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

$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

$337,000

2 Beds ⋅ 3 Baths ⋅ 1047370 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

$215,000

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

$328,000

3 Beds ⋅ 3 Baths ⋅ 1044127 MLS

Rare opportunity in the sought-after Spring Hollow community! This very well-maintained 3-bedroom home offers a desirable and hard-to-find layout with 2 full baths and a half bath. Set on an elevated, quiet lot with a south-southeast exposure, the home enjoys beautiful lake views and a peaceful setting. The inviting living area features a wood-burning fireplace, while the updated kitchen offers newer cabinetry, appliances, and flooring. Thick, comfortable carpeting adds warmth throughout the home. Upstairs, all three bedrooms and two full bathrooms are conveniently located on the same level. A bright open area near the staircase, enhanced by a window and skylight, provides an ideal spot for a home office, desk, reading nook, or study area. A convenient outdoor storage area provides useful extra space for seasonal items, tools, and more. Residents also enjoy access to the community pool and clubhouse. Conveniently located near shopping, dining, and major highways, this move-in-ready home combines a rare layout, scenic views, community amenities, and an excellent location.

43 Brick Pond Road, Middletown

$289,000

2 Beds ⋅ 2 Baths ⋅ 1041811 MLS

Welcome to the beautifully maintained Clemson Park complex. Upon entry you'll walk into the spacious, well-lit Living Room. This home also features a Formal Dining Room and Eat In Kitchen. You'll be able to access the balcony through the sliding glass doors in the living room to kick-back and relax on the deck. The Primary Bedroom offers his/her closets as well as a Primary Bathroom with an in-unit washer and dryer. Ample sized 2nd Bedroom offers plenty of space for guests or an office. The unit is bright and welcoming with plenty of natural sunlight. The clubhouse, community pool, and additional storage space are well maintained and within walking distance. As you walk through the complex you'll notice beautiful grass, green trees, and an overall peaceful atmosphere. Easy access to I-84 and Route 17. Make it yours!

63 Sycamore Drive Unit #63, Middletown

$314,000

2 Beds ⋅ 3 Baths ⋅ 1043648 MLS

Prime Location & Neighborhood Commuter Convenience: Minutes from Route 17 (Future I-86), Interstate 84, and the Middletown Metro-North train station, providing a straightforward commute toward NYC and Westchester. Proximity to Key Amenities: Close to Garnet Health Medical Center, SUNY Orange, and the Route 211 commercial corridor (major shopping centers, dining, and grocery options). Quiet Residential Setting: Situated in an established, quiet residential subdivision in the Town of Wallkill / Middletown area with minimal through-traffic. Property & Layout Highlights Spacious Multi-Level Living: Features a bright, open floor plan with high ceilings and excellent natural light throughout the primary living areas. Functional Kitchen & Dining Flow: Designed for entertaining with seamless connection between the kitchen, dining space, and living room. Generous Bedroom Suites: Offers well-proportioned bedrooms, including a primary suite with dedicated closet storage and private bath access. Flexible Lower Level / Basement Space: Provides ample square footage for a family room, home office, gym, recreation area, or additional storage. Outdoor & Practical Features Usable Yard Space: Features a manageable, private backyard and deck area ideal for outdoor dining and relaxation. Attached Garage & Driveway: Built-in garage parking with private driveway space for multiple vehicles. Municipal Utilities: Connected to municipal water and sewer services, eliminating private well or septic maintenance concerns.

35 Lexington Way, Middletown

$329,900

2 Beds ⋅ 2 Baths ⋅ 1043166 MLS

Welcome to Clemson Park! Discover this beautifully updated and well-maintained townhouse in the desirable Clemson Park community. Featuring 2 bedrooms and 1.5 bathrooms, this home offers a spacious open floor plan perfect for both everyday living and entertaining. The bright living and dining area includes plush, well-maintained carpeted floors and sliding glass doors that open to a charming balcony—perfect for enjoying sunny days in comfort. The kitchen boasts ample cabinetry, countertops, electric cooktop, and a newly installed refrigerator and microwave. A large closet under the stairs provides convenient storage, while the updated half bath on the main level adds both modern style and convenience. Upstairs, the primary bedroom features wall-to-wall closets and direct access to the full bath. The main bathroom includes a whirlpool tub, two linen closets, and an in-unit laundry closet. The second bedroom offers generous space, soft carpeting, and versatility. Also included are one indoor parking spot in the shared garage, an additional parking space directly in front of the garage, and a dedicated storage unit located on the ground floor. Enjoy carefree living with all the amenities this sought-after community provides—just minutes from supermarkets, restaurants, the Galleria Mall, I-86, I-84, and more. Don’t miss your chance—this one won’t last!

50 Sycamore Drive Unit #50, Middletown

$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

$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

$146,900

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

$349,000

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

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