Middletown Homes with Private Parking features

Welcome to Middletown, NY – a vibrant city nestled in the heart of Orange County, where community spirit meets educational excellence. Known for its rich history and picturesque landscapes, Middletown is not just a place to live; it's a place to thrive. One of the standout features of this charming locale is its highly regarded school district, which is dedicated to fostering an enriching environment for students of all ages.

The Middletown School District is renowned for its commitment to academic achievement, offering a diverse range of programs designed to cater to the varied interests and needs of its students. With a focus on innovation and inclusivity, the district boasts award-winning educators and state-of-the-art facilities, ensuring that every child has the opportunity to succeed. Families are drawn to the area not only for its educational offerings but also for the sense of community that permeates the school environment.

In addition to its exceptional schools, Middletown offers a variety of homes that come with the highly sought-after feature of private parking. Imagine the convenience of having your own dedicated space to park your vehicle, eliminating the stress of street parking and giving you peace of mind. Whether you’re looking for a cozy starter home or a spacious family residence, the real estate options in Middletown with private parking are sure to meet your needs.

Embrace the charm of Middletown, where quality education, community, and comfortable living converge. Discover your dream home today and experience all that this delightful city has to offer!

Newest Middletown Homes with Private Parking features

$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

$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

$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

$545,000

3 Beds ⋅ 3 Baths ⋅ 1037842 MLS

A rare opportunity in The Meadows! This expanded three-bedroom, 2 ½-bath raised ranch offers approximately 2,508 sq. ft. on more than half an acre. A 12-foot addition spanning both levels provides substantially more living space than many homes in the development. Set on a desirable corner lot facing woods, it offers a peaceful, secluded feel while remaining just five minutes from major shopping, Galleria Mall, dining, highways, and Garnet Medical Center. The open-concept main level features a chef-inspired kitchen with abundant wood cabinetry, hardwood flooring, a generous 8' x 3' peninsula, a newer induction convection range, and a second convection wall oven. Recessed lighting throughout creates a bright, modern environment. The fully finished walk-out lower level offers 1 ½ baths, multiple living areas, baseboard heat, luxury vinyl plank flooring, laundry alcove, and generous storage. A mirrored home gym is ideal for fitness, yoga, dance, or an art studio. The finished addition offers space for a playroom or family room, plus two flex rooms with exterior access-perfect for office, guest room, and/or mudroom. The fully fenced, level backyard is a private retreat with dramatic natural boulders, impressive multilevel stone patios, an electrified 6-foot granite outdoor island, and an included 8-foot Master Spa hot tub. Additional highlights include owned solar panels, two EV chargers, premium cedar-shake-style vinyl siding, updated windows and doors, and a roof with 50-year shingles. Enjoy The Meadows pool, clubhouse, tennis/pickleball, and playgrounds. This distinctive home must be seen to be fully appreciated.

2 Harvest Hill Lane, Middletown

$489,999

3 Beds ⋅ 4 Baths ⋅ 1009337 MLS

This beautiful 3 bed 3 1/2 bath townhome is nestled in the heart of Middletown with so much to offer and just minutes to transportation to and from NYC. Upon entering you'll find beautiful hardwood floors throughout the first floor. An open floor plan including a sun drenched living room with a fireplace, full glass door leading to a very spacious deck for outdoor grilling or relaxation. Just opposite the living room is an amazing kitchen with granite countertops, an island and stainless steel appliances. Upstairs you'll find a large primary bedroom equipped with a custom California closet setup and a gorgeous en-suite. The second floor is finished off by two large bedrooms, a full bathroom and a laundry room. The lower level is fully finished to be used however you desire and it walks out to a large patio and a beautifully manicured lawn leading to an area of undeveloped land that makes it quite peaceful and relaxing. Maple Fields is located 5-7 min near shops, parks, restaurants, and major highways 84/17! Offering tranquility and privacy and so much more, don't miss out on the opportunity to own this beauty. Additional Information: Amenities:Soaking Tub,Storage,ParkingFeatures:2 Car Attached,

93 Meadow View Drive, 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

$399,000

3 Beds ⋅ 2 Baths ⋅ 1029395 MLS

Tucked into one of Middletown's established neighborhoods, 30 Chestnut Avenue is a home that effortlessly blends comfort, style, and convenience. From the moment you step inside, you'll appreciate the bright, open floor plan where natural light pours through the windows, creating inviting spaces designed for both everyday living and memorable gatherings. The heart of the home is the beautifully updated kitchen, featuring sleek stainless steel appliances, ample cabinetry, and a seamless flow into the living and dining areas. Rich dark hardwood floors add warmth and sophistication throughout, complementing the home's timeless appeal. Outside, discover your own private retreat. The shaded patio invites slow mornings with coffee, summer barbecues, and peaceful evenings surrounded by the privacy of a tree-lined backyard. It's a space made for relaxing, entertaining, and enjoying every season. The neighborhood itself is one of the home's greatest assets. Quiet streets encourage evening strolls, morning walks, and friendly conversations with neighbors, while parks, shopping, restaurants, and everyday conveniences are all just minutes away. For commuters, the location offers exceptional accessibility with easy access to major highways, nearby public transportation, and a convenient commute to New York City—approximately 70 miles away—making it easy to enjoy the best of both worlds: a peaceful suburban lifestyle with the city within reach. Whether you're hosting holidays, creating lifelong memories with family, or simply enjoying a quiet evening on the patio, 30 Chestnut Avenue is more than a house—it's a place to truly feel at home.

30 Chestnut Avenue, 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

$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

$699,000

4 Beds ⋅ 4 Baths ⋅ 984442 MLS

Steeped in character and timeless appeal, this 1930 Colonial invites you in with its striking stone facade and a graceful partial wrap-around porch—an ideal spot to enjoy quiet mornings or unwind at the end of the day. Inside, the home blends classic craftsmanship with modern comfort, featuring rich wooden floors that flow seamlessly throughout the main level. The first floor offers a warm and welcoming layout: a bright living room, an elegant dining room, and an eat-in kitchen equipped with stainless-steel appliances. A convenient half bath adds practicality, while the expansive family room becomes the heart of the home, complete with abundant natural light and a cozy wood-burning fireplace perfect for gatherings. Upstairs, the spacious primary suite feels like a retreat, offering an en-suite bathroom and a generous walk-in closet. Three additional large bedrooms and two more full bathrooms ensure everyone has room to spread out comfortably. A full stand-up attic provides exceptional potential—imagine a game room, additional bedrooms, a studio, or a private office. The possibilities truly are endless. Outside, an outbuilding with electricity opens the door to even more creativity—workshop, hobby space, storage, or a future guest cottage. The long driveway provides ample parking and leads to a two-car garage for added convenience. Located just minutes from shopping and dining, and a short drive to beloved destinations like Bethel Woods, Legoland, and more, this home offers the perfect blend of charm, space, and accessibility with possibilities of investment opportunities being so close to the college or Air B&B. A rare opportunity to own a property with history, character, and room to grow.

571 Route 17M, Middletown

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