Middletown Condos for Sale

Welcome to Middletown, New York—a charming city nestled in the heart of Orange County that perfectly blends small-town warmth with modern convenience. With its rich history, vibrant community, and stunning natural surroundings, Middletown is a delightful place to call home. Known for its picturesque parks, unique local shops, and diverse dining options, this city offers a lifestyle that caters to both relaxation and adventure. Whether you're exploring the scenic trails of nearby state parks or enjoying a leisurely stroll through the historic downtown area, Middletown has something to offer everyone.

For those considering a move to this enchanting locale, we are excited to present a selection of exquisite condos for sale. These modern residences are designed with both comfort and style in mind, featuring open floor plans, contemporary finishes, and breathtaking views of the surrounding landscape. Each condo offers a low-maintenance lifestyle, allowing you to spend more time enjoying all that Middletown has to offer, from its vibrant arts scene to its seasonal festivals.

The condos for sale in Middletown are ideally situated, providing easy access to major highways, local amenities, and public transportation, making commuting to nearby cities a breeze. Whether you’re a first-time homebuyer, a young professional, or looking to downsize, these condos offer the perfect balance of convenience and luxury. Embrace the opportunity to live in a community that celebrates both its rich heritage and its promising future. Discover your dream condo in Middletown today, and let this charming city welcome you home!

Newest Middletown Condos for Sale

$390,000

3 Beds ⋅ 3 Baths ⋅ 1049937 MLS

The flooring on both floors of the house was replaced, and the central air conditioning, hot water boiler, dryer, dishwasher, stove, and Robam range hood were all replaced. Property Highlights Peaceful Cul-de-Sac Setting: Situated on Deer Court Drive, offering minimal drive-through traffic, enhanced privacy, and a safe, quiet street environment. Functional Living Space: Features a comfortable, well-proportioned layout designed for modern family living, entertaining, and work-from-home flexibility. Spacious Outdoor Area: Ample yard space ideal for outdoor gatherings, gardening, play areas, or relaxing in a serene natural setting. Turnkey Appeal: A welcoming entryway and curb appeal with well-maintained structural elements and grounds. Neighborhood & Community Advantages Prime Commuter Location: Convenient access to major regional transit corridors, including Route 17 (Future I-86), Interstate 84, and the Middletown-Town of Wallkill Metro-North station for hassle-free travel across Orange County and into New York City. Proximity to Everyday Conveniences: Minutes away from the Route 211 commercial corridor, Galleria at Crystal Run, major retail hubs, supermarkets, medical facilities (including Garnet Health Medical Center), and dining options. Hudson Valley Lifestyle: Close to local parks, hiking trails, golf courses, and farm-to-table markets, offering an ideal blend of suburban convenience and scenic countryside. Strong Community Atmosphere: Established, family-friendly residential neighborhood characterized by well-kept properties, mature trees, and high pride of ownership.

45 Deer Ct Drive, Middletown

$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

$484,900

3 Beds ⋅ 3 Baths ⋅ 1046984 MLS

Beautiful 3-bedroom, 2.5-bath condo inside and out! Formal dining room, eat-in kitchen with island, cozy fireplace, and huge windows with custom blinds and curtains. Convenient second-floor laundry room! Spacious lower-level playroom—perfect for movie nights and large enough for your own home theater setup. Walk in closets, a soaking tub, central air and a 2 car garage! Low HOA fees and truly a commuter’s dream. Enjoy the community pool, courts, playground, and so much more—you’ll be proud to call this Home!

22 Atwood Drive, 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

$305,000

2 Beds ⋅ 2 Baths ⋅ 1044653 MLS

Welcome to 18 Deer Court Dr, located in the desirable Deer Run community. This well-appointed second floor end unit offers approximately 1,291sqft, with 2 bedrooms, and 2 full bathrooms. This spacious condo combines comfort, style, and convenience in a wonderful Hudson Valley setting. Step inside to an open and inviting living and dining area featuring beautiful hardwood floors, creating a warm and seamless space for both everyday living and entertaining. The kitchen is thoughtfully designed with stainless steel appliances and a granite pass-through window, opening the space to the living and dining areas while making entertaining and conversation effortless. The bathrooms are enhanced with granite countertops, adding a touch of elegance and durability. Other updates include a new water heater (2025), new washer and dryer (2025), and a well-maintained HVAC system (2019), providing modern convenience and peace of mind. As an end unit, this condo offers an added sense of privacy, while the large, deep attached garage (53’) provides exceptional storage and parking space. Residents of Deer Run can enjoy an array of community amenities, including a clubhouse, seasonal swimming pool, tennis courts, and pickleball courts. Garbage pickup is also included. Conveniently located near Rt. 17 and I-84, this home offers easy access to shopping, dining, recreation, commuting routes, and all that Middletown and the surrounding Hudson Valley have to offer. Come see everything this Deer Run condo has to offer. Schedule your private showing today!

18 Deer Court 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

$289,900

2 Beds ⋅ 2 Baths ⋅ 1000877 MLS

Welcome to 141 Ruth Court! This move-in-ready two-bedroom, two-full-bath home has been freshly painted and features new carpeting throughout, offering a clean and inviting space that’s ready for you to make your own. With a comfortable layout, two bedrooms, and two full baths, this home is a wonderful opportunity for easy, turnkey living. Cathedral ceilings, 2 floors, open floor plan offering bright, open and airy spaces. The 2nd floor loft provides flexible space for a home office, play area or work out area. Simply unpack and settle in—this home is ready to welcome you! This home is also an excellent investment opportunity with no rental restrictions, low taxes and low HOA. Call to schedule a viewing today!

141 Ruth Court, Middletown

$579,000

4 Beds ⋅ 3 Baths ⋅ 1038040 MLS

Welcome to Wildflower at Wallkill, Orange County's premier 55+ community! Something Special! This 4 BR, 3 bath beauty is open and sun filled with vaulted ceilings and lovely detailed chair railings! 10 ft. ceilings and new wood floors throughout 1 st floor! Large LR opens to DR! Kitchen with island and undercounter lighting opens to vaulted family room with gas fireplace! Primary suite is on first floor and has 2 large walk in closets. There's another BR and full bath on first floor! 2nd floor has a loft and 2 BRs and a full bath! Water heater is 2 years old! There's a whole house surge protector!

34 Hawthorne Drive, Middletown

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