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Middletown, DE Homes for Sale

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  • /78

    $665,000

    • 4 Beds
    • 3.5 Baths
    • 3,950 Sq Ft

    629 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 629 Spring Hollow Dr, where every inch is dripping with beauty and elegance. In one of Middletown's most sought after communities of Parkside, 629 Spring Hollow Dr is situated on a corner lot with beautiful views, endearing front porch, board and batten siding, stone skirting, and gorgeous landscaping - the curb appeal leaves nothing to be desired. Professionally designed from top to

    Megan Aitken Keller Williams Realty

    629 Spring Hollow Dr, Middletown, DE 19709
  • /47

    $665,000

    • 4 Beds
    • 3 Baths
    • 3,025 Sq Ft

    734 Wood Duck Ct, Middletown, DE 19709

    Welcome to 734 Wood Duck Ct – A Stunning Blend of Comfort and Style in Middletown!Nestled on a quiet cul-de-sac in one of Middletown’s most desirable neighborhoods, this beautifully maintained 4-bedroom, 3-full-bath home is the perfect combination of space, function, and modern updates. Step inside to find an inviting layout featuring a dedicated home office, ideal for remote work or

    Cristina TLASECA Madison Real Estate Inc. DBA MRE Residential Inc.

    734 Wood Duck Ct, Middletown, DE 19709
  • /44

    $435,000

    • 3 Beds
    • 3 Baths
    • 2,300 Sq Ft

    2 N Cummings Dr, Middletown, DE 19709

    This is the one! Brand new flooring everywhere...fresh and inviting! Talk about location. Minutes from downtown Middletown and Route 1. Spacious? Endless square footage with a finished basement that has a few storage areas. The main floor features a glass enclosed eating area and large inviting great room. The 2nd floor has all 3 bedrooms and a nicely sized landing area for a desk or

    Audrey Brodie First Class Properties

    2 N Cummings Dr, Middletown, DE 19709
  • /59

    $438,000

    • 2 Beds
    • 2.5 Baths
    • 2,025 Sq Ft

    5910 Ravel Ln, Middletown, DE 19709

    55+ Community. Enter a bright, open floor plan with gleaming hardwood floors. Entertain friends and family in your gourmet kitchen complete with stainless steel appliances, granite countertops, flat top range, double oven and oversized island. First floor laundry and master bedroom, with a full bathroom, offers much convenience. The main floor also has a powder room, storage closet and garage

    Margaret Poisson Century 21 Gold Key-Dover

    5910 Ravel Ln, Middletown, DE 19709
  • /28

    $650,000

    • 4 Beds
    • 2.5 Baths
    • 3,175 Sq Ft

    120 Betsy Rawls Dr, Middletown, DE 19709

    Welcome to this exquisite 4-bedroom, 2.5-bath home on the 18th hole of the prestigious and highly sought-after community of The Legends. With breathtaking golf course views, a thoughtfully designed layout, and luxurious finishes, this home offers unmatched comfort and elegance. Step through the tall foyer into a warm, welcoming atmosphere. To the left, a formal dining room features crown molding;

    Delcollo & Salva Team Patterson-Schwartz-Hockessin

    120 Betsy Rawls Dr, Middletown, DE 19709
  • /54

    $634,000

    • 6 Beds
    • 5 Baths
    • 2,900 Sq Ft

    875 Port Penn Rd, Middletown, DE 19709

    Step into the past and own a piece of Delaware's history with the Dilworth House, one of the earliest homes built in the state by Olla Jansen, a Swedish colonist from the 1600-1700 Native American Period. Situated on 12.25 acres of pristine land that backs up to the Augustine Wildlife Preserve, this property is a rare find, offering both a home and a rich connection to the past. The Dilworth

    Kelly Clark Crown Homes Real Estate

    875 Port Penn Rd, Middletown, DE 19709
  • /46

    $649,900

    • 3 Beds
    • 3 Baths
    • 2,775 Sq Ft

    761 Honey Locust Rd, Middletown, DE 19709

    READY IMMEDIATELY! BACKS TO WOODS , WALK-OUT FINISHED BASEMENT! PREMIER LOT! Middletown's premier 55-plus community is ready for immediate move-in! This meticulously crafted home with a flexible floor plan offers 1,780 sq. ft. on the first floor, and an additional 995 sq. ft. in the basement. Enter the inviting open-concept floor plan, where luxury engineered wood flooring flows seamlessly

    Lori McKewen Active Adults Realty

    761 Honey Locust Rd, Middletown, DE 19709
  • /2

    $445,000

    • 3 Beds
    • 3.5 Baths
    • 3,342 Sq Ft

    1474 Flintshire Dr, Middletown, DE 19709

    ***RARE OPPORTUNITY – ASSUMABLE 3.625% MORTGAGE! ***Step into a home that’s better than new—perfectly poised and ready for you to make it your own. This stunning end-unit, corner lot property boasts a combination of luxury, style, and convenience that’s simply unmatched. No expense was spared in outfitting this home, with high-end finishes that elevate every room. Recessed lighting throughout

    Justin Campbell RE/MAX Associates - Newark

    1474 Flintshire Dr, Middletown, DE 19709
  • /10

    $624,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,349 Sq Ft

    1422 Pennfield Dr, Middletown, DE 19709

    Great room with soaring vaulted ceiling.Kitchen with central Soapstone Metro quartz island.Window-lined dining area with access to covered deck.Covered deck continues striking vaulted ceiling.Primary suite with ceiling treatment and sitting room.Primary bath with dual freestanding vanities.Home office with sliding doors off the foyer.

    Builder Photo

    K. Hovnanian Homes

    Builder

    1422 Pennfield Dr, Middletown, DE 19709
  • /24

    $649,900 New Construction

    • 3 Beds
    • 2 Baths
    • 2,121 Sq Ft

    1521 Lesterfield Way, Middletown, DE 19709

    Kitchen, dining area & great room flow under a vaulted ceiling.Fireplace creates a cozy focal point in the great room.Kitchen with stacked Stone Grey cabinets & glass-front uppers.Dining area opens to a screened deck for outdoor living.Primary suite features ceiling detail & window-lined sitting room.Private primary bath with dual sinks & spacious walk-in closet.Finished

    Builder Photo

    K. Hovnanian Homes

    Builder

    1521 Lesterfield Way, Middletown, DE 19709
  • /12

    $633,900 New Construction

    • 3 Beds
    • 3 Baths
    • 2,810 Sq Ft

    Kerr Plan at K. Hovnanian’s® Four Seasons at Pennfield, Middletown, DE 19709

    Included Extra Suite, ideal for multi-generational living and long-term guests.Private home office off of foyer, to work from home with plenty of space.Spacious great room with slider to covered patio.Stylish kitchen with island and large pantry.Luxurious primary suite with triple windows.Relaxing primary bath with split vanities and walk-in closet.Convenient 3-car tandem

    Builder Photo

    K. Hovnanian Homes

    Builder

    1415 Pennfield Dr Unit 36483660, Middletown, DE 19709
  • /11

    $142,000

    • 3 Beds
    • 2 Baths
    • 1,493 Sq Ft

    300 Hostetter Blvd, Middletown, DE 19709

    Brand New - 2024 Eagle River Model - Stunning, spacious, brand new 28 x 56 doublewide 3/2 home with living room, separate family room, beautiful open kitchen, & dining room. This home is immaculate with all modern upgrades, large bedrooms, walk in closet in primary, recessed lighting, vinyl & soft carpet flooring. Complete appliance package includes dishwasher, stove/oven, refrigerator, microwave

    Ryan Gehris USRealty.com LLP

    300 Hostetter Blvd, Middletown, DE 19709
  • /37

    $549,900

    • 4 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    400 Reading Ln, Middletown, DE 19709

    This beautiful 4 Bedroom, 2 Bath home with a full unfinished basement to finish to your taste. is perfectly situated on a spacious corner lot in the highly sought-after Misty Vale Farm community. Offering the ideal balance of country charm and modern convenience , its just minutes from major businesses, shopping, schools and hospitals. Step inside to a welcoming two-story foyer that leads to

    Carole Kisner Keller Williams Realty Central-Delaware

    400 Reading Ln, Middletown, DE 19709
  • /33

    $359,999

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    1049 Wickersham Way, Middletown, DE 19709

    Welcome to 1049 Wickersham Way! As you step through the front door, you’re immediately greeted by a bright and inviting entryway. The first room you encounter is a flexible space—perfect for a home office, gym, or even a cozy reading nook. It’s a versatile area that adapts to your needs. What makes it even better is the door leading directly to the spacious backyard.As you continue upstairs,

    Khalilah Ling Crown Homes Real Estate

    1049 Wickersham Way, Middletown, DE 19709
  • /79

    $949,000

    • 4 Beds
    • 5 Baths
    • 4,700 Sq Ft

    851 Sweet Birch Dr, Middletown, DE 19709

    Welcome to this charming Schell Brothers Kingfisher model home located in the desirable community of Parkside located in Middletown, DE. This spacious home boasts 4 bedrooms and 3.2 bathrooms spread over 2 levels/stories. This lovely home has a first floor primary suite with stunning windows overlooking the fenced in yard. Step inside to find a beautifully designed interior featuring stunning

    Ann Marie Germano Patterson-Schwartz-Middletown

    851 Sweet Birch Dr, Middletown, DE 19709
  • /33

    $575,000

    • 2 Beds
    • 2 Baths
    • 1,825 Sq Ft

    4513 Cagney Ln, Middletown, DE 19709

    You will LOVE The Ponds at Bayberry, a premier 55+ community in Middletown! This spotless and lovingly cared for "Cooper" Model home is ready to move into with quick possession available! This 2/3 bedroom (study could easily be 3rd bedroom with doors added) is ready for your move in! As you enter the foyer, there is an open formal dining room to the left that overlooks a big family room with an

    David Iliff Patterson-Schwartz-Hockessin

    4513 Cagney Ln, Middletown, DE 19709
  • /46

    $469,900

    • 3 Beds
    • 2 Baths
    • 2,225 Sq Ft

    636 Poets Way, Middletown, DE 19709

    Welcome to this Coleridge model, located in the highly desirable Springmill community in Middletown, Delaware. Upon entry, you'll be greeted by elegant hardwood flooring that flows seamlessly through the Great Room, breakfast area, expansive kitchen, and formal Dining Room. The Great Room features a cozy fireplace and an open-concept layout perfect for modern living. This home offers a

    Vicky Miller Patterson-Schwartz-Middletown

    636 Poets Way, Middletown, DE 19709
  • /63

    $1,100,000

    • 5 Beds
    • 5.5 Baths
    • 4,425 Sq Ft

    757 Idlewyld Dr, Middletown, DE 19709

    Welcome to a residence where luxury meets comfort in perfect harmony.Originally a model home, this property showcases high-end upgrades and thoughtful details throughout. The gourmet kitchen is a chef’s dream, featuring sleek countertops, stainless steel appliances, and generous space for both casual dining and grand entertaining. Crown molding in the foyer and owner’s suite, paired

    Mike McGavisk Empower Real Estate, LLC

    757 Idlewyld Dr, Middletown, DE 19709
  • /17

    $595,000

    • 4 Beds
    • 2.5 Baths
    • 3,000 Sq Ft

    150 Gloucester Blvd, Middletown, DE 19709

    Welcome home to 150 Gloucester Blvd. A stunning colonial-style residence in Willow Grove Mill. Come and tour this well maintained home featuring 4 bedrooms and 2.5 bathrooms. Upon entering this 10,000.00 sq-ft home you will find a mixture of lovely hardwood and laminated floors throughout the home. The main level features a huge living room, formal dinning room, a half bathroom, a sizeable room

    Samuel Iwu Tesla Realty Group, LLC

    150 Gloucester Blvd, Middletown, DE 19709
  • /26

    $115,000

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft

    923 Holly Ct Unit A923, Middletown, DE 19709

    Beautifully Renovated Double-Wide Home!Step inside this stunningly updated double-wide and fall in love with the details! Featuring engineered wood flooring and actual drywall throughout (no paneling here), this home offers the quality and comfort you’ve been looking for. The heater and air conditioning system are just 3 years young, ensuring year-round efficiency.Enjoy cozy evenings

    Robyn Roberts BHHS Fox & Roach-Christiana

    923 Holly Ct Unit A923, Middletown, DE 19709
  • /18

    $1,100,000

    • Studio
    • 6,384 Sq Ft

    20 W Main St, Middletown, DE 19709

    Exceptional Mixed-Use Investment Opportunity in the Heart of Middletown! 22 W Main Street—a fully-leased, free-standing mixed-use building offering a rare opportunity in one of Middletown’s most active commercial corridors. This well-maintained property is ideally positioned on a vibrant stretch of West Main Street, surrounded by thriving businesses and within walking distance to shops, dining,

    Paul Pantano Pantano Real Estate Inc

    20 W Main St, Middletown, DE 19709
  • /35

    $575,000

    • 4 Beds
    • 2.5 Baths
    • 3,450 Sq Ft

    422 Georgiana Dr, Middletown, DE 19709

    Move-in ready and waiting for you! Welcome home to 422 Georgiana, a stunning 4-bedroom, 2.5-bath Thompson-built home in the highly sought-after Crossland at the Canal. This premier community offers low-maintenance living with a pool, recreation hall for private gatherings, and well-kept common areas. From the moment you step into the grand 2-story foyer, you’ll feel the warmth and care put into

    Heather Palmer Long & Foster Real Estate, Inc.

    422 Georgiana Dr, Middletown, DE 19709
  • /12

    $120,000

    • 3 Beds
    • 2 Baths
    • 1,386 Sq Ft

    601 Village Dr, Middletown, DE 19709

    2024 Skyline Model Manufactured Home. Beautiful 3/2 double wide home with modern updates. Open floor-plan, recessed lighting, vinyl flooring all throughout, full drywall in living areas, walk-in closets, ample storage, and 8 feet tall flat ceilings.. Stainless steel appliances in the kitchen, full size washer & dryer, large pantry with plenty of storage. Brand new home comes with manufacturer's

    Marilyn Green RE/MAX Associates-Wilmington

    601 Village Dr, Middletown, DE 19709
  • /36

    $493,700

    • 2 Beds
    • 2 Baths
    • 2,200 Sq Ft

    8 Spring Arbor Dr, Middletown, DE 19709

    Welcome to 8 Spring Arbor Dr., a beautifully maintained 2-bedroom, 2-bath ranch home with a flex room that could be used as a 3rd bedroom in the sought-after 55+ community of Spring Arbor. With 2,196 sq. ft. of stylish, one-level living, this move-in ready home offers thoughtful upgrades throughout.As you approach the home, you're greeted by an elegant glass front entry door that sets the

    Khalilah Ling Crown Homes Real Estate

    8 Spring Arbor Dr, Middletown, DE 19709
  • /62

    $1,079,997

    • 5 Beds
    • 4 Baths
    • 5,658 Sq Ft

    135 Ayshire Dr, Middletown, DE 19709

    Introducing an unparalleled opportunity to own a magnificent, like-new estate in one of Middletown's most prestigious neighborhoods. This extraordinary home, nestled on over 3⁄4 of an acre, offers both grandeur and privacy. With over 6,000 sq ft of living space, this 3-year-old residence is a testament to luxury and sophistication.Upon entering, you're greeted by an open-concept design

    Jason Morris EXP Realty, LLC

    135 Ayshire Dr, Middletown, DE 19709
  • /32

    $359,900

    • 3 Beds
    • 2.5 Baths
    • 1,650 Sq Ft

    14 Springfield Cir, Middletown, DE 19709

    Step into this beautifully updated 3-bedroom, 21⁄2-bath townhouse BEST OF Willow Grove Mill community. Home offers approximately 1,650 sq ft of thoughtfully designed living space with modern comforts and classic charm. Elegant living and dining rooms boasting 9-foot ceilings and gorgeous oak hardwood floors—a sophisticated touch throughout the main level. A spacious eat-in kitchen features

    Emad Malek Tesla Realty Group, LLC

    14 Springfield Cir, Middletown, DE 19709
  • /25

    $675,000

    • 5 Beds
    • 3.5 Baths
    • 4,797 Sq Ft

    152 Tywyn Dr, Middletown, DE 19709

    Check out this beautiful and well-kept 4-bedroom, 3.5-bath home in the popular Preserves at Deep Creek community. This spacious home sits on a great lot at the end of a quiet street. As you walk in, you'll find a welcoming open hallway that leads to the lovely formal living and dining rooms. The kitchen features a large island that overlooks the great room and a bright morning room, making it

    Tijuana Garvin EXP Realty, LLC

    152 Tywyn Dr, Middletown, DE 19709
  • /21

    $498,000

    • 3 Beds
    • 2.5 Baths
    • 3,294 Sq Ft

    605 Gordon House Way, Middletown, DE 19709

    AVAILABLE NOW- READY TO MOVE-IN. This beautiful carriage style home is only made available due to a job transfer. This home is brand new, never lived in and still under the builder's warranty. Move in with a piece of mind knowing that you are the first to live here. Upon entry you are greeted by a beautiful foyer and high ceilings, a large kitchen with a beautiful island, granite countertops,

    Shakima Thimba Patterson-Schwartz-Middletown

    605 Gordon House Way, Middletown, DE 19709
  • /42

    $424,900

    • 3 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    467 Hyetts Corner Rd, Middletown, DE 19709

    Vintage charm with modern amenities. This home built in the 1800s is on just about 1 acre. It has 2 bedrooms and 2 full baths and 1 powder room. There is also an extra room in the back that could be a third bedroom . The exposed beams and brickwork are amazing. The kitchen has been updated with a quartz countertop, tile backsplash and a new stainless appliance package. You have to see this in

    Steven King Empower Real Estate, LLC

    467 Hyetts Corner Rd, Middletown, DE 19709
  • /40

    $459,000

    • 4 Beds
    • 3 Baths
    • 2,325 Sq Ft

    446 W Harvest Ln, Middletown, DE 19709

    Welcome to your dream home in one of the area’s most sought-after neighborhoods! This beautifully maintained 4-bedroom, 3-full-bath ranch-style home offers effortless single-level living in a quiet and serene community known for its top-rated school district and convenient proximity to shopping, dining, and everyday essentials. Step inside to discover a smart layout with first-floor laundry for

    David Siwy Realty Mark Associates

    446 W Harvest Ln, Middletown, DE 19709
  • /90

    $969,000

    • 5 Beds
    • 4.5 Baths
    • 5,050 Sq Ft

    830 Sweet Birch Dr, Middletown, DE 19709

    Welcome Home to 830 Sweet Birch Drive, located in the desirable PARKSIDE community in Middletown DE. This stunning home is a KINGFISHER Schell Brothers model has upgrades galore. This home is located on a wooded lot with one of the largest yard that is fully fenced in. A true walkout with a full apartment to welcome the extended family to live with you. Lets go back to the front of this home

    Ann Marie Germano Patterson-Schwartz-Middletown

    830 Sweet Birch Dr, Middletown, DE 19709
  • /41

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 2,225 Sq Ft

    141 Gillespie Ave, Middletown, DE 19709

    Nestled in the charming Willow Grove Mill community, 141 Gillespie Avenue in Middletown, DE, is a delightful townhouse that seamlessly blends comfort and style. This well-maintained home invites you into a cozy haven of thoughtfully designed living space.Step inside to discover a spacious, open layout. The main level features new flooring throughout and offers a dining area perfect for

    Jackie Patrick Compass

    141 Gillespie Ave, Middletown, DE 19709
  • /63

    $949,900

    • 5 Beds
    • 4.5 Baths
    • 5,225 Sq Ft

    810 Ashby Dr, Middletown, DE 19709

    Welcome to 810 Ashby Drive, an exquisite estate in the prestigious Ashby’s Place community. This expansive 5-bedroom, 5.5-bathroom Aspen II model by K. Hovnanian offers over 5,000 sq ft of living space, thoughtfully designed for comfort, entertaining, and modern family living.From the moment you step inside, you’re greeted by a dramatic two-story foyer, sweeping hardwood staircase, and rich

    Nakisha Powell-Jones EXP Realty, LLC

    810 Ashby Dr, Middletown, DE 19709
  • /94

    $669,900

    • 4 Beds
    • 3.5 Baths
    • 3,425 Sq Ft

    20 W Kilts Ln, Middletown, DE 19709

    Showings begin 8/1/2025! Overnight Notice Required for ALL Showing Requests. Sellers Request a Settlement Date of 10/6/25 or later. Are you looking for a large/spacious home w/ a great open floor plan?! Look no further! This lovely home is ready for its new owner! Great curb appeal w/ mature trees & bushes & plenty of freshly mulched flower beds that you can customize every year if you want!

    Team Freebery EXP Realty, LLC

    20 W Kilts Ln, Middletown, DE 19709
  • /50

    $999,000

    • 5 Beds
    • 5.5 Baths
    • 6,840 Sq Ft

    448 Spring Hollow Dr, Middletown, DE 19709

    Welcome to 448 Spring Hollow Drive. This well-maintained freshy painted colonial home sits on a lovely corner lot located in the desirable community of Parkside, with an additional 1/2 acre of non-buildable open space behind the property. Being a former model home, this 5 bedroom, 5 1/2 bath home features many well-executed upgrades, 4 fireplaces, stunning trim and lighting upgrades throughout.

    Christopher Carr HomeZu

    448 Spring Hollow Dr, Middletown, DE 19709
  • /87

    $799,000

    • 5 Beds
    • 4.5 Baths
    • 4,400 Sq Ft

    602 Harrier Ln, Middletown, DE 19709

    Why wait for New Construction, when a 1.5 year old home has so many amazing upgrades.......Welcome to this stunning Colonial-style home located in the desirable community of Pleasanton, Middletown, DE! This less then two year young spacious property boasts 5 bedrooms, 4.1 bathrooms, and is sure to impress with its elegant design and modern amenities. Inside, you'll find a well-appointed kitchen

    Ann Marie Germano Patterson-Schwartz-Middletown

    602 Harrier Ln, Middletown, DE 19709
  • /7

    $700,000

    • Land
    • 15 Acres
    • $46,296 per Acre

    0 Port Penn Rd, Middletown, DE 19709

    Discover over 15 acres of opportunity nestled just south of the canal ideal for developers or those seeking the perfect canvas for a private estate. This expansive parcel offers the rare combination of seclusion and convenience, with possible subdivision potential (subject to approvals) or room to create your own retreat surrounded by nature. Backing up to the scenic Augustine Wildlife Preserve,

    Sandy Collins Berkshire Hathaway HomeServices Homesale Realty

    0 Port Penn Rd, Middletown, DE 19709
  • /49

    $689,999

    • 5 Beds
    • 4 Baths
    • 4,700 Sq Ft

    50 Haggis Rd, Middletown, DE 19709

    Welcome to this beautiful 5 bedroom home located in the highly desirable Estates of St. Annes. This home has been impeccably maintained by its original owners. As you enter the home you have a formal dining area to your right, and a living room or office space to your right. Continuing down the hall you will enter the open kitchen and living room area with a gorgeous fireplace. There is also a

    Nigel Pokoy Compass

    50 Haggis Rd, Middletown, DE 19709
  • /66

    $693,900

    • 4 Beds
    • 3.5 Baths
    • 4,936 Sq Ft

    103 Westside Ln, Middletown, DE 19709

    Welcome to 103 Westside Lane in one of Middletown's most exclusive and coveted communities, Westside Hunt. A true estate home with curb appeal to match, this stunning home built by Disabatino Construction in 2003 is a stunner. The two-car side entry garage and oversized drive lead you home to a beautiful stone exterior and covered front porch, accented by chic black shutters and meticulous

    Megan Aitken Keller Williams Realty

    103 Westside Ln, Middletown, DE 19709
  • /27

    $475,900

    • 3 Beds
    • 2 Baths
    • 1,675 Sq Ft

    525 Contemplation Way, Middletown, DE 19709

    Welcome to 525 Contemplation Way, nestled in the highly sought-after 55+ community of Whispering Woods in Middletown, Delaware! This beautiful 3 bedroom, 2 full bathroom maintained home offers low-maintenance living with all the benefits of an active, resort-style lifestyle. Whether you're looking to downsize or embrace a vibrant new chapter, this home and community check every box. Located just

    Eric Buck Long & Foster Real Estate, Inc.

    525 Contemplation Way, Middletown, DE 19709

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