabinets and stainless steel

    Laurel Lustgarten Howard Hanna Rand Realty

    110 Sycamore Dr, Middletown, NY 10940
  • /19

    $235,000

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

    256 Concord Ln, Middletown, NY 10940

    This fully renovated two-bedroom, two-bath condo offers modern upgrades and stylish finishes throughout. The kitchen features brand-new appliances and elegant quartz countertops, while the bathrooms boast sleek porcelain countertops. Enjoy the comfort of brand-new vinyl flooring, plush carpeting, and a new boiler, along with the convenience of an in-unit washer and dryer. Two air conditioning

    Carol Cruz Keller Williams Hudson Valley

    256 Concord Ln, Middletown, NY 10940
  • /33

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,883 Sq Ft

    7 Forest Ave, Middletown, NY 10940

    Charming 4-Bedroom Cape Cod in Middletown!Welcome to this 4-bedroom, 2-bath Cape Cod home, offering comfort, convenience, and plenty of space both inside and out. Located in a prime Middletown location near Touro College of Osteopathic Medicine, shopping, dining, schools and major highways, this home is perfect for those seeking a cozy retreat with easy access to amenities. Step inside to find a

    Claudia Lepore Keller Williams Realty

    7 Forest Ave, Middletown, NY 10940
  • /34

    $319,000

    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft

    15 Silo Ln, Middletown, NY 10940

    The owner of this home decided to give you a fresh coat of paint and add new flooring to the first level to instantly make you fall in love with the home as soon as you walk in! This home located in the desirable The Meadows Community in the Town of Wallkill. Let's talk about how this is an end unit which allows privacy and a spacious yard. When you enter you will notice the eat in kitchen that

    Pedro Garcia Curasi Realty, Inc.

    15 Silo Ln, Middletown, NY 10940
  • /21

    $410,000

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft

    10 Willow Place, Middletown, NY 10940

    Move right into this charming 3 bedroom 2 bath split level home. The property offers bonus spaces that can be converted to an office 4th bedroom, Den or more, offering flexibility to suit your needs. Step out onto a new oversized deck and enjoy a heated pool thats perfect for entertaining in style, or simply relaxing outdoors. The home is packed with updates, including new flooring throughout, an

    Jacqueline Santiago HomeSmart Homes & Estates

    10 Willow Place, Middletown, NY 10940
  • /31

    $319,900

    • 3 Beds
    • 1.5 Baths
    • 1,452 Sq Ft

    36 Old Anvil Ln, Middletown, NY 10940

    Welcome to this beautifully updated 3-bedroom, 1.5-bath end-unit townhouse, perfectly situated on a quiet cul-de-sac in Middletown.This move-in ready home features a brand new furnace, water heater, stove, microwave and refrigerator. The house features two driveways for parking which is rare in the community, and convenient side yard access—ideal for outdoor enjoyment and additional storage

    Wenpeng Guan Keller Williams Hudson Valley

    36 Old Anvil Ln, Middletown, NY 10940
  • /22

    $325,000

    • 3 Beds
    • 1.5 Baths
    • 1,056 Sq Ft

    5 Carl Place, Middletown, NY 10940

    Welcome home to 5 Carl Place, nestled in the charming Washington Heights neighborhood within the Middletown School District. This lovely residence offers 3 spacious bedrooms and 2 bathrooms, perfect for comfortable living. You'll enjoy a formal dining area for hosting gatherings and a kitchen equipped with plenty of cabinet space for all your culinary needs. The hardwood floors throughout the

    Maria Sairrino Cronin & Company Real Estate

    5 Carl Place, Middletown, NY 10940
  • /33

    $415,000

    • 2 Beds
    • 4 Baths
    • 2,161 Sq Ft

    100 Woodlake Dr, Middletown, NY 10940

    Welcome to this beautiful 2,161 square foot townhome located in the desirable Spring Hollow at Pond side community. As you enter the main level, you are greeted by a formal living room that, leading to a formal dining area perfect for entertaining. Additionally, the brand new hardwood floors add a touch of elegance and warmth throughout the living spaces. The spacious eat-in kitchen features

    Patricia Sassi RE/MAX Benchmark Realty Group

    100 Woodlake Dr, Middletown, NY 10940
  • /36

    $380,000

    • 3 Beds
    • 2 Baths
    • 1,335 Sq Ft

    25 Meyer Rd, Middletown, NY 10940

    A-Frame home in the town of Wallkill within the Minisink School District. The home is nestled amidst 1.2 acres of serene woodland and offers lots of natural lighting, vaulted ceilings, along with charm and privacy. A large wrap-around deck hugs the perimeter of the home, providing ample space for outdoor relaxation, entertaining, and soaking in the sights and sounds of nature. Inside enjoy the

    Leon Klein Keller Williams Hudson Valley

    25 Meyer Rd, Middletown, NY 10940
  • /42

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 2,055 Sq Ft

    97 Rolling Meadows Rd, Middletown, NY 10940

    Back on the Market--Fully Available--Deal Fell Through -- This meticulously maintained bi-level gem, nestled in a highly sought-after neighborhood in the Town of Wallkill, is ready for you to move right in. The main level greets you with a bright and airy living room, featuring a large picture window that fills the space with natural light and offers stunning views of the landscaped front yard.

    Kathy White Exit Realty Connections

    97 Rolling Meadows Rd, Middletown, NY 10940
  • /21

    $319,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 864 Sq Ft

    76 California Ave, Middletown, NY 10940

    A Gem - Ready to welcome its new owners, this lovely three-bedroom ranch is situated on a broad street near a park with tennis courts and a pond. It features an exceptionally large 14’ x 36’ roofed rear veranda facing a fenced backyard with an above-ground pool and a small storage barn. Many updates plus the seller’s exceptional maintenance make this home a great opportunity. It is waiting for

    Marsha Talbot Howard Hanna Rand Realty

    76 California Ave, Middletown, NY 10940
  • /48

    $1,465,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 3,805 Sq Ft

    63 Foster Rd, Middletown, NY 10941

    CHIC EQUESTRIAN HOME with SEPARATE APARTMENT in the HEART of the HUDSON VALLEY!Welcome to your Hudson Valley dream home on over 20 secluded acres and turn-key ready for your horses! A huge bonus is that it’s directly across from Highland Lakes State Park, with its 3,000 acres of preserved land and bridle paths. Simply saddle up and cross the road for a trail ride!Inside the lodge-inspired house,

    John Summerford Coldwell Banker Village Green

    63 Foster Rd, Middletown, NY 10941

Home Trends in Middletown, NY

Home Trends

Median Price (12 Mo)
$388,000
Median Single Family Price
$399,001
Median Townhouse Price
$400,000
Median 2 Bedroom Price
$260,000
Median 1 Bedroom Price
$180,000
Average Price Per Sq Ft
$237
Number of Homes for Sale
108
Last 12 months Home Sales
451
Months of Supply
2.90
Median List Price
$389,000
Median Discount From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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