Middletown, DE homes for sale & real estate

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COMING SOON

50 Haggis Rd, Middletown, DE 19709
ABOUT THIS HOME
Middletown, DE Homes for Sale
COMING SOON 7/26/25!!!

$699,999

5 beds4 baths4,700 sq ft

50 Haggis Rd, Middletown, DE 19709

0.29 acre lot • $17 HOA • 2 garage spots

NEW 7 HRS AGO

525 Contemplation Way, Middletown, DE 19709
525 Contemplation Way, Middletown, DE 19709
525 Contemplation Way, Middletown, DE 19709
ABOUT THIS HOME
Middletown, DE Homes for Sale
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 minutes from Middletown’s vibrant Main Street, residents enjoy easy access to shops, restaurants, medical centers, and parks like Silver Lake and Augustine Wildlife Area. Come experience the perfect blend of comfort, convenience, and community—schedule your private tour of 525 Contemplat

$482,900

3 beds2 baths1,675 sq ft

525 Contemplation Way, Middletown, DE 19709

8,276 sq ft lot • $291 HOA • 2 garage spots

(302) 234-1111

OPEN SAT, 10AM TO 6PM

437 Crownleaf Dr, Middletown, DE 19709
437 Crownleaf Dr, Middletown, DE 19709
437 Crownleaf Dr, Middletown, DE 19709
ABOUT THIS HOME
Middletown, DE Homes for Sale
* 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, tile backsplash, and upgraded cabinetry), and included morning room, creating an ideal setting for gatherings. Additionally, on the first level you will find a spacious flex room and laundry room with included Whirlpool washer and dryer! The upper-level features 3 guest bedrooms, a hall bath, and

$768,457

4 beds3.5 baths4,202 sq ft

437 Crownleaf Dr, Middletown, DE 19709

0.5 acre lot • $50 HOA • 2 garage spots

(856) 424-3339

OPEN THU, 10AM TO 6PM

3128 Pett Level Dr, Middletown, DE 19709
3128 Pett Level Dr, Middletown, DE 19709
3128 Pett Level Dr, Middletown, DE 19709
ABOUT THIS HOME
Middletown, DE Homes for Sale
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 comfort and ease. The first floor features an inviting open-concept layout that blends the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The luxurious first-floor

$400,800

5 beds2 baths2,669 sq ft

3128 Pett Level Dr, Middletown, DE 19709

5,662 sq ft lot • $190 HOA • 2 garage spots

(856) 424-3339

NEW 12 HRS AGO

635 Barrie Rd, Middletown, DE 19709
635 Barrie Rd, Middletown, DE 19709
635 Barrie Rd, Middletown, DE 19709
ABOUT THIS HOME
Middletown, DE Homes for Sale
Charming Home in Sought-After Middletown Community Welcome to 635 Barrie Road, a beautifully maintained end unit town home in the sought after Appoquinimink School District. This spacious residence offers the perfect blend of comfort, style, and convenience. Featuring 3 bedrooms, 2.5 bathrooms, and 1,950 square feet of living space, this home is ideal for families, professionals, or anyone seeking a peaceful suburban lifestyle with easy access to everything Middletown has to offer. Step inside to an open and airy floor plan with gleaming hardwood floors, abundant natural light, and thoughtful upgrades throughout. The heart of the home is the gourmet kitchen, complete with granite counterto

$365,000

3 beds2.5 baths1,950 sq ft

635 Barrie Rd, Middletown, DE 19709

2,178 sq ft lot • $40 HOA • Garage

(302) 504-6147

Property at 264 N Bayberry Pkwy, Middletown, DE 19709, 3 beds, 2.5 baths

$459,900

3 beds2.5 baths2,400 sq ft

264 N Bayberry Pkwy, Middletown, DE 19709

(302) 239-3000

Property at 810 Ashby Dr, Middletown, DE 19709, 5 beds, 5.5 baths

$949,900

5 beds5.5 baths5,225 sq ft

810 Ashby Dr, Middletown, DE 19709

(888) 543-4829

Property at 133 Pine Valley Dr, Middletown, DE 19709, 4 beds, 2.5 baths

$539,900

4 beds2.5 baths2,325 sq ft

133 Pine Valley Dr, Middletown, DE 19709

(302) 999-9999

Property at 3028 Barber Ln, Middletown, DE 19709, 3 beds, 2 baths

$580,000

3 beds2 baths2,100 sq ft

3028 Barber Ln, Middletown, DE 19709

(302) 299-1100

Property at 2223 N Okeeffe Ln, Middletown, DE 19709, 3 beds, 2.5 baths

$460,000

3 beds2.5 baths1,875 sq ft

2223 N Okeeffe Ln, Middletown, DE 19709

(855) 687-2765

Property at 445 Georgiana Dr, Middletown, DE 19709, 5 beds, 3.5 baths

$579,000

5 beds3.5 baths2,900 sq ft

445 Georgiana Dr, Middletown, DE 19709

(302) 378-8700

Property at 428 Rosenberger Dr, Middletown, DE 19709, 6 beds, 5.5 baths

$1,075,000

6 beds5.5 baths6,425 sq ft

428 Rosenberger Dr, Middletown, DE 19709

(215) 627-3500

Property at 2918 Cordwainers Ln, Middletown, DE 19709, 2 beds, 3 baths

$559,900

2 beds3 baths3,422 sq ft

2918 Cordwainers Ln, Middletown, DE 19709

(856) 424-3339

Property at 1239 N Olmsted Pkwy, Middletown, DE 19709, 4 beds, 3 baths

$615,000

4 beds3 baths3,050 sq ft

1239 N Olmsted Pkwy, Middletown, DE 19709

(302) 995-1200

Property at 3132 Pett Level Dr, Middletown, DE 19709, 3 beds, 2.5 baths

$507,509

3 beds2.5 baths2,443 sq ft

3132 Pett Level Dr, Middletown, DE 19709

Listing provided by Zillow

Property at 413 Crownleaf Dr, Middletown, DE 19709, 5 beds, 4 baths

$747,800

5 beds4 baths4,479 sq ft

413 Crownleaf Dr, Middletown, DE 19709

(856) 424-3339

Property at 830 Sweet Birch Dr, Middletown, DE 19709, 5 beds, 4.5 baths

$989,000

5 beds4.5 baths4,600 sq ft

830 Sweet Birch Dr, Middletown, DE 19709

(302) 285-5100

Property at 1381 Pole Bridge Rd, Middletown, DE 19709, 3 beds, 2.5 baths

$950,000

3 beds2.5 baths3,169 sq ft

1381 Pole Bridge Rd, Middletown, DE 19709

(302) 234-2500

Property at 3 W Kilts Ln, Middletown, DE 19709, 5 beds, 3 baths

$695,000

5 beds3 baths3,450 sq ft

3 W Kilts Ln, Middletown, DE 19709

(302) 202-9855

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

$1,125,000

5 beds4.5 baths5,769 sq ft

542 Wheelmen St, Middletown, DE 19709

(302) 429-4500

Property at 2669 Fairlight Dr, Middletown, DE 19709, 2 beds, 2 baths

$544,000

2 beds2 baths1,936 sq ft

2669 Fairlight Dr, Middletown, DE 19709

(856) 424-3339

Property at 301 White Pine Dr, Middletown, DE 19709, 3 beds, 2 baths

$475,000

3 beds2 baths2,175 sq ft

301 White Pine Dr, Middletown, DE 19709

(302) 442-4200

Property at 4602 Bogart Ln, Middletown, DE 19709, 3 beds, 2 baths

$585,000

3 beds2 baths1,875 sq ft

4602 Bogart Ln, Middletown, DE 19709

(888) 543-4829

Property at 900 S Vernon St, Middletown, DE 19709, 3 beds, 1 bath

$399,000

3 beds1 bath2,000 sq ft

900 S Vernon St, Middletown, DE 19709

(302) 279-8340

Property at 40 Browning Cir, Middletown, DE 19709, 4 beds, 2.5 baths

$439,900

4 beds2.5 baths2,425 sq ft

40 Browning Cir, Middletown, DE 19709

(302) 448-6000

Property at 253 Wickerberry Dr, Middletown, DE 19709, 5 beds, 4 baths

$799,000

5 beds4 baths5,100 sq ft

253 Wickerberry Dr, Middletown, DE 19709

(302) 285-5100

Property at 620 Village Dr Unit A620, Middletown, DE 19709, 3 beds, 2 baths

$75,000

3 beds2 baths1,050 sq ft

620 Village Dr Unit A620, Middletown, DE 19709

(302) 378-8700

Property at 3112 Pett Level Dr, Middletown, DE 19709, 3 beds, 2.5 baths

$499,000

3 beds2.5 baths2,443 sq ft

3112 Pett Level Dr, Middletown, DE 19709

(856) 424-3339

Property at 104 Dungarvan Dr, Middletown, DE 19709, 4 beds, 2.5 baths

$620,000

4 beds2.5 baths2,725 sq ft

104 Dungarvan Dr, Middletown, DE 19709

(302) 688-7653

Property at 94 Willow Grove Mill Dr, Middletown, DE 19709, 4 beds, 2.5 baths

$650,000

4 beds2.5 baths2,650 sq ft

94 Willow Grove Mill Dr, Middletown, DE 19709

(302) 378-8700

Property at 407 Northhampton Way, Middletown, DE 19709, 4 beds, 3.5 baths

$550,000

4 beds3.5 baths3,523 sq ft

407 Northhampton Way, Middletown, DE 19709

(888) 543-4829

Property at 2907 Cordwainers Ln, Middletown, DE 19709, 3 beds, 3.5 baths

$525,498

3 beds3.5 baths3,397 sq ft

2907 Cordwainers Ln, Middletown, DE 19709

(856) 424-3339

Property at 7 Bristle Cone Dr, Middletown, DE 19709, 4 beds, 2 baths

$585,000

4 beds2 baths2,700 sq ft

7 Bristle Cone Dr, Middletown, DE 19709

(302) 688-7653

Property at 621 Mccracken Dr, Middletown, DE 19709, 6 beds, 4.5 baths

$749,999

6 beds4.5 baths3,877 sq ft

621 Mccracken Dr, Middletown, DE 19709

Listing provided by Zillow

Property at 251 Dillon Cir, Middletown, DE 19709, 4 beds, 4 baths

$1,090,000

4 beds4 baths4,725 sq ft

251 Dillon Cir, Middletown, DE 19709

(302) 202-9855

Property at 417 Morning Glory Ln, Middletown, DE 19709, 2 beds, 2 baths

$430,000

2 beds2 baths1,900 sq ft

417 Morning Glory Ln, Middletown, DE 19709

(302) 239-3000

Property at 414 Highland St #138, Middletown, DE 19709, 2 beds, 2.5 baths

$449,500

2 beds2.5 baths1,794 sq ft

414 Highland St #138, Middletown, DE 19709

(302) 657-8000

Property at 1205 Chesapeake View Dr, Middletown, DE 19709, 4 beds, 2.5 baths

$650,000

4 beds2.5 baths2,925 sq ft

1205 Chesapeake View Dr, Middletown, DE 19709

Listing provided by Zillow

Property at 1429 Whispering Woods Rd, Middletown, DE 19709, 2 beds, 2 baths

$459,900

2 beds2 baths2,025 sq ft

1429 Whispering Woods Rd, Middletown, DE 19709

(302) 378-8700

Property at 56 Willow Grove Mill Dr, Middletown, DE 19709, 4 beds, 3.5 baths

$689,000

4 beds3.5 baths3,900 sq ft

56 Willow Grove Mill Dr, Middletown, DE 19709

(302) 449-1422

Property at 1814 S Pollock Way, Middletown, DE 19709, 3 beds, 2.5 baths

$440,000

3 beds2.5 baths1,875 sq ft

1814 S Pollock Way, Middletown, DE 19709

(302) 688-7653

Viewing page 1 of 6

Average home prices near Middletown, DE

Cities

Zip Codes
Minor Civil Divisions

19709 homes for sale
$575,450
19734 homes for sale
$650,000

Middletown, DE real estate trends

All Home Types trends in Middletown, DE

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$443,000

-0.44% YoY | Jun 2025

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Jun 2025

Growth

% YoY

Middletown, DE

$443,000

-0.44%

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