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Middletown, NY 2-Story Homes for Sale

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  • /15

    $279,900

    • 2 Beds
    • 1 Bath
    • 1,201 Sq Ft

    122 Cottage St, Middletown, NY 10940

    Your First Single-Family Home—Where Independence Begins | Middletown, NYThere’s a moment when you realize: it’s time to stop paying someone else’s mortgage and start building something of your own. This 2-bedroom, 1-bath single-family home in Middletown, NY is that moment in the making—a chance to own land, space, and freedom, with no shared walls or noisy neighbors above or below you. Just you,

    Agent Photo

    Brian Caplicki

    Keller Williams Hudson Valley

    (845) 378-9670

    122 Cottage St, Middletown, NY 10940
  • /2

    $275,000

    • 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
  • /50

    $899,000

    • 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

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    Christina Rowan

    Howard Hanna Rand Realty

    (845) 393-3879

    3 Kings Dr, Middletown, NY 10941
  • /27

    $259,900

    • 2 Beds
    • 1.5 Baths
    • 1,082 Sq Ft

    34 Jimal Dr, Middletown, NY 10940

    Beautifully cared and maintained 2 bedrooms, 1.5 bathrooms townhouhse in the desirable Highland Park Village. From the moment you walk through the door you can see the pride and care the sellers have provided to this unit. Not one thing for you to do, except bring your personal stuff. Laminate floors throughout. Upgraded kitched with stainless steel appliances. Spacious primary bedroom offers 2

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (845) 478-8249

    34 Jimal Dr, Middletown, NY 10940
  • /24

    $399,900

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

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

    FOR INVESTORS ONLY.... New townhouse on right side (Unit 2C) available in the Minisink Valley School District. This home welcomes you to an open foyer that leads to an updated kitchen with Quartz/Quartzite countertops and ample white cabinets. Lots of sunshine enters this home. The dining and living room area is spacious with beautiful floors. Huge closet that can be used as a pantry. A deck to

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 681-1992

    568 County Route 49 Unit 2C, Middletown, NY 10940
  • /7

    $239,888

    • 2 Beds
    • 1.5 Baths
    • 924 Sq Ft

    218 Concord Ln, Middletown, NY 10940

    Welcome to this charming first-floor condo located in Buttonwood Hills community! With 2 bedrooms, 2 baths, and a patio, this well-maintained unit offers a galley kitchen, dining area, and living room. Enjoy access to clubhouse amenities and a community poolhouse. Ideal for those seeking convenience and community living. InteriorFeatures: Built-in Features,

    Agent Photo

    John Olivero

    Keller Williams Realty

    (845) 475-0808

    218 Concord Ln, Middletown, NY 10940
  • /39

    $624,999 Open Sun 11AM - 1PM

    • 4 Beds
    • 4.5 Baths
    • 2,888 Sq Ft

    594 County Route 22, Middletown, NY 10940

    MINISINK SCHOOLS - WORK FROM HOME AND HAVE ROOM FOR EXTENDED FAMILY - Nestled at the end of a long driveway is this spacious four-bedroom, five-bathroom home situated on just under four spacious acres. It is absolutely perfect for multi-generational living, offering a separate in-law suite with a kitchenette and bathroom. This home features not one, but TWO primary suites, one located on the

    Courtney Popowick Rita Levine Real Estate

    594 County Route 22, Middletown, NY 10940
  • /43

    $589,900

    • 4 Beds
    • 3 Baths
    • 2,916 Sq Ft

    8 Red Oak Ct, Middletown, NY 10941

    Welcome to this beautifully maintained colonial home, situated in the Pine Bush School District. With just under 3,000 square feet of thoughtfully designed living space, this recently renovated home offers comfort, style, and flexibility for modern living. Inside, you’ll find four spacious bedrooms, plus a versatile bonus room on the main level—perfect for a guest room, home office, or cozy den.

    Joana Mojica RE/MAX Benchmark Realty Group

    8 Red Oak Ct, Middletown, NY 10941
  • /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

    $589,900

    • 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
  • /26

    $529,900

    • 4 Beds
    • 3 Baths
    • 2,242 Sq Ft

    26 Davidge Rd, Middletown, NY 10940

    Spectacular Contemporary Home Located in Prestigious Presidential Heights in the City of Middletown. This Magnificent Home Features a Bright Airy, Sundrenched Floor plan. Gorgeous Marble Flooring, Large Sunken Living Room, Beautiful Sunken Family Room Custom 2 Sided Fireplace. Gourmet Kitchen with a designer Kitchen cabinetry, Stainless Steel Appliances, Subway tiled Backsplash , Recessed

    John Biasi Howard Hanna Rand Realty

    26 Davidge Rd, Middletown, NY 10940
  • /27

    $599,999

    • 4 Beds
    • 2.5 Baths
    • 3,387 Sq Ft

    48 James Clark Dr, Middletown, NY 10940

    This distinguished Colonial-style beauty is nestled in a tranquil neighborhood, offering a peaceful retreat while remaining conveniently accessible to local amenities, the coveted Pine Bush School District, and major roadways—making it an ideal place to call home. Spanning a generous 3,387 square feet on a 1.6-acre lot, this residence seamlessly blends classic design with modern comforts,

    Annette Exposito eXp Realty

    48 James Clark Dr, Middletown, NY 10940
  • /33

    $425,000

    • 3 Beds
    • 1 Bath
    • 1,316 Sq Ft

    22 Witte Dr, Middletown, NY 10940

    Welcome to 22 Witte Drive—a well-maintained 3-bedroom, 1-bath home located in a peaceful, sought-after neighborhood within the Minisink Valley School District. This charming property features a beautifully renovated kitchen (2020) with quartz countertops and GE appliances, pristine Andersen windows that fill the home with natural light, and hardwood floors beneath the carpet. The finished

    Nina Piacente Julia B Fee Sothebys Int. Rlty

    22 Witte Dr, Middletown, NY 10940
  • /22

    $359,900

    • 4 Beds
    • 3 Baths
    • 1,505 Sq Ft

    8 Ebury Mews, Middletown, NY 10940

    Spacious 4-Bedroom Home in Desirable Canterbury Knolls – Town of WallkillWelcome to easy, carefree living in the sought-after Canterbury Knolls community! This beautifully maintained and rare 4-bedroom, 3-bathroom single-family detached home is one of the largest in the neighborhood and offers both space and privacy—perfectly situated at the end of a quiet cul-de-sac, adjacent to peaceful

    Jonathon Lee Keller Williams Hudson Valley

    8 Ebury Mews, Middletown, NY 10940
  • /25

    $289,000

    • 2 Beds
    • 1.5 Baths
    • 1,185 Sq Ft

    12 Durham Ct, Middletown, NY 10940

    "Waters Edge" now offers this spacious 2bdrm/1.5 bath for you to OWN! A well manicured unit with great bones and potential that you can convert into a master piece. Enter into an open floor plan from dining room to living room with sliders that lead to an outdoor patio where you can sip on morning coffee while enjoying the out doors. A spacious eat-in kitchen with window access to dining area

    Sandra Arnez Keller Williams Hudson Valley

    12 Durham Ct, Middletown, NY 10940
  • /33

    $289,900

    • 3 Beds
    • 2 Baths
    • 1,631 Sq Ft

    42 Wisner Ave, Middletown, NY 10940

    A charming 3-bedroom, 2-bathroom home situated on a spacious corner lot in the heart of Middletown. This well-maintained property offers solid bones and endless potential for your personal touch. The first floor features a flexible layout, including a cozy den that could easily serve as a 4th bedroom, home office, or guest space. Ample natural light, and a traditional floor plan create a warm and

    Kismet Johnson eXp Realty

    42 Wisner Ave, Middletown, NY 10940
  • /6

    $159,800

    • 1 Bed
    • 1 Bath
    • 740 Sq Ft

    228 Concord Ln Unit 228, Middletown, NY 10940

    Move-in ready, 1-bedroom, 1-bathroom second-floor unit in Middletown, NY. Ideal for investors or first-time buyers seeking convenience and community living. Commuter-friendly location close to all highways, colleges, shopping, restaurants, and public transportation. Enjoy access to clubhouse amenities and a community pool. HOA includes water, snow removal, garbage, pool and common ground

    Yasmine Delgado BHG Real Estate Green Team

    228 Concord Ln Unit 228, Middletown, NY 10940
  • /29

    $380,000

    • 3 Beds
    • 1.5 Baths
    • 1,788 Sq Ft

    14 W Prospect Ave, Middletown, NY 10940

    One among a neighborhood of classic Tudor homes. This one can be yours! Located on a lovely street close to Touro College. This home is a treasure of original features such as hardwood floors, french doors, a sunroom and even a secret room off the walk in closet that can easily be a nursery, office, exercise room, or artist studio. What else? How about a brick fireplace and a first floor bedroom?

    Sharon Reynolds Keller Williams Hudson Valley

    14 W Prospect Ave, Middletown, NY 10940
  • /30

    $249,000

    • 2 Beds
    • 2 Baths
    • 1,049 Sq Ft

    189 Ruth Ct, Middletown, NY 10940

    Discover comfort, space, and convenience in this beautifully designed 2-story condo, ideally located in a sought-after community, with easy access to major highways and shopping centers. From the moment you step inside, you'll be welcomed by soaring vaulted ceilings and an abundance of natural light that fills the open living area, creating a warm and inviting atmosphere. The Kitchen offers a

    Rosalie Cook Weichert Realtors

    189 Ruth Ct, Middletown, NY 10940
  • /21

    $355,000

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

    5 Fitzherbert Mews, Middletown, NY 10940

    Newly updated 3 bedroom, 2.1 bath Contemporary style located in Canterbury Knolls is waiting for you to call it home. It features a great open floor plan/ primary bedroom ensuite, all bedrooms are nicely sized. gas fireplace in the living room, air, dining room, laundry room. Close to major highways, shopping and amenities. 1 Car attached garage and driveway parking.

    Rita White Keller Williams Realty Partner

    5 Fitzherbert Mews, Middletown, NY 10940
  • /49

    $950,000

    • 4 Beds
    • 3.5 Baths
    • 3,517 Sq Ft

    26 Erin Ct, Middletown, NY 10941

    Every King or Queen needs a castle and this majestic colonial reigns supreme! Perched high on 2.6 acres in a private, executive subdivision in the Crawford countryside within the Pine Bush School District, this home is a true crown jewel. Set against the natural beauty of a 150-acre evergreen farm, the setting alone makes this 4-bedroom, 3.5-bath home something truly special—but the charm goes

    Virginia Corbett eXp Realty

    26 Erin Ct, Middletown, NY 10941
  • /15

    $425,000

    • 6 Beds
    • 2 Baths
    • 2,748 Sq Ft

    225 Highland Ave, Middletown, NY 10940

    Great Opportunity For Future Owner Occupant Or An Investor Who Is Looking To Collect $4,450 Of Current Rental Income With Tenants In Place.Fully Renovated In 2020. The Property Was Originally A 2 Family And Has Two Levels, Basement And A Full Attic. 2 Forced Hot Air Systems With Separate Gas And Electric Services. Both Sides Are Set With First Floor Kitchen With Door To Deck On Rear. Living Room

    Mark Karten Karten Real Estate Svcs LLC

    225 Highland Ave, Middletown, NY 10940
  • /37

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,406 Sq Ft

    21 Wilkin Ave, Middletown, NY 10940

    Welcome to this charming 3-bedroom, 2-bathroom home nestled in the heart of Middletown, NY! This beautifully maintained property is in excellent condition, featuring a blend of classic charm and modern convenience. The spacious layout offers comfortable living with a formal dining room, perfect for family meals and entertaining guests.As you step inside, you'll immediately notice the pristine

    Ben Schubert Richmont Realty

    21 Wilkin 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
  • /15

    $145,000

    • 1 Bed
    • 1 Bath
    • 752 Sq Ft

    318 Ruth Ct, Middletown, NY 10940

    Welcome to this charming one-bedroom, one-bath condo located in the Eagles Point/Eastview Condominium community. This property is eagerly awaiting a new buyer to infuse it with fresh energy and personal style. The open floor plan seamlessly connects the living room to the dining area, making it perfect for entertaining guests. With a little creativity and vision, this condo can be transformed

    Patricia Sassi RE/MAX Benchmark Realty Group

    318 Ruth Ct, Middletown, NY 10940
  • /49

    $749,900

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

    203 Highland Ave, Middletown, NY 10940

    Welcome to this exceptional multigenerational residence, where comfort seamlessly intertwines with practicality! This expansive colonial home is meticulously crafted to accommodate the diverse needs of every generation. 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

    Patricia Sassi RE/MAX Benchmark Realty Group

    203 Highland Ave, 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
  • /36

    $850,000

    • 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
  • /18

    $319,000

    • 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
  • /21

    $204,000

    • 2 Beds
    • 1 Bath
    • 1,000 Sq Ft

    78 Austin St, Middletown, NY 12093

    First time offered! My Blue Heaven! A hidden gem nestled at the end of a quiet lane in sophisticated Margaretville and connected to all Village services. The charming 2 bd cottage needs your touch to bring it to life. The secluded and conveniently located oversized parcel abuts Bull Run stream yet is not in the flood zone. The property boasts a one car garage which could house a studio. The

    Lorraine Takahashi Listing by Howard Hanna

    78 Austin St, Middletown, NY 12093
  • /34

    $339,900

    • 4 Beds
    • 2 Baths
    • 1,696 Sq Ft

    28 Spring St, Middletown, NY 10940

    Welcome to this 4-bedroom, 2-bathroom old-style home, nestled in the vibrant heart of Middletown. Recently renovated, this charming property is move-in ready and offers the perfect blend of traditional character and modern amenities. It offers open concept living. A nice size fenced in yard. Located just a short distance from Davidge Park, schools, and popular restaurants. New hot water heater,

    Leidy Placido Howard Hanna Rand Realty

    28 Spring St, 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
  • /25

    $668,000

    • 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
  • /34

    $2,995,000

    • 5 Beds
    • 2 Baths
    • 2,092 Sq Ft

    40 Camp Orange Rd, Middletown, NY 10941

    This versatile and lucrative investment or user property sits on one of the largest open land parcels left in the Town of Wallkill. Great Location on Route 211 between Middletown and Montgomery. Presently used as a dairy farm with many options for ag business or other type of business. Views would make this a great hospitality site, wedding venue, winery, brewery, ag tourism, retail dairy or

    Joe Distelburger Keller Williams Realty

    40 Camp Orange Rd, Middletown, NY 10941
  • /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
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