Middletown, NY Homes

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  /30

  $479,000

  • 3 Beds
  • 3.5 Baths
  • 1,723 Sq Ft

  8 Atwood Dr, Middletown, NY 10940

  Experience elevated townhome living in this beautifully maintained residence located in the sought-after Maple Fields neighborhood of Middletown. Offering elegance and modern updates, this home delivers comfort, space, and convenience, just a short distance from transportation options to New York City. Upon entry, you’re welcomed by gleaming hardwood floors and a thoughtfully designed open layout

  Sandra Laramore Redfin Real Estate

  8 Atwood Dr, Middletown, NY 10940
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  /46

  $1,720 - $2,680 per month

  Sutton Hill Apartments

  1 - 3 Beds

  2 Underhill Rd, Middletown, NY 10940

  Living at Sutton Hill located in Middletown, NY, provides you with the peaceful, pastoral setting of the Catskill's and the Pocono's, and only an hour away from New York City.Convenient to the Metro North RR, near Orange Regional Medical center - schools, shopping and entertainment, all at your fingertips.Relax and enjoy our great amenities: Fitness Center, Pool, Playground,

  2 Underhill Rd, Middletown, NY 10940
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  /12

  $72,000 Sold May 02, 2025

  Tbd Dimmick Mountain Rd, Middletown, NY 12430

  • Land
  • 2.74 Acres
  • $26,277 per Acre

  Last Sold Summary

  • 4% Below List Price
  • 144 Days On Market

  Last Listing Agent Sara Gorman Maliha Coldwell Banker Village GreenK

  Tbd Dimmick Mountain Rd, Middletown, NY 12430
• 

  Est $374,101 Not Listed For Sale

  21 Hill Rd, Middletown, NY 10941

  • 2 Beds
  • 1 Bath
  • 1,386 Sq Ft
  • Built 1958

  21 Hill Rd, Middletown, NY 10941

  Last Sold Summary

  • 33% Above List Price
  • $203/SF
  • 42 Days On Market

  Last Sold Price $281,000

  Last Listing Agent Rosy Wansor Wansor Realty
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  /38

  $445,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,545 Sq Ft

  145 Academy Ave, Middletown, NY 10940

  Come tour this LOVELY NEWLY REMODELED Middletown Colonial!! This 4 bedroom home is in turn-key condition with the upgrades that it offers. A front deck where you can enjoy morning coffee leads you into a living room followed by a dining room with modern lighting and an open floor plan to a STUNNING eat-in kitchen with new vinyl floors throughout. Admire this spacious eat in kitchen that features

  Sandra Arnez Keller Williams Hudson Valley

  145 Academy Ave, Middletown, NY 10940
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  /11

  $2,100 per month

  • 3 Beds
  • 1 Bath
  • 1,231 Sq Ft
  • Apartment for Rent

  14 Liberty St Unit 2, Middletown, NY 10940

  Charming 3-bedroom, 1-bath upstairs apartment available for rent in the heart of Middletown. This inviting home features an open kitchen layout that flows comfortably into the living space, creating a warm and functional environment ready for you to move right in. The apartment offers three spacious bedrooms with ample room for rest, work, or additional storage.Conveniently located near local

  Maria Sairrino Cronin & Company Real Estate

  14 Liberty St Unit 2, Middletown, NY 10940
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  $314,900 Sold Sep 17, 2025

  936 Tower Ridge Cir, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,216 Sq Ft
  • Built 2007

  Last Sold Summary

  • $259/SF
  • 4 Days On Market

  Last Listing Agent Angelo Acierno Keller Williams Realty

  936 Tower Ridge Cir, Middletown, NY 10941
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  Not Listed For Sale

  5 Fortune Rd W Unit M, Middletown, NY 10941

  • 2 Beds
  • 2 Baths
  • 1,112 Sq Ft
  • Built 1972

  5 Fortune Rd W Unit M, Middletown, NY 10941

  Last Sold Summary

  • $225/SF
  • 72 Days On Market

  Last Sold Price $249,900

  Last Listing Agent Marie Altieri Howard Hanna Rand Realty
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  /28

  $598,000 Pending

  • 3 Beds
  • 3 Baths
  • 3,021 Sq Ft

  34 Feiertag Rd, Middletown, NY 10941

  BACK ON THE MARKET.........Let your dreams begin with large colonial home located on a Cul-de-Sac in the Pine Bush School District. Step inside to a large and open foyer with high ceilings which creates a welcoming atmosphere. The main level features a formal dining room, den/office, cozy family room with woodburning fireplace, open eat in kitchen with breakfast area, full bath and enclosed

  Julianna Cotthaus 1st Independent Realty Grp

  34 Feiertag Rd, Middletown, NY 10941
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  /50

  $2,250 - $2,500 per month

  The Regency Club

  1 - 2 Beds

  1200 Regency Ct, Middletown, NY 10940

  The Regency Club offers spacious living and dining areas, and modern kitchens in one bedroom with den and two bedroom floor plans. Apartments boast 9 ft. ceilings, ceramic tiles in the bathrooms and kitchens and a full appliance package. Residents enjoy the clubhouse, outdoor pool, state-of-the-art fitness center, and expansive club room as well as the outdoor tennis court and playground. The

  1200 Regency Ct, Middletown, NY 10940
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  $945,000 Sold Feb 06, 2026

  346 Mullock Rd, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 3,282 Sq Ft
  • Built 1999

  Last Sold Summary

  • 3% Below List Price
  • $288/SF
  • 83 Days On Market

  Current Estimated Value $959,754

  Last Listing Agent Alyse Toffel Keller Williams Hudson Valley

  346 Mullock Rd, Middletown, NY 10940
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  Not Listed For Sale

  100 Hillside Dr Unit C8, Middletown, NY 10941

  • 2 Beds
  • 2.5 Baths
  • 1,418 Sq Ft
  • Built 1987

  100 Hillside Dr Unit C8, Middletown, NY 10941

  Last Sold Summary

  • $208/SF
  • 116 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Xiaohui Cui Keller Williams Hudson Valley
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  /40

  $465,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,899 Sq Ft

  11 Cobblestone Ln, Middletown, NY 10940

  Welcome to this bright and spacious 3-bedroom, 2.5-bath townhouse, that’s perfect for today’s busy lifestyle. The spacious layout is filled with natural light, creating a warm and inviting atmosphere for all to gather. The main level offers plenty of room for both everyday living and entertaining, while the upper level features comfortable bedrooms, including a primary suite with its own private

  Antoinette Gundersen HomeSmart Homes & Estates

  11 Cobblestone Ln, Middletown, NY 10940
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  /13

  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,992 Sq Ft
  • Apartment for Rent

  16 Wallkill Ave, Middletown, NY 10940

  Rare opportunity to rent the 1st floor unit of this well-maintained home. This rental features 2 bedrooms, 1 bathroom. Enjoy the convenience of off street parking w/2 dedicated driveway parking spots. Centrally located near the YMCA, public transportation (Shortline bus), and local parks, providing easy access to all that the City of Middletown has to offer. No smoking. Pets considered on a

  Jackie Siracuse Absolute Real Estate of NY Inc

  16 Wallkill Ave, Middletown, NY 10940
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  $430,000 Sold Aug 07, 2025

  11 Dogwood Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,338 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $321/SF
  • 37 Days On Market

  Current Estimated Value $446,712

  Last Listing Agent Gloria Allan John J Lease REALTORS Inc

  11 Dogwood Dr, Middletown, NY 10940
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  Est $112,822 Not Listed For Sale

  92 Linden Ave, Middletown, NY 10940

  • Built 1918

  92 Linden Ave, Middletown, NY 10940

  Last Sold Summary

  • 74% Above List Price
  • $48/SF
  • 83 Days On Market

  Last Sold Price $65,000

  Last Listing Agent Ashley Olson Minard eXp Realty
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  /41

  $499,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,955 Sq Ft

  1 Weather Vane Way, Middletown, NY 10940

  Welcome to the one that finally checks all the boxes at 1 Weather Vane Way, Middletown, NY. This beautifully updated raised ranch offers 4 bedrooms, 2.5 baths, and the perfect blend of modern comfort, smart upgrades, and effortless living. Step inside to an open, airy living room that flows seamlessly into the dining room, which in turn opens directly into the remodeled kitchen, creating the

  Jessica Evans Keller Williams Hudson Valley

  1 Weather Vane Way, Middletown, NY 10940
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  /17

  $817 - $1,486 per month

  Deerfield Commons

  1 - 3 Beds

  2 Edward Diana Way, Middletown, NY 10941

  The Deerfield Commons Middletown apartments offer a comfortable yet stylish lifestyle right in the heart of the community. With a wide range of amenities and an efficient 761 square foot room plan, each airy one-bedroom apartment provides the perfect home for individuals and families. Deerfield also offers a limited number of 2-bedroom and 3-bedroom units.Set in the warm surroundings of

  2 Edward Diana Way, Middletown, NY 10941
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  $631,000 Sold Jun 23, 2025

  169 Mulford Rd, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,418 Sq Ft
  • Built 2025

  Last Sold Summary

  • 5% Above List Price
  • $261/SF
  • 27 Days On Market

  Last Listing Agent Brian Caplicki Keller Williams Hudson Valley

  169 Mulford Rd, Middletown, NY 10940
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  Not Listed For Sale

  180 Weld Rd, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,064 Sq Ft
  • Built 2006

  180 Weld Rd, Middletown, NY 10941

  Last Sold Summary

  • $75/SF
  • 120 Days On Market

  Last Sold Price $80,000

  Last Listing Agent Sandra Spector Howard Hanna Rand Realty
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  $499,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,868 Sq Ft

  9 Randall Heights, Middletown, NY 10940

  Wow! Absolutely stunning, fully renovated 3-bedroom, 2-bath ranch — completely renovated! This beautiful home features New windows, a brand-new kitchen with quartz countertops, tiled backsplash, and stainless-steel appliances. Enjoy gleaming hardwood floors, warm fireplace (professionally cleaned) spacious and bright living areas, modern bathrooms, and tasteful finishes throughout. Nothing to do

  Naomi Streicher Q Home Sales

  9 Randall Heights, Middletown, NY 10940
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  /6

  $1,699 per month

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Apartment for Rent

  92 Fitzgerald Dr, Middletown, NY 10940

  Beautifully Renovated Apartment in the Heart of Middletown – Move-In Ready!Discover modern comfort in this freshly renovated apartment located in desirable Middletown, NY 10940. Featuring a stunning brand-new kitchen equipped with sleek stainless steel appliances, contemporary cabinetry, and ample counter space—perfect for home cooks and entertaining. The updated bathroom offers a fresh,

  Samuel Pollak North Point Management Corp

  92 Fitzgerald Dr, Middletown, NY 10940
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  $390,500 Sold Feb 13, 2026

  28 Lake Ridge Dr, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,460 Sq Ft
  • Built 2002

  Last Sold Summary

  • 7% Above List Price
  • $267/SF
  • 32 Days On Market

  Current Estimated Value $368,553

  Last Listing Agent Jonathon Lee Keller Williams Hudson Valley

  28 Lake Ridge Dr, Middletown, NY 10940
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  Est $489,231 Not Listed For Sale

  22 Prince St, Middletown, NY 10940

  • 9 Beds
  • 4 Baths
  • 2,894 Sq Ft
  • Built 1931

  22 Prince St, Middletown, NY 10940

  Last Sold Summary

  • 7% Above List Price
  • $158/SF
  • 31 Days On Market

  Last Sold Price $457,500

  Last Listing Agent Sandra Arnez Keller Williams Hudson Valley
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  $640,000

  • 4 Beds
  • 2.5 Baths
  • 2,424 Sq Ft

  235 Maples Rd, Middletown, NY 10940

  This well-maintained spacious Colonial Home is ideally situated on a 2 Acre Lot in the Town of Wallkill Countryside. Lovely Kitchen W/Breakfast nook overlooks a Large Level Backyard & Private Rear Entertainment Deck. An entry foyer greets you when you arrive at this home, that features a Formal Dining Room, Living Room, Family Room, Powder Room, & mud Room/Laundry to complete the 1st Floor. The

  Shernette Hall VYLLA Home

  235 Maples Rd, Middletown, NY 10940
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  /18

  $2,204 - $3,869 per month

  Sterling Parc at Middletown

  1 - 2 Beds

  23 James P Kelly Way, Middletown, NY 10940

  Sterling Parc at Middletown is located at 23 James P Kelly Way Middletown, NY and is managed by Solomon Management LLC, a reputable property management company with verified listings on RENTCafe. Sterling Parc at Middletown offers one and two bedroom apartments ranging in size from 816 to 1,231 sq.ft. Amenities include Carpeting, Dishwasher, Fireplace, Clubhouse, Concierge, and more. This rental

  23 James P Kelly Way, Middletown, NY 10940
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  $498,000 Sold Aug 27, 2025

  15 Cobblestone Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,790 Sq Ft
  • Built 2010

  Last Sold Summary

  • 2% Above List Price
  • $278/SF
  • 26 Days On Market

  Current Estimated Value $503,502

  Last Listing Agent Katherine Burgos-Llewellyn Call it Closed Intl. Realty

  15 Cobblestone Ln, Middletown, NY 10940
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  Not Listed For Sale

  34 Linden Ave, Middletown, NY 10940

  • 5 Beds
  • 5 Baths
  • 2,538 Sq Ft
  • Built 1920

  34 Linden Ave, Middletown, NY 10940

  Last Sold Summary

  • $166/SF
  • 9 Days On Market

  Last Sold Price $422,000

  Last Listing Agent Moses Zwiebel MS Realty Group USA, Inc
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  /18

  $429,000

  • 3 Beds
  • 2.5 Baths
  • 2,097 Sq Ft

  4 Kless Ct, Middletown, NY 10940

  Welcome to this well-kept 3-bedroom home with a bonus loft, set in the Maple Fields community. The first floor offers an easy, open layout with a comfortable living area that leads out to a private patio, along with a dining space and a kitchen that includes a pantry, tile accents, and stainless steel appliances. Upstairs you’ll find the primary bedroom featuring a walk-in closet and its own

  Bryant Moran YourHomeSold Guaranteed Realty

  4 Kless Ct, Middletown, NY 10940
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  /7

  $2,400 per month

  • 2 Beds
  • 2 Baths
  • 1,142 Sq Ft
  • Apartment for Rent

  206 Golf Links Rd Unit 626, Middletown, NY 10940

  This new 2 bedroom 2 bath apartment features a modern and stylish design, with high quality finishes and attention to detail throughout. The living room is adorned with a large window that allows plenty of natural light to illuminate the space, creating an inviting and airy atmosphere. The kitchen is equipped with stainless steel appliances, sleek quartz countertops, ample cabinet storage, and a

  Victoria Fini Curasi Realty, Inc.

  206 Golf Links Rd Unit 626, Middletown, NY 10940
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  $340,000 Sold Jun 09, 2025

  25 Lake Ridge Dr, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,188 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Above List Price
  • $286/SF
  • 24 Days On Market

  Current Estimated Value $352,335

  Last Listing Agent Christina Rowan Howard Hanna Rand Realty

  25 Lake Ridge Dr, Middletown, NY 10940
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  Est $491,152 Not Listed For Sale

  19 Meadow View Dr, Middletown, NY 10940

  • 3 Beds
  • 4 Baths
  • 2,581 Sq Ft
  • Built 2014

  19 Meadow View Dr, Middletown, NY 10940

  Last Sold Summary

  • 15% Above List Price
  • $165/SF
  • 20 Days On Market

  Last Sold Price $426,000

  Last Listing Agent Rebecca Kane Keller Williams Hudson Valley
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  /34

  $485,000

  • 3 Beds
  • 3.5 Baths
  • 2,521 Sq Ft

  49 Woodside Knolls Dr, Middletown, NY 10940

  Welcome to Woodside Knolls! Discover this beautiful tri-level townhouse located in one of the area’s most desirable communities. This weill maintained home features 9' ceilings on the main level, a cherry kitchen with granite countertops and stainless steel appliances, and gleaming hardwood floors throughout the main level. Enjoy 3 spacious bedrooms and 3.5 bathrooms, including a fully finished

  Naomi Streicher Q Home Sales

  49 Woodside Knolls Dr, Middletown, NY 10940
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  /25

  $2,195 per month

  Northwoods Apartments

  1 - 2 Beds

  300 Northwoods Rd, Middletown, NY 10940

  Nestled in the historic Hudson River Valley of Middletown, New York, Northwoods Apartments is a community of apartment homes boasting a country-like setting with panoramic mountain views. You will enjoy a well-rounded activity rich lifestyle complemented by state-of-the-art-on-site amenities including a fitness center, clubroom, half basketball court and playground.A

  300 Northwoods Rd, Middletown, NY 10940
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  $310,000 Sold Aug 18, 2025

  15 Independence Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,320 Sq Ft
  • Built 1966

  Last Sold Summary

  • 6% Below List Price
  • $235/SF
  • 11 Days On Market

  Current Estimated Value $326,608

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  15 Independence Ave, Middletown, NY 10940
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  Not Listed For Sale

  25 Fairways Dr Unit 5, Middletown, NY 10940

  • 2 Beds
  • 2.5 Baths
  • 1,345 Sq Ft
  • Built 2005

  25 Fairways Dr Unit 5, Middletown, NY 10940

  Last Sold Summary

  • $243/SF
  • 73 Days On Market

  Last Sold Price $327,500

  Last Listing Agent Dennis Clark Howard Hanna Rand Realty
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  /43

  $549,900 Pending

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

  21 Cyprus Dr, Middletown, NY 10940

  Welcome to Wildflower at Wallkill—offering easy, one-floor living in one of Orange County’s most sought after 55+ active communities. This well-designed Woodbridge model features two bedrooms and two full baths, along with an open living and dining room combination, while the open kitchen and family room area makes everyday living and entertaining effortless! Enjoy the oversized composite deck,

  Patricia Sassi RE/MAX Benchmark Realty Group

  21 Cyprus Dr, Middletown, NY 10940
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  /17

  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • Apartment for Rent

  26 Mill St Unit 2, Middletown, NY 10940

  BEAUTIFUL MIDDLETOWN side by side Tri-level is now available to RENT! This RENOVATED rental offers ample indoor and outdor space. Enter into a renovated Living room with modern vinyl floors throughout with an open floor layout. A modern kitchen with granite counters and gorgeous island for everyday seating and newer stainless steel appliances. A beautiful full tiled bath with a tub, modern

  Sandra Arnez Keller Williams Hudson Valley

  26 Mill St Unit 2, Middletown, NY 10940
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  $460,000 Sold Jan 15, 2026

  295 Lybolt Rd, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • Built 1980

  Last Sold Summary

  • 4% Below List Price
  • $376/SF
  • 56 Days On Market

  Current Estimated Value $479,031

  Last Listing Agent Britanni Gaucher Keller Williams Realty

  295 Lybolt Rd, Middletown, NY 10941
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  Est $297,141 Not Listed For Sale

  142 Sycamore Dr Unit Bldg 8, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,110 Sq Ft
  • Built 1977

  142 Sycamore Dr Unit Bldg 8, Middletown, NY 10940

  Last Sold Summary

  • 8% Above List Price
  • $248/SF
  • 29 Days On Market

  Last Sold Price $275,000

  Last Listing Agent Vincent Richards Exit Realty Group

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