Middletown Homes with Private Parking features

Welcome to Middletown, New York – a vibrant city nestled in the heart of Orange County. Known for its rich history, diverse community, and picturesque landscapes, Middletown offers a perfect blend of suburban charm and urban convenience. With a population that embraces both tradition and progress, this city provides a welcoming atmosphere for families, young professionals, and retirees alike.

Middletown is not just a place to live; it’s a community where you can thrive. The city boasts an array of local parks, shopping centers, and dining options, ensuring that residents have everything they need within reach. With easy access to major highways and public transportation, commuting to nearby cities, such as New York City, is a breeze.

One of the standout features of homes in Middletown is the availability of private parking. In a city where convenience is key, having your own dedicated parking space adds tremendous value and peace of mind. Imagine coming home after a long day to a secure spot waiting just for you, free from the hassle of searching for street parking or dealing with parking restrictions. Whether you’re a busy professional or a parent juggling multiple activities, private parking makes your life just a little bit easier.

If you’re considering a move to Middletown, you’ll find a variety of homes that not only cater to your lifestyle but also provide the comfort and convenience of private parking. Explore the unique neighborhoods and discover the perfect place to call home in this charming city. Welcome to Middletown, where community meets comfort!

Newest Middletown Homes with Private Parking features

$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

$725,000

4 Beds ⋅ 3 Baths ⋅ 1045550 MLS

Tucked away at the end of Roaring Brook Lane in the desirable Owl's Nest subdivision, this contemporary chalet offers a private Catskills retreat on five peaceful acres. Tastefully updated and very well maintained, the home has been enjoyed by the current owners as both a weekend getaway and a successful short-term rental, earning Super Host recognition for the past four years. Step inside through the spacious mudroom--an ideal landing spot for skis, boots, hiking gear, and everything that comes with four-season Catskills living. From here, enter the heart of the home: a bright and welcoming kitchen featuring gleaming granite countertops, stainless steel appliances, abundant workspace, and an oversized island with breakfast bar seating. Designed for both everyday living and entertaining, the open layout makes cooking and conversation feel effortless. Just beyond the kitchen, the dining area flows into the inviting living room, where soaring cathedral ceilings and a fireplace create a warm and cozy gathering space. The primary bedroom is conveniently located on the main level and offers its own fireplace along with a private full bath featuring a soaking tub and separate walk-in shower. A second full bath on the main level provides added convenience for day-to-day living. Upstairs, two additional bedrooms and another full bathroom provide comfortable accommodations for guests. Outdoor living is equally inviting. Unwind in your personal hot tub after a day on the slopes, gather under the gazebo, or enjoy the surrounding woods and fresh mountain air from the wraparound deck. The setting offers a wonderful sense of seclusion while remaining close to some of the Catskills' most popular destinations. Located next to Belleayre Mountain Ski Center in southern Delaware County, the property offers easy access to skiing, hiking, outdoor recreation, dining, shopping, and year-round activities. Phoenicia, Woodstock, and other beloved Catskills destinations are within reach, while New York City is just under three hours away. Whether you are searching for a full-time residence, weekend escape, or established short-term rental opportunity, this Highmount retreat offers privacy, comfort, and four-season Catskills living in an exceptional location.

1270 Roaring Brook 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

$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

$549,900

4 Beds ⋅ 3 Baths ⋅ 1047247 MLS

Welcome to a home that offers the best of both worlds—peace, privacy and a tucked-away setting, while still providing convenient access to local shopping, major roadways and transportation. With generous living space, thoughtful updates and the added benefit of public water and sewer, this beautifully maintained home is ready for its next owner. A charming wraparound porch immediately sets the tone, creating a unique, elevated feel that almost makes you feel as though you are living in a treehouse. Inside, the home offers an abundance of space and a layout that works beautifully for both everyday living and entertaining. The large country kitchen is the heart of the home, with plenty of room for a substantial dining table and direct access through sliding glass doors to the generous rear deck and private backyard. Whether enjoying a quiet morning coffee, hosting a summer barbecue or gathering around the backyard masonry wood-burning firepit, the outdoor spaces are designed to be enjoyed. Upstairs, you will find four bedrooms plus a dedicated office, providing tremendous flexibility for today’s lifestyle. The spacious primary suite features an updated private bathroom and two walk-in closets, with one of those spaces also offering the potential to serve as a private office, dressing room or additional flex space. The home has been exceptionally well cared for, with numerous important improvements already completed. Updates include a new roof in 2020, furnace in 2018, renovated bathrooms in 2022, central air conditioning in 2024, newer appliances, a new washer in 2026, dryer in 2024, new hot water heater in August 2026, fresh interior paint throughout in August 2026, and new flooring in all bedrooms, the laundry room, pantry and primary walk-in closets. A generator is also included, offering additional peace of mind. Outside, the private backyard provides plenty of room to relax and entertain, highlighted by a wood-burning firepit with gas and electric already on site. Spacious, private, beautifully maintained and filled with meaningful upgrades, this home offers a rare combination of peaceful living and everyday convenience. With public utilities, flexible living space, inviting outdoor areas and so many major improvements already completed, this is a property that is truly easy to appreciate. Located in the desirable Pine Bush School District.

106 Freezer 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

$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

$349,000

3 Beds ⋅ 1 Baths ⋅ 1032279 MLS

Beautifully renovated and move-in ready! This bright 3-bedroom, 1-bath home offers 1,092 sq. ft. of comfortable living space, a modern kitchen with granite countertops and new stainless-steel appliances, and an inviting enclosed porch. Enjoy the spacious deck, backyard, large storage shed, and driveway parking. Its efficiently designed layout may help keep heating and cooling costs manageable. Best of all, annual property taxes are currently only $2,238. Conveniently located near shopping, dining, and major roadways—schedule your private showing today!

1630 Goshen Turnpike, Middletown

$599,900

4 Beds ⋅ 3 Baths ⋅ 1026479 MLS

Tucked at the end of a long, paved drive on a quiet country road, this secluded 4-bedroom, 2.5 bath retreat feels worlds away — while still being minutes from everything you need. Five minutes away from major highways and less than ten minutes away from shopping and restaurants. Located in the desirable Pine Bush School District. Step inside to a light-filled first floor featuring maple cabinetry, granite countertops, and a spacious kitchen island — perfect for everyday living and effortless entertaining. Crown molding runs throughout the main level, complemented by a convenient first-floor lavatory and generous living spaces designed for gathering. Upstairs, the primary suite impresses with vaulted ceilings and a private en-suite bath, joined by additional large bedrooms and the everyday ease of second-floor laundry. Outside, an oversized, maintenance-free deck overlooks a large fenced backyard — offering privacy in every direction and space to relax, host, or simply enjoy the quiet. A full basement adds flexible storage or the man cave, gym, or studio you’ve been dreaming of. The attached 2-car garage rounds out the package. With this much privacy, space, and turnkey finishes, this house wont last long. Schedule your private showing before it’s gone!

282 Derby Road, 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

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