25

Middletown, NY Homes for Sale under $500,000

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  • /44

    $460,000

    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    23 Avoncroft Ln, Middletown, NY 10940

    Welcome to 23 Avoncroft Lane, a stately and airy three-bedroom end unit in the desirable Woodside Knolls community! This beautifully maintained home features modern updates, including a brand-new stove & microwave (to be installed before closing), stainless steel appliances, a new refrigerator (2024), a newer washing machine (2022), a new garage door (4/2025), basement electrical outlets were

    Carol Cruz Keller Williams Hudson Valley

    23 Avoncroft Ln, Middletown, NY 10940
  • /42

    $469,000

    • 3 Beds
    • 2.5 Baths
    • 1,940 Sq Ft

    23 Macintosh Dr, Middletown, NY 10941

    Welcome to Scotchtown! This true raised ranch offers room for all, with extensive improvements and quality updates throughout. Enjoy a neighborhood setting with the convenience of town of Wallkill amenities just minutes away! Step inside to a bright, light-filled interior with two levels of living space and a comfortable floor plan. Hardwood floors flow throughout the main spaces, while a vaulted

    Laurel Lustgarten Howard Hanna Rand Realty

    23 Macintosh Dr, Middletown, NY 10941
  • /30

    $489,900

    • 3 Beds
    • 2.5 Baths
    • 2,832 Sq Ft

    22 Mark Dr, Middletown, NY 10940

    Grand Colonial in the Minisink Valley School District on 1.7 Acres! Welcome to this stately colonial, offering space, charm, and endless potential. With your personal touches and updates this incredible home can truly shine! Set on 1.7 acres of beautiful property, this home provides the perfect balance of space, convenience, and privacy—all within the highly sought-after Minisink Valley School

    Frank Muccari Cronin & Company Real Estate

    22 Mark Dr, Middletown, NY 10940
  • /36

    $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
  • /40

    $489,900

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    11 Cobblestone Ln, Middletown, NY 10940

    Welcome to this bright and spacious 3-bedroom, 2.5-bath townhouse, that’s perfect for today’s busy lifestyle. The spacious layout is filled with natural light, creating a warm and inviting atmosphere for all to gather. The main level offers plenty of room for both everyday living and entertaining, while the upper level features comfortable bedrooms, including a primary suite with its own private

    Antoinette Gundersen HomeSmart Homes & Estates

    11 Cobblestone Ln, Middletown, NY 10940
  • /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
  • /43

    $419,900

    • 3 Beds
    • 3 Baths
    • 2,214 Sq Ft

    242 Derby Rd, Middletown, NY 10940

    Some homes simply check the boxes. Others feel like they were built with care from the ground up. 242 Derby Road is one of those rare finds, offering the peace of mind that comes with knowing every detail is brand new.From the curb, you’ll notice the fresh siding, new roof, and paved driveway. Inside, over 2,094 square feet of modern comfort welcome you with natural light, clean finishes,

    Isaiah Lopez Keller Williams Hudson Valley

    242 Derby Rd, Middletown, NY 10940
  • /27

    $425,000

    • 3 Beds
    • 1.5 Baths
    • 1,780 Sq Ft

    29 Cornfield Rd, Middletown, NY 10940

    Welcome to your new home in the highly sought-after Minisink Valley School District! This beautiful raised ranch offers the perfect combination of comfort, style, and convenience, all set within a peaceful low traffic neighborhood.Step inside to find hardwood floors flowing seamlessly through the main living areas. The spacious, sun-drenched family room creates a warm and inviting atmosphere,

    Frank Muccari Cronin & Company Real Estate

    29 Cornfield Rd, Middletown, NY 10940
  • /30

    $430,000

    • 3 Beds
    • 2 Baths
    • 1,532 Sq Ft

    25 Wayne Dr, Middletown, NY 10940

    Welcome to Your New Home in Robins Meadows! Nestled in the highly sought-after Minisink Valley School District, this beautiful raised ranch sits proudly on a large corner lot, offering the perfect blend of comfort, style, and convenience in a serene, friendly neighborhood. Step inside to find hardwood floors flowing seamlessly through the main living areas. The sun-drenched family room creates a

    Frank Muccari Cronin & Company Real Estate

    25 Wayne Dr, Middletown, NY 10940
  • /37

    $439,000

    • 3 Beds
    • 1.5 Baths
    • 1,104 Sq Ft

    160 Gillen Rd, Middletown, NY 10940

    Welcome home to this beautifully updated 3-bedroom, 2-bath ranch, perfectly situated on over 1 acre of land and offering the ideal blend of space, comfort, and modern upgrades. Featuring an oversized 2-car garage, a bright and inviting floor plan, and a walk-out basement, this property combines classic charm with a serene, retreat-like setting. Step inside to a spacious, sun-filled eat-in

    Marie Savage Curasi Realty, Inc.

    160 Gillen Rd, Middletown, NY 10940
  • /46

    $449,000

    • 4 Beds
    • 3 Baths
    • 1,732 Sq Ft

    9 Birchwood Ln, Middletown, NY 10940

    Welcome to Robin Meadows, located in the highly sought-after Minisink Valley School District! This beautifully maintained raised ranch is truly turn-key and ready for its new owners. Featuring four bedrooms and three full bathrooms, this home offers both comfort and functionality. Inside, you’ll find oak hardwood floors on the upper level—no carpets—and freshly painted walls that create a warm,

    Susan Giordano John J Lease REALTORS Inc

    9 Birchwood Ln, Middletown, NY 10940
  • /22

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,337 Sq Ft

    19 Putters Way Unit 9, Middletown, NY 10940

    Welcome to this fully updated, move-ready condo in the desirable Walkill community. This splendid duplex has been luxuriously upgraded with modern paint tones and the latest finishes. Bright and sunny rooms with updated lighting throughout. The kitchen boasts sleek, brand-new appliances and classic wood cabinetry. The bathrooms have been meticulously maintained. Cathedral ceilings in both

    Abraham Lefkowitz Access Realty Team Inc

    19 Putters Way Unit 9, Middletown, NY 10940
  • /39

    $489,000

    • 2 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    4 Putters Way, Middletown, NY 10940

    Beautiful townhouse-style condo in the gated community of The Fairways. Walk in to a tiled foyer leading you to a den with full egress windows. Built-in cabinets for display and for storage. Up the stairs you have a beautiful living room with 2nd floor large windows with views overlooking the charming street. Corner gas fireplace, more built-ins for display and for entertaining ease. The

    Susanne Dermigny Howard Hanna Rand Realty

    4 Putters Way, 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
  • /30

    $409,000

    • 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
  • /24

    $459,900

    • 3 Beds
    • 2 Baths
    • 2,400 Sq Ft

    652 New York 211 Unit 650, Middletown, NY 10940

    FOR SALE: Versatile Mixed-Use Building – Ideal for Owner-Operator | 650-652 Route 211 W, Middletown, NY 10940A rare opportunity to own a fully updated 2-unit standalone building in a prime high-visibility corner location at Route 211 West and California Drive in the Town of Wallkill.Property Overview:Total Building Size: Approx. 2,400 sq ftLot Size: Generous lot with

    Jonathon Lee Keller Williams Hudson Valley

    652 New York 211 Unit 650, Middletown, NY 10940
  • /38

    $489,999

    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    7 Avoncroft Ln, Middletown, NY 10940

    Discover the perfect balance of modern design and everyday comfort in this beautifully updated 3-bedroom, 3-bath corner townhouse, ideally located in one of Middletown’s most sought-after neighborhoods. Step inside and be welcomed by a bright, open-concept living space that feels both chic and inviting. The stylishly renovated kitchen is a true standout and it is complete with sleek countertops,

    Kewin Garabito eXp Realty

    7 Avoncroft Ln, Middletown, NY 10940
  • /21

    $489,000

    • 2 Beds
    • 2 Baths
    • 3,090 Sq Ft

    6 Broad St, Middletown, NY 10940

    Great two family duplex located in the City of Middletown. It's conveniently located walking distance to Touro College , I84 and I86, and also close to local shops and restaurants . Located approximately 70 miles North of New York City this property has a strong income potential with long term upside . At one time this was a triplex and is now a legal duplex. The 1st floor apartment has 2

    Neal Kolze Curasi Realty, Inc.

    6 Broad St, Middletown, NY 10940
  • /34

    $429,999

    • 2,946 Sq Ft

    221 E Main St, Middletown, NY 10940

    Welcome to 221 E Main St—a standout investment opportunity offering flexibility, location, and long-term potential in one of Orange County’s most active and rapidly growing markets. This mixed-use property features two residential units and a commercial space on the ground floor, making it an ideal choice for investors, owner-occupants, or entrepreneurs looking to establish a business while

    Savannah Miceli Century 21 Alliance Rlty Group

    221 E Main St, Middletown, NY 10940
  • /31

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,531 Sq Ft

    484 Route 211 W, Middletown, NY 10940

    Welcome to 484 Route 211 – an amazing opportunity in the heart of Middletown for anyone ready to take on a rewarding project with big potential! This spacious home features 4 generously sized bedrooms and 2 full bathrooms, offering plenty of room for a large or growing family. The eat-in kitchen is perfect for family meals, and there’s even a first-floor bedroom for added convenience.One

    Virginia Corbett eXp Realty

    484 Route 211 W, 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
  • /43

    $425,000

    • Land
    • 63.3 Acres
    • $6,714 per Acre

    0 Bragg Hollow Rd, Middletown, NY 12438

    Investors, nature lovers, outdoor enthusiasts, discover the opportunity of a lifetime with this stunning 66.5-acre surveyed parcel of land nestled in the Catskill Mountains. This remarkable property offers not only a pristine natural setting but also breathtaking land, featuring pristine forested areas, open pastures, and picturesque meadows and quarries. Waterfalls, streams, trails throughout

    Susan Doig Listing by Coldwell Banker Timberland Properties

    0 Bragg Hollow Rd, Middletown, NY 12438
  • /30

    $469,000 Pre-Foreclosure

    • 3 Beds
    • 2.5 Baths
    • 2,567 Sq Ft

    30 Avoncroft Ln, Middletown, NY 10940

    Move-In Ready at 30 Avoncroft Lane, Middletown, NYTired of cramped city living? This spacious home offers the comfort and freedom you’ve been looking for—just about 70 miles from NYC, with easy access to major highways and minutes from public transportation for a smooth commute. You’ll also love being close to shopping, restaurants, schools, and even the hospital—everything you need is

    Cindy-Lee Dorcely Keller Williams Hudson Valley

    30 Avoncroft Ln, Middletown, NY 10940
  • /42

    $435,000 Coming Soon

    • 4 Beds
    • 2 Baths
    • 1,392 Sq Ft

    284 Ohaire Rd, Middletown, NY 10941

    For the first time in over 60 years, this cherished 1960’s 4-bedroom, 2-bath ranch is ready to welcome its next owners. Lovingly cared for by the same family for 63 years, this home radiates warmth and pride of ownership. Inside, you’ll find a comfortable single-level layout with a bright living room, spacious bedrooms, and an inviting kitchen and dining area that have hosted countless family

    Antoinette Gundersen HomeSmart Homes & Estates

    284 Ohaire Rd, Middletown, NY 10941
  • /6

    $425,000 Coming Soon

    • 4 Beds
    • 3 Baths
    • 1,728 Sq Ft

    42 Genung St, Middletown, NY 10940

    BEAUTIFUL turn-key home located in MIDDLETOWN! Do NOT let the ouside fool you as this home is bigger than expected... Step inside this Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to kitchen. New vinyl floors and recessed lighting throughout. Modern eat-in kitchen with new white cabinets, granite countertops, backsplash & gorgeous fresh out the

    Sandra Arnez Keller Williams Hudson Valley

    42 Genung St, 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
$380,000
Median 2 Bedroom Sale Price
$275,000
Median 1 Bedroom Sale Price
$175,000
Average Price Per Sq Ft
$243
Number of Homes for Sale
123
Last 12 months Home Sales
502
Months of Supply
2.90
Median List Price
$399,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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