Hillsmere Shores, MD homes for sale & real estate

7 homes

Sort:

Recommended

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Welcome to 123 Maple Drive in sought-after, amenity-rich Hillsmere Estates! This updated 3-bedroom, 3-full-bath home features a spacious main-level bedroom, new windows, new LVP flooring on the main level, and new carpet on the stairs and upper level. The updated kitchen offers new quartz countertops, stainless steel appliances, and a new stove and microwave. The primary ensuite has been completely renovated, and the other two full baths have also been updated. A new sliding glass door leads to the large, new custom-built deck overlooking a spacious, flat, fenced rear yard—plenty of room for entertaining, playing, or relaxing outdoors. A two-car garage with a new garage door adds conv

$725,000

3 beds3 baths1,928 sq ft

123 Maple Dr, Annapolis, MD 21403

0.25 acre lot • 2 garage spots • Community pool

(410) 224-3600

FLOOR PLAN

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash,

$554,990

3 beds2.5 baths2,514 sq ft

416 Walnut Dr, Annapolis, MD 21403

Updated home • Expanded kitchen • Peaceful backyard

(410) 729-7700

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfront community. Completely transformed with a warm, modern aesthetic, this 4-bedroom, 3-bath home offers approximately 2,450 square feet of beautifully finished living space. From the moment you arrive, the crisp white board-and-batten exterior and inviting curb appeal set the tone. Inside, brand-new natural birch flooring, solid wood interior doors, crown molding, recessed lighting, and carefully selected finishes create a bright, cohesive feel throughout the main level. The open living spaces are designed for both everyday l

$850,000

4 beds3 baths2,450 sq ft

327 Beach Dr, Annapolis, MD 21403

0.41 acre lot • Garage • Community pool

(301) 702-4200

COMING SOON

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Imagine ending your day on a wraparound porch, watching the sun set over Hillsmere Lake! Welcome to 611 Harbor Drive, a six-bedroom, three-bath Colonial offering approximately 3,200 square feet of living space, beautiful water views, and the sought-after amenities of Hillsmere Shores. Situated on a generous one-third-acre lot, this home was completely renovated in 2001 and offers an open, inviting floor plan with generously sized living and gathering spaces. The kitchen flows into the dining and living areas and features stainless steel appliances installed in 2025, a gas range, and a vent hood. An electric fireplace, also added in 2025, brings warmth and ambiance, while a separate, spaciou

$925,000

6 beds3 baths3,072 sq ft

611 Harbor Dr, Annapolis, MD 21403

Water views • Wraparound porch • Electric fireplace

(888) 860-7369

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Don't miss out on this great location. Looks can be deceiving. Must see inside to appreciate all this home has to offer. Sellers are highly motivated and flexible with a closing date. Details and features; -The kitchen used to be the carport -Upper cabinets in the kitchen are custom made -Luxury vinyl flooring in kitchen -Propane fireplace in living room/insert is only 2 years old -Propane gas for grill -2-100-gallon propane tanks/owned -Propane back up heat -Blown in insulation in attic area -Master bath gutted and updated 5 years ago -HVAC units in lower level and in barn/garage -Lower-level walk out to bar area and firepit -Full covered huge deck -Fully fenced back yard -Private access t

$749,000

4 beds3 baths2,156 sq ft

278 Hillsmere Dr, Annapolis, MD 21403

Covered deck • Propane fireplace • Open airy floor plan

(410) 263-8686

Property at 130 Great Lake Dr, Annapolis, MD 21403, 4 beds, 2.5 baths

$650,000

4 beds2.5 baths2,100 sq ft

130 Great Lake Dr, Annapolis, MD 21403

(410) 263-8686

Property at 927 Old Annapolis Neck Rd, Annapolis, MD 21403, 1 bath

$1,100,000

Land1.50 acres (lot)

927 Old Annapolis Neck Rd, Annapolis, MD 21403

(919) 360-0430

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

OPEN TODAY, 10AM TO 12PMFLOOR PLAN

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Experience effortless coastal living at 957 Breakwater Dr. This impeccably maintained townhouse in Mariners Landing balances comfort and convenience. The bright main level flows into a dedicated dining area, perfect for hosting. The fully equipped kitchen boasts generous cabinetry for easy meal prep. A sliding glass door opens to an unfenced backyard, a pristine blank canvas ready for your custom patio or garden design. A powder room and deep storage closet complete the first floor. Upstairs, discover a rare layout featuring TWO primary suites. Both generous bedrooms act as private retreats with plush carpeting, ceiling fans, and en-suite full bathrooms. Upper-level laundry streamlines your

$350,000

2 beds2.5 baths1,392 sq ft

957 Breakwater Dr, Annapolis, MD 21403

Upper-level laundry • Community pool • Two primary suites

(410) 429-7425

COMING SOON

$234,900

2 beds2 baths955 sq ft

204-H Victor Pkwy Unit H, Annapolis, MD 21403

Updated hvac system • Private balcony • Tennis courts

(410) 972-4000

NEW CONSTRUCTION

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Backing to a wooded setting, this beautiful home features 4 bedrooms, 4.5 bathrooms, and a welcoming front porch. The gourmet kitchen boasts quartz countertops, stainless steel appliances, and a chimney-style range hood. Enjoy additional entertaining space in the finished recreation room, complete with a wet bar. Window blinds, washer, and dryer are also included.

$1,199,900

4 beds4.5 baths8,778 sq ft

115 Stilly Way, Annapolis, MD 21403

Quartz countertops • Wet bar • Gourmet kitchen

(410) 979-7740

FLOOR PLAN

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Discover this charming 2-bedroom, 2-bathroom unit located in the desirable Annapolis Overlook community. Built in 1995, this well-maintained garden-style apartment offers a spacious 1,202 square feet of living space, perfect for those seeking comfort and convenience in a suburban setting. Step inside to find a thoughtfully designed interior featuring a combination dining and living area that creates an inviting atmosphere for both relaxation and entertaining. The gourmet kitchen is equipped with modern appliances, including a refrigerator, electric oven/range, microwave, dishwasher, and a washer and dryer for added convenience. The breakfast area is perfect for casual dining, while the fami

$305,000

2 beds2 baths1,202 sq ft

10 Amberstone Ct Unit G, Annapolis, MD 21403

$264 HOA • Parking • Community pool

(410) 429-7425

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Nestled within the serene enclave of Fairwinds of Annapolis, this exquisite penthouse unit offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With 949 square feet of thoughtfully designed living space, this two-bedroom, two-bathroom residence is a sanctuary of tranquility and sophistication. As you step inside, you are greeted by an inviting atmosphere that exudes warmth and elegance. The classic Colonial architectural style, complemented by rich brick construction, creates a timeless appeal that resonates throughout the home. Natural light floods the open living areas, enhancing the spaciousness and inviting you to unwind in style. The heart o

$255,000

2 beds2 baths949 sq ft

203 Victor Pkwy Unit L, Annapolis, MD 21403

Brick construction • Penthouse unit • Indoor pool

(410) 255-3690

ABOUT THIS HOME
Hillsmere Shores, MD Homes for Sale
Welcome home to Fairwinds of Annapolis! * Updates: LVP Flooring 2023, Furnace 2023, Fully Painted 2026 * This spacious three bedroom, two bathroom condo offers the perfect combination of comfort, convenience, and easy living in the heart of Annapolis. Step inside to discover an inviting, light filled living room featuring attractive flooring and plenty of space to relax or entertain. The adjoining dining area provides a wonderful setting for everyday meals or gathering with friends and family. The thoughtfully designed kitchen offers abundant cabinetry, generous counter space, and a functional layout that makes meal preparation a breeze. The spacious primary bedroom provides a comfortable

$269,000

3 beds2 baths1,580 sq ft

21 Silverwood Cir #3, Annapolis, MD 21403

$571 HOA • Community pool • Built 1974

(410) 429-7425

Property at 209 Victor Pkwy Unit 209B, Annapolis, MD 21403, 2 beds, 2 baths

$239,900

2 beds2 baths987 sq ft

209 Victor Pkwy Unit 209B, Annapolis, MD 21403

(443) 632-3000

Property at 996 Headwater Rd, Annapolis, MD 21403, 4 beds, 3.5 baths

$950,000

4 beds3.5 baths2,288 sq ft

996 Headwater Rd, Annapolis, MD 21403

(301) 970-2447

Property at 112 Stilly Way, Annapolis, MD 21403, 4 beds, 4.5 baths

$1,119,290

4 beds4.5 baths8,772 sq ft

112 Stilly Way, Annapolis, MD 21403

(410) 979-7740

Property at 303 Riding Ridge Rd, Annapolis, MD 21403, 4 beds, 2.5 baths

$735,000

4 beds2.5 baths2,238 sq ft

303 Riding Ridge Rd, Annapolis, MD 21403

(410) 260-2800

Property at 20-H Amberstone Ct Unit H, Annapolis, MD 21403, 3 beds, 2 baths

$285,000

3 beds2 baths1,119 sq ft

20-H Amberstone Ct Unit H, Annapolis, MD 21403

(410) 729-7700

Property at 126 Stilly Way, Annapolis, MD 21403, 4 beds, 4.5 baths

$1,160,000

4 beds4.5 baths4,813 sq ft

126 Stilly Way, Annapolis, MD 21403

(410) 280-5600

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

$327,500

3 beds2.5 baths1,694 sq ft

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

(443) 771-8009

Property at 213-F Victor Pkwy Unit 213F, Annapolis, MD 21403, 2 beds, 2 baths

$239,000

2 beds2 baths932 sq ft

213-F Victor Pkwy Unit 213F, Annapolis, MD 21403

(410) 224-3600

Property at 30-I Sandstone Ct, Annapolis, MD 21403, 3 beds, 2 baths

$299,400

3 beds2 baths1,254 sq ft

30-I Sandstone Ct, Annapolis, MD 21403

(240) 737-5000

Property at 1007 Harbor Dr, Annapolis, MD 21403, 4 beds, 4 baths

$800,000

4 beds4 baths3,722 sq ft

1007 Harbor Dr, Annapolis, MD 21403

(410) 266-9005

Property at 50 Sandstone Ct Unit G, Annapolis, MD 21403, 2 beds, 2 baths

$270,000

2 beds2 baths1,010 sq ft

50 Sandstone Ct Unit G, Annapolis, MD 21403

(240) 829-9360

Property at 1 Silverwood Cir #8, Annapolis, MD 21403, 2 beds, 2 baths

$239,000

2 beds2 baths1,312 sq ft

1 Silverwood Cir #8, Annapolis, MD 21403

(410) 972-4000

Property at 8 Georgetown Ct Unit 1-8, Annapolis, MD 21403, 3 beds, 1.5 baths

$299,999

3 beds1.5 baths1,106 sq ft

8 Georgetown Ct Unit 1-8, Annapolis, MD 21403

(443) 318-8800

Property at 10-K Sandstone Ct Unit K, Annapolis, MD 21403, 2 beds, 2 baths

$275,000

2 beds2 baths1,200 sq ft

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

(410) 272-4800

Average home prices near Hillsmere Shores, MD

Cities

Neighborhoods
Zip Codes

Hillsmere Shores, MD real estate trends

All Home Types trends in Hillsmere Shores, MD

Median Sale Price
# of Homes Sold
Median Days on Market

All Home Types

Median Sale Price (All Home Types)

$644,552

+1.9% YoY | Oct 2026

1 year
3 year
5 year

Based on Redfin calculations of home data from MLS and/or public records.

Location

Data

Oct 2026

Growth

% YoY

Hillsmere Shores, MD

$644,552

+1.9%

See more Hillsmere Shores, MD market insights

More to explore in Hillsmere Shores, MD

Featured
Price
Bedroom

How to buy a house in Hillsmere Shores, 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 Hillsmere Shores

337

Deals*

4.8

Satisfaction

3091

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.

Redfin Brokerage Licenses

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.