23

Middletown, NY Homes for Sale with Pool

Section Image
  • /21

    $599,000

    • 4 Beds
    • 3 Baths
    • 2,552 Sq Ft

    125 Whipple Rd, Middletown, NY 10940

    Discover the perfect blend of serenity and comfort in this stunning 4-bedroom, 3-bathroom raised ranch nestled on a sprawling 1.5-acre lot in the heart of Middletown, NY. As you step inside, the heart of the residence, a spacious and sunlit living area, invites family gatherings and effortless entertaining. Culinary enthusiasts will delight in the modern kitchen, boasting sleek appliances and

    Eboni Navas Julia B Fee Sothebys Int. Rlty

    125 Whipple Rd, Middletown, NY 10940
  • /43

    $635,000

    • 4 Beds
    • 3 Baths
    • 3,328 Sq Ft

    58 White Bridge Rd, Middletown, NY 10940

    Welcome to your own Alpine retreat in the heart of the Hudson Valley and in the Minisink school district! Inspired by traditional German design, this warm and inviting home offers a harmonious blend of rustic charm and modern functionality. Nestled on 1.2 acres of beautifully manicured grounds, the property exudes pride of ownership and has been meticulously maintained by its current owners. Step

    Patricia Sassi RE/MAX Benchmark Realty Group

    58 White Bridge Rd, Middletown, NY 10940
  • /50

    $875,000

    • 4 Beds
    • 4 Baths
    • 3,699 Sq Ft

    21 Lincoln Terrace Unit 19, Middletown, NY 10940

    Step into a rare and iconic mid-century modern residence, masterfully designed and once inhabited by renowned local architect Dennis Jurow. Tucked away on a private and mature one-acre lot in Middletown, this 4,000+ square foot home is a true celebration of 1970s contemporary design—thoughtfully preserved with original details throughout. This one-of-a-kind home features ten sliding glass doors

    Patricia Sassi RE/MAX Benchmark Realty Group

    21 Lincoln Terrace Unit 19, Middletown, NY 10940
  • /35

    $689,000

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

    669 Mountain Rd, Middletown, NY 10940

    Nestled in the Minisink School District | 6 bedrooms, |3 bathrooms| chef’s kitchen| perfect for those who love to cook and entertain. The double-sided fireplace*adds a cozy touch, while the inground pool makes it an ideal retreat.Set on 3.38 acres the home is surrounded by lush greenery, providing a peaceful and private atmosphere. The Colonial and Contemporary architectural style blends

    Michelle Gruberger Real Estate Circuit Inc

    669 Mountain Rd, Middletown, NY 10940
  • /58

    $699,000

    • 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 Find Advisors

    5 Wawayanda Place, Middletown, NY 10940
  • /36

    $668,900

    • 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
  • /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
  • /50

    $645,000

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

    8 Green Ct, Middletown, NY 10940

    This well-maintained 3-level townhome sits within a luxury gated community of The Fairways, right next to a golf course and just minutes from major highways, Garnet Health Medical Center, shopping, and restaurants. The home offers a 2-car garage, a finished basement with garage-level entry, and a practical layout designed for comfortable living. Hardwood floors span the main level, which features

    Jie Liu Keller Williams Hudson Valley

    8 Green Ct, Middletown, NY 10940
  • /15

    $465,000

    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    30 Avoncroft Ln, Middletown, NY 10940

    **Welcome to 30 Avoncroft Lane, Middletown, NY!**This beautifully maintained 3-bedroom, 2.5-bath townhouse is nestled in the desirable Woodside Knolls community. Step inside to discover updated flooring throughout and a bright, versatile layout perfect for modern living. The spacious finished basement offers endless possibilities—use it as a home gym, playroom, family room, or your own

    Cindy-Lee Dorcely Keller Williams Hudson Valley

    30 Avoncroft Ln, Middletown, NY 10940
  • /38

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 2,144 Sq Ft

    10 Frederick St, Middletown, NY 10941

    Move in ready 4 bedroom/2.1 Bath with so many updates. Elegant entrance with rod iron spindles, Modern chandelier, Picture Window, Slate stone landing. Gourmet Kitchen offers Custom designed Kraftmaid collection cabinets with Chef grade range hood, Porcelain backsplash, Pot Filler, Large Island/Waterfall with built in space for microwave, Quartz countertops, Samsung Stainless steel appliances,

    Angelo Acierno Keller Williams Realty

    10 Frederick St, Middletown, NY 10941
  • /47

    $974,500

    • 4 Beds
    • 2.5 Baths
    • 3,245 Sq Ft

    28 Feiertag Rd, Middletown, NY 10941

    Welcome to this beautifully maintained Colonial nestled on more than 2 acres of serene, landscaped property. This stately home combines classic charm with modern comforts, featuring a grand front porch and exceptional curb appeal.Inside, you’ll find spacious living areas with abundant natural light, perfect for both everyday living and entertaining. The updated kitchen flows effortlessly

    Danielle Reese Christie's Int. Real Estate

    28 Feiertag Rd, Middletown, NY 10941
  • /30

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,633 Sq Ft

    306 S Centerville Rd, Middletown, NY 10940

    Staycation in the Country – An Entertainer’s Dream! Discover the perfect blend of comfort, beauty, and functionality in this spacious 4-bedroom, 2.5-bath colonial nestled on a serene 1.6-acre lot in Minisink School District. With room to spread out, incredible indoor and outdoor spaces, this home is your year-round getaway—without ever leaving your driveway. The heart of the home is a show

    Johan Tola Keller Williams Realty Group

    306 S Centerville Rd, Middletown, NY 10940
  • /40

    $489,000

    • 3 Beds
    • 2.5 Baths
    • 2,491 Sq Ft

    5 Cornwall Ln, Middletown, NY 10940

    Welcome to this ending unit townhouse nestled in the community of Woodside Knolls. This beautifully maintained home offers 3 spacious bedrooms, 2.5 bathrooms, and an attached 2-car garage. With over 2,400 square feet of living space, this residence seamlessly blends comfort, and functionality. Step inside to discover the Oak Hardwood Floors throughout the main level. The bright and airy living

    Wenpeng Guan Keller Williams Hudson Valley

    5 Cornwall Ln, Middletown, NY 10940
  • /32

    $549,000

    • 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

    Marie Altieri Howard Hanna Rand Realty

    1 Parkview Dr, Middletown, NY 10940
  • /23

    $318,000

    • 2 Beds
    • 2.5 Baths
    • 1,831 Sq Ft

    12 Deer Ct Dr, Middletown, NY 10940

    Spacious Townhouse in a Prime Location!This well-located townhouse offers the perfect combination of space, comfort, and convenience. Ideal for commuters and anyone who enjoys being close to all the action. Just minutes from major highways, the home provides easy access to shopping centers, restaurants, and everyday essentials. For city bound travelers, getting around is simple. With nearby

    Beverly Huaman Howard Hanna Rand Realty

    12 Deer Ct Dr, Middletown, NY 10940
  • /26

    $265,000

    • 2 Beds
    • 2 Baths
    • 1,146 Sq Ft

    162 Deer Ct Dr, Middletown, NY 10940

    Beautiful Condo in a Prime Location!Experience the perfect blend of comfort and convenience in this ideally located condo, perfect for commuters and those who love being close to the action. Just minutes from major highways, this home offers easy access to shopping centers, restaurants, and daily essentials.For city bound travelers, transportation is a breeze with nearby access to the

    Beverly Huaman Howard Hanna Rand Realty

    162 Deer Ct Dr, Middletown, NY 10940
  • /16

    $299,900

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

    4 Red Barn Ln, Middletown, NY 10940

    **BACK ON THE MARKET**...ROLLING MEADOWS! Low HOA! 3 Bedrooms! 1 1/2 Bathrooms! Eat In Kitchen! Large Living Room! Master Bedroom with Walk In Closet! Sliders to Fenced in Yard! Perfect Commuter Location! Close to Major Highways, Trains, Buses and Shopping! Walk to Clubhouse, Community Pool, Playground, Tennis and Basket Ball!

    Amanda Dnistrian ARC Realty 1 in Sales

    4 Red Barn Ln, Middletown, NY 10940
  • /46

    $624,900

    • 3 Beds
    • 3.5 Baths
    • 3,013 Sq Ft

    1 Country Club Dr, Middletown, NY 10940

    Simply The Best! Here it is! The largest end unit in the premier luxury, maintenance free gated community of Fairways of Wallkill. The original owners included every upgrade available when choosing options and now it can be yours! Starting with the privacy, lush landscaping and common area, this was an premium lot upgrade. This Beaumont model offers over 3000 sq feet and four levels of lavish

    Karen Taphorn Howard Hanna Rand Realty

    1 Country Club Dr, Middletown, NY 10940
  • /12

    $142,900

    • 1 Bed
    • 1 Bath
    • 740 Sq Ft

    228 Concord Ln Unit 228, Middletown, NY 10940

    ESTATE SALE – Prime Investment Opportunity!Discover value in this estate sale offering—a 1-bedroom, 1-bathroom second-floor unit located in Middletown’s Buttonwood Hills community. Ideal for investors seeking strong rental potential or buyers in search of a low-maintenance, conveniently located home. Situated in a commuter-friendly location, it's close to major highways, colleges, shopping

    Yasmine Delgado BHG Real Estate Green Team

    228 Concord Ln Unit 228, Middletown, NY 10940
  • /34

    $610,000

    • 4 Beds
    • 3.5 Baths
    • 2,188 Sq Ft

    26 Kyleigh Way, Middletown, NY 10940

    Welcome to this stunning, 5-year-young home located in the desirable Sunrise Hills development.This beautifully maintained residence offers 4 spacious bedrooms, 3 full bathrooms, and 1 half bathroom. The grand cathedral entryway features an elegant chandelier that can be admired from both inside and out, highlighting the top landing of the staircase.The large fourth bedroom is

    Delroy Smith List 4 Less Realty

    26 Kyleigh Way, Middletown, NY 10940
  • /43

    $347,000

    • 2 Beds
    • 1 Bath
    • 1,254 Sq Ft

    203 Watkins Ave, Middletown, NY 10940

    Welcome Home! As you enter this nicely maintained capecod you'll notice the curved archway entry. To the left is a bonus room that could be used as an office/bedroom. The living room/ dining area combo has beautiful refinished hardwood floors. In addition to a full bathroom, kitchen with granite countertops, stainless steel appliances, white subway tile backsplash, and luxury vinyl plank flooring

    Brenda Otero HomeSmart Homes & Estates

    203 Watkins Ave, Middletown, NY 10940
  • /36

    $579,000

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

    360 New Vernon Rd, Middletown, NY 10940

    Welcome to 360 New Vernon Rd in Middletown, Recently painted 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

    Felix Pena RE/MAX Benchmark Realty Group

    360 New Vernon Rd, Middletown, NY 10940
  • /32

    $1,888,000 Coming Soon

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

    3 Bristol Dr, Middletown, NY 10941

    Amazing Mini Mansion Luxury Hse on this one ! For those that look for the very best and finest that the Hudson Valley has to offer you are sure to be amazed as you enter this 11200 plus sq ft luxurious brick colonial mansion including 3200 sq ft Indoor Pool room ! Yes you read that correctly, this home is one of the very few that features a 16 by 32 ft indoor pool attached to a 10 person jacuzzi

    Mohamed Elgoarany All American Realty Management

    3 Bristol Dr, Middletown, NY 10941

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$420,000
Median Single Family Sale Price
$541,330
Median Townhouse Sale Price
$435,000
Median 2 Bedroom Sale Price
$309,500
Median 1 Bedroom Sale Price
$180,000
Average Price Per Sq Ft
$229
Number of Homes for Sale
12
Last 12 months Home Sales
124
Months of Supply
1.20
Median List Price
$442,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
-12%
How to Buy a Home How to Finance a Home How to Sell a Home