Middletown, NY Homes

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  /49

  $625,000 Pending

  • 8 Beds
  • 6 Baths
  • 3,240 Sq Ft

  128 W Main St, Middletown, NY 10940

  THEY DON'T MAKE THEM THIS BIG ANYMORE!!! Absolutely STUNNING MIDDLETOWN MULTI-FAMILY is now available for your purchase!! This OVERSIZED Colonial is in R-2 zone and if space is what you need, look no further as you have found it!! Ideal for an extended family, live in one and rent out the other or lastly allow the rental income of BOTH units pay off your mortgage! TURN-KEY condition and both

  Sandra Arnez Keller Williams Hudson Valley

  128 W Main St, Middletown, NY 10940
• 

  $400,000 Sold Jun 20, 2025

  29 Peach Place, Middletown, NY 10940

  • 4 Beds
  • 4 Baths
  • 1,864 Sq Ft
  • Built 2001

  Last Sold Summary

  • 2% Below List Price
  • $215/SF
  • 24 Days On Market

  Current Estimated Value $412,078

  Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

  29 Peach Place, Middletown, NY 10940
• 

  Est $464,754 Not Listed For Sale

  20 Placid Ave, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft
  • Built 1984

  20 Placid Ave, Middletown, NY 10941

  Last Sold Summary

  • 15% Above List Price
  • $280/SF
  • 77 Days On Market

  Last Sold Price $405,000

  Last Listing Agent Karen Taphorn Howard Hanna Rand Realty
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  /18

  $675,000

  • 8 Beds
  • 3 Baths
  • 3,000 Sq Ft

  21-23 Highland Ave, Middletown, NY 10940

  Kathleen Christopherson EXCLUSIVE SALES AND RENTALS

  21-23 Highland Ave, Middletown, NY 10940
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  $630,000 Sold Apr 28, 2025

  28 Vincenzo Ct, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 3,608 Sq Ft
  • Built 2005

  Last Sold Summary

  • 9% Below List Price
  • $175/SF
  • 104 Days On Market

  Current Estimated Value $656,559

  Last Listing Agent Rachel Jones Jason Mitchell Real Estate NY

  28 Vincenzo Ct, Middletown, NY 10940
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  Est $493,297 Not Listed For Sale

  15 Placid Ave, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 2,088 Sq Ft
  • Built 1986

  15 Placid Ave, Middletown, NY 10941

  Last Sold Summary

  • 4% Above List Price
  • $227/SF
  • 31 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Dulce M Ferrera Keller Williams Hudson Valley
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  /44

  $605,000

  • 4 Beds
  • 3 Baths
  • 2,132 Sq Ft

  125 White Bridge Rd, Middletown, NY 10940

  This home offers so much more than a new build. Enjoy 2,132 square feet of well maintained, comfortable living space, topped with a brand new roof. Set on 2.6 beautiful acres in a serene country setting, the property’s signature feature is its fully owned solar array. No roof penetrations, no lease agreements — just clean energy and real savings. Electric bills as low as $28 per month speak for

  Anthony Spadaro RE/MAX Benchmark Realty Group

  125 White Bridge Rd, Middletown, NY 10940
• 

  $300,000 Sold Oct 14, 2025

  7 Wilbur Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,922 Sq Ft
  • Built 1892

  Last Sold Summary

  • 20% Below List Price
  • $156/SF
  • 128 Days On Market

  Current Estimated Value $366,415

  Last Listing Agent John Bilancione Nicoli Realty

  7 Wilbur Ave, Middletown, NY 10940
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  Est $519,436 Not Listed For Sale

  4 Disco Dr, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 2,588 Sq Ft
  • Built 1975

  4 Disco Dr, Middletown, NY 10941

  Last Sold Summary

  • 14% Above List Price
  • $176/SF
  • 109 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Michelle Gruberger Real Estate Circuit Inc
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  /40

  $513,999 Pending

  • 3 Beds
  • 3 Baths
  • 2,696 Sq Ft

  2 Danielle Ct, Middletown, NY 10940

  Welcome to 2 Danielle Court, a stucco home on just over a half-acre in desirable Middletown, NY. This move-in ready property features 3 bedrooms, 3 bathrooms, and a versatile media room on the lower level. Enjoy an inviting layout filled with natural light, plus an expansive backyard with endless possibilities. Located in a quiet cul-de-sac with parking for up to 6 vehicles. Comes with a FREE

  Ravyn Green YourHomeSold Guaranteed Realty

  2 Danielle Ct, Middletown, NY 10940
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  /50

  $595,000 Sold Jul 21, 2025

  1 Wawayanda Place, Middletown, NY 10940

  • 5 Beds
  • 4 Baths
  • 3,890 Sq Ft
  • Built 1948

  Last Sold Summary

  • $153/SF
  • 2 Days On Market

  Current Estimated Value $603,266

  Last Listing Agent Jamie Sittner Find Advisors

  1 Wawayanda Place, Middletown, NY 10940
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  Est $519,415 Not Listed For Sale

  8 Rondack Rd, Middletown, NY 10941

  • 4 Beds
  • 3.5 Baths
  • 2,260 Sq Ft
  • Built 1987

  8 Rondack Rd, Middletown, NY 10941

  Last Sold Summary

  • 8% Above List Price
  • $213/SF
  • 39 Days On Market

  Last Sold Price $482,000

  Last Listing Agent Bethany Wager-Mckee Agnes I Wager Realty Inc.
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  /4

  $299,999 Pending

  • 4 Beds
  • 1 Bath
  • 1,316 Sq Ft

  86 Linden Ave, Middletown, NY 10940

  The possibilities are ENDLESS with this one. Come check out the biggest bang for your buck in Middletown. This is a 4 bedroom 1 bathroom house with TREMENDOUS potential. A FULL basement where you can have a blank canvas for a movie room or even a library/office. Maybe you're a first time home buyer who can bring your vision and your ideas to this one or you're an investor who's looking to

  Kewin Garabito eXp Realty

  86 Linden Ave, Middletown, NY 10940
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  $180,000 Sold Apr 23, 2025

  3 Fortune Rd W Unit H, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 775 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Above List Price
  • $232/SF
  • 15 Days On Market

  Last Listing Agent James LaTempa Compass Greater NY, LLC

  3 Fortune Rd W Unit H, Middletown, NY 10941
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  Est $464,482 Not Listed For Sale

  8 Frederick St, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,732 Sq Ft
  • Built 1984

  8 Frederick St, Middletown, NY 10941

  Last Sold Summary

  • 26% Above List Price
  • $213/SF
  • 32 Days On Market

  Last Sold Price $369,000

  Last Listing Agent Christina Wilger RE/MAX Benchmark Realty Group
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  /25

  $314,900

  • 3 Beds
  • 1.5 Baths
  • 1,528 Sq Ft

  21 N Aspen Rd, Middletown, NY 10940

  Move right into this well-maintained 3-bedroom, 2-bath townhouse located in the desirable Middletown School District. Major exterior upgrades completed in 2023, including a new roof, new siding, and new windows, giving buyers peace of mind for years to come. Inside, you’ll find updated flooring throughout, a functional layout, and gas heat (no oil). The fenced-in backyard and covered porch

  Derek Greene Greene Realty Group

  21 N Aspen Rd, Middletown, NY 10940
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  $340,000 Sold Dec 19, 2025

  8 Park Row, Middletown, NY 10941

  • 4 Beds
  • 1.5 Baths
  • 1,496 Sq Ft
  • Built 1965

  Last Sold Summary

  • 4% Above List Price
  • $227/SF
  • 27 Days On Market

  Current Estimated Value $314,801

  Last Listing Agent Vanessa Wight BHG Real Estate Green Team

  8 Park Row, Middletown, NY 10941
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  Est $454,402 Not Listed For Sale

  3 Frederick St, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1984

  3 Frederick St, Middletown, NY 10941

  Last Sold Summary

  • 20% Above List Price
  • $211/SF
  • 23 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Kerri Stretch Howard Hanna Rand Realty
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  /35

  $500,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,211 Sq Ft

  17 Magnolia Park Rd, Middletown, NY 10940

  Discover easy living in this beautifully maintained 3 bedroom, 2.5 bath townhouse located in the heart of Middletown! Offering three levels of comfortable space, this home features a bright main floor with gleaming hardwood floors, and open living and dining area, and a modern kitchen complete with granite countertops and ample cabinet space. Step outside to your private deck, perfect for morning

  Amy Rossi Howard Hanna Rand Realty

  17 Magnolia Park Rd, Middletown, NY 10940
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  $360,000 Sold Sep 19, 2025

  36 Karen Dr, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,436 Sq Ft
  • Built 1965

  Last Sold Summary

  • 5% Below List Price
  • $251/SF
  • 122 Days On Market

  Current Estimated Value $381,215

  Last Listing Agent Jason Madison eXp Realty

  36 Karen Dr, Middletown, NY 10940
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  Est $491,637 Not Listed For Sale

  1 Placid Ave, Middletown, NY 10941

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1987

  1 Placid Ave, Middletown, NY 10941

  Last Sold Summary

  • 13% Above List Price
  • $218/SF
  • 20 Days On Market

  Last Sold Price $435,000

  Last Listing Agent rosemary mcginn Century 21 Full Service Realty
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  /38

  $585,000 Pending

  • 3 Beds
  • 2 Baths
  • 4,240 Sq Ft

  83 Dosen Rd, Middletown, NY 10940

  Welcome to your private retreat, perfectly nestled on 4.6 scenic, park-like acres in the heart of the Pine Bush School District. This 1 owner home has 3 bedrooms 2 baths on 1st level, screened in porch off kitchen, enormous living room offers plenty of room for the whole family plus extended family and is ideal for those who love to entertain or simply enjoy the peaceful Hudson Valley lifestyle.

  Joseph Rubeo Keller Williams Hudson Valley

  83 Dosen Rd, Middletown, NY 10940
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  $269,000 Sold Apr 09, 2025

  51 Watkins Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,360 Sq Ft
  • Built 1908

  Last Sold Summary

  • 13% Below List Price
  • $198/SF
  • 133 Days On Market

  Current Estimated Value $282,728

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.

  51 Watkins Ave, Middletown, NY 10940
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  Est $280,050 Not Listed For Sale

  44 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  44 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 12% Above List Price
  • $174/SF
  • 35 Days On Market

  Last Sold Price $250,000

  Last Listing Agent Denise DePaola John J Lease REALTORS Inc
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  /20

  $153,000

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  529 5th Ave, Middletown, NY 10941

  Fantastic opportunity for a well loved 3 bedroom, 2 bathroom mobile home. Many upgrades AND a Generac Generator as well!!! Granite counters in the kitchen. Windows have all been replaced. Pex plumbing upgrades throughout. Central a/c. Ceiling fans all around the home and many windows for natural light. Primary bedroom has walk in closet and upgraded en-suite bathroom with big closet. Huge closets

  Dawn Barclay Century 21 Full Service Realty

  529 5th Ave, Middletown, NY 10941
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  $475,000 Sold Aug 21, 2025

  19 Woodrose Ct, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,890 Sq Ft
  • Built 2020

  Last Sold Summary

  • 6% Above List Price
  • $164/SF
  • 31 Days On Market

  Current Estimated Value $466,377

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

  19 Woodrose Ct, Middletown, NY 10940
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  Est $269,268 Not Listed For Sale

  62 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  62 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 12% Above List Price
  • $167/SF
  • 79 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Brian Phillips Douglas Elliman Real Estate
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  /31

  $319,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  22 Red Barn Ln, Middletown, NY 10940

  Welcome home to this beautifully renovated 3-bedroom, 2.5-bathroom move-in-ready townhouse, perfectly situated in the highly desirable Meadows development within the Middletown School District. Thoughtfully updated with a full gut renovation in 2020, this spacious home blends modern elegance with everyday comfort.Step inside and immediately feel at home. The main level offers a bright and

  Maria Sairrino Cronin & Company Real Estate

  22 Red Barn Ln, Middletown, NY 10940
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  $261,000 Sold Jun 27, 2025

  47 Liberty St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,232 Sq Ft
  • Built 1890

  Last Sold Summary

  • 4% Above List Price
  • $212/SF
  • 26 Days On Market

  Current Estimated Value $265,624

  Last Listing Agent Lynelle Alessi Keller Williams Hudson Valley

  47 Liberty St, Middletown, NY 10940
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  Est $297,604 Not Listed For Sale

  92 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1978

  92 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 1% Above List Price
  • $205/SF
  • 32 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Wenpeng Guan Keller Williams Hudson Valley
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  /3

  $115,000

  • Land
  • 2.1 Acres
  • $54,762 per Acre

  143 Shawangunk Rd, Middletown, NY 10941

  TWO lots available for $115,000 each. Zoned Highway Commercial, suitable for several commercial uses subject to site plan approval. Lot 1 is 2.1 acres. Lot 2 is 2.3 acres. Previously engineered but needs to be updated as part of the design process. Good location between exits 116 and 118 on NYS Rt 17/Quickway/Interstate 86 providing excellent interstate and highway access. High visibility.

  Richard (RJ) Smith Rand Commercial

  143 Shawangunk Rd, Middletown, NY 10941
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  $270,000 Sold Jan 05, 2026

  1538 Route 211 W, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,536 Sq Ft
  • Built 1920

  Last Sold Summary

  • 10% Below List Price
  • $176/SF
  • 68 Days On Market

  Current Estimated Value $306,052

  Last Listing Agent John Olivero Keller Williams Realty

  1538 Route 211 W, Middletown, NY 10940
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  Est $286,839 Not Listed For Sale

  122 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  122 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 2% Above List Price
  • $194/SF
  • 158 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Sandra Cotthaus 1st Independent Realty Grp
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  /8

  $90,000

  • Land
  • 5.37 Acres
  • $16,760 per Acre

  0 Basil Todd Rd, Middletown, NY 12430

  Over five acres of meadow, woods and Mountain View’s to build your dream home. Minutes to Belleayre to enjoy the outdoors. With inventory down, there isn’t any need to settle. We have access to local builders, engineers and contractors to help guide you through the process. Looking for more?? There is an adjacent five acre parcel also available. Seller may be willing to finance too.

  Heather Martin United RE Hudson Valley Edge

  0 Basil Todd Rd, Middletown, NY 12430
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  $531,500 Sold May 01, 2025

  25 Cyprus Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft
  • Built 2016

  Last Sold Summary

  • $285/SF
  • 50 Days On Market

  Current Estimated Value $555,319

  Last Listing Agent Mary Rice Israelski Howard Hanna Rand Realty

  25 Cyprus Dr, Middletown, NY 10940
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  Est $290,477 Not Listed For Sale

  5 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  5 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 4% Above List Price
  • $194/SF
  • 89 Days On Market

  Last Sold Price $280,000

  Last Listing Agent Melissa Trejo Weichert Realtors
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  /58

  $625,000 Pre-Foreclosure

  • 12 Beds
  • 10 Baths
  • 5,004 Sq Ft

  5 Wawayanda Place, Middletown, NY 10940

  CASH ONLY - Totally renovated large home with 12 bedrooms, 8 of them being suites with their own full bathroom. 10 full bathrooms total. Home also features game room, large dining area, living room, spacious eat in kitchen with stainless appliances & island, laundry off the kitchen, large fenced patio & inground pool. Conveniently located around Orange County Community College, tennis & skate and

  Jamie Sittner Find Advisors

  5 Wawayanda Place, Middletown, NY 10940
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  $380,000 Sold Feb 12, 2026

  48 Beacon St, Middletown, NY 10940

  • 6 Beds
  • 2 Baths
  • 2,738 Sq Ft
  • Built 1900

  Last Sold Summary

  • $139/SF
  • 9 Days On Market

  Current Estimated Value $394,457

  Last Listing Agent Kewin Garabito eXp Realty

  48 Beacon St, Middletown, NY 10940
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  Est $295,944 Not Listed For Sale

  53 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  53 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 8% Above List Price
  • $191/SF
  • 58 Days On Market

  Last Sold Price $275,000

  Last Listing Agent J Lewis Keller Williams Hudson Valley
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  /39

  $320,000

  • 5 Beds
  • 2 Baths

  16 Liberty St, Middletown, NY 10940

  Welcome to 16 Liberty Street, a charming home ideally located in the heart of Middletown. This inviting property offers a comfortable layout with bright living spaces and a warm, welcoming feel—perfect for everyday living or investment potential. Inside, you’ll find generously sized rooms, natural light throughout, and a flexible floor plan ready to accommodate your lifestyle. The outdoor space

  Minnie Thomas Keller Williams Hudson Valley

  16 Liberty St, Middletown, NY 10940

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