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Browse All Hillsmere Estates Properties for Sale
Welcome to Hillsmere Shores! This exceptionally well-maintained 4-bedroom, 3-full-bath home has benefited from numerous improvements over the years, including newer mecha...
- 4 Beds
- 3 Baths
- MDAA2160232 MLS
SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 103 Great Lake Drive, an exciting new opportunity in one of Annapolis' most sought-after w...
- 4 Beds
- 3 Baths
- MDAA2159016 MLS
Estate sale - 2 bed 1 bath - needs work
- 2 Beds
- 2 Baths
- MDAA2158458 MLS
Character, comfort, and versatility come together in this beautifully appointed 1,900 sq. ft. Hillsmere home. Set among large, mature trees within an established waterfro...
- 4 Beds
- 3 Baths
- MDAA2158198 MLS
- Hillsmere Estates Bldg.
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 communi...
- 3 Beds
- 3 Baths
- MDAA2157998 MLS
Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfron...
- 4 Beds
- 3 Baths
- MDAA2157350 MLS
Rarely available, all-brick rancher in the amenity-rich, sought-after Hillsmere Shores community. This home has been meticulously cared for and loved, and it will show fr...
- 3 Beds
- 2 Baths
- MDAA2155652 MLS
Welcome to Hillsmere Shores, one of Annapolis' premier waterfront communities, where coastal living meets convenience and an active lifestyle. This beautifully maintained...
- 3 Beds
- 3 Baths
- MDAA2154406 MLS
Welcome to 109 Sunset Drive, a beautifully fully renovated 4-bedroom, 3-full-bath home offering Luxury finishes & approximately 2,500 finished square feet in the highly ...
- 4 Beds
- 3 Baths
- MDAA2153934 MLS
This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and pa...
- 4 Beds
- 3 Baths
- MDAA2152396 MLS
There's a reason people fall in love with Hillsmere. And at 104 Groh Lane, there's even more to love. Nestled within one of Annapolis' most treasured waterfront communit...
- 4 Beds
- 3 Baths
- MDAA2150374 MLS
** Rare Mid-Century Modern Waterfront Sanctuary on Bay View Drive ** Welcome to 129 E Bay View Drive, an authentic 1954 mid-century modern masterpiece offering a rare com...
- 3 Beds
- 3 Baths
- MDAA2149802 MLS
A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! This home qualifies for zero downpayment financing through FHA Solar + Loan! 410 Walnut Road presents a rar...
- 3 Beds
- 1 Baths
- MDAA2149406 MLS
New price! Welcome to 108 Maple Drive, a beautifully updated rancher in the sought-after waterfront community of Hillsmere Shores. Renovated throughout in 2016, this move...
- 3 Beds
- 3 Baths
- MDAA2149008 MLS
Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis...
- 4 Beds
- 2 Baths
- MDAA2146848 MLS
Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along pictu...
- 4 Beds
- 3 Baths
- MDAA2146462 MLS
Welcome to this amazing home in sought after Hillsmere Estates, where you will always have a beautiful water view of the Chesapeake Bay! The owners have spared no expense...
- 4 Beds
- 3 Baths
- MDAA2143130 MLS
Absolutely transformed with a recently completed interior remodel this stunning contemporary home boasts panoramic water views across Lake Hillsmere and out to the South ...
- 5 Beds
- 5 Baths
- MDAA2134744 MLS
520 Harbor Drive isn’t simply another home hitting the market — it’s the opportunity buyers spend months waiting to find in Hillsmere and rarely secure. Perfectly positio...
- 4 Beds
- 3 Baths
- MDAA2142262 MLS
Welcome to 107 Lake View Drive — a stunning, fully renovated retreat tucked inside one of Annapolis's most coveted waterfront neighborhoods. Nestled in the heart of Hills...
- 4 Beds
- 4 Baths
- MDAA2141842 MLS
Nestled on a generous .30-acre corner lot, this charming single-family residence resides just a mere half mile from the private community beach! Upon entry, you're welco...
- 3 Beds
- 2 Baths
- MDAA2081982 MLS
Beautiful 4 Bedroom 2 Full Bath Just Blocks From The Water in Hillsmere Shores. This One Checks All The Boxes and Is Perfect for Indoor and Outdoor Entertaining. Home Gre...
- 4 Beds
- 2 Baths
- MDAA2079906 MLS
- Hillsmere Estates Bldg.
Fully remodeled raised rancher w/ 1 car garage in the highly coveted water privileged community of Hillsmere. The owners have meticulously maintained and perfectly update...
- 3 Beds
- 2 Baths
- MDAA2079008 MLS
- Hillsmere Shores Bldg.
**OFFER DEADLINE MONDAY, 2/19 AT 5PM** WELCOME TO YOUR NEW HOME IN SOUGHT-AFTER HILLSMERE! Get ready to fall in love with this 4 bedroom, 3 full bath Annapolis home, jus...
- 4 Beds
- 3 Baths
- MDAA2077290 MLS
Update Property Description: PRICE REDUCED FOR FINAL TIME. LAST OPEN HOUSE THIS WEEKEND, March 2-3HOUSE WILL GO UP FOR RENT(WITH OPTION),MONDAY, March 4th Property 309 Hi...
- 4 Beds
- 3 Baths
- MDAA2076432 MLS
This charming 4 bedroom, 2 full bath home in the sought-after neighborhood of Hillsmere, just minutes from the shops and restaurants in Eastport and Downtown Annapolis, o...
- 4 Beds
- 2 Baths
- MDAA2074152 MLS
Welcome to this fabulous find in Hillsmere Estates. This is the perfect oasis after a long day complete with a beautiful water view and a tree canopied yard. The perfec...
- 4 Beds
- 3 Baths
- MDAA2073718 MLS
**Price Reduced! Priced to Sell!** This Spacious and Meticulously Maintained 3 Bedroom 2 Bath Rambler is ready for your finishing touches. Nothing to do besides make thi...
- 3 Beds
- 2 Baths
- MDAA2072046 MLS
Fantastic opportunity for Buyers in great water oriented community off the South River! Located within walking distance to school, Pal Park & Quiet Waters Park, and the ...
- 2 Beds
- 1 Baths
- MDAA2070618 MLS
Welcome to this charming 3-bedroom home nestled in amenity-filled Hillsmere! Boasting a serene and inviting atmosphere, this residence offers a comfortable and modern li...
- 3 Beds
- 3 Baths
- MDAA2070196 MLS
- Hillsmere Bldg.
Don’t miss this great opportunity to own this split foyer home in the beautiful water access community of Hillsmere Estates. Put your special touches on this three bedro...
- 3 Beds
- 3 Baths
- MDAA2069884 MLS
Extraordinary mid-century modern waterfront home in coveted Hillsmere Estates community in Annapolis and this home is located just steps from the private entrance into Qu...
- 3 Beds
- 3 Baths
- MDAA2069724 MLS
Don’t miss this exceptionally maintained and updated split foyer in sought after Hillsmere! A large bay window in the living room offers loads of natural light, and th...
- 4 Beds
- 3 Baths
- MDAA2065366 MLS
Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conven...
- 2 Beds
- MDAA2141166 MLS
YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the g...
- 4 Beds
- 3 Baths
- MDAA2140304 MLS
Welcome to 600 Tayman Drive, where timeless Colonial charm meets the easy, coastal lifestyle that defines this sought-after Annapolis waterfront community. From the momen...
- 4 Beds
- 3 Baths
- MDAA2139516 MLS
Situated on the South River with sweeping water views all the way to the Chesapeake Bay, this Nantucket-inspired waterfront home presents a rare opportunity to create som...
- 6 Beds
- 4 Baths
- MDAA2139274 MLS
UNDER CONTRACT - ACCEPTING BACKUPS!!!! Nestled in the charming Hillsmere Estates, this home is on an oversize large corner lot. **BRAND NEW** Roof. Small storage/work...
- 3 Beds
- 3 Baths
- MDAA2136690 MLS
Turn-key and beautifully appointed, this 5-bedroom, 3 full bath home sits on a generous 0.27-acre lot in the highly sought-after Hillsmere Estates community. A long drive...
- 5 Beds
- 3 Baths
- MDAA2136450 MLS
Life in Hillsmere revolves around the water — the Chesapeake Bay, the South River, and a lifestyle that most people only experience on vacation. Welcome to 298 Edgemere ...
- 5 Beds
- 3 Baths
- MDAA2136726 MLS
Welcome to 117 Gardner Drive, a beautifully renovated home nestled in the coveted water-privileged community of Hillsmere Shores. Situated on an exceptional lot, this tur...
- 5 Beds
- 3 Baths
- MDAA2134032 MLS
Priced with opportunity in mind, this Hillsmere ranch offers a home with good bones and a flexible layout, presenting an excellent chance for buyers to build equity and m...
- 3 Beds
- 2 Baths
- MDAA2134670 MLS
Welcome home to Holly Drive and the quiet rhythms of coastal Annapolis living. Some homes are defined by their rooms. 403 Holly Drive is shaped by everyday beauty - soft...
- 4 Beds
- 4 Baths
- MDAA2135234 MLS
SOLD AND SETTLED SITE UNSEEN WITH MULTIPLE OFFERS ... LISTED AND SOLD SIMLOUTANELOUSY ... GREAT BONES, FIXER UPPER
- 4 Beds
- 2 Baths
- MDAA2135236 MLS
New Construction
- 4 Beds
- 4 Baths
- MDAA2134544 MLS
Welcome to 123 Spruce Lane, a completely renovated home in the sought-after waterfront community of Hillsmere Shores—where every detail has been thoughtfully redesigned t...
- 4 Beds
- 4 Baths
- MDAA2134504 MLS
Welcome to 520 Harbor Drive, where Annapolis lifestyle meets coastal charm in the heart of the Hillsmere community. This completely remodeled rancher by the well-known bu...
- 4 Beds
- 3 Baths
- MDAA2091278 MLS
Welcome to 303 Edgemere Drive, an enchanting south-facing residence in the coveted Hillsmere community of Annapolis. This home masterfully combines contemporary elegance ...
- 4 Beds
- 3 Baths
- MDAA2089680 MLS
(Professional photos coming soon). Explore the charm of 308 Beach Drive, where your ideal home awaits! Nestled in the heart of the sought-after Hillsmere Estates, this Co...
- 4 Beds
- 3 Baths
- MDAA2076564 MLS
Discover the allure of 102 Pine Drive, where your dream home is poised to embrace you! Nestled in the heart of the highly coveted Hillsmere Estates, this Rancher-style ge...
- 3 Beds
- 2 Baths
- MDAA2072150 MLS
Hillsmere Estates Real Estate & Homes
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