Middletown, NY Homes for Sale under $500,000

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  /28

  $359,000

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  21 Keystone Park, Middletown, NY 10940

  What you've been waiting for! Adorable and affordable 3 BR ranch on a cul de sac with lovely, private back yard! Large LR! Kitchen opens to Dining area! New walk in shower in bath! Full basement and 1 car garage. C/A! HW floors! Newer windows! Municipal services! Convenient to shopping and Route 17 for commuter!

  Linda Clark Hudson Valley Griffith

  21 Keystone Park, Middletown, NY 10940
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  /23

  $399,995

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,663 Sq Ft

  17 Last Rd, Middletown, NY 10941

  Welcome to 17 Last Rd, a unique retreat nestled on a sprawling 3.9-acre lot in the heart of Middletown. The upper level features 2 bedrooms and 1 full bathroom, while the lower level offers ground-level access with its own separate entrance, an additional bedroom, and a full bathroom.This versatile 2-bedroom, 2-full-bathroom home is designed to maximize natural light, creating a bright

  Bryant Moran YourHomeSold Guaranteed Realty

  17 Last Rd, Middletown, NY 10941
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  /40

  $354,900

  • 3 Beds
  • 1 Bath
  • 1,104 Sq Ft

  41 Roosevelt Ave Unit 39, Middletown, NY 10940

  Welcome home to this beautifully maintained 3-bedroom, 1-bath Colonial in the City of Middletown. Conveniently located near shopping, restaurants, parks, schools, and major commuter routes, this home blends classic charm with practical everyday living. From the moment you arrive, you'll be drawn to the expansive wraparound front porch—the perfect place to enjoy your morning coffee or unwind at

  Patricia Sassi RE/MAX Benchmark Realty Group

  41 Roosevelt Ave Unit 39, Middletown, NY 10940
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  /29

  $399,000

  • 3 Beds
  • 2 Baths
  • 1,316 Sq Ft

  30 Chestnut Ave, Middletown, NY 10940

  Tucked into one of Middletown's established neighborhoods, 30 Chestnut Avenue is a home that effortlessly blends comfort, style, and convenience. From the moment you step inside, you'll appreciate the bright, open floor plan where natural light pours through the windows, creating inviting spaces designed for both everyday living and memorable gatherings.The heart of the home is the

  Lauren Iacono Corcoran Baer & McIntosh

  30 Chestnut Ave, Middletown, NY 10940
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  /2

  $484,900

  • 3 Beds
  • 2.5 Baths
  • 1,723 Sq Ft

  22 Atwood Dr, Middletown, NY 10940

  Beautiful 3-bedroom, 2.5-bath condo inside and out! Formal dining room, eat-in kitchen with island, cozy fireplace, and huge windows with custom blinds and curtains. Convenient second-floor laundry room! Spacious lower-level playroom—perfect for movie nights and large enough for your own home theater setup. Walk in closets, a soaking tub, central air and a 2 car garage! Low HOA fees and truly a

  Kelly Roebuck Curasi Realty, Inc.

  22 Atwood Dr, Middletown, NY 10940
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  /42

  $430,000

  $5K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  11 Columbia Ave, Middletown, NY 10940

  BEAUTIFULLY maintain old style home in the heart of Middletown with low PROPERTY taxes. A must-see home to appreciate it quality and charm. Located near Davidge Park. Commuter Friendly location easy access to Route 17 and interstate highway 84 to Penn and Conn. NJ Transit and a 15 min walk to the Shortline Bus to Midtown Manhattan with Plenty of Parking should you choose to drive to the bus

  Norberto Tirado N Tirado Realty LLC

  11 Columbia Ave, Middletown, NY 10940
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  /28

  $399,999

  Pre-Foreclosure

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  70 Peach Place, Middletown, NY 10940

  Welcome to 70 Peach Place, a beautifully maintained townhouse nestled in the desirable Peach Hills subdivision. This spacious home offers the perfect blend of comfort, convenience, and value with no HOA fees and low taxes.Step inside to discover newly updated bathrooms, new appliances, and a brand-new hot water heater, providing peace of mind for years to come. The generous primary suite

  Virginia Corbett eXp Realty

  70 Peach Place, Middletown, NY 10940
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  /2

  $283,000

  $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,545 Sq Ft

  187 Watkins Ave, Middletown, NY 10940

  Opportunity knocks in New York. Located near Sprucegate Farm, Swim King, and Magnanini Winery. This home has approx. 1,545 sq. ft. and a lot of approx. 7,750 sq. ft. A great investment opportunity. Buyers check with City, County, Zoning, Tax, and other records to their satisfaction. AS-IS SALE property.

  Neven Spralja Realhome Services and Solutions Inc

  187 Watkins Ave, Middletown, NY 10940
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  /23

  $490,000

  • 3 Beds
  • 2.5 Baths
  • 2,191 Sq Ft

  19 Magnolia Park Rd, Middletown, NY 10940

  BACK ON MARKET: Welcome to this beautifully maintained newer-construction home in the sought-after Magnolia Park section of the Maple Fields community in Middletown. Built in 2019–2020, this spacious residence offers approximately 2,100 square feet of modern living with an open-concept layout designed for today’s lifestyle. The main level features a bright and airy living space, a stylish kitchen

  Daniel Amodeo AMO Realty

  19 Magnolia Park Rd, Middletown, NY 10940
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  /15

  $329,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,176 Sq Ft

  195 Commonwealth Ave, Middletown, NY 10940

  Welcome to 195 Commonwealth Ave, where small-town charm meets everyday convenience. Nestled in the heart of Middletown, this 3-bedroom, 1-bath Cape Cod puts you minutes from the Metro-North train, shops, dining, and everything the Hudson Valley has to offer — with a backyard that feels like your own private retreat.Inside, gleaming hardwood floors flow throughout, anchored by a kitchen

  Loretta Wolff NexLvl Real Estate Inc.

  195 Commonwealth Ave, Middletown, NY 10940
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  /19

  $379,999

  • 2 Beds
  • 2 Baths
  • 1,252 Sq Ft

  8 Forest Ave Unit 6, Middletown, NY 10940

  Welcome to 8 Forest Ave, Middletown, NY 10940—a charming corner-lot home offering comfort, flexibility, and plenty of outdoor space.This well-maintained property features 2 spacious bedrooms plus a bright sunroom that can easily be converted into a third bedroom, home office, or guest room. The home also offers 2 full bathrooms, a generously sized kitchen, and a separate dining room,

  Mariama Balde Reliable Realty Group

  8 Forest Ave Unit 6, Middletown, NY 10940
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  /11

  $449,000

  • 4 Beds
  • 1,805 Sq Ft

  94 Linden Ave, Middletown, NY 10940

  Incredible opportunity to live in 1 unit and enjoy the additional income! Or an Investor. Both units features a Brand New Kitchen. Stainless Steal Appliances, Quartz countertops, eat-In-kitchen vinyl plank floors. 4 Bedrooms & 2 full bathrooms in total. Walk-out basement, laundry and storage. Separate utilities. HVAC, Siding and Roof 2023. Fenced in yard. The home is in close proximity to parks,

  Kevin Grier KW Hudson Valley United

  94 Linden Ave, Middletown, NY 10940
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  /25

  $289,000

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft

  63 Sycamore Dr, Middletown, NY 10940

  Welcome to the beautifully maintained Clemson Park complex. Upon entry you'll walk into the spacious, well-lit Living Room. This home also features a Formal Dining Room and Eat In Kitchen. You'll be able to access the balcony through the sliding glass doors in the living room to kick-back and relax on the deck. The Primary Bedroom offers his/her closets as well as a Primary Bathroom with an

  Kyle Pierce Patricia Schiller Real Est Co.

  63 Sycamore Dr, Middletown, NY 10940
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  /50

  $500,000

  $20K PRICE DROP

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

  29 Avoncroft Ln, Middletown, NY 10940

  Welcome to 29 Avon Croft Lane, One of a Kind Nestled among mature trees and natural surroundings, this property provides a peaceful and secluded setting. a beautifully maintained home offering privacy, comfort, and convenience in a desirable Middletown location. . This spacious home offers the comfort and freedom you’ve been looking for—about 70 miles from NYC, with easy access to major highways

  Gail Rachlin KW Hudson Valley United

  29 Avoncroft Ln, Middletown, NY 10940
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  /27

  $289,999

  $40K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft

  722 Silver Lake Scotchtown Rd, Middletown, NY 10941

  Beautifully renovated townhouse offering easy, two-level living. This desirable middle-unit home features 3 bedrooms and 1 full bathroom and 1 half bathroom with a bright, open layout designed for comfort and convenience. The spacious living areas flow seamlessly together, highlighted by brand-new flooring, the updated kitchen was recently completed and includes new cabinetry and appliances. All

  Gursharn Dhaliwal BHHS Hudson Valley Properties

  722 Silver Lake Scotchtown Rd, Middletown, NY 10941
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  /18

  $350,000

  $100K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,478 Sq Ft

  47 Wickham Ave Unit 45, Middletown, NY 10940

  Rare Opportunity to Live and Work under the same roof. Save money and time in buying this beautiful 1800’s Colonial Home in a very sought after area of Middletown. This Timeless Elegant home features Gorgeous wide Plank Flooring, beautiful Staircase and Rocking Chair Porches. This Charming home is Great for a professional I.E Accountant, Attorney, Real Estate Professional ETC This wonderful home

  John Biasi Howard Hanna Rand Realty

  47 Wickham Ave Unit 45, Middletown, NY 10940
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  /31

  $278,000

  $12K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,146 Sq Ft

  66 Deer Ct Dr, Middletown, NY 10940

  Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and good natural light. Building entry with controlled access and interior access to the second-floor unit. The living and dining areas are combined and connect to a galley kitchen with a pass-through opening. The primary bedroom features a walk-in closet and a private full bathroom. New carpet was installed in

  Jie Liu KW Hudson Valley United

  66 Deer Ct Dr, Middletown, NY 10940
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  /2

  $369,000

  Coming Soon

  • 2 Beds
  • 2 Baths
  • 2,236 Sq Ft

  49 Brewster Dr, Middletown, NY 10940

  Bring your vision and make this spacious bi-level your own! The main level features beautiful hardwood floors throughout the living and dining areas, along with a sliding glass door leading to the backyard patio, perfect for relaxing or entertaining. The home offers a flexible lower level with additional living space, providing plenty of room to accommodate a variety of needs. With some TLC, this

  Kismet Johnson eXp Realty

  49 Brewster Dr, Middletown, NY 10940
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  /34

  $225,000

  $5K PRICE INCREASE

  • 2 Beds
  • 1 Bath
  • 921 Sq Ft

  45 John St, Middletown, NY 10940

  Opportunity awaits! 2-bedroom, 1-bath one-family home with 2-car garage. Includes a large patio above the garage. Eat in kitchen with refrigerator and gas stove. The seller gutted and renovated the house in 1989. Property requires complete renovation and is being sold as-is. Ideal for investors, contractors, or buyers looking to build equity. Convenient location close to shopping, schools, and

  Jeffrey Lyons Curasi Realty, Inc.

  45 John St, Middletown, NY 10940
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  /24

  $399,999

  • 3 Beds
  • 3 Baths
  • 2,016 Sq Ft

  52 Linden Ave, Middletown, NY 10940

  This spacious 2,016 sq. ft. two-family home offers flexibility for both homeowners and investors. The first-floor unit features 1 bedroom, 1 full bathroom, and direct access to the basement. The second-floor unit offers 2 bedrooms and 2 full bathrooms, providing comfortable living space for occupants.Whether you're looking to live in one unit and generate rental income from the other, or

  Carina Villalona Hudson Premium Realty

  52 Linden Ave, Middletown, NY 10940
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  /46

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  1 Hulse St, Middletown, NY 10940

  Welcome home! This stunning newly constructed corner-lot residence offers the perfect blend of modern luxury, thoughtful design, and comfortable everyday living.Step inside to a bright, open main level featuring 9-foot ceilings, creating an inviting sense of space and sophistication. The heart of the home is the impressive upgraded kitchen, designed for both everyday living and entertaining.

  Anita S. Cristiano HomeSmart Homes & Estates

  1 Hulse St, Middletown, NY 10940
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  /41

  $369,900

  $79K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  202 Concord Ln Unit 202, Middletown, NY 10940

  Welcome to Buttonwood Hills! This spacious 3-bedroom, 2.5-bath townhouse offers comfortable, low-maintenance living in one of Middletown's most convenient locations. Featuring a bright and functional layout, the main level includes a generous living room, dining area, updated kitchen, convenient half bath, and in-unit laundry. Upstairs, you'll find a spacious primary bedroom along with two

  Soleil Jackman Howard Hanna Rand Realty

  202 Concord Ln Unit 202, Middletown, NY 10940

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