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Middletown, NY 2-Story Homes for Sale

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  • /25

    $420,000

    • 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
  • /24

    $380,000

    • 3 Beds
    • 2.5 Baths
    • 1,593 Sq Ft

    568 County Route 49 Unit 2C, Middletown, NY 10940

    For investors or anyone interested in taking on tenants until 9/30/26 and at that time can take possession of the unit. Tenants have a lease expiration date of 9/30/26 and must remain there until that time. Tenants pay $2850 a month and pay for oil and electric. They are excellent tenants. New townhouse on right side (Unit 2C) available in the Minisink Valley School District. This home

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 328-4272

    568 County Route 49 Unit 2C, 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.

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    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 299-0839

    13 Smith St, Middletown, NY 10940
  • /50

    $889,000

    • 4 Beds
    • 2.5 Baths
    • 3,437 Sq Ft

    3 Kings Dr, Middletown, NY 10941

    Luxury Living in Hamptonburgh. Nestled in the prestigious Windsor Estates enclave, within the sought-after Goshen School District, this exceptional Contemporary residence offers a rare blend of elegance, comfort, and convenience. With nearly 3,500 sqft of thoughtfully designed living space, this striking home features 4 spacious bedrooms, 3 bathrooms, and a 3-car garage. Step into a grand

    Agent Photo

    Christina Rowan

    Howard Hanna Rand Realty

    (845) 393-3879

    3 Kings Dr, Middletown, NY 10941
  • /40

    $725,000

    • 5 Beds
    • 3.5 Baths
    • 3,358 Sq Ft

    339 Kirbytown Rd, Middletown, NY 10940

    Nestled gracefully amidst more than thirteen acres of lush, undisturbed countryside, this remarkable colonial-style residence stands as a testament to elegance, comfort, and thoughtful practicality. A rare offering in today’s market, the property invites you to experience the best of both worlds: resplendent rural seclusion and immediate access to the conveniences of modern life. Conceived as a

    Annie Hansen Howard Hanna Rand Realty

    339 Kirbytown 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
  • /32

    $539,000

    • 3 Beds
    • 2.5 Baths
    • 2,994 Sq Ft

    43 Last Rd, Middletown, NY 10941

    Stunning large ranch zoned 215 - 1 Family Res w/Apt, many updates set up for extended family...two kitchens! Come see this beautifully maintained home features master bedroom with bath, walking closet, sunken living room, large open kitchen featuring dining area with sliding door to huge deck overlooking a fenced in level yard and shed. This cedar sided home has been meticulously maintained,

    Mary Jo Coleman Curasi Realty, Inc.

    43 Last Rd, Middletown, NY 10941
  • /36

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 1,825 Sq Ft

    708 Kirbytown Rd, Middletown, NY 10940

    Such a peaceful setting for this immaculate 4 BR, 2.5 bath Colonial in the heart of The Minisink School District. This home is a dream for pet owners! The fenced backyard keeps your pets safe and secure while they play, and the underground dog fence lets them roam worry-free. There is a woodstove that is perfect for chilly evenings that will help with your heating costs during the cold winter

    Debbie Walsh SHAHAR Management LLC

    708 Kirbytown Rd, 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
  • /25

    $579,000

    • 3 Beds
    • 2.5 Baths
    • 2,205 Sq Ft

    30 Daly Rd, Middletown, NY 10940

    New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft

    Jonathon Lee Keller Williams Hudson Valley

    30 Daly Rd, Middletown, NY 10940
  • /36

    $825,000

    • 5 Beds
    • 3.5 Baths
    • 3,700 Sq Ft

    104 Elise Dr, Middletown, NY 10941

    LAST HOME AVAILABLE! Welcome to The Woodlands at Scotchtown Estates! This exquisite picturesque community sits in the highly sought after Valley Central SD, featuring luxury and convenience at your fingertips. Custom built colonials lead the way as you drive down the beautiful tree lined road of this development. This expansive colonial now complete and ready to welcome it's new owners! The main

    Juan Bautista Keller Williams Realty

    104 Elise Dr, Middletown, NY 10941
  • /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
  • /25

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,536 Sq Ft

    208 Grahamtown Rd, Middletown, NY 10940

    PRICE REDUCTION! Welcome to 208 Grahamtown Rd, this charming estate spanning 54+ acres is a nature lover's paradise with abundance in wildlife and mature trees offering immense potential and breathtaking views. The home features beautiful hardwood floors, a wood burning stove, 4 over-sized bedrooms, 2 full bathrooms, 1st floor office/den, multiple outbuildings, and 1 car attached garage. Whether

    Steven Cabrera Resort Realty

    208 Grahamtown Rd, Middletown, NY 10940
  • /30

    $399,999

    • 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
  • /27

    $295,000

    • 3 Beds
    • 1.5 Baths
    • 1,400 Sq Ft

    105 Sheffield Dr, Middletown, NY 10940

    Town of Wallkill Townhouse - Low Taxes - Great InvestmentThis charming 3-bedroom, 1.5-bath home is your perfect mix of space, location, and value. Nestled on a generous lot with a large yard, there's plenty of room for play, gardening, or entertaining under the stars. Step out from your primary bedroom onto a balcony—the ideal spot for morning coffee or winding down with a book while

    Cindy-Lee Dorcely Keller Williams Hudson Valley

    105 Sheffield Dr, Middletown, NY 10940
  • /31

    $480,000

    • 3 Beds
    • 2 Baths
    • 1,222 Sq Ft

    295 Lybolt Rd, Middletown, NY 10941

    Spacious home with large yard on a quiet street - what more could you want? This beautiful contemporary home has had many upgrades over the last few years! The main level features an open kitchen, dining room and living room with partial wrap around deck - perfect for entertaining or just extended living space. Three large bedrooms and two full bathrooms complete the upper level. Downstairs

    Britanni Gaucher Keller Williams Realty

    295 Lybolt Rd, Middletown, NY 10941
  • /17

    $309,900

    • 2 Beds
    • 2.5 Baths
    • 1,348 Sq Ft

    71 Jordan Ln, Middletown, NY 10940

    Welcome to this sought-after 2-bedroom, 2.5-bath townhouse in Mountainside Hills Condominium. The main level has hardwood floors, a kitchen dining area, a spacious living room with access to your private deck, a powder room, and an in-unit laundry room. Upstairs, you'll find the primary bedroom with an ensuite bathroom and walk-in closet, plus an additional bedroom and a full bath. The home also

    Jonathon Lee Keller Williams Hudson Valley

    71 Jordan Ln, Middletown, NY 10940
  • /34

    $395,000

    • 2 Beds
    • 2.5 Baths
    • 1,677 Sq Ft

    28 Pinto Rd W, Middletown, NY 10941

    Welcome to this stunning, better-than-new townhome located in the highly sought-after community of Liberty Commons. Just one year young, this impeccably maintained residence offers the perfect blend of modern luxury, comfort, and convenience. Step inside to discover a light-filled open layout featuring gleaming hardwood floors on the main level and plush carpeting upstairs. The designer kitchen

    Juan Bautista Keller Williams Realty

    28 Pinto Rd W, Middletown, NY 10941
  • /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
  • /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
  • /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
  • /6

    $320,000

    • 3 Beds
    • 2 Baths
    • 1,964 Sq Ft

    115 Vincent Dr, Middletown, NY 10940

    Check out 115 Vincent Drive, a unique split ranch in Middletown, NY. It’s close to everything on Route 211, so shopping, dining, and everyday errands are minutes away. The fenced backyard is great for pets or outdoor hangouts, and the two-car garage gives you plenty of parking and storage space.

    Christian Baez Keller Williams Hudson Valley

    115 Vincent 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
  • /36

    $999,900

    • 5 Beds
    • 4.5 Baths
    • 4,200 Sq Ft

    255 Howells Rd, Middletown, NY 10940

    Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom home spanning 4,200 square feet, complete with a large barn and a natural pond, all set on 36.8 acres. This private estate is located in Middletown, NY, nestled among rolling pastures, tranquil woods, and your very own pond. The expansive property also features a two-story post-and-beam barn with horse

    Jonathon Lee Keller Williams Hudson Valley

    255 Howells Rd, Middletown, NY 10940
  • /34

    $318,999

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

    15 Silo Ln, Middletown, NY 10940

    Back on Market! Buyer couldn't get finanacing! 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

    Pedro Garcia Curasi Realty, Inc.

    15 Silo Ln, 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
  • /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
  • /35

    $699,000

    • 4 Beds
    • 3.5 Baths
    • 3,432 Sq Ft

    200 Mt Orange Rd, Middletown, NY 10940

    Welcome to this most charming 1870's farmhouse situated on idyllic 6.4 level pastoral acres with small pond. This property boasts wide moldings and other intricate detailing that showcase the exceptional craftmanship that went into its construction. Enjoy both gorgeous sunrises and sunsets from almost any room. This home has been well maintained, with some newer additions, such as the family

    Joe Distelburger Keller Williams Realty

    200 Mt Orange Rd, Middletown, NY 10940
  • /3

    $349,000 Coming Soon

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft

    6 Perrins Mews, Middletown, NY 10940

    Welcome to this charming 3-bedroom, 2.5-bathroom townhome in the highly sought-after community of Canterbury Knolls. This home is truly move-in ready, offering a perfect blend of comfort and convenience.The main living areas are bright and inviting, and you'll find elegant hardwood flooring throughout the staircase, hallway, and all three bedrooms. A sliding door in the dining area opens

    Maureen Cronin Cronin & Company Real Estate

    6 Perrins Mews, Middletown, NY 10940
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