Middletown, NY Homes for Sale under $500,000

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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
• 

  

  /35

  $200,000

  • Land
  • 51.7 Acres
  • $3,868 per Acre

  Tbd Hall Rd, Middletown, NY 12455

  Hike up to see this spectacular 51.7 acres of prime Real Estate. This property has everything except a road which will have to be built. A previous right of way was moved years ago due to flooding. The walk in does require waterproof boots and a lot of good energy. The parcel has every kind of topography you could imagine. Mouch of it is a large lightly wooded plateau. The southeastern boundary

  William Chris St. John Win Morrison Realty

  Tbd Hall Rd, Middletown, NY 12455
• 

  

  /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
• 

  

  /21

  $299,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  2 S Aspen Rd, Middletown, NY 10940

  Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make it your own. With 3 bedrooms, and a main-level flex space w/ closet, 2.5 bathrooms, plus inviting outdoor space, this home is ready for your personal touch. Close to everything Middletown offers—shops, dining, parks, and commuter routes—this is a smart move with big potential. Make 2 S. Aspen Rd your next

  Derek Greene Greene Realty Group

  2 S Aspen Rd, 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
• 

  

  /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
• 

  

  /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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  /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
• 

  

  /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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  /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
• 

  

  /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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  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /33

  $485,000

  $15K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  678 Prosperous Valley Rd, Middletown, NY 10940

  Welcome to 678 Prosperous Valley Road, a beautifully renovated Colonial nestled on 0.80 acres in the desirable Town of Middletown. Combining timeless character with modern upgrades, this move-in-ready home offers 4 spacious bedrooms, 2 full bathrooms, and approximately 1,861 square feet of thoughtfully updated living space.Recent improvements include a stunning remodeled kitchen, fully

  Yonauris Gonzalez Then eXp Realty

  678 Prosperous Valley Rd, Middletown, NY 10940
• 

  

  /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
• 

  

  /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
• 

  

  /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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