Middletown Homes for Sale

Welcome to Middletown, New York – a hidden gem nestled in the heart of Orange County! With its rich history, vibrant community, and picturesque landscapes, Middletown offers the perfect blend of small-town charm and modern convenience. Situated just 70 miles northwest of New York City, this city is an ideal haven for those seeking a peaceful lifestyle without sacrificing access to urban amenities.

Middletown boasts a diverse array of homes for sale, catering to various tastes and budgets. Whether you're searching for a cozy starter home, a spacious family residence, or a charming historic property, you’ll find it all here. The real estate market in Middletown is thriving, with options that include contemporary townhouses, elegant single-family homes, and even sprawling estates nestled in serene surroundings. Each neighborhood has its unique character, providing a welcoming atmosphere that encourages community engagement.

For outdoor enthusiasts, Middletown is surrounded by stunning natural beauty, featuring parks, hiking trails, and recreational opportunities. The nearby Hudson Valley offers breathtaking views and outdoor adventures, making it a perfect playground for nature lovers. Additionally, the city is home to a variety of shops, restaurants, and cultural attractions, ensuring that there’s always something to explore.

If you’re considering making Middletown your home, now is the perfect time to dive into the local real estate market. With a range of homes for sale, you can find the ideal property that suits your lifestyle and budget. Embrace the charm of Middletown and discover the perfect place to call home!

Newest Middletown Homes for Sale

$235,000

3 Beds ⋅ 2 Baths ⋅ MDFR2086498 MLS

Don’t miss this opportunity to own a home in the heart of Middletown! This livable fixer-upper is the perfect canvas for an investor, first-time buyer, or anyone looking to create their dream home while building valuable sweat equity. Enjoy a charming front porch, a fully fenced backyard, and LVP flooring already installed throughout much of the home. Whether you’re planning light cosmetic updates or a full renovation over time, this property offers incredible potential in a convenient location close to local shops, restaurants, and everyday amenities.

108 S Jefferson St, Middletown

$465,000

3 Beds ⋅ 2 Baths ⋅ 1024368 MLS

Discover the perfect blend of historic charm, modern comfort, and peaceful country living in this utterly delightful home, beautifully situated on 2.3 wooded acres. Rich in character, the residence showcases timeless architectural details while benefiting from a comprehensive renovation. Prior to renovation, the home was thoroughly gutted and fully foam insulated, with all-new plumbing and electrical systems, as well as energy-efficient mini-split units providing both heating and air conditioning. Enter through the welcoming mudroom into a spacious kitchen featuring stainless steel appliances, a charming dining alcove and a door out to the deck. The large, inviting living room is filled with tons of natural light. Upstairs, three comfortable bedrooms and a full bathroom complete the main residence. The property also features a separate cottage with a bathroom, offering excellent potential for guest accommodations, a home office, studio, or other flexible use. Located behind the cottage is an additional freestanding, one-room structure that may offer the possibility of being connected to the cottage to create a one-bedroom guest house or potential rental property, subject to all applicable municipal approvals. Surrounded by natural beauty, the property is located across the road from a picturesque pond creating a peaceful setting with abundant opportunities to enjoy the outdoors. Commuters will appreciate the home's proximity to the Train Station, providing service to Hoboken with easy PATH access into Manhattan. The property is also approximately one hour by car to Manhattan. Shopping, dining, and everyday conveniences are within easy reach, including the renowned Woodbury Common Premium Outlets.

168 Shawangunk Road, Middletown

$699,900

4 Beds ⋅ 4 Baths ⋅ DENC2107552 MLS

Elegant, Bright and Spacious and situated in the sought-after community of Dove Run, this grand estate home boasts of 4-bedrooms, 3.5 bathrooms with over 4,200 square feet of above ground living space and a stately full brick front facade. The kitchen is open and it has a lot of features cabinetry with quartz countertops. Of the kitchen is the breakfast room with plenty of sunshine. The family room is impressive with the soaring 2-story ceiling, oversized windows overlooking the private, tree-lined backyard. Between the living room and the family room is a two-sided fireplace. The main level also features a formal dining room, dining room, a private office, and additional living space. The upper level is equally impressive with the expansive owner’s suite featuring two walk-in closets, a sitting room, and a luxurious en-suite bath. This estate home has two separate staircases providing convenient access to the second floor. Relax yourself outside in the custom paver patio. On the lower level is the expansive full unfinished basement. It presents potentials for more space and entertainment areas. This home is conveniently located near stoppings and restaurants, major highways, award-winning schools, and much more. Upgrades on major items: Newer roof (2018), Newer furnace and A/C (2019), Newer water heater (2020). Schedule your tour today.

226 Bucktail Dr, Middletown

$850,000

4 Beds ⋅ 5 Baths ⋅ 1032582 MLS

A Rare Country Estate Rich in History, Character & Timeless Beauty. Nestled off the road and surrounded by approximately 17 private, wooded acres, this remarkable circa 1820 estate offers an extraordinary opportunity to own a piece of Hudson Valley history. Lovingly expanded over generations while preserving its original character, this one of a kind residence encompasses over 4,500 square feet of thoughtfully designed living space where historic craftsmanship and modern comfort exist in perfect harmony. From the moment you arrive, the setting is unforgettable. Mature trees, rolling lawns, handcrafted stone walls, beautifully landscaped gardens, and multiple patios create a peaceful retreat where nature becomes part of everyday life. Inside, authentic architectural details celebrate the home's rich heritage. Original woodwork, custom built-ins, exposed beams, hardwood floors, handcrafted moldings, and three fireplaces create warmth and character throughout. Every room offers a unique glimpse into the home's remarkable history while providing comfortable spaces for today's lifestyle. The stunning great room is truly the heart of the home, showcasing reclaimed hand-hewn beams salvaged from a local barn and an impressive floor to ceiling stone fireplace crafted from stone found right on the property. Nearby, an incredible sunroom with soaring wood ceilings, skylights, walls of glass, and beautiful terracotta style flooring invites you to relax while enjoying panoramic views of the surrounding landscape in every season. A thoughtfully designed private wing introduces a distinctive Southwestern-inspired aesthetic, creating an exceptional primary suite complete with a fireplace, spacious ensuite bath, private balcony, and adjoining first-floor living area. Whether used as a luxurious owner's retreat, guest quarters, or a comfortable multi-generational living space, this flexible wing offers endless possibilities while adding a unique architectural dimension to the home. Outside, the property continues to impress. A classic original barn featuring horse stalls, electric service, and an expansive loft provides incredible versatility for equestrian enthusiasts, hobby farmers, livestock, workshops, storage, or future creative pursuits. With acres of wooded privacy and open areas for horses, chickens, goats, gardening, or simply enjoying the outdoors, the possibilities are limited only by your imagination. As an added opportunity, an adjoining 16.7-acre parcel is also available for purchase, allowing the next owner to create an even more extraordinary private estate. Steeped in nearly two centuries of history yet thoughtfully adapted for modern living, this is more than a home it's a legacy property waiting for its next chapter.

232 Tally Ho Road, Middletown

$420,000

3 Beds ⋅ 3 Baths ⋅ 1033242 MLS

Welcome to Maple Fields! This well-maintained 3-bedroom, 2.5-bath townhouse with a versatile finished loft offers a functional layout designed for today's lifestyle. The main level features an open-concept living area, a dedicated dining space, and a bright kitchen with stainless steel appliances, a pantry, tile backsplash, and ample counter space. Sliding glass doors open to a private backyard patio, providing space for outdoor dining, grilling, or relaxing. Upstairs, the spacious primary suite includes a walk-in closet and an en-suite bathroom with double vanities and a tiled walk-in shower. Two additional bedrooms and the finished loft provide flexible space for a home office, media room, reading area, hobby space, or additional living area. Additional features include an attached one-car garage, generous storage, and a thoughtfully designed floor plan with bright, open living spaces throughout. Residents of Maple Fields enjoy access to community amenities including a clubhouse, swimming pool, fitness center, basketball courts, and playground. Conveniently located near Garnet Health Medical Center, major highways, shopping, restaurants, and public transportation, this home offers comfort and convenience in a desirable location. Some photographs have been virtually staged to illustrate the property's potential. Furniture and décor shown in virtually staged images are for illustrative purposes only.

4 Kless Court, Middletown

$235,000

3 Beds ⋅ 1 Baths ⋅ PADA2061082 MLS

Welcome home to this charming 3-bedroom Cape Cod nestled in the heart of Middletown! From the moment you arrive, you'll appreciate the care and updates that make this home truly special. The beautifully refreshed kitchen features tile flooring, updated cabinetry, modern countertops, a stylish tile backsplash, and newer appliances (2021), creating a warm and inviting space for everyday living and entertaining. The cozy living room offers durable laminate flooring and plenty of natural light, while the convenient first-floor primary bedroom provides easy one-floor living. A flexible laundry room can also serve as a home office, hobby room, or additional living space to fit your needs. Thoughtful updates provide peace of mind, including a new roof, efficient gas furnace and central air system (2020), and a gas water heater, water softener, and water filtration system (2017). Step outside to enjoy the fully fenced backyard—perfect for pets, gardening, gatherings, or simply relaxing. Two storage sheds offer plenty of room for tools, while the attached carport and driveway provide ample off-street parking. Conveniently located close to shopping, dining, schools, and major commuter routes, this delightful home offers comfort, character, and modern updates all in one package. Come see all it has to offer and imagine yourself at home!

115 Catalpa St, Middletown

$575,000

4 Beds ⋅ 3 Baths ⋅ DENC2105110 MLS

Welcome to this spacious and inviting Colonial offering a bright, open floor plan designed for both everyday living and entertaining. Step inside the impressive two-story foyer with soaring ceilings and beautiful hardwood flooring that extends throughout the entire main level. Just off the foyer, you'll find an exceptionally large front room that offers incredible flexibility. Whether used as a formal dining room, a sitting room, a family room, or a combination of spaces, this oversized room can easily adapt to your lifestyle. The heart of the home is the expansive kitchen and family room, where the open layout creates the perfect gathering place. The kitchen features white cabinetry, stainless steel appliances, a pantry, generous counter space, and a breakfast bar with seating for several. It overlooks the sunny breakfast area, surrounded by windows and offering sliding glass doors that lead to the backyard. The adjoining family room is warm and welcoming, highlighted by a cozy gas fireplace and seamless flow from the kitchen, making it ideal for entertaining or relaxing with family and friends. Upstairs, the spacious primary suite features elegant double-door entry, a vaulted ceiling, abundant natural light, generous closet space, and an en-suite bath with a soaking tub, separate shower, and dual vanities. The additional bedrooms are all comfortably sized, providing plenty of room for family, guests, or a home office. Outside, the level backyard offers a blank canvas for outdoor living, gardening, or play. Ideally situated within the sought-after Village of Bayberry North, this home is part of the highly regarded Appoquinimink School District and offers convenient access to parks, shopping, dining, and major commuting routes. (Square footage is estimated and should be independently verified.) Be sure to view the virtual tour and schedule your showing today!

615 Socrates St, Middletown

$339,000

2 Beds ⋅ 2 Baths ⋅ 1033088 MLS

Welcome to your new ranch home situated on a quiet dead end street yet still close to all major amenities. Arriving you will notice the peaceful surroundings, well manicured and level yard space, convenient garage and ample parking. Step inside your new home to find sun drenched living spaces, gleaming hardwood floors and the ease of one level living. The main level provides you with a cozy living room, two bedrooms, renovated full bath, updated kitchen and a formal dining room which provides flexibility for a potential den/office. Your eat-in kitchen provides ample storage space, gas cooktop, wall oven, Bosch dishwasher and easy access to the rear deck. The lower level of the home allows for additional expansion with it's own entrance, large family room, full bath with stall shower, laundry area and garage space. Enjoy relaxing out back on the mult-tiered deck space or find it the perfect place for entertaining and summer gatherings. All of this in a serene location yet minutes to shops, restaurants, schools, gyms, nature trails and much more.

11 5th Street, Middletown

$1,349,900

4 Beds ⋅ 4 Baths ⋅ MDFR2086162 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 3.78 beautiful acres, 7452 Heritage Oak Terr (Lot 4W) is a gorgeous build-ready homesite with perc approval and well installed. Advertised is the ACL4 plan which features over 4,400 finished sqft, 4 bedrooms and 3.5 baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, formal dining room, morning room, private office, a stately Owner's suite w/260 sqft walk-in closet, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

7453 Heritage Oak Ter, Middletown

$649,000

7 Beds ⋅ 7 Baths ⋅ VAFV2043696 MLS

Single family or multi-family with an approved, attached apartment - directly across from the famous Wayside Theater! This is a rare opportunity to own prime real estate in Middletown on a beautiful, large lot. Nestled in the heart of Middletown and just minutes from I-81, this exceptional 1920s home blends timeless character with modern updates. From the inviting front porch to the welcoming foyer with its stunning staircase, you'll immediately appreciate the home's classic charm. Beautiful wood floors, exposed brick, and multiple decorative fireplaces add warmth and character throughout. The updated kitchen features modern cabinetry, a center island, and ample space for gathering. Two main-level bedrooms each offer private en-suite baths, providing flexible living arrangements. Upstairs, the spacious primary suite includes a walk-in closet and attached bath, along with two additional bedrooms that share a hall bath. A unique highlight of this property is the attached second living unit located at the rear of the home. Complete with two bedrooms, two-and-a-half baths, a full kitchen, and living room, this space offers endless possibilities. It can serve as an in-law suite, guest quarters, or be seamlessly incorporated into the main residence to significantly expand the home's living space. The property also includes a detached two-car garage with additional storage, a storage shed, abundant parking, and plenty of outdoor space to enjoy. This one-of-a-kind property offers historic charm, flexible living options, and an unbeatable location.

7760 Main St, Middletown

$1,719,900

5 Beds ⋅ 8 Baths ⋅ MDFR2086198 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is a premier 12 lot luxury estate home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 7 beautiful acres, 3150 Bidle Rd (Lot 3E) is a gorgeous build-ready homesite with a 5BR septic approval and high yield 10gpm well already installed. Advertised is the ACL5 plan which features over 6,000 finished sqft, 5 bedrooms (including dual owner's suites), 4 full baths and 3 half baths. A spacious open concept layout is highlighted by 10' main level ceilings, a spacious kitchen with large center island and high end cabinetry, an additional prep kitchen, private office, parlor/enterainment room, formal dining room, morning room, upper level bonus room, primary suites on both main and upper levels, Hardie Plank siding and full stone water table are just a few standard options in this model. Photos are of a previously built home. Builder has several different plans and options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3150 Bidle Rd, Middletown

$1,249,900

4 Beds ⋅ 4 Baths ⋅ MDFR2086098 MLS

To-be-Built. Set against the stunning backdrop of scenic Middletown Valley, Heritage Oak Estates is Middletown’s premier 12 lot luxury home community presented by local builder Laine Street Homes. Heritage Oak Estates offers a rare opportunity to build the estate home you've always envisioned in one of Frederick County's most desirable locations. Surrounded by rolling countryside, breathtaking mountain views, and a strong sense of community, Middletown combines small-town charm with modern convenience. Nestled on 4.65 beautiful acres, 3130 Bidle Rd (Lot 1E) is a gorgeous build-ready homesite that offers a perfect combination of protected woodlands and rolling pastoral landscape. Advertised is the ACL3 plan which features over 3,000 finished sqft, 4 bedrooms, 3.5 baths including a main level owner's suite. Additional standard features include a spacious open concept kitchen with large center island and high end cabinetry, beautiful 2 story foyer, morning room, private office, luxurious Owner's suite, Hardie Plank siding and full stone water table. Photos are of a home that builder recently finished in Frederick County. Builder has several different plans and many options to choose from. Contact listing agent for available plans, site details, and to explore available homesite options for your future dream home at Heritage Oak Estates!

3130 Bidle Rd, Middletown

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