Middletown Homes with Assigned Parking features

Welcome to Middletown, a charming city nestled in the heart of Orange County, New York! Known for its rich history, vibrant community, and picturesque landscapes, Middletown offers a perfect blend of suburban tranquility and urban convenience. With its strategic location just 70 miles northwest of New York City, residents enjoy easy access to the hustle and bustle of the Big Apple while being able to retreat to their peaceful home environment.

Middletown is renowned for its diverse neighborhoods, each boasting unique character and charm. From historic homes that echo the city's storied past to modern developments that cater to contemporary lifestyles, you'll find a variety of options to suit your preferences. One of the key features of homes in this delightful area is the availability of assigned parking. This invaluable amenity ensures that you’ll always have a secure and convenient place to park your vehicle, alleviating the stress often associated with city living.

In addition to its residential appeal, Middletown is surrounded by stunning natural beauty, with parks and recreational areas offering a plethora of outdoor activities. The city is also home to a thriving cultural scene, with local theaters, art galleries, and community events that foster a strong sense of belonging.

Whether you're a first-time homebuyer, looking to upsize, or seeking a serene retreat, Middletown's homes with assigned parking provide the perfect foundation for your next chapter. Come explore the possibilities and discover why so many choose to call this vibrant city home!

Newest Middletown Homes with Assigned Parking features

$495,000

3 Beds ⋅ 3 Baths ⋅ 1027934 MLS

Welcome to this beautifully maintained 2,500 sq. ft. townhouse in the desirable Woodside Knolls community. This spacious home offers 3 bedrooms, each featuring a walk-in closet, and 2.5 bathrooms. The open-concept floor plan seamlessly connects the living area and modern kitchen, creating an inviting space for everyday living and entertaining. Additional features include a two-car attached garage and access to community amenities, including a clubhouse, swimming pool, basketball court, and tennis courts. Conveniently located near schools, parks, shopping, dining, and major commuter routes, this home offers a comfortable lifestyle in a well-established community.

58 Cobblestone Lane, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ 1029712 MLS

Welcome home to this beautifully maintained 2-bedroom, 1.5-bath condo offering the perfect blend of comfort and convenience! Featuring gorgeous wood flooring on the first level, new carpeting in the second level with spacious primary bedroom, walk-in closets in both bedrooms, updated bathrooms with beautiful vanities and tiles. Enjoy a functional layout in a location that's hard to beat—just minutes from shopping, dining, and everyday conveniences. Whether you're a first-time homebuyer, downsizing, or looking for a great investment opportunity, this move-in-ready condo is one you won't want to miss! Call today for more details or to schedule your private showing!

49 Jimal Drive, Middletown

$333,000

2 Beds ⋅ 3 Baths ⋅ 1020170 MLS

Modern Comfort & Lake Access – The Best of Waters Edge! Welcome to this beautifully maintained 2-bedroom, 2.5-bath condo in the highly desirable Waters Edge community. Offering the perfect blend of peaceful lakeside living and modern convenience, this home features a bright, open floor plan designed for easy living. Most of the windows have been replaced, enhancing energy efficiency and bringing in abundant natural light. The main level offers a spacious eat-in kitchen, formal dining area, and a sun-filled living room with sliding glass doors leading to a private rear patio—ideal for relaxing or entertaining. A convenient half bath completes the first floor. Upstairs, soaring vaulted ceilings create an open, airy atmosphere. The primary suite features a large walk-in closet and a private ensuite bath, while the second bedroom and an additional full bath provide an ideal setup for guests, family, or a home office. Enjoy all that Waters Edge has to offer, including scenic lake access, beautifully maintained grounds, and a convenient location close to shopping, restaurants, schools, and major commuter routes.

5 Kendal Lane, Middletown

$349,000

2 Beds ⋅ 3 Baths ⋅ 1018987 MLS

Beautifully maintained end-unit townhouse in the highly desirable Water's Edge community! This move-in-ready 2-bedroom, 2.5-bath home offers a bright, open layout with a spacious foyer, updated kitchen featuring newer appliances, a large living room with new sliding glass doors leading to a private patio, and a convenient first-floor powder room. Upstairs, the primary suite features cathedral ceilings, a walk-in closet, and a private bath. A spacious second bedroom and full bath complete the second floor. Recent updates include Low-E energy-efficient windows (2023) and a new smart hot water heater. Enjoy assigned parking plus ample guest parking. The HOA covers snow removal, landscaping, exterior maintenance, garbage, and recycling for easy, low-maintenance living. Conveniently located just off Route 211 and minutes from Route 17/I-86 and I-84, you'll be close to shopping, restaurants, the train station, Garnet Health Medical Center, LEGOLAND New York Resort, Resorts World Catskills, and Woodbury Common Premium Outlets. Move right in and enjoy everything this wonderful community has to offer!

15 Kendal Lane, Middletown

$151,900

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

$369,900

3 Beds ⋅ 3 Baths ⋅ 1012400 MLS

Welcome to Buttonwood Hills! This spacious 3-bedroom, 2.5-bath townhouse offers comfortable, low-maintenance living in one of Middletown's most convenient locations. Featuring a bright and functional layout, the main level includes a generous living room, dining area, updated kitchen, convenient half bath, and in-unit laundry. Upstairs, you'll find a spacious primary bedroom along with two additional bedrooms and full baths, providing plenty of room and versatility. With renovated kitchen and updated bathrooms, this home is truly move in ready. Community amenities include an unground outdoor pool, clubhouse and recreational areas. Ideally situated just minutes from shopping, restaurants, schools, parks, Garnet Health Medical Center, Touro College, SUNY Orange and all major commuter routes including I-84 and Route 17, this home combines convenience, affordability, and easy condominium living. Whether you're a first-time buyer, downsizing, or looking for an investment opportunity, this Buttonwood Hills townhouse is ready to welcome you home.

202 Concord Lane, Middletown

$399,000

2 Beds ⋅ 3 Baths ⋅ 1011416 MLS

Beautiful Townhouse in Fairways at Wallkill! Enjoy maintenance-free living in this desirable Fairways community townhouse. Conveniently located near major highways, shopping, and Orange Regional Medical Center, this home features 2 bedrooms, 2.5 bathrooms, a spacious living room, and a bright private balcony overlooking the pool. Residents have access to outstanding amenities including a clubhouse, fitness center, library, billiards room, and heated swimming pool. HOA services include landscaping and snow removal, providing ease and convenience year-round. A perfect combination of location, comfort, and community amenities—schedule your showing today!

19 Putters Way Unit #6, Middletown

$245,000

2 Beds ⋅ 2 Baths ⋅ 1010150 MLS

Prime Location in Sought-After Hillside Village – Goshen School District! Welcome to this first-floor, end-unit 2-bedroom, 2-full bath condo in the desirable gated community of Hillside Village. Offering the convenience of one-level living, this home features a galley kitchen with an abundance of cabinetry, and a spacious living room with sliding glass doors leading to a private patio—perfect for relaxing or enjoying your morning coffee. The original dining area has been thoughtfully converted into a versatile home office or den, creating flexible living space to suit today's lifestyle. The primary suite offers a walk-in closet and a private ensuite full bath, while the second bedroom is ideal for guests or additional workspace. A large-capacity stackable washer and dryer are conveniently located in the hallway, along with additional storage. Three wall air-conditioning units and ceiling fans help keep the home comfortable throughout the warmer months. The low HOA fee includes lawn care, snow removal, water, sewer, and garbage service, allowing for low-maintenance living. One assigned parking space and ample guest parking add to the home's convenience. This property presents an excellent opportunity for buyers looking to personalize a home to their own taste. While it does require updating and TLC, it offers tremendous potential and is being sold As Is, including all appliances. Ideally situated in an excellent commuter location, you'll be just minutes from Metro-North, Garnet Health Medical Center, medical offices, shopping, the Galleria at Crystal Run, restaurants, and grocery stores. Whether you're a first-time buyer, downsizing, or seeking an investment opportunity, this condo offers outstanding value in a highly desirable location. The low HOA fee covers lawn care, snow removal, water/sewer, and garbage services. The home does need updating and TLC—perfect for buyers ready to bring their vision and create the home of their dreams. Home and appliances are being sold “As Is.” Enjoy a peaceful setting with one reserved parking space and ample guest parking. This excellent commuter location is close to the Metro-North train station, Garnet Health Medical Center, medical offices, shopping, the Galleria Mall, restaurants, and grocery stores.

100 Hillside Drive Unit #C6, Middletown

$160,000

1 Beds ⋅ 1 Baths ⋅ 1010316 MLS

Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has pass through for more of an open floor plan, plus dining area. Bathroom was updated with new tub, vanity, flooring and tile as well. Large bedroom with dual closets and nice sized windows for lots of natural light. Beautiful new vinyl low maintenance flooring throughout. Navien energy efficient ON DEMAND heat and hot water system in place. Utility room to house the washer and dryer in kitchen.

226 Concord Lane, Middletown

$275,000

2 Beds ⋅ 3 Baths ⋅ 1010447 MLS

Welcome to 11 Jordan Lane, Middletown, NY. This 2-bedroom, 2-bathroom condo offers a practical floor plan and a convenient location close to shopping, dining, schools, healthcare facilities, and major commuter routes. With strong potential and a desirable location, the property presents an excellent opportunity for investors seeking immediate rental income or buyers looking to add value through future updates and improvements. The unit features spacious living areas, a functional kitchen, and bedrooms. Being sold as-is. Schedule your showing today and explore the possibilities this property has to offer.

11 Jordan Lane, Middletown

$285,000

2 Beds ⋅ 2 Baths ⋅ 990896 MLS

Well-maintained 2-bedroom, 2-bath condo in the Deer Run Community with an open layout and good natural light. Building entry with controlled access and interior access to the second-floor unit. The living and dining areas are combined and connect to a galley kitchen with a pass-through opening. The primary bedroom features a walk-in closet and a private full bathroom. New carpet was installed in 2025. In-unit washer and dryer. Community amenities include a clubhouse, swimming pool, and tennis court. Lawn care and snow removal are included. Additional highlights include assigned parking and a designated 12' x 11' locked storage unit. Conveniently located near shopping, dining, parks, and with easy access to highways.

66 Deer Ct Drive, Middletown

$259,000

2 Beds ⋅ 2 Baths ⋅ 982111 MLS

An exceptional opportunity for homeowners and savvy investors, this sun-drenched, southeast-facing condo is located in one of Middletown’s rare communities with NO rental restrictions. Experience the comfort of two-level living with a thoughtful layout featuring a spacious living room on the main floor and private bedrooms upstairs. This home offers ultimate peace of mind with a Boiler and Water Heater both newly installed in 2019. Enjoy the convenience of dual entrances; the main access is situated on the upper street-level for easy entry. Residents enjoy premium community amenities including a swimming pool and clubhouse, perfect for relaxation and social gatherings. The property includes one assigned parking space with plenty of visitor parking available on the freshly paved driveway and lot. The HOA provides a truly low-maintenance lifestyle by covering water, snow removal, trash collection, and common area maintenance. Strategically located with easy access to major highways, this move-in-ready home perfectly balances modern convenience with unlimited investment potential.

129 Concord Lane, Middletown

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