Middletown, NY Homes

• 

  

  

  /22

  $409,500

  $16K PRICE DROP

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

  19 Putters Way Unit 9, Middletown, NY 10940

  Welcome to this fully updated, move-ready condo in the desirable Walkill community. This splendid duplex has been luxuriously 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

  Abraham Lefkowitz Access Realty Team Inc

  19 Putters Way Unit 9, Middletown, NY 10940
• 

  $440,000

  Sold Jun 07, 2026

  47 Liberty St, Middletown, NY 10940

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

  Last Sold Summary

  • 1% Above List Price
  • $357/SF
  • 18 Days On Market

  Current Estimated Value $382,740

  Last Listing Agent Jonathon Lee KW Hudson Valley United

  47 Liberty St, Middletown, NY 10940
• 

  Est $380,948

  Not Listed For Sale

  5 Abingdon Mews, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • Built 1999

  5 Abingdon Mews, Middletown, NY 10940

  Last Sold Summary

  • 34 Days On Market
• 

  

  

  /23

  $399,999

  • 5 Beds
  • 2 Baths
  • 1,664 Sq Ft

  341 Highland Ave Extension, Middletown, NY 10940

  Welcome to 341 Highland Ave Ext, a bright and airy 4-bedroom, 2-bath split-level home conveniently situated in the heart of town. An inviting open floor plan creates effortless flow throughout the main living spaces, offering comfort, style, and plenty of natural light. Enjoy a level, fenced-in backyard—ideal for outdoor gatherings or peaceful relaxation. With local eateries, shopping, and daily

  Valerie Jewis Keller Williams Realty

  341 Highland Ave Extension, Middletown, NY 10940
• 

  $436,000

  Sold Apr 24, 2026

  227 Deer Ct Dr, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,919 Sq Ft
  • Built 1991

  Last Sold Summary

  • 7% Above List Price
  • $227/SF
  • 22 Days On Market

  Current Estimated Value $424,057

  Last Listing Agent Jie Liu KW Hudson Valley United

  227 Deer Ct Dr, Middletown, NY 10940
• 

  Est $348,666

  Not Listed For Sale

  3 Agin Court Square, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,405 Sq Ft
  • Built 1985

  3 Agin Court Square, Middletown, NY 10940

  Last Sold Summary

  • 40 Days On Market
• 

  

  /12

  $210,000

  Pending Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft

  8 Grant St, Middletown, NY 10940

  Here's the opportunity investors have been waiting for. This two-story colonial offers the right buyer a full-renovation canvas with real upside. Generous room sizes, hardwood floors on the upper level, a covered front porch, and an oversized barn/garage outbuilding in the rear — features that support strong ARV whether you're flipping or holding for rental income. The home needs a complete

  Igor Krasnoperov Rising Star Realty

  8 Grant St, Middletown, NY 10940
• 

  $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 $332,741

  Last Listing Agent Vanessa Wight BHG Real Estate Green Team

  8 Park Row, Middletown, NY 10941
• 

  Est $378,940

  Not Listed For Sale

  2 Manor Mews, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,625 Sq Ft
  • Built 1987

  2 Manor Mews, Middletown, NY 10940

  Last Sold Summary

  • 22 Days On Market
• 

  

  /18

  $55,000

  • Land
  • 5.26 Acres
  • $10,456 per Acre

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940

  Near the end of a quiet town-maintained dead-end road, you’ll find this ideal building lot in the town of Fleischmanns. This parcel has a mix of evergreens, deciduous trees, open clearings, and a seasonal stream, most of which is on level terrain ideal for a driveway and building site. Enjoy the peace and tranquility of a wooded sanctuary just minutes up the hill from the happening main street of

  Peter Kleeman Listing by Jewett and Jewett LLC

  

  0 Joe Todd Rd Unit R1680388, Middletown, NY 10940
• 

  $538,900

  Sold Mar 31, 2026

  4 Wayne Ct, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,404 Sq Ft
  • Built 2004

  Last Sold Summary

  • $224/SF
  • 33 Days On Market

  Current Estimated Value $540,337

  Last Listing Agent Antoinette Gundersen HomeSmart Homes & Estates

  4 Wayne Ct, Middletown, NY 10941
• 

  Est $368,241

  Not Listed For Sale

  8 Marsham Ct, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1985

  8 Marsham Ct, Middletown, NY 10940

  Last Sold Summary

  • 22 Days On Market
• 

  

  /12

  $65,000

  $10K PRICE INCREASE

  • Land
  • 7,875 Sq Ft
  • $359,513 per Acre

  538 E Main St, Middletown, NY 10940

  Residential land avaiable on East Main Street, close to the Crystal Medical center, close to NYS HWY 17, close to the Galleria Mall, close to the new Resorts and Casino about 30 milles away, close to the Poconos, come built you new home here.

  Frank Rivera Hudson Valley Home Connection

  538 E Main St, Middletown, NY 10940
• 

  $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 $372,537

  Last Listing Agent Jason Madison eXp Realty

  36 Karen Dr, Middletown, NY 10940
• 

  Est $365,296

  Not Listed For Sale

  2 Charlotte Mews, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,470 Sq Ft
  • Built 1985

  2 Charlotte Mews, Middletown, NY 10940

  Last Sold Summary

  • 27 Days On Market
• 

  

  /47

  $1,249,000

  • 3 Beds
  • 2.5 Baths
  • 4,225 Sq Ft

  2 White Horse Rd, Middletown, NY 10940

  Offered for sale for the very first time by its original owners, this custom-designed and thoughtfully upgraded 3-bedroom, 2.5-bath private luxury estate is nestled on 12.7 level acres in the Town of Greenville. Built in 2014 with quality craftsmanship and comfort in mind, this expansive home offers the perfect blend of space, functionality, and modern efficiency. The chef’s kitchen outfitted

  Vanessa Wight BHG Real Estate Green Team

  2 White Horse Rd, 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 $488,204

  Last Listing Agent Debbie Goldstein Howard Hanna Rand Realty

  19 Woodrose Ct, Middletown, NY 10940
• 

  Est $366,321

  Not Listed For Sale

  9 Harcourt Mews, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Built 1985

  9 Harcourt Mews, Middletown, NY 10940

  Last Sold Summary

  • 37 Days On Market
• 

  

  /50

  $310,000

  Coming Soon

  • 3 Beds
  • 1.5 Baths
  • 1,398 Sq Ft

  4 Lincoln St, Middletown, NY 10940

  This 3-bedroom, 2-bath Colonial offers 1,398 square feet of comfortable living space on a 0.11-acre lot. Built in 1890, the home blends timeless style with thoughtful upgrades while keeping its original charm. Enjoy bright mornings with natural light, cozy evenings at home, and a neighborhood close to shopping, restaurants, parks, schools, and local services. All utilities are available, making

  Matthew Gibbs KW Hudson Valley United

  4 Lincoln St, 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

  Current Estimated Value $299,744

  Last Listing Agent John Olivero Keller Williams Realty

  1538 Route 211 W, Middletown, NY 10940
• 

  Est $361,546

  Not Listed For Sale

  4 Marsham Ct, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1985

  4 Marsham Ct, Middletown, NY 10940

  Last Sold Summary

  • 68 Days On Market
• 

  

  /46

  $550,000

  • 4 Beds
  • 2.5 Baths
  • 2,069 Sq Ft

  16 Houston Ext Ave, Middletown, NY 10940

  Welcome to this beautiful, young Colonial, built in 2016 and ideally situated on a quiet street of newer homes in Middletown. Offering 4 spacious bedrooms and 2.5 bathrooms, this move-in-ready property seamlessly combines modern convenience with timeless style. The main level features gleaming hardwood floors, complemented by durable tile in the kitchen, half bath, and garage entry. Designed for

  Karleen Jedziniak Howard Hanna Rand Realty

  16 Houston Ext Ave, Middletown, NY 10940
• 

  $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 $379,526

  Last Listing Agent Kewin Garabito eXp Realty

  48 Beacon St, Middletown, NY 10940
• 

  Est $366,672

  Not Listed For Sale

  6 Saint Stephens Close, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft
  • Built 1985

  6 Saint Stephens Close, Middletown, NY 10940

  Last Sold Summary

  • 45 Days On Market
• 

  

  /22

  $318,000

  • 3 Beds
  • 2.5 Baths
  • 1,345 Sq Ft

  9 Jordan Ln, Middletown, NY 10940

  Welcome to easy townhouse living in Mountainside Hills, Middletown! This lovely 3 bedroom, 2.5 bath home offers comfort, space, and convenience. The main level features a spacious living room, formal dining area with hardwood floors, powder room and laundry room. The spacious eat-in kitchen is equipped with stainless steel appliances, along with elegant granite countertops. Upstairs, you'll find

  Bonnie Natt Realty Promotions Inc

  9 Jordan Ln, Middletown, NY 10940
• 

  $510,000

  Sold Mar 27, 2026

  13-15 Phillips St, Middletown, NY 10940

  • 4 Beds
  • 2 Baths
  • 1,901 Sq Ft
  • Built 1880

  Last Sold Summary

  • 2% Above List Price
  • $268/SF
  • 38 Days On Market

  Current Estimated Value $399,423

  Last Listing Agent Jason Nadeau Compass Greater NY, LLC

  13-15 Phillips St, Middletown, NY 10940
• 

  Est $354,052

  Not Listed For Sale

  4 Allan Park Mews, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 1985

  4 Allan Park Mews, Middletown, NY 10940

  Last Sold Summary

  • 27 Days On Market
• 

  

  /58

  $575,000

  • 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
• 

  $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 $480,179

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty

  335 Shawangunk Rd, Middletown, NY 10940
• 

  Est $365,203

  Not Listed For Sale

  2 Allan Park Mews, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft
  • Built 1985

  2 Allan Park Mews, Middletown, NY 10940

  Last Sold Summary

  • 31 Days On Market
• 

  

  /26

  $259,000

  Pending

  • 1 Bed
  • 1.5 Baths
  • 960 Sq Ft

  331 Highland Ave Extension, Middletown, NY 10940

  Tucked away on approximately .40 peaceful acres in the Town of Wallkill, just outside the City of Middletown, 331 Highland Ave Ext offers the perfect blend of charm, comfort, and affordability. Located in the Middletown School District, this lovingly maintained 2-story home features just under 1,000 square feet of bright and inviting living space, along with a spacious approximately

  Amanda Brehm KW Hudson Valley United

  331 Highland Ave Extension, 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 $387,292

  Last Listing Agent Desiree Beecham River Realty Services, Inc.

  7 Randall Terrace, Middletown, NY 10940
• 

  Est $361,145

  Not Listed For Sale

  3 Langton Mews, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,725 Sq Ft
  • Built 1985

  3 Langton Mews, Middletown, NY 10940

  Last Sold Summary

  • 36 Days On Market
• 

  

  /3

  $275,000

  Pending Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,604 Sq Ft

  7 Harcourt Mews, Middletown, NY 10940

  What a Great Investment Opportunity !! Spacious 3 Bedroom home in one of the most convenient and desirable locationsin the Town of Wallkill. This home features a Living Room, Kitchen, Lavatory, 3 Bedrooms and a Full Bathroom. this Home needs work !! Needs Renovation Home HOME HAS MOLD ENTER AT YOUR OWN RISK HEALTH HAZARD .HOME HAS GREAT POTENTIAL Wonderful Location.

  John Biasi Howard Hanna Rand Realty

  7 Harcourt Mews, Middletown, NY 10940
• 

  $426,500

  Sold Jan 22, 2026

  242 Derby Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 2,214 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Above List Price
  • $193/SF
  • 41 Days On Market

  Current Estimated Value $422,721

  Last Listing Agent Isaiah Lopez KW Hudson Valley United

  242 Derby Rd, Middletown, NY 10940
• 

  Est $476,144

  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

  • 31 Days On Market
• 

  

  /42

  $625,000

  Pending

  • 2 Beds
  • 3 Baths
  • 2,975 Sq Ft

  24 Juniper Cir, Middletown, NY 10940

  WELCOME TO WILDFLOWER AT WALLKILL — Orange County's premier 55+ Community! This elegant Tarrington model offers nearly 3,000 square feet of beautifully designed living space, combining comfort, sophistication, and convenience. Inside, you’ll find an open dining and living room combination creates the perfect flow for gatherings, while the expansive kitchen and family room with cathedral ceilings

  Patricia Sassi RE/MAX Benchmark Realty Group

  24 Juniper Cir, 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

  Current Estimated Value $146,777

  Last Listing Agent Yasmine Delgado BHG Real Estate Green Team

  228 Concord Ln Unit 228, Middletown, NY 10940
• 

  Est $495,594

  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

  • 109 Days On Market
• 

  

  /38

  $979,900

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas

  Jonathon Lee KW Hudson Valley United

  255 Howells Rd, Middletown, NY 10940

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