24

Middletown, NY Homes for Sale with Pool

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  • /41

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 2,672 Sq Ft

    1583 Mountain Rd, Middletown, NY 10940

    Looking for your piece of paradise?... You just found it! This great contemporary home offers 4 to 5 bedrooms, 2.5 bathrooms, a 2 car garage on 1 acre of land. Large windows, vaulted ceilings and skylights allow the flow of natural light throughout the house. You'll also find beautiful hardwood floors throughout. Kitchen was updated in 2020 offering plenty of cabinets and stainless steel

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 208-3559

    1583 Mountain Rd, Middletown, NY 10940
  • /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
  • /49

    $599,999 Open Sun 12PM - 3PM

    • 5 Beds
    • 3.5 Baths
    • 2,504 Sq Ft

    166 Brown Rd, Middletown, NY 10941

    Charming 5-Bedroom, 3.5-Bathroom Home with In-ground Pool, Modern Updates & Historic AppealStep into this modernized historic home, where timeless charm meets contemporary luxury. This 5-bedroom, 3.5-bathroom beauty features two primary suites, including a first-floor primary with an ensuite bathroom, offering flexibility and privacy. The updated kitchen includes quartz countertops,

    Harmoni VanEtten eXp Realty

    166 Brown Rd, Middletown, NY 10941
  • /35

    $789,000

    • 5 Beds
    • 3.5 Baths
    • 4,255 Sq Ft

    24 Woodside Ct, Middletown, NY 10941

    This stunning UPGRADED COLONIAL offers rare privacy at the end of a quiet cul-de-sac, just 10 mins outside of Middletown. Great Location!! A dream kitchen with high-end appliances, marble Carrara countertops, convection microwave, and double oven air fryer. Bonus room over the garage. Hardwood and tile floors throughout, marble / granite countertops in all baths, three walk-in closets,

    Philip Barnao eXp Realty

    24 Woodside Ct, Middletown, NY 10941
  • /38

    $575,000

    • 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
  • /34

    $599,999

    • 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
  • /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

    $660,000

    • 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
  • /28

    $375,000

    • 3 Beds
    • 1.5 Baths
    • 1,856 Sq Ft

    53 Fair Oaks Rd, Middletown, NY 10940

    Welcome to this charming ranch-style home set on 4.8 acres, consisting of two lots (2.3 and 2.5 acres), offering comfort, convenience, and room to enjoy both inside and out. This 3-bedroom, 1.5-bath home features a bright and inviting eat-in kitchen with granite countertops, perfect for casual meals or gatherings. This home comes equipped with central air conditioning and a whole-house generator

    Karen Green-Nelson Coldwell Banker Realty

    53 Fair Oaks Rd, Middletown, NY 10940
  • /41

    $649,900 Open Sun 12PM - 2PM

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

    30 Eagles Way, Middletown, NY 10940

    Welcome to 30 Eagles Way — A Rare Detached Townhome in The Fairways at Wallkill. Tucked at the end of a quiet cul-de-sac within the prestigious gated community of The Fairways, this meticulously maintained 3-bedroom, 2.5-bathroom single-family detached townhouse offers over 2,430 sqft of refined living space in the heart of the Hudson Valley.Main Level Living with Modern Elegance: Step inside

    Amanda Brehm Keller Williams Hudson Valley

    30 Eagles Way, Middletown, NY 10940
  • /36

    $494,900

    • 3 Beds
    • 2.5 Baths
    • 1,858 Sq Ft

    38 Cobblestone Ln, Middletown, NY 10940

    Must see !!! 3 bedroom 2.5 bathroom townhome with crown molding throughout 3 levels of living space Hardwood floors (Acacia)in most rooms with the exception of 1 bedroom and basement which is carpeted.Home features living room with gas fireplace custom mantle and granite surround ,sliding doors to patio and private backyard.2 story open foyer with chandelier. Study / office with French doors for

    Sandra Johnson Keller Williams Realty

    38 Cobblestone Ln, Middletown, NY 10940
  • /40

    $489,900

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    11 Cobblestone Ln, Middletown, NY 10940

    Welcome to this bright and spacious 3-bedroom, 2.5-bath townhouse, that’s perfect for today’s busy lifestyle. The spacious layout is filled with natural light, creating a warm and inviting atmosphere for all to gather. The main level offers plenty of room for both everyday living and entertaining, while the upper level features comfortable bedrooms, including a primary suite with its own private

    Antoinette Gundersen HomeSmart Homes & Estates

    11 Cobblestone Ln, Middletown, NY 10940
  • /39

    $489,000

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

    4 Putters Way, Middletown, NY 10940

    Beautiful townhouse-style condo in the gated community of The Fairways. Walk in to a tiled foyer leading you to a den with full egress windows. Built-in cabinets for display and for storage. Up the stairs you have a beautiful living room with 2nd floor large windows with views overlooking the charming street. Corner gas fireplace, more built-ins for display and for entertaining ease. The

    Susanne Dermigny Howard Hanna Rand Realty

    4 Putters Way, Middletown, NY 10940
  • /32

    $1,888,000

    • 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
  • /47

    $499,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 2,032 Sq Ft

    29 Keasel Rd, Middletown, NY 10940

    Welcome to 29 Keasel Road—a private oasis that perfectly blends elegance, comfort, and convenience. Just minutes from the expressway and premier shopping, this stunning home boasts thoughtful upgrades including a brand-new dishwasher and gutters (2024) and well-maintained windows (5–10 years). Step outside to your own resort-style retreat featuring a sparkling in-ground pool, serene functioning

    Ramanjit Dhanoa eXp Realty

    29 Keasel Rd, Middletown, NY 10940
  • /35

    $489,000

    • 3 Beds
    • 2.5 Baths
    • 2,763 Sq Ft

    38 Highrose Ridge Way, Middletown, NY 10940

    Welcome to a beautifully maintained 6-year-young home offering comfort, style, and an unbeatable location. This spacious residence features 3 generously sized bedrooms and multiple living spaces, including a warm and inviting living room and a bright, open family room perfect for gatherings or quiet evenings in.The heart of the home is the well-appointed kitchen, offering plenty of counter

    Donna Reese Keller Williams Hudson Valley

    38 Highrose Ridge Way, 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

    $643,000

    • 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
  • /34

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 1,919 Sq Ft

    110 Deer Ct Dr, Middletown, NY 10940

    BACK ON THE MARKET! Welcome to 110 Deer Court Drive, a bright and well maintained 3-bedroom, 2.5-bath unit in the highly sought-after Deer Run community in Middletown, NY. This inviting home features a spacious open floor plan filled with natural light, perfect for both everyday living and entertaining. The living room offers a cozy wood-burning fireplace while the separate dining area flows

    Patricia Sassi RE/MAX Benchmark Realty Group

    110 Deer Ct Dr, 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
  • /16

    $284,900

    • 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
  • /13

    $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
  • /38

    $359,000 Open Sun 1PM - 3PM

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

    33 Red Barn Ln, Middletown, NY 10940

    Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhouse perfectly situated near schools, shopping, and major highways for an easy commute. Pride of ownership is evident throughout with spacious living areas, a functional layout, and thoughtful updates. The finished lower level offers additional living space, while the 1-car garage provides convenience and storage. Set at the end of

    Donna Reese Keller Williams Hudson Valley

    33 Red Barn Ln, Middletown, NY 10940

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$393,250
Median Single Family Sale Price
$410,750
Median Townhouse Sale Price
$400,000
Median 2 Bedroom Sale Price
$263,250
Median 1 Bedroom Sale Price
$175,000
Average Price Per Sq Ft
$242
Number of Homes for Sale
115
Last 12 months Home Sales
500
Months of Supply
2.80
Median List Price
$399,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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