Middletown, NY Homes

• 

  $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 $367,581

  Last Listing Agent Jason Madison eXp Realty

  36 Karen Dr, Middletown, NY 10940
• 

  Est $499,604 Not Listed For Sale

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

  8 Rondack Rd, Middletown, NY 10941

  8 Rondack Rd, Middletown, NY 10941
• 

  

  

  /35

  $359,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  14 Knox Ave, Middletown, NY 10940

  Move Right In! Your Perfect Home Awaits! Welcome to this beautifully maintained home where comfort, space, and convenience come together. Step inside and immediately notice the fresh and clean sun drenched rooms that flow throughout, setting the tone for a home that’s been lovingly cared for. The spacious kitchen offers plenty of counter space and ample cabinets for all your cooking needs—ideal

  Chris Carbone HomeSmart Homes & Estates

  14 Knox Ave, Middletown, NY 10940
• 

  $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 $281,789

  Last Listing Agent Pedro Garcia Curasi Realty, Inc.

  51 Watkins Ave, Middletown, NY 10940
• 

  Est $437,474 Not Listed For Sale

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

  8 Frederick St, Middletown, NY 10941

  8 Frederick St, Middletown, NY 10941
• 

  

  /24

  $368,800 Pending

  • 4 Beds
  • 3 Baths
  • 1,505 Sq Ft

  8 Ebury Mews, Middletown, NY 10940

  Beautiful 4-Bedroom Home in Canterbury Knolls – Town of Wallkill Welcome to this spacious and beautifully maintained 4-bedroom, 3-bath detached home in the highly sought-after Canterbury Knolls community.This rare property is one of the largest models in the neighborhood, offering the perfect blend of comfort, privacy, and convenience. Tucked away at the end of a quiet cul-de-sac and bordered

  Jonathon Lee Keller Williams Hudson Valley

  8 Ebury Mews, Middletown, NY 10940
• 

  $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 $466,952

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

  19 Woodrose Ct, Middletown, NY 10940
• 

  Est $426,796 Not Listed For Sale

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

  3 Frederick St, Middletown, NY 10941

  3 Frederick St, Middletown, NY 10941
• 

  

  /22

  $220,000

  • 2 Beds
  • 1 Bath
  • 820 Sq Ft

  58 Wawayanda Ave, Middletown, NY 10940

  A Great Place to Call Home or perfect for those looking to expand your real estate investment portfolio, this charming Middletown home offers the perfect blend of comfort, convenience, and value. Cozy yet spacious, this home has been thoughtfully updated and is truly move-in ready! With 2 bedrooms, a full bath and a home office/ den you will have all the space you need. Enjoy peace of mind with

  Frank Muccari Cronin & Company Real Estate

  58 Wawayanda Ave, Middletown, NY 10940
• 

  $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 $270,487

  Last Listing Agent Lynelle Alessi Keller Williams Hudson Valley

  47 Liberty St, Middletown, NY 10940
• 

  Est $456,164 Not Listed For Sale

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

  1 Placid Ave, Middletown, NY 10941

  1 Placid Ave, Middletown, NY 10941
• 

  

  /41

  $440,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,848 Sq Ft

  4 Thistle Ln, Middletown, NY 10940

  Spacious & Versatile Raised Ranch in Prime Middletown Location! Not your average bi-level! This move-in-ready, raised-ranch-style home in Middletown, within the Minisink Valley School District, offers the perfect blend of convenience and comfort. Located near Garnet Medical Center, Crystal Run, shopping centers, supermarkets, and with easy access to Metro-North and major highways, it’s an ideal

  Soleil Jackman Howard Hanna Rand Realty

  4 Thistle Ln, Middletown, NY 10940
• 

  $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

  Last Listing Agent John Olivero Keller Williams Realty

  1538 Route 211 W, Middletown, NY 10940
• 

  Est $277,314 Not Listed For Sale

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

  44 Sarah Ln, Middletown, NY 10941

  44 Sarah Ln, Middletown, NY 10941
• 

  

  /26

  $329,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  136 & 140 Gillen Rd, Middletown, NY 10940

  Welcome to your affordable new home just off Route 17M! This charming 3-bedroom ranch offers incredible value that beats the recent appraisal. Enjoy the comfort of central A/C and peace of mind with a durable metal roof. The best part? The assumable lease on the solar panels delivers dramatically low electric bills, putting more money back in your pocket every month! The sale includes two

  Karie Boniface Cronin & Company Real Estate

  136 & 140 Gillen Rd, Middletown, NY 10940
• 

  $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 $561,872

  Last Listing Agent Mary Rice Israelski Howard Hanna Rand Realty

  25 Cyprus Dr, Middletown, NY 10940
• 

  Est $261,173 Not Listed For Sale

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

  62 Sarah Ln, Middletown, NY 10941

  62 Sarah Ln, Middletown, NY 10941
• 

  

  /33

  $375,000

  • 4 Beds
  • 2.5 Baths
  • 1,668 Sq Ft

  29 Little Ave, Middletown, NY 10940

  Discover this renovated colonial home nestled in the charming city of Middletown. This spacious single-family residence offers a perfect blend of classic charm and tasteful updates. The main level features a dedicated home office, an inviting living room, and an open-concept kitchen with stunning granite countertops and a center island. A formal dining room and a convenient half bath complete

  Michael LaMorte Christie's Int. Real Estate

  29 Little Ave, Middletown, NY 10940
• 

  $465,000 Sold Jul 14, 2025

  335 Shawangunk Rd, Middletown, NY 10940

  • 5 Beds
  • 3 Baths
  • 2,660 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Above List Price
  • $175/SF
  • 53 Days On Market

  Current Estimated Value $481,370

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty

  335 Shawangunk Rd, Middletown, NY 10940
• 

  Est $290,720 Not Listed For Sale

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

  92 Sarah Ln, Middletown, NY 10941

  92 Sarah Ln, Middletown, NY 10941
• 

  

  /32

  $375,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,608 Sq Ft

  5 Raleigh Close Unit 3, Middletown, NY 10940

  CANTERBURY KNOLLS of Wallkill now offers this GORGEOUS TURN-KEY Contemporary style home just waiting for the right owner to call it HOME. Freshly painted walls welcomes into an open floor concept living room followed by a dining area and a spacious kitchen with granite counters, beautiful backsplash and plenty of cabinet space. Brand new stainless steel kitchen appliances fresh out of the box.

  Sandra Arnez Keller Williams Hudson Valley

  5 Raleigh Close Unit 3, Middletown, NY 10940
• 

  $395,000 Sold Aug 28, 2025

  7 Randall Terrace, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,164 Sq Ft
  • Built 1953

  Last Sold Summary

  • 4% Below List Price
  • $339/SF
  • 53 Days On Market

  Current Estimated Value $393,282

  Last Listing Agent Desiree Beecham River Realty Services, Inc.

  7 Randall Terrace, Middletown, NY 10940
• 

  Est $277,398 Not Listed For Sale

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

  5 Sarah Ln, Middletown, NY 10941

  5 Sarah Ln, Middletown, NY 10941
• 

  

  /13

  $45,000

  • Land
  • 1.4 Acres
  • $32,143 per Acre

  Pocatello Road Pocatello Rd, Middletown, NY 10940

  Country Living. yet just ten minutes to Middletown NY. area of nice homes. over 249 feet county road frontage. no close neighbors private. Rt 17 Rt 24 Rt 35 all close by. for easy commute to work. Orange County is a leader in population and company relocating more jobs Avalible. five minutes to Maple Hill Elementary School zoned R2 with no water and no sewer one would need 3 Acres so this

  John Melchior Howard Hanna Rand Realty

  Pocatello Road Pocatello Rd, Middletown, NY 10940
• 

  $125,500 Sold Feb 14, 2025

  2607 State Route 17k, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,311 Sq Ft
  • Built 2009

  Last Sold Summary

  • 16% Below List Price
  • $96/SF
  • 79 Days On Market

  Last Listing Agent Carol Cruz Keller Williams Hudson Valley

  2607 State Route 17k, Middletown, NY 10941
• 

  Est $284,001 Not Listed For Sale

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

  53 Sarah Ln, Middletown, NY 10941

  53 Sarah Ln, Middletown, NY 10941
• 

  

  /11

  $150,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  55 Glen Ave, Middletown, NY 10940

  Single faming home in the wonderful Middletown, NY up for grabs. Needs renovation. This is a fixer-upper on a large .34 acre lot. Don't miss out.

  Ishwar Rameshar YourHomeSold Guaranteed Realty

  55 Glen Ave, Middletown, NY 10940
• 

  $140,000 Sold Dec 02, 2025

  228 Concord Ln Unit 228, Middletown, NY 10940

  • 1 Bed
  • 1 Bath
  • 740 Sq Ft
  • Built 1989

  Last Sold Summary

  • 2% Below List Price
  • $189/SF
  • 95 Days On Market

  Last Listing Agent Yasmine Delgado BHG Real Estate Green Team

  228 Concord Ln Unit 228, Middletown, NY 10940
• 

  Est $320,016 Not Listed For Sale

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

  57 Sarah Ln, Middletown, NY 10941

  57 Sarah Ln, Middletown, NY 10941
• 

  

  /24

  $329,900

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  9 Fairview Ave, Middletown, NY 10940

  A must see home! This beautiful colonial home will have everything brand new - from the exterior: roof, sidings, windows, porch, deck to the interior: kitchen, all walls with plumbing and electrical lines, kitchen with brand new cabinets, countertops and appliances: refrigerator, oven/range, microwave and dishwasher, beautiful bathrooms with tiles, hardwood floorings - all NEW. Featuring 3

  Anita S. Cristiano HomeSmart Homes & Estates

  9 Fairview Ave, Middletown, NY 10940
• 

  $210,000 Sold May 08, 2025

  57 Jimal Dr, Middletown, NY 10940

  • 1 Bed
  • 1 Bath
  • 893 Sq Ft
  • Built 1990

  Last Sold Summary

  • $235/SF
  • 128 Days On Market

  Current Estimated Value $219,184

  Last Listing Agent LIENA HAMDI Exit Realty Connections

  57 Jimal Dr, Middletown, NY 10940
• 

  Est $315,718 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 1,692 Sq Ft

  19 Red Barn Ln, Middletown, NY 10940

  19 Red Barn Ln, Middletown, NY 10940
• 

  

  /10

  $299,999

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

  328 Bloomingburg Rd, Middletown, NY 10940

  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. NO engineering

  Jeffrey Lyons Curasi Realty, Inc.

  328 Bloomingburg Rd, Middletown, NY 10940
• 

  $405,000 Sold Sep 26, 2025

  15 Rowan St Unit 13, Middletown, NY 10940

  • 5 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1900

  Last Sold Summary

  • 3% Below List Price
  • $211/SF
  • 16 Days On Market

  Current Estimated Value $397,679

  Last Listing Agent Juan Bautista Keller Williams Realty

  15 Rowan St Unit 13, Middletown, NY 10940
• 

  Est $296,236 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,452 Sq Ft

  40 Red Barn Ln, Middletown, NY 10940

  40 Red Barn Ln, Middletown, NY 10940
• 

  

  /13

  $268,000

  • 3 Beds
  • 1 Bath
  • 1,250 Sq Ft

  16 Woodland Rd, Middletown, NY 10940

  Welcome home to this nice three bedroom ranch located in the Minisink Valley School District in a quiet neighborhood! This private property is surrounded by nature with a large open yard to play and have fun in the sun. The large deck overlooks the private back yard and surrounding woods. The roof has been recently replaced. Sale includes an additional lot of 0.11 acres to bring the total

  Joseph Paoli Howard Hanna Rand Realty

  16 Woodland Rd, Middletown, NY 10940
• 

  $375,000 Sold Sep 12, 2025

  22 Maryland Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1920

  Last Sold Summary

  • 4% Below List Price
  • $260/SF
  • 80 Days On Market

  Current Estimated Value $369,980

  Last Listing Agent Patricia Lucey Picture It Sold, LLC

  22 Maryland Ave, Middletown, NY 10940
• 

  Est $303,747 Not Listed For Sale

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

  24 Black Stallion Ct, Middletown, NY 10940

  24 Black Stallion Ct, Middletown, NY 10940
• 

  /2

  $348,000

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft

  8 Hill Rd, Middletown, NY 10941

  Looking for a home you can make your own without breaking the bank? This 924 sq ft ranch style home on 4 private acres with direct Wallkill River access is a rare opportunity! This home needs some cleanup and finishing touches inside. You could move right in and update as you go! The Detached Garage needs a new roof and renovations. Perfect for FHA 203K buyers who want a little sweat equity and a

  Nancy LaBarbera Keller Williams Hudson Valley

  8 Hill Rd, Middletown, NY 10941
• 

  $305,000 Sold Apr 08, 2025

  11 Black Stallion Ct, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,188 Sq Ft
  • Built 1979

  Last Sold Summary

  • 2% Below List Price
  • $257/SF
  • 132 Days On Market

  Current Estimated Value $304,314

  Last Listing Agent Bente Brown John J Lease REALTORS Inc

  11 Black Stallion Ct, Middletown, NY 10940

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