Middletown Homes under $250,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Middletown and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Middletown Homes under $250,000

$199,000

1 Beds ⋅ 1 Baths ⋅ 1054352 MLS

This well-maintained 1-bedroom, 1-bathroom condo offers comfortable, convenient living with the added benefit of desirable ground-floor access. The functional layout features a spacious living area with direct access to your own private patio. An awning provides welcome shade and makes the patio an inviting extension of the living space. The generously sized bedroom offers plenty of room to create a comfortable retreat, while the convenient one-level layout makes everyday living easy. Whether you're looking for a low-maintenance residence opportunity, this Middletown condo is ready for its next owner!

122 Sycamore Drive, Middletown

$224,000

1 Beds ⋅ 1 Baths ⋅ 1052461 MLS

Investor Alert: Turn-Key Cash Flow in Downtown Middletown!Tucked away at the end of a quiet street, this charming single-family home offers an incredible, immediate investment opportunity. The property features a reliable, long-term tenant already in place, generating a steady $1,600 per month in rental income. The main floor boasts a functional kitchen, living room, formal dining room, full bathroom, and a bonus space perfect for storage. Upstairs, you will find an expansive, oversized bedroom suite that was previously configured as two separate bedrooms—offering excellent flexibility to easily convert it back for increased value. Complete with a generous backyard, remarkably low taxes, and a highly walkable location just minutes from downtown dining, local shopping, and the NYC bus terminal, this property is a powerful addition to any portfolio. Schedule your viewing today!

7 Harding Street, Middletown

$245,000

4 Beds ⋅ 2 Baths ⋅ 1050322 MLS

Calling All Investors & Visionaries! If you’ve been searching for an investment opportunity in a great location, look no further than 191 Wickham Ave. in Middletown! This property offers tons of potential for the right buyer and is ready for someone with the vision and creativity to bring it back to life. Featuring 4 bedrooms, 1.5 bathrooms, a full basement, a detached garage, and a spacious backyard, this home offers plenty of room to create something truly special. The property does require TLC and renovations, but that’s exactly where the opportunity lies. Bring your equipment, your ideas, and your contractor, and transform this house into a beautiful residence or a potentially profitable investment. Centrally located in Middletown, this property provides convenient access to local shopping, dining, schools, transportation, and everything the area has to offer. Low taxes add even more appeal for investors and buyers looking to maximize the potential of their purchase. Whether your goal is to flip the property, renovate it as a rental, or create your own ideal home, the possibilities are worth exploring. With a detached garage, backyard space, and full basement, there’s plenty of opportunity to add value and make this property your own. And let’s talk about the price! Opportunities like this don’t come around every day. If you’re looking for a property where your investment and vision can truly make a difference, this one deserves a closer look. Bring your tools. Bring your ideas. Bring your vision. Don’t miss this opportunity—submit your offer today and bring 191 Wickham Ave. back to life!

191 Wickham Avenue, Middletown

$220,000

1 Beds ⋅ 2 Baths ⋅ 1047409 MLS

Peace, quiet, and effortless maintenance free living await you in this turnkey end-unit condo. Situated along a prime waterfront footprint in the sought-after Spring Hollow community, this home offers an exceptional blend of tranquility and natural beauty. Step out onto your patio to sip morning coffee or host evening gatherings against a backdrop of panoramic pond views and manicured green space. Cross the threshold through a newer Andersen entry door into a bright, cohesive layout framed by upgraded energy-efficient Andersen windows with custom blinds. The heart of the home features a completely renovated kitchen offering an exceptional amount of custom cabinetry, generous counter prep area, and smart storage options. The primary bathroom has been transformed into a true spa-like retreat, featuring custom granite shelving and a massive walk-in tile shower complete with a built-in bench and multiple custom shower heads designed for ultimate relaxation. Move in with complete confidence knowing every major mechanical system in the home has been recently upgraded for maximum energy efficiency and worry-free living! Prime Commuter Location Enjoy resort-style living with an assigned parking spot just steps from your front door, along with full access to community amenities including a sparkling outdoor swimming pool, tennis courts, and a community clubhouse. The HOA handles all exterior maintenance, landscaping, trash, and snow removal so you can enjoy a true lock-and-leave lifestyle. The charming Condo is in a prime commuter location. Ideally located just minutes from Route 17, Interstate 84, Metro-North rail service, local dining, regional shopping hubs, and healthcare facilities. Move right in, relax, and start enjoying the simple life! NOTE: The total square footage does not include the loft. The seller is willing to leave the bed at the buyer's request

14 Brick Pond Road, Middletown

$199,000

1 Beds ⋅ 1 Baths ⋅ 1043527 MLS

Welcome to a low-maintenance lifestyle, minimal utilities, included heat and hot water, generous storage, and a commuter-friendly setting. This condominium is an excellent opportunity for buyers looking for comfort and convenience . Located in a quiet, peaceful neighborhood, this second-floor condo offers a welcome retreat while still being close to varied amenities and transportation options with easy access to multiple major routes, making travel to surrounding communities and employment centers simple and efficient. An eat in kitchen, open floorplan, and spacious primary bedroom (large enough to incorporate an office) with an oversized closet, maximizes living space. Additional storage is a major plus, with a large private storage area in the basement, providing valuable space for seasonal belongings, household items, sporting equipment, and more.

11 Brittany Drive, Middletown

$178,500

2 Beds ⋅ 2 Baths ⋅ 1021767 MLS

This beautiful high end home is located in the desirable Valley View Community. The home is brand new and offers a modern contemporary feel and it is ready to be yours! Ideal commuter friendly location just minutes to the train to NYC. Bright and airy 2 bedroom, 2 bath home with close to 1,000 square feet of space! Gorgeous gourmet kitchen with upgraded cabinets featuring an abundance of beautiful white shaker style cabinets, a hutch cabinet, white Corian countertops, large white subway tile backsplash accentuate the gourmet cooking area, double stainless steel sink, stainless steel kitchen appliances - double door fridge, 5 burner gas stove, dishwasher and microwave. Wide open floor plan flows through the kitchen, dining and living room area which is great for entertaining. The primary bedroom has a walk-in closet and full on-suite bathroom featuring a large walk in shower with seating. You also have an additional nice-sized bedroom and a full guest bathroom located on the opposite side of the home offering privacy. Features include trex composite deck (no maintenance needed), laundry area, sheetrock throughout, vaulted ceilings, recessed lighting, ceiling fan, programmable thermostat, storm door, shed, two car paved driveway and so much more! Convenient commuter location. 70 miles to NYC, less than 10 mins to NYC trains, buses, and tons of shopping and restaurants. Many other floor plan options also available too and more homes that will be ready soon! Start your for home ownership now these will not last long! Financing options available.

412 4TH Avenue, Middletown

$224,900

2 Beds ⋅ 1 Baths ⋅ 1019447 MLS

Charming Cape Cod situated on a private setting surrounded by mature trees and established landscaping. This 2-bedroom, 1-bath home offers a flexible layout with generously sized rooms, abundant natural light, and multiple living spaces to accommodate a variety of needs. The eat-in kitchen features ample cabinetry and workspace, while the additional interior spaces provide opportunities for a home office, hobby area, storage, or entertaining space. Original character and charm can be found throughout the home, offering the perfect opportunity to update and personalize to your style and preferences. Outside, enjoy mature flowering shrubs, stone accents, ample off-street parking, and additional exterior structures offering storage or workshop potential. Bring your vision and discover the possibilities this property has to offer.

32 Tarbell Road, Bloomingburg

$139,000

1 Beds ⋅ 1 Baths ⋅ 1015893 MLS

A fantastic opportunity for first time home buyers, downsizers or investors. Step into this freshly painted, well maintained 1 bedroom condo and experience easy living, low maintenance and community perks including pool and clubhouse. Stainless steel stove and dishwasher are only 3 years old, heating unit 7-8 years old. This complex is conveniently located near major highways and shopping. Enjoy parking only a few steps from your front door.This condo is ready for its new owner. Why rent? Don't miss the chance to secure a living space that's truly your own.

394 Concord Lane, Middletown

$225,000

2 Beds ⋅ 1 Baths ⋅ 1011268 MLS

Opportunity awaits! 2-bedroom, 1-bath one-family home with 2-car garage. Includes a large patio above the garage. Eat in kitchen with refrigerator and gas stove. The seller gutted and renovated the house in 1989. Property requires complete renovation and is being sold as-is. Ideal for investors, contractors, or buyers looking to build equity. Convenient location close to shopping, schools, and commuter routes. Cash or renovation financing preferred. Bring your vision and unlock this property's potential! The electric is on, heat and hot water, municipal water & sewer are hooked up and on. Possible to expand the house above the garage.

45 John Street, Middletown

$199,000

1 Beds ⋅ 1 Baths ⋅ 927923 MLS

Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp, modern interior featuring a cozy stone-accented fireplace, sleek black cabinetry, upgraded appliances, and luxury vinyl plank flooring. The open-concept living space is bright and inviting with fresh finishes, vaulted ceilings, and picture windows that frame the surrounding forested hillside. Step outside and you'll be swept away by the home's crown jewel, a brand-new oversized deck with ample space for grilling, lounging, and soaking up nature’s beauty. Whether you're sipping your morning coffee or enjoying sunset dinners, this deck offers a front-row seat to the tranquil lake just beyond the trees. The lot itself is partly wooded and gently sloped, offering both privacy and unobstructed water views. It's the perfect backdrop for nature lovers, creatives, or anyone seeking a peaceful recharge in the heart of the Hudson Valley. Located less than 90 minutes from NYC, and close to local farms, wineries, hiking trails, and charming small towns, this home is ideal for weekenders, investors, or full-time residents who crave a simpler, quieter lifestyle with modern comforts. Escape the ordinary, 51 S Shore Drive is lake living reimagined.

51 S Shore Drive, Middletown

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

© 2026 TReND. All Rights Reserved.
The data relating to real estate for sale on this website appears in part through the TReND Internet Data Exchange (IDX) program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Real Broker NY LLC participates, and is provided by TReND through a licensing agreement. Real estate listings held by brokerage firms other than Real Broker NY LLC are marked with the IDX icon and detailed information about each listing includes the name of the listing broker.
All information provided is deemed reliable but is not guaranteed. Some properties which appear for sale on this website may no longer be available because they are under contract, have sold or are no longer being offered for sale. The information being provided is for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.