21,591

Middletown, NY Homes

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  • 199 Baldwin Rd, Middletown, NY 12441
    199 Baldwin Rd, Middletown, NY 12441
    199 Baldwin Rd, Middletown, NY 12441
    /50

    $443,000

    Under Contract
    • 3 Beds
    • 2 Baths
    • 1,232 Sq Ft

    199 Baldwin Rd, Middletown, NY 12441

    Tucked away on 2.2 private acres in a picturesque mountain neighborhood just minutes from Belleayre Ski Center and just over two hours from New York City, this inviting three-bedroom, two-bath contemporary chalet offers the perfect blend of comfort, style, and accessibility. Privately sited and surrounded by natural beauty, the home captures seasonal views of the Belleayre Ski slopes, bringing

    Jeffrey Ashton Listing by Coldwell Banker Timberland Properties

    199 Baldwin Rd, Middletown, NY 12441
  • 54 Linden Ave, Middletown, NY 10940
    54 Linden Ave, Middletown, NY 10940
    54 Linden Ave, Middletown, NY 10940
    /18

    $1,750 - $1,850

    Total Monthly Price

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

    54 Linden Ave, Middletown, NY 10940

    54 Linden Ave, Middletown, NY 10940
  • 2 Stonerose Ct, Middletown, NY 10940

    $499,000

    Sold Jun 30, 2025

    2 Stonerose Ct, Middletown, NY 10940

    • 4 Beds
    • 3.5 Baths
    • 2,966 Sq Ft
    • Built 2015

    Last Sold Summary

    • $168/SF
    • 85 Days On Market

    Current Estimated Value $516,866

    Last Listing Agent Sandra Arnez KW Hudson Valley Untied

    2 Stonerose Ct, Middletown, NY 10940
  • 48 Lone Indian Trail, Middletown, NY 10940
    48 Lone Indian Trail, Middletown, NY 10940
    48 Lone Indian Trail, Middletown, NY 10940
    /50

    $799,999

    Pending
    • 4 Beds
    • 3.5 Baths
    • 2,462 Sq Ft

    48 Lone Indian Trail, Middletown, NY 10940

    SPECTACULAR 180 PANORAMIC MOUNTAIN VIEWS AS FAR AS THE EYES CAN SEE w/ THIS IMMACULATE 4 BR / 3.5 BATH CUSTOM, TWO-STORY, CONTEMPORARY HOME ON FULLY FINISHED DAYLIGHT WALKOUT BASEMENT w/ LARGE WRAPAROUND BACK DECK & 2ND STORY PRIMARY SUITE BALCONY OVERLOOKING THE BREATHTAKING VIEWS OF THE HUDSON VALLEY LANDSCAPE, AND A 2-CAR GARAGE, PRIVATELY SET ON 17.8 ACRES w/ SPRAWLING & WELL-MAINTAINED LAWN

    Olivia Cappelli Donna Ruffino Realty Corp

    48 Lone Indian Trail, Middletown, NY 10940
  • 157 White Bridge Rd, Middletown, NY 10940
    157 White Bridge Rd, Middletown, NY 10940
    157 White Bridge Rd, Middletown, NY 10940
    /11

    $2,300 Per Month

    • 2 Beds
    • 1 Bath
    • 1,041 Sq Ft
    • House for Rent

    157 White Bridge Rd, Middletown, NY 10940

    Updated ranch-style rental on approximately 12 private acres in the Minisink Valley School District. This single-family home offers 1 bedroom, 1 full bathroom, and approximately 1,041 sq ft of living space. Features include vaulted ceilings with exposed beams, skylight, updated bathroom, open kitchen, recessed lighting, sliding glass doors, and peaceful surroundings with privacy. Conveniently

    Yosseline Genao KW Hudson Valley Untied

    157 White Bridge Rd, Middletown, NY 10940
  • 6 Perrins Mews, Middletown, NY 10940

    $354,000

    Sold Oct 31, 2025

    6 Perrins Mews, Middletown, NY 10940

    • 3 Beds
    • 2.5 Baths
    • 1,608 Sq Ft
    • Built 2000

    Last Sold Summary

    • 1% Above List Price
    • $220/SF
    • 12 Days On Market

    Current Estimated Value $362,656

    Last Listing Agent Maureen Cronin Cronin & Company Real Estate

    6 Perrins Mews, Middletown, NY 10940
  • 5 Oak Ridge Rd, Middletown, NY 10940
    5 Oak Ridge Rd, Middletown, NY 10940
    5 Oak Ridge Rd, Middletown, NY 10940
    /24

    $599,000

    • 4 Beds
    • 3 Baths
    • 2,392 Sq Ft

    5 Oak Ridge Rd, Middletown, NY 10940

    Built in 2020, this spacious 2,392 sq ft home offers 4 bedrooms, 3 full bathrooms, and a 2-car garage. The upper level boasts an open-concept layout with vaulted ceilings, a modern kitchen featuring granite countertops and stainless steel appliances, a bright living room, and three bedrooms, including the primary suite, and two full baths. The finished lower level adds even more living space with

    Sandra Laramore Redfin Real Estate

    5 Oak Ridge Rd, Middletown, NY 10940
  • 89 Cottage St Unit SI ID1466589P, Middletown, NY 10940
    89 Cottage St Unit SI ID1466589P, Middletown, NY 10940
    89 Cottage St Unit SI ID1466589P, Middletown, NY 10940
    /22

    $4,107

    Total Monthly Price

    • Studio
    • 1 Bath
    • Condo for Rent

    89 Cottage St Unit SI ID1466589P, Middletown, NY 10940

    The advertised rate of $4,108/month is the lowest available price, based on a 30 day(s) stay with a move-in date of October 19, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    89 Cottage St Unit SI ID1466589P, Middletown, NY 10940
  • 164 Brookline Ave, Middletown, NY 10940
    164 Brookline Ave, Middletown, NY 10940
    164 Brookline Ave, Middletown, NY 10940
    /27

    $340,000

    Sold Jun 01, 2026

    164 Brookline Ave, Middletown, NY 10940

    • 2 Beds
    • 1 Bath
    • 1,050 Sq Ft
    • Built 1920

    Last Sold Summary

    • 3% Below List Price
    • $324/SF
    • 14 Days On Market

    Current Estimated Value $335,719

    Last Listing Agent Scott Alvarez REMAX Solutions

    164 Brookline Ave, Middletown, NY 10940
  • 60 Magnolia Park Rd, Middletown, NY 10940
    60 Magnolia Park Rd, Middletown, NY 10940
    60 Magnolia Park Rd, Middletown, NY 10940
    /33

    $499,000

    Pending
    • 3 Beds
    • 2.5 Baths
    • 2,211 Sq Ft

    60 Magnolia Park Rd, Middletown, NY 10940

    Beautifully cared-for 3 bedroom, 2.5-bath townhouse in the heart of Middletown! Spanning three levels, this home offers comfortable, versatile living with hardwood floors throughout both the main and second levels. The bright main floor features an open-concept living area featuring a fireplace, a dining area, along with a modern kitchen complete with granite countertops and ample cabinet space.

    Sandra Laramore Redfin Real Estate

    60 Magnolia Park Rd, Middletown, NY 10940
  • 950 Route 17m, Middletown, NY 10940
    950 Route 17m, Middletown, NY 10940
    950 Route 17m, Middletown, NY 10940
    /32

    $3,000 Per Month

    • 3 Beds
    • 1 Bath
    • 1,928 Sq Ft
    • House for Rent

    950 Route 17m, Middletown, NY 10940

    STUNNING 3 bedroom/1bath Capecod surrounded by acres of beautifully landscaped views located on the outskirts of Middletown is now available for immediate occupancy. Enter into an oversized living room with a fireplace followed by a Formal dining room with mint shiny hardwood floors. A spacious kitchen with plenty of custom cabinetry and counter space. Beautifully stainless steel appliances and

    Sandra Arnez KW Hudson Valley Untied

    950 Route 17m, Middletown, NY 10940
  • 5 Mills Ave, Middletown, NY 10940

    $327,000

    Sold May 26, 2026

    5 Mills Ave, Middletown, NY 10940

    • 3 Beds
    • 1.5 Baths
    • 1,160 Sq Ft
    • Built 1883

    Last Sold Summary

    • 18% Below List Price
    • $282/SF
    • 243 Days On Market

    Current Estimated Value $315,432

    Last Listing Agent Richard Baxter Keller Williams Realty

    5 Mills Ave, Middletown, NY 10940
  • 1652 Thompson Hollow Rd, Middletown, NY 12459
    1652 Thompson Hollow Rd, Middletown, NY 12459
    1652 Thompson Hollow Rd, Middletown, NY 12459
    /49

    $585,000

    Under Contract
    • 2 Beds
    • 2 Baths
    • 1,253 Sq Ft

    1652 Thompson Hollow Rd, Middletown, NY 12459

    Set in the heart of the picturesque New Kingston Valley, this enchanting two-bedroom, two-bath cottage is privately situated on 20 remarkable acres, offering an increasingly rare combination of complete seclusion, stunning natural beauty, and endless potential. Surrounded by forest and breathtaking mountain views, the property is a sanctuary where the sounds of a year-round stream and the beauty

    Jeffrey Ashton Listing by Coldwell Banker Timberland Properties

    1652 Thompson Hollow Rd, Middletown, NY 12459
  • 13 Jackson Ave Unit 1, Middletown, NY 10940
    13 Jackson Ave Unit 1, Middletown, NY 10940
    /2

    $2,500 Per Month

    • 3 Beds
    • 1 Bath
    • 1,500 Sq Ft
    • !3 Jackson

    13 Jackson Ave Unit 1, Middletown, NY 10940

    3 bed 1 bath apartment

    13 Jackson Ave Unit 1, Middletown, NY 10940
  • 162 Deer Ct Dr, Middletown, NY 10940

    $265,000

    Sold Sep 29, 2025

    162 Deer Ct Dr, Middletown, NY 10940

    • 2 Beds
    • 2 Baths
    • 1,146 Sq Ft
    • Built 1991

    Last Sold Summary

    • $231/SF
    • 52 Days On Market

    Current Estimated Value $266,477

    Last Listing Agent Beverly Huaman Howard Hanna Rand Realty

    162 Deer Ct Dr, Middletown, NY 10940
  • 25 Ferrara Dr, Middletown, NY 10941
    25 Ferrara Dr, Middletown, NY 10941
    25 Ferrara Dr, Middletown, NY 10941
    /35

    $430,000

    • 3 Beds
    • 1 Bath
    • 1,056 Sq Ft

    25 Ferrara Dr, Middletown, NY 10941

    Step into this Beautifully renovated 3 Bedroom, 1 Bath Split Level Home. Perfectly updated with Brand New Roof, Windows, Bright and Airy Kitchen and Modern Bathroom. Brand New Stainless Steel Appliances in Kitchen. Hardwood floors throughout. Nestled on a spacious charming piece of property. Great for outdoor entertaining. It's ready for you to call Home.Great Commuter Location. Close to

    Tracy Lockhart RE/MAX Benchmark Realty Group

    25 Ferrara Dr, Middletown, NY 10941
  • 11 Bonnell Place Unit 1, Middletown, NY 10940
    11 Bonnell Place Unit 1, Middletown, NY 10940
    11 Bonnell Place Unit 1, Middletown, NY 10940
    /8

    $2,400 Per Month

    • 3 Beds
    • 2 Baths
    • 2,380 Sq Ft
    • Apartment for Rent

    11 Bonnell Place Unit 1, Middletown, NY 10940

    Welcome Home to 11 Bonnell Place. This 3-bedroom rental offers spacious sunlit rooms, with bonus living area. Including - bedroom, second bathroom, and a living room with wet-bar. There is plenty of off-street parking, a patio area and yard. Updates have been made throughout. Close to shops, restaurants, and public transportation.

    Connie Tetzlaff Keller Williams Realty

    11 Bonnell Place Unit 1, Middletown, NY 10940
  • 8 Red Oak Ct, Middletown, NY 10941

    $575,000

    Sold Sep 26, 2025

    8 Red Oak Ct, Middletown, NY 10941

    • 4 Beds
    • 3 Baths
    • 2,916 Sq Ft
    • Built 1988

    Last Sold Summary

    • 3% Below List Price
    • $197/SF
    • 45 Days On Market

    Current Estimated Value $569,495

    Last Listing Agent Patricia Sassi RE/MAX Benchmark Realty Group

    8 Red Oak Ct, Middletown, NY 10941
  • 8 Walnut Ln, Middletown, NY 10940
    8 Walnut Ln, Middletown, NY 10940
    8 Walnut Ln, Middletown, NY 10940
    /17

    $399,900

    • 3 Beds
    • 2.5 Baths
    • 1,792 Sq Ft

    8 Walnut Ln, Middletown, NY 10940

    Opportunity knocks in one of Middletown's most convenient and desirable locations! This spacious 3 bedroom, 2.5-bath Colonial with a 2-car garage offers the perfect blend of size, location and potential. Featuring hardwood floors, a functional layout, and a kitchen equipped with stainless steel appliances and granite countertops, this home provides an excellent foundation for creating your own

    Bonnie Natt Realty Promotions Inc

    8 Walnut Ln, Middletown, NY 10940
  • 139 Ruth Ct, Middletown, NY 10940
    139 Ruth Ct, Middletown, NY 10940
    139 Ruth Ct, Middletown, NY 10940
    /23

    $2,000 Per Month

    • 2 Beds
    • 2 Baths
    • 880 Sq Ft
    • Townhouse for Rent

    139 Ruth Ct, Middletown, NY 10940

    Welcome to Eagle's Point Condominium. This beautiful and spacious two bedroom and two full bath condo is ready for you to call home. The master bedroom has a walk-in closet with it's own bath. Washer and dryer in the unit. Large living and dinning, and your own private patio area, which is perfect for summer Bar-B-Q. Close to schools, Hospitals, shopping, Collage, public transpiration, and

    Warren Shelley Reliable Realty Group

    139 Ruth Ct, Middletown, NY 10940
  • 214 Phillips St, Middletown, NY 10940

    $605,000

    Sold Feb 26, 2026

    214 Phillips St, Middletown, NY 10940

    • 4 Beds
    • 3.5 Baths
    • 2,760 Sq Ft
    • Built 2022

    Last Sold Summary

    • 3% Below List Price
    • $219/SF
    • 222 Days On Market

    Current Estimated Value $604,915

    Last Listing Agent Donna Gray Redfin Real Estate

    214 Phillips St, Middletown, NY 10940
  • 19 Putters Way Unit 6, Middletown, NY 10940
    19 Putters Way Unit 6, Middletown, NY 10940
    19 Putters Way Unit 6, Middletown, NY 10940
    /28

    $399,000

    • 2 Beds
    • 2.5 Baths
    • 1,337 Sq Ft

    19 Putters Way Unit 6, Middletown, NY 10940

    Beautiful Townhouse in Fairways at Wallkill! Enjoy maintenance-free living in this desirable Fairways community townhouse. Conveniently located near major highways, shopping, and Orange Regional Medical Center, this home features 2 bedrooms, 2.5 bathrooms, a spacious living room, and a bright private balcony overlooking the pool.Residents have access to outstanding amenities including a

    Xiaohui Cui KW Hudson Valley Untied

    19 Putters Way Unit 6, Middletown, NY 10940
  • 130 Wickham Ave, Middletown, NY 10940
    130 Wickham Ave, Middletown, NY 10940
    130 Wickham Ave, Middletown, NY 10940
    /13

    $2,200 Per Month

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

    130 Wickham Ave, Middletown, NY 10940

    Completely renovated 3-bedroom, 1-bath second-floor apartment available for immediate occupancy. This bright and spacious unit features new flooring, fresh paint, updated kitchen and bath, separate dining area, and generously sized bedrooms. Conveniently located near shopping, restaurants, schools, parks, and major commuter routes.

    Yosseline Genao KW Hudson Valley Untied

    130 Wickham Ave, Middletown, NY 10940
  • 553 Route 17m, Middletown, NY 10940

    $317,000

    Sold Aug 08, 2025

    553 Route 17m, Middletown, NY 10940

    • 2 Beds
    • 1 Bath
    • 1,225 Sq Ft
    • Built 1920

    Last Sold Summary

    • 1% Below List Price
    • $259/SF
    • 98 Days On Market

    Current Estimated Value $323,089

    Last Listing Agent Derek Greene Greene Realty Group

    553 Route 17m, Middletown, NY 10940
  • 38 Putters Way, Middletown, NY 10940
    38 Putters Way, Middletown, NY 10940
    38 Putters Way, Middletown, NY 10940
    /50

    $615,000

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

    38 Putters Way, Middletown, NY 10940

    Well-maintained 3-bedroom, 2.5-bath townhome with a finished basement in the gated community of The Fairways, set alongside a golf course and conveniently located near major highways, Garnet Health Medical Center, shopping, and dining. The main level features hardwood flooring and an open layout connecting the kitchen, dining, and living areas with a gas fireplace. The kitchen includes a

    Jie Liu KW Hudson Valley Untied

    38 Putters Way, Middletown, NY 10940
  • 30 E Main St Unit 4, Middletown, NY 10940
    30 E Main St Unit 4, Middletown, NY 10940
    30 E Main St Unit 4, Middletown, NY 10940
    /7

    $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
  • 145 Academy Ave, Middletown, NY 10940

    $455,000

    Sold Apr 12, 2026

    145 Academy Ave, Middletown, NY 10940

    • 4 Beds
    • 2 Baths
    • 2,545 Sq Ft
    • Built 1900

    Last Sold Summary

    • 2% Above List Price
    • $179/SF
    • 41 Days On Market

    Current Estimated Value $441,744

    Last Listing Agent Sandra Arnez KW Hudson Valley Untied

    145 Academy Ave, Middletown, NY 10940
    • 511 Cty Rte 22, Middletown, NY 10940
      511 Cty Rte 22, Middletown, NY 10940
      511 Cty Rte 22, Middletown, NY 10940
      /31

      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

      • 76 Days On Market

  • 17 Woodrose Ct, Middletown, NY 10940
    17 Woodrose Ct, Middletown, NY 10940
    17 Woodrose Ct, Middletown, NY 10940
    /30

    $505,000

    $10K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 2,763 Sq Ft

    17 Woodrose Ct, Middletown, NY 10940

    Discover the perfect blend of classic charm and modern comfort in this beautiful Colonial-style home. Filled with warmth and character, this cozy yet spacious residence features soaring high ceilings that create an open, airy feel throughout. Each room is thoughtfully designed to offer both elegance and comfort, making the home feel inviting from the moment you step inside. With its timeless

    Ermelinda Mclaughlin eXp Realty

    17 Woodrose Ct, Middletown, NY 10940
  • 65 Jordan Ln, Middletown, NY 10940
    65 Jordan Ln, Middletown, NY 10940
    65 Jordan Ln, Middletown, NY 10940
    /8

    $2,500 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft
    • House for Rent

    65 Jordan Ln, Middletown, NY 10940

    Beautiful freshly painted townhouse features brand new carpet, with 3 bedroom and 2 full bath with 1 half bath on the first floor. Enjoy outdoor living with the private deck. Located near shopping, school and highway. This house is in a prime location for easy access to all amenities. Don't miss out on this fantastic opportunity!

    Mike Mian Century 21 Full Service Realty

    65 Jordan Ln, Middletown, NY 10940
  • 317 Wawayanda Ave, Middletown, NY 10940

    $335,000

    Sold Sep 30, 2025

    317 Wawayanda Ave, Middletown, NY 10940

    • 4 Beds
    • 1 Bath
    • 1,124 Sq Ft
    • Built 1950

    Last Sold Summary

    • 3% Above List Price
    • $298/SF
    • 89 Days On Market

    Current Estimated Value $324,703

    Last Listing Agent Pete Wolven Hudson Valley Home Connection

    317 Wawayanda Ave, Middletown, NY 10940

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