Homes with Pools for Sale in Annapolis, MD

217 homes

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NEW 3 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
INVESTOR ALERT!!! This cottage has a newer roof, 2018, and a encapsulated and sump installed in a sealed crawl space 2022. Large back yard with rain garden. She needs some good TLC but excellent investment opportunity! Over 1400 sq ft, 3 bedroom, 2 full bath, Peek-a-boo water view and great location . Close to all the community privledges and being sold strictly "AS IS". More photos are on their way!

$450,000

3 beds2 baths1,412 sq ft

3426 Narragansett Ave, Annapolis, MD 21403

Newer roof • Large back yard • Rain garden

(410) 263-8686

NEW 3 HRS AGO

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
Step inside this beautifully renovated 2-bedroom, 2-bathroom condo in Annapolis Overlook and instantly feel coastal charm meet modern comfort. This isn’t just a home—it’s a lifestyle rooted in the heart of Annapolis, where history, community, and the Chesapeake Bay come together in a way only this city can offer. Annapolis Overlook provides resort-style living with a sparkling outdoor pool, a clubhouse ideal for gatherings, and meticulously maintained grounds that create the feel of a private retreat. Located on the ground level, this condo is fully ADA-compliant and includes an oversized assigned parking spot—an everyday convenience rarely found in condo living. Ins

$300,000

2 beds2 baths1,217 sq ft

30-A Hearthstone Ct Unit A, Annapolis, MD 21403

$303 HOA • Parking • Community pool

(410) 956-3500

OPEN SAT, 1PM TO 3PMVIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, 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 • Listed 2 days

(410) 263-3400

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
Coming Soon, this Friday! Perfect Heritage Harbour Location. Granite Counters, Stainless Appliances. Professionally painted with new flooring. Spacious back deck with awning.

$489,900

5 beds5 baths1,434 sq ft

1984 Marconi Cir, Annapolis, MD 21401

$176 HOA • Garage • Community pool

(410) 793-7195

COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
Discover an exquisite blend of luxury and comfort in this stunning split foyer home, nestled in the prestigious Annapolis Roads community. This meticulously maintained residence, a major renovation in 2025, boasts an impressive 4 bedrooms and 3 full baths, offering ample space for relaxation and entertainment. Step inside to find an open floor plan that seamlessly connects the gourmet kitchen, back splash and under cabinet lighting and featuring upgraded countertops and a spacious island, to the inviting living and dining areas. Elegant wood floors and recessed lighting enhance the ambiance, while a cozy wood-burning fireplace adds warmth to the heart of the home. The entry-level bedroom pr

$739,000

4 beds3 baths2,296 sq ft

1031 Old Bay Ridge Rd, Annapolis, MD 21403

0.28 acre lot • Garage • Built 1968

(410) 260-2800

Property at 54 Cornhill St, Annapolis, MD 21401, 3 beds, 2 baths

$875,000

3 beds2 baths1,376 sq ft

54 Cornhill St, Annapolis, MD 21401

(410) 224-3600

Property at 150 E Bay View Dr, Annapolis, MD 21403, 3 beds, 2 baths

$995,000

3 beds2 baths2,187 sq ft

150 E Bay View Dr, Annapolis, MD 21403

(410) 486-4504

Property at 397 Forelands Rd, Annapolis, MD 21401, 3 beds, 3 baths

$1,998,000

3 beds3 baths2,835 sq ft

397 Forelands Rd, Annapolis, MD 21401

(410) 263-8686

Property at 165 King George St, Annapolis, MD 21401, 4 beds, 3 baths

$1,375,000

4 beds3 baths2,649 sq ft

165 King George St, Annapolis, MD 21401

(410) 266-9005

Property at 474 Ruffian Ct, Annapolis, MD 21409, 3 beds, 2 baths

$374,950

3 beds2 baths1,232 sq ft

474 Ruffian Ct, Annapolis, MD 21409

(410) 525-5435

Property at 786 Rolling View Dr, Annapolis, MD 21409, 4 beds, 3 baths

$619,900

4 beds3 baths1,980 sq ft

786 Rolling View Dr, Annapolis, MD 21409

(443) 454-1470

Property at 52 Primrose Hill Ln, Annapolis, MD 21403, 5 beds, 4.5 baths

$949,000

5 beds4.5 baths3,978 sq ft

52 Primrose Hill Ln, Annapolis, MD 21403

(443) 292-6767

Property at 950 Bermuda Ln, Annapolis, MD 21401, 4 beds, 2.5 baths

$629,000

4 beds2.5 baths1,812 sq ft

950 Bermuda Ln, Annapolis, MD 21401

(888) 860-7369

Property at 106 Roselawn Rd, Annapolis, MD 21403, 4 beds, 2 baths

$350,000

4 beds2 baths1,323 sq ft

106 Roselawn Rd, Annapolis, MD 21403

(410) 544-8800

Property at 202 Autumn Leaf Pl, Annapolis, MD 21401, 5 beds, 3.5 baths

$799,900

5 beds3.5 baths2,625 sq ft

202 Autumn Leaf Pl, Annapolis, MD 21401

(410) 729-7700

Property at P. 317 Shot Town Rd, Arnold, MD 21409, 5 beds, 4.5 baths

$2,195,000

5 beds4.5 baths4,219 sq ft

P. 317 Shot Town Rd, Arnold, MD 21409

(410) 647-8000

Property at 1138 Lake Heron Dr Unit 2A, Annapolis, MD 21403, 2 beds, 2 baths

$385,000

2 beds2 baths1,103 sq ft

1138 Lake Heron Dr Unit 2A, Annapolis, MD 21403

(410) 224-2200

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

Property at 926 Yachtsman Way, Annapolis, MD 21403, 2 beds, 2 baths

$415,000

2 beds2 baths1,174 sq ft

926 Yachtsman Way, Annapolis, MD 21403

(301) 970-2447

$555,000

4 beds3.5 baths2,640 sq ft

911 Boom Way, Annapolis, MD 21401

(301) 652-0643

$405,000

3 beds2.5 baths1,740 sq ft

132 Quiet Waters Pl, Annapolis, MD 21403

(443) 372-7171

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 133 Lake View Dr, Annapolis, MD 21403, 5 beds, 5 baths

$1,400,000

5 beds5 baths4,308 sq ft

133 Lake View Dr, Annapolis, MD 21403

(410) 280-5600

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 3 Chester Ave, Annapolis, MD 21403, 3 beds, 3 baths

$1,730,000

3 beds3 baths2,815 sq ft

3 Chester Ave, Annapolis, MD 21403

(410) 972-4000

Property at 621 Wood Lot Trail Rd, Annapolis, MD 21401, 5 beds, 3.5 baths

$894,900

5 beds3.5 baths3,970 sq ft

621 Wood Lot Trail Rd, Annapolis, MD 21401

(703) 821-1840

Property at 30 Decatur Ave, Annapolis, MD 21403, 4 beds, 2 baths

$1,100,000

4 beds2 baths1,477 sq ft

30 Decatur Ave, Annapolis, MD 21403

(410) 280-5600

Property at 6 Victor Pkwy, Annapolis, MD 21403, 3 beds, 1 bath

$374,900

3 beds1 bath912 sq ft

6 Victor Pkwy, Annapolis, MD 21403

(410) 729-7700

Property at 200 Chesapeake Ave, Annapolis, MD 21403, 2 beds, 1.5 baths

$1,099,000

2 beds1.5 baths2,942 sq ft

200 Chesapeake Ave, Annapolis, MD 21403

(703) 310-6111

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 1913 Dulaney Pl, Annapolis, MD 21409, 5 beds, 2 baths

$925,000

5 beds2 baths2,969 sq ft

1913 Dulaney Pl, Annapolis, MD 21409

(410) 224-3200

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

$605,000

4 beds4 baths2,450 sq ft

122 Waterline Ct, Annapolis, MD 21401

(410) 429-7425

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 1007 Park Ave, Annapolis, MD 21403, 3 beds, 3 baths

$1,075,000

3 beds3 baths2,430 sq ft

1007 Park Ave, Annapolis, MD 21403

(410) 972-4000

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 2203 Mulberry Hill Rd, Annapolis, MD 21409, 3 beds, 2.5 baths

$1,350,000

3 beds2.5 baths1,994 sq ft

2203 Mulberry Hill Rd, Annapolis, MD 21409

(410) 263-8686

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 30 Gentry Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$349,000

3 beds2.5 baths1,460 sq ft

30 Gentry Ct, Annapolis, MD 21403

(410) 263-8686

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Homes with Pools for Sale in Annapolis

There are currently 217 homes with pools for sale in Annapolis 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 Annapolis stay on the market for 50 days and receive 4 offers. Popular neighborhoods include Anchorage, West Annapolis, Gingerville, Admiral Heights, and Old Annapolis Neck. This map is refreshed with the newest listings in Annapolis every 15 minutes.

In the past month, 37 homes have been sold in Annapolis. In addition to houses in Annapolis, there were also 45 condos, 52 townhouses, and 1 multi-family unit for sale in Annapolis last month. Annapolis is a minimally walkable city in Maryland with a Walk Score of 48. Annapolis is home to approximately 37,699 people and 25,456 jobs. Find your dream home in Annapolis 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 Annapolis are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Annapolis. Our Annapolis real estate stats and trends will give you more information about home buying and selling trends in Annapolis. If you're looking to sell your home in the Annapolis area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Annapolis with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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