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$245,000
2 Beds ⋅ 2 Baths ⋅ 1029712 MLS
Welcome home to this beautifully maintained 2-bedroom, 1.5-bath condo offering the perfect blend of comfort and convenience! Featuring gorgeous wood flooring on the first level, new carpeting in the second level with spacious primary bedroom, walk-in closets in both bedrooms, updated bathrooms with beautiful vanities and tiles. Enjoy a functional layout in a location that's hard to beat—just minutes from shopping, dining, and everyday conveniences. Whether you're a first-time homebuyer, downsizing, or looking for a great investment opportunity, this move-in-ready condo is one you won't want to miss! Call today for more details or to schedule your private showing!

49 Jimal Drive, Middletown
$399,900
1028296 MLS
Location Location Locatiion !! Excellent Investment opportunity in one of the busiest Sought-after Locations in the Town Of Wallkill. This wonderful Building features a Professional office or Retail Space. Including a Spacious Foyer, 3 Large Open Spaces, Bathroom, Hardwood Floors, Natural Wood Trim, Lots of Windows. Beautiful Built in Cabinetry, and Storage area. Second Floor Offers a beautiful Apartment that consists of a Large Living Room, Bedroom with lots of closet area, Eat in Kitchen with plenty of cabinetry, and countertop space. very nice bathroom. Separate Electric. Huge walk out Basement is great for storage. Large parking Lot. Rocking Chair front porch. High Visibility on very Busy East Main Street. Perfect to work and live all under 1 Roof. or rent both spaces out for great income. Great for an Attorney, Doctor, Accountant, Hair Salon, Nail Salon, Acupuncture, ETC or small Business. Take advantage of this special opportunity. Next to Bay Wash Car Wash. Must see !!!

513 E Main Street, Middletown
$1,750,000
1021149 MLS
Rare Investment Opportunity: Fully Occupied 12-Unit Brick Building in Middletown, NY. Massive Income – Fully Updated – Separate Utilities – Low Inventory Market. Don’t miss this exceptionally rare turnkey investment in the high-demand Middletown market. Brick buildings of this scale and caliber rarely hit the market. This massive 12-unit mixed-use property is fully occupied, generating immediate, stable income from day one. Features 10 residential units and 2 prime commercial storefronts.Tenant-Paid Utilities: Tenants pay their own electric and gas. : Features a brand-new, building-wide structural back porch and extensive capital improvements throughout the exterior and common areas. A lot of Renovated Units: Most units are updated, making them highly attractive to tenants and supporting premium rental rates.100% Occupied:, reliable cash flow for the savvy investor. Location & Market Advantage Situated in a bustling, high-traffic area of Middletown, NY, this property benefits from excellent visibility for the commercial spaces and peak convenience for residential tenants. Big parking in the back. With inventory at an all-time low for multi-family and mixed-use assets in Orange County, this building represents a premier addition to the portfolio with strong appreciation potential. Schedule your private showing today before this rare gem is gone!

30-32 E Main Street, 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
$151,900
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
$395,000
1013153 MLS
Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office Space That is great for an accountant, attorney, Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hot water heaters. Large Parking Lot Second means of egress concrete staircase. Close to all the great restaurants, shops and pubs. Close to All Major highways train station and Bus terminal. Building is in good condition. Great investment opportunity. Must see !!

13 Benton Avenue, 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
$160,000
1 Beds ⋅ 1 Baths ⋅ 1010316 MLS
Renovated in 2021 is this first floor 1 bedroom condo in Buttonwood conveniently located close to Rte 17 and 84 for those of you commuting a distance to work. Just turn the key and move in, no work is needed. Kitchen has newer cabinets with crown molding and stainless LG appliances with a convection/air fry oven that can be controlled by your phone along with granite counters. Kitchen counter has pass through for more of an open floor plan, plus dining area. Bathroom was updated with new tub, vanity, flooring and tile as well. Large bedroom with dual closets and nice sized windows for lots of natural light. Beautiful new vinyl low maintenance flooring throughout. Navien energy efficient ON DEMAND heat and hot water system in place. Utility room to house the washer and dryer in kitchen.

226 Concord Lane, Middletown
$575,000
3 Beds ⋅ 3 Baths ⋅ 1003208 MLS
For Sale: Income-Producing Mixed-Use Building in Prime Downtown Middletown Take advantage of this exceptional opportunity to own a versatile, income-generating property in the heart of Downtown Middletown—an up-and-coming city with a pro-business government and strong growth potential. Property Overview: First Floor: Spacious 2,000 sq. ft. commercial space, currently used as a retail store, office, and storage area, plus a large multi-purpose room perfect for meetings, events, or classes Includes a full bathroom, retail front entrance, and private rear access Flexible layout offers potential for multiple businesses or tenants Second Floor: Two fully rented residential apartments: One large 2-bedroom unit One spacious 1-bedroom unit Each with its own kitchen, living room, and full bathroom Approx. 800 sq. ft. per unit Private Parking Lot: Rear parking accommodates up to 5 vehicles Unbeatable Downtown Location: Just steps from City Hall, the NYC bus terminal, the public library, restaurants, shops, and more—this location provides outstanding visibility and walkability for both commercial and residential tenants.

20 John Street, Middletown
$399,900
3 Beds ⋅ 3 Baths ⋅ 1001539 MLS
Privately set in a quiet and intimate four-unit HOA community, this bright and welcoming home offers comfort, space, and convenience throughout. An open foyer leads into the updated kitchen featuring Quartz/Quartzite countertops, crisp white cabinetry, and ample storage. Natural light pours into the spacious dining and living areas, highlighted by beautiful flooring and a large closet ideal for pantry use. A much needed half-bath completes the main level. Step outside onto the updated deck, perfect for summer barbecues and outdoor entertaining. Upstairs, you'll find three generously sized bedrooms and two full bathrooms. The primary suite comfortably accommodates a king-size bed and features a walk-in closet with built-in shelving, along with a private ensuite bath. Two additional bedrooms offer oversized closets and share a well-appointed full bath. A conveniently located second-floor washer and dryer add to the home’s functionality, while stylish flooring continues throughout the upper level. The spacious unfinished basement provides excellent storage potential. Additional highlights include a one-car garage and an expansive parking area that can accommodate 10+ vehicles. The monthly HOA fee of $450 includes insurance, exterior maintenance, snow removal, lawn care, and trash service. Located in the highly regarded Minisink Valley Central School District, this home combines privacy, practicality, and low-maintenance living. Schedule your showing today!

568 County Route 49 Unit #2C, Middletown
$395,000
998257 MLS
Beautiful Brick Mixed Use Building located in a very desirable area of Middletown. This wonderful building features 3 Units. First unit is Office Space That is great for an accountant, attorney, Real Estate office. Etc. Second Level offers a Spacious 1 Bedroom apartment 3 rd level offers another large 1 bedroom Apartment. Separate Electric and Hotwater heaters. Large Parking Lot Second means of egress concrete staircase. Close to all the great restaurants, shops and pubs. Close to All Major highways train station and Bus terminal. Building is in good condition. Great investment opportunity. Must see !!

13 Benton Avenue, Middletown
$799,000
995041 MLS
A rare opportunity to acquire and reimagine a 23.38-acre Catskills property with approximately 400 yards of private frontage along the East Branch of the Delaware River - an increasingly scarce combination of land, water access, and existing infrastructure. The river is not simply an amenity here, but a defining feature of the landscape, shaping both the setting and the experience. This is a property with the scale and flexibility to support a destination-driven hospitality concept, integrating recreation, food and beverage, event programming, and lodging in one cohesive setting. What makes this offering uniquely compelling is that the groundwork has already been laid. Over 25 years of ownership, the current operators have developed a fully functioning, multi-revenue property that can be continued, expanded, or repositioned over time. The existing operation includes a 9-hole public golf course (par 29, 1,600 yards, designed by Don Josberger), an 18-hole riverside mini-golf course with full night lighting, and a 275-yard floodlit driving range with 10 mat stations, a grass hitting area, and an adjacent practice green. A gambrel-style clubhouse with overhead doors allows for year-round use of the range and indoor/outdoor flexibility in all weather conditions. The property also features an established BBQ restaurant with two elevated decks overlooking the river and surrounding valley, supporting dine-in service, takeout, and catering. A newly built bar is in place, with a liquor license currently in the works. It is well equipped to host events, including weddings, tournaments, private gatherings, and community functions, with established infrastructure, ample parking, and easy circulation throughout the site. A newly built studio apartment provides accommodation for staff or guests. From here, the possibilities are unusually broad. The land and river frontage lend themselves naturally to cabins, glamping, or other small-scale lodging, while the existing restaurant could be elevated into a more design-forward, day-to-night destination. The river itself offers a natural extension of the guest experience, with opportunities for seating, gathering areas, or a more informal bar setting along the water's edge, as well as access to a prized stretch of the East Branch known for its fishing. The open acreage provides ample space for additional recreational or event-based programming - whether through lawn games, court sports, seasonal offerings, or flexible food and beverage concepts such as pop-ups or visiting operators. There is also potential to introduce technology-enhanced golf or simulator-based experiences, building on the existing range infrastructure. Few properties in the region offer this kind of layered, adaptable setting, with the ability to evolve in stages while maintaining an active business from day one. The location further strengthens the offering. Margaretville and the surrounding area are in a period of steady, thoughtful growth, with an emerging mix of food, beverage, and cultural destinations including Mornings, Rae's, Café Marguerite, Oda's Wine Garden, Long Year Gallery, Union Grove Distillery & Arkville Brewstillery, Folsom Point, and The Print House. Within easy reach of Belleayre Mountain and Plattekill, the area attracts a year-round audience drawn by skiing, hiking, fishing, and a growing local scene. For an experienced operator, hospitality group, or investor, this is an opportunity to step into an established platform and shape its next chapter -whether by refining the current business, expanding the guest experience, or repositioning the property over time. The combination of acreage, river frontage, existing revenue streams, and built infrastructure makes this a property that would be difficult to replicate today. A 3D Walkthrough Tour is available in the digital Lookbook or by request.

42565 Route 28, Middletown
$399,900
3 Beds ⋅ 3 Baths ⋅ 994032 MLS
Beautifully renovated 3-bedroom, 2.5-bathroom, 1-car garage, two-story townhouse located in the highly desirable Deer Run complex. This move-in-ready home features laminate flooring throughout, with tile flooring in the kitchen and bathrooms. The kitchen was tastefully updated in 2020, along with the heating and cooling system, which is electronically controlled and offers a high-efficiency SEER 16 rating. The living room boasts a fireplace with a high-end pellet stove insert, creating a warm and inviting atmosphere while helping to reduce heating costs. Deer Run offers great amenities, including a clubhouse available for special events, an inground pool, tennis courts, and more. Conveniently located just minutes from supermarkets, shops, and restaurants, with only a 5-minute drive to I-84 connecting to I-86. Close to Garnet Health Medical Center and the Galleria Mall. Approximately 10 minutes to LEGOLAND and under 20 minutes to Resorts World Catskills Casino Hotel. The HOA covers landscaping, snow removal, trash, and additional amenities for easy, low-maintenance living. This townhouse won’t last—schedule your showing today! Sale is subject to sellers securing suitable housing; they are actively looking.

83 Deer Ct Drive, Middletown
$450,000
989767 MLS
Positioned on a high-traffic corner, this commercial property offers excellent visibility and strong exposure, presenting an attractive opportunity for investors or owner-users alike. The property features ample parking, adding to its overall convenience and accessibility. A well-located property with strong potential and long-term upside.

2269 Mt Hope Road, Middletown
$1,800,000
947735 MLS
MIDDLETOWN/TOWN OF CRAWFORD...MANY POSSIBILITIES FOR DEVELOPMENT FOR THIS SUPER HIGH TRAFFIC WITH APPROXIMATELY 5000 CARS/DAY & HIGH VALUE LOCATION ON 5 CORNERS ON 2.14 ACRES WITH 200' ROAD FRONT ACCESS FROM EACH ROAD...One side is State Route 17K and on the other side State Route 302. Sale includes 2 separate properties selling only together. One w/commercial successfully active on one level, fully equipped 80 seat restaurant building for the last 34 years open 7 days a week w/access from both roads & currently rented. On the other parcel is a single family home currently rented. Both properties have separate septic & common well for water. Restaurant has propane for heating fuel. House has oil for heating fuel. Buyer can be a restaurant operator or a developer w/possible (gas station w/convenience store, liquor store, Dunkin' Donuts w/drive-thru, car sales...etc.) plans to maximize the value of this super busy location in Orange County next to a gas station/convenience store...Easy access location w/ short drive to Middletown, I-84, Montgomery, Newburgh & Pine Bush and connecting Orange, Ulster and Sullivan counties...

2850 State Route 17k, Middletown
$799,000
H6194864 MLS
Sale-Leaseback. Excellent investment opportunity on this quality office building centrally located on the E Main St/Crystal Run corridor. 100% Occupied. Seller is seeking a Sale/Leaseback and to continue his law practice in the building. The first floor is occupied by an established law firm. Second floor is now fully leased to two new tenants. Tenant 1 pays $1,100 per month plus utilities and cleaning. Tenant 2 pays $1,400 per month plus utilities and cleaning. Potential for purchaser to occupy. High profile location, well known, and highly traveled. Corner lot location with private parking lot located behind the building. Very good condition with zero deferred maintenance. Brand new A/C units, building just painted, parking lot re-done. Full basement currently utilized for file storage.

410 E Main Street, Middletown
$1,100,000
H6316891 MLS
Improved land. This exceptional 40-acre property is a versatile gem, ideal for various building ventures. The expansive pavilion is perfect for hosting weddings or events. This property offers clean convenient bathrooms, a well-maintained softball field, which is the only lighted field in the area a basketball court and a large shed for storage. Zoned residential--the perfect potential for development. Beautifully treelined, boasts a scenic walking trail for nature lovers. Plus, the extensive drainage system ensures the park stays pristine and functional year-round, regardless of weather conditions. This property is more than just a park; it's a haven for recreation with approved building plans for an 18k sqft building making it an ideal investment. Subdividable. See list of Permitted Uses and Special Permit Uses. Don’t miss this unique opportunity—schedule your tour today and discover the endless possibilities that this property has to offer!"

422 M And M Road, Middletown
$1,100,000
H6282597 MLS
Industrial Zone in the City of Middletown on 1.2 acres in total industrial area. 3600 clear span warehouse building with poured concrete block walls, concrete floors and newer roof. 45-4-17 is .55 acres and 45-4-18.1 is .65 acres. Level parking lot for around 60 vehicles. See brochure in docs Additional Information: FloorLoad:16,

18 Stanton Street, Middletown
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