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$345,000
3 Beds 1 Baths 1046566 MLS
Step into the warmth and charm of this beautifully maintained Colonial, where classic character meets comfortable modern living. Gleaming hardwood floors flow throughout much of the home, complementing the inviting architectural details found throughout. The spacious, sun-filled Living Room features an arched doorway leading to the Formal Dining Room—perfect for entertaining or enjoying memorable family gatherings. A versatile Den/Office offers a built-in bookcase and charming window seat, creating the ideal space for a home office, reading room, or quiet retreat. The updated Kitchen features granite countertops, tiled backsplash, laminate flooring, and opens seamlessly to a vaulted Family Room/Sunroom. Filled with natural light, this wonderful space provides easy access through sliders to a private deck overlooking the above-ground pool—an ideal setting for relaxing and entertaining. Additional highlights include thermal windows, central air conditioning on the first floor, a tankless water heater, walk-up attic, paver walkway, and a large storage shed. Move right in and enjoy all this special home has to offer! Ideally located close to shopping, restaurants, parks, wineries, hiking trails, and so much more.

8 Budd Avenue, 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

$115,000
2 Beds 1 Baths 1042491 MLS
Set among the trees on a private dirt road, this compact cottage offers a quiet place to get away without being far from everyday conveniences. The home features a ductless system for heating and cooling, a newer water heater, an updated bathroom, a new septic system, a new well, and a simple, low-maintenance layout. Outside, the wooded property includes a stone wall, natural fern-covered areas, and a brand new stick built 12' x 20' shed for storage, tools, or workshop space. The Shawangunk Kill is nearby, and the Otisville train station provides access toward New York City. Middletown’s shopping, dining, and services are approximately 15 minutes away. A practical option for a weekend retreat, creative space, fishing or hunting base, or buyer seeking a small home tucked in a wooded setting. Some work is currently being completed. The property will be sold as-is.

13 Birch Street, Middletown

$260,000
3 Beds 1 Baths 1040507 MLS
This multi-level Middletown home has much to offer. On the first floor there is a good-sized living room with hardwood flooring. There is an eat in kitchen with a large island. The full bathroom is also on the first floor. Additionally, there is another room on the first floor currently used as a bedroom (there is no closet), but can be an office, family room etc. The second-floor features 3 bedrooms. There is also a very convenient walk-up attic, great for storage or can be an additional room. Outside the driveway is shared with the neighbor on the right, but there is parking behind the home. Also, behind the home is a back porch and a park like area to enjoy the outdoors. Close to everything Middletown has to offer.

13 Ogden Street, Middletown

$2,400,000
1041303 MLS
Completely updated 8-apartment, 3-retail-unit mixed-use building located next to the bus terminal to NYC in downtown Middletown is for sale. The building underwent a full renovation at the end of 2022, including all-new electrical systems, plumbing, kitchens, apartments, and retail spaces. The entire building complies with current fire codes, featuring sprinklers and fire alarms. All units are fully rented and require minimal maintenance. The building is situated at the intersection of North St and Railroad St, in the heart of downtown Middletown, within walking distance of restaurants, supermarkets, shops, City Hall, and the soon-to-be-completed Heritage Trail extension. The property generates solid income with a 7% cap rate, and the location is outstanding.

104 North Street, 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

$549,999
4 Beds 4 Baths 1020924 MLS
Welcome to 19 Davidge Road, where luxury, comfort, and functionality come together in one exceptional home. Nestled in the highly sought-after Presidential Heights neighborhood, this impressive 4-bedroom, 4-bathroom residence offers the perfect blend of elegant living spaces and incredible amenities designed for today's lifestyle. From the moment you enter, you'll be captivated by the soaring vaulted ceilings and spacious open-concept design. The inviting living room features a cozy gas fireplace, creating the perfect atmosphere for relaxing evenings or entertaining guests. The chef-inspired kitchen is a true showpiece, complete with a commercial-grade stove, oversized commercial refrigerator, beautiful cabinetry, and abundant workspace that's ready to impress everyone from the home cook to the culinary enthusiast. Retreat to generously sized bedrooms and beautifully updated bathrooms, while hardwood flooring throughout much of the home adds warmth and timeless elegance. Car enthusiasts and hobbyists will appreciate the attached 2-car garage equipped with two professional vehicle lifts, allowing for indoor parking for up to four vehicles—a rare and highly desirable feature. "Basement, Garage, and 2 Yard photos has been digitally declutterred to show clear space."

19 Davidge Road, Middletown

$399,900
4 Beds 1 Baths 1031475 MLS
More space than meets the eye! This well-maintained 4-bedroom home features two first-floor bedrooms, a first-floor full bath, an enclosed sunroom, a full basement, a detached two-car garage, and a deep, level backyard. Notable improvements include a new roof, gutters, electrical panel, and exterior painting (2024); a new driveway (2023); whole-home updates in 2018 including new flooring throughout, all new double-pane windows, and interior painting throughout; and a replacement boiler (2016). The main level offers a bright living room, formal dining room, and kitchen with an adjacent breakfast area. The enclosed sunroom brings in abundant natural light and provides an inviting additional space to relax and unwind. Two additional finished bedrooms upstairs provide flexibility for sleeping, working from home, hobbies, or other needs. The full basement provides substantial storage and utility space, with a workshop area ideal for projects and hobbies. Outside, enjoy the deep, level backyard with plenty of room for outdoor activities, a private deck, and a detached two-car garage offering valuable parking and storage. Conveniently located near Downtown Middletown, shopping, dining, parks, and major routes. Come see in person the space, outdoor features, and versatility this well-maintained home has to offer. Some interior photos have been virtually staged for illustrative purposes only to demonstrate potential furniture placement. The property is being sold in its actual unfurnished/as-is condition.

39 California Avenue, Middletown

$469,000
5 Beds 3 Baths 1031210 MLS
Welcome home to this breathtaking Farmhouse-style retreat, perfectly set back from the main road amidst mature hydrangeas and Rose of Sharon. Step onto the sprawling, large rocking chair front porch—part of an expansive covered porch that wraps around three sides of the home—and experience true rustic charm before you even step inside. Upon entry, you’ll be in awe of the soaring vaulted ceilings, stunning wide plank wood floors running throughout, and a magnificent floor-to-ceiling stone fireplace. At the heart of the home is a gourmet country-style kitchen designed for entertaining. It features a spacious eat-in island, prep bar sink, Double Oven and a high-end gas cooktop complete with interchangeable wok burner and griddle attachments Dual sets of sliding glass doors seamlessly connect the kitchen to the rear deck for effortless outdoor dining. The main level features 2 light-filled bedrooms (one with private slider access to the deck) and a full bathroom. The upper level has additional bedrooms, a full bath, and a charming loft area overlooking the main living room. The basement has a cozy family room, a wet bar, 3rd full bath, and dedicated laundry room. Multi-level outdoor living including open and covered rear decks, plus a unique enclosed porch featuring a dog door leading directly to a secure 20 x 30 enclosed dog pen. A rare blend of rustic elegance, modern amenities, and peaceful seclusion—schedule your tour today!

495 Guymard Turnpike, Middletown

$399,900
5 Beds 3 Baths 1002381 MLS
Welcome to an opportunity that is becoming harder and harder to find. This multi-family property sits on a nearly half-acre lot in the City of Middletown and offers investors, contractors, and ambitious buyers the chance to create significant value. With 2,151 square feet, five bedrooms, three full bathrooms, and income-producing potential, this is the type of property that rewards vision and execution. Previously utilized as a three-unit property, the home will need to be used as a two-family residence moving forward per city guidelines. The opportunity here is simple: renovate, improve, and create a property capable of generating rental income for years to come. Whether your goal is to live in one unit while collecting rent from the other, add a cash-flowing asset to your portfolio, or pursue a value-add investment strategy, the foundation is already in place. Building plans are available to help complete the first-floor renovation, providing a head start for the next owner and helping bring the project to the finish line. Outside, you’ll find a large driveway with ample off-street parking, a rear deck, and a level backyard that adds both functionality and tenant appeal. While substantial repairs and updates are needed, opportunities like this are becoming increasingly scarce. The combination of size, lot dimensions, rental potential, and available building plans creates a compelling opportunity for the buyer willing to put in the work. Conveniently located near shopping, restaurants, schools, healthcare facilities, public transportation, and major commuter routes, the location further strengthens the property’s long-term appeal. Whether you’re looking to build equity, generate future rental income, expand your investment portfolio, or create a multi-generational living arrangement, this property offers the flexibility to support a variety of goals. Bring your contractor. Bring your vision. The plans are available, the potential is clear, and the opportunity to create something special is waiting.

37 Monhagen Avenue, Middletown

$610,000
3 Beds 3 Baths 999526 MLS
Charming Farmhouse Retreat on 2.9 Acres! Nestled on a quiet country road in the Town of Greenville and located within the desirable Minisink Valley Central School District. This beautiful farmhouse-style home offers the perfect blend of comfort, charm, and country living. Inviting home features 3 bedrooms and 2.5 baths with attractive Pergo wood flooring throughout the downstairs, while upstairs offers comfortable carpeting. Step up onto the welcoming covered wrap-around porch and enter through lovely double front doors into a foyer with an impressive cathedral ceiling. The farmhouse kitchen is both stylish and functional, featuring all stainless-steel appliances, granite countertops, and a large center island perfect for gathering with family and friends. The open floor plan leads to a dining area off the kitchen with a stunning bay window looking out onto the beautiful property and sliding glass doors that open to the wrap-around porch; creating a wonderful indoor-outdoor flow. Relax in the spacious living room featuring a cozy gas fireplace - the perfect spot to unwind. The 20x20 bonus room, also with pergo flooring, located above the attached 18x20 garage hosts its own separate entrance and bright airy windows with plenty of natural light; perfect for a potential mother daughter suite. The home includes plenty of storage with a detached one car garage, 18x20 attached garage, easily accessible full attic and 5ft walkable crawl space that is the length of the house and accessible from the kitchen. Peaceful surroundings, charming details, and plenty of room to enjoy country living make this home one you won't want to miss. A must-see property!

5 Decker Drive, Middletown

$199,000
1 Beds 1 Baths 927923 MLS
Welcome to 51 S Shore Drive, a charming and thoughtfully updated bungalow retreat nestled on a private, wooded 9,374 sq ft lot with sparkling lake views in scenic Middletown, NY. This beautifully curated 1-bedroom, 1-bath lakefront getaway offers 360 square feet of smart, stylish living space perfect for a weekend escape, vacation rental, or year-round peaceful living. Step inside to a crisp, modern interior featuring a cozy stone-accented fireplace, sleek black cabinetry, upgraded appliances, and luxury vinyl plank flooring. The open-concept living space is bright and inviting with fresh finishes, vaulted ceilings, and picture windows that frame the surrounding forested hillside. Step outside and you'll be swept away by the home's crown jewel, a brand-new oversized deck with ample space for grilling, lounging, and soaking up nature’s beauty. Whether you're sipping your morning coffee or enjoying sunset dinners, this deck offers a front-row seat to the tranquil lake just beyond the trees. The lot itself is partly wooded and gently sloped, offering both privacy and unobstructed water views. It's the perfect backdrop for nature lovers, creatives, or anyone seeking a peaceful recharge in the heart of the Hudson Valley. Located less than 90 minutes from NYC, and close to local farms, wineries, hiking trails, and charming small towns, this home is ideal for weekenders, investors, or full-time residents who crave a simpler, quieter lifestyle with modern comforts. Escape the ordinary, 51 S Shore Drive is lake living reimagined.

51 S Shore Drive, Middletown

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