38

Middletown, NY 2-Story Homes for Sale

Section Image Section Image
  • /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
  • /41

    $539,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,130 Sq Ft

    63 Brimstone Hill Rd, Middletown, NY 10941

    Welcome to this outstanding, beautifully maintained Cape Cod-style home nestled on a serene 1.7-acre lot. This unique property combines timeless charm with thoughtful modern touches, offering both privacy and nature. Step onto the oversized front porch and take in the picturesque view of the front yard and classic natural fieldstone wall. As you enter through the soaring foyer, you'll be struck

    Agent Photo

    Jennifer Loprieno

    Howard Hanna Rand Realty

    (329) 219-0768

    63 Brimstone Hill Rd, Middletown, NY 10941
  • /30

    $379,000

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

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

    Looking for a solid investment in the Minisink Valley School District? This newer townhouse (Unit 2C, right side) is tenant-occupied with a lease in place through September 30, 2026, offering immediate income of $2,850/month. Tenants pay for oil and electric, are responsible, and come highly recommended. Privately set, this bright and welcoming home features an open foyer leading into an updated

    Agent Photo

    Hazel Cello

    Keller Williams Hudson Valley

    (845) 328-4272

    568 County Route 49 Unit 2C, Middletown, NY 10940
  • /9

    $250,000 Coming Soon

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

    34 Poplar Ln, Middletown, NY 10941

    This well-maintained home offers comfort, space, and convenience in a desirable location close to shopping, dining, and public transportation. Step inside to find generously sized bedrooms with vaulted ceilings that create an open and airy feel. The rear bedroom features a private balcony—perfect for morning coffee or unwinding at the end of the day. A full basement provides ample storage space,

    Agent Photo

    John Olivero

    Keller Williams Realty

    (329) 210-4787

    34 Poplar Ln, Middletown, NY 10941
  • /18

    $249,999

    • 2 Beds
    • 2 Baths
    • 880 Sq Ft

    215 Ruth Ct, Middletown, NY 10940

    One-Level Living at It's Finest – First Floor Condo in Middletown, NYWelcome to effortless living in this beautifully maintained first-floor condo, located in the heart of Middletown, NY. This spacious unit features brand new hardwood floors throughout, offering a warm and modern feel from the moment you step inside. The primary bedroom features a generous walk-in closet and a private

    Agent Photo

    Chativa Bowen

    Keller Williams Realty

    (329) 223-6211

    215 Ruth Ct, 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
  • /21

    $425,000

    • 3 Beds
    • 2 Baths
    • 1,639 Sq Ft

    389 Fair Oaks Rd, Middletown, NY 10940

    Beautiful contemporary capecod offers 3 to 4 bedrooms and 2 full bathrooms. Open kitchen/dining room with stainless steel appliances, brand new stove, microwave is only 1 year old. Large patio in front of the house. Ceramic tiles and hardwood floors throughout. Primary bedroom has a walk-in closet. First floor bedroom makes an ideal guest room, or for someone that doesn't want to do do stairs.

    Agent Photo

    Dulce M Ferrera

    Keller Williams Hudson Valley

    (329) 208-1615

    389 Fair Oaks Rd, Middletown, NY 10940
  • /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
  • /50

    $859,000

    • 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
  • /47

    $499,000

    • 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
  • /44

    $697,000

    • 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
  • /31

    $470,000

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

    295 Lybolt Rd, Middletown, NY 10941

    A/O 9.1.25 ... 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.

    Britanni Gaucher Keller Williams Realty

    295 Lybolt Rd, Middletown, NY 10941
  • /36

    $594,000

    • 4 Beds
    • 2.5 Baths
    • 2,292 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
  • /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
  • /36

    $799,000

    • 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
  • /34

    $384,000 Open Sat 11AM - 1PM

    • 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
  • /25

    $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
  • /15

    $129,000

    • 1 Bed
    • 1 Bath
    • 752 Sq Ft

    318 Ruth Ct, Middletown, NY 10940

    Welcome to this one-bedroom, one-bath condo located in the Eagles Point/Eastview Condominium community. This second floor unit offers an open floor plan that 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 into a warm and stylish home. Don't miss the opportunity to bring new

    Patricia Sassi RE/MAX Benchmark Realty Group

    318 Ruth Ct, Middletown, NY 10940
  • /50

    $379,000

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

    4 Russell Mews, Middletown, NY 10940

    Welcome to this beautifully updated home! Enjoy an open-concept kitchen with new cabinets; they're the larger size for extra storage. There's a large farm sink and a bump-out counter for additional seating. The appliances are on the newer side, including a microwave and dishwasher purchased in 2021, complemented with the stove and refrigerator that were updated in 2020. A convenient

    Luanne McGann Century 21 Full Service Realty

    4 Russell Mews, 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
  • /41

    $1,299,000

    • 6 Beds
    • 5.5 Baths
    • 4,650 Sq Ft

    80 Pine Grove Rd, Middletown, NY 10940

    Welcome to Your Private Estate in the greater Hudson Valley region, in the Town of Mount Hope, about 70 miles from NYC, set on over 120 acres of picturesque landscape, stone-lined pastures, rolling fields, serene woods, and a stocked bass pond. This remarkable property features a total of 3 master suites and 3 bedrooms, 3 Jacuzzi. All rooms have beautiful views for a peaceful recharge. It is

    Chris Ogden Realty Promotions Inc

    80 Pine Grove Rd, 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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /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
  • /18

    $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
  • /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

Home Trends in Middletown, NY

Housing Trends

Median Sale Price
$395,000
Median Single Family Sale Price
$415,000
Median Townhouse Sale Price
$400,000
Median 2 Bedroom Sale Price
$269,900
Median 1 Bedroom Sale Price
$172,000
Average Price Per Sq Ft
$242
Number of Homes for Sale
119
Last 12 months Home Sales
499
Months of Supply
2.90
Median List Price
$399,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
6%
How to Buy a Home How to Finance a Home How to Sell a Home