Middletown, NY Homes

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  /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 Keller Williams Hudson Valley

  331 Highland Ave Extension, Middletown, NY 10940
• 

  $325,000 Sold Apr 28, 2026

  46 Silo Ln, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,452 Sq Ft
  • Built 1973

  Last Sold Summary

  • $224/SF
  • 20 Days On Market

  Current Estimated Value $322,105

  Last Listing Agent Jason Dillon eXp Realty

  46 Silo Ln, Middletown, NY 10940
• 

  Est $783,055 Not Listed For Sale

  427 Kirbytown Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 3,350 Sq Ft
  • Built 1999

  427 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 4% Above List Price
  • $224/SF
  • 110 Days On Market

  • Last Sold Price $750,000
  • Feb 22, 2024

  Last Listing Agent Kewin Garabito eXp Realty
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  /19

  $284,999 Pre-Foreclosure

  • 3 Beds
  • 2 Baths
  • 1,240 Sq Ft

  9 Genung St, Middletown, NY 10940

  Charming two-story home in the heart of Middletown! This spacious residence offers a welcoming front porch, perfect for relaxing evenings, and a practical layout filled with natural light. The home features multiple bedrooms, ample living space, and a generous yard with off-street parking. Located in a convenient neighborhood close to schools, shopping, dining, and major highways, this property

  Anthony Rivas Keller Williams Hudson Valley

  9 Genung St, Middletown, NY 10940
• 

  $575,000 Sold Jul 03, 2025

  5 Robert Burns Ct, Middletown, NY 10941

  • 6 Beds
  • 2 Baths
  • 2,448 Sq Ft
  • Built 1966

  Last Sold Summary

  • 4% Below List Price
  • $235/SF
  • 71 Days On Market

  Current Estimated Value $590,515

  Last Listing Agent Maria Sairrino Cronin & Company Real Estate

  5 Robert Burns Ct, Middletown, NY 10941
• 

  Est $612,270 Not Listed For Sale

  1053 Kirby Place, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,912 Sq Ft
  • Built 1986

  1053 Kirby Place, Middletown, NY 10940

  Last Sold Summary

  • 24% Above List Price
  • $169/SF
  • 75 Days On Market

  • Last Sold Price $493,000
  • Oct 25, 2023

  Last Listing Agent Tolga Erzene Keller Williams Rlty Integrity
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  /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
• 

  $380,000 Sold Feb 10, 2026

  7 Manhattan Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,550 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Above List Price
  • $245/SF
  • 46 Days On Market

  Current Estimated Value $368,421

  Last Listing Agent Darnell Williams R New York

  7 Manhattan Ave, Middletown, NY 10940
• 

  Est $696,923 Not Listed For Sale

  454 Kirbytown Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,721 Sq Ft
  • Built 1998

  454 Kirbytown Rd, Middletown, NY 10940

  Last Sold Summary

  • 10% Above List Price
  • $232/SF
  • 27 Days On Market

  • Last Sold Price $631,000
  • May 24, 2023

  Last Listing Agent Norberto Tirado N Tirado Realty LLC
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  /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 Keller Williams Hudson Valley

  255 Howells Rd, Middletown, NY 10940
• 

  $60,000 Sold Jan 26, 2026

  43 Clinton St, Middletown, NY 10940

  • Land
  • 5,000 Sq Ft
  • $522,648 per Acre

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Travis Thompson Keller Williams Hudson Valley

  43 Clinton St, Middletown, NY 10940
• 

  Est $449,929 Not Listed For Sale

  148 Camp Stadie Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,720 Sq Ft
  • Built 1959

  148 Camp Stadie Rd, Middletown, NY 10940

  Last Sold Summary

  • 6% Above List Price
  • $247/SF
  • 26 Days On Market

  • Last Sold Price $425,000
  • Oct 27, 2023

  Last Listing Agent Kathy Eubanks Keller Williams Realty
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  /9

  $675,000 Coming Soon

  • 4 Beds
  • 3 Baths
  • 4,080 Sq Ft

  225 Brown Rd, Middletown, NY 10941

  STUNNING 4-Bedroom, 3-Bathroom CONTEMPORARY LUXURY Home with Modern Upgrades. This turn-key beauty features a gorgeous updated eat-in kitchen with quartz countertops and an island, brand new stainless steel appliances fresh out the box, new cabinets a stylish backsplash with doors that lead to the back deck, perfect for entertaining. A formal fining room is followed by an oversized living room/

  Sandra Arnez Keller Williams Hudson Valley

  225 Brown Rd, Middletown, NY 10941
• 

  $402,000 Sold Jul 02, 2025

  34 Walnut Ln, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1991

  Last Sold Summary

  • 1% Above List Price
  • $349/SF
  • 26 Days On Market

  Current Estimated Value $410,362

  Last Listing Agent Laurel Lustgarten Howard Hanna Rand Realty

  34 Walnut Ln, Middletown, NY 10940
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  Est $466,727 Not Listed For Sale

  634 Pocatello Rd, Middletown, NY 10940

  • 4 Beds
  • Built 1880

  634 Pocatello Rd, Middletown, NY 10940

  Last Sold Summary

  • 17% Above List Price
  • $163/SF
  • 185 Days On Market

  • Last Sold Price $400,000
  • Feb 15, 2024

  Last Listing Agent Bryan Dale eXp Realty
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  /26

  $479,900

  • 2 Beds
  • 2.5 Baths
  • 1,762 Sq Ft

  15 High Ridge Ln, Middletown, NY 10940

  Welcome to this impeccably maintained center-unit townhouse in the desirable Fairways at Wallkill, a gated community known for its convenience and low-maintenance lifestyle. This two-bedroom, two-full bath and one-half bath home offers a clean, modern interior with nothing to update. The main level features an open layout with gleaming hardwood floors, neutral tones, and abundant natural light

  Patricia Sassi RE/MAX Benchmark Realty Group

  15 High Ridge Ln, Middletown, NY 10940
• 

  $360,000 Sold Nov 07, 2025

  55 Prince St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,537 Sq Ft
  • Built 1893

  Last Sold Summary

  • 16% Above List Price
  • $234/SF
  • 36 Days On Market

  Current Estimated Value $356,626

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  55 Prince St, Middletown, NY 10940
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  Est $500,625 Not Listed For Sale

  661 Pocatello Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,304 Sq Ft
  • Built 1986

  661 Pocatello Rd, Middletown, NY 10940

  Last Sold Summary

  • 18% Above List Price
  • $184/SF
  • 49 Days On Market

  • Last Sold Price $424,000
  • Sep 16, 2024

  Last Listing Agent Christian Baez Keller Williams Hudson Valley
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  /32

  $399,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,724 Sq Ft

  2 Thomas Jefferson Place, Middletown, NY 10940

  Welcome to easy living in the heart of Middletown! This maintained 3-bedroom, 1,700-square-foot ranch sits proudly on a desirable corner parcel, offering both space and convenience in one of the city’s most accessible locations. Designed for effortless one-floor living, this home offers a comfortable, flowing layout that’s perfect for everyday life and gatherings alike. The living room invites

  Patricia Sassi RE/MAX Benchmark Realty Group

  2 Thomas Jefferson Place, Middletown, NY 10940
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  $155,000 Sold Sep 18, 2025

  268 Concord Ln, Middletown, NY 10940

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

  Last Sold Summary

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

  Current Estimated Value $157,444

  Last Listing Agent Chris Cardinal Keller Williams Realty

  268 Concord Ln, Middletown, NY 10940
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  Est $288,998 Not Listed For Sale

  168 Camp Stadie Rd, Middletown, NY 10940

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1961

  168 Camp Stadie Rd, Middletown, NY 10940

  Last Sold Summary

  • 5% Above List Price
  • $275/SF
  • 201 Days On Market

  • Last Sold Price $275,000
  • Apr 18, 2025

  Last Listing Agent Ann Marie D'Onofrio Briante Realty Group, LLC
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  /13

  $290,000

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  3 Top Notch Rd, Middletown, NY 10940

  This ranch-style home sits on a sizable lot with a practical single-level floor plan. The property offers potential and solid foundation for the right buyer. The property sits on a secluded wooded lot with mature evergreen borders that create natural privacy year-round. The private wooded backyard provides a peaceful retreat with considerable potential for outdoor activities and relaxation. A

  Andrea Rose Keller Williams Hudson Valley

  3 Top Notch Rd, Middletown, NY 10940
• 

  $370,000 Sold Aug 26, 2025

  34 Pine Ct, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,358 Sq Ft
  • Built 1971

  Last Sold Summary

  • 1% Below List Price
  • $157/SF
  • 6 Days On Market

  Current Estimated Value $404,528

  Last Listing Agent Frank Tangredi Frank Tangredi Realty Company

  34 Pine Ct, Middletown, NY 10941
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  Est $464,297 Not Listed For Sale

  15 Milo Dr, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,152 Sq Ft
  • Built 1992

  15 Milo Dr, Middletown, NY 10941

  Last Sold Summary

  • 11% Above List Price
  • $195/SF
  • 24 Days On Market

  • Last Sold Price $420,000
  • Aug 22, 2023

  Last Listing Agent Kirk German HomeSmart Homes & Estates
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  /2

  $40,000

  • 550 Sq Ft

  40 Ivory Ln, Middletown, NY 10940

  SPACIOUS LAND AVAILABLE FOR SALE IN DESIRABLE AREA OF MIDDLETOWN NY

  ALISON NIXON eXp Realty

  40 Ivory Ln, Middletown, NY 10940
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  $480,000 Sold Dec 05, 2025

  95 Rolling Meadows Rd, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,055 Sq Ft
  • Built 1979

  Last Sold Summary

  • 5% Above List Price
  • $234/SF
  • 14 Days On Market

  Current Estimated Value $478,659

  Last Listing Agent Kevin Grier Keller Williams Hudson Valley

  95 Rolling Meadows Rd, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit G2, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit G2, Middletown, NY 10941

  Last Sold Summary

  • $204/SF
  • 25 Days On Market

  • Last Sold Price $232,000
  • Oct 13, 2023

  Last Listing Agent Deniece Carter Curasi Realty, Inc.
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  /19

  $479,999 Pending

  • 6 Beds
  • 2 Baths
  • 2,424 Sq Ft

  80 Prospect Ave, Middletown, NY 10940

  Welcome to 80 Prospect Ave, a well-maintained six-bedroom, two-bathroom home situated in the peaceful suburban setting of Middletown, NY. Built in 1918, this 2,424 square foot residence combines traditional architectural charm with modern updates, offering nearly 6,800 square feet of usable lot space ideal for both living and outdoor enjoyment. The property features a classic two-story design

  Jonathan Paredes Locqube New York, Inc.

  80 Prospect Ave, Middletown, NY 10940
• 

  $338,500 Sold Nov 26, 2025

  12 Columbine Ct, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 1,408 Sq Ft
  • Built 1979

  Last Sold Summary

  • 1% Above List Price
  • $240/SF
  • 33 Days On Market

  Current Estimated Value $338,717

  Last Listing Agent Christina Gilligan HomeSmart Homes & Estates

  12 Columbine Ct, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit A6, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit A6, Middletown, NY 10941

  Last Sold Summary

  • $224/SF
  • 18 Days On Market

  • Last Sold Price $255,000
  • Mar 08, 2024

  Last Listing Agent Feng Chang Acer Realty Inc
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  /12

  $260,000

  • 2 Beds
  • 1 Bath
  • 802 Sq Ft

  11 Philcox Rd, Middletown, NY 10940

  Rare opportunity to own two homes next door to each other in the Pine Bush School District. Single family home 2 bed, 1 bath, recently updated. Quiet road with only two homes, both originally owned by the same family, offering privacy and flexibility. Conveniently located near shopping, dining, train service, Resorts World Catskills, Kartrite Waterpark, and Bethel Woods Center for the Arts. Easy

  Joseph Rubeo Keller Williams Hudson Valley

  11 Philcox Rd, Middletown, NY 10940
• 

  $525,000 Sold Apr 10, 2026

  3 Ben Lomond Dr, Middletown, NY 10941

  • 5 Beds
  • 2 Baths
  • 2,515 Sq Ft
  • Built 1975

  Last Sold Summary

  • $209/SF
  • 19 Days On Market

  Current Estimated Value $515,073

  Last Listing Agent Joseph Rubeo Keller Williams Hudson Valley

  3 Ben Lomond Dr, Middletown, NY 10941
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  Not Listed For Sale

  100 Hillside Dr Unit C1, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit C1, Middletown, NY 10941

  Last Sold Summary

  • $171/SF
  • 19 Days On Market

  • Last Sold Price $195,000
  • Oct 31, 2023

  Last Listing Agent Linda Clark Hudson Valley Griffith
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  /44

  $299,999 Open Sat 10:30AM - 12:30PM

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft

  54 Whitman Ct, Middletown, NY 10941

  Welcome home—a move-in ready 3-bedroom, 1.5-bath townhouse located in a quiet cul-de-sac within the Pine Bush School District. With NO HOA fees, this is an incredible opportunity for buyers seeking low-maintenance living without the added monthly costs.This well-maintained home offers a functional and inviting layout, perfect for everyday living and entertaining. The kitchen and dining area

  Jennifer Lappe Keller Williams Realty

  54 Whitman Ct, Middletown, NY 10941
• 

  $440,000 Sold Apr 14, 2026

  35 East Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,939 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $227/SF
  • 26 Days On Market

  Current Estimated Value $435,762

  Last Listing Agent Gail Rachlin Keller Williams Hudson Valley

  35 East Ave, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit B9, Middletown, NY 10941

  • 1 Bed
  • 1 Bath
  • 917 Sq Ft
  • Built 1987

  100 Hillside Dr Unit B9, Middletown, NY 10941

  Last Sold Summary

  • $191/SF
  • 10 Days On Market

  • Last Sold Price $175,000
  • Dec 13, 2023

  Last Listing Agent Christina Rowan Howard Hanna Rand Realty
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  /22

  $329,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,400 Sq Ft

  26 Ridge St, Middletown, NY 10940

  Beautifully renovated single-family home offering a clean, comfortable layout with thoughtful updates throughout. This residence features 3 spacious bedrooms filled with natural light and a brand-new kitchen equipped with appliances and ample cabinetry. Fresh finishes throughout the home create a bright, move-in-ready feel. Enjoy additional storage space in both the attic and basement, providing

  Cheskel Werzberger Blooming Realty

  26 Ridge St, Middletown, NY 10940
• 

  $328,000 Sold Feb 03, 2026

  24 Kent Ct, Middletown, NY 10940

  • 2 Beds
  • 2.5 Baths
  • 1,241 Sq Ft
  • Built 1992

  Last Sold Summary

  • 1% Above List Price
  • $264/SF
  • 30 Days On Market

  Current Estimated Value $328,947

  Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

  24 Kent Ct, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit G16, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Built 1987

  100 Hillside Dr Unit G16, Middletown, NY 10941

  Last Sold Summary

  • $241/SF
  • 23 Days On Market

  • Last Sold Price $275,000
  • Sep 30, 2024

  Last Listing Agent Juan Bautista Serhant LLC
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  /3

  $350,000

  • Land
  • 1.42 Acres
  • $245,752 per Acre

  65 James P Kelly Way, Middletown, NY 10940

  Great location for a business. C-3 Zoning allows for any business, commercial or residential mix use. 262 feet frontage. Annual Average Daily Traffic (AADT) for 2023 is 10,569. There was a pre-approved building plan for a doctor's office building. The land is in the city of Middletown. The city will provide water and sewer. C-3 allow for 6 story mix-use business and residential building with the

  Jonathon Lee Keller Williams Hudson Valley

  65 James P Kelly Way, Middletown, NY 10940

Showing Results 401 - 440, Page 11 of 18