The Roskelly Team at Berkshire Hathaway HomeServices
  • Home
  • Featured
  • Relocation
  • Buy
  • Sell
  • Rent
  • Market Report
  • Team
  • Blog
Login
410-721-6694

Sign in to your account

Need to reset your phone number?

Don't have an account with us?

Click here to sign up.

Quick Annapolis MD MLS Search

TO
Advanced Search

Address Search

Browse All Hillsmere Shores Properties for Sale

282 Cedar Ln, Annapolis image
282 Cedar Ln, Annapolis $531,000

**OFFER DEADLINE MONDAY 8/10 @ 12 NOON** Welcome to 282 Cedar Lane, a beautifully updated rancher nestled in one of Annapolis' most sought-after waterfront communities. T...

  • 3 Beds
  • 2 Baths
  • MDAA2152448 MLS
117 Sunset Dr, Annapolis image
117 Sunset Dr, Annapolis $885,000

Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores communit...

  • 3 Beds
  • 3 Baths
  • MDAA2150956 MLS
529 Lee Cir, Annapolis image
529 Lee Cir, Annapolis $2,615,000

Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributari...

  • 6 Beds
  • 6 Baths
  • MDAA2150742 MLS
621 Harbor Dr, Annapolis image
621 Harbor Dr, Annapolis $1,450,000

Sunsets, Water Views & Effortless Coastal Living in Hillsmere Perfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathta...

  • 5 Beds
  • 4 Baths
  • MDAA2149706 MLS
278 Hillsmere Dr, Annapolis image
278 Hillsmere Dr, Annapolis $749,000 ▼

Don't miss out on this great location. Fall is here and it is time to make your move and be settled in before the holiday season is here! Must see inside to appreciate al...

  • 4 Beds
  • 3 Baths
  • MDAA2149064 MLS
129 Meade Dr, Annapolis image
129 Meade Dr, Annapolis $585,000

OPEN SATURDAY, 6/6, 10AM-12PM and SUNDAY, 6/7, 12-2PM Nestled in one of Annapolis's most beloved water-oriented communities, this 4-bedroom, 2 full bath home offers the ...

  • 4 Beds
  • 2 Baths
  • MDAA2147594 MLS
406 Holly Dr, Annapolis image
406 Holly Dr, Annapolis $420,000

Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amen...

  • 3 Beds
  • 2 Baths
  • MDAA2147188 MLS
105 Mansion Dr, Annapolis image
105 Mansion Dr, Annapolis $625,000

Open House on 5/31/26 has been cancelled. Multiple offers received. Charming two-bedroom rancher with all the right updates! Remodeled kitchen (2020) features a pantry ...

  • 2 Beds
  • 1 Baths
  • MDAA2145092 MLS
110 Kuethe Dr, Annapolis image
110 Kuethe Dr, Annapolis $689,900

An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh pai...

  • 4 Beds
  • 4 Baths
  • MDAA2144216 MLS
property image
417 Holly Dr, Annapolis $470,000

None

  • 4 Beds
  • 3 Baths
  • MDAA2075456 MLS
property image
124 Spruce Ln, Annapolis $557,500

Welcome to this charming 4-bedroom, 2-full bath home nestled in the heart of the water-oriented community of Hillsmere! Upon entering, you are greeted by a spacious and ...

  • 4 Beds
  • 2 Baths
  • MDAA2073912 MLS
property image
101 Steffey Dr, Annapolis $650,000

Large 4 Bedroom 4 Full Bathroom home in the Hillsmere Community with over 2,700 finished square feet. Includes a private connected fully functional one bedroom in-law su...

  • 4 Beds
  • 4 Baths
  • MDAA2064348 MLS
122 E Bay View Dr, Annapolis image
122 E Bay View Dr, Annapolis $1,030,000

Welcome to 122 E Bay View Drive in sought-after Hillsmere—where lifestyle and comfort come together just minutes from downtown Annapolis. Ideally located just steps from ...

  • 3 Beds
  • 3 Baths
  • MDAA2141130 MLS
115 Edgemere Dr, Annapolis image
115 Edgemere Dr, Annapolis $655,000

Offer deadline of 6pm Sunday 3/22/2026. The main level greets you with rich hardwood floors flowing throughout, three well-appointed bedrooms, and an upgraded full bath....

  • 4 Beds
  • 2 Baths
  • MDAA2139246 MLS
108 Huse Dr, Annapolis image
108 Huse Dr, Annapolis $825,000

Offer Received, Seller respectfully requests best and final offers be submitted by 12 PM, Monday, February 23. Welcoming rancher in water-privileged Hillsmere Shores, se...

  • 3 Beds
  • 2 Baths
  • MDAA2134092 MLS
property image
310 Cedar Ln, Annapolis $525,000

Welcome home to Hillsmere and this beautifully renovated Cape Cod!! Walking through the front door into the welcoming living room and you will immediately feel right at...

  • 3 Beds
  • 2 Baths
  • MDAA2074604 MLS
150 E Bay View Dr, Annapolis image
150 E Bay View Dr, Annapolis $997,300

Set in the sought-after Hillsmere neighborhood of Annapolis, this 2,200-square-foot rancher offers a calm, coastal feel enhanced by a single serene water view and a long ...

  • 3 Beds
  • 2 Baths
  • MDAA2132256 MLS
129 Pinecrest Dr, Annapolis image
129 Pinecrest Dr, Annapolis $450,000

Welcome to this split-level 4-bedroom, 2.5-bath home in the desirable, water-privileged community of Hillsmere Shores. The home has solid bones and has been consistently ...

  • 4 Beds
  • 3 Baths
  • MDAA2131730 MLS
161 E Bay View Dr, Annapolis image
161 E Bay View Dr, Annapolis $925,000

Welcome home to this fantastic contemporary style where coastal charm meets modern connivence only blocks from the sandy beach. Located in water amenity rich Hillsmere Sh...

  • 4 Beds
  • 4 Baths
  • MDAA2130548 MLS
98 Pine Dr, Annapolis image
98 Pine Dr, Annapolis $570,000

Coming soon in water priveledged community on the South River! Well maintained ranch style home on large corner lot, with fenced yard, oversized 2 car garage addition, e...

  • 3 Beds
  • 2 Baths
  • MDAA2128804 MLS
98 Carroll Dr, Annapolis image
98 Carroll Dr, Annapolis $410,000

Welcome to 98 Carroll Drive, a charming single-level home in the sought-after Hillsmere Shores community of Annapolis. This 2-bedroom, 1-bath property sits on a fenced co...

  • 2 Beds
  • 1 Baths
  • MDAA2126692 MLS
100 Sunset Dr, Annapolis image
100 Sunset Dr, Annapolis $995,000

Welcome to your coastal dream home! Perfectly positioned just one block from the community beach and tucked away on a quiet street, this beautifully updated 4-bedroom, 3-...

  • 4 Beds
  • 3 Baths
  • MDAA2126016 MLS
289 Hillsmere Dr, Annapolis image
289 Hillsmere Dr, Annapolis $495,000

Big Reduction of $24,000! Start your new year off in this 3-bedroom, 1-bath home situated on a spacious lot in the desirable, water-privileged community of Hillsmere Sho...

  • 3 Beds
  • 1 Baths
  • MDAA2124400 MLS
132 Pinecrest Dr, Annapolis image
132 Pinecrest Dr, Annapolis $620,000

Come experience the “land of pleasant living” in this charming 4-bedroom, 2-bath Cape Cod in Hillsmere Shores. Enjoy outdoor living on the wraparound covered porch, scree...

  • 4 Beds
  • 2 Baths
  • MDAA2123504 MLS
84 Great Lake Dr, Annapolis image
84 Great Lake Dr, Annapolis $555,000

NEW Price! Enjoy all that this water- privileged community has to offer. This 4 BR home has been freshly painted and is ready to move into. Located just a few blocks f...

  • 4 Beds
  • 2 Baths
  • MDAA2122680 MLS
527 Lee Cir, Annapolis image
527 Lee Cir, Annapolis $1,250,000

Tucked away at the end of a quiet cul-de-sac, this stylish home offers a private pier for your boat plus a floating dock for kayaks, paddleboards, and crabbing—the ideal ...

  • 4 Beds
  • 4 Baths
  • MDAA2120906 MLS
512 Tayman Dr, Annapolis image
512 Tayman Dr, Annapolis $805,000

Welcome to 512 Tayman Drive - a beautifully renovated home tucked away in the water-privileged community of Hillsmere Shores. The moment you step inside you are greeted ...

  • 4 Beds
  • 3 Baths
  • MDAA2112798 MLS
105 Huse Dr, Annapolis image
105 Huse Dr, Annapolis $750,000

🏡 NEWLY UPDATED & MOVE-IN READY! Step into timeless elegance with this beautifully renovated 5-bedroom, 4-bathroom home, where modern upgrades meet classic charm. Every ...

  • 5 Beds
  • 4 Baths
  • MDAA2105456 MLS
611 Harbor Dr, Annapolis image
611 Harbor Dr, Annapolis $855,000

Wow- Fabulous Water View home in Hillsmere! Where else can you find a 6 BR 3 Full bath home on 1/3 acre with over 3000 sq ft? From your first step inside you will find ...

  • 6 Beds
  • 3 Baths
  • MDAA2097286 MLS
410 Holly Dr, Annapolis image
410 Holly Dr, Annapolis $640,000

HILLSMERE! Welcome to this inviting 3-level contemporary home! From the welcoming front porch to the updated interiors and fantastic outdoor spaces, this home is sure to ...

  • 3 Beds
  • 3 Baths
  • MDAA2097440 MLS
518 Beach Dr, Annapolis image
518 Beach Dr, Annapolis $1,175,000

Victorian Elegance Meets Coastal Charm in Annapolis! Experience timeless beauty and modern comfort at this extraordinary custom home in the highly sought-after waterfront...

  • 5 Beds
  • 3 Baths
  • MDAA2098946 MLS
110 Green Spring Dr, Annapolis image
110 Green Spring Dr, Annapolis $600,000

This lovely raised ranch cottage in Hillsmere Shores is ready for you! Located on a 10,000 SF, fenced, flat lot just a block from the community beach, this home is in an ...

  • 5 Beds
  • 2 Baths
  • MDAA2096304 MLS
129 Boyd Dr, Annapolis image
129 Boyd Dr, Annapolis $1,150,000

Welcome to this stunning 5-bedroom, 4-bath water-oriented home in the desirable Hillsmere community. This beautifully updated residence features an updated kitchen with s...

  • 5 Beds
  • 4 Baths
  • MDAA2095772 MLS
111 Boyd Dr, Annapolis image
111 Boyd Dr, Annapolis $557,500

Location, location, location! Nestled in the highly sought-after, water-privileged community of Hillsmere, this 2-bedroom, 2 full bath home boasts the perfect blend of c...

  • 2 Beds
  • 2 Baths
  • MDAA2098162 MLS
105 Hillsmere Ct, Annapolis image
105 Hillsmere Ct, Annapolis $800,000

Welcome home to 105 Hillsmere Court! Relax on your tranquil front porch. Main level home office/library with floor to ceiling built-in bookshelves! Eat-in kitchen with ce...

  • 4 Beds
  • 4 Baths
  • MDAA2088474 MLS
400 Hillsmere Dr, Annapolis image
400 Hillsmere Dr, Annapolis $620,000

Welcome to this immaculate two-story residence nestled in the highly sought-after beach community of Hillsmere. Situated on a tranquil, park-like corner lot, this spacio...

  • 3 Beds
  • 3 Baths
  • MDAA2091144 MLS
611 Tayman Dr, Annapolis image
611 Tayman Dr, Annapolis $568,000

Introducing 611 Tayman Dr. This 4 bedroom, 3 full bath colonial in the coveted neighborhood of Hillsmere Shores screams potential and is ready for it's next adventure. ...

  • 4 Beds
  • 3 Baths
  • MDAA2090256 MLS
109 Boyd Dr, Annapolis image
109 Boyd Dr, Annapolis $539,000

Cute as a button rancher in sought-after water-privileged community of Hillsmere Shores. Just 2 blocks to the water, this 3 bedroom, 2 bath home offers recently refinish...

  • 3 Beds
  • 2 Baths
  • MDAA2089350 MLS
131 Groh Ln, Annapolis image
131 Groh Ln, Annapolis $550,000

Great home in water oriented community, where the South River meets the Bay! 3 Bedroom and two full baths. Beautiful lot with large backyard for family fun. Dreamy sc...

  • 3 Beds
  • 2 Baths
  • MDAA2088392 MLS
416 Edgemere Dr, Annapolis image
416 Edgemere Dr, Annapolis $615,000

Seller accepted a contract so there will not be an open house Sunday 4/14. Welcome to 416 Edgemere Drive in water privileged Hillsmere Shores. This 4 bedroom, 2 bath ho...

  • 4 Beds
  • 2 Baths
  • MDAA2080864 MLS
property image
913 Old Annapolis Neck Rd, Annapolis $625,000

Beautifully updated colonial on just under a half acre and minutes from the water with no HOA!! Home features 3 bedrooms, 2 freshly redone full baths, and one updated b...

  • 3 Beds
  • 3 Baths
  • MDAA2072826 MLS
503 Beach Dr, Annapolis image
503 Beach Dr, Annapolis $498,000

Welcome to 503 Beach Drive, an well maintained 3-bedroom, 1-bath home located in the sought-after community of Hillsmere Shores in Annapolis. This charming property offer...

  • 3 Beds
  • 1 Baths
  • MDAA2118056 MLS
404 Beach Dr, Annapolis image
404 Beach Dr, Annapolis $665,000

Move-in ready ! 404 Beach Drive is a warm and inviting gracious home nestled in the beautiful Hillsmere Estates/Hillsmere Shores water privileged community offering acces...

  • 3 Beds
  • 3 Baths
  • MDAA2103872 MLS

Hillsmere Shores Real Estate & Homes

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Hillsmere Shores, Annapolis MD. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Like or Share

Address Search

Annapolis Communities

  • Admiral Heights
  • Annapolis
  • Annapolis Cove
  • Annapolis Roads
  • Arundel on the Bay
  • Atlantis
  • Bay Highlands
  • Bay Ridge Area
  • Beechwood on the Burley
  • Cape St. Claire
  • Cape St. John
  • Colony Hills
  • Corbin Park
  • Eastport
  • Epping Forest
  • Georgetown Cove
  • Greenwood Acres
  • Heritage Harbour
  • Hillsmere Estates
  • Homewood
  • Hunt Meadow
  • Murray Hill
  • Oyster Harbor
  • Primrose Acres
  • Revell Downs
  • Rolling Knolls
  • Scotts Crossing
  • St. Margarets
  • Truxton Heights
  • Victor Haven
  • Wilshire
  • Walnut Heights & Ridge

Annapolis Waterfront Homes

  • $100,000 - $500,000
  • $500,000 - $1,000,000
  • $1,000,000 - $2,000,000
  • $2,000,001 - $3,000,000
  • $3,000,000 +

Annapolis Historic Homes

Annapolis 55+ communities

  • Baywoods of Annapolis
  • Broad Creek Condo
  • Four Seasons at St. Margarets
  • Heritage Harbour
  • Highland Woods
  • Magothy Meadows

Annapolis Condominiums

Annapolis Homes by Price Range

  • $100,000 - $250,000
  • $250,000 - $350,000
  • $350,000 - $400,000
  • $450,000 - $550,000
  • $550,000 - $650,000
  • $650,000 - $750,000
  • $750,000 - $1,000,000
  • $1,000,000 +
  • Home
  • Advanced Search
  • Selling
  • Buying
  • About Us
  • Contact Us

The Roskelly Team - Fort Meade & Odenton Real Estate Specialists
565 Benfield Road
Severna Park, MD 21146

410-721-6694      Team Office
410-507-2495      Laura Roskelly Mobile
443-623-4523      Jessica Hood, Team Leader Mobile

Like us on Facebook!

E-Mail Us: Hello@TheRoskellyTeam.com



© 2024 - All Rights Reserved - Privacy Policy

 

©2024 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity. 

  • Annapolis
  • Arnold
  • Baltimore
  • Brooklyn Park
  • Churchton
  • Crofton
  • Crownsville
  • Davidsonville
  • Deale
  • Dunkirk
  • Edgewater
  • Gambrills
  • Gibson Island
  • Glen Burnie
  • Greenland Beach
  • Hanover
  • Harwood
  • Jessup
  • Laurel
  • Linthicum
  • Linthicum Heights
  • Lothian
  • Millersville
  • Odenton
  • Pasadena
  • Severn
  • Severna Park
  • Bowie
  • Columbia
  • Curtis Bay
  • Elkridge
  • Ellicott City
  • Fort Meade
  • Fulton
  • Galesville
  • Highland
  • Mayo
  • Anne Arundel County
  • Autumn Crest
  • Autumn Ridge
  • Blue Ridge
  • Carriage Pines
  • Cedar Ridge
  • Chapman Farm
  • Courts of Crofton
  • Crofton Commons
  • Crofton Park
  • Friendship
  • Howard County
  • Parkside
  • Prince Georges County
  • Quail Run
  • Saddlebrook
  • Shamrock Manor
  • Sunrise Beach
  • Tanyard Springs
  • The Knolls
  • Crofton Highlands
  • Crofton Village
  • Fourwinds
  • Lake Shore
  • Maple Ridge
  • Piney Orchard
  • Ridgefield
  • Russett
  • Seven Oaks
IDX Real Estate Websites by
• Accessibility • Terms • Privacy