Middletown, NY Homes for Sale under $400,000

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  /20

  $305,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 689 Sq Ft

  15 Anthony St, Middletown, NY 10940

  *Welcome Home!* This exceptional *fully furnished and professionally designed* single-family residence is a rare turnkey opportunity, offering the perfect combination of style, comfort, convenience, and value. Beautifully updated and thoughtfully appointed, this approximately *690+/- sq. ft.* home is ready for immediate enjoyment—simply bring your personal belongings and move right in.The

  Eliezer Salcer Preferred Properties Real Esta

  15 Anthony St, Middletown, NY 10940
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• 

  

  

  /25

  $350,000

  • 2 Beds
  • 1 Bath
  • 1,007 Sq Ft

  608 Kirbytown Rd, Middletown, NY 10940

  Welcome to this bright and airy, mint-condition home nestled on 2 beautiful acres. This Ranch style home offers a wonderful blend of comfort and natural beauty. Mature landscaping, vibrant flower beds, raised vegetable gardens and a spacious patio create a peaceful outdoor setting perfect for relaxing and enjoying nature. This fabulous home features a sweeping open floor plan with vaulted

  Carol Buchanan BHG Real Estate Green Team

  608 Kirbytown Rd, Middletown, NY 10940
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  /2

  $395,000

  • 3 Beds
  • 1 Bath

  23 Bonnell St, Middletown, NY 10940

  2 family home in low traffic setting. 1st floor is 3 bedroom @ $1350./month plus utilities 2nd floor is 2 bedroom @ $1100/mo plus utilities Ist floor lease is annual until July 2027. 2nd floor month to month.Old storage building out back. Taxes about $500/mo insurance about $150./mo water about $50./mo

  Mark Tierney Howard Hanna Rand Realty

  23 Bonnell St, Middletown, NY 10940
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  /10

  $299,999

  • Land
  • 27.2 Acres
  • $11,029 per Acre

  328 Bloomingburg Rd, Middletown, NY 10940

  Fully Available!! Vacant Property directly across from Fair Oaks Drive in Movie theater and a gas station with plenty of road frontage!! Minutes to RT17. 27.2 ACRES!!! Electric on road at the front of the property! Possible small farm, Big enough for horses, growing crops, family compound. R2 Zoning.The owner is currently using the property to grow crops and has an Agricultural tax exemption.

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  

  

  /16

  $309,900

  • 2 Beds
  • 1 Bath
  • 1,248 Sq Ft

  40 Academy Ave, Middletown, NY 10940

  Charming 2-Bedroom Home in Downtown Middletown! This cozy two-story, 2-bedroom, 1-bath home is conveniently located within walking distance of restaurants, shops, and City Hall. The first floor features a spacious eat-in kitchen with access to the back porch and private backyard, along with a living room connected to a family room/study. Upstairs offers two generously sized bedrooms and a full

  Jonathon Lee KW Hudson Valley United

  40 Academy Ave, Middletown, NY 10940
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  /9

  $299,000

  • 2 Beds
  • 1 Bath
  • 560 Sq Ft

  220 Upper Kennedy, Middletown, NY 12455

  Catskills charm meets rustic luxury. Tucked away on a quiet dead-end road, this beautifully appointed cabin offers a rare combination of privacy, comfort and convenience. Thoughtfully decorated and impeccably cared for, the home features a brand new roof, cozy wood burning stove, country kitchen features a rolling island for flexibility and convenience The inviting interiors designed for

  Debra Smith Listing by Coldwell Banker Timberland Properties

  

  220 Upper Kennedy, Middletown, NY 12455
• 

  

  /22

  $328,000

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft

  43 Brick Pond Rd Unit 43, Middletown, NY 10940

  Rare opportunity in the sought-after Spring Hollow community! This very well-maintained 3-bedroom home offers a desirable and hard-to-find layout with 2 full baths and a half bath. Set on an elevated, quiet lot with a south-southeast exposure, the home enjoys beautiful lake views and a peaceful setting. The inviting living area features a wood-burning fireplace, while the updated kitchen offers

  Hai Li KW Hudson Valley United

  43 Brick Pond Rd Unit 43, Middletown, NY 10940
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  /29

  $289,000

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,181 Sq Ft

  21 Dolson Ave, Middletown, NY 10940

  The home offers 2 bedrooms plus an additional room that works well as an office or flex space, 1 full bathroom, and a functional kitchen. The backyard is a standout — generous in size with a large deck, great for warm weather. A walk-out basement adds useful storage. Washer/dryer hookup in unit. Currently tenant-occupied at $2,300/month, making this a ready-to-go investment from day one. Close to

  Jacob Fried Keller Williams Realty

  21 Dolson Ave, Middletown, NY 10940
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  /37

  $289,900

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

  141 Ruth Ct, Middletown, NY 10940

  Welcome to 141 Ruth Court! This move-in-ready two-bedroom, two-full-bath home has been freshly painted and features new carpeting throughout, offering a clean and inviting space that’s ready for you to make your own. With a comfortable layout, two bedrooms, and two full baths, this home is a wonderful opportunity for easy, turnkey living. Cathedral ceilings, 2 floors, open floor plan offering

  Dawn Gregg Curasi Realty, Inc.

  141 Ruth Ct, Middletown, NY 10940
• 

  

  /31

  $339,000

  • 2 Beds
  • 1 Bath
  • 992 Sq Ft

  26 Gardner Ave, Middletown, NY 10940

  A cozy and beautifully maintained home in a convenient location, this charming 2-bedroom, 1-bath property offers comfort, character, and thoughtful updates throughout. The updated kitchen and bathroom complement the warm hardwood floors on the main level, while raised dormers upstairs create a more spacious feel.The home features numerous important updates, including the roof, heating and

  Julie Kim Howard Hanna Rand Realty

  26 Gardner Ave, Middletown, NY 10940
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  /11

  $349,000

  $40K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,416 Sq Ft

  4 Harding St, Middletown, NY 10940

  Middletown Central Gem - Space, Character & Low Taxes!Minutes from Downtown Middletown, this solid 4-bedroom, 2-bath home offers the generous room proportions and practical layout characteristic of an older home, along with a large attic and full basement providing exceptional storage and future potential. A brand-new high-efficiency Navien tankless combination boiler adds modern

  Hai Li KW Hudson Valley United

  4 Harding St, Middletown, NY 10940
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  /5

  $215,000

  • Land
  • 1.1 Acres
  • $195,455 per Acre

  429 van Burenville Rd, Middletown, NY 10940

  Engineered lot pending approvals. Over 1 acre of land in the Town of Wallkill with Pine Bush Schools. This lot is "shovel ready", building docs have been submitted to the town and it's pending approvals. The lot is lovely, already cleared with the driveway conveniently cut in. There used to be a structure and it has been properly removed with permits, creating a perfect site to start building

  Valeria Rios KW Hudson Valley United

  429 van Burenville Rd, Middletown, NY 10940
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  /14

  $375,000

  $18K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,100 Sq Ft

  1 Chestnut St, Middletown, NY 10940

  Beautifully renovated 3 bedroom 1 bathroom, everything is brand new, electrical, plumbing and heating, plus with a big corner lot. Plenty of space, beautiful kitchen - come see it today.

  Safdar Mursalin eXp Realty

  1 Chestnut St, Middletown, NY 10940
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  /22

  $395,000

  $55K PRICE DROP

  • 1,450 Sq Ft

  13 Benton Ave, Middletown, NY 10940

  Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office SpaceThat is great for an accountant, attorney,Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hot water heaters. Large Parking Lot Second

  John Biasi Howard Hanna Rand Realty

  13 Benton Ave, Middletown, NY 10940
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  /24

  $299,999

  • 2 Beds
  • 1 Bath
  • 1,164 Sq Ft

  14 Airport Rd, Middletown, NY 10940

  14 Airport Road is ready for a little love and its next chapter. Located in the Town of Wallkill, this home offers a surprisingly spacious and flexible layout with plenty to work with for a buyer ready to roll up their sleeves and make it their own.The main level offers an open flow between the kitchen and living areas, with a brick fireplace adding character to the space. The kitchen is

  Cindy-Lee Dorcely KW Hudson Valley United

  14 Airport Rd, Middletown, NY 10940
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  /16

  $329,000

  • 2 Beds
  • 1.5 Baths
  • 1,144 Sq Ft

  15 N Aspen Rd, Middletown, NY 10940

  NO HOA FEES! LOW TAXES!! Welcome to easy, effortless living in this turnkey, move-in ready 2-bedroom home, thoughtfully updated with modern finishes and designed for today’s lifestyle. From the moment you step inside, you’re greeted by a bright and inviting interior that feels both stylish and comfortable. The updated kitchen shines with sleek countertops, crisp cabinetry, and modern appliances,

  Carmela Lopez Borrazas Serhant LLC

  15 N Aspen Rd, Middletown, NY 10940
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  /29

  $350,000

  $25K PRICE DROP

  • Land
  • 34.56 Acres
  • $10,127 per Acre

  0 W Hubbell Hill Rd Unit KEY1027019, Middletown, NY 12455

  Discover the possibilities with this exceptional 34+ acre land parcel nestled in a peaceful rural setting. Offering a perfect blend of open space, privacy, and natural beauty, this property provides an ideal canvas for your dream home, retreat, hobby farm, recreational getaway, or future investment.Surrounded by scenic countryside and abundant wildlife, the land offers plenty of room for

  Amanda Ferrantello Hudson Valley Griffith

  0 W Hubbell Hill Rd Unit KEY1027019, Middletown, NY 12455
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  /39

  $349,000

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft

  1630 Goshen Turnpike, Middletown, NY 10941

  Turnkey 3-Bed, 1-Bath with stunning mountain views! Completely remodeled from top to bottom with a brand-new upgraded kitchen, updated bath, and cozy living space. Features a versatile indoor porch, new deck, and a large backyard patio perfect for entertaining. Ready for you to move in!

  Yehuda Lefkowits MS Realty Group USA, Inc

  1630 Goshen Turnpike, Middletown, NY 10941
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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
• 

  

  /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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  /16

  $165,000

  $10K PRICE DROP Pre-Foreclosure

  • 1 Bed
  • 1 Bath
  • 748 Sq Ft

  488 Tally Ho Rd, Middletown, NY 10940

  A charming 1940 bungalow located in the highly desirable Minisink Valley School District, this home sits on a quiet 0.23-acre lot and makes an excellent starter home with low taxes. The front door opens into a spacious living area filled with natural light. The main level offers one bedroom plus an office that can serve as a second bedroom if needed. The full basement—not included in the listed

  Jason Schobert eXp Realty

  488 Tally Ho Rd, Middletown, NY 10940
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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
• 

  

  /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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  /20

  $146,900

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  394 Concord Ln, Middletown, NY 10940

  A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy

  Carol Scully Keller Williams Realty

  394 Concord Ln, 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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  /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
• 

  

  /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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  /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
• 

  

  /7

  $195,000

  $130K PRICE DROP

  • Land
  • 39.2 Acres
  • $4,974 per Acre

  0 Rebecca Dr, Middletown, NY 10940

  Large, rolling property which is predominately wooded. There is no "formal" road frontage, but in the adjoining Robin Meadows subdivision property abuts 2 points of access: 1 at the end of Maureen Drive and the other at the end of Rebecca Drive. Property is not engineered. Marcy South runs through the property. The power company maintains the land underneath the power line, making this a great

  Alan Eskew Howard Hanna Rand Realty

  0 Rebecca Dr, 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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  /2

  $175,000

  • Land
  • 3 Acres
  • $58,333 per Acre

  385 Midland Lake Rd, Middletown, NY 10941

  Welcome to 385 Midland Lakes Road—an exceptional opportunity to bring your dream home to life. This beautiful 3-acre fully engineered parcel is ideally situated within the Pine Bush School District, offering the perfect balance of peaceful surroundings and everyday convenience. Commuters will appreciate the close proximity to I-84, I-86, and the ShortLine bus station, while the City of Middletown

  Travis Thompson KW Hudson Valley United

  385 Midland Lake Rd, Middletown, NY 10941
• 

  

  /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
• 

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /8

  $159,000

  • Land
  • 18,600 Sq Ft
  • $372,365 per Acre

  47 Carpenter Ave, Middletown, NY 10940

  PRICE IMPROVED - Available for Sale is this Prime Vacant Lot with great visibility and traffic count. Zoned HC (Highway Commercial). Permitted uses include Financial institutions, office, religious, retail and service and repair shops. Uses by special permit include clubs and lodges, day care facilities, eating/drinking establishments, funeral parlors, hotel/motel, shopping centers, veterinary

  Jacqueline Henry-Thompson Jackie Henry Realty LLC

  47 Carpenter Ave, Middletown, NY 10940
• 

  

  /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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