Homes with Pools for Sale in 21401, MD

104 homes

Sort:

Recommended

OPEN SAT, 1PM TO 3PMVIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in 21401, MD:
Outstanding location and “Cape Cod” charm await at 309 N. Woodlawn Avenue in the highly sought out community of Homewood. If walkability to all downtown Annapolis is what you seek, this is the house for you! Located just a few steps from the USNA stadium, walking paths and parks & playing fields! This home features a large, fenced back yard complete with paver patio and mature trees…perfect for BBQs and cozy fire pit evenings! On the main level you will find hardwood floors throughout, and sunlit beautiful living room including a wood burning fireplace! The kitchen offers white cabinets, granite countertops, and plenty of table space including built-in bench with st

$650,000

4 beds2 baths1,653 sq ft

309 N Woodlawn Ave N, Annapolis, MD 21401

8,210 sq ft lot • Built 1951

(410) 263-3400

ABOUT THIS HOME
Home with a Pool for sale in 21401, MD:
Stunningly Updated Historic District Charmer! Nestled near the top of iconic Cornhill Street—just steps from State Circle and the boutiques and restaurants of Maryland Avenue—this beautifully restored brick end-unit blends timeless Annapolis character with modern luxury. Step inside to an inviting open floor plan filled with natural light and accented by gleaming heart pine floors. The highlight of the main level is the completely renovated gourmet kitchen, featuring quartz countertops, stainless steel appliances, custom cabinetry, and designer finishes—a perfect blend of elegance and functionality. The flexible living/dining space offers built-ins, a wood-burning fireplac

$875,000

3 beds2 baths1,376 sq ft

54 Cornhill St, Annapolis, MD 21401

Built 1800 • Listed 2 days

(410) 224-3600

ABOUT THIS HOME
Home with a Pool for sale in 21401, MD:
Arts & Crafts–inspired residence built in 2012 by Gate One Builders and designed by Fred Sieracki with exceptional materials and craftsmanship. Set on an elevated and private 5.46-acre wooded property, this home offers Broad Creek/ South River views, a deep-water, 100 ft private pier with boat lift, floating dock for kayaks, a living shoreline, and a fully fenced property with deer fencing. Exterior highlights include HardiePlank siding, custom stonework, curated landscaping, an outdoor shower, and a firepit. Inside, the first floor is reminiscent of a lodge-style retreat with vaulted ceilings and blue knotty pine wood floors reclaimed from a 1900s South Carolina mill. The open

$1,998,000

3 beds3 baths2,835 sq ft

397 Forelands Rd, Annapolis, MD 21401

5.46 acre lot • 4 parking spots • Built 2012

(410) 263-8686

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in 21401, MD:
Tremendous opportunity to own a beautiful, recently updated home in Riva Trace. Additional pictures and details coming soon!

$799,900

5 beds3.5 baths2,625 sq ft

202 Autumn Leaf Pl, Annapolis, MD 21401

9,578 sq ft lot • 2 garage spots • Built 1985

(410) 729-7700

ABOUT THIS HOME
Home with a Pool for sale in 21401, MD:
Step into the heart of Heritage Harbour, where opportunities like this do not come to market often. Nestled on a quiet, well-kept cul-de-sac, this beautifully maintained home offers a warm welcome from the moment you arrive. Fresh interior paint sets the tone throughout, creating a bright and inviting space that is ready for immediate occupancy. Designed with comfortable everyday living in mind, the layout features three spacious bedrooms along with a converted sunroom that includes its own half bath. This flexible area is ideal for a fourth bedroom, hobby room, or private guest suite. As you walk through the foyer and enter the large living room, natural light fills the space and highlight

$629,000

4 beds2.5 baths1,812 sq ft

950 Bermuda Ln, Annapolis, MD 21401

8,276 sq ft lot • 2 garage spots • Community pool

(888) 860-7369

Property at 1800 Severn Grove Rd, Annapolis, MD 21401, 3 beds, 3 baths

$967,000

3 beds3 baths2,281 sq ft

1800 Severn Grove Rd, Annapolis, MD 21401

(410) 260-2800

Property at 134 Spring Place Way, Annapolis, MD 21401, 2 beds, 3.5 baths

$485,000

2 beds3.5 baths2,021 sq ft

134 Spring Place Way, Annapolis, MD 21401

(410) 429-7425

Property at 612 Severn Island Ct, Annapolis, MD 21401, 3 beds, 2.5 baths

$399,999

3 beds2.5 baths1,450 sq ft

612 Severn Island Ct, Annapolis, MD 21401

(301) 493-5575

Property at 1915 Towne Centre Blvd #502, Annapolis, MD 21401, 2 beds, 2 baths

$545,000

2 beds2 baths1,485 sq ft

1915 Towne Centre Blvd #502, Annapolis, MD 21401

(410) 263-3400

$555,000

4 beds3.5 baths2,640 sq ft

911 Boom Way, Annapolis, MD 21401

(301) 652-0643

Property at 341 Dubois Rd, Annapolis, MD 21401, 3 beds, 2.5 baths

$475,000

3 beds2.5 baths2,317 sq ft

341 Dubois Rd, Annapolis, MD 21401

(301) 945-9010

Property at 2942 Southaven Dr, Annapolis, MD 21401, 4 beds, 2.5 baths

$949,900

4 beds2.5 baths2,142 sq ft

2942 Southaven Dr, Annapolis, MD 21401

(410) 280-5600

Property at 39 Southgate Ave, Annapolis, MD 21401, 5 beds, 3.5 baths

$3,750,000

5 beds3.5 baths6,789 sq ft

39 Southgate Ave, Annapolis, MD 21401

(410) 280-5600

Property at 2639 Greenbriar Ln, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,650,000

3 beds2.5 baths3,888 sq ft

2639 Greenbriar Ln, Annapolis, MD 21401

(410) 260-2800

Property at 524 Ridge Rd, Annapolis, MD 21401, 4 beds, 3 baths

$799,000

4 beds3 baths2,944 sq ft

524 Ridge Rd, Annapolis, MD 21401

(301) 970-2447

Property at 2705 Coxswain Pl, Annapolis, MD 21401, 2 beds, 2 baths

$650,000

2 beds2 baths1,547 sq ft

2705 Coxswain Pl, Annapolis, MD 21401

(443) 901-2200

Property at 1831 Drew St, Annapolis, MD 21401, 5 beds, 2 baths

$570,000

5 beds2 baths2,236 sq ft

1831 Drew St, Annapolis, MD 21401

(443) 318-8800

Property at 2638 Greenbriar Ln, Annapolis, MD 21401, 4 beds, 2 baths

$650,000

4 beds2 baths2,606 sq ft

2638 Greenbriar Ln, Annapolis, MD 21401

(410) 296-8440

Property at 122 Waterline Ct, Annapolis, MD 21401, 4 beds, 4 baths

$615,000

4 beds4 baths2,450 sq ft

122 Waterline Ct, Annapolis, MD 21401

(410) 429-7425

Property at 212 Duke Of Gloucester St, Annapolis, MD 21401

$599,900

0 beds— baths2,300 sq ft

212 Duke Of Gloucester St, Annapolis, MD 21401

(443) 573-9200

Property at 2155 Scotts Crossing Ct #303, Annapolis, MD 21401, 2 beds, 2 baths

$339,900

2 beds2 baths1,126 sq ft

2155 Scotts Crossing Ct #303, Annapolis, MD 21401

(410) 266-0600

Property at 4 Roosevelt Dr, Annapolis, MD 21401, 4 beds, 2 baths

$475,000

4 beds2 baths2,016 sq ft

4 Roosevelt Dr, Annapolis, MD 21401

(410) 721-9600

Property at 627 Tripp Creek Ct, Annapolis, MD 21401, 4 beds, 2.5 baths

$369,999

4 beds2.5 baths1,822 sq ft

627 Tripp Creek Ct, Annapolis, MD 21401

(410) 465-6900

Property at 2 Southgate Ave #10, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,975,000

3 beds2.5 baths3,884 sq ft

2 Southgate Ave #10, Annapolis, MD 21401

(410) 280-5600

Property at 1909 Eleanor Ct, Annapolis, MD 21401, 5 beds, 3.5 baths

$950,000

5 beds3.5 baths4,790 sq ft

1909 Eleanor Ct, Annapolis, MD 21401

(410) 823-0033

Property at 629 Admiral Dr Unit H8-305, Annapolis, MD 21401, 2 beds, 2 baths

$394,900

2 beds2 baths1,449 sq ft

629 Admiral Dr Unit H8-305, Annapolis, MD 21401

(443) 292-6767

Property at 2828 Berth Ct, Annapolis, MD 21401, 2 beds, 2 baths

$500,000

2 beds2 baths1,434 sq ft

2828 Berth Ct, Annapolis, MD 21401

(888) 860-7369

Property at 34 Lafayette Ave, Annapolis, MD 21401, 3 beds, 1 bath

$599,900

3 beds1 bath2,280 sq ft

34 Lafayette Ave, Annapolis, MD 21401

(410) 547-1116

Property at 201 Bowie Ave, Annapolis, MD 21401, 4 beds, 3 baths

$574,900

4 beds3 baths1,709 sq ft

201 Bowie Ave, Annapolis, MD 21401

(410) 312-0000

Property at 2008 Peggy Stewart Way, Annapolis, MD 21401, 3 beds, 2 baths

$385,000

3 beds2 baths1,313 sq ft

2008 Peggy Stewart Way, Annapolis, MD 21401

Property at 228 Dubois Rd, Annapolis, MD 21401, 4 beds, 3 baths

$675,000

4 beds3 baths2,900 sq ft

228 Dubois Rd, Annapolis, MD 21401

(410) 260-2800

Property at 110 Marquise Ln, Annapolis, MD 21401, 3 beds, 2.5 baths

$769,000

3 beds2.5 baths2,066 sq ft

110 Marquise Ln, Annapolis, MD 21401

(443) 988-0483

Property at 1808 Lincoln Dr, Annapolis, MD 21401, 3 beds, 1 bath

$419,000

3 beds1 bath1,008 sq ft

1808 Lincoln Dr, Annapolis, MD 21401

(410) 547-1116

Property at 301 Unity Ln, Annapolis, MD 21401, 5 beds, 5.5 baths

$1,127,000

5 beds5.5 baths7,616 sq ft

301 Unity Ln, Annapolis, MD 21401

(301) 570-0087

Property at 173 Williams Dr, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,425,000

4 beds3.5 baths2,382 sq ft

173 Williams Dr, Annapolis, MD 21401

(410) 280-5600

Property at 1974 Scotts Crossing Way #102, Annapolis, MD 21401, 3 beds, 2 baths

$379,000

3 beds2 baths1,328 sq ft

1974 Scotts Crossing Way #102, Annapolis, MD 21401

(443) 921-3900

Property at 302 Forbes St Unit D, Annapolis, MD 21401, 2 beds, 2 baths

$450,000

2 beds2 baths844 sq ft

302 Forbes St Unit D, Annapolis, MD 21401

(410) 429-7425

Property at 111 Clay St, Annapolis, MD 21401, 3 beds, 1.5 baths

$525,000

3 beds1.5 baths1,568 sq ft

111 Clay St, Annapolis, MD 21401

(855) 450-0442

Property at 2704 Summerview Way #103, Annapolis, MD 21401, 2 beds, 2 baths

$365,000

2 beds2 baths1,285 sq ft

2704 Summerview Way #103, Annapolis, MD 21401

(301) 970-2447

Property at 606 James Walker Pl, Annapolis, MD 21401, 3 beds, 4 baths

$605,000

3 beds4 baths2,272 sq ft

606 James Walker Pl, Annapolis, MD 21401

(410) 263-3400

Property at 825 Coxswain Way, Annapolis, MD 21401, 2 beds, 2 baths

$545,000

2 beds2 baths1,691 sq ft

825 Coxswain Way, Annapolis, MD 21401

(443) 901-2200

Viewing page 1 of 3

Homes with Pools for Sale in 21401

There are currently 104 homes with pools for sale in 21401 at a median listing price of $675K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21401 stay on the market for 45 days and receive 1 offers. This map is refreshed with the newest listings in 21401 every 15 minutes.

In the past month, 61 homes have been sold in 21401. In addition to houses in 21401, there were also 52 condos, 50 townhouses, and 1 multi-family unit for sale in 21401 last month. Find your dream home in 21401 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 21401 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21401. If you're looking to sell your home in the 21401 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21401 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for 21401, MD

Cities

Nearby Zip Codes

Nearby Zip Codes with Homes with Pools

Nearby Cities with Homes with Pools

More to explore in 21401, MD

How to buy a house in 21401, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

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

Why Redfin?

Community Impact

Diversity & Inclusion

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.