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Middletown Houses for Sale

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  • /25

    $390,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft

    71 Commonwealth Ave, Middletown, NY 10940

    Welcome to the perfect blend of comfort, character, and location. Nestled in the vibrant heart of Middletown, NY—just 70 miles from NYC—this beautifully updated home offers a peaceful retreat without sacrificing proximity. Whether you’re commuting for work or play, nearby transportation options, including the Metro-North train and major highways, make travel to the city a breeze. And when you're

    Agent Photo

    Brian Caplicki

    Keller Williams Hudson Valley

    (845) 436-3953

    71 Commonwealth Ave, Middletown, NY 10940
  • /11

    $350,000

    • 4 Beds
    • 2.5 Baths
    • 2,088 Sq Ft

    19 Randall Terrace, Middletown, NY 10940

    Looking for all investors who want to buy now and get the process started in order to work on the exterior before the cold weather begins. All reasonable offers will be considered. Home features an eat in kitchen with breakfast nook, diningroom, and large step down livingroom on first floor with fireplace. Upstairs find a primary bedroom suite with separate bath. Down the hall is three more

    Agent Photo

    Lynelle Alessi

    Keller Williams Hudson Valley

    (329) 216-0798

    19 Randall Terrace, Middletown, NY 10940
  • /44

    $299,000

    • 2 Beds
    • 1 Bath
    • 792 Sq Ft

    25 Lafayette Ave, Middletown, NY 10940

    Welcome to 25 Lafayette Avenue, a charming and move-in ready 2-bedroom, 1-bath bungalow located on a quiet residential street in the heart of Middletown. This well-maintained home combines comfort and character, offering central air, stylish pet resistant vinyl flooring throughout, a sun-filled living room, and a beautifully updated kitchen with quartz countertops and ample cabinet space.The

    Agent Photo

    Kathy White

    Exit Realty Connections

    (329) 219-0502

    25 Lafayette Ave, Middletown, NY 10940
  • /20

    $399,990

    • 3 Beds
    • 2 Baths
    • 1,614 Sq Ft

    2 Saint Eve Ct, Middletown, NY 10940

    Welcome to 2 Saint Eve Ct, a versatile home offering comfort and space in a convenient Middletown location. This well-maintained property features 3 bedrooms and 2 full baths, along with a spacious eat-in kitchen perfect for everyday living and entertaining. Above the garage, a large rec room provides endless possibilities—use it as a fourth bedroom, family room, or bonus space to suit your

    Agent Photo

    Haakim Byrd

    HomeSmart Homes & Estates

    (329) 210-5621

    2 Saint Eve Ct, Middletown, NY 10940
  • /36

    $625,000

    • 4 Beds
    • 3.5 Baths
    • 2,760 Sq Ft

    214 Phillips St, Middletown, NY 10940

    Welcome to this beautiful newly built 4-bedroom, 3.5-bath home featuring a spacious 2,760 sqft layout across three levels of living space. The gourmet kitchen features an island with a breakfast bar and flows seamlessly into a large dining area. The luxurious primary suite includes a full ensuite bath with dual vanities, a shower, and a separate soaking tub, all highlighted by expansive windows.

    Donna Gray Redfin Real Estate

    214 Phillips St, Middletown, NY 10940
  • /23

    $419,900 Open Sat 12:30PM - 2:30PM

    • 3 Beds
    • 1.5 Baths
    • 1,560 Sq Ft

    6 Randall Terrace, Middletown, NY 10940

    Value lies in quality, location, and long-term potential — and this property delivers on all three. Thoughtfully renovated from top to bottom, this home is turn key and provides long-term peace of mind.Step inside to find brand-new hardwood floors throughout, a completely remodeled kitchen featuring quartz countertops, new appliances, and a complementing tile backsplash — a space built for

    Rachel Hunt Realty Promotions Inc

    6 Randall Terrace, Middletown, NY 10940
  • /4

    $415,000

    • 3 Beds
    • 2 Baths
    • 1,240 Sq Ft

    9 Genung St, Middletown, NY 10940

    Charming two-story home in the heart of Middletown! This spacious residence offers a welcoming front porch, perfect for relaxing evenings, and a practical layout filled with natural light. The home features multiple bedrooms, ample living space, and a generous yard with off-street parking. Located in a convenient neighborhood close to schools, shopping, dining, and major highways, this property

    Anthony Rivas Keller Williams Hudson Valley

    9 Genung St, Middletown, NY 10940
  • /40

    $514,999

    • 3 Beds
    • 3 Baths
    • 2,696 Sq Ft

    2 Danielle Ct, Middletown, NY 10940

    Welcome to 2 Danielle Court, a stucco home on just over a half-acre in desirable Middletown, NY. This move-in ready property features 3 bedrooms, 3 bathrooms, and a versatile media room on the lower level. Enjoy an inviting layout filled with natural light, plus an expansive backyard with endless possibilities. Located in a quiet cul-de-sac with parking for up to 6 vehicles. Comes with a FREE

    Ravyn Green YourHomeSold Guaranteed Realty

    2 Danielle Ct, Middletown, NY 10940
  • /35

    $419,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 1 Bath
    • 1,482 Sq Ft

    1 Polly Kay Dr, Middletown, NY 10940

    Welcome to this charming raised-ranch in the heart of Middletown, offering 1,482 square feet of comfortable living. The home features three spacious bedrooms, an updated kitchen and bath, and beautiful hardwood floors throughout that bring a timeless touch to every room.Downstairs, the lower level is perfect for a cozy family room, playroom, or home office—whatever best fits your

    Eva Kusmierek eXp Realty

    1 Polly Kay Dr, Middletown, NY 10940
  • /19

    $379,000

    • 3 Beds
    • 1 Bath
    • 1,100 Sq Ft

    1 Chestnut St, Middletown, NY 10940

    A must see home! This beautiful corner lot home has everything brand new inside - from the windows, closed porch, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, - all NEW. Featuring 3 bedrooms and 2 full bathrooms. It has a great size yard for your summer

    Anita S. Cristiano HomeSmart Homes & Estates

    1 Chestnut St, 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
  • /44

    $399,000

    • 4 Beds
    • 2 Baths
    • 1,634 Sq Ft

    100 Academy Ave, Middletown, NY 10940

    WELCOME HOME!!! A lovely and spacious single family property, with an extra large backyard, located in the center of Middletown is looking for its new owners, ready to move in!!!The house features a total of 4 bedrooms, 2 full baths, plus a office room, with a semi finished basement for laundry and storage. New SS washer dryer included! The 1st floor consists of a nice kitchen with

    Mordy Abelesz eXp Realty

    100 Academy Ave, Middletown, NY 10940
  • /19

    $369,000

    • 4 Beds
    • 1.5 Baths
    • 1,272 Sq Ft

    35 Woods Place, Middletown, NY 10940

    This charming four-bedroom, one-bathroom home offers comfortable living space with a versatile layout. The layout provides plenty of room with flexible living spaces. Located in a welcoming Middletown neighborhood, you'll enjoy easy access to quality schools, convenient public transportation, and shopping options just minutes away. Whether you're starting fresh or looking to upgrade, this

    Kevin Sanabria eRealty Advisors, Inc

    35 Woods Place, Middletown, NY 10940
  • /30

    $374,999 Open Sat 12PM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft

    5 Mills Ave, Middletown, NY 10940

    LOCATION, LOCATION, LOCATION! Don’t miss this charming 3 Bedroom, 1.5 Bathroom Two-Story Home located in the heart of Middletown and within the Middletown School District. This home offers unbeatable convenience—just minutes from local restaurants, shopping centers, banks, healthcare facilities, and postal services. Situated close to elementary and secondary schools, and just blocks from Orange

    Richard Baxter Keller Williams Realty

    5 Mills Ave, 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
  • /34

    $389,000

    • 3 Beds
    • 1.5 Baths
    • 1,382 Sq Ft

    120 Prospect Ave, Middletown, NY 10940

    Back on market! Buyer lost financing!! What a complete honor to represent this home, the pride of ownership is amazing! Over the last 20 years they have done so many improvements that when you view the home, it will be like they did it last week! When you arrive you will notice the long driveway that leads to a detached garage and nice sized yard. Before you enter the home, put on your

    Pedro Garcia Curasi Realty, Inc.

    120 Prospect Ave, Middletown, NY 10940
  • /26

    $399,000 Pre-Foreclosure

    • 4 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    47 Prince St, Middletown, NY 10940

    Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has been renovated in 2023 into a 4 bed/2.5 bath adding a 1st Floor Master Bedroom Suite, increasing the square footage of living space. This house has plenty of character and is better than new construction. Open Concept Layout, Enclosed Porch, Luxury Vinyl Flooring, Stainless Steel Appliances, Butcher Block

    D'Wana Haynesworth YourHomeSold Guaranteed Realty

    47 Prince St, Middletown, NY 10940
  • /44

    $324,999 Open Sat 2PM - 4PM

    • 3 Beds
    • 2 Baths
    • 1,504 Sq Ft

    20 Benton Ave, Middletown, NY 10940

    Discover the potential in this charming 3-bedroom, 2-full-bath two-story home with 1,504 sq ft of living space. Full of character and solid construction, this property offers a formal dining room and plenty of room to grow with a full unfinished attic and full, unfinished, walk-out basement featuring washer/dryer hookups.Featuring strong bones and charming original touches, this home is

    Vincent Reda Keller Williams Realty

    20 Benton Ave, Middletown, NY 10940
  • /12

    $269,900

    • 2 Beds
    • 1.5 Baths
    • 1,144 Sq Ft

    17 N Aspen Rd, Middletown, NY 10940

    This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfort and convenience! The inviting living room, filled with natural light, leads into a modern kitchen with brand-new stainless steel appliances and an adjacent washer/dryer setup. The dining room features a sliding door that opens up to a private fenced-in backyard—ideal for outdoor relaxation or

    Jonathon Lee Keller Williams Hudson Valley

    17 N Aspen Rd, Middletown, NY 10940
  • /30

    $550,000

    • 4 Beds
    • 3.5 Baths
    • 2,307 Sq Ft

    71 Watkins Ave, Middletown, NY 10940

    Exquisite Updated Colonial Residence in a Prestigious Middletown LocationDiscover timeless elegance combined with modern sophistication in this beautifully updated 4-bedroom, 3-bath Colonial home. Perfectly situated on a quiet, tree-lined street, this residence offers a seamless blend of classic architectural details and contemporary upgrades, creating a truly refined living

    Jonathon Lee Keller Williams Hudson Valley

    71 Watkins Ave, Middletown, NY 10940
  • /31

    $299,000

    • 3 Beds
    • 1.5 Baths
    • 925 Sq Ft

    6 Madeline Terrace, Middletown, NY 10940

    Welcome to 6 Madalaine Terrace, a charming ranch-style home in Middletown offering easy one-level living. This 3-bedroom, 1.5-bath home features a cozy living room, an eat-in kitchen, and a practical layout that makes the most of its space. The fenced yard is perfect for outdoor enjoyment, pets, or gardening. With a private driveway and low-maintenance exterior, this home is ideal for anyone

    Lauren Kelly Howard Hanna Rand Realty

    6 Madeline Terrace, Middletown, NY 10940
  • /20

    $275,000

    • 3 Beds
    • 1.5 Baths
    • 1,080 Sq Ft

    242 1/2 W Main St, Middletown, NY 10940

    A/O 9/2. Cute meets Convenient! This 3 bedroom, 2 bath cape cod has a lovely backyard that extends beyond Monhagen Brook. It features a 1st floor bedroom and bathroom with additional bathroom on 2nd floor for 2 bedrooms. Original hardwood floors throughout. Feel like you are priced out of today's market? Turn this charmer into the adorable cape cod it's meant to be. Literally around the corner

    Sharon Reynolds Keller Williams Hudson Valley

    242 1/2 W Main St, Middletown, NY 10940
  • /10

    $329,000

    • 3 Beds
    • 2 Baths
    • 1,350 Sq Ft

    64 Wawayanda Ave, Middletown, NY 10940

    FULLY AVAILABLE AND MOVE IN READY! 3 bedroom, 2 full bath home in a great commuter location. Home offers species kitchen with quartz counter tops & stainless steel appliances. Bright Living room, large tile baths, light fixtures and hardwood floors throughout. Cozy master bedroom with 2 closets and private bath located on the 2st floor. 2 other bedrooms and a full bath is located on main floor.

    Nathan Landau Loop Realty Inc

    64 Wawayanda Ave, Middletown, NY 10940
  • /16

    $330,000

    • 2 Beds
    • 1 Bath
    • 1,016 Sq Ft

    3 Chappell Pkwy, Middletown, NY 10940

    Move-in ready and priced to sell! This charming 2-bedroom, 1-bath home at the end of a quiet cul-de-sac in Middletown offers an open living and dining area, an eat-in kitchen, a small unfinished basement for storage, and a walk-out one-car garage with additional driveway parking. Enjoy the convenience of being minutes from historic downtown Middletown’s shops, restaurants, and the Paramount

    Antonio Sanchez Harbor Gray Real Estate LLC

    3 Chappell Pkwy, Middletown, NY 10940
  • /30

    $418,999 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,245 Sq Ft

    77 Prince St, Middletown, NY 10940

    Welcome to this beautiful well maintained contemporary two story home nestled in the heart of Middletown. Offering you a bright and spacious living room to a formal dining room, a beautiful kitchen, 3 great size bedrooms, 2.5 bathrooms with a full size basement and a car garage. Plus plenty of closets with its laundry room. With its level backyard and great size deck, you will enjoy your

    Anita S. Cristiano HomeSmart Homes & Estates

    77 Prince St, Middletown, NY 10940
  • /5

    $280,000

    • 4 Beds
    • 3 Baths
    • 1,374 Sq Ft

    22 Bonnell St, Middletown, NY 10940

    Welcome to 22 Bonnell St, a charming 4-bedroom, 3-bathroom home situated on a desirable corner lot on a quiet street in the heart of Middletown, NY. This spacious residence is brimming with potential, offering a unique opportunity to customize and create your dream home exactly the way you envision it. While the home could benefit from some updating, its solid foundation and prime location make

    Emmett McDowell Keller Williams Rlty Integrity

    22 Bonnell St, Middletown, NY 10940
  • /22

    $249,900

    • 2 Beds
    • 1 Bath
    • 820 Sq Ft

    58 Wawayanda Ave, Middletown, NY 10940

    A Great Place to Call Home or perfect for those looking to expand your real estate investment portfolio, this charming Middletown home offers the perfect blend of comfort, convenience, and value. Cozy yet spacious, this home has been thoughtfully updated and is truly move-in ready! With 2 bedrooms, a home office which offers much potential for additional space and a full bath you will have all

    Frank Muccari Cronin & Company Real Estate

    58 Wawayanda Ave, 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

    $429,999

    • 6 Beds
    • 2 Baths
    • 1,878 Sq Ft

    19 Wawayanda Ave, Middletown, NY 10940

    Price reduced....... A Must see... Fully available opportunity knocks to own this colonial home, located in the heart of the Hudson Valley. Entering this home with a long foyer that leads into a living room, spacious dining room with plenty of natural light, eat in kitchen, Kitchen is updated with lots of cabinet space front deck, back porch, new flooring for the entire house. New roof,

    Samar Tarazi Keller Williams Realty

    19 Wawayanda Ave, Middletown, NY 10940
  • /18

    $565,000

    • 3 Beds
    • 2 Baths
    • 2,321 Sq Ft

    3 Parkview Dr, Middletown, NY 10940

    Welcome to your next chapter—this 3-bedroom, 2-bathroom home offers both comfort and convenience. Nestled in a peaceful Middletown neighborhood, this home keeps you connected to everything that matters. Spend weekends at nearby Watts Memorial and Fancher-Davidge Parks, both just a short distance away. Schools like Northern Academy and those in the Middletown City School District are also

    Kevin Sanabria eRealty Advisors, Inc

    3 Parkview Dr, Middletown, NY 10940
  • /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
  • /22

    $325,000

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    24 Crescent Place, Middletown, NY 10940

    Attention all investors and home buyers! Look no further, This amazing colonial is in great condition, Features 3 Bedrooms 1 full bathroom, New hot water tank and more... Driveway and garage to accommodate parking and storage, Home is well maintained and move in ready! Great location in town of Middletown and a 90 min drive to NYC! Priced to sell and wont last! Reach out today for your private

    Shlome Weber Q Home Sales

    24 Crescent Place, Middletown, NY 10940
  • /24

    $329,900

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

    9 Fairview Ave, Middletown, NY 10940

    A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

    Anita S. Cristiano HomeSmart Homes & Estates

    9 Fairview Ave, 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
  • /2

    $525,000

    • 5 Beds
    • 4 Baths
    • 3,140 Sq Ft

    7 Highland View Place, Middletown, NY 10940

    Welcome home to this beautifully maintained 5-bedroom, 4-bathroom raised ranch, ideally situated near the highly-rated Presidential Park Elementary School in Middletown, NY. Perfect for growing families or multi-generational living, this expansive home offers generous living space, natural light throughout, and thoughtful updates that make it move-in ready.Step inside to discover an open-concept

    Hilary Hemans-Mensah Keller Williams Realty

    7 Highland View Place, Middletown, NY 10940
  • /18

    $595,000

    • 8 Beds
    • 3 Baths
    • 3,000 Sq Ft

    21-23 Highland Ave, Middletown, NY 10940

    Kathleen Christopherson EXCLUSIVE SALES AND RENTALS

    21-23 Highland Ave, Middletown, NY 10940
  • /29

    $319,000 Open Sat 10AM - 1PM

    • 3 Beds
    • 1 Bath
    • 1,124 Sq Ft

    82 Houston Ave, Middletown, NY 10940

    Tucked on a dead-end street, this updated 3-bedroom, 1-bath home offers a welcoming blend of character and modern comfort. The cozy living room sets the tone - perfect for everyday living and casual entertaining. A traditional layout flows into a dedicated dining area and an updated kitchen with direct access to a private outdoor space this is ideal for year-round grilling and low-maintenance

    Wendy Beck Krumpfer Realty Group, LLC

    82 Houston Ave, Middletown, NY 10940
  • /33

    $319,000

    • 3 Beds
    • 1 Bath
    • 1,136 Sq Ft

    127 Watkins Ave Unit 129, Middletown, NY 10940

    Welcome to 127 Watkins Ave! This charming single-family home offers great bones and endless potential with just a few cosmetic touches. Featuring 3 bedrooms, 1 full bath, and a finished attic that can easily serve as an additional bedroom, home office, playroom, or flex space, this home provides plenty of room to grow. Inside, you’ll find beautiful hardwood floors in excellent condition and a

    Waldina Almazan RE/MAX Benchmark Realty Group

    127 Watkins Ave Unit 129, Middletown, NY 10940
  • /23

    $224,900

    • 3 Beds
    • 1 Bath
    • 1,032 Sq Ft

    80 Beattie Ave, Middletown, NY 10940

    Here on freshly paved Beattie Ave in Middletown, you'll find this 1920 two story style. The home has three bedrooms, a full bath, kitchen, living room- dining room combo, as well as a walk-up attic and full unfinished basement. Outside there is a covered front porch, small fenced yard and a detached two car garage. The home is in overall sound condition, but will need enough repairs that it may

    Keith Sumner John J Lease REALTORS Inc

    80 Beattie Ave, Middletown, NY 10940
  • /2

    $199,000

    • 3 Beds
    • 1 Bath
    • 1,040 Sq Ft

    36 Mountain Ave Unit 34, Middletown, NY 10940

    This is a short sale Property being sold as is. This property has plenty of potential. A double sized lot. You can bring your hammers and fix up the property or knock down and build your dream home. Hurry before its gone.

    Arduino Colomban Skyler Realty LLC

    36 Mountain Ave Unit 34, Middletown, NY 10940

Why Live in Middletown

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$341,000
Median Single Family Sale Price
$370,000
Median Townhouse Sale Price
$350,000
Median 2 Bedroom Sale Price
$260,000
Median 1 Bedroom Sale Price
$169,000
Average Price Per Sq Ft
$238
Number of Homes for Sale
48
Last 12 months Home Sales
205
Months of Supply
2.80
Median List Price
$348,800
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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