Middletown, NY Homes for Sale under $600,000

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  /2

  $324,999

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,480 Sq Ft

  63 Greenway Terrace, Middletown, NY 10941

  On the market for the first time in nearly 20 years! Welcome to 63 Greenway Terrace, a well-loved and maintained three-level townhome offering comfort, convenience, and plenty of living space. The open floor plan creates an inviting flow throughout the main level, complemented by three generously sized bedrooms and 1.5 bathrooms. Enjoy the convenience of newer appliances and a private, fenced

  Valerie Jewis Keller Williams Realty

  63 Greenway Terrace, Middletown, NY 10941
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  /20

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940

  Well-maintained 2-bedroom, 2 bathroom condo in the Deer Run Community with a 53-foot garage. Hardwood floors are throughout the open-concept living/dining room. The kitchen features stainless steel appliances. Recently updated washer, dryer (2025) and water heater (2025) and new windows. Primary bedroom features an en-suite bathroom and a walk-in closet.Conveniently located on the Dolson

  David Wilson Hudson Premium Realty

  18 Deer Ct Dr Unit Building 19 unit 18, Middletown, NY 10940
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  /49

  $495,000

  • 3 Beds
  • 2.5 Baths
  • 2,500 Sq Ft

  58 Cobblestone Ln, Middletown, NY 10940

  Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining.Additional features include a two-car attached

  Doreen Crowther Howard Hanna Rand Realty

  58 Cobblestone Ln, Middletown, NY 10940
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  /35

  $399,999

  $15K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft

  80 Beattie Ave, Middletown, NY 10940

  Welcome Home to Comfort, Style & Convenience in the Heart of Middletown!This beautifully renovated two-story Colonial blends timeless charm with modern updates, offering the perfect place to call home. Featuring 3 bedrooms, 1 full bathroom, and thoughtfully designed living spaces throughout, this move-in-ready property has been updated to maximize both functionality and style.From

  Sheyla Falesto Howard Hanna Rand Realty

  80 Beattie Ave, Middletown, NY 10940
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  /5

  $335,000

  • 3 Beds
  • 1 Bath
  • 1,224 Sq Ft

  41 Clinton St, Middletown, NY 10940

  3 Bedroom 1 bath ranch in Middletown! Close to Commuter Highways, Trains & ShoppingSOLD AS-IS SIGHT UNSEEN! CASH ONLY! DO NOT DISTURB OCCUPANTS!!

  Ernie Acampora River Realty Services, Inc.

  41 Clinton St, Middletown, NY 10940
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  /50

  $419,900

  $10K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  21 Harrison St, Middletown, NY 10940

  Welcome to this well-maintained 4-bedroom, 1.5-bath Victorian home offering a functional layout with numerous updates throughout. A covered front porch welcomes you inside, where the main level features a spacious living room, formal dining room, comfortable family room, updated kitchen, and a convenient half bath. Upstairs, you'll find four bedrooms and a full bathroom, providing a practical

  Jie Liu KW Hudson Valley United

  21 Harrison St, Middletown, NY 10940
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  /22

  $399,000

  $26K PRICE DROP

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

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to a move-ready condo in the desirable Walkill community. This splendid duplex has been 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 bedrooms lend a dramatic vibe for a

  Abraham Lefkowitz Access Realty Team Inc

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

  $333,000

  • 3 Beds
  • 1 Bath
  • 1,152 Sq Ft

  23 Harrison St Unit 25, Middletown, NY 10940

  Come see this well maintained 2 story colonial style home. Centrally located in the City of Middletown which allows you to be minutes away to all the great eateries and to all major shopping and public transportation. The home has taken a few updates over the years. Home has a spacious living room that leads into a formal dining room. Kitchen has plenty of cabinet space as well. The central a.c

  Pedro Garcia Curasi Realty, Inc.

  23 Harrison St Unit 25, Middletown, NY 10940
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  /32

  $479,000

  • 3 Beds
  • 2.5 Baths
  • 2,198 Sq Ft

  32 Woodstock Ln, Middletown, NY 10941

  Charming 3 bedroom, 2.5 bath home close to everything with Pine Bush Schools! Perfectly positioned just 2 minutes off of 211 in the heart of Middletown, you're just moments away from everything! Shopping, dining, transit and the areas most convenient commuter routes are all within 2 miles of this warm and inviting home. Step from the impressive entry foyer into a spacious open concept living and

  Anne Mahoney Hudson Valley Home Connection

  32 Woodstock Ln, Middletown, NY 10941
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  /17

  $337,000

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft

  5 Kendal Ln, Middletown, NY 10940

  Modern Comfort & Lake Access – The Best of Waters Edge!Welcome to this beautifully maintained 2-bedroom, 2.5-bath condo in the highly desirable Waters Edge community. Offering the perfect blend of peaceful lakeside living and modern convenience, this home features a bright, open floor plan designed for easy living. Most of the windows have been replaced, enhancing energy efficiency and

  Jonathon Lee KW Hudson Valley United

  5 Kendal Ln, Middletown, NY 10940
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  /44

  $324,000

  $31K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,830 Sq Ft

  122 Castle High Rd, Middletown, NY 10940

  Set on approximately 2 acres, this 1920’s unique multi-level home provides plenty of room to enjoy the outdoors. A standout feature is the property's unique location, offering road frontage on two separate roads, Castle High Road and Eatontown Road and both Agricultural and Residential zoning. Whether you've dreamed of creating your own homestead, raising chickens or other livestock, planting

  Denise Clancy Curasi Realty, Inc.

  122 Castle High Rd, Middletown, NY 10940
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  /43

  $415,000

  • 4 Beds
  • 2.5 Baths
  • 1,625 Sq Ft

  23 W Conkling Ave, Middletown, NY 10940

  BEAUTIFUL turn-key home located in a quiet neighborhood behind Orange County Community College of 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

  Sandra Arnez KW Hudson Valley United

  23 W Conkling Ave, Middletown, NY 10940
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  /32

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  13 Forest Ave, Middletown, NY 10940

  Fresh updates. New improvements. New opportunity.13 Forest Avenue is officially back on the market after completing repairs and updates, and it's ready for its next owner. This spacious home offers comfortable living, updated features, and a convenient location near schools, shopping, restaurants, and commuter routes. The recent improvements provide added value and confidence for buyers

  Pete Wolven Hudson Valley Home Connection

  13 Forest Ave, Middletown, NY 10940
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  /46

  $475,000

  $40K PRICE DROP

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

  23 Marcy Ln, Middletown, NY 10941

  Welcome to this beautifully renovated raised ranch in the desirable Scotchtown neighborhood. Offering over 1,700 square feet of living space, this move-in-ready home features 4 spacious bedrooms and 2 updated bathrooms.The bright main level offers a spacious L-shaped living and dining room filled with natural light, along with a beautifully renovated kitchen featuring brand-new stainless

  Dennis Aboagye Keller Williams Realty Group

  23 Marcy Ln, Middletown, NY 10941
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  /35

  $549,000

  • 3 Beds
  • 2.5 Baths
  • 2,053 Sq Ft

  45 Randall Heights, Middletown, NY 10940

  PRESIDENTIAL HEIGHTS now offers this LUXURY CONTEMPORARY home to make your forever home today! Set in the highly desirable Presidential Heights neighborhood, known for its beautiful homes, peaceful atmosphere, and close proximity to everyday essentials. A large wrap around blacktopped driveway along with paver stone walkway leads you inside this newly remodeled gem. Discover an incredible blend

  Sandra Arnez KW Hudson Valley United

  45 Randall Heights, Middletown, NY 10940
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  /19

  $575,000

  • 3 Beds
  • 3 Baths
  • 5,157 Sq Ft

  20 John St, Middletown, NY 10940

  For Sale: Income-Producing Mixed-Use Building in Prime Downtown MiddletownTake advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential.Property Overview:First Floor:Spacious 2,000 sq. ft. commercial space, currently used

  Jonathon Lee KW Hudson Valley United

  20 John St, Middletown, NY 10940
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  /38

  $399,900

  $20K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,204 Sq Ft

  39 California Ave, Middletown, NY 10940

  More space than meets the eye! This well-maintained 4-bedroom home features two first-floor bedrooms, a first-floor full bath, an enclosed sunroom, a full basement, a detached two-car garage, and a deep, level backyard. Notable improvements include a new roof, gutters, electrical panel, and exterior painting (2024); a new driveway (2023); whole-home updates in 2018 including new flooring

  Guoqing Ouyang Dalton Wade Real Estate Group

  39 California Ave, Middletown, NY 10940
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  /46

  $450,000

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  21 Manhattan Ave Unit 19, Middletown, NY 10940

  **Opportunities on Manhattan Avenue are few and far between. If you've been waiting for a home in this desirable neighborhood, your wait is over! ** Situated on a beautiful .25-acre lot, this inviting split-level offers the perfect combination of comfort, space, and style with **3 bedrooms, 1.5 baths, a one-car garage, and central air**.From the moment you walk through the door, you'll

  Rosalie Cook Weichert Realtors

  21 Manhattan Ave Unit 19, Middletown, NY 10940
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  /35

  $329,900

  • 2 Beds
  • 1.5 Baths
  • 1,340 Sq Ft

  50 Sycamore Dr, Middletown, NY 10940

  Welcome to Clemson Park!Discover this beautifully updated and well-maintained townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining.The bright living and dining area includes plush, well-maintained carpeted floors and sliding glass doors that open to a

  Maliki Cottrell Cottrell & Associates RE Corp.

  50 Sycamore Dr, Middletown, NY 10940
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  /36

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,257 Sq Ft

  4 Woodrose Ct, Middletown, NY 10940

  Welcome to 4 Woodrose Court, located in the peaceful Highrose Ridge community! Built in 2019, this modern townhome offers a bright, open layout with high ceilings, oversized windows and plenty of natural light.Step inside to hardwood floors throughout the main level and an open-concept kitchen featuring granite countertops, stainless steel appliances, a center island and plenty of space for

  Alyssa Scancarello Howard Hanna Rand Realty

  4 Woodrose Ct, Middletown, NY 10940
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  /43

  $385,000

  • 3 Beds
  • 2.5 Baths
  • 1,496 Sq Ft

  43 Mayer Dr, Middletown, NY 10940

  Welcome to this three-level townhouse in Middletown with no HOA, offering greater flexibility and no monthly association fees. The main level features a living room with hardwood flooring, a kitchen and dining area, and a half bathroom. The kitchen offers stainless steel appliances and ample cabinet and counter space. Sliding glass doors provide easy access to the rear deck and backyard for

  Wenpeng Guan KW Hudson Valley United

  43 Mayer Dr, Middletown, NY 10940
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  /39

  $505,000

  • 2 Beds
  • 2 Baths
  • 1,473 Sq Ft

  111 Jasmine Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill, one of the Hudson Valley's premier 55+ communities, where beautifully maintained grounds, outstanding amenities, and a true sense of community create an exceptional place to call home. Residents enjoy a beautiful clubhouse, fitness center, business center, indoor and outdoor swimming pools, tennis courts, recreation facilities, gated entry, and professionally

  Christina D'Altilio Coldwell Banker Choice Prop.

  111 Jasmine Dr, Middletown, NY 10940
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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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  /49

  $499,999

  • 3 Beds
  • 2.5 Baths
  • 1,660 Sq Ft

  81 Silver Lake Scotchtown Rd Unit 4, Middletown, NY 10940

  Experience modern living in this newly built 3-bedroom, 2.5-bath home designed with comfort and style in mind. Featuring an open floor plan with soaring 10-foot ceilings, this home offers spacious living and entertaining areas filled with natural light. The gourmet kitchen boasts granite countertops, stainless steel appliances, and ample cabinetry, all flowing seamlessly into the main living

  Antoinette Gundersen HomeSmart Homes & Estates

  81 Silver Lake Scotchtown Rd Unit 4, 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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  /21

  $485,000

  • 3 Beds
  • 2.5 Baths
  • 1,781 Sq Ft

  34 Field Stone Dr, Middletown, NY 10940

  Wow! Move right into this beautiful corner unit in Maple Fields offering plenty of living space, 3 bedrooms, 2.5 baths, a finished basement, and a 2-car garage. Features hardwood floors on the main level, a spacious kitchen with granite counters and ample cabinetry, and comfortable bedrooms with large closets and carpeted floors. The laundry is conveniently located upstairs. The finished basement

  Naomi Streicher Q Home Sales

  34 Field Stone Dr, Middletown, NY 10940
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  /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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  /38

  $499,000

  • 4 Beds
  • 2.5 Baths
  • 2,688 Sq Ft

  276 Spruce Rd, Middletown, NY 10940

  Welcome to this spacious Colonial in the Minisink Valley School District, nestled on 5 beautiful acres where privacy, nature, and comfortable living come together. Built in 2000, this 4-bedroom, 2 1/2 bath home offers approximately 2,688 square feet of living space with plenty of room to spread out.The traditional two-story layout features generous living areas, comfortable bedrooms, and

  Christine Torres KW Hudson Valley United

  276 Spruce Rd, Middletown, NY 10940
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  /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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  /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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  /46

  $489,999

  • 3 Beds
  • 3.5 Baths
  • 1,827 Sq Ft

  93 Meadow View Dr, Middletown, NY 10940

  This beautiful 3 bed 3 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes to transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a fireplace, full glass door leading to a very spacious deck for outdoor grilling or relaxation. Just

  Kevin Grier KW Hudson Valley United

  93 Meadow View Dr, 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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  /16

  $499,000

  $196K PRICE DROP

  • Land
  • 5.07 Acres
  • $98,422 per Acre

  0 Route 28 Unit 20261954, Middletown, NY 12455

  Rare opportunity: PRIME waterfront commercial lot in the heart of Margaretville on State Highway 28 -- unmatched visibility on the busy corridor. Zoned commercial with municipal sewer and water available. The East Branch of the Delaware River parallels the full length of the parcel, providing exceptional waterfront exposure and strong development potential. Seller has detailed plans available

  Katherine Keys The Catskill Dream Team

  0 Route 28 Unit 20261954, Middletown, NY 12455
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  /43

  $469,000

  • 5 Beds
  • 3 Baths
  • 2,448 Sq Ft

  495 Guymard Turnpike, Middletown, NY 10940

  Welcome home to this breathtaking Farmhouse-style retreat, perfectly set back from the main road amidst mature hydrangeas and Rose of Sharon. Step onto the sprawling, large rocking chair front porch—part of an expansive covered porch that wraps around three sides of the home—and experience true rustic charm before you even step inside. Upon entry, you’ll be in awe of the soaring vaulted ceilings,

  Maureen Cronin Cronin & Company Real Estate

  495 Guymard Turnpike, Middletown, NY 10940
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  /21

  $455,000

  • 4 Beds
  • 2 Baths
  • 1,466 Sq Ft

  225 Monhagen Ave, Middletown, NY 10940

  Great Location with C-2 Mixed-Use Zoning Potential! Located at 225 Monhagen Avenue in Middletown, this nicely maintained property offers a comfortable and practical layout along with exceptional flexibility for homeowners, investors, and business-minded buyers. The home features 4 bedrooms and 2 full bathrooms, providing generous space for comfortable family living. A finished basement adds

  Jin Pang Panorama Realty

  225 Monhagen Ave, Middletown, NY 10940
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  /25

  $478,000

  • 4 Beds
  • 2 Baths
  • 1,770 Sq Ft

  25 Independence Ave, Middletown, NY 10940

  It is located in one of Middletown's most desirable neighborhoods, where strong demand and steadily increasing home values make this an exceptional opportunity!This beautifully renovated, move-in-ready 4-bedroom home has been thoughtfully updated from top to bottom. The brand-new kitchen features modern cabinetry, a new stove, and an added pantry/storage closet, creating a stylish and

  Jin Pang Panorama Realty

  25 Independence Ave, 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
• 

  

  /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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  /37

  $525,000

  Open Sun 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft

  24 Beth Dr, Middletown, NY 10941

  Your home is this fully renovated 3-bedroom property that seamlessly blends modern interior elegance with an extraordinary backyard oasis! Step inside to an airy, light-filled open-concept floor plan showcasing fresh updates throughout, including sleek new flooring, modern lighting fixtures, and spa-inspired renovated bathrooms. The open gourmet kitchen serves as the heart of the home,

  Marc Cineus Howard Hanna Rand Realty

  24 Beth Dr, Middletown, NY 10941

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