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$1,885,000
2 Beds 2 Baths 1048430 MLS
Exceptional 33.6-acre equestrian property in the Town of Wallkill, thoughtfully developed for serious equestrians. Classified by Orange County as a Horse Farm and located within an NYS Agricultural District, it features a substantial barn complex, indoor and outdoor riding arenas, numerous paddocks and turnout areas, supporting structures, and a two-bedroom apartment for on-site living. The grounds include approximately 15 medium-size grass paddocks, 8 smaller sand paddocks/turnouts near the barn for winter and inclement-weather use, a dedicated medical turnout, and a fenced field of approximately 6.5 acres with an interior fenced area surrounding a 30 x 64 loafing shed built in 2013. The shed includes a 12 x 16 stall, feed room, storage room, and 30 x 48 matted area with wall-mounted hay feeders, providing flexibility for turnout, rotation, rehabilitation, and herd management. Many exposed wood edges are protected by metal edging to help prevent chewing and reduce wear. Each paddock has access to one or more Nelson automatic waterers. Numerous frost-resistant outdoor faucets, plus one in the barn, provide backup access to fresh water, while electrical outlets throughout the grounds support water heaters, tools, and daily needs. Built in 2007, the main barn is designed for efficient horse care. A 16-foot-wide center aisle serves 8 approximately 12 x 12 stalls, each with rubber mats and Nelson automatic waterers. Two wash/grooming stalls feature hot and cold water and heat lamps. A climate-controlled tack room offers protected storage for saddles, bridles, and equipment. A dedicated feed room includes a storage closet. A separate utility room has a washer and dryer, with numerous closets throughout the barn for organization. A camera system provides coverage in each stall and throughout the barn. Above, a massive hayloft includes storage closets and individual hay chutes serving the stalls below. It accommodates approximately 1,400–1,600 oversized 50–55 lb. bales of hay, plus substantial bedding-pellet storage on a reinforced plywood section suitable for pallet-jack movement. Covered ventilation hatches provide airflow and protection from the elements. A heated and air-conditioned barn lounge offers year-round comfort for riders, trainers, staff, and guests and is appointed with quality cabinetry, granite countertops, sink, microwave, under-counter refrigerator, tile flooring, and recessed lighting. A heated and air-conditioned half bath is appointed with quality finishes. The approximately 1,280 sq. ft. two-bedroom apartment features an open living layout, granite kitchen with generous cabinetry and peninsula offering additional workspace and seating potential, full bath, and utility/laundry area, well suited for an owner, trainer, barn manager, staff member, or guests. The 84 x 214 indoor riding arena is equipped with TravelRight dust-free footing for comfortable year-round riding and training and is complemented by a 130 x 235 outdoor arena. Permanent four-board and no-climb top-board fencing, gates, established lanes, and an organized barn-and-paddock layout enhance day-to-day horse management. An automatic entrance gate provides controlled access. A backup generator supports the property during outages, while a hand pump on the well offers another means of obtaining water for animals during a prolonged outage. Conveniently located a short drive from Route 17/I-86 Exit 119, the property combines easy regional access with the privacy and space of a country equestrian setting. The acreage, extensive infrastructure, riding facilities, and on-site accommodations create a rare opportunity to acquire an established horse property in the Middletown/Town of Wallkill area. Available as 120 Shaw Road on its own or as a package with 174 Shaw Road, adding approximately 3.8 acres and an additional building site for expansion, future development, residential use, or enhanced equestrian operations.

120 Shaw Road, Middletown

$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

$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

$1,900,000
1035967 MLS
**Exceptional Mixed-Use Investment & Redevelopment Asset in Downtown Middletown!** Tailored specifically for vision-driven developers, value-add real estate investors, and expanding commercial operators, this versatile multi-level property offers the rare combination of immediate cash flow and substantial long-term growth potential. The project pairs an established ground-floor restaurant tenant—delivering steady, in-place revenue from Day 1—with expansive multi-floor operational space including a main-level industrial production zone, a full basement, and dedicated lift access ideal for food manufacturing, warehousing, or light distribution. For residential developers, the clear value proposition lies overhead: convert the underutilized upper stories into high-demand residential units or urban lofts within a hungry rental market. Adjacent to a high-capacity municipal lot for effortless parking and loading, the building sits prime in Middletown’s Downtown Mixed-Use (DMU) Zone. Investors benefit from a highly business-supportive municipality featuring streamlined approval channels, local Industrial Development Agency (IDA) tax incentives, and active Business Improvement District (BID) support. A truly dynamic asset offering built-in income, operational scale, and premier development upside in Orange County. Qualified buyers are encouraged to reach out to arrange a private viewing and review complete property details. Note: This was the former home of Equilibrium Brewery they outgrew this location and moved to 2 South St, Middletown, NY.

28 Henry Street Unit #22, Middletown

$424,999
4 Beds 2 Baths 1035711 MLS
Calling all investors and future house hackers! This versatile duplex is the perfect opportunity to grow your rental portfolio or offset your mortgage by living in one unit while renting the other. Each apartment offers 2 bedrooms and 1 full bathroom, featuring spacious living areas, an open-concept layout, and generously sized bedrooms. One of the units also includes a dedicated office space, making it ideal for remote work or added flexibility. The home also features a partially finished basement, providing additional storage or usable space. Conveniently located in the heart of town, you’ll enjoy easy access to shopping, restaurants, schools, and major commuter routes. Whether you’re searching for your next income-producing property or a smart owner-occupied investment, this duplex checks all the boxes. Don’t miss your chance to add this fantastic property to your portfolio!

11 Sunnyside Avenue, Middletown

$450,000
1034632 MLS
This property is a prime commercial opportunity meticulously prepared for seamless ownership transition. It comes equipped with a dealership license, ensuring all regulatory requirements are met and eliminating the need for additional licensing hurdles. Additionally, the lease is an easy transfer to the new owner. The facility boasts a four-car garage, providing versatile space for storage and expansion. One of the property’s most compelling features is its extensive parking capacity, with designated areas that allow dozens of vehicles to park and maneuver simultaneously. This makes it an ideal choice for businesses with high customer or employee traffic. The spacious and well-organized layout further enhances its appeal, providing flexibility for various operational needs. Whether you’re looking to continue an existing business or launch a new venture, this property offers the infrastructure and convenience to support your goals. To fully experience its potential, I invite you to schedule a private tour.

718 Route 211 W Unit #716, 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

$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

$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

$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

$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

$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

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