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Middletown

Located just 24 miles south of Wilmington, and 24 miles north of Dover, Middletown is part of Delaware's fastest-growing towns. The community offers residents several parks, a six-acre catch-and-release fishing pond, walking trails, and many playgrounds. There are also numerous community events throughout the year.

View The Market Report

Available Homes in Middletown

141 MIDDESSA DR, Middletown, DE 19709
Open Sun 12PM-2PM
50

$664,900

5 Beds 3 Baths 3,225 SqFt

141 MIDDESSA DR, Middletown, DE 19709

MLS# DENC2113610

Listed by Century 21 Emerald

Bright MLS (BMLS)
Bright MLS (BMLS)
2601 ALEXANDER CALDER CT, Middletown, DE 19709
Open Sun 1PM-3PM
77

$899,900

5 Beds 6 Baths 5,375 SqFt

2601 ALEXANDER CALDER CT, Middletown, DE 19709

MLS# DENC2113558

Listed by RE/MAX Associates-Wilmington

Bright MLS (BMLS)
Bright MLS (BMLS)
110 SHANNON BLVD, Middletown, DE 19709
Open Sat 12PM-2PM
45

$790,000

5 Beds 5 Baths 4,397 SqFt

110 SHANNON BLVD, Middletown, DE 19709

MLS# DENC2112318

Listed by Crown Homes Real Estate

Bright MLS (BMLS)
Bright MLS (BMLS)
3304 ROOKERY LN, Middletown, DE 19709
Open Fri 11AM-4PM
42

$531,352

2 Beds 3 Baths 1,778 SqFt

3304 ROOKERY LN, Middletown, DE 19709

MLS# DENC2113394

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
3024 IVYHOUSE LN, Middletown, DE 19709
Open Fri 11AM-4PM
41

$557,273

3 Beds 4 Baths 2,151 SqFt

3024 IVYHOUSE LN, Middletown, DE 19709

MLS# DENC2111266

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
3152 PETT LEVEL DR, Middletown, DE 19709
Open Fri 11AM-4PM
61

$419,659

3 Beds 3 Baths 2,443 SqFt

3152 PETT LEVEL DR, Middletown, DE 19709

MLS# DENC2110802

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
1026 WICKERSHAM WAY, Middletown, DE 19709
Open Sun 1PM-3PM
28

$369,900

3 Beds 3 Baths 1,500 SqFt

1026 WICKERSHAM WAY, Middletown, DE 19709

MLS# DENC2109956

Listed by Real Broker LLC

Bright MLS (BMLS)
Bright MLS (BMLS)
2213 WINCHELSEA PKWY, Middletown, DE 19709
Open Fri 11AM-4PM
67

$413,009

3 Beds 3 Baths 2,443 SqFt

2213 WINCHELSEA PKWY, Middletown, DE 19709

MLS# DENC2110504

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
6307 SUNCREST WAY, Middletown, DE 19709
Open Fri 11AM-4PM
32

$747,701

5 Beds 4 Baths 3,448 SqFt

6307 SUNCREST WAY, Middletown, DE 19709

MLS# DENC2109978

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
6052 FREESTONE BLVD, Middletown, DE 19709
Open Fri 11AM-4PM
36

$499,900

3 Beds 4 Baths 2,368 SqFt

6052 FREESTONE BLVD, Middletown, DE 19709

MLS# DENC2109994

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
6624 HARKO DR, Middletown, DE 19709
Open Fri 11AM-4PM
27

$469,000

3 Beds 4 Baths 2,361 SqFt

6624 HARKO DR, Middletown, DE 19709

MLS# DENC2110006

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
3034 IVYHOUSE LN, Middletown, DE 19709
Open Fri 11AM-4PM
47

$571,718

3 Beds 4 Baths 2,151 SqFt

3034 IVYHOUSE LN, Middletown, DE 19709

MLS# DENC2107686

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
3314 ROOKERY LN, Middletown, DE 19709
Open Fri 11AM-4PM
41

$559,672

3 Beds 4 Baths 2,151 SqFt

3314 ROOKERY LN, Middletown, DE 19709

MLS# DENC2107606

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
21 CANARY CT, Middletown, DE 19709
Open Sat 1PM-3PM
67

$679,000

5 Beds 4 Baths 5,075 SqFt

21 CANARY CT, Middletown, DE 19709

MLS# DENC2104332

Listed by Crown Homes Real Estate

Bright MLS (BMLS)
Bright MLS (BMLS)
2228 WINCHELSEA PKWY, Middletown, DE 19709
Open Fri 11AM-4PM
48

$499,000

3 Beds 3 Baths 3,397 SqFt

2228 WINCHELSEA PKWY, Middletown, DE 19709

MLS# DENC2096366

Listed by Atlantic Five Realty

Bright MLS (BMLS)
Bright MLS (BMLS)
642 GORDON HOUSE WAY, Middletown, DE 19709
Open Tue 9AM-5PM
25

$634,900

4 Beds 3 Baths 2,889 SqFt

642 GORDON HOUSE WAY, Middletown, DE 19709

MLS# DENC2091264

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
452 REDERICK LN #MASSEY ELITE LOT 65, Middletown, DE 19709
Open Mon 8AM-8PM
15

$474,900

3 Beds 3 Baths 2,380 SqFt

452 REDERICK LN #MASSEY ELITE LOT 65, Middletown, DE 19709

MLS# DENC2090408

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
548 LONGHORN LOOP #LOT 33 CHELSEA, Middletown, DE 19709
Open Mon 8AM-8PM
38

$688,893

3 Beds 2 Baths 2,296 SqFt

548 LONGHORN LOOP #LOT 33 CHELSEA, Middletown, DE 19709

MLS# DENC2088952

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
204 BALDY LN #COTTONWOOD MODEL, Middletown, DE 19709
Open Fri 11AM-5PM
11

$622,000

3 Beds 2 Baths 2,477 SqFt

204 BALDY LN #COTTONWOOD MODEL, Middletown, DE 19709

MLS# DENC2080210

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
204 BALDY LN #CHELSEA MODEL, Middletown, DE 19709
Open Tue 11AM-5PM
39

$607,000

3 Beds 2 Baths 2,296 SqFt

204 BALDY LN #CHELSEA MODEL, Middletown, DE 19709

MLS# DENC2080208

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
204 BALDY LN #CAYOT MODEL, Middletown, DE 19709
Open Thu 11AM-5PM
41

$587,000

3 Beds 2 Baths 2,004 SqFt

204 BALDY LN #CAYOT MODEL, Middletown, DE 19709

MLS# DENC2080204

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
530 WHEELMEN ST #6 CHARLESTON, Middletown, DE 19709
Open Tue 11:30AM-4PM
4

$590,000

4 Beds 3 Baths 2,730 SqFt

530 WHEELMEN ST #6 CHARLESTON, Middletown, DE 19709

MLS# DENC2079248

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
530 WHEELMEN ST #5 CHADWICK, Middletown, DE 19709
Open Tue 11:30AM-4PM
41

$570,500

4 Beds 3 Baths 2,456 SqFt

530 WHEELMEN ST #5 CHADWICK, Middletown, DE 19709

MLS# DENC2079246

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)
530 WHEELMEN ST #1 EDMONSTON, Middletown, DE 19709
Open Tue 11:30AM-4PM
24

$591,000

4 Beds 3 Baths 2,716 SqFt

530 WHEELMEN ST #1 EDMONSTON, Middletown, DE 19709

MLS# DENC2079210

Listed by RE/MAX Elite

Bright MLS (BMLS)
Bright MLS (BMLS)

Data provided by Bright MLS. Property information is for the users personal, non-commercial use. Information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties that appear on the website may no longer be for sale, and may be under contract or sold. ©2026 Bright MLS, All Rights Reserved. Information is reliable but not guaranteed.

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    © 2026 Stape & Associates | LIC #RB1709 | Compass RE - All rights reserved | Privacy Policy | DMCA Policy | Powered by Blok.

    Stape & Associates is a team of real estate agents affiliated with Compass RE, a licensed real estate broker and abides by Equal Housing Opportunity laws. All material presented herein is intended for informational purposes only. Information is compiled from sources deemed reliable but is subject to errors, omissions, changes in price, condition, sale, or withdrawal without notice. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions.