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$1,300,000
3 Beds ⋅ 3 Baths
Tucked away on 11 pristine, private acres in Middletown, this home offers a rare blend of sweeping natural beauty, effortless single-level luxury, and incredible versatility. From the moment you pull up the drive, the gorgeous, park-like setting establishes a profound sense of peace and privacy that is hard to find, yet keeps you incredibly close to local conveniences. Step inside the main residence and you are immediately greeted by the warmth of rich hardwood floors and the airy, expansive feel of soaring vaulted ceilings. Designed for seamless everyday living and effortless entertaining, the heart of this home is a true gourmet kitchen. Outfitted with gleaming quartz countertops and top-of-the-line stainless steel appliances, it flows beautifully into both the inviting family room and the grand great room. Whether you are hosting holiday dinners or enjoying quiet mornings watching the sunrise over your acreage, this layout adapts perfectly to your lifestyle. The main home features three spacious bedrooms and two and a half baths, including a serene primary retreat. A dedicated first-floor office provides the ideal, quiet sanctuary for remote work or creative pursuits, tucked away from the main living areas. Just steps away sits a remarkable asset: a fully detached, separate second dwelling. This self-contained space is perfect for multi-generational living, long-term guests, or an inspiring studio. It features a bright loft, a large, comfortable great room, a convenient kitchenette, one bedroom, and two full bathrooms—offering complete independence and comfort without sacrificing privacy. Completing this exceptional estate is an oversized, three-car detached garage, offering abundant space for vehicles, a workshop, or recreational storage. This isn't just a home; it’s a private retreat where modern luxury meets eleven acres of quiet, gorgeous Delaware countryside. You have the opportunity to purchase an additional 14 acres, MLS NUMBER MLS# DENC2098214 & tax ID 13-012.00-151 to make this a wonderful 26 acre estate!

864 Old School House Rd, Middletown

Listing courtesy of Thyme Real Estate Co LLC. Contact: 3026900245
$540,000
3 Beds ⋅ 3 Baths
PRICED TO SELL ✅ Low-maintenance HOA living ✅ Community pool ✅ Updated kitchen ✅ Bonus room ✅ Finished basement ✅ Prime location near Routes 1, 13 & 301 Don't worry about cutting the grass or shoveling snow!! Our HOA handles that, allowing you to enjoy your weekends relaxing by the community pool. HOA fees also include common area maintenance and snow removal. This spacious 3-bedroom home with a VERSATILE BONUS ROOM offers a thoughtfully designed layout and numerous updates throughout. The inviting family room with fireplace opens seamlessly to the center-island kitchen with a bar area at the island , now updated with a new stove, microwave, dishwasher, refreshed countertops, and a stylish backsplash, making it perfect for both everyday living and entertaining. Just off the kitchen you’ll find a convenient mudroom, pantry closet, half bath, and garage entry. Upstairs, the spacious primary suite boasts a tray ceiling, double vanities, his and her walk-in closets, and a beautifully tiled shower. Two additional bedrooms are generously sized, and the bonus room can be used as a den, home office, or playroom. The laundry room is conveniently located on this level. The full basement provides exceptional additional living space with a second family room, a large storage area, and a utility room. Plumbing is already roughed in for a future bathroom, and the water heater was replaced in 2019. Location Location Location!! Minutes from Routes 1, 13, and 301 with no tolls to go north and a grocery store 5 minutes away!

336 Acasta Dr, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 3022341888
$774,900
6 Beds ⋅ 5 Baths
Offering just over 3900 finished square feet, 6 bedrooms, 5 full bathrooms, a main level bedroom with access to a full bath, a 1-acre lot, no HOA, and a peaceful setting in a golf course community, this home is designed for both everyday living and entertaining. Mountain views, an 880 square foot Trex deck, a roof that's only 5 years old, and a flexible floor plan complete the package. The main level features hardwood floors through most of the living areas, a bedroom with convenient access to a full bath, formal living and dining rooms, a two story (18ft tall) foyer, laundry room, and a spacious kitchen. The updated kitchen features quartz countertops, subway tile backsplash, freshly painted cabinetry, and stainless steel appliances. Upstairs you'll find five bedrooms, including a spacious primary suite with a jetted garden tub, tiled shower, double vanity, and walk in closet. Three additional bedrooms share a full bath with double sinks. There's also a junior suite at the end of the hall with its own private full bath, making it a great option for guests or multigenerational living. The partially finished walkout basement offers even more flexible living space with two finished rooms, a full bathroom, and a large unfinished storage and mechanical room. The current media room and game room setup provides plenty of possibilities for entertaining, hobbies, a home office, or guest space. Outside, the fully fenced backyard offers plenty of open space for entertaining, recreation, pets, or simply enjoying the peaceful setting. The spacious Trex deck, completed in 2024, offers plenty of room for outdoor dining, relaxing, or gathering with family and friends. A side porch extends the outdoor living space and opens to its own separate fenced area, creating a private space that's ideal for pets, young children, or even a garden. Recent improvements include the 2024 Trex deck, backyard and side yard fencing, refinished and expanded hardwood flooring (including the main staircase), fresh interior paint, fireplace surround and mantel, quartz countertops, updated lighting, insulated garage doors and openers, extensive HVAC and plumbing improvements, radon mitigation, and smart home features including Nest thermostats, Ring cameras, and a Schlage smart lock. The extensive list of recent improvements reflects the care and investment the current owners have made throughout the home. (See attached document for full detailed list of improvements.) Located in an established neighborhood surrounded by Sly Fox Golf Club, the home offers a peaceful setting while remaining just five minutes from I-66 and ten minutes from I-81. The sellers would also consider selling the home fully furnished (to include the basement theater equipment, seating, game tables and riding lawn mower) through a separate agreement, creating a true move in ready opportunity. (See attached document for full detailed list of items.) Shown by appointment only.

80 Little Sorrel Dr, Middletown

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$415,000
3 Beds ⋅ 2 Baths
Price Reduced!! Welcome to this beautifully maintained brick Cape Cod, tucked away on a private 0.70-acre cul-de-sac lot in Middletown! Thoughtfully updated and meticulously cared for, this home offers the perfect blend of charm, comfort, and outdoor living. Step inside to find fresh interior paint, hardwood floors, updated bathrooms, and a spacious living room featuring a new gas fireplace with thermostat and remote, creating a warm and inviting gathering space. The 20' x 10' sunroom is the perfect place to relax while enjoying peaceful views of the beautifully landscaped backyard. The main-level primary bedroom provides convenient one-level living. Outside is where this property truly shines. The professionally landscaped front yard features a beautiful picket fence with decorative arch, weeping cherry tree, Japanese maple, azaleas, and a raised stone flower bed connected by a charming brick walkway. Garden enthusiasts will appreciate the established butterfly garden, raised garden beds, and mature asparagus. The fully equipped chicken coop is ready for your flock, while the yard attracts abundant wildlife, creating a peaceful country setting. Additional highlights include an oversized one-car garage with floored storage above, an outbuilding/workshop with wood stove (plus a cord of seasoned split firewood), Andersen windows, a new insulated garage door, and owned solar panels that convey free and clear, helping reduce utility costs. For added peace of mind, the sellers have completed a pre-sale home inspection, addressed the noted items, and recently installed a brand-new hot water heater and new chimney cap. A new Samsung washer and the sauna also convey with the home. Located at the end of a quiet cul-de-sac, this move-in-ready home offers exceptional privacy, beautiful landscaping, and countless thoughtful updates—making it a rare opportunity in the Middletown area.

2105 Shawn Dr, Middletown

Listing courtesy of Real Broker, LLC. Contact: 8504500442
$775,000
5 Beds ⋅ 5 Baths
Welcome to 201 Parker Drive, an exceptional residence nestled in the highly sought-after Crossland at the Canal community, where elegant design, luxurious amenities, and energy-efficient living come together in one remarkable home. Offering five bedrooms, four full bathrooms, and one half bath, this beautifully appointed property welcomes you with a bright two-story foyer and hardwood flooring throughout the main level. A private office with custom built-in shelving provides the perfect work-from-home space, while the formal living and dining rooms seamlessly transition into the spacious family room with a cozy fireplace. The gourmet kitchen is thoughtfully designed for both everyday living and entertaining, featuring granite countertops, abundant cabinetry, and a large center island that serves as the heart of the home.The finished walk-out lower level is an entertainer's dream, featuring a wired home theater, an expansive recreation area, a custom wet bar complete with dual wine coolers, an additional bedroom, and a full bathroom, creating the ideal space for hosting guests or multi-generational living. Upstairs, the luxurious primary suite offers a private sitting room highlighted by a custom dry bar with dual wine coolers, creating the perfect retreat for relaxing at the end of the day. One of the secondary bedrooms has been professionally transformed by Closet by Design into an impressive boutique-style walk-in dressing room and can easily be converted back into a full bedroom if desired. Even the laundry room has been thoughtfully upgraded with a built-in wall-mounted ironing board for added convenience.Step outside to your own private backyard oasis featuring a heated saltwater in-ground swimming pool with lighting, perfect for enjoying warm summer days and unforgettable evenings with family and friends. This exceptional home is loaded with premium upgrades, including a new roof installed in 2025, a Generac whole-house generator, an electric vehicle charging station, and transferable solar panels that provide outstanding energy efficiency and long-term savings. Combining luxury finishes, thoughtful customizations, and major system improvements, this home delivers both comfort and peace of mind for years to come. Located within the desirable Crossland at the Canal community and convenient to shopping, dining, parks, and major commuter routes, 201 Parker Drive presents a rare opportunity to own a truly turnkey home that offers the perfect balance of luxury, functionality, and modern efficiency. This is more than a home—it's a lifestyle.

201 Parker Dr, Middletown

Listing courtesy of Century 21 Emerald. Contact: 3027981000
$379,000
4 Beds ⋅ 2 Baths
An exceptional opportunity to restore and reimagine a historic Main Street property in the heart of Middletown. Prominently located along one of the towns most recognized corridors, this four bedroom, two bath home offers timeless character, outstanding potential, and a location that is difficult to duplicate. Believed to date to the early 1800s, the home has been part of Middletown history for generations and is ready for its next chapter. Just a short walk to local shops, restaurants, cafes, and community gathering spaces, this property offers the charm and convenience of small town living. Situated on a generous in town parcel with desirable B1 zoning, the property provides exceptional flexibility for residential living, professional office, business use, or a mixed use concept subject to local approvals. The additional side land offers potential subdivision opportunities subject to application and approval. Rear alley access further enhances the versatility of this unique property while the prominent Main Street location provides outstanding visibility for a variety of future uses. Inside, the home features four bedrooms, two full baths, and the character expected of a historic residence. The property is ready for restoration and thoughtful updating, presenting an exceptional opportunity to preserve its historic charm while incorporating modern improvements. Whether your vision is a distinctive residence, professional office, investment property, or live and work opportunity, the possibilities are substantial. Historic Main Street properties offering this combination of character, location, flexible B1 zoning, additional land, rear alley access, and future potential rarely become available. Property is being sold as is.

7927 Main St, Middletown

Listing courtesy of Coldwell Banker Premier. Contact:

$649,900
5 Beds ⋅ 4 Baths
Welcome to 601 Yensid Drive, where space, comfort, and style come together in the desirable community of Crossland at the Canal. This beautifully maintained 5-bedroom, 3.5-bath Colonial offers over 3,800 square feet of thoughtfully designed living space, featuring gleaming hardwood floors throughout, an open floor plan, and a gourmet kitchen. The kitchen has lots of prep space with granite countertops, stainless steel appliances, abundant cabinetry, a center island, and a sunny eat in area that flows seamlessly into the sunroom and the spacious family room. This floor plan lends itself to entertaining due to the flow from the formal living room open to the formal dining room and then to the huge family room open to the kitchen and sunroom. Whether you entertain or not, you will love the openness. Upstairs, you'll find 4 generously sized bedrooms, including a spacious primary suite with a large walk-in closet and private bath and laundry is located upstairs. The finished lower level adds incredible flexibility with a full bath, bedroom and plenty of room for a recreation area, home gym, office, or guest space. There is also a daylight walkout and an egress window. Outside, enjoy a beautifully landscaped yard with plenty of room to relax or entertain. Residents also enjoy access to the community pool and clubhouse. All is just minutes from shopping, dining, and major commuter routes. This is a home you'll want to experience in person. With its generous living spaces, thoughtful layout, and exceptional community amenities, 601 Yensid Drive is ready to welcome you home.

601 Yensid Dr, Middletown

Listing courtesy of Compass. Contact: 3022029855
$735,000
5 Beds ⋅ 3 Baths
Welcome to 362 Neverland Dr in Middletown, Delaware — a beautifully upgraded home offering space, privacy, flexibility, and lifestyle features in one of Delaware’s most desirable and fast-growing towns. Perfectly positioned on a premium wooded lot with no rear neighbors, this home offers peaceful views, added privacy, and the rare feeling of not looking directly into another backyard. From the moment you arrive, the thoughtful upgrades stand out. The sellers made a significant investment in expanding the driveway to allow three cars to park side by side, while the widened walkway and upgraded larger front steps create a polished and welcoming entry. These improvements add both curb appeal and everyday convenience. Inside, the main level offers a formal living room and dining room, a spacious family room, and a private home office that can function as an office, guest room, playroom, or flexible bedroom-style space. This layout is ideal for buyers who need more than standard bedrooms, including work-from-home needs, extended guest stays, or multi-generational living possibilities. At the heart of the home is a gourmet kitchen with a large center island, double ovens, and excellent flow into the main living areas. Whether hosting holidays, preparing meals, or gathering with family and friends, this kitchen was designed for both everyday living and entertaining. Luxury vinyl plank flooring runs throughout the main and upper levels, giving the home a clean, modern, and cohesive feel. The spacious primary suite is a true retreat, featuring a luxury bath with a walk-in shower, garden tub, double sinks, and two large walk-in closets. The two walk-in closets are a standout feature that buyers will immediately appreciate, offering the storage and functionality many homes simply do not provide. The finished basement adds another impressive level of living and entertainment space. Enjoy a dedicated theater room featuring in-ceiling surround sound speakers, a 5.1 audio setup, Denon equipment, and subwoofers that may convey with the sale. The first-floor family room also features in-ceiling surround sound speakers, giving the home upgraded audio on two levels — perfect for movie nights, game days, music, entertaining, or everyday enjoyment. The basement also includes an open finished area that can serve as a recreation room, lounge, game room, guest space, hobby area, or future bedroom-style flex space. For buyers seeking multi-generational potential, additional living options, or room to grow, this basement offers outstanding adaptability. There is also an unfinished gym/workout area with rough-ins for a future full bathroom, creating even more possibilities. This area could remain a gym, become a private suite-style space, or support future finished expansion. The elliptical and weight system may convey if desired by the buyer. Outdoor living is another major highlight. The backyard features an oversized upper deck, a lower concrete patio beneath the deck, an oversized shed, and an irrigation/sprinkler system — all set against the peaceful backdrop of the wooded premium lot. The premium lot was a major upgrade when purchased, valued at approximately $20,000 by the sellers, and offers the privacy of having no homes directly behind you. Additional upgrades and features include ceiling fans throughout the home, tankless water heater, smart thermostat, security/monitoring system, garage door openers, wall-mounted TVs, storm doors/windows, multiple included appliances, additional refrigerator/freezer storage, and thoughtful improvements throughout. This is more than just a home — it is a complete lifestyle property offering premium lot value, flexible living space, multi-generational potential, a gourmet kitchen, luxury primary suite, finished entertainment areas, upgraded outdoor living, and privacy that many competing homes simply do not offer.

362 Neverland Dr, Middletown

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$689,900
4 Beds ⋅ 3 Baths
Discover elegance in this move-in ready home. This 4-bedroom, 3-bathroom home with a main-level primary bedroom en-suite is located in one of the most desirable communities, celebrated for its tranquil surroundings and resort-style amenities. Enter through a grand foyer into an expansive, elegant floor plan with soaring ceilings and designer lighting that create an atmosphere of timeless style. A true centerpiece of the home is the open eat-in gourmet kitchen—a chef's dream featuring white cabinetry with under-cabinet lighting, granite countertops, stainless steel appliances, a cooktop, double ovens, a large center island with countertop seating, and a spacious pantry—all flowing effortlessly into the living room with a cozy gas fireplace, abundant natural light, and vaulted ceiling. The living room offers an ideal space for hosting parties and celebrations. The main-level primary bedroom suite offers a peaceful retreat, complete with dual closets, a custom ceiling, and a spa-inspired custom tiled glass-enclosed shower, and double vanities. Two additional bedrooms and a full bathroom complete the main level. Upstairs, you will find an open loft-style family room, along with a fourth bedroom and a third full bathroom. If you need additional space, the expansive basement offers endless possibilities to create your own home theater, fitness room, game room, or even add a fifth bedroom. For those who love the outdoors, enjoy barbecues with family and friends in your spacious backyard featuring a custom-designed patio and built-in fire pit for roasting marshmallows. Or simply relax on the covered front porch with your morning coffee. Additional highlights include a main-floor laundry room, custom blinds throughout, dual thermostat for heating and air conditioning, a two-car garage, and a location within walking distance of the clubhouse. Enjoy the ease of low-maintenance living in this resort-style community, where the affordable monthly HOA fee covers lawn care, landscaping, snow removal, and trash service. Residents have access to an outstanding collection of amenities, including a heated outdoor swimming pool, pickleball, tennis, and bocce courts, as well as scenic walking trails. The impressive clubhouse serves as the heart of the community, offering a spacious gathering room, bar, fitness center, exercise studio, billiards room, meeting room, and a beautiful outdoor patio overlooking a tranquil pond with a fire pit. A vibrant social calendar featuring clubs, events, and activities makes it easy to stay active, meet neighbors, and enjoy the lifestyle you've been looking for. Conveniently located with easy access to the brand-new Bayberry Town Center, you'll enjoy nearby shopping, restaurants, fitness centers, and healthcare facilities. Schedule your private showing today and experience everything this exceptional home has to offer before someone else calls it home!

4200 Crosby Ln, Middletown

Listing courtesy of Walker Realty Group. Contact: (302) 373-4884
$569,900
3 Beds ⋅ 3 Baths
Welcome to 529 Contemplation Way, an exceptional home located in the highly sought-after Whispering Woods 55+ active adult community in Middletown, Delaware, where luxury, convenience, and a carefree lifestyle come together. Designed for buyers seeking the ease of first-floor living without sacrificing space, this beautifully maintained home offers the perfect blend of elegance, flexibility, and low-maintenance living. Outstanding curb appeal, a welcoming covered front porch, and manicured landscaping create an inviting first impression, while the dramatic two-story foyer and rich hardwood flooring throughout most of the main level immediately showcase the home's quality craftsmanship. The open-concept floor plan is filled with abundant natural light and soaring vaulted ceilings, creating a bright, spacious atmosphere ideal for everyday living and entertaining. The expansive family room flows seamlessly into the dining area before opening to the screened porch and oversized stamped concrete patio, providing exceptional indoor-outdoor living for morning coffee, relaxing evenings, or entertaining family and friends. The beautifully appointed kitchen is the centerpiece of the home, featuring stainless steel appliances, designer countertops, a stylish tile backsplash, abundant cabinetry, hardwood flooring, an undermount sink with a gooseneck faucet, and a large center island with seating and additional storage. Just beyond, the sun-filled breakfast area with its vaulted ceiling offers the perfect place to begin each day. The spacious main-level primary suite provides the comfort today's buyers desire with a tray ceiling, generous closet space, and a private bath featuring a double vanity and walk-in shower. A dedicated first-floor office offers flexibility for working from home, hobbies, crafts, or a quiet reading room, while the convenient first-floor laundry room and powder room complete the thoughtfully designed main level. Upstairs, you'll discover three additional spacious rooms along with an open loft overlooking the main living area, creating the perfect second family room, media room, game room, or private retreat for overnight guests and visiting family. Whether you're hosting holidays or simply need additional living space, this versatile layout adapts beautifully to your lifestyle. The expansive unfinished basement provides exceptional storage and endless possibilities for future finished living space, including a recreation room, fitness studio, workshop, hobby room, or home theater. Beyond the home itself, Whispering Woods offers one of Middletown's premier active adult lifestyles, featuring a beautifully appointed clubhouse, fitness center, outdoor swimming pool, gathering spaces, and an active social calendar filled with clubs, activities, and community events. Lawn care and snow removal are included, allowing homeowners more time to travel, relax, and enjoy everything the community has to offer. Ideally located just minutes from Historic Downtown Middletown, residents enjoy convenient access to outstanding restaurants, boutique shopping, coffee shops, grocery stores, healthcare, parks, walking trails, golf courses, and major commuter routes including Route 1, while remaining within easy reach of Delaware's beaches, Wilmington, and Philadelphia. Combining timeless architecture, an open and flexible floor plan, abundant natural light, outstanding indoor and outdoor living spaces, resort-style community amenities, and the convenience of move-in-ready first-floor living, 529 Contemplation Way presents a rare opportunity to enjoy the lifestyle you've been waiting for in one of Middletown's most desirable 55+ communities.

529 Contemplation Way, Middletown

Listing courtesy of BHHS Fox & Roach - Hockessin. Contact: (302) 999-9999
$799,000
4 Beds ⋅ 4 Baths
Welcome to the charming community of Parkside, nestled amidst the scenic beauty of Middletown, DE. This generously proportioned colonial home welcomes you with newly stained hardwood flooring that exudes warmth and coziness the moment you step in. The main floor boasts a well-planned layout perfect for entertainment, with its kitchen overlooking both the family room and sunroom. The kitchen comes installed with a practical island cooking amenity and a modern hooded vent, enhancing cooking experiences. An adjoining living room and dining room complement the open floor plan, making family gatherings a joyful experience. This residence offers four spacious bedrooms, with the primary bedroom being it's tour de force. It is equipped with a dedicated sitting area, a luxurious soaking tub, and a commodious walk-in closet, every feature designed with relaxation and comfort in mind. Other notable features include a versatile basement, offering ample additional living space. You'll find a cozy theatre room complete with a warm fireplace, and a walkout access to a serene and private backyard that blends seamlessly with the tree line for added solitude. Living in Parkside gives you access to numerous community amenities. From numerous pocket parks adorned with the natural bounty to an expanded swimming pool bookended by a spacious deck, there's something for everyone. Little ones can enjoy at the sizable tot lot while the fitness enthusiasts can sweat it out at the fully equipped fitness room. For your parties or meetings, the clubhouse is accessible and sure to add charm to your events. Experience the harmonious blend of comfort, luxury, and nature only at Parkside. This home promises an exemplary living experience tailored just for you.

434 Spring Hollow Dr, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100
$185,000
4 Beds ⋅ 1 Baths
Step back in time with this charming Victorian-style single-family home full of character and endless potential. Offering 4 bedrooms and 1 full bath, this classic residence is ready for its next owner make it their own. A welcoming wraparound front porch provides the perfect place to relax and enjoy the neighborhood before stepping inside. The main level features a living room, formal dining room, and kitchen, all highlighted by the home's impressive high ceilings and historic charm. Upstairs, you'll find four bedrooms and a full bathroom. Built with solid bones and a durable brick exterior, this home offers an excellent foundation for renovation while preserving its original character. Whether you're an investor, renovator, or buyer looking for a rewarding restoration project, this property is a rare opportunity to own a home with classic charm and incredible potential. With a little TLC, this beautiful Victorian can truly shine once again.

207 N Catherine St, Middletown

Listing courtesy of Real Broker, LLC. Contact: 8554500442
$559,250
2 Beds ⋅ 3 Baths
*MOVE IN READY* Introducing the 3223 Rye Harbour Way, the Tuscany, a beautifully appointed home offering 1,778 square feet of thoughtfully designed living space, plus a finished basement with full bathroom for plenty of storage and extra living space. This elegant residence blends open-concept living with private retreats, perfect for both everyday comfort and entertaining. The main level features a spacious family room anchored by a cozy gas fireplace, flowing seamlessly into the dining area and gourmet kitchen complete with upgraded quartz countertops, stylish backsplash, premium cabinetry, and stainless-steel appliances. A dedicated home office provides the ideal space for remote work or quiet study. The luxurious owner’s suite offers a spa-like bath and his and her closets, while a secondary bedroom and full bath add flexibility for guests or family. Expanding the living space, the home includes a stunning sunroom extension with ample windows and a high ceiling that fills the interior with natural light and opens to a composite deck, perfect for relaxing or entertaining outdoors. Additional highlights include a 2-car garage, convenient first-floor laundry, upgraded flooring throughout - all in a beautifully crafted home designed to fit your lifestyle. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you. To top it off, this community offers a stunning 5,400 square foot clubhouse, pickleball courts, tennis courts, bocce, a swimming pool, fitness center, and so much more! Relax and enjoy the peace of mind that your lawncare, snow removal, and trash/recycle are all taken care of for you. *Prices, dimensions, and features may vary and are subject to change. Photos are for illustrative purposes only and are of model home. See sales team for final options included. Taxes to be assessed after settlement. If using a Realtor: the agent's client must acknowledge on their first interaction with Lennar that they are being represented by a Realtor, and the Realtor must accompany their client on their first visit. For appointments and open houses, please visit the welcome home center located at 2405 Greyfriar Loop.*

3223 Rye Harbour Way, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339
$735,250
5 Beds ⋅ 5 Baths
Welcome to 6023 Freestone Boulevard at Freestone Village, where luxury, space, and thoughtful design come together in one exceptional home. This beautifully upgraded Danbury floorplan offers over 3,800 square feet of living space plus a partially finished basement with its own full bath, making it ideal for growing families, entertaining, or multigenerational living. The open-concept main level is designed for everyday living and hosting alike, featuring a gourmet kitchen, quartz countertops, soft close cabinetry, a spacious island, and a morning room extension that fills the home with natural light. The adjoining great room showcases a cozy fireplace, while a convenient first-floor guest suite with a full bath offers the perfect space for overnight guests or extended family. Upstairs, the luxurious owner's suite provides a relaxing retreat with a tray ceiling, spa-inspired bath with soaking tub, and an oversized walk-in closet. Three additional bedrooms, including a secondary bedroom with its own private en-suite bath, plus a centrally located laundry room completes the second floor. The finished basement adds even more flexible living space with a large recreation room and a full bathroom—perfect for a home theater, fitness area, game room, or additional guest accommodations. Additional premium features include oak stairs with open railing, designer tile selections, stainless-steel appliances including refrigerator, washer, and dryer, and a prime location in the award-winning Appoquinimink School District with easy access to shopping, dining, and major commuter routes. *Pictures are of model home from a sister community and for representational purposes only. There is a sales trailer on-site. Please see New Home Consultant for details. Taxes to be assessed after settlement. Realtor representation must be acknowledged on the first interaction with Lennar, and the agent must accompany their client on the first visit.

6023 Freestone Blvd, Middletown

Listing courtesy of Atlantic Five Realty. Contact: 8564243339
$499,000
4 Beds ⋅ 2 Baths
Welcome to this charming 4-bedroom, 2-bathroom home ideally situated on Main Street in the heart of Middletown, offering the perfect blend of character, comfort, and convenience. Step inside to beautiful hardwood floors that flow throughout the main level, creating a warm and inviting atmosphere. The formal living room features a cozy wood-burning fireplace, making it the perfect place to gather on chilly winter evenings. Just beyond, the formal dining room provides an elegant setting for holiday celebrations, dinner parties, and everyday meals. The updated kitchen is designed with both style and functionality in mind, featuring a spacious island perfect for entertaining, ample cabinet storage, and a bright breakfast area where you can enjoy your morning coffee while overlooking the expansive backyard. The main level offers two comfortable bedrooms and a full bathroom, providing flexible living options for guests, family, or a home office. The finished lower level includes two additional generously sized bedrooms, a second full bathroom, and a spacious laundry room with abundant storage. Outdoor living is just as inviting, with a large deck that's perfect for summer barbecues, outdoor dining, and relaxing evenings. The one-car garage offers additional storage, while the oversized backyard provides endless possibilities with plenty of room for play, gardening, pets, or future outdoor entertaining spaces. Located just moments from Middletown's charming shops, restaurants, parks, and top-rated schools, this home offers small-town living with all the conveniences you need. Don't miss your opportunity to make this beautiful Main Street home your own.

708 E Main St, Middletown

Listing courtesy of Keller Williams Realty Centre. Contact:

$529,000
4 Beds ⋅ 3 Baths
Welcome to 354 Northhampton Way in the desirable Willow Grove Mill community of Middletown! This beautifully maintained 4-bedroom, 2.5-bath home offers spacious living, thoughtful updates, and a layout designed for today's lifestyle. Step inside to find fresh, neutral paint throughout, creating a bright and inviting atmosphere that's truly move-in ready. The recently refreshed kitchen features updated finishes, ample cabinetry, generous counter space, and an open layout that flows seamlessly into the family room, making it perfect for both everyday living and entertaining. Sliding glass doors lead to a low-maintenance deck overlooking the fully fenced backyard—ideal for relaxing, grilling, or hosting family and friends. Upstairs, the spacious primary suite offers a private retreat with dual walk-in closets and an en-suite bath featuring dual vanities, a soaking tub, and a separate shower. Three additional generously sized bedrooms, a full hall bath, and a convenient second-floor laundry room complete the upper level. The finished basement provides flexible space for a recreation room, home gym, office, or playroom. A two-car garage, generous storage, and a prime location in the Appoquinimink School District add to the home's appeal. Conveniently located near Route 1, shopping, dining, parks, and all that Middletown has to offer, this home combines comfort, style, and convenience. With a refreshed kitchen, fresh interior paint, and plenty of room to grow, 354 Northhampton Way is ready for its next owners. Schedule your private tour today!

354 Northhampton Way, Middletown

Listing courtesy of EXP Realty, LLC. Contact: 8885434829
$565,000
4 Beds ⋅ 3 Baths
Price Improvement and $10,000 Seller Assistance! Seller is offering $10,000 toward buyer's closing cost or interest rate buy-down with an acceptable offer. Welcome to 1723 West Matisse Drive! Located in the highly sought-after community of the Village of Bayberry North, this beautifully maintained 2018-built, four-bedroom, 2.5-bath Colonial offers a fenced backyard with a deck, a finished basement, and fully paid-off solar panels—all within the award-winning Appoquinimink School District. Overlooking one of Bayberry's beautifully maintained pocket parks, the home's charming Colonial elevation is illuminated by the morning sun, creating the perfect setting to enjoy from the covered front porch. Inside, the central foyer welcomes you to a traditional floor plan featuring a formal dining room to the right and a versatile office or living room to the left, while a private hallway leads to a secluded powder room. The open-concept kitchen is equipped with stainless steel appliances and flows seamlessly into the breakfast nook and spacious great room, making it ideal for everyday living and entertaining. The attached two-car garage features a single oversized bay door for added convenience. Upstairs, the primary suite includes an upgraded en-suite bathroom, accompanied by a convenient second-floor laundry room and three additional bedrooms that share a full hall bathroom. The builder-finished basement recreation room provides valuable additional living space perfect for a media room, playroom, home gym, or hobbies. Residents of Bayberry North enjoy miles of paved walking trails, three playgrounds, dozens of pocket parks and open green spaces, and access to the Lakehouse, which is available to rent for private events and offers opportunities for kayaking and fishing. The growing Bayberry Town Center already provides convenient shopping, banking, and fuel, with additional amenities planned for the future. Due to an unexpected overseas relocation, the sellers have competitively priced this home for a quick sale and are offering it in as-is condition, presenting an exceptional opportunity to own in one of the area's most desirable communities.

1723 W Matisse Dr, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 3022341888
$499,900
4 Beds ⋅ 3 Baths
*One or more photos in this listing have been virtually staged using AI* Completely Renovated & Move-In Ready! Welcome to this beautifully updated ranch-style home situated on a picturesque 2-acre lot in the heart of Middletown Valley. Every detail has been thoughtfully renovated, offering a bright, modern interior with quality finishes throughout. The open and inviting floor plan is perfect for everyday living and entertaining. Step outside to enjoy the spacious backyard, offering endless possibilities for outdoor gatherings, recreation, gardening, or simply relaxing while taking in the peaceful surroundings. Enjoy the tranquility of country living while remaining just minutes from downtown Middletown, Frederick, shopping, dining, schools, parks, and major commuter routes. Whether you're looking for your forever home or a quiet retreat with modern comforts, this exceptional property is ready for its new owner. Don't miss this rare opportunity!

9001 Hollow Rd, Middletown

Listing courtesy of RE/MAX Realty Centre, Inc.. Contact:

$628,565
4 Beds ⋅ 4 Baths
Discover the Bennett Farmhouse, a quick-delivery home in the highly sought-after Meadows community. This is the last home in our coveted Jazz series. Situated on a spacious 0.34-acre homesite, this beautifully designed residence offers more than 2,700 square feet of thoughtfully planned living space that perfectly blends casual luxury with everyday functionality. In addition, this home sits next to a 70-acre park with a community Lakehouse, kids playground, dog park, and miles of walking trails. The main level is enhanced by a bright and inviting sunroom, providing additional living space ideal for relaxing or entertaining. Luxury vinyl plank flooring extends throughout the entire first floor, creating a seamless and sophisticated look. The kitchen is a chef's dream, featuring a gas cooktop, double wall oven, a vented micro-hood, elegant quartz countertops, and ample workspace for cooking and gathering. The finished basement expands your living options with a spacious recreation room and a full bathroom, making it perfect for a media room, game room, or home gym. Upstairs, the luxurious primary suite offers an estate-like experience with a generously sized bedroom, two large walk-in closets, and an oversized spa-inspired bathroom. The spacious secondary bedrooms provide comfortable accommodations for family or guests, while the conveniently located second-floor laundry room makes everyday living even easier. With exceptional craftsmanship, modern finishes, and a functional layout designed for today's lifestyle, this Bennett Farmhouse offers the perfect combination of comfort, style, and convenience in one of the area's most desirable communities.

5601 S Bayberry Pkwy, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact: 3022540100
$849,000
4 Beds ⋅ 5 Baths
Coming soon ! Welcome to 5 Dean Lane, a stunning 4-bedroom, 4.5-bath home in the sought-after Middletown Glen community. Ideally located within walking distance of schools, parks, and the library, this exceptional home is also just minutes from the nature center, local restaurants, golf courses, and major commuter routes. Step inside to a welcoming foyer featuring a private home office, then continue past the elegant formal dining room into the spacious living room that seamlessly opens to the bright, eat-in kitchen—perfect for everyday living and entertaining. Entering through the attached 2-car garage, you'll appreciate the thoughtfully designed mudroom with built-in storage, along with an oversized pantry and convenient powder room on the main level. Upstairs offers an ideal layout with an additional loft-style lounge that provides flexible living space. The luxurious primary suite occupies its own private wing and features a sitting area, two walk-in closets, and a spa-like ensuite bath. Two additional bedrooms share a full hall bath, while the opposite wing includes a fourth bedroom with its own ensuite bath and a conveniently located laundry room. The finished walkout basement is an entertainer's dream, featuring a large recreation area, wet bar, full bathroom, and ample storage space. Outside, the beautifully hardscaped backyard offers a low-maintenance setting that's perfect for relaxing or hosting gatherings. Meticulously maintained and truly move-in ready, this thoughtfully upgraded home combines generous living spaces, quality finishes, and an unbeatable location. 5 Dean Lane has everything you've been looking for.

5 Dean Ln, Middletown

Listing courtesy of Real Estate Innovations. Contact:

$949,999
5 Beds ⋅ 6 Baths
PRICED BELOW APPRAISED VALUE!! Nestled on an expansive 6.84-acre lot just minutes from shopping, dining, and commuter routes, this stunning colonial exudes elegance and comfort. Built in 2013, the home features a harmonious blend of vinyl siding and stone, creating a timeless façade that invites you in. Step inside to discover five spacious bedrooms and six bathrooms. The heart of the home boasts a cozy fireplace, perfect for intimate gatherings or quiet evenings. With the primary suite on the main level along with your laundry, the home proves to be extremely functional on all levels. A fully finished basement offers endless possibilities for entertainment or relaxation, with both interior access and an outside entrance for convenience. Grab a seat at the bar, pick your spot on the couch to watch TV, work out, or play games in the game room. Enjoy the serenity of your private retreat, complete with an attached side-entry garage and ample driveway space. This property is not just a home; it's a lifestyle, offering the perfect balance of sophistication and warmth. Experience the tranquility and exclusivity that this remarkable residence has to offer, where every detail has been crafted for your comfort and enjoyment.

228 Mercys Dr, Middletown

Listing courtesy of Keller Williams Realty. Contact: 7036690099
$610,000
4 Beds ⋅ 3 Baths
Nestled in the award winning Appoquinimink School District in Middletown, DE, 331 Plato Place is a charming, Traditional style home boasting 4 spacious bedrooms and 2 and a half bathrooms. Located on a premium lot in the desirable Village of Bayberry community, the home overlooks protected land conservation with beautiful walking paths and a community park. Step inside to discover a radiant open floor plan bathed in natural light. Beautiful bamboo floors span the main level while the living area is enhanced with soaring 10ft ceilings. The heart of the home, the kitchen, features a large island, pantry, an eat-in area, and stainless steel appliances which make for a warm yet functional space, perfect for family gatherings. The living area flows seamlessly onto the rear deck and stamped concrete patio, presenting a perfect setting for your morning coffee or al fresco dining. A fully fenced backyard also provides added privacy and safety. Ascend the stairs to the primary suite featuring a walk-in closet, an additional secondary closet, and an ensuite bathroom. Three more generously-sized bedrooms and another full bathroom round out the second story, ensuring ample living spaces for all. Not to be overlooked, the partially finished basement includes a pool table, an additional room with an egress, utility area, and an abundance of storage space. The future potential of an additional bathroom in the basement thanks to its rough-ins enhance the possibilities this home offers. Rounding out this stunning home is a convenient, 2 car attached garage that provides direct access to a mudroom off the kitchen. Featuring central A/C and a heating system with forced air, and the roof replaced in 2025, this home offers modern comforts and a welcoming charm. Ideal for those seeking to live in a vibrant community, 331 Plato Place is the dream home you've been searching for.

331 Plato Pl, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100
$634,900
3 Beds ⋅ 3 Baths
Privacy, space, and convenience come together in this all-brick ranch on just over 7 acres with no HOA; land is on both sides of the driveway. All brick and offering more than 2,700 sq. ft. on the main level, this home is ready for you. The property features 3 spacious bedrooms, 2.5 baths, a living room with a brick fireplace and wood stove insert, a family room, and a large mudroom off the kitchen. The unfinished walk-out basement offers excellent potential for additional living space, storage, or a workshop. Major updates include a roof replaced in 2020, dual HVAC zones with units replaced in 2010 and 2015, septic tank pumped in fall 2025, and an new rear deck. Enjoy plenty of room for indoor and outdoor living, all while being close to everything. Please note: property has a shared driveway with deeded right of way.

298 Mcdaniel Ln, Middletown

Listing courtesy of Colony Realty. Contact:

$621,619
2 Beds ⋅ 2 Baths

2817 Bernstein Cir, Middletown

Listing courtesy of Blenheim Marketing LLC. Contact: 3022540100
$765,000
5 Beds ⋅ 3 Baths
​ Huge price reduction!! Seller is ready to move. Welcome to 117 Sassafras Drive, located in Matapeake one of Middletown’s most sought after neighborhoods! This move in ready 5-bedroom, 2.5 bath home offers the perfect blend of space, comfort, and location. Step inside to find a thoughtfully designed floor plan featuring a first-floor bedroom that could also serve as a private home office, a lovely formal living room and dining room, and a spacious eat in kitchen with plenty of room to gather. The kitchen opens into a bright and inviting sunroom overlooking the expansive backyard, creating the perfect space for entertaining or simply enjoying your morning coffee. Upstairs, you’ll find generously sized bedrooms, while the large basement offers endless possibilities for additional living space, a home gym, recreation room, or extra storage. Situated on a spacious lot in a beautifully maintained neighborhood known for its larger homesites, this home is conveniently located just behind Appoquinimink High School and just minutes from shopping, dining, parks, and everything Middletown has to offer. Move in ready, beautifully maintained, and waiting for its next owners. Don’t miss your opportunity to make this exceptional home yours. Schedule your private tour today!

117 Sassafras Dr, Middletown

Listing courtesy of Tesla Realty Group, LLC. Contact: 8448375274
$669,900
3 Beds ⋅ 2 Baths
Welcome to 216 Baldy Lane– A Stunning Ranch-Style Home in the Premier 55+ Community of Traditions at Whitehall. Step into luxury and comfort in this beautifully upgraded 3-bedroom, 2-bath ranch-style home that truly shows like a model. Thoughtfully designed and impeccably maintained, this residence offers exceptional one-level living with high-end finishes throughout. Start your day on the inviting covered front porch, the perfect spot for morning coffee or evening relaxation. Inside, you're greeted by an expansive open floor plan featuring luxury vinyl plank flooring that flows seamlessly through the foyer, great room, dining area, and hallways. The great room impresses with two-story vaulted ceilings, a floating gas fireplace, custom blinds, and a remote-controlled power shade on the upper window for added convenience. The gourmet kitchen is a true showstopper—featuring white quartz countertops, a peninsula with raised bar seating, stainless steel appliances, a five-burner gas range, light gray cabinetry, tile backsplash, and both recessed and pendant lighting. Enjoy an expanded owner's suite complete with a cozy sitting area, plush carpeting, a ceiling fan, recessed lighting, and sliding doors to a private deck. The suite also features a large walk-in closet and a spa-inspired en-suite bath with granite countertops and a custom, low step-in shower. Two generously sized guest bedrooms and a large laundry room offer functionality and comfort. Upstairs, a lofted bonus room provides the ideal space for a home office, game room, or additional entertaining area. The full walk-out basement boasts 8-foot ceilings, a sliding glass door, multiple windows for natural light, and a bathroom rough-in—offering endless potential for customization, whether for extra living space, hobbies, or storage. As a resident of Traditions at Whitehall, you'll enjoy a vibrant lifestyle with a clubhouse, community pool, and new pickleball courts. HOA fees cover lawn care, landscaping, snow removal, and more—giving you more time to enjoy life. Don’t miss this incredible opportunity to own a turnkey home in one of Delaware’s most sought-after active adult communities. Schedule your private tour today!

216 Baldy Ln, Middletown

Listing courtesy of Patterson-Schwartz-Hockessin. Contact: 3022393000
$599,000
3 Beds ⋅ 3 Baths
Welcome to your own private retreat! This 3-bedroom, 3 full bath home offers nearly 2,500 square feet of finished living space and comes with not one, but two parcels totaling approximately 7.63 acres. The home is situated on 5.90 acres and includes an additional 1.73-acre wooded lot located directly behind the property, providing even more privacy and future possibilities. Inside, you'll find beautiful wood flooring throughout the main level and a spacious layout designed for comfortable living. The primary suite features its own private full bath and direct access to a deck overlooking the peaceful surroundings. Two additional bedrooms and a full bath complete the main level. Enjoy the outdoors from the wraparound rear porch or entertain guests on the expansive two-tier deck. During the colder months, cozy up beside one of the home's two wood-burning fireplaces. The lower level offers additional living space along with a third full bath, making it ideal for a recreation room, guest area, or home office. With plenty of driveway parking and a 2-car attached garage, there is ample room for vehicles, equipment, and guests. Conveniently located just minutes from downtown Middletown and within the highly sought-after Middletown School District, this property offers the perfect combination of privacy, acreage, and accessibility.

2748 Bennies Hill Rd, Middletown

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$625,000
5 Beds ⋅ 2 Baths
This charming Cape Cod home, nestled in Lower Dauphin School District, offers a perfect blend of comfort and functionality. With five bedrooms and two full bathrooms, this residence is designed for both relaxation and entertaining. The heart of the home features an inviting eat-in kitchen, seamlessly connecting to a cozy family room, ideal for gatherings. The traditional floor plan enhances the flow, making it easy to enjoy everyday living. Major renovations in 2018 and more recent updates have revitalized this home, ensuring it meets modern standards while retaining its classic charm. The exterior boasts durable vinyl siding and a welcoming deck, perfect for enjoying a morning coffee or watching the evening sunset. The expansive 5.59-acre lot offers a unique blend of partly wooded areas with a creek and open space for pastures and gardening, providing ample opportunities for outdoor activities. Additional features include a full basement with outside entrance, offering endless possibilities for customization. The property is complemented by ample parking and an oversized Morton building, with space for ten or more vehicles, a barn/stable with six horse stalls, and a versatile office/studio workshop. Located in a rural setting, this home is just a short drive to Harrisburg, Hershey, and Lancaster, making it conveniently close to everyday necessities. Experience the warmth and charm of this delightful property, where lasting memories are waiting to be made.

3740 Beagle Rd, Middletown

Listing courtesy of Coldwell Banker Realty. Contact: 7175342442
$1,475,000
5 Beds ⋅ 5 Baths
Looking for new construction, but don't want to wait? This gorgeous 2025 built Craftsman is the perfect option! Like new, only better thanks to an investment of all the things that are a hassle to add to a new home - rear yard fence, plantation shutters and luxury shades, water softener/treatment system, an Amish garden shed and more! Move in now and do nothing but pack your personal belongings! Amazing opportunity in quiet Middletown but just minutes to all of the area's conveniences. Relax and escape to your own private retreat, enjoy sunsets on your covered back porch and find plenty of room to stretch out and play - over 5000 square feet of perfectly curated living space. Dedicated home office, formal dining and gourmet open kitchen with oversized island and eat-in breakfast area. Family room with soaring ceilings and a cozy fireplace - truly the perfect setting with floor to ceiling windows that floods the space with natural light. Smart open layout with primary bedroom suite on main level, complete with massive double-sided walk-in closet, dual vanity spaces, a soaking tub and oversized walk-in shower. Upstairs there are three generously sized secondary bedrooms, one with a private en suite bath and walk-in closet and a second hall bath. Gorgeous cat walk hallway overlooks the family room. On the lower level you have a secondary living level with yet another full bedroom and en suite bath, perfect for a guest suite. Tons of conditioned storage space finishes off the walk-out lower level. Enjoy the outdoors from your covered patio off the eat-in breakfast area/morning room and play down below in the spacious split-rail fenced rear yard. New Amish storage shed has space for all of the lawn equipment. Plenty of room for the furry family members or even a chicken run! Attached two car garage and expanded driveway has plenty of space for guest parking as well. While the peaceful setting can make you feel like you're a world away, this home is just two miles to the heart of downtown Middletown and less than 30 minutes to Downtown Frederick. Tons of great area shopping and dining, but the small town feel you've been yearning for. Don't miss out on this incredible opportunity!

2802 Bidle Rd, Middletown

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$509,900
2 Beds ⋅ 2 Baths
Welcome to 1502 Arrowood Court! Nestled within the desirable 55+ community of Four Seasons At Silver Maple, this home sits peacefully on a cul de sac, boasting impeccable curb appeal with its inviting front porch and thoughtfully-designed landscaping. As you enter through the glass storm door, feel the flood of natural light brighten up the neat foyer. To your right is a comfortable size bedroom complete with its own full bathroom. To your left, convenience is offered via a laundry room neatly tucked off the 2-car garage. At the heart of the home is a large study with glass doors that yield captivating views of the well-equipped kitchen featuring a double oven, gas burners, and roomy island. Not to neglect the inclusion of a brand new microwave and all stainless steel appliances- this kitchen leaves nothing to be desired. Its open layout design incorporates a spacious dining area, perfect for gatherings. Retire to the sun-drenched sun room which hosts tons of natural light that paints an image of cozy afternoons spent with a good book. The family room is commodious with a gas fireplace and generous window placements allowing for abundant natural light and plenty of rooms for family gatherings. The primary suite is a sanctuary, hosting 2 large closets and two separate sinks alongside a sizeable shower. Also noteworthy is the unfinished basement- a canvas, if you will- featuring high ceilings and painted floors just waiting to be transformed into your dream space. Finally, the home's exteriors don't disappoint either. Situated next to an open space on a cul de sac, the property allows for serene perspectives of the community amenities and nearby clubhouse. Yes, there's a newer roof too! Call to make an appointment and experience this beautiful, versatile home today!

1502 Arrowood Ct, Middletown

Listing courtesy of Patterson-Schwartz-Middletown. Contact: 3022855100