Middletown Homes with Middletown School district

Welcome to Middletown, New York – a vibrant city nestled in the heart of Orange County, where small-town charm meets modern convenience. With its rich history and scenic landscapes, Middletown offers a unique blend of urban amenities and natural beauty, making it an ideal place to call home.

Middletown is known for its friendly community atmosphere, diverse cultural events, and a variety of recreational opportunities. Whether you're exploring the picturesque parks, enjoying local festivals, or indulging in the culinary delights of the area's restaurants, there’s always something to do. The city boasts easy access to major highways, making commuting to New York City a breeze while allowing residents to enjoy the tranquility of suburban life.

For families considering a move to Middletown, the Middletown School District is a significant draw. Known for its commitment to academic excellence and a wide range of extracurricular activities, the district provides a nurturing environment for students of all ages. Parents can rest assured that their children are receiving a quality education, with dedicated teachers and innovative programs designed to inspire and engage.

The housing market in Middletown is diverse, offering everything from charming historic homes to modern developments. Whether you’re looking for a cozy single-family house or a spacious townhouse, there’s something to suit every taste and budget. With the added benefit of being within the Middletown School District, these homes not only provide comfort but also a sense of community and belonging.

Discover the charm of Middletown, NY, where your dream home awaits in a city that truly has it all!

Newest Middletown Homes with Middletown School district

$390,000

3 Beds ⋅ 3 Baths ⋅ 1049937 MLS

The flooring on both floors of the house was replaced, and the central air conditioning, hot water boiler, dryer, dishwasher, stove, and Robam range hood were all replaced. Property Highlights Peaceful Cul-de-Sac Setting: Situated on Deer Court Drive, offering minimal drive-through traffic, enhanced privacy, and a safe, quiet street environment. Functional Living Space: Features a comfortable, well-proportioned layout designed for modern family living, entertaining, and work-from-home flexibility. Spacious Outdoor Area: Ample yard space ideal for outdoor gatherings, gardening, play areas, or relaxing in a serene natural setting. Turnkey Appeal: A welcoming entryway and curb appeal with well-maintained structural elements and grounds. Neighborhood & Community Advantages Prime Commuter Location: Convenient access to major regional transit corridors, including Route 17 (Future I-86), Interstate 84, and the Middletown-Town of Wallkill Metro-North station for hassle-free travel across Orange County and into New York City. Proximity to Everyday Conveniences: Minutes away from the Route 211 commercial corridor, Galleria at Crystal Run, major retail hubs, supermarkets, medical facilities (including Garnet Health Medical Center), and dining options. Hudson Valley Lifestyle: Close to local parks, hiking trails, golf courses, and farm-to-table markets, offering an ideal blend of suburban convenience and scenic countryside. Strong Community Atmosphere: Established, family-friendly residential neighborhood characterized by well-kept properties, mature trees, and high pride of ownership.

45 Deer Ct Drive, 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

$1,450,000

1047896 MLS

20+ Prime Commercial Acres with 7,000 SF Barn on Route 17M. This 20.10-acre parcel offers endless possibilities for developers, end-users, and investors, sitting along high-traffic Route 17M in the Town of Wallkill. While the original farmhouse is gone, the land is prepped for its next chapter, anchored by a massive 7,000 sq ft outbuilding/barn—ideal for immediate storage, staging, or operational use while site plans are executed. Offering over 680 feet of road frontage on Route 17M, the property boasts excellent exposure, easy access to municipal utilities (water and natural gas on the street), and potential for future subdivision with town approval. Strategically located near major commercial corridors, Interstate 84, and Route 17/I-86, this site supports seamless logistics across Orange County and the Hudson Valley. Zoning & Permitted Land Uses: Zoned ENT-L (Enterprise Light), this district is engineered to encourage flexible commercial, light industrial, and business development. Permitted By-Right & Site Plan Uses: Contractor Yards & Storage Facilities: Ideal for general contractors, landscaping operations, equipment storage, and material yards. Warehousing & Distribution: Light distribution centers, wholesale trade operations, and logistics hubs.Light Industrial & Manufacturing: Clean assembly, light manufacturing, processing, and tech-flex operations.Professional & Corporate Offices: Administrative offices, engineering firms, executive centers, and corporate headquarters.Equipment Repair & Rental: Commercial equipment service, sales, and rental operations. Special Permit & Commercial Possibilities (Subject to Town Board / Planning Board Approval)Commercial / Service Operations: Automotive service establishments, indoor recreational facilities, or trade schools.Commercial Subdivisions: Splitting the parcel into smaller industrial/commercial lots given the 680+ feet of double road frontage. Agricultural / Nursery Operations: Utilizing the vast acreage and existing barn infrastructure for agricultural support, wholesale greenhouses, or farm-market ventures. (Note: Buyers should verify specific footprint limits, setbacks, and special use permit guidelines directly with the Town of Wallkill Planning and Building Department).

686 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

$396,000

4 Beds ⋅ 2 Baths ⋅ 1046390 MLS

Investment Highlights & Key Advantages: 30 Crescent Place, Middletown, NY 10940 Exceptional Cash Flow & High Rental ROI: Configured as a legal, high-demand multi-family property, it commands strong aggregate market rents that deliver an outstanding capitalization rate and cash-on-cash return well above regional single-family averages. 100% Expense Coverage ("Free Living" or Positive Cash Flow): The dual-unit income easily covers the full PITI (principal, interest, property taxes, and insurance) alongside standard maintenance and utility reserves. For an investor, it generates immediate net passive income; for an owner-occupant (house-hacking), the secondary unit subsidizes the mortgage completely, allowing for virtually cost-free living. Strategic, Commuter-Friendly Location: Centrally situated in the heart of Middletown, offering immediate access to Route 17, Interstate 84, Garnet Health Medical Center, SUNY Orange, and Touro College of Osteopathic Medicine. It is also just minutes from the Metro-North commuter rail station and Coach USA bus routes to NYC. Low Vacancy Risk & Sustained Tenant Demand: Orange County’s expanding healthcare, logistics, and higher education sectors drive continuous, year-round rental demand, ensuring fast turnover and reliable occupancy. Built-in Long-Term Appreciation & Value-Add Potential: Multi-family properties in established Hudson Valley submarkets benefit from consistent capital appreciation, inflation-hedging rent growth, and attractive depreciation tax benefits.

30 Crescent Place, 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 assigned parking spots 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!

14 Brick Pond Road, Middletown

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