Homes with Pools for Sale in Gentry, MD

19 homes

Sort:

Recommended

LISTED BY REDFIN3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Bring your vision and unlock the potential of this spacious three-level end-unit townhome in the sought-after community of The Gentry, just off Spa Road. Set amid a wooded landscape, the property features mature trees along the side and rear yard, with the community pool nestled down a small hill and a backdrop of additional trees beyond. This unique setting offers a wonderful sense of privacy and a peaceful backdrop while still being close to everything Annapolis has to offer. The main level features hardwood flooring, full kitchen, a convenient half bath, a wood-burning fireplace, and a bright living area opening to a rear deck overlooking the natural surroundings and pool area; a perfect

$335,900

4 beds3.5 baths1,960 sq ft

57 Gentry Ct, Annapolis, MD 21403

Bright living area • Community pool • End-unit townhome

OPEN TODAY, 1PM TO 3PMFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Located just 5 minutes from Downtown Annapolis in the quiet Gentry subdivision, this contemporary 4-bedroom, 2.5-bath home offers comfortable living across three finished levels. The main level features a bright, open living area, separate dining space, updated powder room, and a cozy kitchen with quartz countertops, modern backsplash, and painted cabinetry. A large sliding glass door fills the living room with natural light and opens to a balcony, perfect for some fresh air in the afternoons. Upstairs, the spacious primary suite includes a walk-in closet, private bath, and separate vanity area with a quartz countertop. Two additional bedrooms and a full hall bath complete the upper level.

$349,000

4 beds2.5 baths2,160 sq ft

24 Gentry Ct, Annapolis, MD 21403

Quartz countertops • Cozy kitchen • Walk-in closet

(410) 886-7342

OPEN TODAY, 11AM TO 1PM

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 4- bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury. A grand entry welcomes you with rich hardwoods (installed 2024) and graceful architectural details, leading to a large formal hexagon dining room, refined living room, and a private main-level Bedroom/Office —perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen(renovated 2024), featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cab

$850,000

4 beds4.5 baths3,586 sq ft

730 Crisfield Way, Annapolis, MD 21401

Dual wall ovens • Gourmet kitchen • Waterfront living

(703) 570-7307

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
You Will Fall In Love with this Huge, 4 Bedroom 2.5 Bath home in the Wonderful Sought after Heritage Community! 2 Family Rooms, Dining Room, Custom Tile bath, Just re-sanded Stunning Hardwood Floors throughout the main level, Master Bedroom with an ensuite bath and walk-in custom shower, New Beautiful Flooring in the lower-level Family Room, Great Rear Deck overlooking the large, fenced backyard and so much more!! The Heritage Community features a community pool is off Forest Dr. There is no HOA, just a Special Taxing district. The special taxes cover the pool. You just pay for the pool passes. heritage. hoaspace .com BE IN YOUR NEW HOME IN JUST 2 WEEKS USING PREFERRED LENDERS!

$644,900

4 beds2.5 baths2,156 sq ft

1430 Catlyn Pl, Annapolis, MD 21401

Custom tile bath • Ensuite bath • Rear deck

(410) 729-7700

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Welcome to waterfront living at The Point, one of Annapolis’ most desirable communities on Spa Creek. Thoughtfully designed to showcase the water, this one-bedroom, one-bath condo features beautiful hardwood floors, stunning Spa Creek views, and two private balconies, perfect for taking in the waterfront scenery. The updated kitchen features high end appliances and upgraded countertops, creating a clean, seamless look. The Point offers an exceptional Annapolis lifestyle with a waterfront pool, marina with boat slips for power and sailboats, tennis and pickleball courts, clubhouse, and access for kayaking and other water activities. Enjoy the convenience of walking to downtown Annapoli

$799,000

1 bed1 bath923 sq ft

5 President Point Dr Unit A2, Annapolis, MD 21403

Water views • Waterfront pool • Access for kayaking

(410) 266-0600

Property at 1 President Point Dr Unit A1, Annapolis, MD 21403, 1 bed, 1.5 baths

$825,000

1 bed1.5 baths923 sq ft

1 President Point Dr Unit A1, Annapolis, MD 21403

(410) 280-5600

Property at 402 S Cherry Grove Ave, Annapolis, MD 21401, 4 beds, 2.5 baths

$599,000

4 beds2.5 baths1,880 sq ft

402 S Cherry Grove Ave, Annapolis, MD 21401

(410) 429-7425

Property at 38 Heritage Ct, Annapolis, MD 21401, 2 beds, 1.5 baths

$265,000

2 beds1.5 baths960 sq ft

38 Heritage Ct, Annapolis, MD 21401

(443) 320-1344

Property at 6 Spa Creek Lndg Unit B2, Annapolis, MD 21403, 2 beds, 2 baths

$699,000

2 beds2 baths1,284 sq ft

6 Spa Creek Lndg Unit B2, Annapolis, MD 21403

(410) 268-8696

Property at 122 Merryman Ct, Annapolis, MD 21401, 2 beds, 1.5 baths

$249,000

2 beds1.5 baths960 sq ft

122 Merryman Ct, Annapolis, MD 21401

(410) 224-2200

Property at 5 Franklin St, Annapolis, MD 21401, 5 beds, 6.5 baths

$12,500,000

5 beds6.5 baths5,993 sq ft

5 Franklin St, Annapolis, MD 21401

(410) 280-5600

Property at 8 Spa View Cir, Annapolis, MD 21401, 5 beds, 5.5 baths

$11,500,000

5 beds5.5 baths6,061 sq ft

8 Spa View Cir, Annapolis, MD 21401

(410) 263-8686

Property at 1227-C Gemini Dr Unit C, Annapolis, MD 21403, 2 beds, 2 baths

$275,000

2 beds2 baths1,067 sq ft

1227-C Gemini Dr Unit C, Annapolis, MD 21403

(703) 349-3900

Property at 6 President Point Dr Unit B3, Annapolis, MD 21403, 3 beds, 2 baths

$975,000

3 beds2 baths1,467 sq ft

6 President Point Dr Unit B3, Annapolis, MD 21403

(410) 280-5600

Property at 6 Tiburon Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$415,000

3 beds2.5 baths1,384 sq ft

6 Tiburon Ct, Annapolis, MD 21403

(410) 224-3600

Property at 5 Park Pl #431, Annapolis, MD 21401, 1 bed, 1 bath

$475,000

1 bed1 bath839 sq ft

5 Park Pl #431, Annapolis, MD 21401

(410) 263-3400

Property at 5 Park Pl #725, Annapolis, MD 21401, 1 bed, 1 bath

$489,000

1 bed1 bath792 sq ft

5 Park Pl #725, Annapolis, MD 21401

(410) 429-7425

Property at 5 Park Pl #425, Annapolis, MD 21401, 1 bed, 1 bath

$477,900

1 bed1 bath838 sq ft

5 Park Pl #425, Annapolis, MD 21401

(410) 224-3600

Property at 5 Park Pl #732, Annapolis, MD 21401, 1 bed, 1.5 baths

$524,900

1 bed1.5 baths926 sq ft

5 Park Pl #732, Annapolis, MD 21401

(410) 224-3600

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Nestled in the charming and convenient Annapolis Overlook community, this inviting townhouse offers a perfect blend of comfort and investment potential. This traditional-style townhome boasts 1,694 square feet of thoughtfully designed living space, making it an ideal choice for both homeowners and savvy investors looking to capitalize on a desirable rental market. Step inside to discover a warm, welcoming interior with an open floor plan that seamlessly connects the kitchen and dining areas. Brand-new luxury vinyl plank flooring highlights the combined living, kitchen, and dining spaces, making it perfect for entertaining with a touch of modern elegance. The kitchen also offers ample table

$335,000

3 beds2.5 baths1,694 sq ft

40-B Ironstone Ct Unit B, Annapolis, MD 21403

Open floor plan • Ample table space • Walk-in closet

(443) 771-8009

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Welcome home to this fantastic two bedroom, two bath condo. Located on the ground level with a view of grassy area, trees, and the community pool. Open concept for the living and dining room area, with a bump out used currently as an exercise area, but it can be anything your heart desires. The modern kitchen is updated with silestone countertops, stainless appliances and the range is brand new. The living room has a slider which leads to a nice patio the grassy common area and pool beyond. The primary bedroom has a wonderfully tiled full bath, and the second bedroom shares the second bath with the common area. A brand new washer and dryer are inside the unit. Amenities include the communit

$300,000

2 beds2 baths1,217 sq ft

10 Hearthstone Ct Unit B, Annapolis, MD 21403

Community pool • Open concept • Stainless appliances

(410) 263-3400

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Welcome to this beautifully updated two level penthouse condo featuring three bedrooms, two full baths, and a thoughtfully designed open concept layout. The living and dining areas flow seamlessly together, while soaring ceilings and abundant natural light create a bright, spacious atmosphere. A cozy wood-burning fireplace adds warmth and charm. The elegant primary suite features a private en suite bath and direct access to a peaceful blacony overlooking mature trees. The perfect setting for morning coffee or evening relaxation. With modern finishes and thughtful upgrades throughout, this home is move in ready. Conveniently located near shopping, dining, public transportation, Washington, D

$309,900

3 beds2 baths1,254 sq ft

30-I Sandstone Ct, Annapolis, MD 21403

Thoughtful upgrades • Modern finishes • Open concept layout

(240) 737-5000

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Welcome to 50-G Sandstone Court, nestled in the desirable Annapolis Overlook community, where comfort, convenience, and easy living come together. This beautifully maintained 2-bedroom, 2-bath condominium is truly move-in ready and offers a bright, welcoming atmosphere you'll be proud to call home. Step inside to discover a spacious, open-concept living area that creates the perfect setting for relaxing after a long day or gathering with family and friends. Natural light fills the space, while sliding glass doors lead to a private deck overlooking peaceful green space—an ideal spot to enjoy your morning coffee, unwind with a good book, or simply take in the outdoors. The thoughtfully

$280,000

2 beds2 baths1,010 sq ft

50-G Sandstone Ct, Annapolis, MD 21403

Private deck • Second full bathroom • $330 HOA

(240) 829-9360

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
Eastport Waterfront Condo – 2BR/2BA – 1250 sq ft. 2 outdoor decks – 1 deck with amazing full city and waterfront view. Open Concept Living Room with cooks kitchen. Living Room has hardwood floors and fireplace. Newer windows and sliding doors with blinds. Full size front loader washer/dryer. Designer style Bathrooms. Community has pool, pier and tennis courts. Walk to town and live the life.

$975,000

2 beds2 baths1,260 sq ft

15 President Point Dr Unit B2, Annapolis, MD 21403

Waterfront view • Full city view • Cooks kitchen

(410) 268-8400

ABOUT THIS HOME
Home with a Pool for sale in Gentry, MD:
PRICE REDUCED FOR QUICK SALE! Back on the market with new photos! Welcome to this beautifully updated terrace-level condo offering the perfect blend of comfort and style. This 2-bedroom unit features fresh paint, brand-new carpet, and an upgraded kitchen complete with new countertops and stainless steel appliances. Enjoy easy single-level living with a spacious, open-concept layout that flows seamlessly to a private setting with peaceful forest views—ideal for relaxing or entertaining. Community amenities include an outdoor pool, fitness center, and clubhouse. Two reserved parking spaces convey. Now vacant, move-in ready, and one of the best updated values in the community—don't

$275,000

2 beds2 baths1,200 sq ft

10-K Sandstone Ct Unit K, Annapolis, MD 21403

$315 HOA • Community pool • Built 1996

(410) 272-4800

Property at 5 Market Quay, Annapolis, MD 21401, 4 beds, 4.5 baths

$3,250,000

4 beds4.5 baths3,036 sq ft

5 Market Quay, Annapolis, MD 21401

(443) 292-6767

Property at 40 Ironstone Ct Unit J, Annapolis, MD 21403, 3 beds, 2.5 baths

$329,000

3 beds2.5 baths1,680 sq ft

40 Ironstone Ct Unit J, Annapolis, MD 21403

(410) 729-7700

Homes with Pools for Sale in Gentry

There are currently 19 homes with pools for sale in Gentry. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Popular neighborhoods include Edgewater Beach, Bay Ridge, Cape St. John, West Annapolis, and Admiral Heights. This map is refreshed with the newest listings in Gentry every 15 minutes.

Find your dream home in Gentry 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 Gentry are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Gentry. If you're looking to sell your home in the Gentry area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Gentry 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 Gentry, MD

Nearby Neighborhoods

Cities

Nearby Neighborhoods with Homes with Pools

Admiral Heights homes with pools for sale

Nearby Cities with Homes with Pools

More to explore in Gentry, MD

How to buy a house in Gentry, 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

11 Redfin agents serving Gentry

341

Deals*

4.8

Satisfaction

2515

Homes closed*

* Data from the last year

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

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.