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

$880,000

4 Beds ⋅ 5 Baths ⋅ DENC2108278 MLS

A GRACIOUS WELCOME: This stately Anderson Homes Evanston Grand is one of the largest models in Back Creek. It offers 6,800 sq. ft. of finished living space on a private 0.80-acre lot. From the moment you step inside the grand foyer, elegant finishes and an effortless flow set the tone for both everyday living and grand entertaining. ELEGANT ENTERTAINING SPACES: A formal living room offers a refined setting for entertaining guests, while the adjacent formal dining room provides ample space for hosting memorable holiday gatherings and special occasions. THE GOURMET KITCHEN: The heart of the home is a chef-inspired, eat-in kitchen featuring a spacious granite center island, gleaming granite counters, a granite butler's pantry, and premium GE appliances. The attached morning room provides the perfect spot for morning coffee or casual gatherings. A WARM GATHERING SPACE: The main level is also anchored by a family room complete with built-in bookcases and a cozy fireplace, creating the perfect spot to unwind after a long day. A dedicated home office offers a quiet space to work from home, and a sunroom framed by soaring arched windows fills the main level with natural light. THE OWNER'S RETREAT: On the second level, the primary suite is a true sanctuary and offers the perfect way to end the day. Double doors open to reveal a tray ceiling, a large separate sitting room, a spa-inspired bath, and two generous walk-in closets. COMFORT FOR ALL: With 4 bedrooms, 4 full baths, and 1 half bath, accessed by two separate staircases, there's ample room to enjoy comfort and privacy. A private guest suite with its own full bath offers a welcoming retreat for visitors, while two additional bedrooms share a convenient Jack-and-Jill bath. ENDLESS POSSIBILITIES: The fully finished walk-out lower level is an entertainer's dream, complete with a custom surround-sound movie theater and theater-style recliner chairs. Sunday football will never be the same! There is also a dedicated exercise room, a kitchenette, and a full bath, offering incredible flexibility for guests or dual-living arrangements. Storage space is plentiful as well. OUTDOOR LIVING: Outdoors, an 11-zone irrigation system and a deluxe landscape lighting package keep the grounds looking pristine day and night with minimal upkeep. A side-entry 3-car garage adds everyday convenience, and a large deck overlooks the spacious backyard. COMMUNITY & LIFESTYLE: The home is located in the sought-after Back Creek Golf Club community. The clubhouse restaurant, 7 Tap Tavern, is located right in the neighborhood. Enjoy easy access to the championship golf course, two playgrounds, and open green spaces, all just minutes from local shops, the Christiana Mall, excellent restaurants, and commuter routes to the beach. 103 BROOKS DRIVE ISN'T JUST A HOME. IT'S A LIFESTYLE!

103 Brooks Dr, Middletown

$399,900

3 Beds ⋅ 2 Baths ⋅ PADA2062554 MLS

If you're looking for an updated home with just under 1 acre of land with plenty of privacy.... look no further! Come see the updated ranch home, one floor living, new kitchen, new bathrooms new flooring and so much more. Home has 3 bedrooms, 2 full bathrooms, oversized two car garage and almost 1 acre of land. Still plenty of time to enjoy your summer nights on the deck. Home is located in quiet, wooded area but still has great access to rt 283 and pa turnpike. Come see for yourself!!!

1384 Roundtop Rd, Middletown

$419,900

4 Beds ⋅ 1 Baths ⋅ 1031475 MLS

Welcome to this charming and well-maintained 4-bedroom home offering a practical layout and timeless character. The main level features a bright living room, formal dining room, eat-in kitchen, two bedrooms, and a full bath, while the upper level provides two additional bedrooms with flexible living space. Recent improvements include a new roof (2024), vinyl double-pane windows installed in 2018, and a resurfaced driveway completed in 2023. A bright enclosed front porch adds additional living space and a welcoming place to relax. Outside, enjoy a generous backyard, a detached two-car garage, and ample off-street parking. Conveniently located near schools, shopping, restaurants, parks, and major highways, this home offers comfort, convenience, and everyday functionality in an established neighborhood. Some photos have been enhanced for presentation purposes. Some interior photos have been virtually staged for illustrative purposes only to demonstrate potential furniture placement. The property is being sold in its current, unfurnished, as-is condition.

39 California Avenue, Middletown

$725,000

5 Beds ⋅ 5 Baths ⋅ 1032557 MLS

Welcome to this one-of-a-kind custom home tucked away at the end of a quiet cul-de-sac in the highly sought-after Pine Bush School District. Offering over 4,200 square feet of living space, this home combines quality craftsmanship, privacy, and features you simply won’t find anywhere else. Step inside to soaring cathedral ceilings, beautiful hardwood floors throughout, and a formal dining room accented with elegant columns. The chef’s kitchen is truly the heart of the home, featuring custom solid wood cabinetry, a Carrara marble double-tier island, stone backsplash, farmhouse sink, and premium stainless steel appliances, including a 72 x 60 -inch Sub-Zero refrigerator, Thermador wall oven, and DCS cooktop. One of the home’s most unique features is its collection of approximately 350-year-old reclaimed wood interior doors, adding warmth and character throughout. Recent improvements include a newer roof, new black-top driveway, new windows, three heating systems, three central air systems, and a whole-house automatic generator. The second floor offers an incredible primary suite with two private en suite bathrooms, along with four additional bedrooms and three full bathrooms, providing plenty of space for family and guests. The finished walk-out lower level offers endless possibilities with a huge family room, home theater, two additional bedrooms, full bathroom, office, art studio, sauna, and access to the outdoor hot tub area. Built for a former collector of fine art and rare minerals, the lower level also features multiple heavy-duty vault doors, a secure fire-safe storage area, and an extensive security system, making this home as secure as it is impressive. Outside, you’ll love the heated stone walkway, brand-new covered screened porch overlooking beautifully landscaped grounds filled with flowering gardens and an amazing variety of fruit trees and berry bushes, including peach, apple, pear, plum, cherry, raspberry, blackberry, and blueberry. French drainage system, an oversized garage complete with built-in cabinets and workshop space, an attached three-car carport, and a storage shed. Set at the end of a dead-end cul-de-sac, this property offers exceptional privacy while still being close to everything the Hudson Valley has to offer. This is truly a rare opportunity to own a home that blends luxury, functionality, and unmatched character.

14 Longview Lane, Middletown

$600,000

4 Beds ⋅ 3 Baths ⋅ DENC2108242 MLS

Rarely Available Fairview Farm! Cul de sac lot with the greatest neighbors ever! Realtor/Listing Agent Owned. New Roof 2018; New Gas Furnace 2018; New AC 2022; Pool Liner 2022; Pool Converted to Salt Water 2024; Water Heater 2023. Looking for a great neighborhood, great schools? You found it!

6 Bull Run Ct, Middletown

$540,000

4 Beds ⋅ 3 Baths ⋅ VAFV2043622 MLS

Experience the best of Shenandoah Valley living in this beautifully located home, where breathtaking sunset mountain views create the perfect backdrop to everyday life. Nestled in a quiet, dog-friendly community, you'll enjoy peaceful surroundings without sacrificing convenience. Ideally situated just minutes from I-81 and Route 66, this home offers an easy commute while keeping you close to everything you need. Spend weekends exploring local wineries, hiking trails, parks, and the natural beauty of the Shenandoah Valley, or enjoy the nearby restaurants, shopping, and everyday conveniences just moments away. Built in 2023, this residence boasts a spacious open. layout, perfect for modern living. The kitchen features quartz countertops, a central island, and stainless steel appliances, including a gas stove. With four generous bedrooms, including a main level bedroom, and additional loft this home offers ample space for everyone. The primary suite is a true retreat, complete with a walk-in closet and a luxurious bath. Enjoy the convenience of upper-floor laundry and thoughtful touches like recessed lighting throughout. Outside, the property is equally appealing. The lot backs onto an open common area, providing a sense of privacy, all highlighted by a stunning mountain view. Enjoy leisurely strolls along the nearby jog/walk path or relax in the beautifully landscaped rear yard. The attached two-car garage and concrete driveway offer plenty of parking and storage options. Additional features include school bus pick up within the neighborhood, a playground and sidewalks that enhance the neighborhood's charm. With common area maintenance and management included in the association fee, you can enjoy a low-maintenance lifestyle. This home is not just a place to live; it’s a place to thrive.

102 Curtain Fall Dr, 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, 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

$685,000

5 Beds ⋅ 4 Baths ⋅ DENC2104064 MLS

Welcome to this stunning 5-bedroom, 3.5-bathroom home located in the highly desirable Cantwell Ridge neighborhood. Situated on a spacious corner lot, this home offers the perfect blend of comfort, functionality, and space for everyday living and entertaining. The main level features a private primary suite conveniently located just off the living room, complete with a spacious en-suite bathroom featuring dual vanities. As you enter the home, you're welcomed by a formal dining room, ideal for hosting family gatherings and special occasions. The adjacent kitchen overlooks the impressive living room with soaring ceilings, creating an open and inviting atmosphere. Just beyond the living area, you'll find a bright and spacious sunroom that overlooks the fully fenced backyard. Step outside to enjoy your own private retreat featuring an in-ground pool, a patio perfect for entertaining, and a storage shed for added convenience. The partially finished basement expands the home's living space with a large bedroom, a full bathroom, and an egress window, making it an ideal guest suite, recreation area, or additional living quarters. Upstairs, you'll find three generously sized bedrooms, each offering ample closet space, along with a full hall bathroom to accommodate family and guests. With its desirable location, thoughtful layout, and exceptional indoor and outdoor living spaces, this home is one you won't want to miss. Schedule your private tour today!

200 Drawyers Dr, Middletown

$449,900

3 Beds ⋅ 1 Baths ⋅ 1028580 MLS

STOP THE SEARCH!!!! THIS ONE IS A SHOWSTOPPER!!! Welcome home to 30 Murray Road in the Town of Walkill, an immaculately maintained, completely turn key ranch! Spotless from top to bottom and lovingly cared for, this exceptional home offers the perfect combination of comfort, style, and convenience. Simply unpack and start enjoying everything this beautiful property has to offer. Step inside to discover gorgeous hardwood floors flowing throughout the main living areas, complemented by beautiful tile flooring in the kitchen. The heart of the home features a stunning eat in kitchen with upgraded cabinetry, beautiful appliances, and ample workspace, making it as functional as it is beautiful. The thoughtfully designed layout includes a spacious family room, 3 generously sized bedrooms and a beautiful full bathroom! The immaculate full basement offers endless possibilities, whether you envision additional living space, a home gym, workshop, or simply appreciate the incredible amount of clean storage. A large two car garage provides even more room for vehicles, tools, and recreational equipment. Outside, you'll find your own private retreat. The incredible ground-level patio creates the perfect setting for relaxing, dining outdoors, or entertaining guests while overlooking the peaceful backyard surrounded by nature for exceptional privacy. A large turnaround driveway makes coming and going effortless, while the home's custom landscaping, enhances the curb appeal. Ideally situated in an outstanding Middletown location, you'll enjoy the tranquility of a quiet setting without sacrificing convenience. Shopping, restaurants, parks, schools, and major commuter routes are all just minutes away, making this the perfect place to call home. With its impeccable condition, tasteful updates, and unbeatable location, this move in ready ranch is a rare opportunity you won't want to miss. Call today to schedule your private showing. This immaculate home is an absolute must-see!

30 Murray Road, Middletown

$575,000

4 Beds ⋅ 3 Baths ⋅ DENC2108130 MLS

Coming Soon! Showings start Saturday, Aug 1st. Welcome to this nicely maintained 4-bedroom, 2.5-bath home, the largest model in the community, featuring neutral décor throughout and numerous recent updates. Major improvements include a new tankless gas water heater (2026), and new luxury vinyl plank flooring in the kitchen and primary bath (2026) dual zone HVAC (2025 & 2018) , and Roof replacement in 2018. Enter the main level into the 2-story foyer. On your right is the first floor office that provides the ideal work-from-home space. To your left are the living room and dining room, and then the eat-in kitchen which features a center island for additional work space, quartz countertops, stainless steel appliances. It opens seamlessly to the inviting family room. It also has a newer slider door (2019) that exits to the deck and fenced rear yard. Upstairs you will find the generously-sized primary suite featuring a private bath with soaking tub, separate shower, dual vanities, and an oversized walk-in closet. The conveniently located laundry, three additional bedrooms and another full bath complete the second level. The finished basement offers exceptional flexibility with a large game room, an additional bonus room with a closet, that can serve as a fifth bedroom, office, or hobby space, plus abundant storage in the unfinished area. Rough-in plumbing is already in place for a future third full bathroom. Outdoor living is equally impressive with a maintenance-free deck with a retractable awning, rear patio with privacy fencing and existing electric for a hot tub, thoughtfully landscaped backyard lined with Arborvitaes for added privacy, split-rail fencing, and an included storage shed. Located in the highly sought-after Appoquinimink School District, this home offers a convenient location close to shopping, dining, parks, and major commuting routes. This wonderful home combines space, comfort, and thoughtful updates—don't miss the opportunity to make it yours! Notes: Sq ftg was taken from NCC website. Buyer should satisfy themselves as to it's accuracy. Property receives Town of Middletown services.

116 E Minglewood Dr, Middletown

$569,000

3 Beds ⋅ 2 Baths ⋅ DENC2107742 MLS

Move right into this stunning K. Hovnanian Magnolia home located in the highly desirable Four Seasons at Silver Maple Farm community in Middletown! You will be immediately greeted by the stone front, lush curb appeal and charming covered front porch. Continue your tour inside where you’ll find your gourmet kitchen with luxury granite countertops, custom tile backsplash, recessed lighting, extended cabinets with crown molding, and upgraded stainless steel appliances. Solid hardwood flooring flows beautifully throughout all the living spaces. The open concept floor plan with recessed lighting is perfect for entertaining. Enter the living room that offers breathtaking vaulted ceilings and gas fireplace centerpiece. This home is perfect for one floor living with a main-floor laundry and a convenient office/third bedroom. Your spacious primary bedroom with massive wall-to-wall walk-in closet, en-suite with double vanities and extra wide tiled walk-in shower. A second bedroom and a full bathroom with tile surround are also on this level. The outdoor space offers an extended composite deck and backs up to private lush green space, perfect for relaxing or entertaining. Four Seasons at Silver Maple Farms amenities can’t be beat with an expansive clubhouse, a calendar of engaging activities for residents, along with indoor amenities that include community gathering space, kitchen, hearth room, fitness center, card room, yoga room, billiards room and ping-pong room. Outdoor amenities include the swimming pool with Tiki bar and BBQ area, tennis and pickle ball courts, bocce and horseshoe courts, miles of walking trails and a community garden. No need to worry about lawn care as it is included! Located a short drive to major highways like Route 1 and I-95, Delaware Beaches, main waterways, popular shopping, dining and more. Schedule your tour today!

239 Silky Dogwood Ln, Middletown

$539,900

4 Beds ⋅ 3 Baths ⋅ 1031777 MLS

Welcome to this beautifully maintained Center Hall Colonial offering the perfect blend of classic design and comfortable everyday living. The heart of the home is the spacious kitchen, which opens seamlessly to the inviting family room, creating an ideal space for gathering with family and friends. The family room is highlighted by custom built-in shelving and a cozy wood-burning fireplace, adding warmth and character. This home features four generously sized bedrooms and three bathrooms, providing plenty of space for family, guests, or a home office. The basement offers additional flexible living space perfect for a recreation room, fitness area, media room, or playroom. Outside, the newly paved walkway creates an attractive first impression and welcomes you home. Situated across from the Shawangunk Fish & Game Association, the property enjoys a unique setting with convenient access to outdoor recreation and open space. Combining timeless Colonial charm with functional living spaces and thoughtful updates, this home is ready to welcome its next owners.

31 Denman Road, Middletown

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