Middletown, NY Homes

• 

  

  

  /22

  $740,900 Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,987 Sq Ft

  326 Ingrassia Rd, Middletown, NY 10940

  Welcome to this nearly new four-bedroom, three-bath ranch-style home, nestled on a picturesque two-acre, tree-lined lot that offers both privacy and natural beauty. With stucco siding and a thoughtfully designed layout, this home combines modern comfort with timeless appeal.Step inside to find a spacious, open-concept floor plan with abundant natural light. The main living areas flow

  Catherine Eichner Eichner Realty Group Inc.

  326 Ingrassia Rd, Middletown, NY 10940
• 

  

  

  /9

  $2,116 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  133-3 Wickham Ave Unit ID1056802P, Middletown, NY 10940

  This studio flat is perfectly located for those wanting to experience the lively city of Middletown. With convenient access to local attractions, dining options, and shopping, everything you need is just steps away. Whether you're here to explore or relax, this central location ensures you'll enjoy the best of what the city has to offer.You'll find a well-designed living space that maximizes

  133-3 Wickham Ave Unit ID1056802P, Middletown, NY 10940
• 

  $580,000 Sold Oct 01, 2025

  • 2,633 Sq Ft
  • $220/SF
  • 26 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1989

  306 S Centerville Rd, Middletown, NY 10940

  Staycation in the Country – An Entertainer’s Dream! Discover the perfect blend of comfort, beauty, and functionality in this spacious 4-bedroom, 2.5-bath colonial nestled on a serene 1.6-acre lot in Minisink School District. With room to spread out, incredible indoor and outdoor spaces, this home is your year-round getaway—without ever leaving your driveway. The heart of the home is a show

  Johan Tola Keller Williams Realty Group

  306 S Centerville Rd, Middletown, NY 10940
• 

  Est $631,642 Not Listed For Sale

  • 4 Beds
  • 4 Baths
  • 2,826 Sq Ft

  26 Arbor Way, Middletown, NY 10940

  26 Arbor Way, Middletown, NY 10940
• 

  

  

  /25

  $379,000

  • 2 Beds
  • 1 Bath
  • 1,142 Sq Ft

  390 Hufcut Rd, Middletown, NY 10941

  Light-filled home offering peace & serenity situated on a large, flat grassy lot. This warm home has many upgrades including new siding, almost new roof, many new windows, re-finished hardwood flooring, and more. Easy, one level living offers you a convenient layout with living room, dining room, two good size bedrooms, finished attic with extended living space(bedroom, office etc), unfinished

  Silvana Milinovich RE/MAX Prime Properties

  390 Hufcut Rd, Middletown, NY 10941
• 

  

  /16

  $2,850 per month

  • 3 Beds
  • 2 Baths
  • 1,092 Sq Ft
  • House for Rent

  9 Dubois St, Middletown, NY 10940

  Additional Information: LeaseTerm: Over 12 Months,12 Months,

  Elena James Keller Williams Realty

  9 Dubois St, Middletown, NY 10940
• 

  $335,000 Sold Sep 30, 2025

  • 1,124 Sq Ft
  • $298/SF
  • 89 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1950

  317 Wawayanda Ave, Middletown, NY 10940

  Charming 4-Bedroom Home with Cozy Curb Appeal - A Must See!Welcome to this delightful 4-bedroom, 1-bath single-family home, perfectly nestled in a peaceful, tree-lined neighborhood. With its eye-catching red exterior and classic white trim, this home offers curb appeal that is both inviting and timeless.Step inside to discover a warm, sunlit living space ideal for family

  Pete Wolven Hudson Valley Home Connection

  317 Wawayanda Ave, Middletown, NY 10940
• 

  Est $509,598 Not Listed For Sale

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

  11 Maplewood Dr, Middletown, NY 10940

  11 Maplewood Dr, Middletown, NY 10940
• 

  

  /17

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,496 Sq Ft

  14 Spruce Peak Rd, Middletown, NY 10940

  Welcome Home! Perfectly situated in one of Middletown’s most convenient locations, this beautifully updated 3-bedroom, 1.5-bath townhome offers comfort, style, and space all in one!Step inside to find a bright and welcoming entryway that opens to an updated kitchen featuring gleaming granite countertops, white cabinetry, modern appliances, and a convenient pantry. The formal dining room flows

  Frank Muccari Cronin & Company Real Estate

  14 Spruce Peak Rd, Middletown, NY 10940
• 

  

  /8

  $2,116 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  154 Ny-211 Unit ID1056797P, Middletown, NY 10940

  Feel at home in this peaceful and centrally located apartment in Orange County. With its serene ambiance, this apartment offers a perfect retreat while being close to all the action.Parking is available with 18 spaces allocated on a first-come, first-served basis. While we cannot guarantee or reserve a parking spot in advance, our team is ready to assist if needed.Immerse yourself in the

  154 Ny-211 Unit ID1056797P, Middletown, NY 10940
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  /21

  $151,000 Sold Sep 30, 2025

  • 1,000 Sq Ft
  • $151/SF
  • 265 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1885

  78 Austin St, Middletown, NY 12093

  Price Reduced as a foundation issue identified in one corner. Property is being offered AS IS. My Blue Heaven! A hidden gem nestled at the end of a quiet lane in sophisticated Margaretville and connected to all Village services. The charming 2 bd cottage needs your touch to bring it to life. The secluded and conveniently located oversized parcel abuts Bull Run stream yet is not in the flood

  Lorraine Takahashi Listing by Howard Hanna

  

  78 Austin St, Middletown, NY 12093
• 

  Est $458,145 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  8 Maureen Dr, Middletown, NY 10940

  8 Maureen Dr, Middletown, NY 10940
• 

  /2

  $99,900

  • Land
  • 0.3 Acre
  • $333,000 per Acre

  28 Genung St, Middletown, NY 10940

  **Great investment opportunity in desirable area in Middletown** Not many vacant properties on the market that offer the possibility to build a multi-family unit. This lot is set back from the main road, just behind 32 Genung Street, that is a legal 2-family property.Don't miss out!

  Evelyn Unger Tmimi Weichert Realtors

  28 Genung St, Middletown, NY 10940
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  /26

  $3,300 per month

  • 4 Beds
  • 2 Baths
  • 1,714 Sq Ft
  • House for Rent

  23 Albert St, Middletown, NY 10940

  Spacious 4-Bedroom Mother-Daughter Home for Rent Welcome to 23 Albert Street, a rare rental opportunity in the heart of Middletown! This spacious 4-bedroom, 2-bath whole house rental offers a versatile mother-daughter layout perfect for extended families or those needing extra space. Inside, you’ll find: Two full kitchens – ideal for separate living quarters or added convenience. Four generously

  Kevin Grier Keller Williams Hudson Valley

  23 Albert St, Middletown, NY 10940
• 

  $238,000 Sold Sep 30, 2025

  • 1,790 Sq Ft
  • $133/SF
  • 26 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1971

  72 Greenway Terrace, Middletown, NY 10941

  Townhouse offers great square footage w/full basement. This REO property does need updating and some work but offers home ownership at an affordable price! With three good size bedrooms and very spacious living room. All maintenance of lawn and driveway for snow removal responisbilty of Owner. Offering close proximity to Wallkill Schools, shopping and commuting.

  Maryann Tercasio Howard Hanna Rand Realty

  72 Greenway Terrace, Middletown, NY 10941
• 

  Est $435,365 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft

  35 Roger Ave, Middletown, NY 10940

  35 Roger Ave, Middletown, NY 10940
• 

  

  /32

  $559,900

  • 3 Beds
  • 3 Baths
  • 2,530 Sq Ft

  37 Wisner Ave Unit 39, Middletown, NY 10940

  Stunning 37 Wisner Ave. Experience is gorgeous colonial home located in one of the nicest residential neighborhoods in Middletown. This wonderful home is completely Redone in the finest materials and is a 3-4 Bedroom home that features Harwood Floors throughout the first floor. Open, Airy sun drenched Floor plan. Large Living Rm, Formal Dining Rm, Brand New Open Gourmet Designer Kitchen with

  John Biasi Howard Hanna Rand Realty

  37 Wisner Ave Unit 39, Middletown, NY 10940
• 

  

  /10

  $2,116 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  11 Prince St Unit ID1056810P, Middletown, NY 10940

  Experience the charm of Middletown in this centrally located and peaceful studio. Just a short walk to parks and entertainment, yet tucked away for a quiet retreat, this studio is perfect for singles or couples. It offers a variety of amenities and a convenient smart lock, allowing you to celebrate holidays and enjoy every season in comfort and style, all while being close to everything

  11 Prince St Unit ID1056810P, Middletown, NY 10940
• 

  $265,000 Sold Sep 29, 2025

  • 1,146 Sq Ft
  • $231/SF
  • 52 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1991

  162 Deer Ct Dr, Middletown, NY 10940

  Beautiful Condo in a Prime Location!Experience the perfect blend of comfort and convenience in this ideally located condo, perfect for commuters and those who love being close to the action. Just minutes from major highways, this home offers easy access to shopping centers, restaurants, and daily essentials.For city bound travelers, transportation is a breeze with nearby access to the

  Beverly Huaman Howard Hanna Rand Realty

  162 Deer Ct Dr, Middletown, NY 10940
• 

  Est $464,835 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,584 Sq Ft

  80 Maureen Dr, Middletown, NY 10940

  80 Maureen Dr, Middletown, NY 10940
• 

  

  /38

  $975,000

  • 5 Beds
  • 4.5 Baths
  • 4,200 Sq Ft

  255 Howells Rd, Middletown, NY 10940

  Enter the gates of this grand estate, where you'll find a stunning 5-bedroom, 5-bathroom home spanning 4,200 square feet, complete with a large barn and a natural pond, all set on 36.8 acres. This private estate is located in Middletown, NY, nestled among rolling pastures, tranquil woods, and your very own pond. The expansive property also features a two-story post-and-beam barn with horse

  Jonathon Lee Keller Williams Hudson Valley

  255 Howells Rd, Middletown, NY 10940
• 

  

  /29

  $2,600 per month

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft
  • House for Rent

  6 Charlotte Mews, Middletown, NY 10940

  New renovation, New split air conditioner,New floor ,NEW painting, New toilet on the first floor, New refrigerator, new washing machine, new dryer, garage renovationBeautifully maintained detached townhome in Canterbury Knolls is very convenient to highway, train station and major shopping. Homeowner fee covers lawn maintenance, snow removal, garbage pickup and use of clubhouse. This home has

  Zhiheng Tang Keller Williams Hudson Valley

  6 Charlotte Mews, Middletown, NY 10940
• 

  $306,000 Sold Sep 29, 2025

  • 1,831 Sq Ft
  • $167/SF
  • 58 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2002

  12 Deer Ct Dr, Middletown, NY 10940

  Spacious Townhouse in a Prime Location!This well-located townhouse offers the perfect combination of space, comfort, and convenience. Ideal for commuters and anyone who enjoys being close to all the action. Just minutes from major highways, the home provides easy access to shopping centers, restaurants, and everyday essentials. For city bound travelers, getting around is simple. With nearby

  Beverly Huaman Howard Hanna Rand Realty

  12 Deer Ct Dr, Middletown, NY 10940
• 

  Est $439,494 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,132 Sq Ft

  16 Roger Ave, Middletown, NY 10940

  16 Roger Ave, Middletown, NY 10940
• 

  

  /41

  $399,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 1.5 Baths
  • 1,036 Sq Ft

  15 Clark St, Middletown, NY 10940

  Charming cape with water views on quiet street with boat launch! A total dream! House was recently renovated both inside and out. The recently painted rich, navy blue siding pops as you pull up alongside the newly built stone wall to welcome family and friends. The interior has been updated with new paint and flooring. Neutral colors and touches of shiplap throughout make the whole home very

  Hilary Ryan Goldman Howard Hanna Rand Realty

  15 Clark St, Middletown, NY 10940
• 

  

  /15

  $2,116 per month

  • Studio
  • 1 Bath
  • Condo for Rent

  79 Montgomery St Unit ID1056792P, Middletown, NY 10940

  Feel at home in this bright and stylish studio, perfect for business travelers or those seeking a quick getaway. Ideally located just minutes from the town center and a 5-minute drive to the highway, this apartment offers easy access to NYC and local attractions. Enjoy a sleek, modern space filled with natural light, a cozy desk, coffee machine, and a brand-new kitchenette. With self-check-in and

  79 Montgomery St Unit ID1056792P, Middletown, NY 10940
• 

  $190,000 Sold Sep 29, 2025

  • 924 Sq Ft
  • $206/SF
  • 116 Days On Market

  • 2 Beds
  • 1.5 Baths
  • Built 1989

  224 Concord Ln, Middletown, NY 10940

  Discover this 2-bedroom, 2-bathroom second-floor unit in Middletown, NY! Flooded with abundant sunshine, this lovely home boasts brand-new carpeting and fresh paint throughout. Stay comfortable with an energy-efficient Navien tankless furnace installed in November 2021. The washer, dishwasher, and refrigerator were all updated in 2019. Move-in ready and ideal for starting your homeownership

  Hai Li Keller Williams Hudson Valley

  224 Concord Ln, Middletown, NY 10940
• 

  Est $448,065 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,532 Sq Ft

  26 Robinn Dr, Middletown, NY 10940

  26 Robinn Dr, Middletown, NY 10940
• 

  

  /24

  $579,900

  • 3 Beds
  • 2.5 Baths
  • 2,205 Sq Ft

  30 Daly Rd, Middletown, NY 10940

  New Construction. This 3-bedroom, 2.5-bath colonial is situated on a 2-acre level/partially wooded lot. The first floor offers an oversized living room, dining room, a kitchen with granite countertops and stainless appliances, and sliders leading to a backyard deck. Also on the first floor, you'll find a den/study, a laundry room, and a good-sized 1/2 bath. The second floor features a large loft

  Jonathon Lee Keller Williams Hudson Valley

  30 Daly Rd, Middletown, NY 10940
• 

  

  /15

  $2,200 per month

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

  92 Sheffield Dr, Middletown, NY 10940

  Spacious 3 Bdrm/1.5 bath home in the Town of Wallkill. Enter into a Living Room area followed by a eat-in kitchen with plenty of cabinets space. Open floor layout from kitchen to living room. Laundry area with appliances & half bath complete the 1st level. Upper floor consists of 3 spacious bedrooms and a full bath. Fenced in backyard for summer enjoyment. Driveway with plenty of parking. Minutes

  Sandra Arnez Keller Williams Hudson Valley

  92 Sheffield Dr, Middletown, NY 10940
• 

  $575,000 Sold Sep 26, 2025

  • 2,916 Sq Ft
  • $197/SF
  • 45 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  8 Red Oak Ct, Middletown, NY 10941

  Welcome to this beautifully maintained colonial home, situated in the Pine Bush School District. With just under 3,000 square feet of thoughtfully designed living space, this recently renovated home offers comfort, style, and flexibility for modern living. Inside, you’ll find four spacious bedrooms, plus a versatile bonus room on the main level—perfect for a guest room, home office, or cozy den.

  Patricia Sassi RE/MAX Benchmark Realty Group

  8 Red Oak Ct, Middletown, NY 10941
• 

  Est $449,089 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,684 Sq Ft

  686 Pocatello Rd, Middletown, NY 10940

  686 Pocatello Rd, Middletown, NY 10940
• 

  

  /48

  $1,100,000

  • 4 Beds
  • 3 Baths
  • 2,787 Sq Ft

  441 Scotchtown Collabar Rd, Middletown, NY 10941

  Colonial Masterpiece - This one-of-a-kind Hudson Valley residence artfully combines authentic, historic character with flawless contemporary design set on a bucolic, level parcel. The c. 1790’s antique colonial portion of the home features a timeless natural stone facade, standing seam roof, and welcoming red front door evoking true period charm. An architecturally inspired contemporary wing clad

  Jacob Matthews Ellis Sotheby's Intl Realty

  441 Scotchtown Collabar Rd, Middletown, NY 10941
• 

  

  /18

  $2,900 per month

  • 3 Beds
  • 1 Bath
  • 1,292 Sq Ft
  • House for Rent

  7 Woods Place, Middletown, NY 10940

  Welcome to 7 Woods Place in Middletown, a truly cozy and charming three-bedroom, one-bathroom home that blends comfort, convenience, and character. Fresh to the market and sure to draw attention quickly, this property offers a warm and inviting layout with recent updates, including a new washer and dryer from renovations just two years ago. The home also features an unfinished basement providing

  Virginia Corbett eXp Realty

  7 Woods Place, Middletown, NY 10940
• 

  $490,000 Sold Sep 26, 2025

  • 2,722 Sq Ft
  • $180/SF
  • 98 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1800

  391 Scotchtown Collabar Rd, Middletown, NY 10941

  Discover the Charm and Character of this circa 1800 four bedroom farmhouse colonial on 2.6 acres with a bedroom and bathroom on the main floor!! Do you dream of simpler times? Growing your own fruit herbs vegetables, and eggs? Starry nights in the back yard? It's all here and with many updates including a new roof. There is over 2700 square feet of living space, high ceilings (unheard of in

  John Biasi Howard Hanna Rand Realty

  391 Scotchtown Collabar Rd, Middletown, NY 10941
• 

  Est $554,994 Not Listed For Sale

  • 6 Beds
  • 5 Baths
  • 4,251 Sq Ft

  11 Millsburg Rd, Middletown, NY 10940

  11 Millsburg Rd, Middletown, NY 10940
• 

  

  /50

  $779,999

  • 5 Beds
  • 3.5 Baths
  • 2,778 Sq Ft

  52 Hill Rd, Middletown, NY 10941

  Step into this beautifully designed mother-daughter colonial home on 8.8 acres located in the Town of Hamptonburgh with Goshen Schools. The home featuring 5 bedrooms plus a bonus room with a closet, plus a mother-daughter apartment containing kitchen, bedroom and a full bath. A total of 3,133 square feet Ideal for comfortable living. The living room and family room create the perfect atmosphere

  Bob Edwards Keller Williams Hudson Valley

  52 Hill Rd, Middletown, NY 10941
• 

  

  /29

  $2,250 per month

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Property for Rent

  34 Stern Scenic Dr, Middletown, NY 10940

  Minisink School District! Part of a park community in the Town of Greenville. Facing the lake. Super convenient to Middletown and Port Jervis. Quiet neighborhood. Recent renovations include: brand-new roof, new walls, new ceilings, new hardwood floor and laminate floors, renovated kitchen and bathrooms, new washer and dryer. Beautiful home, schedule a showing. 1-year lease. Tenant responsible for

  Leeshai Lemish PANORAMA REALTY

  34 Stern Scenic Dr, Middletown, NY 10940
• 

  $330,000 Sold Sep 26, 2025

  • 1,263 Sq Ft
  • $261/SF
  • 35 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  11 1/2 Dolson Ave, Middletown, NY 10940

  Back on the Market — Buyer’s Opportunity!This move-in-ready and renovated 3-bedroom Cape Cod in the heart of Middletown combines classic charm with modern updates. Step into a bright, spacious layout featuring a sun-filled living room, formal dining area, and a beautifully updated kitchen — ideal for both daily living and entertaining.The walk-out basement offers generous storage, a

  Robert Siracuse Absolute Real Estate of NY Inc

  11 1/2 Dolson Ave, Middletown, NY 10940
• 

  Est $340,418 Not Listed For Sale

  • 4 Beds
  • 1.5 Baths
  • 1,388 Sq Ft

  50 Millsburg Rd, Middletown, NY 10940

  50 Millsburg Rd, Middletown, NY 10940

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