Middletown Homes for Sale

Welcome to the vibrant community of Middletown, NY, nestled in the picturesque Orange County. Known for its rich history and diverse culture, Middletown offers residents a delightful blend of suburban charm and urban convenience. One of the standout features of this thriving city is its exceptional school district, which is dedicated to providing a high-quality education for all students.

The Middletown City School District is renowned for its commitment to academic excellence and holistic development. With a variety of educational programs, dedicated staff, and a focus on student engagement, the district aims to prepare young minds for future success. Families can take pride in the array of extracurricular activities, advanced placement courses, and special education services that cater to the diverse needs of its student population. The schools are equipped with modern facilities and technology, fostering an environment conducive to learning and growth.

As you explore the real estate opportunities in Middletown, you'll find a range of homes for sale that cater to various lifestyles and budgets. From charming single-family residences to modern townhomes, the housing market in Middletown is vibrant and diverse. Whether you're a first-time buyer or looking to upgrade, you’ll discover properties that not only meet your needs but also offer proximity to top-rated schools, parks, and community amenities.

Living in Middletown means embracing a community where education, family, and quality of life are prioritized. Explore the homes for sale today and take the first step towards making this wonderful city your new home!

Newest Middletown Homes for Sale

$579,000

3 Beds ⋅ 3 Baths ⋅ 1050855 MLS

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 area and 3 bedrooms, including the master suite with an en-suite bath. Central A/C and hardwood floors throughout. A detached 2-car garage is also included. Additional Information: ParkingFeatures:2 Car Detached,

30 Daly Road, Middletown

$380,000

3 Beds ⋅ 3 Baths ⋅ 1050843 MLS

Welcome to this beautifully updated and well-maintained single-family home, featuring original hardwood floors, updated kitchen and bathrooms, and a spacious layout. The first floor offers a large living room with a fireplace, formal dining room, eat-in kitchen with access to the backyard, and a full bathroom. Upstairs, you’ll find three generously sized bedrooms and a full hallway bathroom. The finished walk-up attic provides additional flexible living space, while the finished basement includes a laundry area, half bathroom, utility room, and workshop/storage space. Enjoy a detached garage, enclosed backyard, and inviting front and back porches. Conveniently located near schools, shopping, and major highways, this home offers comfort, character, and convenience.

11 Gardner Avenue, Middletown

$549,900

2 Beds ⋅ 3 Baths ⋅ 1049692 MLS

Enjoy the ease of main-level living with the bonus of a beautifully designed second floor in Wildflower at Wallkill, a gated 55+ active-adult community. Offering approximately 2,400 square feet, this spacious two-bedroom, two-and-a-half-bath home features an open, comfortable floor plan designed for both everyday living and entertaining. The main level welcomes you with generous living and dining areas filled with natural light and custom trim. At the heart of the home, the kitchen features granite countertops, custom backsplash, abundant cabinetry and an impressive nine-foot island with plenty of room for seating. Just beyond, a comfortable family room with a natural gas fireplace creates a warm gathering space and flows easily into the kitchen. Also located on the main level is the primary bedroom suite, offering the convenience of true one-level living. Upstairs, guests can enjoy their own private area with a second bedroom, full bath and a versatile flex space—perfect for a sitting area, home office, hobby space or quiet retreat. The private rear patio provides a lovely spot for morning coffee, gardening or relaxing outdoors. An attached two-car garage adds everyday convenience. Life at Wildflower at Wallkill extends well beyond the front door. Residents enjoy a gated community with indoor and outdoor pools, clubhouse, tennis and pickleball courts, exercise classes, organized trips and an active calendar of social activities. Shopping, restaurants, medical offices and everyday conveniences are all just minutes away.

6 Cyprus Drive, Middletown

$369,000

2 Beds ⋅ 2 Baths ⋅ 1050156 MLS

COMING SOON! Priced for a Quick Sale! This move-in-ready home offers 1,922 square feet of comfortable living space, featuring 2 bedrooms and 2 full bathrooms, plus a potential third bedroom or bonus room on the lower level. Enjoy easy, low-maintenance living with no HOA, a one-car garage, and low taxes. Recent updates include kitchen cabinets, newer furnace and hot water heater, giving you added peace of mind. With a practical layout, plenty of space, and an attractive price point, this is a fantastic opportunity for a first-time buyer, downsizer, or anyone looking for affordable and easy living. So Close to All Shops, Highways, Hospital and Yet Tucked Away. Don’t miss this one—priced to sell quickly!

3 Moriah Lane, Middletown

$550,000

4 Beds ⋅ 3 Baths ⋅ 1049857 MLS

Beautiful home for Sale that features 4 bedrooms with 2.5 baths in a desirable area of Middletown just minutes from Orange County Community College. Do NOT let the outside fool you as this home is bigger than expected inside as it has many finished levels! Newly remodeled and ready for its final touches. Open floor layout from Living room to dining room & kitchen all with newly stained hardwood floors. The kitchen features new cabinets, granite counters and new stainless steel appliances right out the box! 4 bedrooms are located on the upper level, one which is a Suite with its own private bath and shower. Completely remodeled tiled bath with new toilet vanity & sink. A 2nd full bathroom with a tub AND tiled shower completes the upper floor. Again all new top to bottom! A finished lower level offers a Family room, office, and a 3rd half bath along with a laundry room with a new washer & dryer! So much open space is found in this level ideal for an oversized family room, entertainment area, office or workout room. The basement is ALSO finished adding more than enough storage space if it’s needed. Nice size yard that just needs to be cleaned up ideal for gathering & entertaining. Grill and enjoy morning coffee right off the newly pavered patio!!! Plenty of parking along with a 2 car garage. Among some of the upgrades this home offers are the new roof, baths, kitchen, new mechanicals and more! Close proximity to Schools, Colleges, Touro Medical, Garnet Health, and shopping. Call and make this house your home! (AS-IS SALE)

44-50 Ingalls Street, Middletown

$465,000

3 Beds ⋅ 1 Baths ⋅ 1020678 MLS

Welcome to this charming Middletown home offering classic character, comfortable living, and great curb appeal. The inviting covered front porch sets the tone as you enter a home filled with warmth and natural light. The spacious kitchen features an abundance of cabinetry, ample counter space, and stainless-steel appliances, providing plenty of room for everyday cooking and entertaining. Outside, enjoy a generous front lawn and private driveway with convenient off-street parking. Ideally located in Middletown with easy access to shopping, dining, schools, parks, and major roadways. Whether you're looking for a place to call home or an opportunity to make it your own, this property is ready to welcome its next owner. Schedule your showing today!

13 Columbia Avenue, Middletown

$510,000

4 Beds ⋅ 3 Baths ⋅ 1049537 MLS

Welcome to a move-in ready, three-story home designed for easy & comfortable living. The open floor plan feels bright and spacious, with freshly primed walls, updated lighting, and durable flooring that stands up to daily life. You will appreciate practical features like a dedicated laundry room and plenty of closet space for organization. The kitchen comes fully equipped with new cabinets and brand new stainless steel appliances. Sliding glass doors connect the interior to awesome outdoor spaces, including a front porch, back deck, and upper balcony. This home offers great style, real comfort, and low-maintenance living at an affordable value!

326 North Street, Middletown

$599,900

3 Beds ⋅ 2 Baths ⋅ 1047583 MLS

Welcome to 53 Highland View Place! Built in 2018 and situated on a spacious 3.5-acre lot, this beautiful 1,839 sq. ft. ranch offers modern construction, comfortable living, and incredible potential for future expansion. The bright, open-concept layout creates a spacious and inviting feel, perfect for both everyday living and entertaining. The home features municipal water and sewer, natural gas, central air conditioning, and an attached two-car garage. A full unfinished basement provides plenty of storage and even more possibilities for the future. One of the home's standout features is the upper level, offering approximately 843 sq. ft. of space, including two large unfinished bonus rooms ready for your vision. Finishing this area offers the potential to add significant additional living space and create a home with **over 2,500 sq. ft. of finished space**! Whether you envision additional bedrooms, a home office, playroom, gym, or bonus space, the possibilities are endless. Located on 3.5 acres in a beautiful newer neighborhood surrounded by attractive homes, this property offers the space of a large lot while still enjoying a neighborhood setting. Move in and enjoy it today while having tremendous room to grow in the future. Don't miss this one!

53 Highland View Place, Middletown

$899,900

4 Beds ⋅ 4 Baths ⋅ 1048837 MLS

Set on a private, wooded one-acre property in Middletown, this remarkable mid-century modern residence offers a rare opportunity to own a home designed and personally occupied by renowned local architect Dennis Jurow. With more than 4,000 square feet of living space, the home reflects Jurow’s distinctive architectural vision through its dramatic design, abundant natural light, and seamless relationship with the surrounding landscape. Inside, soaring ceilings and expansive walls of glass create an open and airy atmosphere, while triangular clerestory windows and striking architectural lines add visual interest throughout. Ten sliding glass doors bring the outdoors into nearly every aspect of the home, providing an effortless connection to the property’s mature trees, private grounds, and peaceful setting. The residence has been lovingly preserved, allowing many of Jurow’s original design elements to remain part of the home today. Custom built-ins, distinctive tile flooring, original lighting, sunken gathering spaces, and thoughtfully arranged living areas highlight the character and craftsmanship of the original design. One of the home’s most unique features is Jurow’s original architectural studio, a space that can continue to serve as a creative workspace or easily function as a private office or professional suite. An additional wellness room or office offers further flexibility for work, relaxation, or everyday living. The outdoor spaces are equally inviting. Surrounded by mature trees and natural landscaping, the property offers multiple areas for entertaining and relaxing, along with an in-ground pool that creates a private retreat during the warmer months. The home’s zoned living areas also allow for efficient heating and cooling while providing comfort throughout its expansive footprint. Distinctive, thoughtfully preserved, and rich with local architectural history, this is a residence unlike the typical offering. From its signature mid-century details to its extraordinary connection between indoor and outdoor living, the property presents a unique opportunity to become the next steward of one of Dennis Jurow’s most personal designs.

19-21 Lincoln Terrace Unit #19, Middletown

$380,000

3 Beds ⋅ 3 Baths ⋅ 1048889 MLS

Welcome to 13 Old Anvil Lane, a conveniently located Middletown home offering comfort, flexibility, and easy access to everything the area has to offer. With several updates already completed, the home feels fresh and move-in ready while still leaving room to add your own personal touch. Inside, you’ll find a comfortable and functional layout designed for everyday living. Plenty of bedrooms and bathrooms for the whole family. One of the home’s standout features is the full walk-out basement, offering excellent potential for additional living space, a recreation room, home office, gym, workshop, or extra storage. A private fenced-in yard is easy to maintain but offers additional gathering space for friends, family, and pets. Located just minutes from shopping like the Galleria Mall and Route 211, dining, Garnet Hospital, schools, major highways (I-84, 17/ I-86), gyms, and train transportation, this property makes commuting and daily errands exceptionally convenient. Whether you're looking for your first home, additional space, or a property in a highly accessible location, 13 Old Anvil Lane offers a great combination of value, versatility, and convenience in the heart of the Middletown area.

13 Old Anvil Lane, Middletown

$350,000

5 Beds ⋅ 2 Baths ⋅ 1046630 MLS

A charming Cape Cod-style home set on a spacious 1-acre lot in the Town of Wallkill. This 5-bedroom, 2-bath home offers a classic layout with plenty of space and opportunity to make it your own. The main level features a comfortable blend of living and functional spaces, while the upper half-story provides additional bedrooms and living space. For investors, this property presents a great opportunity to purchase with existing tenants in place, providing immediate rental potential. For owner-occupants or buyers looking for flexibility, the property can also be delivered vacant at closing. A full, unfinished basement offers abundant storage and utility space, while the attached 2-car garage provides convenient parking and additional storage. Enjoy the outdoors from the covered front porch and expansive yard, offering plenty of room for gardening, recreation, or simply relaxing. The home is equipped with natural gas hot-water heating, private water and sewer, and is situated within the Middletown Central School District. Conveniently located in the Town of Wallkill with easy access to shopping, dining, major roadways, and nearby amenities. A wonderful opportunity to own a spacious Cape Cod on a generous 1-acre property, whether you're looking for an investment property with tenants already in place or a home that can be delivered vacant and personalized to your needs.

580 Route 17M, Middletown

$385,000

2 Beds ⋅ 2 Baths ⋅ 1047462 MLS

Welcome to this move-in ready 2-bedroom, 2-bath townhouse with NO HOA fees! This well-maintained home has been freshly updated inside and out, featuring fresh interior and exterior paint, a freshly painted deck, brand-new flooring on the main and lower levels, and new carpeting in the upstairs bedrooms. The bright eat-in kitchen offers ample cabinet space and plenty of natural light. The inviting living room features a cozy fireplace and opens directly to a private deck overlooking a peaceful wooded setting—perfect for relaxing or entertaining. Upstairs, the primary bedroom features a private en-suite full bath and its own balcony, creating a comfortable retreat with a private outdoor space. Additional highlights include in-home laundry and a one-car garage. Conveniently located near shopping, dining, major highways, bus transportation, and commuter train service to NYC. Move right in and enjoy the comfort and convenience of townhouse living without the added expense of HOA fees!

22 Mayer Drive, Middletown

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