Middletown, New York listings for sale

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$435,000 - Middletown, NY
8-10 Mercer Street Middletown, NY - GORGEOUS 3 bedroom/2 bath Cape Cod is now available for your purchase! A beautiful paver stairway leads you to your new home. Enter into a living room that's freshly painted with modern colors with plenty of window light and Lifeproof vinyl flooring. The eat-in kitchen features new modern cabinetry, granite counters, trendy backsplash, and fresh out the box stainless steel appliances. 1st level bath offers a tub with new tiled floors, fixtures and modern lighting. Two ground level bedrooms for your convenience. The upper level offers the 3rd bedroom Suite with its own private bath that featuring a standup shower AND a soaking tub! A large family room is located in the lower area as well as an office for those that work remotely. A laundry area with a new Washer and dryer are also found in the lower level. Plenty of storage space available in this finished basement where a workout area or playroom can easily be setup. This home is equipted with ductless mini splits units throughout the home for Heating & Cooling! Ample parking in the driveway. Small back deck ideal for grilling and green areas to enjoy & entertain. Last but not least, New Roof, siding, appliances fresh out the box, water heater, brand new sewer line from the home to the street & new electric and plumbing. Minutes to Maple Hill Schools, Maple Hill park, fine dining, shopping centers, and Heritage Trail. Close proximity to Touro Medical and Garnet Health. Commuter friendly with bus and train transportation near. Book your tour and make this lovely house your home today!
1951 | 3 | 2 | 2,006 sqft.
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$429,999 - Middletown, NY
19 Wawayanda Avenue Middletown, NY - Price reduced....... A Must see... Fully available opportunity knocks to own this colonial home, located in the heart of the Hudson Valley. Entering this home with a long foyer that leads into a living room, spacious dining room with plenty of natural light, eat in kitchen, Kitchen is updated with lots of cabinet space front deck, back porch, new flooring for the entire house. New roof, stainless steel appliances, new heating system, new furnace, central air, new base board. This updated colonial home offers 6 bedrooms and two full bathrooms. there is a first-floor bedroom and full bathroom on the first floor. Additional five bedrooms and one renovated bathroom on the second floor with a double vanity sink on the second floor. this house offers solar panel. central air This house is close to all major transportation, highways 17 and 84 metro north train station, walking distance to short line bus, parks, schools, minutes from Touro Collage Medical School, hiking trails, minutes to Garnet Health Medical Center, minutes' walk to downtown Middletown with summer concerts, Restaurants, LEGOLAND, ski resort the Catskill, world casino, lakes much more.
1920 | 6 | 2 | 1,878 sqft.
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$425,000 - Middletown, NY
36 Pinetree Lane Middletown, NY - A Designer’s Dream Retreat in the Heart of the Catskills Step into timeless elegance and tranquility with this custom-crafted, artist-designed 4-bedroom, 2-bath home featuring a radiant north-facing sunroom. Set on just under an acre of fully manicured land, this property offers the ultimate Catskills escape—secluded, serene, and exquisitely maintained. Every element of the home has been thoughtfully created by a designer and custom builder, blending sophisticated modern finishes with the rich warmth of Old New York character. From carefully restored architectural details to tasteful, high-end updates, this residence is a rare turnkey gem. The expansive front deck welcomes you in, while the upstairs sunroom provides ideal escape for relaxation or creativity. The beautifully restored barn, already connected to municipal water and sewer, offers limitless potential for a guest apartment, ADU, or inspired workspace. An expanded private road and parking area—including direct barn access—adds ease for guests or future short-term rental potential. The home is not in a flood zone and remains incredibly quiet and secluded, while still being part of a short-term rental–friendly community. Located just minutes from Belleayre Ski Mountain and within walking distance to Main Street’s charming shops and top-tier dining, you’ll enjoy the best of both worlds— seclusion with effortless access to a vibrant, thriving Catskills town. The Trailways bus route even drops you steps from your private road, making weekend escapes and guest arrivals a breeze. Whether you're searching for a full-time dream home, an artist’s sanctuary, or a high-performing rental investment, this one-of-a-kind property is ready for its next chapter. Come see it today—this special retreat won’t last long!
1900 | 4 | 2 | 1,981 sqft.
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$425,000 - Middletown, NY
128 Academy Street Middletown, NY - Step into a property that does it all—gorgeous turnkey vacation home, lucrative Airbnb, a multi-generational getaway, or a sun-filled retreat with built-in income potential. Whether you're looking for a serene escape from city life, or you're an investor ready to house hack your way to passive income, this property checks every box! Modern & spacious, this home offers two distinct living spaces under one roof—perfect for Airbnb guests, multi-family use, or keeping the upstairs for yourself while the downstairs pays the mortgage. The original section of the home features classic charm with modern styling: wood floors, exposed beams, a cozy wood-burning stove, and an open-concept layout that flows from living room to dining area to a bright, modern kitchen with newer appliances. With two bedrooms on each level and a full bath on both floors, you’ll have plenty of space for guests or renters. The back deck is made for al fresco dinners, stargazing, or lazy weekend mornings with coffee in hand. Upstairs, a sun-soaked addition feels like your own Catskills penthouse. Lofty cathedral ceilings, large skylights, and a wide-open floor plan connect the living, dining, and kitchen areas, all opening to a private balcony with mountain views. The back yard is huge and private, perfect for summer games, a garden, or letting the dogs run around to their hearts content! All this within walking distance to the sweet village of Margaretville with its shops, dining and entertainment! Use one unit, rent the other. Host guests, share with family, or enjoy the entire home to yourself—this is flexibility at its finest. Whether you're escaping the city, building your investment portfolio, or looking for a move-in ready home in a desirable village, this property is ready to welcome you.
1952 | 6 | 3 | 3,300 sqft.
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$425,000 - Middletown, NY
225 Highland Avenue Middletown, NY - Great Opportunity For Future Owner Occupant Or An Investor Who Is Looking To Collect $4,450 Of Current Rental Income With Tenants In Place.Fully Renovated In 2020. The Property Was Originally A 2 Family And Has Two Levels, Basement And A Full Attic. 2 Forced Hot Air Systems With Separate Gas And Electric Services. Both Sides Are Set With First Floor Kitchen With Door To Deck On Rear. Living Room And Dining Room. Second Floor Has 3 Bedrooms And 1 Full Bath On Each Side. Each With Walk-Up Attic Stairs. Parking Features:1 Car Detached
1910 | 6 | 2 | 2,748 sqft.
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$425,000 - Middletown, NY
47 Prince Street Middletown, NY - Welcome to this lovely, renovated. Formerly a 3 bedroom/2-bathroom house, this home has been renovated in 2023 into a 4 bed/2.5 bath adding a 1st Floor Master Bedroom Suite, increasing the square footage of living space. This house has plenty of character and is better than new construction. Open Concept Layout, Enclosed Porch, Luxury Vinyl Flooring, Stainless Steel Appliances, Butcher Block Countertops, Dual sink in Master Bathroom, 1st floor Powder Room, 1st Floor Laundry Closet for stackable washer and dryer. 2nd floor consists of 3 ample size bedroom and a full bath. Energy Efficient Windows that brings in plenty of light, Solar Panel is PAID IN FULL and increases the value of the home so enjoy low-cost electric bills without the monthly solar bill! ACT NOW, WON'T LAST!
1880 | 4 | 2 | 1,620 sqft.
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$419,900 - Middletown, NY
54 Brewster Drive Middletown, NY - Welcome to this charming 3 bedroom, 1 and 1/2 bath raised ranch in the heart of Middletown, NY. This home boasts beautiful hardwood floors throughout and is located in an established neighborhood with mature trees and well-kept homes. Step inside to find new carpet and fresh paint throughout, creating a warm and inviting atmosphere. The main level features a spacious living room, dining area, and kitchen with access to a deck perfect for outdoor entertaining. Downstairs you will find a cozy family room, ideal for movie nights or relaxing. There is also an additional guest room that could be used as an office or playroom. Close to parks , schools , restaurants and shopping. Don't miss your opportunity to own this lovely home in Middletown - schedule your showing today!
1985 | 3 | 2 | 1,914 sqft.
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$405,000 - Middletown, NY
5 Peace Drive Middletown, NY - Commuter's Dream in the Town Of Wallkill ! This 3 Bedroom Raised Ranch offers hardwood flooring throughout main living area, bow window which allows tons of natural light to illuminate living & dining area. Enjoy Cooking? Large kitchen with granite counter tops & tons of cabinet space. Plenty of room on lower level for a family room or home office. Walk out to your rear deck with your morning coffee & admire your level rear yard. Close to I-84, Route 17, Crystal Run Galleria, & Shopping on Route 211.
1972 | 3 | 1 | 1,144 sqft.
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$399,900 - Middletown, NY
568 County Route 49 Middletown, NY - FOR INVESTORS ONLY.... New townhouse on right side (Unit 2C) available in the Minisink Valley School District. This home welcomes you to an open foyer that leads to an updated kitchen with Quartz/Quartzite countertops and ample white cabinets. Lots of sunshine enters this home. The dining and living room area is spacious with beautiful floors. Huge closet that can be used as a pantry. A deck to enjoy barbecures. The second floor comes with three bedrooms and 2 full bathrooms. The primary bedroom can easily hold a king size bed and has a walk-in closet with built in shelves and primary bathroom. Ample space in the other two bedroms with bigger than usual closets. There's a hall bathroom and a washer and dryer on second level as well. The same beautiful floors can be found throughout the second level. One car garage with an additional parking area. Unfinished basement with plenty of storage space. Come take a look!! Additional Information: Amenities:Storage,HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Attached,
2003 | 3 | 2 | 1,593 sqft.
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$399,900 - Middletown, NY
151 School House Road Middletown, NY - Peaceful 5-Acre Retreat in Minisink Valley School District – 151 Schoolhouse Rd, Middletown, NY -Welcome to 151 Schoolhouse Rd – a private 5-acre sanctuary nestled on a quiet country road in the sought-after Minisink Valley School District. This spacious bilevel home offers over 1,900 sq ft of comfortable living space, combining modern updates with serene, natural surroundings. Upstairs, you’ll find a beautifully renovated kitchen featuring granite countertops, ceramic tile flooring, stainless steel appliances, and direct access to a large back deck – perfect for grilling, entertaining, or simply enjoying the expansive views of your partially wooded, partially cleared backyard. The open-concept main level also includes, vinyl flooring, a sun-filled living room with large windows, recessed lighting, and a cozy stone-faced wood-burning fireplace with a classic mantle. Three generous bedrooms and a stylishly updated full bathroom complete the upper floor. Downstairs offers flexible space for a home office, recreation room, or guest area, along with a dedicated laundry and storage area. The home features vinyl siding, gutters, and ceiling fans throughout for added comfort and convenience. A long paved driveway leads to a large parking area below, offering both privacy and practicality. The small front and side yards are easy to maintain, while the expansive backyard, surrounded by mature trees, provides the ideal setting for peace and seclusion. Located in the heart of the Hudson Valley, this property is a dream for outdoor lovers — close to local wineries, hiking, and biking trails, and just 15 minutes to Middletown, where you'll find shopping, dining, and easy access to highways, buses, and the train to NYC. With only a 1.5-hour drive to many NYC locations, it’s an ideal blend of rural tranquility and commuter convenience. Don’t miss this opportunity to own a rare combination of space, privacy, and location. Schedule your private tour today!
1987 | 3 | 1 | 1,908 sqft.