Middletown Real Estate

Middletown Real Estate

Welcome to Middletown, a charming city nestled in the heart of the United States, where small-town charm meets modern conveniences. Known for its friendly community and picturesque landscapes, Middletown offers a delightful blend of urban amenities and natural beauty, making it an ideal place to call home.

Middletown boasts a rich history, with roots dating back to the 18th century. The city is adorned with beautifully preserved architecture that tells the story of its past, while also embracing contemporary developments that cater to today’s lifestyles. Residents enjoy a vibrant downtown area filled with unique shops, cozy cafes, and a variety of dining options that cater to every palate.

Nature lovers will find plenty to explore in Middletown’s surrounding parks and recreational areas. With miles of scenic trails, lush green spaces, and serene lakes, outdoor activities such as hiking, biking, and fishing are just a stone’s throw away. Families can take advantage of the many community events held throughout the year, fostering a strong sense of belonging and connection among residents.

Education is highly valued in Middletown, with excellent schools and educational programs that prepare students for success. The city also offers a variety of cultural attractions, including art galleries, theaters, and museums, making it a hub for creativity and expression.

Whether you’re looking to buy your first home, settle down, or invest in a property, Middletown is a place where you can thrive. Experience the warmth of this inviting community and discover why so many choose to make Middletown their forever home.

Newest Listings in Middletown

$149,900
2 Beds ⋅ 1 Baths
*PROPERTY CAN ONLY BE ACCESSED BY BOAT* Nestled along the serene banks of the Susquehanna River, this charming seasonal cottage offers a perfect blend of comfort and tranquility. With its inviting open floor plan, this residence is designed to create a warm and welcoming atmosphere, ideal for both relaxation and entertaining. Step inside to discover a cozy living space adorned with carpeting and thoughtful window treatments that allow natural light to fill the rooms. The heart of the home features a well-appointed kitchen equipped with essential appliances, including a refrigerator, stove, microwave, and icemaker, making meal preparation a delight. The open layout seamlessly connects the kitchen to the living area, fostering a sense of togetherness. The home boasts two spacious bedrooms, each designed to provide a peaceful retreat at the end of the day. The full bathroom is conveniently located, ensuring comfort and accessibility for all. A unique spiral staircase adds character and charm, leading to additional living space or storage options, perfect for personalizing to your needs. Outside, the property spans a generous 0.35 acres, offering ample space for outdoor activities or simply enjoying the picturesque views of the river. You can indulge in the beauty of nature right from your yard. A private floating dock awaits, providing easy access to the river for fishing, kayaking, or simply soaking in the serene surroundings. The location is truly a gem, offering a peaceful riverfront lifesty while still being conveniently accessible to local amenities. Whether you're looking for a weekend or summer getaway, this home provides the perfect backdrop for creating lasting memories. This property is a rare find. Embrace the opportunity to live in a cottage that not only meets your needs but also enhances your lifestyle. Experience the joy of riverfront living and make this charming home your own. Dont wait schedule your showing today the river season is not over just yet! Seller is a licensed real estate agent

18 Beech Island Isl, Middletown

Listing courtesy of RE/MAX Quality Service, Inc.. Contact: (717) 632-5111
$418,500
3 Beds ⋅ 3 Baths
Enjoy the Middletown lifestyle with space, convenience, and a location that keeps you close to it all! Welcome to 323 Gaither Drive, a spacious 3-bedroom, 2.5-bath townhome offering approximately 2,200 square feet of living space and a hard-to-find 2-car attached garage. The three-level design offers plenty of room to spread out, with a versatile main-level sitting room and an expansive second-floor living area perfect for everyday living and entertaining. The kitchen and dining area flow comfortably into the main living space, while all three bedrooms are privately located on the upper level, including a generously sized primary suite with its own full bath. What really sets this home apart is the Middletown location. Enjoy a more walkable lifestyle with shopping, dining and everyday conveniences nearby, while still having easy access to everything the greater Middletown area has to offer. Located within the Appoquinimink School District and inside Middletown town limits, this is a great opportunity to enjoy the energy and convenience of one of Delaware's most popular communities. And an added bonus—NO HOA! With generous living space, a 2-car garage and a convenient Middletown location, 323 Gaither Drive offers a combination that's increasingly hard to find.

323 Gaither Dr, Middletown

Listing courtesy of Century 21 Gold Key Realty. Contact: 3023695397
$229,900
3 Beds ⋅ 2 Baths
Nestled in the charming community of Middletown Borough, this exquisite semi-detached home, built in 1915, seamlessly blends traditional elegance with modern comforts. With 1,319 square feet of thoughtfully designed living space, this residence invites you to experience a lifestyle of warmth and sophistication. Step inside to discover a welcoming interior adorned with rich wood floors and plush carpeting that create an inviting atmosphere throughout. The spacious living area features a cozy gas fireplace, perfect for gathering with loved ones on chilly evenings. Natural light pours in through double-hung, insulated, and triple-pane windows, enhancing the home's warmth and energy efficiency. The galley kitchen is a culinary delight, equipped with a gas oven/range and a refrigerator, offering both functionality and style. Built-in cabinetry provides ample storage, while the adjacent dining area is ideal for intimate meals or entertaining guests. The main level also boasts a convenient half bath, ensuring comfort for both residents and visitors. Ascend to the upper level, where three well-appointed bedrooms await, each offering a serene retreat for rest and relaxation. The full bathroom features a classic tub shower combination, providing a perfect blend of luxury and practicality. An attic adds additional storage space, catering to all your organizational needs. Outside, the property is framed by well-maintained sidewalks and street lights, enhancing the neighborhood's charm. The level lot, spanning 0.04 acres, offers a manageable outdoor space, perfect for gardening or enjoying a quiet moment in the fresh air. On-street parking ensures convenience for you and your guests. This home is ideally located within a short distance to public transportation options, including a bus stop less than a mile away and a commuter rail station within five miles, making it easy to explore the surrounding areas. Experience the perfect blend of historic charm and modern living in this delightful Middletown Borough residence. With its high-end features and inviting ambiance, this property is not just a house; it's a place to call home. Embrace a lifestyle of comfort and elegance in this exceptional offering. 1 year home warranty offered!

174 E Emaus St, Middletown

Listing courtesy of Keller Williams Elite. Contact: 7175532500
$225,000
3 Beds ⋅ 2 Baths
Charming three-bedroom, one-bathroom home in Middletown offering a comfortable layout and plenty of potential. One bedroom is conveniently located on the main level, while the updated kitchen features a welcoming feel and a separate dining area perfect for everyday meals or entertaining. The full basement provides ample space for storage, hobbies, or future possibilities. Outside, enjoy a partially fenced backyard, two storage sheds, and a large covered deck that offers a great spot to relax and enjoy the outdoors. This charming home has plenty to offer and is a must-see!

653 Briarcliff Rd, Middletown

Listing courtesy of ADP Realty & Property Management LLC. Contact: 7173707001
$739,990
3 Beds ⋅ 4 Baths
Brand New 55+ Community in Middletown, DE Welcome to the Carver, a beautifully designed home that combines an open-concept layout with plenty of natural light. Scheduled for settlement in October 2026, this home offers 3 bedrooms, 3.5 baths, and a 2.5-car garage, providing a comfortable blend of style and functionality. A welcoming front porch creates charming curb appeal, while the screened deck offers an inviting space to enjoy the outdoors. Inside, the finished basement provides additional living space, and a fireplace adds warmth and character to the main living area. The spacious kitchen features a huge island and quartz countertops, perfect for cooking, gathering, and entertaining. Laminate flooring throughout the first floor offers a cohesive and stylish finish, while the bathrooms feature a walk-in shower with tile walls. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

1620 Jaymes Cir, Middletown

Listing courtesy of Delaware Homes Inc. Contact: 3023789510
$680,000
5 Beds ⋅ 3 Baths
Step into a world of timeless elegance with this stunning Victorian home, a true masterpiece of craftsmanship and design. Built in 1900, this residence boasts and shows a life of owners who loved it and those who appreciated its unique architectural features. Beautiful hardwood floors throughout the entire home, including in the updated and modernized kitchen! Upgraded countertops and stainless steel appliances, including a dishwasher, 40" dual-fuel range and refrigerator. An extra refrigerator/freezer in the basement provide ample storage for all your culinary needs. The main floor laundry acts as a separator and tie between the rest of the house and the "in-law" suite which was once the summer kitchen. Retreat to one of the five generously sized bedrooms, each offering a peaceful haven for rest and relaxation. The home boasts 3 fireplaces, one fully flued for log burning, and though the other two are sealed off, the one in the kitchen has a wood-style, ventless propane stove installed. The bathrooms are thoughtfully designed, featuring walk-in showers, glass doors and electric, radiant-heat tile floors. One bathroom has even had accessibility in mind making it a "wet room" for those with mobility issues. Outside you will find no detail missed, as even the exterior shingles were hand scalloped to properly match the original victorian look and design. The front porch is inviting and relaxing to watch traffic drive by on their way through Middletown, and the sleeper porch allows you to have some peace and quiet while enjoying nature. With nearly a third acre lot, there's plenty of room for outdoor activities or gardening. This Victorian gem is not just a house; it's a place where memories are made, and stories are shared. Experience the perfect blend of classic elegance and contemporary comfort-your dream home awaits!

21 E Main St, Middletown

Listing courtesy of Maryland Real Estate Group. Contact: (301) 865-2037
$255,000
Totally rehabbed 2 unit with garage for extra rental space! One unit is rented for 1100 a month and 3 bedroom unit is vacant ready for a new tenant or a great place to move in yourself! Brand new kitchens, new bathrooms, all new vinyl plank floors and carpet, new appliances, freshly painted, updated electric and much more! Property is located in Middletown borough, land is leased.

129 Poplar St, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 7175342442
$64,900
3 Beds ⋅ 1 Baths
Welcome home to this beautifully renovated 3-bedroom, 1-bath mobile home located in Little Hollywood Mobile Home Court! Freshly updated and move-in ready, this home offers a bright and welcoming interior with comfortable living spaces and a functional layout. The renovations give the home a fresh, modern feel while offering an affordable opportunity to enjoy homeownership. With three bedrooms, there is plenty of flexibility for family, guests, a home office, or additional storage. Conveniently located in Middletown with easy access to shopping, dining, major roadways, and local amenities. All that’s left to do is move in and make it your own. Schedule your showing today!

109 Nancy Blvd, Middletown

Listing courtesy of NextHome Dream Seekers Realty). Contact: 7178025614
$300,000
3 Beds ⋅ 2 Baths
Welcome to this inviting bilevel home situated on a desirable corner lot with an amazing yard and fresh landscaping! Step inside the foyer and head upstairs to the main level, where the spacious living room features plush carpeting and a cozy gas fireplace. The formal dining room offers vinyl flooring and convenient outdoor access, while the eat-in kitchen provides plenty of cabinet space, a pantry for storage, vinyl flooring and a ceiling fan. Three generous bedrooms and a full bath complete the main level. Enjoy the changing seasons from the carpeted sunroom, a wonderful additional space to relax and take in views of the outdoors. The lower level offers even more living space with two additional bedrooms and a full bath, along with a spacious family room featuring exposed wood beams, chair railing, window treatments and a wet bar—perfect for entertaining or relaxing with family and friends. Outside, the deck overlooks the cleared backyard, providing a great setting for outdoor gatherings, play or simply enjoying your own private space. An oversized two-car garage offers plenty of room for vehicles, storage and more. Conveniently located near shopping, dining and entertainment, this well-loved home offers space, versatility and a location that is hard to beat. A joy to own!

1720 Oberlin Rd, Middletown

Listing courtesy of Joy Daniels Real Estate Group, Ltd. Contact: 7176953177
$598,000
3 Beds ⋅ 4 Baths
*MOVE IN READY* Welcome home to 3024 Ivyhouse Lane! Available for immediate move-in, this beautifully designed 3,223-square-foot Mendocino Luxe offers the perfect blend of space, comfort, and style. With 3 bedrooms, 4 bathrooms, a first-floor owner's suite, and a partially finished basement with a full bathroom, there's room for everything—from hosting family and friends to creating the perfect place to unwind. Located in the sought-after Venue at Winchelsea in Middletown, Delaware, the Mendocino Luxe floorplan is thoughtfully designed for comfort and luxury. Two versatile flex rooms welcome you off the foyer, leading into an open-concept living space that seamlessly connects the gourmet kitchen, dining area, and great room. Step into the sun room or outside to the covered rear porch—perfect for relaxing, entertaining, or enjoying the changing seasons. The partial finished basement with a full bathroom adds valuable living space, giving you the flexibility to create a home that fits your lifestyle. Tucked away at the back of the home, the luxurious owner's suite features a spa-inspired en-suite bathroom and two spacious walk-in closets. Upstairs, a generous loft provides the perfect setting for a media room, hobby space, home office, or cozy retreat. Don't miss your opportunity to call Venue at Winchelsea home! ** Please Read: Photos are for illustrative purposes only and may include renderings or images of the actual home or similar home/plan. Please see New Home Consultant for final pricing, finishes, and details. If you are working with a realtor, buyer representation must be acknowledged during the first interaction with Lennar, and the Realtor must accompany the client on their first visit. Appointments are highly encouraged to ensure the best customer experience. Taxes will be assessed after settlement. Open houses are held at the model home, not at this address. During your visit the sales team can review details, timelines, and current incentives. Financing is available through Lennar Mortgage upon qualification. ** For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.*

3024 Ivyhouse Ln, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339
$675,000
4 Beds ⋅ 4 Baths
Professional photos coming soon! WHERE HOME MEETS HOMETOWN! Beautifully built in 2019 and ideally located on a premium corner homesite, this exceptional Colonial offers the rare combination of a beautifully appointed, move-in-ready home and the welcoming lifestyle of Historic Middletown, one of Maryland's most desirable small towns. With three finished levels, four bedrooms, 3 full and 1 half baths, a covered front porch, a covered rear maintenance-free deck, and a location where schools, restaurants, the recently built library, community parks, and Historic Main Street are all within easy reach, this is a home designed to be lived in, enjoyed, and remembered. From the moment you arrive, the covered front porch invites you to slow down and enjoy the neighborhood and serene mountain views. Inside, the light-filled open floor plan creates an effortless flow for both everyday living and entertaining. Beautiful, engineered wood flooring throughout the main level, high ceilings, and an abundance of windows give the main level a bright, welcoming feel. The private office with French doors offers the perfect place to work from home, while the heart of the home is undoubtedly the spacious kitchen, breakfast/dining area, and family room. Gather around the oversized island in the gorgeous kitchen featuring timeless white cabinetry, quartz countertops, stainless steel appliances, gas range, wall oven, built-in microwave, dishwasher, refrigerator, and plenty of workspace for preparing everything from weekday meals to holiday dinners. The kitchen opens to the breakfast/dining area and family room, making it easy to stay connected with family and guests. A gas fireplace adds warmth and ambiance, while the extra windows bring the outdoors in. Just beyond the kitchen, the covered maintenance-free deck creates another inviting place to relax, dine al fresco, or gather with friends. A convenient rear hallway includes a pantry closet, powder room, coat closet, and access to the two-car garage. Upstairs, the spacious primary suite feels like a private retreat, complete with room for a sitting area, massive walk-in closet, and beautifully appointed ensuite bath with walk-in shower, dual-sink vanity, and private toilet room. Three additional bedrooms provide space for family, guests, hobbies, or a second home office. One bedroom features a large picture window that fills the room with natural light. The convenient upper-level laundry room with built-in shelving and full hall bath add to the thoughtful functionality of this level. The finished lower level adds an entirely new dimension to the home with a generous recreation room and walkout to a paver pad and the rear yard, along with a full bath, storage room, and utility room. Whether envisioned as a game room, movie night destination, guest space, exercise area, or simply a place to spread out, this flexible level adapts beautifully to your lifestyle. Freshly painted interiors, newly installed carpeting, a tankless water heater, natural gas heat, and an exceptionally well-designed floor plan make this home truly move-in ready. But perhaps what makes this property most special is the life you can live here. Step outside, and you're part of a community where neighbors gather, traditions matter, and there is always something to look forward to. Walk to Historic Main Street for restaurants and local events, enjoy Friday night football, stroll to the library, hear the church bells ring, or spend an afternoon at nearby Middletown Community Park with its trails, playgrounds, soccer and football fields, fishing pond, picnic areas, sand volleyball, disc golf, bandstand, and more. Middletown has a way of taking you back to a simpler time with holiday celebrations, parades down Main Street, outdoor movies, concerts in the park, and the familiar rhythm of a community that comes together. This is more than a beautiful house. It is a place to put down roots, make memories, and truly enjoy coming home.

12 Dean Ln, Middletown

Listing courtesy of Monument Sotheby's International Realty. Contact: (443) 746-2090
$874,900
3 Beds ⋅ 3 Baths
23+ ACRES *** 4,000+ TOTAL FINISHED SQ. FT. *** HORSE BARN *** TRAILS *** MIDDLETOWN VALLEY A rare opportunity to enjoy space, privacy and versatility in the heart of scenic Middletown Valley. Set on approximately 23.1 acres, this distinctive property brings together a spacious residence, expansive open acreage, equestrian improvements, a substantial barn and beautiful countryside surroundings—all while remaining convenient to Middletown and Frederick. The home offers more than 4,000 total finished square feet, with generous gathering spaces designed to take advantage of the property’s natural setting. One of the highlights is the impressive window-lined living/sunroom area, where abundant natural light and views of the surrounding acreage create a wonderful connection between the indoors and outdoors. A second expansive living area features a wood-burning stove, skylights and walls of windows overlooking the property. The main level offers a comfortable and functional layout with a primary bedroom suite featuring a private bath and walk-in closet, two additional bedrooms and another full bath. The spacious kitchen features granite countertops, stainless steel appliances, upgraded cabinetry and a large casual dining area, complemented by separate living and dining spaces. Hardwood flooring extends through much of the main level. The lower level significantly expands the home's usable space and offers excellent flexibility for recreation, guests, extended living arrangements, hobbies or a home office. Additional features include the laundry area and plumbing rough-in for another full bathroom. Outside is where this property becomes truly special. Step onto the large rear deck with a covered section and enjoy views across your own acreage. The property has been enhanced with trails throughout the land, creating opportunities for horseback riding, walking, recreation and simply enjoying the privacy of the setting. The deck and gazebo have also been repaired and refreshed. For the equestrian enthusiast, hobby farmer, collector or buyer simply looking for substantial additional space, the approximately 42' x 70' barn is an exceptional feature. The barn has its own electrical panel, an upper level and three horse stalls, providing substantial room for horses, equipment, storage, workshops or other permitted uses. Horse containment areas have also been improved. And despite the peaceful country setting, you don't have to give up convenience. Historic Main Street Middletown offers locally owned restaurants, shops and services, while the surrounding Middletown Valley is known for its mountain scenery, farmland and outdoor recreation. The Appalachian Trail, South Mountain area and Middletown's parks and walking trails add even more opportunities to enjoy the outdoors. For more extensive shopping, dining and entertainment, Downtown Frederick offers more than 200 specialty shops, galleries, breweries, distilleries and restaurants. The Middletown area is positioned along the historic US-40 Alternate/National Road corridor, providing connectivity toward Frederick and the surrounding region. 23+ acres. 4,000+ finished square feet. Horse facilities. An oversized barn. Trails. Privacy. Mountain-country surroundings. Properties offering this combination of acreage, living space and versatility in Middletown are difficult to duplicate.

2313 Bidle Rd, Middletown

Listing courtesy of Taylor Properties. Contact:

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