Luxury homes for sale & real estate in Middletown, DE

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3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
810 Ashby Drive is a resort-style luxury estate in Middletown’s coveted Ashby’s Place community, offering the perfect blend of high-end finishes, thoughtful updates and true indoor–outdoor living. Built in 2015 by K. Hovnanian, this expansive Aspen II model offers approximately 5,225 sq ft of finished living space with 5 bedrooms, 4 full baths and 1 half bath on a beautifully hardscaped. A dramatic two-story foyer with sweeping hardwood staircase sets the tone the moment you enter, opening to elegant formal living and dining rooms ideal for entertaining. The gourmet kitchen is the heart of the home, featuring granite countertops, an oversized prep island, double wall ovens

$949,900

5 beds4.5 baths5,225 sq ft

810 Ashby Dr, Middletown, DE 19709

Cozy gas fireplace • Gourmet kitchen • Granite countertops

(888) 543-4829

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Why build new when 1268 Pimpernell Path has all the bells and whistles! This home has over 5,500 sq. ft. and is your open-concept dream home! This stunning two-story residence features six bedrooms, four bathrooms, 9’ ceilings, a loft, sunroom, and a three-car garage and completely finished lower level. The foyer invites you past the formal living room and coat closet, leading into the heart of the home — a well-designed kitchen showcasing a large island, abundant classic white cabinetry, stainless steel appliances, and a walk-in pantry and butlers pantry. The kitchen flows seamlessly into the informal dining area, sunroom, and great room, perfect for entertaining or relaxing.

$860,000

6 beds4 baths5,590 sq ft

1268 Pimpernell Path, Middletown, DE 19709

Butlers pantry • Large island • Informal dining area

(302) 995-1200

NEW CONSTRUCTION3D WALKTHROUGH

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Modern Luxury Meets Timeless Craftsmanship on a Private 1-Acre Estate Welcome to this stunning custom-built luxury residence, meticulously designed to combine modern elegance, high-end finishes, and thoughtful functionality. Situated on a perfectly flat 1- acre lot, this exceptional home offers over 3,000 square feet of living space, every detail curated for comfort and sophistication. The exterior features bold black windows, James Hardie board & batten siding, premium vinyl siding, and metal roofing and architectural shingles. Car enthusiasts and hobbyists will appreciate the 800 square feet of garage space, including a 2-car turned garage and a separate 1- car front-facing garage,

$1,150,000

4 beds3.5 baths3,178 sq ft

415 Marcus Rd, Middletown, DE 19709

Metal roofing • Bold black windows • Private acre estate

(302) 234-1888

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
A lovely brick federal style home with some Georgian characteristics. This home is placed on the national historic register. The property itself is 14.6 acres improved by mature trees, magnificent boxwoods, and lots of privacy. The home and numerous outbuildings were originally built during the local peach era, making Monterey one of Middletown's peach plantation homes. The outbuildings have just as much history as the main house. Additionally featured are several barns, a second 3 bedroom home, 4 car garage, and a 3 hole privy which is also on the historic register along with the unique ice and smoke houses. This country estate home is a great opportunity to add your restoration touches an

$1,200,000

— beds— baths7,026 sq ft

692 Bayview Rd, Middletown, DE 19709

14.6 acres • Several barns • Lots of privacy

(410) 885-1606

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to 434 Spring Hollow Drive, a beautiful residence nestled in Middletown's most sought-after community. This home is ideally situated on one of the finest lots, offering tranquil views as it backs onto lush woods. Located on a charming tree-lined street, it's just a short walk to the community clubhouse, which boasts a large pool and fitness center. As you approach the home, the inviting front porch welcomes you. Step inside to be greeted by stunning hardwood floors that extend throughout the first floor and up to the second level. The first floor features a versatile office, a cozy living room, an elegant dining room, and a gourmet kitchen that overlooks the family room, complete wi

$899,999

5 beds3.5 baths5,092 sq ft

434 Spring Hollow Dr, Middletown, DE 19709

0.45 acre lot • 4 garage spots • Community pool

(302) 202-9855

Property at 542 Wheelmen St, Middletown, DE 19709, 5 beds, 4.5 baths

$1,069,000

5 beds4.5 baths5,548 sq ft

542 Wheelmen St, Middletown, DE 19709

(302) 475-0800

Property at 757 Idlewyld Dr, Middletown, DE 19709, 5 beds, 5.5 baths

$999,999

5 beds5.5 baths4,425 sq ft

757 Idlewyld Dr, Middletown, DE 19709

(302) 738-2300

Property at 448 Spring Hollow Dr, Middletown, DE 19709, 5 beds, 5.5 baths

$899,000

5 beds5.5 baths6,840 sq ft

448 Spring Hollow Dr, Middletown, DE 19709

(855) 885-4663

Property at 1215 Bunker Hill Rd, Middletown, DE 19709, 4 beds, 4.5 baths

$1,249,000

4 beds4.5 baths4,300 sq ft

1215 Bunker Hill Rd, Middletown, DE 19709

(302) 504-6147

Property at 258 Dillon Cir, Middletown, DE 19709, 4 beds, 3.5 baths

$995,000

4 beds3.5 baths4,175 sq ft

258 Dillon Cir, Middletown, DE 19709

(302) 477-5500

Property at 135 Ayshire Dr, Middletown, DE 19709, 5 beds, 4 baths

$1,079,997

5 beds4 baths5,658 sq ft

135 Ayshire Dr, Middletown, DE 19709

(888) 543-4829

Property at 1343 Bohemia Mill Rd, Middletown, DE 19709, 4 beds, 4.5 baths

$5,100,000

4 beds4.5 baths4,650 sq ft

1343 Bohemia Mill Rd, Middletown, DE 19709

(302) 449-1422

Property at 129 Ayshire Dr Unit PLAZA, Middletown, DE 19709, 4 beds, 3.5 baths

$884,990

4 beds3.5 baths4,569 sq ft

129 Ayshire Dr Unit PLAZA, Middletown, DE 19709

(888) 543-4829

Property at The Plaza Plan, Middletown, DE 19709, 4 beds, 3.5 baths

$884,990

4 beds3.5 baths4,569 sq ft

The Plaza Plan, Middletown, DE 19709

Listing provided by Zillow

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NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,425,000

4 beds4 baths— sq ft

3002 Blackston Dr, Townsend, DE 19734

1 acre lot • 3 garage spots • Listed 10 days

(302) 378-9510

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,460,300

5 beds4 baths— sq ft

3001 Blackston Dr, Townsend, DE 19734

1 acre lot • 3 garage spots • Listed 10 days

(302) 378-9510

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,510,300

5 beds4 baths— sq ft

108 Witherspoon Way, Townsend, DE 19734

1 acre lot • 3 garage spots • Listed 10 days

(302) 378-9510

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,299,000

4 beds3.5 baths3,722 sq ft

114 Witherspoon Way, Townsend, DE 19734

1 acre lot • 2 garage spots • Listed 10 days

(302) 378-9510

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,475,000

4 beds4 baths— sq ft

3010 Blackston Dr, Townsend, DE 19734

1 acre lot • 3 garage spots • Listed 10 days

(302) 378-9510

NEW CONSTRUCTION

ABOUT THIS HOME
Luxury Home for sale in Middletown, DE:
Welcome to Blackston Cove — Delaware’s newest premier home community. Here, you’ll find 11 elegantly designed models, each offering striking exterior facades and thoughtfully crafted interior layouts. Set on expansive one-acre homesites, Blackston Cove provides the space, and privacy that today’s homeowners desire. Every residence is an elite custom home, built with high-end finishes and exceptional attention to detail. Choose from a selection of four- and five-bedroom models, each tailored to elevate comfort, style, and modern living. Blackston Cove — where craftsmanship, luxury, and spacious living come together to create the perfect place to call home.

$1,410,300

5 beds3.5 baths— sq ft

104 Witherspoon Way, Townsend, DE 19734

1 acre lot • 3 garage spots • Listed 10 days

(302) 378-9510

Property at 102 Witherspoon Way, Townsend, DE 19734, 4 beds, 4 baths

$1,399,000

4 beds4 baths— sq ft

102 Witherspoon Way, Townsend, DE 19734

(302) 378-9510

Property at 106 Witherspoon Way, Townsend, DE 19734, 4 beds, 3.5 baths

$1,375,000

4 beds3.5 baths— sq ft

106 Witherspoon Way, Townsend, DE 19734

(302) 378-9510

Property at 3008 Blackston Dr, Townsend, DE 19734, 5 beds, 4 baths

$1,434,300

5 beds4 baths— sq ft

3008 Blackston Dr, Townsend, DE 19734

(302) 378-9510

Property at 557 Mansion House Rd, Bear, DE 19701, 3 beds, 2 baths

$1,795,000

3 beds2 baths2,050 sq ft

557 Mansion House Rd, Bear, DE 19701

(302) 369-5397

Property at 404 Wiggins Mill Rd, Townsend, DE 19734, 5 beds, 4.5 baths

$1,329,000

5 beds4.5 baths4,431 sq ft

404 Wiggins Mill Rd, Townsend, DE 19734

(302) 273-4998

Property at 0 Cecilton-warwick Rd, 1, Cecilton, MD 21912

$1,750,000

— beds— baths— sq ft

0 Cecilton-warwick Rd, 1, Cecilton, MD 21912

(410) 398-9200

Property at 556 Union Church Rd, Townsend, DE 19734, 4 beds, 1 bath

$1,999,995

4 beds1 bath— sq ft

556 Union Church Rd, Townsend, DE 19734

(302) 299-1100

Property at 2159 Mccoy Rd, Bear, DE 19701, 4 beds, 4.5 baths

$1,250,000

4 beds4.5 baths5,825 sq ft

2159 Mccoy Rd, Bear, DE 19701

(302) 202-9855

Property at 1455 Cayots Corner Rd, Chesapeake City, MD 21915, 4 beds, 4 baths

$29,800,000

4 beds4 baths— sq ft

1455 Cayots Corner Rd, Chesapeake City, MD 21915

(302) 654-6500

Property at 199 Pine Tree Rd, Townsend, DE 19734, 3 beds, 2 baths

$950,000

3 beds2 baths— sq ft

199 Pine Tree Rd, Townsend, DE 19734

(302) 453-3200

Property at 2956 Frazer Rd, Newark, DE 19702, 4 beds, 1 bath

$997,900

4 beds1 bath2,400 sq ft

2956 Frazer Rd, Newark, DE 19702

(302) 477-5500

Property at 300 Bohemia Ave, Chesapeake City, MD 21915, 9 beds, 10 baths

$1,489,000

9 beds10 baths7,044 sq ft

300 Bohemia Ave, Chesapeake City, MD 21915

(410) 398-9200

Luxury Homes for Sale in Middletown

There are currently 14 luxury homes for sale in Middletown at a median listing price of $448K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Middletown stay on the market for 38 days and receive 3 offers. Popular neighborhoods include Willow Grove Mill, and Estates at St. Annes. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 34 homes have been sold in Middletown. In addition to houses in Middletown, there were also 3 condos, 25 townhouses, and 1 multi-family unit for sale in Middletown last month. Middletown is a minimally walkable city in New Castle County with a Walk Score of 29. Middletown is home to approximately 18,479 people and 5,276 jobs. Find your dream home in Middletown using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Middletown are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Middletown. Our Middletown real estate stats and trends will give you more information about home buying and selling trends in Middletown. If you're looking to sell your home in the Middletown area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Middletown with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

Redfin agent insights on Middletown, DE homes

What do I love about Middletown? Honestly… everything. Middletown has this perfect mix of small-town charm and modern convenience that just feels like home. Grab coffee from a locally owned café, stroll through one of our beautiful parks, and still...
1 month ago • Middletown
Sherri Hill
Redfin agent

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Luxury homes for sale & real estate in Middletown, DE

Luxury Homes for Sale in Middletown

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