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Middletown Houses for Sale

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  • /25

    $450,000

    • 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
  • /2

    $250,000

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    13 Smith St, Middletown, NY 10940

    Looking to add a rental property to your porfolio? This 3 bedroom, 1 bathroom home might be the one. Long term tenant looking to stay. Located in the heart of the city of Middletown. Walking distance to local shops, restaurants, supermarket, park and much more. Located on a one way street with low local traffic. Call today for appoiintment.

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 299-0839

    13 Smith St, 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
  • /27

    $429,000

    • 3 Beds
    • 2.5 Baths
    • 2,223 Sq Ft

    104 Monhagen Ave, Middletown, NY 10940

    Step into timeless charm with this beautifully renovated Victorian-style home! This bright and sunny 3-bedroom, 2.5-bath residence has been thoughtfully updated while maintaining its classic character. Gleaming hardwood floors flow throughout, and the inviting wrap-around porch offers the perfect spot for morning coffee or evening relaxation. Inside, you’ll find an open and airy layout with

    Jeffrey Hozias Howard Hanna Rand Realty

    104 Monhagen Ave, Middletown, NY 10940
  • /39

    $415,789

    • 5 Beds
    • 2 Baths
    • 1,920 Sq Ft

    15 Rowan St Unit 13, Middletown, NY 10940

    Discover the perfect blend of comfort and charm in this beautifully updated home, nestled on a coveted double corner lot. Surrounded by lush hedges and offering ample parking, this residence welcomes you with curb appeal and room to spare. Inside, you'll find five spacious bedrooms, including a convenient first-floor bedroom, ideal for guests or flexible living needs. The home boasts two full

    Juan Bautista Keller Williams Realty

    15 Rowan St Unit 13, Middletown, NY 10940
  • /35

    $489,000

    • 3 Beds
    • 2 Baths
    • 1,823 Sq Ft

    30 Wilson St, Middletown, NY 10940

    MAGAZINE READY!!!! HGTV CALLED, YOUR DREAM HOME JUST HIT THE MARKET! Absolutely Stunning Newly Renovated Raised Ranch in Middletown! Prepare to be impressed by this incredible, newly renovated raised ranch, ideally situated in a quiet and peaceful Middletown neighborhood. Thoughtfully redesigned with impeccable taste and high end, on-trend finishes, this home offers both style and substance in

    Frank Muccari Cronin & Company Real Estate

    30 Wilson St, 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
  • /30

    $449,900

    • 3 Beds
    • 2.5 Baths
    • 1,987 Sq Ft

    7 Roosevelt Ave, Middletown, NY 10940

    Welcome to this charming ranch-style home located on a desirable corner lot in the city of Middletown. Spanning just under 2,000 square feet, this inviting residence features spacious rooms throughout. As you enter, you'll be greeted by custom woodwork and elegant wainscoting that add a touch of sophistication throughout this home. The layout is accentuated by tile flooring that flows seamlessly

    Patricia Sassi RE/MAX Benchmark Realty Group

    7 Roosevelt Ave, Middletown, NY 10940
  • /33

    $375,000

    • 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

    Claudia Lepore Keller Williams Realty

    7 Forest Ave, Middletown, NY 10940
  • /29

    $375,000

    • 3 Beds
    • 1 Bath
    • 1,922 Sq Ft

    7 Wilbur Ave, Middletown, NY 10940

    Welcome to this charming 3 bedroom, 2 bath home located in the heart of Middletown, NY. Perfect starter home or are you an investor looking to rent? Upon entering you get a sense of historic Middletown, NY and even more majestic when you see the views. Offers large rooms, hardwood floors, full walk up attic, and a large unfinished/walkout basement. Nestled in a vibrant community, this property

    John Bilancione Nicoli Realty

    7 Wilbur Ave, Middletown, NY 10940
  • /26

    $430,000

    • 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
  • /30

    $399,999 Coming Soon

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

    5 Mills Ave, Middletown, NY 10940

    MOVE-IN READY IN MIDDLETOWN!!!Discover this well-maintained 3-bedroom, 1.5-bathroom Two story style home, ideally located on a quiet street in the heart of Middletown and within the Middletown School District. Enjoy easy access to local shops, restaurants, parks, and major highways like Route 17 and I-84—perfect for commuters and families alike. Step inside to a bright and comfortable living

    Richard Baxter Keller Williams Realty

    5 Mills Ave, 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
  • /49

    $370,000

    • 3 Beds
    • 1.5 Baths
    • 1,680 Sq Ft

    112 Monhagen Ave, Middletown, NY 10940

    SO MUCH ROOM, SO MUCH CHARM—AND YES, YOUR GUESTS WILL BE IMPRESSED.Step into a home that instantly makes you say, 'Wow!' Bursting with sunlight, original character, and modern comfort, this spacious beauty is designed for both everyday living and unforgettable entertaining. Whether you’re hosting a dinner party, game night, or just need room for everyone to spread out—you’ll find it

    Katheryn DeClerck Howard Hanna Rand Realty

    112 Monhagen Ave, 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
  • /29

    $349,750

    • 2 Beds
    • 1 Bath
    • 1,324 Sq Ft

    9 Grandview Ave, Middletown, NY 10940

    Step inside this Middletown ranch home and be pleasantly surprised by the spacious layout, updated features, and inviting vibe that make this home a true gem. With newer windows, kitchen appliances, and central air conditioning, comfort and convenience are already checked off your list. The cute breezeway connecting the garage to the house adds a fun bonus space—think sunny sitting area or

    Patricia Sassi RE/MAX Benchmark Realty Group

    9 Grandview Ave, Middletown, NY 10940
  • /28

    $330,000

    • 3 Beds
    • 1 Bath
    • 1,263 Sq Ft

    11 1/2 Dolson Ave, Middletown, NY 10940

    Back on the Market — Buyer’s Opportunity!This move-in-ready and renovated 3-bedroom Cape Cod in the heart of Middletown combines classic charm with modern updates. Step into a bright, spacious layout featuring a sun-filled living room, formal dining area, and a beautifully updated kitchen — ideal for both daily living and entertaining.The walk-out basement offers generous storage, a

    Robert Siracuse Absolute Real Estate of NY Inc

    11 1/2 Dolson Ave, Middletown, NY 10940
  • /41

    $315,000

    • 3 Beds
    • 1 Bath
    • 850 Sq Ft

    16 Madelaine Terrace, Middletown, NY 10940

    Charming and efficient, this 850 sq ft ranch in Middletown, NY offers the perfect blend of comfort and potential. Featuring 3 cozy bedrooms, 1 full bath, and a full unfinished basement ready for your vision—whether it’s extra living space, a rec room, or storage galore. The generous backyard provides plenty of space for entertaining, gardening, or simply relaxing in your own private outdoor

    Kewin Garabito eXp Realty

    16 Madelaine Terrace, Middletown, NY 10940
  • /16

    $355,000

    • 4 Beds
    • 2 Baths
    • 1,486 Sq Ft

    184 Highland Ave, Middletown, NY 10940

    Here you have a beautiful Victorian style home, centrally located in Middletown NY. This home features a beautiful wrap around porch that presents a charming appeal to all visitors of the property. The property has been upgraded by the current owner, they have put in $55k of upgrades which include an updated kitchen, new central air system, new doors, and new windows! The home encompasses 4

    Jorge Lugo Real Broker NY LLC

    184 Highland 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
  • /45

    $353,000

    • 3 Beds
    • 1.5 Baths
    • 1,564 Sq Ft

    38 Wilson St, Middletown, NY 10940

    Welcome to 38 Wilson where charm, space, and potential come together.This 3-bedroom, 1.5-bath split-level home offers a fresh start with newly painted interiors and a layout full of possibility. Step inside to soaring cathedral ceilings and a bright open-concept kitchen, perfect for both everyday living and entertaining. Upstairs features three generously sized bedrooms and a full bathroom.

    Pete Koutros Keller Williams Hudson Valley

    38 Wilson St, 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
  • /13

    $350,000

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

    3 Chappell Pkwy, Middletown, NY 10940

    A lovely single family Ranch home locates at a dead end street in a quiet neighborhood of Middletown. This single family home offers 2 bedrooms and a full bathroom, a large eat in kitchen, dining area and spacious living room and a big sun room. The backyard is fully fenced in with a shed. Plenty of storage space in the basement and an 1 car indoor garage. Great location, close to YMCA,

    Feng Chang Acer Realty Inc

    3 Chappell Pkwy, Middletown, NY 10940
  • /27

    $369,000

    • 3 Beds
    • 1 Bath
    • 1,144 Sq Ft

    53 Richmond Place, Middletown, NY 10940

    Settle into the charm of Orange County, NY, in this bright and airy three-bedroom home. The kitchen features elegant white cabinets and stainless steel appliances, perfectly combining style and functionality. Additional conveniences include a laundry room, mudroom, walk-up attic, and a full basement for ample storage. Situated on a corner lot, this property boasts a fenced-in backyard with plenty

    Kelly Roebuck Curasi Realty, Inc.

    53 Richmond Place, 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
  • /20

    $325,000

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

    317 Wawayanda Ave, Middletown, NY 10940

    Charming 4-Bedroom Home with Cozy Curb Appeal - A Must See!Welcome to this delightful 4-bedroom, 1-bath single-family home, perfectly nestled in a peaceful, tree-lined neighborhood. With its eye-catching red exterior and classic white trim, this home offers curb appeal that is both inviting and timeless.Step inside to discover a warm, sunlit living space ideal for family

    Pete Wolven Hudson Valley Home Connection

    317 Wawayanda Ave, 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
  • /15

    $339,900

    • 3 Beds
    • 1 Bath
    • 1,278 Sq Ft

    39 Crescent Place, Middletown, NY 10940

    Very Beautifully renovated home on a quiet street in Middletown. Perfect location close to schools, shopping, and playgrounds. Clean hardwood floors, updated kitchen, newly paved driveway, finished patio, and plenty of natural light. In addition, all windows were replaced in 2020

    Zhiheng Tang Keller Williams Hudson Valley

    39 Crescent Place, Middletown, NY 10940
  • /49

    $660,000

    • 8 Beds
    • 5 Baths
    • 5,533 Sq Ft

    203 Highland Ave, Middletown, NY 10940

    Welcome to this exceptional mother/daughter residence, where comfort seamlessly intertwines with practicality! This expansive colonial home is meticulously crafted to accommodate the diverse needs of everyone. This unique property offers two homes in one, that connect within the interior of the home— both equipped with their own front and side entrances! Yes, you read that right, this home offers

    Patricia Sassi RE/MAX Benchmark Realty Group

    203 Highland Ave, 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
  • /10

    $369,900

    • 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 Oxford Property Group USA

    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
  • /23

    $259,900

    • 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

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