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

$1,680,000

5 Beds ⋅ 9 Baths ⋅ 1027724 MLS

Welcome to 3 Bristol Drive, a rare brick colonial estate set on 1.4 private acres, offering nearly 8,000 Sqft of living space plus a spectacular 3,200-square-foot indoor pool pavilion designed for year-round enjoyment. Built in 2002, this 6-bedroom suits, 8.55-bathroom residence features expansive, light-filled interiors and estate-scale proportions ideal for both entertaining and everyday living. Each bedroom includes a private en-suite bathroom, providing comfort and privacy throughout the home. The layout flows seamlessly between formal entertaining spaces and casual living areas, accommodating gatherings of any size. The indoor pool pavilion is the centerpiece of the property, featuring a heated swimming pool, surrounding lounge areas, and a 10-person jacuzzi—creating a private, spa-like retreat rarely found in residential homes. This resort-style amenity allows for year-round relaxation and entertaining regardless of season. Outside, a circular roundabout driveway offers impressive curb appeal and convenience, while a private courtyard and manicured grounds enhance the estate-like setting. The classic brick facade and colonial architecture deliver timeless elegance with the durability of quality construction. Offering exceptional privacy while remaining conveniently located near major roadways, shopping, and dining, 3 Bristol Drive presents a unique opportunity to own a luxury estate with true resort amenities in the Hudson Valley. Schedule your private showing and experience this one-of-a-kind property

3 Bristol Drive, Middletown

$899,000

5 Beds ⋅ 5 Baths ⋅ 1026134 MLS

Enter the gates of this remarkable 36.8-acre estate to discover a distinguished 5-bedroom, 5-bathroom residence offering 4,200 square feet of living space. The property includes a substantial two-story post-and-beam barn with horse stalls, multiple wells, and an additional hay barn—ideal for equestrian or agricultural use. A serene natural pond and a mix of rolling pastures and wooded areas complete the setting. The original 1821 Colonial estate serves as the main house, blending historic character with thoughtfully updated features throughout. The expansive grounds provide abundant opportunities for recreation, including horseback riding, farming, snowmobiling, four-wheeling, fishing, and more. With numerous updates and an array of versatile structures, this exceptional property offers a rare combination of privacy, history, and functionality. The land is also subdivisible, providing potential for future development. Amenities: Storage, multiple barns, natural pond, extensive acreage.

255 Howells Road, Middletown

$379,999

2 Beds ⋅ 2 Baths ⋅ 1021532 MLS

Welcome to 8 Forest Ave, Middletown, NY 10940—a charming corner-lot home offering comfort, flexibility, and plenty of outdoor space. This well-maintained property features 2 spacious bedrooms plus a bright sunroom that can easily be converted into a third bedroom, home office, or guest room. The home also offers 2 full bathrooms, a generously sized kitchen, and a separate dining room, providing a functional layout for everyday living and entertaining. The full unfinished walkout basement presents endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the large deck overlooking a spacious backyard, perfect for gatherings, outdoor dining, or relaxing with family and friends. The corner lot also provides ample space for gardening, landscaping, or other outdoor activities. Conveniently located near shopping centers, schools, restaurants, parks, and major commuter routes, this home combines comfort, convenience, and potential in one desirable location. Don’t miss the opportunity to make this versatile property your next home!

8 Forest Avenue Unit #6, Middletown

$325,000

2 Beds ⋅ 1 Baths ⋅ 1020584 MLS

AFFORDABLE COLONIAL HOME with low taxes, two bedrooms, one bathroom, and flexible extra space. This 1,080 sq. ft. home features vinyl siding, municipal services, and natural gas for heat, hot water, and cooking. Enjoy private off-street parking for up to three cars, with curb-cut access from two streets. The home offers classic charm and character, a covered front porch, concrete walkways, and outdoor space suitable for a small garden, play area, or additional parking. The first floor includes the main living areas: living room, kitchen, and dining area. Upstairs are two bedrooms and a full bathroom, with a walk-up attic providing extra storage. The walk-out basement offers space for a family room, laundry area with washer and dryer, plus windows and a door leading to a concrete patio overlooking the green yard and private parking. The first and second floors currently have carpet, with original hardwood floors underneath. Conveniently located near services and amenities, within walking distance of the community college and just a five-minute drive to the I-84 intersection. With ownership costs comparable to rent, this charming home is a great opportunity to buy instead of renting a home.

10 Forest Avenue, 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

$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

$769,000

5 Beds ⋅ 5 Baths ⋅ 1011283 MLS

Step into 5-bedroom Colonial-style home, where classic charm meets upscale upgrades. From the moment you enter, you’re welcomed by exquisite craftsmanship, including detailed crown molding and rich hardwood floors that flow seamlessly throughout the main living spaces. This spacious residence features three elegant fireplaces, creating warm and inviting focal points across multiple living areas perfect for both entertaining and everyday comfort. The thoughtfully designed layout offers generous room sizes, abundant natural light, and a seamless blend of traditional character and modern functionality. The finished basement provides additional versatile living space, ideal for a home theater, gym, recreation area, or guest suite tailored to suit your lifestyle needs. Every detail of this home reflects quality and care, making it truly move-in ready. This property offers the perfect combination of sophistication, comfort, and convenience.Your Presidential Address Awaits: Comfort, Class, and Community.

3 Truman Court, Middletown

$560,000

3 Beds ⋅ 3 Baths ⋅ 1011153 MLS

Welcome to this beautifully maintained contemporary bi-level home set on 2.2 private acres in the scenic countryside of Orange County. Built in 2015, this exceptional residence combines modern comfort with peaceful surroundings, offering the perfect balance of privacy and convenience. The impressive entryway welcomes you with soaring cathedral ceilings, abundant natural light, and an open, airy layout designed for today's lifestyle. provide flexibility for guests, or a home office. also has two-car garage. parcel of land in the heart of the Hudson Valley.

2078 Route 6, Middletown

$499,000

4 Beds ⋅ 3 Baths ⋅ 1008642 MLS

GORGEOUS turn-key home located in the outskirts of Middletown with Minisink schools. Do NOT let the outside fool you as this home is much larger than expected... Step inside this Raised Ranch that is in mint condition with the upgrades it offers. Open floor layout from Living room to dining area & kitchen. New hardwood floors in upper level, vinyl floors in lower level and recessed lighting throughout. Modern eat-in kitchen with new cabinets, granite countertops, backsplash & gorgeous fresh out the box stainless steel appliances! 3 bedrooms are located on the main level, one which is a Suite with its own private bath and gorgeous tiled shower. A 2nd full tiled bathroom with a tub completes the upper floor. A finished lower level offers the 4th additional bedroom, along with a family room and office for those that work remotely. The 3rd full tiled bath with all new accessories and laundry area with NEW washer & dryer completes the lower level. Grill and enjoy morning coffee right out outside your deck and grill on your lower level patio! For those that love the outdoors, enjoy this oversized fenced-in backyard ideal for you to enjoy & entertain in. Among some of the upgrades this home offers are the new roof, siding, plumbing with new ductless heating and cooling systems, modern lighting, new hardwood & vinyl floors and more! Close proximity to Colleges, Touro Medical, Garnet Health, and shopping centers. Minutes to Public transportation and major highways for those that commute. Look no further & make this lovely home yours today!

37 California Drive, Middletown

$685,000

3 Beds ⋅ 3 Baths ⋅ 1006639 MLS

Update - priced to sell! Imagine waking up surrounded by three private acres while still being just minutes from shopping and major commuter routes. This newly built colonial offers the peace of country living without sacrificing convenience. The open-concept kitchen, oversized island, fireplace, spacious primary suite and unfinished basement provide room to grow while giving buyers the opportunity to personalize the space. Move right into this home upgraded with premium finishings in the desirable Minisink Valley School District. Set along a quiet road surrounded by sweeping views of green rolling hills, the home offers a rare sense of space, privacy, and peace. Enjoy miles of scenic vistas from the deck, the sprawling lawn, and a serene atmosphere, all just minutes from Middletown's shopping, restaurants, parks, schools, and major commuter routes. This home features 3 bedrooms, 2.5 baths, generous open floor plan, living room fireplace, central air, an attached 2-car garage, and a full unfinished basement ready for future expansion. Inside, thoughtful upgrades selected by the sellers elevate the home well beyond typical new-build standards. These upgrades were paid for separately from the initial home purchase price and include red oak hardwood flooring throughout, upgraded staircase, custom glass kitchen cabinetry, enhanced kitchen island, designer chandelier, Calacatta Montage finishes, upgraded front door and windows, additional recessed and accent lighting, and beautifully enhanced primary and guest bathrooms, and more. The spacious kitchen is designed for both everyday living and entertaining, offering granite countertops, a tile backsplash, and generous island seating. The primary suite provides a private retreat with a walk-in closet and a luxurious bath featuring dual vanities, a soaking tub, and a glass-enclosed tiled shower. Combining the freshness of new construction with premium custom finishes and an exceptional setting, this home offers the perfect blend of comfort, elegance, and countryside charm.

168 Pine Grove Road, Middletown

$435,000

3 Beds ⋅ 4 Baths ⋅ 1004718 MLS

Welcome to Swan Village Estates conveniently located just minutes from Highways, stores and shopping. If space is what you need, this three-level , corner lot townhome offers that and more inside and out! The main level features a bright living room with plenty of natural window light followed by a dining area and a spacious eat-in kitchen with stainless steel appliances with plenty of cabinet and counter space. Slider glass doors off dining area lead to a deck where you can enjoy morning coffee from a canopy that’s overlooking an oversized backyard with a playground in place. Plenty of yard space for summer enjoyment and entertaining as this is a corner lot! A half guest bathroom completes the main level. The second level features the Primary Suite with a private bath with a tub and walk-in closet! Two additional well-sized bedrooms and a full hallway bathroom completes the second floor that is all carpeted. The finished walk-out basement provides additional space suitable for an office space for those that work remote, an exercise room or play area for the little ones. If storage is needed, it’s found in this level as well as the outdoor shed ideal for o outdoor furniture or tools. The lower level also includes the 3rd full bath for your convenience and a laundry area with a washer and dryer to avoid trips to the laundromat. New ductless units for your heating and AC needs! Conveniently located within short distance to Garnet Health, Touro Medical, shopping, major highways, and a variety of dining options. Call and book your tour today as this one will not last!

60 Peach Place, Middletown

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