Middletown, NY Homes

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  /30

  $359,900

  Pending

  • 2 Beds
  • 1.5 Baths
  • 1,322 Sq Ft

  7 Rowan St, Middletown, NY 10940

  Here is the rare first home that costs almost nothing to worry about. It has been remodeled through and through, so the bills that scare new owners are already behind you. The kitchen is brand new. The bathroom is brand new. The roof is only 8 years young, the siding is new, the windows are new, and even the water service line has been replaced. Natural gas heat keeps the coldest stretch of

  

  Brian Caplicki

  KW Hudson Valley United

  7 Rowan St, Middletown, NY 10940
• Explore Middletown

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  /33

  $3,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,486 Sq Ft
  • House for Rent

  184 Highland Ave, Middletown, NY 10940

  Welcome to this beautiful Victorian-style rental, centrally located in the heart of Middletown, NY. From the moment you arrive, the charming wrap-around porch sets a warm and inviting tone, perfectly complementing the home’s classic character. Inside, you’ll find an updated interior featuring a modern kitchen, a brand-new central air system, new windows, and new doors, providing both comfort and

  

  Chativa Bowen

  Keller Williams Realty

  184 Highland Ave, Middletown, NY 10940
• 

  $482,500

  Sold Oct 06, 2025

  39 Brookline Ave, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2005

  Last Sold Summary

  • 2% Below List Price
  • $258/SF
  • 26 Days On Market

  Current Estimated Value $491,652

  Last Listing Agent Andrea Rose KW Hudson Valley United

  39 Brookline Ave, Middletown, NY 10940
• 

  Est $525,791

  Not Listed For Sale

  26 Linden Ave Unit 24, Middletown, NY 10940

  • 6 Beds
  • 2 Baths
  • 2,784 Sq Ft
  • Built 1900

  26 Linden Ave Unit 24, Middletown, NY 10940

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Jonathon Lee KW Hudson Valley United
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  /41

  $435,000

  $5K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  35 Pinto Rd E, Middletown, NY 10941

  Welcome to 35 Pinto Rd E! This is am immaculate townhouse in a prime, community location---Liberty Commons. This 2+Bedroom, 3 Bath is the perfect combination of contemporary luxury living with convenience. This end unit features , open concept first floor, natural light galore, custom blinds, plenty of storage, spacious bedrooms with large closets, and 2 car tandem garage. Need more.... There is

  

  Tiffany Megna

  Howard Hanna Rand Realty

  35 Pinto Rd E, Middletown, NY 10941
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  /21

  Starting at $2,625 Per Month

  • 2 Beds

  20 Uhlig Rd, Middletown, NY 10940

  The brand new residences at Southgate Middletown offer a community feel in the center of rapidly growing Middletown, N.Y. Here, an amenity-rich lifestyle awaits, with beautiful homes that feature only the finest in custom appointments and design. See for yourself how easy it would be to call Southgate home. The style of Southgate living features soaring 9-foot ceilings, exquisite luxury flooring,

  Southgate Middletown

  

  20 Uhlig Rd, Middletown, NY 10940
• 

  $390,000

  Sold Sep 25, 2025

  112 Monhagen Ave, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft
  • Built 1870

  Last Sold Summary

  • 5% Above List Price
  • $232/SF
  • 27 Days On Market

  Current Estimated Value $399,853

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  112 Monhagen Ave, Middletown, NY 10940
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  Est $801,893

  Not Listed For Sale

  147 Elise Dr, Middletown, NY 10941

  • 5 Beds
  • 3.5 Baths
  • 2,960 Sq Ft
  • Built 2024

  147 Elise Dr, Middletown, NY 10941

  Last Sold Summary

  • 24 Days On Market

  Last Listing Agent Juan Bautista Serhant LLC
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  $649,000

  $20K PRICE DROP

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

  23 Orange Terrace, Middletown, NY 10940

  Experience a one-of-a-kind custom-built A-Frame that blends rustic charm with modern luxury. Nestled on a quiet street in the city, this stunning home commands attention with its reflective tinted windows, dramatic architecture, and incredible curb appeal.Designed for both entertaining and everyday living, the expansive wraparound deck features a built-in wired speaker system, creative

  

  Joao Rodrigues

  Preferred Properties Real Esta

  23 Orange Terrace, Middletown, NY 10940
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  /10

  $3,000 Per Month

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft
  • House for Rent

  204 Stony Ford Rd, Middletown, NY 10941

  Experience the peace and tranquility of the Hudson Valley in this charming ranch-style rental nestled on 2 private, wooded acres. Offering 3 bedrooms, 1 full bathroom, and a bright open-concept living area, this home provides the perfect setting for both everyday living and entertaining.Whether you're looking for your first rental home, downsizing, or simply seeking a peaceful retreat, this

  

  Chativa Bowen

  Keller Williams Realty

  204 Stony Ford Rd, Middletown, NY 10941
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  $265,000

  Sold Oct 28, 2025

  242 1/2 W Main St, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,080 Sq Ft
  • Built 1950

  Last Sold Summary

  • 4% Below List Price
  • $245/SF
  • 20 Days On Market

  Current Estimated Value $286,196

  Last Listing Agent Sharon Reynolds KW Hudson Valley United

  242 1/2 W Main St, Middletown, NY 10940
• 

  Est $808,793

  Not Listed For Sale

  197 Elise Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 3,217 Sq Ft
  • Built 2024

  197 Elise Dr, Middletown, NY 10941

  Last Sold Summary

  • 61 Days On Market

  Last Listing Agent Juan Bautista Serhant LLC
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  /47

  $528,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,704 Sq Ft

  18 Maureen Ln, Middletown, NY 10940

  Custom built and lovingly maintained by its original owners, this beautiful 4-bedroom ranch is being offered for the very first time. Nestled at the end of a quiet cul-de-sac in the highly sought-after Minisink Valley School District, with Otisville Elementary, this special home reflects years of pride in ownership and thoughtful care. A welcoming covered front porch invites you inside to a

  

  JoAnn Maxwell

  Howard Hanna Rand Realty

  18 Maureen Ln, Middletown, NY 10940
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  /40

  Starting at $1,875

  Total Monthly Price

  • 1 - 2 Beds

  700 Stratford Ln, Middletown, NY 10940

  Welcome to Country Manor Apartments in Middletown, NY! Our pet-friendly community is set among rustic, large, grassy areas, creating a peaceful and open environment. We offer one- and two-bedroom apartments featuring updated kitchens, premium bathrooms, and private decks. Your rent includes heat, hot water, sewer, and trash removal. We also offer 24/7 maintenance services.

  Country Manor Apartments

  

  700 Stratford Ln, Middletown, NY 10940
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  $420,000

  Sold Feb 19, 2026

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,858 Sq Ft
  • Built 2011

  Last Sold Summary

  • 7% Below List Price
  • $226/SF
  • 55 Days On Market

  Current Estimated Value $444,337

  Last Listing Agent Virginia Corbett eXp Realty

  5 Cobblestone Ln Unit 4301, Middletown, NY 10940
• 

  Est $559,064

  Not Listed For Sale

  16 4th St, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,260 Sq Ft
  • Built 2023

  16 4th St, Middletown, NY 10940

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Michael Guattery Keller Williams Realty
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  /46

  $574,900

  $25K PRICE DROP Pending

  • 3 Beds
  • 2 Baths
  • 2,432 Sq Ft

  180 Mt Orange Rd, Middletown, NY 10940

  The primary suite alone tells you what kind of home this is. A vaulted cathedral ceiling overhead, a spa-style bath built around a deep soaking tub, and proportions that hold a quiet hour at the end of a long day the way a private retreat is supposed to. It is the kind of room that quietly redefines what you expect a ranch to feel like. By the time the water is running, the day has already

  

  Brian Caplicki

  KW Hudson Valley United

  180 Mt Orange Rd, Middletown, NY 10940
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  /28

  $2,300 Per Month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Apartment for Rent

  7 Giada Ln Unit 1, Middletown, NY 10940

  Experience Modern Living in a Brand-New 2-Bedroom Apartment. Take advantage of this rare opportunity to move into a newly constructed 2-bedroom apartment, thoughtfully designed with high-end finishes and modern conveniences. Enjoy a welcoming open floor plan that features a stunning kitchen complete with Quartz countertops and brand-new, energy-efficient stainless steel appliances. Oversized

  

  Dulce M Ferrera

  KW Hudson Valley United

  7 Giada Ln Unit 1, Middletown, NY 10940
• 

  $480,000

  Sold Nov 14, 2025

  93 Rolling Meadows Rd, Middletown, NY 10940

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

  Last Sold Summary

  • $234/SF
  • 23 Days On Market

  Current Estimated Value $487,431

  Last Listing Agent Suzanne Bongiorno Century 21 E & M Williams Rlty

  93 Rolling Meadows Rd, Middletown, NY 10940
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  Est $541,902

  Not Listed For Sale

  44 Highrose Ridge Way, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,996 Sq Ft
  • Built 2014

  44 Highrose Ridge Way, Middletown, NY 10940

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Ermelinda Mclaughlin eXp Realty
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  /15

  $489,900

  Pending

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

  11 Avoncroft Ln, Middletown, NY 10940

  11 Avoncroft Lane, Middletown, NY offers 3 bedrooms, 3.5 bathrooms, approximately 2,521 sq. ft., central air, forced-air heat, and a finished walkout basement. This spacious Orange County residence provides flexible living areas for everyday comfort, entertaining, remote work, guest space, or recreation. Conveniently located near shopping, dining, parks, commuter routes, and Hudson Valley

  

  Randolph Rogers

  eXp Realty

  11 Avoncroft Ln, Middletown, NY 10940
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  /55

  Starting at $2,672 Per Month

  • 1 - 2 Beds

  122 Golf Links Rd, Middletown, NY 10940

  158 Unit Luxury Housing Community with 1,2 and 3 Bedroom Units. Situated on a Lush Championship 18 Hole Golf Course that offers a Private Country Club Experience 24 hours a day. Apartments feature Spacious Open Layouts, Beautiful Kitchens with Quartz Countertops and Stainless Steel Appliances, Front Loading Washers and Dryers, Balconies, Walk-In Closets, Beautiful Engineered Wide Plank

  Residences at West Hills Country Club

  

  122 Golf Links Rd, Middletown, NY 10940
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  $372,000

  Sold Dec 19, 2025

  29 Euclid Ave, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,512 Sq Ft
  • Built 1965

  Last Sold Summary

  • 6% Above List Price
  • $246/SF
  • 33 Days On Market

  Current Estimated Value $386,263

  Last Listing Agent John Olivero Keller Williams Realty

  29 Euclid Ave, Middletown, NY 10940
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  Not Listed For Sale

  2607 State Route 17k, Middletown, NY 10941

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

  2607 State Route 17k, Middletown, NY 10941

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Carol Cruz Curasi Realty, Inc.
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  /25

  $160,000

  $5K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  226 Concord Ln, Middletown, NY 10940

  Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has

  

  Lynelle Alessi

  KW Hudson Valley United

  226 Concord Ln, Middletown, NY 10940
• 

  

  /22

  $2,200 Per Month

  • 2 Beds
  • 1 Bath
  • 984 Sq Ft
  • Condo for Rent

  1 Ruth Ct, Middletown, NY 10940

  Welcome to this beautifully updated and spacious first floor corner condo in Middletown, NY. This well-maintained home offers comfortable one level living with a large living room, two generously sized bedrooms, and one full bath. The modern walk-through kitchen features new stainless steel appliances and an adjacent dining area. Wall A/C units in the living room and both bedrooms provide

  

  Kathy White

  Exit Realty Connections

  1 Ruth Ct, Middletown, NY 10940
• 

  $440,000

  Sold Nov 21, 2025

  6 Randall Terrace, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1957

  Last Sold Summary

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

  Current Estimated Value $437,701

  Last Listing Agent Rachel Hunt Realty Promotions Inc

  6 Randall Terrace, Middletown, NY 10940
• 

  Est $388,940

  Not Listed For Sale

  237 Route 211 W, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 1,638 Sq Ft
  • Built 1900

  237 Route 211 W, Middletown, NY 10940

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group
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  /32

  $1,680,000

  • 5 Beds
  • 9 Baths
  • 7,794 Sq Ft

  3 Bristol Dr, Middletown, NY 10941

  Welcome to 3 Bristol Drive, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment. Built in 2002, this 6-bedroom suits, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday

  

  Mohamed Elgoarany

  All American Realty Management

  3 Bristol Dr, Middletown, NY 10941
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  /46

  Starting at $1,750 Per Month

  • 1 - 2 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,

  Sutton Hill Apartments

  

  2 Underhill Rd, Middletown, NY 10940
• 

  $455,500

  Sold Dec 23, 2025

  30 Avoncroft Ln, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft
  • Built 2010

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 38 Days On Market

  Current Estimated Value $472,070

  Last Listing Agent Cindy-Lee Dorcely KW Hudson Valley United

  30 Avoncroft Ln, Middletown, NY 10940
• 

  Est $447,693

  Not Listed For Sale

  366 North St, Middletown, NY 10940

  • 6 Beds
  • 3 Baths
  • 3,330 Sq Ft
  • Built 1880

  366 North St, Middletown, NY 10940

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Anthony Gnagnarelli Keller Williams Valley Realty
• 

  /2

  $155,000

  $20K PRICE DROP Pending

  • 1 Bed
  • 1 Bath
  • 784 Sq Ft

  45 Knapp Ave, Middletown, NY 10940

  Attention investors! This is a true “what you see is what you get” opportunity. Bring your tools and imagination and transform this property into a valuable addition to your rental portfolio. Perfect for investors seeking potential and long-term returns. Cash buyer or rehab loan needed.

  

  Dulce M Ferrera

  KW Hudson Valley United

  45 Knapp Ave, Middletown, NY 10940
• 

  

  /25

  $3,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • House for Rent

  708 Silver Lake Scotchtown Rd, Middletown, NY 10941

  STUNNING RENTAL IN DESIRABLE SCOTCHTOWN! This beautifully updated home is move-in ready and offers the perfect blend of style, comfort, and convenience. The gorgeous kitchen is a chef's dream, featuring high-end smart appliances, elegant quartz countertops, a classic subway tile backsplash, an abundance of crisp white cabinetry, and a breakfast bar that seamlessly opens to the spacious living and

  

  Hazel Cello

  KW Hudson Valley United

  708 Silver Lake Scotchtown Rd, Middletown, NY 10941
• 

  $403,000

  Sold Sep 05, 2025

  12 Brewster Dr, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1960

  Last Sold Summary

  • 1% Above List Price
  • $382/SF
  • 38 Days On Market

  Current Estimated Value $401,046

  Last Listing Agent Philip Barnao eXp Realty

  12 Brewster Dr, Middletown, NY 10940
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  Est $540,890

  Not Listed For Sale

  9 Neptune Ln, Middletown, NY 10940

  • 3 Beds
  • 3 Baths
  • 1,993 Sq Ft
  • Built 2024

  9 Neptune Ln, Middletown, NY 10940

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Melinda White Keller Williams Realty
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  /50

  $680,000

  $50K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 1,996 Sq Ft

  90 M and M Rd, Middletown, NY 10940

  Set on nearly 5 private, wooded acres in the Town of Wallkill within the Pine Bush School District, this move-in-ready home blends refined interior updates with exceptional outdoor living in the heart of Orange County, NY. Outstanding curb appeal begins with updated landscaping, dramatic stone walls, modern vertical siding, and a welcoming center courtyard entry leading to a covered portico with

  

  Lynelle Alessi

  KW Hudson Valley United

  90 M and M Rd, Middletown, NY 10940
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  /18

  Starting at $2,431 Per Month

  • 1 - 2 Beds

  23 James P Kelly Way, Middletown, NY 10940

  Sterling Parc at Middletown offers 1 and 2 bedroom apartments in Middletown, NY with spacious floor plans, modern finishes, and convenient access to major destinations. Located in the Hudson Valley near Route 17 and I-84, the community places residents close to shopping, dining, entertainment, and commuter routes. Apartment homes feature designer kitchens with shaker-style espresso cabinetry,

  Sterling Parc at Middletown

  

  23 James P Kelly Way, Middletown, NY 10940
• 

  $435,000

  Sold Jun 05, 2026

  20 Dubois St Unit 18 1/2, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 1,417 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Above List Price
  • $307/SF
  • 31 Days On Market

  Last Listing Agent Isaiah Lopez KW Hudson Valley United

  20 Dubois St Unit 18 1/2, Middletown, NY 10940
• 

  Est $500,828

  Not Listed For Sale

  38 Anthony St, Middletown, NY 10940

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft
  • Built 2024

  38 Anthony St, Middletown, NY 10940

  Last Sold Summary

  • 238 Days On Market

  Last Listing Agent JoAnn Maxwell Howard Hanna Rand Realty

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