Middletown, NY Homes

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  /50

  $1,150,000

  • 4 Beds
  • 3.5 Baths
  • 5,360 Sq Ft

  289 Pine Grove Rd, Middletown, NY 10940

  Tucked away on 4 sprawling, private acres, this 5,360-square-foot contemporary estate delivers the rare combination of country seclusion, equestrian-ready grounds, and true move-in luxury. Whether you're searching for a peaceful retreat, room to bring your horses, or a multigenerational layout with built-in flexibility, 289 Pine Grove Road checks every box. Step through the soaring foyer into a

  Pedro Garcia Curasi Realty, Inc.

  289 Pine Grove Rd, Middletown, NY 10940
• 

  $490,000

  Sold Aug 07, 2026

  20 Tammy Dr, Middletown, NY 10941

  • 3 Beds
  • 2.5 Baths
  • 1,832 Sq Ft
  • Built 2002

  Last Sold Summary

  • $267/SF
  • 93 Days On Market

  Current Estimated Value $486,955

  Last Listing Agent Sol Perry BHG Real Estate Green Team

  20 Tammy Dr, Middletown, NY 10941
• 

  Est $427,255

  Not Listed For Sale

  11 Keats Rd, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,900 Sq Ft
  • Built 1986

  11 Keats Rd, Middletown, NY 10941

  Last Sold Summary

  • 35 Days On Market

  Last Listing Agent Christina Herschel-Huebner Herschel Realty Corp
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  /10

  $85,000

  Pending

  • Land
  • 1.9 Acres
  • $44,737 per Acre

  64 Brola Rd, Middletown, NY 10940

  Fantastic opportunity to build a new home within the Minisink school district. Level, 1.9 acre lot featuring frontage on the Little Shawangunk Kill. The location is serene yet in close proximity to your everyday conveniences such as shops, restaurants, parks and much more.

  Nicholas Carbone HomeSmart Homes & Estates

  64 Brola Rd, Middletown, NY 10940
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  /2

  $449,900

  Sold Jun 29, 2026

  7015 James Francis Dr, Lockport-Town, NY 14094

  • 3 Beds
  • 2 Baths
  • 1,756 Sq Ft
  • Built 2026

  Last Sold Summary

  • $256/SF
  • 1 Day On Market

  Last Listing Agent Kathleen Dimillo Listing by HUNT Real Estate ERA

  

  7015 James Francis Dr, Lockport-Town, NY 14094
• 

  Est $499,538

  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

  Last Listing Agent Dulce M Ferrera KW Hudson Valley United
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  /39

  $325,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,080 Sq Ft

  10 Forest Ave, Middletown, NY 10940

  AFFORDABLE COLONIAL HOME with low taxes, two bedrooms, one bathroom, and flexible extra space. This 1,080 sq. ft. home features vinyl siding, municipal services, and natural gas for heat, hot water, and cooking. Enjoy private off-street parking for up to three cars, with curb-cut access from two streets. The home offers classic charm and character, a covered front porch, concrete walkways, and

  George Koudounas RE/MAX Benchmark Realty Group

  10 Forest Ave, Middletown, NY 10940
• 

  $375,100

  Sold Sep 02, 2026

  41 Beers Dr, Middletown, NY 10940

  • 3 Beds
  • 1.5 Baths
  • 1,366 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Above List Price
  • $275/SF
  • 20 Days On Market

  Current Estimated Value $365,904

  Last Listing Agent Dien Le Duc Hudson Premium Realty

  41 Beers Dr, Middletown, NY 10940
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  Est $515,361

  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

  Last Listing Agent Michelle Gruberger Real Estate Circuit Inc
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  /29

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,520 Sq Ft

  512 Bloomingburg Rd, Middletown, NY 10940

  Welcome to this beautifully presented 4 bedroom, 2 full bath home offering 1,520 square feet of thoughtfully designed living space on a level 0.50-acre property in the Town of Wallkill with Middletown schools. Freshly painted and filled with natural light, the home offers an amazing open layout complemented by stylish finishes and an exceptionally convenient location.At the heart of the home

  Frank Muccari Cronin & Company Real Estate

  512 Bloomingburg Rd, Middletown, NY 10940
• 

  $345,000

  Sold Jan 02, 2026

  53 Richmond Place, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,144 Sq Ft
  • Built 1936

  Last Sold Summary

  • 1% Below List Price
  • $302/SF
  • 36 Days On Market

  Current Estimated Value $340,880

  Last Listing Agent Kelly Roebuck Curasi Realty, Inc.

  53 Richmond Place, Middletown, NY 10940
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  Est $528,325

  Not Listed For Sale

  8 Rondack Rd, Middletown, NY 10941

  • 4 Beds
  • 3.5 Baths
  • 2,260 Sq Ft
  • Built 1987

  8 Rondack Rd, Middletown, NY 10941

  Last Sold Summary

  • 39 Days On Market

  Last Listing Agent Bethany Wager-Mckee Agnes I Wager Realty Inc.
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  /43

  $415,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 1,625 Sq Ft

  23 W Conkling Ave, Middletown, NY 10940

  BEAUTIFUL turn-key home located in a quiet neighborhood behind Orange County Community College of MIDDLETOWN! Do NOT let the ouside fool you as this home is bigger than expected... Step inside this Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to kitchen. New vinyl floors and recessed lighting throughout. Modern eat-in kitchen with new white

  Sandra Arnez KW Hudson Valley United

  23 W Conkling Ave, Middletown, NY 10940
• 

  $635,000

  Sold Jul 13, 2026

  180 Ridge Dr, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $316/SF
  • 26 Days On Market

  Current Estimated Value $591,180

  Last Listing Agent Tom Pahucki Keller Williams Realty

  180 Ridge Dr, Middletown, NY 10940
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  Est $447,175

  Not Listed For Sale

  3 Frederick St, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1984

  3 Frederick St, Middletown, NY 10941

  Last Sold Summary

  • 23 Days On Market

  Last Listing Agent Kerri Stretch Howard Hanna Rand Realty
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  /19

  $470,000

  • 3 Beds
  • 3 Baths
  • 1,408 Sq Ft

  487 Greenville Turnpike, Middletown, NY 10940

  Welcome to this amazing 3-bedroom ranch in Minisink! Offering a spacious open floor plan, this home is designed for comfortable everyday living and effortless entertaining. The primary bedroom features its own walk-in closet, while 3 full bathrooms provide plenty of convenience for family and guests. The finished basement offers 800+ sq feet of additional living space (NOT included in the listed

  Antonette Vogel BHG Real Estate Green Team

  487 Greenville Turnpike, Middletown, NY 10940
• 

  $300,000

  Sold Jan 21, 2026

  15 Commonwealth Ave, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 1,092 Sq Ft
  • Built 1903

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 44 Days On Market

  Current Estimated Value $300,653

  Last Listing Agent Abbe Distelburger Keller Williams Realty

  15 Commonwealth Ave, Middletown, NY 10940
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  Est $492,417

  Not Listed For Sale

  1 Placid Ave, Middletown, NY 10941

  • 4 Beds
  • 2 Baths
  • 2,000 Sq Ft
  • Built 1987

  1 Placid Ave, Middletown, NY 10941

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent rosemary mcginn Century 21 Full Service Realty
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  /32

  $399,000

  $31K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,748 Sq Ft

  13 Forest Ave, Middletown, NY 10940

  Fresh updates. New improvements. New opportunity.13 Forest Avenue is officially back on the market after completing repairs and updates, and it's ready for its next owner. This spacious home offers comfortable living, updated features, and a convenient location near schools, shopping, restaurants, and commuter routes. The recent improvements provide added value and confidence for buyers

  Pete Wolven Hudson Valley Home Connection

  13 Forest Ave, Middletown, NY 10940
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  $435,000

  Sold Jan 12, 2026

  36 Lake Ave, Middletown, NY 10940

  • 2,262 Sq Ft
  • Built 1890

  Last Sold Summary

  • $192/SF
  • 46 Days On Market

  Current Estimated Value $441,543

  Last Listing Agent Joao Rodrigues Preferred Properties Real Esta

  36 Lake Ave, Middletown, NY 10940
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  Est $481,788

  Not Listed For Sale

  10 Todd Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,352 Sq Ft
  • Built 1977

  10 Todd Dr, Middletown, NY 10941

  Last Sold Summary

  • 211 Days On Market

  Last Listing Agent Anthony Gnagnarelli Keller Williams Valley Realty
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  /15

  $85,000

  • Land
  • 5.1 Acres
  • $16,667 per Acre

  Lot 11 Meadow Brook Dr, Middletown, NY 12455

  Just a short drive from down town Margaretville, tucked away in the pastoral rolling hills, sits this very special 5 acre parcel with lovely open views. What this parcel has to offer is sure to check many boxes on your wish list. A peaceful and serene setting with beautiful scenic views, rolling open meadows backed by magical woods to explore, surrounded by the sounds of nature. With several

  Rosalie Glauser Listing by Frank Lumia Real Estate Plus!, LLC

  

  Lot 11 Meadow Brook Dr, Middletown, NY 12455
• 

  $420,000

  Sold Mar 30, 2026

  52 Scotchtown Dr, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 1,309 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $321/SF
  • 57 Days On Market

  Current Estimated Value $414,312

  Last Listing Agent Luanne McGann Century 21 Full Service Realty

  52 Scotchtown Dr, Middletown, NY 10941
• 

  Est $290,391

  Not Listed For Sale

  6 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1977

  6 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 100 Days On Market

  Last Listing Agent Travis Thompson KW Hudson Valley United
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  /35

  $200,000

  • Land
  • 51.7 Acres
  • $3,868 per Acre

  Tbd Hall Rd, Middletown, NY 12455

  Hike up to see this spectacular 51.7 acres of prime Real Estate. This property has everything except a road which will have to be built. A previous right of way was moved years ago due to flooding. The walk in does require waterproof boots and a lot of good energy. The parcel has every kind of topography you could imagine. Mouch of it is a large lightly wooded plateau. The southeastern boundary

  William Chris St. John Win Morrison Realty

  Tbd Hall Rd, Middletown, NY 12455
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  $180,000

  Sold Sep 02, 2026

  326 Concord Ln, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Below List Price
  • $195/SF
  • 44 Days On Market

  Current Estimated Value $187,556

  Last Listing Agent Sandra Arnez KW Hudson Valley United

  326 Concord Ln, Middletown, NY 10940
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  Est $286,086

  Not Listed For Sale

  62 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  62 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 79 Days On Market

  Last Listing Agent Yara Roussos Homes By Yara Realty Group LLC
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  /46

  $415,000

  $100K PRICE DROP

  • 4 Beds
  • 1.5 Baths
  • 1,732 Sq Ft

  23 Marcy Ln, Middletown, NY 10941

  Welcome to this beautifully renovated raised ranch in the desirable Scotchtown neighborhood. Offering over 1,700 square feet of living space, this move-in-ready home features 4 spacious bedrooms and 2 updated bathrooms.The bright main level offers a spacious L-shaped living and dining room filled with natural light, along with a beautifully renovated kitchen featuring brand-new stainless

  Dennis Aboagye Keller Williams Realty Group

  23 Marcy Ln, Middletown, NY 10941
• 

  $599,000

  Sold Sep 17, 2026

  311 New Vernon Rd, Middletown, NY 10940

  • 3 Beds
  • 2.5 Baths
  • 2,192 Sq Ft
  • Built 1994

  Last Sold Summary

  • 2% Above List Price
  • $273/SF
  • 32 Days On Market

  Current Estimated Value $583,555

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

  311 New Vernon Rd, Middletown, NY 10940
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  Est $308,035

  Not Listed For Sale

  92 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1978

  92 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 32 Days On Market

  Last Listing Agent Wenpeng Guan KW Hudson Valley United
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  /36

  $549,900

  • 2 Beds
  • 2.5 Baths
  • 2,454 Sq Ft

  6 Cyprus Dr, Middletown, NY 10940

  Enjoy the ease of main-level living with the bonus of a beautifully designed second floor in Wildflower at Wallkill, a gated 55+ active-adult community. Offering approximately 2,400 square feet, this spacious two-bedroom, two-and-a-half-bath home features an open, comfortable floor plan designed for both everyday living and entertaining.The main level welcomes you with generous living and

  Patricia Sassi RE/MAX Benchmark Realty Group

  6 Cyprus Dr, 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

  Current Estimated Value $424,760

  Last Listing Agent Lauren Iacono Corcoran Baer & McIntosh

  17 Pine Ct, Middletown, NY 10941
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  Est $297,229

  Not Listed For Sale

  122 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  122 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 158 Days On Market

  Last Listing Agent Sandra Cotthaus 1st Independent Realty Grp
• 

  

  /21

  $899,999

  • 5 Beds
  • 4 Baths
  • 3,820 Sq Ft

  2096 Route 6, Middletown, NY 10940

  Beautifully renovated. Brand new addition 2025. Floor to ceiling stone fireplace with wood burning stone insert, open concept, plenty of room for entertainment. In law set up with kitchenette.

  Silena Mauro S M Target Realty, LLC

  2096 Route 6, Middletown, NY 10940
• 

  $700,000

  Sold Feb 18, 2026

  52 Hill Rd, Middletown, NY 10941

  • 4 Beds
  • 3.5 Baths
  • 2,778 Sq Ft
  • Built 2003

  Last Sold Summary

  • 18% Below List Price
  • $252/SF
  • 106 Days On Market

  Current Estimated Value $711,604

  Last Listing Agent Bob Edwards KW Hudson Valley United

  52 Hill Rd, Middletown, NY 10941
• 

  Est $304,535

  Not Listed For Sale

  5 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  5 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Melissa Trejo Weichert Realtors
• 

  

  /21

  $299,900

  Pre-Foreclosure

  • 3 Beds
  • 1.5 Baths
  • 1,884 Sq Ft

  2 S Aspen Rd, Middletown, NY 10940

  Say hello to possibility! A Middletown townhouse with space, flexibility, and room to make it your own. With 3 bedrooms, and a main-level flex space w/ closet, 2.5 bathrooms, plus inviting outdoor space, this home is ready for your personal touch. Close to everything Middletown offers—shops, dining, parks, and commuter routes—this is a smart move with big potential. Make 2 S. Aspen Rd your next

  Derek Greene Greene Realty Group

  2 S Aspen Rd, Middletown, NY 10940
• 

  $200,000

  Sold Jun 11, 2026

  238 Concord Ln, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1989

  Last Sold Summary

  • $216/SF
  • 30 Days On Market

  Current Estimated Value $200,209

  Last Listing Agent Andi Berisha BHHS Hudson Valley Properties

  238 Concord Ln, Middletown, NY 10940
• 

  Est $314,790

  Not Listed For Sale

  53 Sarah Ln, Middletown, NY 10941

  • 3 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1979

  53 Sarah Ln, Middletown, NY 10941

  Last Sold Summary

  • 58 Days On Market

  Last Listing Agent J Lewis KW Hudson Valley United
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  /38

  $379,900

  $40K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,204 Sq Ft

  39 California Ave, Middletown, NY 10940

  More space than meets the eye! This well-maintained 4-bedroom home features two first-floor bedrooms, a first-floor full bath, an enclosed sunroom, a full basement, a detached two-car garage, and a deep, level backyard. Notable improvements include a new roof, gutters, electrical panel, and exterior painting (2024); a new driveway (2023); whole-home updates in 2018 including new flooring

  Guoqing Ouyang Dalton Wade Real Estate Group

  39 California Ave, Middletown, NY 10940

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