Middletown, NY Homes

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  $310,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,998 Sq Ft

  21 Ridge St, Middletown, NY 10940

  Don’t miss this 4-bedroom, 2-bath Colonial located in the City of Middletown near Touro College and downtown amenities. including eateries, shopping and local amenities. Featuring generous living space and a traditional Colonial layout, this property offers strong potential for owner-occupants or investors alike. Plenty of parking. Close to dining, shopping, transportation, and schools, this is a

  

  Donna Reese

  Keller Williams Hudson Valley

  (329) 210-4027

  21 Ridge St, Middletown, NY 10940
• Explore Middletown

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  /3

  $4,000 per month

  • 4 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

  (329) 219-0850

  184 Highland Ave, Middletown, NY 10940
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  $541,000 Sold Nov 19, 2025

  63 Brimstone Hill Rd, Middletown, NY 10941

  • 3 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1991

  Last Sold Summary

  • $254/SF
  • 49 Days On Market

  Current Estimated Value $538,528

  Last Listing Agent Jennifer Loprieno Howard Hanna Rand Realty

  63 Brimstone Hill Rd, Middletown, NY 10941
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  Not Listed For Sale

  511 Cty Rte 22, Middletown, NY 10940

  • 4 Beds
  • 3.5 Baths
  • 2,609 Sq Ft
  • Built 2024

  511 Cty Rte 22, Middletown, NY 10940

  Last Sold Summary

  • $249/SF
  • 76 Days On Market

  Last Sold Price $649,900

  Last Listing Agent Chris Ogden Realty Promotions Inc
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  /45

  $729,900 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,561 Sq Ft

  195 Mulford Rd, Middletown, NY 10940

  Stunning New Construction colonial on a dead end street. Welcome to your dream home set on 3 picturesque acres in the Town of Greenville, within the highly sought-after Minisink Valley School District. The Oakwood model is nestled on a private, partially wooded lot at the end of a quiet cul-de-sac, offering the perfect blend of style, comfort, and functionality. Step inside to find 4 spacious

  

  Chris Ogden

  Realty Promotions Inc

  (329) 214-0283

  195 Mulford Rd, Middletown, NY 10940
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  $2,300 per month

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

  3 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

  Keller Williams Hudson Valley

  (329) 219-0738

  3 Giada Ln Unit 1, Middletown, NY 10940
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  $383,000 Sold Dec 29, 2025

  12 State St, Middletown, NY 10940

  • 2 Beds
  • 1.5 Baths
  • 1,222 Sq Ft
  • Built 1994

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 21 Days On Market

  Current Estimated Value $381,015

  Last Listing Agent JoAnn Maxwell Howard Hanna Rand Realty

  12 State St, Middletown, NY 10940
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  Est $753,658 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

  • 1% Below List Price
  • $258/SF
  • 24 Days On Market

  Last Sold Price $763,846

  Last Listing Agent Juan Bautista Serhant LLC
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  $849,900 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,407 Sq Ft

  29 Hubbard Rd, Middletown, NY 10940

  New construction colonial on a beautiful 9+ acre lot with views of the Shawangunk Mountain Ridge, a spring fed pond and open fields and woods located on a private dead end road in the Pine Bush S/D. and close to major highways. The Sienna model features include 4 bedrooms, 3.5 baths, gorgeous red oak hardwood floors and spacious rooms. Relax in the cozy living room by the warm inviting fireplace

  

  Chris Ogden

  Realty Promotions Inc

  (845) 209-0146

  29 Hubbard Rd, Middletown, NY 10940
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  $2,100 per month

  • 3 Beds
  • 1 Bath
  • 948 Sq Ft
  • Apartment for Rent

  56 Watkins Ave, Middletown, NY 10940

  Spacious 3BR/1BA Second-Floor Unit. Bright and nicely updated second-floor unit featuring 3 bedrooms and 1 bathroom. Enjoy a sunny eat-in kitchen, fresh paint throughout, and newer hardwood flooring. Additional attic space included, attic space is ONLY for storage use. Located in a quiet neighborhood just a short distance from parks, the YMCA, shops, commuter trains, and bus lines. Tenant pays

  

  Jennifer Loprieno

  Howard Hanna Rand Realty

  (329) 224-0247

  56 Watkins Ave, Middletown, NY 10940
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  $170,000 Sold Jun 27, 2025

  156 School House Rd, Middletown, NY 10940

  • 3 Beds
  • 1 Bath
  • 924 Sq Ft
  • Built 1970

  Last Sold Summary

  • $184/SF
  • 62 Days On Market

  Last Listing Agent Tracy McNamara Keller Williams Realty

  156 School House Rd, Middletown, NY 10940
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  Est $724,984 Not Listed For Sale

  175 Elise Dr, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,626 Sq Ft
  • Built 2021

  175 Elise Dr, Middletown, NY 10941

  Last Sold Summary

  • 17% Above List Price
  • $236/SF
  • 152 Days On Market

  Last Sold Price $620,000

  Last Listing Agent Bonnie Natt Realty Promotions Inc
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  /25

  $330,000

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  71 Commonwealth Ave, Middletown, NY 10940

  Middletown Gem: Updated Home, Unbeatable Location, Finally Priced Right. Welcome to 70 miles of freedom from NYC with none of the sacrifice. This thoughtfully updated Middletown home sits in one of Orange County's most connected communities, where Metro-North train access and major highway proximity put Manhattan within easy reach while keeping you rooted in the peace and affordability of Hudson

  

  Brian Caplicki

  Keller Williams Hudson Valley

  (329) 212-0993

  71 Commonwealth Ave, Middletown, NY 10940
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  $2,000 per month

  • 2 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • Apartment for Rent

  49 Lake Ave Unit 2, Middletown, NY 10940

  Beautifully renovated upstairs apartment featuring two bedrooms and one bathroom. An additional room offers the perfect space for a home office. This rental includes a cozy kitchen, a comfortable living room, and an oversized laundry room. Upstairs, you’ll find a storage area (not permitted for sleeping purposes). Two parking spaces are designated for tenant use, and a back patio provides a nice

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 666-0584

  49 Lake Ave Unit 2, Middletown, NY 10940
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  $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 $480,533

  Last Listing Agent Andrea Rose Keller Williams Hudson Valley

  39 Brookline Ave, Middletown, NY 10940
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  Est $550,485 Not Listed For Sale

  37 Orange Terrace, Middletown, NY 10940

  • 4 Beds
  • 2.5 Baths
  • 2,668 Sq Ft
  • Built 2019

  37 Orange Terrace, Middletown, NY 10940

  Last Sold Summary

  • 5% Above List Price
  • $197/SF
  • 23 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Sharon Reynolds Keller Williams Hudson Valley
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  $1,799,000 Open Sun 12AM - 2AM

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

  3 Bristol Dr, Middletown, NY 10941

  Welcome to 3 Bristol Road, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 square feet of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment.Built in 2002, this 6-bedroom, 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

  (329) 215-0309

  3 Bristol Dr, Middletown, NY 10941
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  $2,300 per month

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

  6 Giada Ln Unit 6, 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

  Keller Williams Hudson Valley

  (329) 216-1096

  6 Giada Ln Unit 6, Middletown, NY 10940
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  $360,000 Sold May 01, 2025

  142 South St, Middletown, NY 10940

  • 4 Beds
  • 1.5 Baths
  • 2,151 Sq Ft
  • Built 1928

  Last Sold Summary

  • 31% Above List Price
  • $167/SF
  • 140 Days On Market

  Current Estimated Value $363,206

  Last Listing Agent Sharon Sheil Coldwell Banker Realty

  142 South St, Middletown, NY 10940
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  Est $554,732 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

  • 11% Above List Price
  • $221/SF
  • 13 Days On Market

  Last Sold Price $500,000

  Last Listing Agent Michael Guattery Keller Williams Realty
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  $499,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,132 Sq Ft

  22 Sharon Dr, Middletown, NY 10941

  Welcome to 22 Sharon Drive in Middletown, a well-maintained raised ranch offering space, comfort, and a highly convenient location. The main level features hardwood floors throughout, a large living room with high ceilings, and an expansive dining area ideal for everyday living and entertaining. The kitchen is finished with granite countertops and offers great functionality. The upper level

  

  Ammar Iqbal

  eXp Realty

  (329) 201-2409

  22 Sharon Dr, Middletown, NY 10941
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  $2,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,428 Sq Ft
  • House for Rent

  10 Chaucer Ct, Middletown, NY 10941

  Located in the desirable Pine Bush School District, this well-maintained rental is ready for immediate occupancy! This spacious home offers three bedrooms and 1.5 bathrooms with a functional layout perfect for comfortable living.The first level features tile flooring throughout, a beautifully updated galley kitchen, a designated dining area, and a large living room filled with natural light.

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 210-2217

  10 Chaucer Ct, Middletown, NY 10941
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  $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 $393,135

  Last Listing Agent Katheryn DeClerck Howard Hanna Rand Realty

  112 Monhagen Ave, Middletown, NY 10940
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  Est $532,943 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

  • 6% Above List Price
  • $169/SF
  • 17 Days On Market

  Last Sold Price $505,000

  Last Listing Agent Ermelinda Mclaughlin eXp Realty
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  $250,000 Pending

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

  34 Poplar Ln, Middletown, NY 10941

  This well-maintained home offers comfort, space, and convenience in a desirable location close to shopping, dining, and public transportation. Step inside to find generously sized bedrooms with vaulted ceilings that create an open and airy feel. The rear bedroom features a private balcony—perfect for morning coffee or unwinding at the end of the day. A full basement provides ample storage space,

  

  John Olivero

  Keller Williams Realty

  (329) 212-1039

  34 Poplar Ln, Middletown, NY 10941
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  $2,600 per month

  • 3 Beds
  • 1.5 Baths
  • 1,280 Sq Ft
  • House for Rent

  38 Hampton Ct, Middletown, NY 10941

  This gorgeous rental is move-in ready and beautifully updated throughout. The kitchen features numerous upgrades, including granite countertops with a complementary backsplash, stainless steel appliances, and an abundance of crisp white cabinetry. There is also space for a table and chairs—perfect for casual meals. The home offers brand-new flooring and fresh paint throughout. Enjoy year-round

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 216-0860

  38 Hampton Ct, Middletown, NY 10941
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  $300,000 Sold Jul 15, 2025

  103 Deer Court Dr, Middletown, NY 10940

  • 2 Beds
  • 2 Baths
  • 1,296 Sq Ft
  • Built 2002

  Last Sold Summary

  • 3% Below List Price
  • $231/SF
  • 15 Days On Market

  Current Estimated Value $310,467

  Last Listing Agent Tanya Von Montague BHHS Hudson Valley Properties

  103 Deer Court Dr, 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

  • $96/SF
  • 79 Days On Market

  Last Sold Price $125,500

  Last Listing Agent Carol Cruz Keller Williams Hudson Valley
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  $625,000 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 3,013 Sq Ft

  43 Putters Way, Middletown, NY 10940

  This beautiful, and very well maintained four level condo is situated not far from the entrance gate and next to a parking area for visitors. Wood floors throughout the first floor and second floor hall. The carpet in the bedrooms is new. The 4th level office is a great private space. Two transom topped french doors in the living room lead out to a private paver patio surrounded by tall

  

  Chris Staritz

  Howard Hanna Rand Realty

  (329) 214-0732

  43 Putters Way, Middletown, NY 10940
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  $2,250 per month

  • 2 Beds
  • 1.5 Baths
  • 1,115 Sq Ft
  • Condo for Rent

  10 Kensington Way, Middletown, NY 10940

  Experience this beautifully renovated two-bedroom, one-and-a-half-bath townhouse in Water Edge, Middletown. Step inside to find brand-new kitchen appliances, stunning new hardwood floors, and fresh paint throughout. The updated bathrooms feature modern vanities that add a stylish, elegant touch. Enjoy the added convenience of an in-unit washer and dryer.Ideally located just across from serene

  

  Hazel Cello

  Keller Williams Hudson Valley

  (329) 217-0459

  10 Kensington Way, Middletown, NY 10940
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  $480,000 Sold Mar 06, 2025

  31 Lindentree Ln, Middletown, NY 10940

  • 3 Beds
  • 3.5 Baths
  • 1,723 Sq Ft
  • Built 2017

  Last Sold Summary

  • 4% Below List Price
  • $279/SF
  • 88 Days On Market

  Current Estimated Value $505,452

  Last Listing Agent Larry Curasi Curasi Realty, Inc.

  31 Lindentree Ln, Middletown, NY 10940
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  Est $705,053 Not Listed For Sale

  239 Sands Rd, Middletown, NY 10941

  • 4 Beds
  • 2.5 Baths
  • 2,422 Sq Ft
  • Built 2022

  239 Sands Rd, Middletown, NY 10941

  Last Sold Summary

  • 15% Above List Price
  • $254/SF
  • 59 Days On Market

  Last Sold Price $615,000

  Last Listing Agent Marion Bruhns Howard Hanna Rand Realty
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  $329,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 1 Bath
  • 976 Sq Ft

  39 Orange Terrace, Middletown, NY 10940

  Are you looking for an affordable home? You have found it here. This beautifully updated three-bedroom, one-bath home sits on a spacious 0.21-acre lot, offering the perfect blend of comfort, style, and outdoor living. Inside, the home features a bright and welcoming living area, a refreshed kitchen with modern finishes, and a clean, updated bathroom designed for everyday convenience.Step

  

  Catherine Eichner

  Eichner Realty Group Inc.

  (329) 208-2797

  39 Orange Terrace, Middletown, NY 10940
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  $2,150 - $2,800 per month

  Southgate Middletown

  1 - 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,

  20 Uhlig Rd, Middletown, NY 10940
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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 $269,646

  Last Listing Agent Sharon Reynolds Keller Williams Hudson Valley

  242 1/2 W Main St, Middletown, NY 10940
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  Not Listed For Sale

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  

  Lot 11 Meadowbrook Dr, Middletown, NY 12455

  Last Sold Summary

  • 44 Days On Market

  Last Sold Price $80,000

  Last Listing Agent Susan Doig Listing by Coldwell Banker Timberland Properties
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  $475,000 Coming Soon

  • 3 Beds
  • 3 Baths
  • 1,674 Sq Ft

  57 Boorman Rd, Middletown, NY 10940

  This nicely renovated Dutch Colonial is located on 5+ acres surrounded by mature trees just minutes from Middletown and in Minisink schools. Renovated kitchen has Quartz counters, ceramic tile floor, subway tile back splash, new cabinets and stainless appliances. Wood stove for additional source of heat, first floor full bath and livingroom, diningroom rounds out the first floor. Upstairs find a

  

  Lynelle Alessi

  Keller Williams Hudson Valley

  (329) 212-0455

  57 Boorman Rd, Middletown, NY 10940
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  $1,500 per month

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

  30 E Main St Unit 4, Middletown, NY 10940

  Move-In Ready One-Bedroom Apartment in the Heart of Middletown. This one-bedroom apartment is ready for you to move in and make it your own. Located in the heart of Middletown, it offers convenience and comfort just moments from Garnet Health Medical Center, Touro Medical College, OCCC, major highways, public transportation, restaurants, and shopping. Street parking is available, making it easy

  Courtney Tablante Keller Williams Realty

  30 E Main St Unit 4, Middletown, NY 10940
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  $603,000 Sold Jun 03, 2025

  33 Highland View Place, Middletown, NY 10940

  • 4 Beds
  • 3 Baths
  • 2,411 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Below List Price
  • $250/SF
  • 65 Days On Market

  Current Estimated Value $613,565

  Last Listing Agent Warren Shelley Reliable Realty Group

  33 Highland View Place, Middletown, NY 10940
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  Est $386,149 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

  • 21% Above List Price
  • $195/SF
  • 33 Days On Market

  Last Sold Price $320,000

  Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

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