Middletown New York homes for sale starting at Fifty Thousand Dollars

$299,000 - Middletown, NY

1031 Main Street Middletown, NY - Discover the timeless charm of this 1930 Craftsman cottage, nestled in a serene setting with a picturesque streamside location. Spanning 1,585 square feet, this inviting home features three bedrooms and now includes two full bathrooms, one of which is a newly added Jack-and-Jill bathroom upstairs, complete with a tub. All rooms are adorned with rich wood details that exude character and warmth. The spacious interior showcases classic craftsmanship and enduring charm. Imagine drifting off to sleep with the soothing sound of the stream outside your bedroom window or enjoying quiet afternoons in the lush backyard. The 3-car garage offers added convenience and the potential to serve as a workshop or hobby space. The nearby village, with its delightful stores, gourmet restaurants, and a swimming hole, is just a stroll away. Additionally, a park located across the street offers an excellent spot for recreation. Belleayre Ski Resort, Hannah Country Club, Catskill Park Hiking Trails, and various local attractions are all within reach. Schedule a showing today and take your first step toward owning a piece of Catskill living!

$292,000 - Middletown, NY

687 Main Street Middletown, NY - Nestled in the heart of a picturesque Catskill Mountain village, this enchanting home is a true gem that seamlessly combines historical charm with contemporary updates. Built in 1869, this residence has stood the test of time. With its delightful front porch, three well-appointed bedrooms, and one and a half bathrooms, this home is perfect for anyone looking to experience the beauty of mountain living while enjoying the conveniences of village life. The property also features off-street parking, a rare find in such a desirable village location. The current owner has made numerous updates to the home, ensuring that it meets the needs of modern living. The new flooring throughout the home adds a creating a seamless flow from room to room. The living area is bright and airy, thanks to large windows that allow natural light to flood the space. The separate dining room offers a perfect setting for family dinners or intimate gatherings. The kitchen is updated with a new oven and dishwasher; plenty of counter space and storage, This charming home boasts three comfortable bedrooms. The primary bedroom is spacious and features ample closet space. The additional bedrooms are well-sized. The home includes 1.5 bathroom. In this prime location, you will find a gourmet food shop, a supermarket, and charming art galleries that showcase local talent. Outdoor enthusiasts will appreciate being just minutes away from hiking trails and swimming spots. In the winter, you’re only 14 minutes from the Belleayre Mountain Ski Center, Farmers' markets, art shows, and seasonal festivals are just a few of the highlights that make this area special. Whether you’re for a year-round residence or a weekend getaway, this home offers the perfect balance of comfort, convenience, and charm. Living in this Catskill Mountain village means embracing a lifestyle that celebrates nature, community, and creativity. The village is known for its friendly atmosphere, where neighbors become friends and community events bring everyone together. The updates made by the current owner ensure that you can move right in and start enjoying everything this wonderful village and surrounding area have to offer.

$279,000 - Middletown, NY

920 New Kingston Road Middletown, NY - Welcome to this cozy cabin nestled in the woods situated in the stunning New Kingston Valley area on a spacious3-acre lot, just 23 minutes from Belleayre Ski Center and 12 mins to the charming village of Margaretville. This charming retreat features a pond, perfect for relaxing and enjoying nature. The covered porch offers a peaceful spot to unwind and take in the surrounding beauty. Step inside to a large living room with a picture window that brings the outdoor inside. Stay warm and cozy on chilly evenings with a wood burning fireplace in the dining room and a propane stove in the living room. This cabin offers three bedrooms, providing plenty of space for family and guests to stay comfortably. Whether you're looking for a weekend getaway or a year-round retreat, this cabin in the woods is the perfect place to escape the hustle and bustle of city life and immerse yourself in the tranquility of nature.

$279,000 - Middletown, NY

2 S Aspen Road Middletown, NY - Opportunity is knocking! Great rental property for investors! Cute townhouse priced to sell. House is being sold As-Is. Tenants in place, Do Not Disturb! Bring all offers.

$269,900 - Middletown, NY

17 N Aspen Road Middletown, NY - This renovated 2-bedroom, 1.5-bath townhouse in Middletown offers a perfect blend of comfort and convenience! The inviting living room, filled with natural light, leads into a modern kitchen with brand-new stainless steel appliances and an adjacent washer/dryer setup. The dining room features a sliding door that opens up to a private fenced-in backyard—ideal for outdoor relaxation or entertaining. Upstairs, enjoy new carpet throughout, with a spacious primary bedroom offering abundant natural light. The second bedroom is also generously sized with plenty of closet space. A full bathroom serves the second floor. One of the standout features of this home is that there’s no HOA and low taxes, helping you save on costs. Located in a lively neighborhood, this townhouse is close to restaurants, shops, parks, and major commuting routes, making it a fantastic choice for anyone seeking both comfort and convenience in a thriving community.

$269,900 - Middletown, NY

147 Ruth Court Middletown, NY - Welcome to this beautifully maintained 2-bedroom, 2-bathroom condo in Middletown! Featuring a spacious and inviting layout, this condo boasts a generously sized primary bedroom with a walk-in closet. Conveniently located close to shops, restaurants, and entertainment, you'll love the ease of access to everything you need. Whether you're relaxing at home or exploring the vibrant local area, this condo offers the perfect blend of comfort and convenience. Don't miss the chance to make it yours!

$267,500 - Middletown, NY

197 Highland Avenue Middletown, NY - **Multiple offer situation. Seller requesting highest, best and final offers 12pm noon, 7/7/2025.** 3 Bedroom, 1.5 Bathroom Old Style Two Story home in Middletown! Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer taxes. Offers with financing must be accompanied by pre-qual letter; cash offers with proof of funds. **Please see agent remarks for access, showing instructions and offer presentation remarks.**

$266,900 - Middletown, NY

299 Highland Ave Extension Middletown, NY - Great investment opportunity or first time home buyer. Spacious 2 bedroom 1 bath home with large living room as well as a full Dining room for family to gather. Ample space in the kitchen with sliding door leading to a deck overlooking the back yard. Upstairs you will find 3 bedrooms with a full bathroom and an extra room which can be an office or extra storage. Plenty of parking and yard to enjoy and entertain.

$259,900 - Middletown, NY

34 Jimal Drive Middletown, NY - Beautifully cared and maintained 2 bedrooms, 1.5 bathrooms townhouhse in the desirable Highland Park Village. From the moment you walk through the door you can see the pride and care the sellers have provided to this unit. Not one thing for you to do, except bring your personal stuff. Laminate floors throughout. Upgraded kitched with stainless steel appliances. Spacious primary bedroom offers 2 walk-in closets. Newly installed glass shower doors for easy care. The Home owners association fees cover lawncare, snow removal, trash, plus water and sewer. Located minutes to supermarkets, Galleria Mall, restaurants, local shops and Garnet Medical Center. 5 minute drive to I86 & I84. 10 minute drive to LegoLand. 15 drive to Resorts Wold Catskills Hotel and Casino.

Middletown, New York listings for sale

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