Homes with Pools for Sale in Annapolis, MD

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ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
(MORE PHOTOS COMING SOON!) 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 inclu

$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 Annapolis, 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

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, 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

(410) 224-3600

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, MD:
Welcome to 786 Rolling View Drive, a beautifully reimagined 4 bedroom, 3 bathroom home in the highly sought-after Cape St. Claire community of Annapolis. Every inch of this property has been thoughtfully renovated with brand-new upgrades, including the roof, siding, flooring, recessed lighting, kitchen cabinets, countertops, fixtures, electrical, appliances, fresh paint, and a spacious new deck, creating a true turnkey opportunity. Step inside to a bright and open layout that offers effortless flow between the living, dining, and kitchen areas. The brand-new kitchen overlooks the main living space, making it ideal for everyday living and entertaining. The home features a comfortable primary

$619,900

4 beds3 baths1,980 sq ft

786 Rolling View Dr, Annapolis, MD 21409

9,000 sq ft lot • 5 parking spots • Built 1969

(443) 454-1470

ABOUT THIS HOME
Home with a Pool for sale in Annapolis, 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 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 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 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 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 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 3258 Harness Creek Rd, Annapolis, MD 21403, 3 beds, 2 baths

$1,495,000

3 beds2 baths1,694 sq ft

3258 Harness Creek Rd, Annapolis, MD 21403

(410) 260-2800

Property at 1160 Skyview Dr, Annapolis, MD 21409, 4 beds, 3 baths

$815,000

4 beds3 baths3,908 sq ft

1160 Skyview Dr, Annapolis, MD 21409

(410) 721-1500

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 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 14 Spa Creek Lndg Unit B1, Annapolis, MD 21403, 2 beds, 2 baths

$875,000

2 beds2 baths1,250 sq ft

14 Spa Creek Lndg Unit B1, Annapolis, MD 21403

(410) 263-8686

Property at 2106 Chesapeake Harbour Dr #202, Annapolis, MD 21403, 2 beds, 2 baths

$735,000

2 beds2 baths1,688 sq ft

2106 Chesapeake Harbour Dr #202, Annapolis, MD 21403

(302) 846-7839

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 703 Glendon Ave, Annapolis, MD 21403, 5 beds, 4.5 baths

$2,950,000

5 beds4.5 baths4,116 sq ft

703 Glendon Ave, Annapolis, MD 21403

(888) 860-7369

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

Property at 78 Old Mill Bottom Rd N #207, Annapolis, MD 21409, 2 beds, 2 baths

$523,655

2 beds2 baths1,317 sq ft

78 Old Mill Bottom Rd N #207, Annapolis, MD 21409

Listing provided by Zillow

Property at 78 Old Mill Bottom Rd N #112, Annapolis, MD 21409, 2 beds, 2 baths

$624,410

2 beds2 baths1,621 sq ft

78 Old Mill Bottom Rd N #112, Annapolis, MD 21409

Listing provided by Zillow

$374,950

3 beds2 baths1,040 sq ft

474 Ruffian Ct, Annapolis, MD 21409

(410) 525-5435

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 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 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 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 1181 Ramblewood Dr, Annapolis, MD 21409, 4 beds, 2.5 baths

$670,000

4 beds2.5 baths1,888 sq ft

1181 Ramblewood Dr, Annapolis, MD 21409

(410) 312-0000

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 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 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 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 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 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 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 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 3137 Catrina Ln, Annapolis, MD 21403, 3 beds, 2 baths

$1,750,000

3 beds2 baths2,970 sq ft

3137 Catrina Ln, Annapolis, MD 21403

(410) 280-5600

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 225 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 41 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, 61 homes have been sold in Annapolis. In addition to houses in Annapolis, there were also 49 condos, 54 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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