Middletown, NY Homes

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  $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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  $206,000 Sold Sep 10, 2025

  354 Concord Ln, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 2023

  Last Sold Summary

  • 6% Below List Price
  • $223/SF
  • 208 Days On Market

  Current Estimated Value $209,548

  Last Listing Agent Zhiheng Tang Keller Williams Hudson Valley

  354 Concord Ln, Middletown, NY 10940
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  Est $279,434 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  36 Poplar Ln, Middletown, NY 10941

  36 Poplar Ln, Middletown, NY 10941
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  $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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  $375,000 Sold Sep 22, 2025

  12 Eisenhower Dr, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,150 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Above List Price
  • $326/SF
  • 49 Days On Market

  Current Estimated Value $375,444

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  12 Eisenhower Dr, Middletown, NY 10940
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  Est $412,114 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,796 Sq Ft

  21 Crane Rd, Middletown, NY 10941

  21 Crane Rd, Middletown, NY 10941
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  $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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  $406,000 Sold May 13, 2025

  45 Sunrise Dr, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,478 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Above List Price
  • $275/SF
  • 25 Days On Market

  Current Estimated Value $415,549

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  45 Sunrise Dr, Middletown, NY 10940
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  Est $306,714 Not Listed For Sale

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

  46 Chaucer Ct, Middletown, NY 10941

  46 Chaucer Ct, Middletown, NY 10941
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  /40

  $409,999 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  2729 W Conkling Ave, Middletown, NY 10940

  Welcome to your next home at 29 W Conkling Avenue, located in the heart of Middletown. This charming 3 bedroom ranch-style residence offers many upgrades including updated kitchen with stainless steel appliances, hardwood floors, recessed lighting, solar panels, and a spacious walkout basement that dramatically expands your livable space. Enjoy the level double-lot backyard perfect for relaxing,

  Amanda Rivera Sepulveda Keller Williams Realty

  2729 W Conkling Ave, Middletown, NY 10940
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  $450,000 Sold Dec 09, 2025

  17 Pine Ct, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,561 Sq Ft
  • Built 1965

  Last Sold Summary

  • 3% Above List Price
  • $288/SF
  • 20 Days On Market

  Last Listing Agent Lauren Iacono Corcoran Baer & McIntosh

  17 Pine Ct, Middletown, NY 10941
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  Est $298,874 Not Listed For Sale

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

  16 Whitman Ct, Middletown, NY 10941

  16 Whitman Ct, Middletown, NY 10941
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  /23

  $359,000

  • 2 Beds
  • 1.5 Baths
  • 1,115 Sq Ft

  14 Kensington Way, Middletown, NY 10940

  Welcome to this beautifully renovated townhouse-style condo offering 2 bedrooms and 1.5 bathrooms. The bright, open-concept kitchen features brand-new appliances and flows seamlessly into a spacious living room filled with natural light from the sliding glass doors. Step outside to a private backyard patio—perfect for relaxing or entertaining. Upstairs, you’ll find two well-designed bedrooms,

  Xiaohui Cui Keller Williams Hudson Valley

  14 Kensington Way, Middletown, NY 10940
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  $325,000 Sold Mar 06, 2025

  Unlisted Address

  • 6 Beds
  • 4 Baths
  • 2,932 Sq Ft
  • Built 2006

  Last Sold Summary

  • 19% Below List Price
  • $111/SF
  • 157 Days On Market

  Current Estimated Value $396,393

  Last Listing Agent Danielle Reese Christie's Int. Real Estate

  Unlisted Address
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  Est $267,592 Not Listed For Sale

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

  18 Chaucer Ct, Middletown, NY 10941

  18 Chaucer Ct, Middletown, NY 10941
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  $405,000

  • 3 Beds
  • 2.5 Baths
  • 1,540 Sq Ft

  23 Peach Place, Middletown, NY 10940

  Welcome to this three-level townhouse located in Middletown, offering a one-car garage. The main level features a bright living room, with the kitchen and dining area located just beyond. The kitchen offers stainless steel appliances and plenty of cabinet and counter space. The refrigerator, microwave, and dryer were replaced in 2022. Sliding glass doors lead to a deck overlooking the yard. A

  Jie Liu Keller Williams Hudson Valley

  23 Peach Place, Middletown, NY 10940
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  $539,580 Sold Jul 07, 2025

  15 Roberts St, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 3,552 Sq Ft
  • Built 1900

  Last Sold Summary

  • 2% Above List Price
  • $152/SF
  • 90 Days On Market

  Current Estimated Value $549,587

  Last Listing Agent Jeanmarie Valentin HomeSmart Homes & Estates

  15 Roberts St, Middletown, NY 10940
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  Est $293,435 Not Listed For Sale

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

  18 Shelley Ct, Middletown, NY 10941

  18 Shelley Ct, Middletown, NY 10941
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  $399,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,652 Sq Ft

  21 California Dr, Middletown, NY 10940

  Home Is Where the Heart Is , and This One Has Plenty to Give!Welcome to 21 California Drive, a cherished family home that has been lovingly cared for and is ready for its next chapter. Spotless and exceptionally well maintained, this beautiful property will not last long.This charming split-level gem is nestled in the Town of Walkill, a true commuter’s dream within the highly sought-after

  Frank Muccari Cronin & Company Real Estate

  21 California Dr, Middletown, NY 10940
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  $295,000 Sold Aug 25, 2025

  6 Whitman Ct, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft
  • Built 1975

  Last Sold Summary

  • $195/SF
  • 28 Days On Market

  Current Estimated Value $298,071

  Last Listing Agent Gen Cheung River Realty Services, Inc.

  6 Whitman Ct, Middletown, NY 10941
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  Est $289,618 Not Listed For Sale

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

  42 Whitman Ct, Middletown, NY 10941

  42 Whitman Ct, Middletown, NY 10941
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  /22

  $279,999 Pending

  • 3 Beds
  • 1 Bath
  • 1,340 Sq Ft

  356 Sands Rd, Middletown, NY 10941

  This charming, updated home is an idyllic private retreat on over two acres of wooded land. Move-in ready, the house features fresh paint and new flooring throughout. The cozy living room provides ample natural lighting and leads right into the modern kitchen and dining area. The home offers three comfortable bedrooms and one full bathroom. Step outside to explore your own expansive wooded

  Samantha McCrory Exit Realty Connections

  356 Sands Rd, Middletown, NY 10941
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  $460,000 Sold Jul 29, 2025

  9 Laddie Rd, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,632 Sq Ft
  • Built 1971

  Last Sold Summary

  • 5% Above List Price
  • $282/SF
  • 28 Days On Market

  Current Estimated Value $457,930

  Last Listing Agent Bonnie Natt Realty Promotions Inc

  9 Laddie Rd, Middletown, NY 10941
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  Est $308,549 Not Listed For Sale

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

  36 Whitman Ct, Middletown, NY 10941

  36 Whitman Ct, Middletown, NY 10941
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  $90,000

  • 1 Bath
  • 480 Sq Ft

  115 Concord Ln Unit 115, Middletown, NY 10940

  Looking for an affordable and convenient place to call home? This bright studio condo in the desirable Buttonwood Estates community offers comfort and value in one package! Features include a galley-style kitchen, open living/sleeping area, and low-maintenance living—perfect for first-time buyers, downsizers, or investors. Enjoy the benefits of a well-kept community close to shopping, dining, and

  Malik Subhani Weichert Realtors

  115 Concord Ln Unit 115, Middletown, NY 10940
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  $450,000 Sold Oct 07, 2025

  853 Winterton Rd, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 2,108 Sq Ft
  • Built 1930

  Last Sold Summary

  • 33% Above List Price
  • $213/SF
  • 41 Days On Market

  Last Listing Agent Amanda Brehm Keller Williams Hudson Valley

  853 Winterton Rd, Middletown, NY 10940
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  Est $429,846 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,904 Sq Ft

  44 Crane Rd, Middletown, NY 10941

  44 Crane Rd, Middletown, NY 10941
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  $599,900

  • 4 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  458 County Route 50, Middletown, NY 10940

  Welcome to 458 County Route 50!Discover the perfect blend of elegance and functionality in this stunning colonial residence nestled in the highly sought-after Goshen School District. This expansive 2,200 sq. ft. home boasts 4 spacious bedrooms, 2.5 bathrooms, and a finished basement, complete with a one-car garage.Upon entering, you'll be greeted by an open floor plan featuring rich oak

  Travis Thompson Keller Williams Hudson Valley

  458 County Route 50, Middletown, NY 10940
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  $445,000 Sold May 06, 2025

  55 Liberty St, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,640 Sq Ft
  • Built 1928

  Last Sold Summary

  • $169/SF
  • 53 Days On Market

  Current Estimated Value $445,566

  Last Listing Agent Sandra Arnez Keller Williams Hudson Valley

  55 Liberty St, Middletown, NY 10940
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  Est $426,835 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 2,138 Sq Ft

  10 Crane Rd, Middletown, NY 10941

  10 Crane Rd, Middletown, NY 10941
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  $1,550,000

  • 5 Beds
  • 5.5 Baths
  • 4,365 Sq Ft

  79 Bisch Rd, Middletown, NY 10940

  Discover the allure of 89 sprawling acres in Orange County, New York, featuring a charming farm house and a tranquil pond. The farmhouse, with its rustic charm and scenic surroundings, holds immense potential as a delightful Airbnb destination or a mini vacation retreat. Its spacious interior, cozy ambiance, and proximity to nature make it an idea I spot for relaxation and rejuvenation.

  Siang Liu P R O Links Realty Inc

  79 Bisch Rd, Middletown, NY 10940
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  $380,000 Sold May 20, 2025

  21 Birch Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 1955

  Last Sold Summary

  • 11% Below List Price
  • $357/SF
  • 26 Days On Market

  Current Estimated Value $384,612

  Last Listing Agent Edith Duncan Donna Ruffino Realty Corp

  21 Birch Dr, Middletown, NY 10940
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  Est $398,026 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,820 Sq Ft

  76 Freezer Rd, Middletown, NY 10941

  76 Freezer Rd, Middletown, NY 10941
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  $155,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  234 Concord Ln, Middletown, NY 10940

  Welcome to this inviting 1-bedroom, 1-bath residence in the heart of Middletown. Featuring an open-living layout with abundant natural light, this unit offers a seamless flow from the living room to the kitchen and plenty of storage. The generously sized bedroom boasts a large closet and easy access to the full bath. Additional perks include in-unit laundry and assigned parking. Located in a

  Malik Subhani Weichert Realtors

  234 Concord Ln, Middletown, NY 10940
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  $425,000 Sold Sep 26, 2025

  3 Kohler Rd, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,920 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Above List Price
  • $221/SF
  • 30 Days On Market

  Current Estimated Value $430,260

  Last Listing Agent Joseph Eugene eXp Realty

  3 Kohler Rd, Middletown, NY 10940
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  Est $306,033 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,512 Sq Ft

  24 Whitman Ct, Middletown, NY 10941

  24 Whitman Ct, Middletown, NY 10941
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  /31

  $349,999 Pending

  • 5 Beds
  • 2 Baths
  • 1,670 Sq Ft

  17 Little Ave, Middletown, NY 10940

  Fully Available...Opportunity Knocks to acquire this fully detached One family home in the heart of the Hudson Valley. This home offers five large bedrooms and two full bathrooms. The Kitchen features granite countertops and Stainless-steel appliances, pocket doors. fully enclosed front Porch, back deck, fenced back yard for Outdoor leisure, dinning, entertaining and endless Possibilities.

  Samar Tarazi Keller Williams Realty

  17 Little Ave, Middletown, NY 10940
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  $280,000 Sold Mar 27, 2025

  63 Deer Ct Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,291 Sq Ft
  • Built 2002

  Last Sold Summary

  • $217/SF
  • 51 Days On Market

  Current Estimated Value $295,679

  Last Listing Agent Joseph Eugene eXp Realty

  63 Deer Ct Dr, Middletown, NY 10940
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  Est $306,915 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft

  32 Sandburg Ct, Middletown, NY 10941

  32 Sandburg Ct, Middletown, NY 10941
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  $99,000

  • Land
  • 6.48 Acres
  • $15,278 per Acre

  0 Fox Meadow Ln, Middletown, NY 12455

  Surveyed 6.4-Acre Hilltop Parcel with perc test, septic plans to be provided, and with electric on property. Perched atop one of the most beautiful and sought-after hills in Margaretville, this exceptional 6+ acre parcel offers a rare opportunity to own your own private slice of Catskills paradise. Located at the very end of a quiet, private road, this property features breathtaking 180-degree

  Susan Doig Listing by Coldwell Banker Timberland Properties

  

  0 Fox Meadow Ln, Middletown, NY 12455

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