Newest Homes for Sale in Middletown, NY

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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
• Explore Middletown

• 

  

  

  /5

  $345,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,380 Sq Ft

  8 Budd Ave, Middletown, NY 10940

  Step into the warmth and charm of this beautifully maintained Colonial, where classic character meets comfortable modern living. Gleaming hardwood floors flow throughout much of the home, complementing the inviting architectural details found throughout.The spacious, sun-filled Living Room features an arched doorway leading to the Formal Dining Room—perfect for entertaining or enjoying

  Richard Froehlich RE/MAX Benchmark Realty Group

  8 Budd Ave, Middletown, NY 10940
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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
• 

  

  

  /21

  $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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  /50

  $688,000

  • 3 Beds
  • 2.5 Baths
  • 2,646 Sq Ft

  151 Bowser Rd, Middletown, NY 10940

  Lot & Natural SettingGenerous Acreage & Privacy: Situated on a spacious, private lot surrounded by scenic Hudson Valley greenery, offering peace, quiet, and minimal drive-by traffic.Outdoor Living Potential: Abundant usable yard space ideal for entertaining, gardening, a patio or deck, outbuildings, or potential pool additions.Tranquil Country Atmosphere: Enjoy the feel of

  Zhiheng Tang KW Hudson Valley United

  151 Bowser Rd, Middletown, NY 10940
• 

  

  /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
• 

  

  /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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  /46

  $625,000

  • 3 Beds
  • 3 Baths
  • 2,470 Sq Ft

  58 Burnt Corners Rd, Middletown, NY 10940

  Welcome to Your Private Country Retreat! Nestled on 3.2 acres of serene, private land within the desirable Minisink Valley School District, this spacious 2,470 sq. ft. home blends peaceful nature with modern comfort. Step inside from the welcoming front deck into a bright foyer leading to a formal living room with striking vaulted ceilings and a formal dining room filled with natural light. The

  Toni Kreusch BHG Real Estate Green Team

  58 Burnt Corners Rd, Middletown, NY 10940
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  /40

  $690,000

  $200K PRICE INCREASE

  • 5 Beds
  • 3 Baths
  • 2,804 Sq Ft

  20 3rd St, Middletown, NY 10940

  This single-family residence bi-lonial was built in 2007, features 5 bedrooms, and 3 full bathrooms. house is newly remodeled.

  Feng Chang Acer Realty Inc

  20 3rd St, Middletown, NY 10940
• 

  

  /27

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft

  41 Irwin Ave, Middletown, NY 10940

  The covered front porch, hardwood floors, and separate rooms give this home the kind of simple, straightforward layout that has worked for generations and still works today. Step inside and you'll find plenty of natural light, along with distinct living and dining rooms that each have their own purpose without making the home feel disconnected.The kitchen is practical and well equipped,

  Joshua Papka Keller Williams Realty HV Nort

  41 Irwin Ave, Middletown, NY 10940
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  /41

  $529,000

  • 3 Beds
  • 2 Baths
  • 1,753 Sq Ft

  95 Silver Lake Scotchtown Rd, Middletown, NY 10940

  Welcome to this beautifully renovated Cape Cod, where classic charm meets modern design. This turnkey home offers 3 bedrooms and 2 full bathroom, including a convenient first-floor bedroom perfect for guests, a home office, or easy one-level living. Thoughtfully redesigned from top to bottom, updates include brand-new flooring throughout, a sleek modern kitchen with quartz countertops and new

  

  Ammar Iqbal

  eXp Realty

  95 Silver Lake Scotchtown Rd, Middletown, NY 10940
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  /3

  $899,999

  • 5 Beds
  • 4 Baths
  • 3,820 Sq Ft

  2096 Route 6, Middletown, NY 10940

  Beautifully renovated. Brand new addition 2025. Floor to ceiling stone fireplace with wood burning stone insert, open concept, plenty of room for entertainment. In law set up with kitchenette.

  Silena Mauro S M Target Realty, LLC

  2096 Route 6, 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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  /50

  $545,000

  • 3 Beds
  • 2.5 Baths
  • 2,508 Sq Ft

  2 Harvest Hill Ln, Middletown, NY 10940

  Welcome home to this spacious and beautifully maintained Middletown property, ideally situated on a desirable corner lot and offering the perfect combination of space, comfort, and convenience. Step inside to a bright and inviting interior featuring hardwood flooring and an open, comfortable layout designed for both everyday living and entertaining. The well-appointed kitchen features stainless

  Kevin Grier KW Hudson Valley United

  2 Harvest Hill Ln, Middletown, NY 10940
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  /5

  $75,000

  • Land
  • 12,501 Sq Ft
  • $261,324 per Acre

  92-94 Anthony St, Middletown, NY 10940

  Beautiful piece of land in the City of Middletown!! Bring your plans and your vision! Public Water, Public Sewer, Natural Gas! Surrounded by brand new homes! Call today!

  Frank Muccari Cronin & Company Real Estate

  92-94 Anthony St, Middletown, NY 10940
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  /42

  $215,000

  • 1 Bed
  • 1 Bath
  • 879 Sq Ft

  11 Brittany Dr, Middletown, NY 10940

  Welcome to a low-maintenance lifestyle, minimal utilities, included heat and hot water, generous storage, and a commuter-friendly setting. This condominium is an excellent opportunity for buyers looking for comfort and convenience . Located in a quiet, peaceful neighborhood, this second-floor condo offers a welcome retreat while still being close to varied amenities and transportation options

  Amanda Ferrantello Hudson Valley Griffith

  11 Brittany Dr, 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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  /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
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  /33

  $499,000

  • 3 Beds
  • 2.5 Baths
  • 1,328 Sq Ft

  3 Allerton Ave, Middletown, NY 10940

  Welcome to 3 Allerton Ave, a charming and well-maintained Ranch-style home nestled in one of Middletown’s sought-after neighborhoods. Set on a private 0.20-acre lot, this inviting property offers a peaceful suburban setting with shopping, dining, public transportation, and commuter routes just minutes away. A welcoming front porch leads into a bright foyer and semi-open living space connecting

  

  Erin Connolly-Frontino

  Artisan Realty

  3 Allerton Ave, Middletown, NY 10940
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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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  /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
• 

  

  /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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  /33

  $475,000

  • 4 Beds
  • 2.5 Baths
  • 2,152 Sq Ft

  8 Pine St, Middletown, NY 10940

  Come view this beautifully appointed Raised Ranch in a commuter-friendly area of Middletown . This 4 bedroom two bath home boasts an open kitchen concept with 4 generous sized bedrooms upstairs an open downstairs area that can become anything you desire. It comes fully equipped with all appliances. You will also enjoy the spacious canopied deck and pool. Act now and you can bein this wonderful

  Robin White KW Hudson Valley United

  8 Pine St, Middletown, NY 10940
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  /14

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 1,348 Sq Ft

  35 Lexington Way, Middletown, NY 10940

  Prime Location & NeighborhoodCommuter Convenience: Minutes from Route 17 (Future I-86), Interstate 84, and the Middletown Metro-North train station, providing a straightforward commute toward NYC and Westchester.Proximity to Key Amenities: Close to Garnet Health Medical Center, SUNY Orange, and the Route 211 commercial corridor (major shopping centers, dining, and grocery

  Zhiheng Tang KW Hudson Valley United

  35 Lexington Way, Middletown, NY 10940
• 

  

  /10

  $85,000

  • Land
  • 1.9 Acres
  • $44,737 per Acre

  64 Brola Rd, Middletown, NY 10940

  Fantastic opportunity to build a new home within the Minisink school district. Level, 1.9 acre lot featuring frontage on the Little Shawangunk Kill. The location is serene yet in close proximity to your everyday conveniences such as shops, restaurants, parks and much more.

  Nicholas Carbone HomeSmart Homes & Estates

  64 Brola Rd, Middletown, NY 10940
• 

  

  /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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  /50

  $759,900

  • 4 Beds
  • 2.5 Baths
  • 2,572 Sq Ft

  473 Ingrassia Rd, Middletown, NY 10940

  Gorgeous Center Hall Colonial situated on 5 Beautiful Acres in the Pine Bush School District. This Pristine Home features an Inviting and welcoming Entry. Open Airy Floor Plan, Hardwood Floors Throughout the first floor, Large Living Room, Spacious Formal Dining Room that is great for dinner parties. Beautiful Designer Kitchen with Custom built cabinetry with under mounted lighting, Exotic

  John Biasi Howard Hanna Rand Realty

  473 Ingrassia Rd, Middletown, NY 10940
• 

  

  /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
• 

  

  /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
• 

  

  /31

  $299,900

  • 3 Beds
  • 1 Bath
  • 860 Sq Ft

  256 Cottage St Unit 258, Middletown, NY 10940

  The first thing you will do here is walk out into that lawn and start deciding where everything goes, the garden along the sunny side, the fire pit set well back, the patch under the old shade tree that stays empty because that is the coolest spot on the property and you are going to want it for yourself. The lot is 0.28 acres, flat and open, and every bit of it comes with the keys. Not many city

  

  Brian Caplicki

  KW Hudson Valley United

  256 Cottage St Unit 258, 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
• 

  

  /31

  $359,000

  • 3 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  21 Black Stallion Ct, Middletown, NY 10940

  Welcome to inviting, freshly painted, updated 3-bedroom, 1.5-bathroom home in The Meadows community~Main floor offers kitchen-with brand new cabinets, new stainless steel appliances, granite countertops, roomy dining area, bright and expansive living room with large bay window and half bathroom~Door from the kitchen leads to the large deck perfect for relaxing and entertaining your guests

  Liene Kasparsons Keller Williams Realty

  21 Black Stallion Ct, 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
• 

  

  /28

  $549,900

  82 Montgomery St Unit 84, Middletown, NY 10940

  Turn-of-the-century solid brick two-family home situated on a desirable corner lot comprising two lots. This owner-occupied property offers a spacious yard with established grapevines and mature fruit trees, creating a wonderful setting for outdoor enjoyment.An excellent opportunity for an owner-occupant looking for a home with rental income potential. The main-floor unit features 2

  Jonathon Lee KW Hudson Valley United

  82 Montgomery St Unit 84, Middletown, NY 10940
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  /9

  $115,000

  • 2 Beds
  • 1 Bath
  • 432 Sq Ft

  13 Birch St, Middletown, NY 10940

  Set among the trees on a private dirt road, this compact cottage offers a quiet place to get away without being far from everyday conveniences. The home features a ductless system for heating and cooling, a newer water heater, an updated bathroom, a new septic system, a new well, and a simple, low-maintenance layout. Outside, the wooded property includes a stone wall, natural fern-covered areas,

  Patricia Lucey Picture It Sold, LLC

  13 Birch St, Middletown, NY 10940
• 

  

  /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
• 

  

  /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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  /33

  $599,900

  • 4 Beds
  • 2.5 Baths
  • 2,354 Sq Ft

  282 Derby Rd, Middletown, NY 10940

  Tucked at the end of a long, paved drive on a quiet country road, this secluded 4-bedroom, 2.5 bath retreat feels worlds away — while still being minutes from everything you need. Five minutes away from major highways and less than ten minutes away from shopping and restaurants. Located in the desirable Pine Bush School District.Step inside to a light-filled first floor featuring maple

  Thomas Grazier I Realty LLC

  282 Derby Rd, Middletown, NY 10940
• 

  

  /49

  $579,000

  • 4 Beds
  • 3 Baths
  • 2,368 Sq Ft

  34 Hawthorne Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill, Orange County's premier 55+ community! Something Special! This 4 BR, 3 bath beauty is open and sun filled with vaulted ceilings and lovely detailed chair railings! 10 ft. ceilings and new wood floors throughout 1 st floor! Large LR opens to DR! Kitchen with island and undercounter lighting opens to vaulted family room with gas fireplace! Primary suite is on

  Linda Clark Hudson Valley Griffith

  34 Hawthorne Dr, Middletown, NY 10940
• 

  

  /37

  $299,000

  • 3 Beds
  • 1 Bath
  • 1,246 Sq Ft

  293 Highland Ave Extension, Middletown, NY 10940

  Offering over 1,200 square feet of one-level living, this home still has some of the fun details that made the 1950’s so memorable. A classic Dutch door? Check. Original woodwork? Absolutely. Hardwood floors hiding beneath the carpeting? They’re just waiting to make their comeback. And that fabulous pink-tiled bathroom? We say embrace it! The enclosed porch is another favorite—a cozy little spot

  Patricia Sassi RE/MAX Benchmark Realty Group

  293 Highland Ave Extension, Middletown, NY 10940

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