Homes with Pools for Sale in Middletown, DE

77 homes

Sort:

Recommended

NEW 24 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Middletown, DE:
Sensational Spring Arbor Community can accept 20% under age 55, no one under 18! Beautiful 2 bedroom, 2 bath, 2 car garage, 1800 SQ FT, open floor plan, 9FT ceilings and oversized paver patio. This well maintained carriage home offers one floor living! Recent Updates New Furnace January 2026, New Garage Door Opener July 2026 and New Roof October 2025! Entering the hardwood foyer to the Living Room which opens to Dining Room and Spacious Kitchen featuring an abundant cabinets, all appliances included, tile backsplash, extended granite counter space that seats four. Opens from the kitchen is a large and sunny family room with ceiling fan, fireplace and entry door to the paver patio and back y

$398,000

2 beds2 baths1,800 sq ft

264 Trellis Ln, Middletown, DE 19709

Hardwood foyer • Abundant cabinets • One floor living

(302) 285-5100

ABOUT THIS HOME
Home with a Pool for sale in Middletown, DE:
Stunning property available in the much sought after 55+ community of The Ponds at Bayberry. An opportunity to own this beautiful home for a fraction of new construction costs with upgrades and it is competitively priced for sale. A beautiful premium lot that is professionally landscaped with an underground irrigation system. This lot provides privacy with incredible views to be enjoyed from the screened porch and patio. This expanded ranch offers 4 spacious bedrooms with 3 full upgraded baths. The spacious primary suite is your personal retreat, with an ensuite bath and large walk-in closet. A fabulous gourmet chef's kitchen with a gas cook top, microwave, 2 wall ovens, vented range hood,

$749,000

4 beds3 baths3,425 sq ft

2744 Van Cliburn Cir, Middletown, DE 19709

Premium lot • Screened porch • Gas cook top

(302) 285-5100

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Middletown, DE:
Welcome to easy, first-floor living in the desirable Congressional Village community! This beautifully updated three-bedroom, two-full-bath condominium offers a move-in-ready interior, comfortable one-level living and inviting outdoor spaces. Step inside to discover fresh paint, updated LVP flooring and a renovated kitchen designed with both style and functionality in mind. The kitchen is the heart of the home featuring stainless steal appliances, granite countertops and updated white cabinets. The spacious layout provides plenty of room for everyday living, entertaining, working from home or accommodating overnight guests. Enjoy the outdoors from the screened-in porch, perfect for morning

$295,000

3 beds2 baths1,475 sq ft

1870 Congressional Village Dr #7104, Middletown, DE 19709

Screened in porch • First floor living • Updated kitchen

(302) 688-7653

OPEN FRI, 11AM TO 4PM

ABOUT THIS HOME
Home with a Pool for sale in Middletown, DE:
* * Move-in ready new construction townhome in idyllic 55+ community * * Now is the perfect time to buy your new 3BR/2.5BA home at The Venue at Winchelsea, Middletown, DE's premiere active adult community. This move-in ready two-story townhome offers low-maintenance living with sophisticated style and thoughtful design. Enter to find a dedicated study—perfect for a home office—and a convenient first-floor laundry. The gourmet kitchen shines with modern stainless steel appliances, sleek quartz countertops, 42” cabinetry, a wall oven, and gas cooktop. The open layout flows seamlessly into the dining and living areas, with an included patio to enjoy unwinding during the up

$465,500

3 beds2.5 baths2,443 sq ft

3152 Pett Level Dr, Middletown, DE 19709

Gourmet kitchen • 42 cabinetry • First-floor laundry

(856) 424-3339

NEW CONSTRUCTION

ABOUT THIS HOME
Home with a Pool for sale in Middletown, DE:
This Redford Interior townhome is one of the selected homes eligible for the Blenheim Cornerstone Initiative in compliance with the New Castle County MPDU program. Visit our website or NCC’s website for more details on qualifications and income requirements. * * This home is under construction. Delivery time frame should be discussed with a sales representative. Located in The Grove at Bayberry in Middletown, Delaware, The Redford blends contemporary comfort with everyday convenience in a way few homes can. Offering spacious rooms and open layouts with flexible living spaces, The Redford is thoughtfully crafted for all that want room to live, work, and unwind. From its inviting main

$384,000

4 beds3.5 baths2,040 sq ft

357 Edgar Degas Ln #110, Middletown, DE 19709

Unmatched location • Spacious rooms • Open layouts

(302) 254-0100

Property at 642 Vivaldi Dr, Middletown, DE 19709, 4 beds, 3 baths

$749,999

4 beds3 baths2,900 sq ft

642 Vivaldi Dr, Middletown, DE 19709

(302) 285-5100

Property at 1023 Applecross Dr, Middletown, DE 19709, 4 beds, 3.5 baths

$637,500

4 beds3.5 baths2,499 sq ft

1023 Applecross Dr, Middletown, DE 19709

(302) 734-4414

Property at 353 Edgar Degas Lane Edgar Degas #108, Middletown, DE 19709, 3 beds, 2.5 baths

$476,500

3 beds2.5 baths2,358 sq ft

353 Edgar Degas Lane Edgar Degas #108, Middletown, DE 19709

(302) 254-0100

Property at 2213 Winchelsea Pkwy, Middletown, DE 19709, 3 beds, 2.5 baths

$447,509

3 beds2.5 baths2,443 sq ft

2213 Winchelsea Pkwy, Middletown, DE 19709

(856) 424-3339

Property at 631 Red Maple Rd, Middletown, DE 19709, 3 beds, 2 baths

$499,000

3 beds2 baths1,450 sq ft

631 Red Maple Rd, Middletown, DE 19709

(302) 504-6147

Property at 813 Sweet Birch Dr, Middletown, DE 19709, 5 beds, 4 baths

$1,049,999

5 beds4 baths5,825 sq ft

813 Sweet Birch Dr, Middletown, DE 19709

(302) 285-5100

Property at 3307 Rookery Ln, Middletown, DE 19709, 3 beds, 3 baths

$557,000

3 beds3 baths2,151 sq ft

3307 Rookery Ln, Middletown, DE 19709

(856) 424-3339

Property at 211 Anglesey Dr, Middletown, DE 19709, 2 beds, 3 baths

$515,000

2 beds3 baths2,475 sq ft

211 Anglesey Dr, Middletown, DE 19709

(610) 616-0012

Property at 9 Dunswell, Middletown, DE 19709, 4 beds, 2.5 baths

$609,000

4 beds2.5 baths3,000 sq ft

9 Dunswell, Middletown, DE 19709

(302) 234-2500

Property at 268 Ann Dr, Middletown, DE 19709, 4 beds, 3.5 baths

$635,000

4 beds3.5 baths3,200 sq ft

268 Ann Dr, Middletown, DE 19709

(302) 285-5100

Property at 334 Edgar Degas Ln #100, Middletown, DE 19709, 4 beds, 3.5 baths

$384,000

4 beds3.5 baths2,040 sq ft

334 Edgar Degas Ln #100, Middletown, DE 19709

(302) 254-0100

Property at 992 Port Penn Rd, Middletown, DE 19709, 4 beds, 3 baths

$1,599,000

4 beds3 baths3,001 sq ft

992 Port Penn Rd, Middletown, DE 19709

(302) 285-5100

Property at 313 Autumn Ct, Middletown, DE 19709, 4 beds, 3.5 baths

$649,900

4 beds3.5 baths3,975 sq ft

313 Autumn Ct, Middletown, DE 19709

(302) 999-9999

Property at 1243 Gwynedd Dr, Middletown, DE 19709, 3 beds, 3 baths

$559,900

3 beds3 baths2,475 sq ft

1243 Gwynedd Dr, Middletown, DE 19709

(302) 738-2300

Property at 2638 Fairlight Dr, Middletown, DE 19709, 3 beds, 2.5 baths

$455,000

3 beds2.5 baths2,443 sq ft

2638 Fairlight Dr, Middletown, DE 19709

(888) 543-4829

Property at 2318 Schubert Ln, Middletown, DE 19709, 3 beds, 2.5 baths

$489,900

3 beds2.5 baths2,350 sq ft

2318 Schubert Ln, Middletown, DE 19709

(302) 234-1888

Property at 272 Anglesey Dr, Middletown, DE 19709, 3 beds, 3 baths

$535,000

3 beds3 baths3,303 sq ft

272 Anglesey Dr, Middletown, DE 19709

(302) 378-8700

Property at 3305 Rookery Ln, Middletown, DE 19709, 2 beds, 3 baths

$555,000

2 beds3 baths3,292 sq ft

3305 Rookery Ln, Middletown, DE 19709

(856) 424-3339

Property at 764 Ashington Dr, Middletown, DE 19709, 5 beds, 4.5 baths

$799,900

5 beds4.5 baths4,400 sq ft

764 Ashington Dr, Middletown, DE 19709

(302) 632-9673

Property at 4534 Cagney Ln, Middletown, DE 19709, 4 beds, 3 baths

$585,000

4 beds3 baths3,025 sq ft

4534 Cagney Ln, Middletown, DE 19709

(302) 202-9855

Property at 3164 Pett Level Dr, Middletown, DE 19709, 3 beds, 2.5 baths

$445,559

3 beds2.5 baths2,443 sq ft

3164 Pett Level Dr, Middletown, DE 19709

(856) 424-3339

Property at 4200 Crosby Ln, Middletown, DE 19709, 4 beds, 3 baths

$669,900

4 beds3 baths2,700 sq ft

4200 Crosby Ln, Middletown, DE 19709

(302) 373-4884

Property at 211 E Crail Ct, Middletown, DE 19709, 4 beds, 2.5 baths

$625,000

4 beds2.5 baths2,875 sq ft

211 E Crail Ct, Middletown, DE 19709

(302) 234-3800

Property at 171 Silver Maple Rd, Middletown, DE 19709, 3 beds, 2 baths

$569,900

3 beds2 baths3,558 sq ft

171 Silver Maple Rd, Middletown, DE 19709

(302) 285-5100

Property at 201 Parker Dr, Middletown, DE 19709, 5 beds, 4.5 baths

$765,000

5 beds4.5 baths4,225 sq ft

201 Parker Dr, Middletown, DE 19709

(302) 798-1000

Property at 529 Contemplation Way, Middletown, DE 19709, 3 beds, 2.5 baths

$569,900

3 beds2.5 baths2,375 sq ft

529 Contemplation Way, Middletown, DE 19709

(302) 999-9999

Property at 352 Tranquility Way, Middletown, DE 19709, 3 beds, 3 baths

$519,900

3 beds3 baths2,500 sq ft

352 Tranquility Way, Middletown, DE 19709

(302) 202-9855

Property at 1428 Whispering Woods Rd, Middletown, DE 19709, 2 beds, 2 baths

$423,000

2 beds2 baths1,275 sq ft

1428 Whispering Woods Rd, Middletown, DE 19709

(302) 273-4998

Property at 601 Yensid Dr, Middletown, DE 19709, 5 beds, 3.5 baths

$649,900

5 beds3.5 baths3,825 sq ft

601 Yensid Dr, Middletown, DE 19709

(302) 202-9855

Property at 610 Spring Hollow Dr, Middletown, DE 19709, 5 beds, 4 baths

$929,000

5 beds4 baths6,272 sq ft

610 Spring Hollow Dr, Middletown, DE 19709

(302) 674-4220

Property at 130 Burlina Blvd, Middletown, DE 19709, 2 beds, 3 baths

$565,000

2 beds3 baths2,275 sq ft

130 Burlina Blvd, Middletown, DE 19709

(302) 378-8700

Property at 623 Garden Gate Dr, Middletown, DE 19709, 2 beds, 2 baths

$469,900

2 beds2 baths1,775 sq ft

623 Garden Gate Dr, Middletown, DE 19709

(302) 234-1888

Property at 1121 Majesty Ln, Middletown, DE 19709, 4 beds, 2.5 baths

$759,900

4 beds2.5 baths3,028 sq ft

1121 Majesty Ln, Middletown, DE 19709

(302) 202-9855

Property at 336 Acasta Dr, Middletown, DE 19709, 3 beds, 2.5 baths

$540,000

3 beds2.5 baths3,100 sq ft

336 Acasta Dr, Middletown, DE 19709

(302) 234-1888

Property at 1245 Pimpernell Path, Middletown, DE 19709, 5 beds, 3.5 baths

$664,900

5 beds3.5 baths3,175 sq ft

1245 Pimpernell Path, Middletown, DE 19709

(888) 260-0040

Property at 336 Edgar Degas Lane Edgar Degas #99, Middletown, DE 19709, 3 beds, 3.5 baths

$536,300

3 beds3.5 baths2,358 sq ft

336 Edgar Degas Lane Edgar Degas #99, Middletown, DE 19709

(302) 254-0100

Viewing page 1 of 2

Homes with Pools for Sale in Middletown

There are currently 77 homes with pools for sale in Middletown at a median listing price of $470K. 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 55 days and receive 1 offers. Popular neighborhoods include Townsend Village, The Legends, and Willow Grove Mill. This map is refreshed with the newest listings in Middletown every 15 minutes.

In the past month, 29 homes have been sold in Middletown. In addition to houses in Middletown, there were also 4 condos, 34 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

"If you're looking for extra space, top-tier schools, and a tight-knit community, Middletown checks every box. You'll love the convenience of tax-free shopping, easy highway access, and an amazing array of local dining spots like La Banca and Crooked...
2 weeks ago • Middletown
R.K. Wilson
Redfin agent

More real estate resources for Middletown, DE

Neighborhoods

Zip Codes

Nearby Cities

Nearby Cities with Homes with Pools

More to explore in Middletown, DE

How to buy a house in Middletown, DE

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

4 Redfin agents serving Middletown

103

Deals*

4.8

Satisfaction

164

Homes closed*

* Data from the last year

Popular Markets in Delaware

Wilmington homes for sale
$229,900
Rehoboth Beach homes for sale
$2,548,000
Lewes homes for sale
$1,350,400
Newark homes for sale
$459,000
Bethany Beach homes for sale
$879,000
Middletown homes for sale
$503,985
Dover homes for sale
$310,000
Bear homes for sale
$389,900
New Castle homes for sale
$379,995
Fenwick Island homes for sale
$2,599,000
Selbyville homes for sale
$499,945
Smyrna homes for sale
$356,400
Hockessin homes for sale
$627,500
Dewey Beach homes for sale
$1,819,500
Milton homes for sale
$463,210

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.