138

Middletown, DE 2-Story Homes for Sale

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  • /87

    $989,000

    • 5 Beds
    • 4.5 Baths
    • 4,600 Sq Ft

    830 Sweet Birch Dr, Middletown, DE 19709

    Coming Soon!!!!! walk out full apartment..backs to woods...Main floor primary suite.....Schell Brothers Kingfisher.....5 bedroom, 5 baths....description and pictures coming

    Ann Marie Germano Patterson-Schwartz-Middletown

    830 Sweet Birch Dr, Middletown, DE 19709
  • /34

    $550,000 Open Sun 2PM - 4PM

    • 3 Beds
    • 2.5 Baths
    • 2,925 Sq Ft

    2209 Rossini Ln, Middletown, DE 19709

    This 3 years young, this spotless home will take your breath away! Located in the highly desired 55+ Village of Bayberry South, it is loaded with upgrades, ready for its new owners to move in. Situated on a premium lot, across the street from protected, green space, you'll notice the curb appeal as soon as you arrive. Step in the front door and admire the vaulted entry way, which is filled with

    Dorothy Donovan Keller Williams Realty Wilmington

    2209 Rossini Ln, Middletown, DE 19709
  • /19

    $349,900

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

    421 Quincy Ave, Middletown, DE 19709

    Welcome to 421 Quincy Drive, an end-unit townhome nestled in the Willow Grove Mill community. Step inside to an open and airy layout, perfect for everyday living and effortless entertaining. The main level features two expansive living areas, ideal for family gatherings, movie nights, or flexible work-from-home setups. The kitchen is a standout, boasting 42” cabinets and a breakfast bar with

    Oliver Millwood Empower Real Estate, LLC

    421 Quincy Ave, Middletown, DE 19709
  • /65

    $949,900 Open Sun 2PM - 4PM

    • 5 Beds
    • 5.5 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
  • /96

    $535,000

    • 4 Beds
    • 2.5 Baths
    • 2,675 Sq Ft

    603 Cheswick Ct, Middletown, DE 19709

    Located in the highly sought-after Brick Mill Farms community in Middletown, this spacious 4-bedroom, 2.5-bath home offers generous living space and endless potential. Featuring a formal living room and dining room, the home is thoughtfully designed for both comfortable living and entertaining. The eat-in kitchen flows seamlessly into a dramatic two-story family room, creating a bright and open

    Laura Walker Walker Realty Group LLC

    603 Cheswick Ct, Middletown, DE 19709
  • /44

    $599,900

    • 4 Beds
    • 2.5 Baths
    • 3,581 Sq Ft

    1242 Hook Dr, Middletown, DE 19709

    Welcome to this stunning 4-bedroom, 2.5-bath home featuring an open floor plan ideal for both everyday living and entertaining. The spacious kitchen boasts a large island, abundant cabinetry, and seamlessly flows into the dining area and a cozy family room — perfect for gathering with loved ones. The primary suite offers a luxurious retreat with a generous walk-in closet, garden tub, and

    Sandy Collins Berkshire Hathaway HomeServices Homesale Realty

    1242 Hook Dr, Middletown, DE 19709
  • /24

    $349,000

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

    178 Gillespie Ave, Middletown, DE 19709

    Welcome to this beautifully updated Colonial-style townhome located in the highly sought-after Willow Grove Mill community in Middletown. With 1,650 sq. ft. of thoughtfully designed living space, this 3-bedroom, 2.5-bath home offers a perfect blend of comfort, convenience, and modern style. Freshly painted throughout, it features brand-new luxury vinyl flooring on the main level, new carpet

    Judy Chen BHHS Fox & Roach - Hockessin

    178 Gillespie Ave, Middletown, DE 19709
  • /27

    $482,900 Open Sat 12PM - 2PM

    • 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
  • /37

    $539,900

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

    133 Pine Valley Dr, Middletown, DE 19709

    Situated on a large corner lot, this home has been lovingly maintained by the original owners. Don't miss this traditional colonial with spacious rooms and many updates. Updates include the freshly painted interior (2025) , hickory engineered hardwood flooring on the first level (2024), new carpet on the second level and stairs (2024), and updated bathrooms (2025). The eat-in kitchen features

    SUSAN HELMSTADTER BHHS Fox & Roach - Hockessin

    133 Pine Valley Dr, Middletown, DE 19709
  • /60

    $579,000

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

    445 Georgiana Dr, Middletown, DE 19709

    Welcome to your next chapter in comfort and convenience! This spacious five-bedroom, three-and-a-half-bath home offers a layout designed for both everyday living and entertaining. The open floor plan connects the kitchen, dining, and living areas, making gatherings easy and enjoyable—whether you’re hosting game night or just making pancakes on a Sunday morning.Downstairs, the finished

    Tiny Reamer RE/MAX 1st Choice - Middletown

    445 Georgiana Dr, Middletown, DE 19709
  • /44

    $950,000

    • 3 Beds
    • 2.5 Baths
    • 3,169 Sq Ft

    1381 Pole Bridge Rd, Middletown, DE 19709

    Here it is, your own piece of ground with a whole lot of extras. 1381 Pole Bridge Road offers nearly 8 acres with a pole building, in-ground heated pool, and 3,619 square foot home in Appo School District. This property offers privacy and serenity rarely found New Castle County. The home features and open concept layout with kitchen, dining, and family room flowing together on the main level. The

    Travis L. Dorman RE/MAX Elite

    1381 Pole Bridge Rd, Middletown, DE 19709
  • /45

    $599,000

    • 4 Beds
    • 2.5 Baths
    • 2,725 Sq Ft

    104 Dungarvan Dr, Middletown, DE 19709

    Welcome to 104 Dungarvan Dr, a true gem of a home with charm and beauty, located in one of the most exclusive and sought-after communities in Middletown, DE. The curb appeal, accented by mature trees and a stunning brick exterior with classic shutters flanking the windows, makes for a glowing first impression. The one-acre lot offers privacy and sprawling usable space while still maintaining a

    Megan Aitken Keller Williams Realty

    104 Dungarvan Dr, Middletown, DE 19709
  • /64

    $430,000

    • 3 Beds
    • 2.5 Baths
    • 1,875 Sq Ft

    1814 S Pollock Way, Middletown, DE 19709

    Welcome to 1814 S Pollock Way in the Village of Bayberry, a welcoming, and growing community full of activities, parks, trails, and quickly expanding for convenience with it's premier location near the upcoming Bayberry Town Center, bringing convenient shopping, professional offices, and community spaces right to the neighborhood. 1814 S Pollock offers stunning curb appeal, with stone facing and

    Megan Aitken Keller Williams Realty

    1814 S Pollock Way, Middletown, DE 19709
  • /52

    $465,000

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

    343 Daylilly Way, Middletown, DE 19709

    Welcome to 343 Daylilly Way, a beautifully maintained home in the sought-after 55+ community of Springmill in Middletown, DE. This 2-bedroom, 3-bath home features a smart layout with two bedrooms and a flex room on the main floor, plus a private loft with a third full bath—ideal for guests or hobbies. Hardwood floors flow throughout the main living areas, accented by crown molding and natural

    Lalisa Sweat Crown Homes Real Estate

    343 Daylilly Way, Middletown, DE 19709
  • /54

    $479,900

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

    577 Whispering Trail, Middletown, DE 19709

    Welcome home to this impeccably maintained Coleridge model, ideally situated within the sought-after Active Adult Community of Springmill in Middletown, Delaware. This residence has been meticulously cared for and offers recent upgrades, including a new roof, HVAC system, and electric water heater, ensuring peace of mind for years to come. Upon entering, you’ll be greeted by gleaming hardwood

    Vicky Miller Patterson-Schwartz-Middletown

    577 Whispering Trail, Middletown, DE 19709
  • /48

    $599,000

    • 5 Beds
    • 4.5 Baths
    • 3,600 Sq Ft

    240 Armata Dr, Middletown, DE 19709

    Enjoy nearly 3,600 sq ft of living space—an outstanding value at $599K in the 5-bedroom market—nestled near the end of a quiet cul-de-sac in the sought-after Appoquinimink School District, with key comparables ranging from $579K to $605K. A thoughtfully designed, 5 bed, 4.5 bath, 3,600 sq. ft modern home located near the end of a quiet cul-de-sac, where peace, privacy, and convenience

    Veta McCarther VRA Realty

    240 Armata Dr, Middletown, DE 19709
  • /16

    $395,900

    • 3 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    460 Brockton Dr, Middletown, DE 19709

    Back on the Market due to failure of Buyer to obtain financing. FHA appraisal recently completed for $407,000. Don't miss out on this rare, total renovation, of a spectacular 2100 sq ft, 3br, 2.5ba, 1 car garage end unit townhome boasting 11 additional windows on the side, making this home a haven of sunlight. This end home is situated on one of the larger home sites in the community of Willow

    Rebecca P Minner RE/MAX Eagle Realty

    460 Brockton Dr, Middletown, DE 19709
  • /68

    $899,000

    • 5 Beds
    • 4.5 Baths
    • 5,800 Sq Ft

    102 W Crail Ct, Middletown, DE 19709

    Discover refined elegance in this stunning 5-bedroom, 3.5-bath mansion located in one of Middletown’s most sought-after neighborhoods. This expansive home features breathtaking marble flooring, soaring ceilings, and designer finishes throughout.The grand entry opens to beautifully appointed living and dining spaces, leading to a gourmet kitchen with high-end appliances, custom cabinetry,

    Grace Casella Crown Homes Real Estate

    102 W Crail Ct, Middletown, DE 19709
  • /52

    $714,995

    • 5 Beds
    • 3.5 Baths
    • 3,775 Sq Ft

    114 Saint Augustine Ct, Middletown, DE 19709

    Welcome to 114 Saint Augustine Ct. in the esteemed Back Creek golf community of Middletown, DE- where luxury and elegance meet on the what many locals consider the most coveted block in the neighborhood. This exquisite 5-bedroom, 3.5-bathroom colonial gem, masterfully crafted by Bonvetti builders, is set on a sprawling 0.74-acre lot with stunning views of the 4th tee.Step inside to

    Jason Morris EXP Realty, LLC

    114 Saint Augustine Ct, Middletown, DE 19709
  • /36

    $619,900

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

    124 Willow Grove Mill Dr, Middletown, DE 19709

    Welcome to this charming Colonial-style home located in the desirable Longmeadow in the Town of Middletown. The beautiful washed brick facade and covered front door welcomes you in. This spacious property boasts 4 bedrooms, 2.5 bathrooms, and is spread across 2 levels/stories, offering ample space for comfortable living. As you enter, you are greeted by a two story foyer with the formal living

    Ann Marie Deysher Patterson-Schwartz-Hockessin

    124 Willow Grove Mill Dr, Middletown, DE 19709
  • /41

    $769,900

    • 4 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    340 Ellenwood Dr, Middletown, DE 19709

    Welcome to 340 Ellenwood Drive, located in one of Middletown’s most desirable communities within the Appoquinimink School District. This prime location offers close proximity to parks, shopping, dining, and commuter routes, all while providing a strong sense of community and everyday convenience. This home features a covered front porch, perfect for enjoying the peaceful neighborhood setting.

    Eric Buck Long & Foster Real Estate, Inc.

    340 Ellenwood Dr, Middletown, DE 19709
  • /31

    $465,000

    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    358 Tiger Lily Dr, Middletown, DE 19709

    Come and Take Advantage of this $10,000 Price Improvement on this beautiful home! Welcome to this 4 bedroom, 2.5 bath Twin in the neighborhood of High Hook Farms located in the Highly Sought after Appoquinimink School District! This home checks all the boxes; location, amenities and superb schooling! Walk inside with me and notice the beautiful handscraped hardwoods throughout the main level

    Tyler Andrews Empower Real Estate, LLC

    358 Tiger Lily Dr, Middletown, DE 19709
  • /76

    $799,990

    • 4 Beds
    • 4.5 Baths
    • 5,925 Sq Ft

    113 Anna Ct, Middletown, DE 19709

    Welcome home to this beautiful home located in the highly sought after community of Back Creek. This home is on a cul de sac, has an acre plus of land that is fully landscaped with green giants for the ultimate privacy.... a great deck for you to enjoy the peace and quiet. This amazing home is over 6000 square feet, 4 bedrooms, 4.1 bathrooms, a finished basement, a morning room, a 2 story

    Ann Marie Germano Patterson-Schwartz-Middletown

    113 Anna Ct, Middletown, DE 19709
  • /46

    $550,000

    • 4 Beds
    • 2.5 Baths
    • 2,875 Sq Ft

    522 Lilac Dr, Middletown, DE 19709

    Welcome to 522 Lilac Drive, Middletown, DE — where comfort meets convenience in this beautifully maintained single-family home! Located in the desirable Longmeadow neighborhood, this spacious 4-bedroom, 2.5-bathroom detached home offers nearly 3000 square feet of thoughtfully designed living space, perfect for both everyday living and entertaining. Step inside to find a bright and airy

    David Vetri Red Brick Realty, LLC

    522 Lilac Dr, Middletown, DE 19709
  • /20

    $418,000

    • 3 Beds
    • 3.5 Baths
    • 2,150 Sq Ft

    439 Goodwick Dr, Middletown, DE 19709

    **Back on the Market! This beautiful home in now available again due to no fault of the seller. Don't miss your change to own this wonderful home!** Welcome to this charming 3-bedroom, 3.5-bath townhouse with a one-car garage in the desirable Deep Creek community! The main level boasts a spacious living room that flows into the dining area, complete with a slider leading to the

    Christina Quinn Empower Real Estate, LLC

    439 Goodwick Dr, Middletown, DE 19709
  • /59

    $769,900

    • 6 Beds
    • 4.5 Baths
    • 5,761 Sq Ft

    117 Shannon Blvd, Middletown, DE 19709

    Come see your next home in the charming community of Middletown! This home (The Monticello Model) combines timeless elegance with modern features. As you step inside, the angled staircase makes a striking first impression, while the formal living and dining rooms offer spacious, luxurious areas for entertaining. The chef-inspired kitchen, equipped with a wall oven and gas cooktop, is expanded by

    Christian Swalm Real Broker LLC

    117 Shannon Blvd, Middletown, DE 19709
  • /68

    $750,000

    • 6 Beds
    • 5 Baths
    • 4,500 Sq Ft

    1032 Applecross Dr, Middletown, DE 19709

    Welcome to 1032 Applecross Drive in the Preserve at Deep Creek. This expansive & well-appointed home is the largest in its community and offers all the high-end features and amenities you could possibly want, and a blank canvas to make your very own! Spanning over 4,500 square feet amongst three levels of living spaces, the highlights include a bright & open floorplan with 9-foot ceilings, a

    Michael McKee Long & Foster Real Estate, Inc.

    1032 Applecross Dr, Middletown, DE 19709
  • /17

    $535,000

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

    110 Lahinch Ct, Middletown, DE 19709

    Seller Motivated! Incredible Opportunity Awaits! This California Contemporary home is located within the highly sought-after Back Creek golf course community and the highly rated Appoquinimink School District. Situated on a sprawling 3/4-acre lot, this property offers breathtaking vistas of the 11th hole. The main floor boasts a luxurious Primary Suite, providing both comfort and convenience,

    William Sladek Redfin Corporation

    110 Lahinch Ct, Middletown, DE 19709
  • /79

    $699,900

    • 5 Beds
    • 3.5 Baths
    • 3,125 Sq Ft

    119 Tuscany Dr, Middletown, DE 19709

    PARKSIDE - Welcome to 119 Tuscany Drive, an elegant and inviting residence located in the heart of Middletown and within the APPOQUINIMINK SCHOOL DISTRICT. This exquisite 5-bedroom, 3.5-bathroom home offers a harmonious blend of sophistication and comfort. Newly built in 2015 by Lifestyle Builders, this home has been lovingly maintained by its original owners. Enter the foyer to find gleaming

    Andrea Harrington Compass

    119 Tuscany Dr, Middletown, DE 19709
  • /74

    $755,000

    • 4 Beds
    • 4 Baths
    • 4,155 Sq Ft

    114 Austrian Pine Ct, Middletown, DE 19709

    Now featured at $755,000This stunning new home in the highly sought-after Four Seasons at Baymont Farms is now even more appealing! This home offers the perfect blend of luxury, convenience, and value in a premier 55+ community. Don't miss out on this rare opportunity to own a spacious 4-bedroom, 4-bathroom home in a fantastic location!Property Features:*4 Spacious

    Maha Johnson EXP Realty, LLC

    114 Austrian Pine Ct, Middletown, DE 19709
  • /17

    $370,000

    • 4 Beds
    • 1 Bath
    • 2,350 Sq Ft

    705 Bethel Church Rd, Middletown, DE 19709

    Come check out this single-family home, located on 1.1 acres of land. Home is in the #1 school district,(Appoquinimink). Property needs a new septic system, and good bit of work, but could make a great investment. Schedule your tours today!

    Ryan Haas RE/MAX Edge

    705 Bethel Church Rd, Middletown, DE 19709
  • /38

    $464,900

    • 4 Beds
    • 2.5 Baths
    • 2,150 Sq Ft

    325 Great Oak Dr, Middletown, DE 19709

    Classic R.C. Peoples-built 2 Story in rarely available Great Oak Farms. This home has fantastic curb appeal starting with the brick siding, but not forgetting the long driveway that is complimented by two decorative brick pillars. Moving inside, there is a living room with a cozy fireplace; just a few steps away from the formal dining room. The kitchen its own dining area, no shortage of cabinet

    Matt Dutt RE/MAX Elite

    325 Great Oak Dr, Middletown, DE 19709
  • /46

    $540,000

    • 4 Beds
    • 3.5 Baths
    • 2,825 Sq Ft

    373 Northhampton Way, Middletown, DE 19709

    Say hello to this lovely home located in the tree-lined, quiet community of Willow Grove Mills, easily accessible to prestigious schools, shopping, dining, healthcare, and routes leading to the beach. The home features an open-concept living and dining room with lots of natural light and a fireplace for those cozy nights. The kitchen features an eat-in option with tall cabinets and granite

    Christian Webb Sky Realty

    373 Northhampton Way, Middletown, DE 19709
  • /2

    $475,000

    • 3 Beds
    • 3.5 Baths
    • 2,175 Sq Ft

    301 White Pine Dr, Middletown, DE 19709

    This is a unique one! 1+ Acre lot - not one but 2 oversized attached/rear access garages AND a detached garage too! New roof in 2024! This home has a unique floor plan - some smart re-configuring allows flexibility in the use of space. This home is eligible for a VA Assumption for a VA Buyer who wants to take advantage of a low interest rate. More pics to follow. Showings will take place at the

    Lisa Marie RE/MAX Edge

    301 White Pine Dr, Middletown, DE 19709
  • /17

    $779,900 New Construction

    • 6 Beds
    • 4.5 Baths
    • 3,707 Sq Ft

    844 Merlin Dr, Middletown, DE 19709

    Make room for more in this expansive Varna-ESP, a 6-bedroom, 4.5-bath home with farmhouse-inspired style and modern comfort at every turn. With a finished basement, stained ceiling beams, and a freestanding tub in the primary suite, this home balances cozy charm with elevated design.The gourmet kitchen is equipped with a smart cooking suite, dual ovens, and a Profile French door fridge,

    Barbara Heilman Delaware Homes Inc

    844 Merlin Dr, Middletown, DE 19709
  • /20

    $768,457 Open Sat 10AM - 6PM

    • 4 Beds
    • 3.5 Baths
    • 4,202 Sq Ft

    437 Crownleaf Dr, Middletown, DE 19709

    *SUMMER SAVINGS HAPPENING NOW!* Say hello to 437 Crownleaf Drive, our stunning Emerson Farmhouse! Step in off your front porch and be greeted by a grand double story entry way with your formal dining room off to one side, and home office on the other. Moving inward, an open layout seamlessly connects the double story family room with cozy fireplace, gourmet kitchen (complete w/ quartz counters,

    David Vasso Atlantic Five Realty

    437 Crownleaf Dr, Middletown, DE 19709
  • /26

    $400,800 Open Sat 10AM - 6PM

    • 5 Beds
    • 2 Baths
    • 2,669 Sq Ft

    3128 Pett Level Dr, Middletown, DE 19709

    Welcome to Venue at Winchelsea by Lennar — Middletown’s premier active adult (55+) community offering low-maintenance living, spacious designs, and exceptional value. This 2,669 sq. ft. two-story townhome is part of Lennar’s Pathway to Ownership Program -application and income qualification are required for purchase.3128 Pett Level Drive is a Fall move-in home thoughtfully designed for

    David Vasso Atlantic Five Realty

    3128 Pett Level Dr, Middletown, DE 19709
  • /23

    $559,900 Open Sun 11AM - 6PM

    • 2 Beds
    • 3 Baths
    • 3,422 Sq Ft

    2918 Cordwainers Ln, Middletown, DE 19709

    *SUMMER SAVINGS HAPPENING NOW!** Middletown’s fastest-selling active adult community, Venue at Winchelsea is nearly sold out of its first phase of single-family homes—don’t miss your chance to own an incredible home at an unbeatable value! Welcome to the Mendocino Luxe. A 2 bedroom, 3 bathroom home, with a finished basement, 2918 Cordwainers Lane, is sure to check all of your boxes! When

    David Vasso Atlantic Five Realty

    2918 Cordwainers Ln, Middletown, DE 19709
  • /22

    $507,509 New Construction

    • 3 Beds
    • 2.5 Baths
    • 2,443 Sq Ft

    3132 Pett Level Dr, Middletown, DE 19709

    Welcome to Venue at Winchelsea - Middletown's Premiere 55+ Active Adult community. Location is the key- you will not want to miss out on this end unit townhome that backs up to open space with fabulous views! The Taylor is a brand new two-story, townhome that is designed to promote low-maintenance living with a sophisticated twist. As you enter, you’re greeted by a dedicated study, perfect for a

    Lennar

    Taylor, Middletown, DE 19709
  • /24

    $747,800 Open Sat 10AM - 6PM

    • 5 Beds
    • 4 Baths
    • 4,479 Sq Ft

    413 Crownleaf Dr, Middletown, DE 19709

    *Fall move-in!* Say hello to 413 Crownleaf Dr, Copperleaf’s dual owner's suite home! The Emerson II is thoughtfully designed to fit everything you love. Enter, and be greeted by a grand entry way with your formal dining room and office located in the front of your home. Moving inward, a spacious open layout seamlessly connects the family room with cozy fireplace, gourmet kitchen (complete w/

    David Vasso Atlantic Five Realty

    413 Crownleaf Dr, Middletown, DE 19709

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