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Luxury New Construction | A Lifestyle of Walkability, Elegance & Annapolis Charm. Don’t miss this exceptional opportunity to own a stunning new-construction home in the h...
- 4 Beds
- 4 Baths
- MDAA2159556 MLS
Charming Homewood cottage with numerous recent updates! This property is located on a partially secluded lot bordering city-owned, undevelopable land encompassing the hea...
- 2 Beds
- 1 Baths
- MDAA2159126 MLS
NEWLY UPDATED! NEW BATHROOMS, GARAGE, and A BONUS 3rd FLOOR ROOM. Boasting 1,670 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized...
- 3 Beds
- 2 Baths
- MDAA2157812 MLS
Tucked into Homewood, just beyond the brick sidewalks of Historic Downtown Annapolis, 16 Woodlawn Avenue is a residence taken down to the studs and rebuilt in 2019, blend...
- 3 Beds
- 3 Baths
- MDAA2154556 MLS
Some homes simply have a soul—and this is one of them. For more than 100 years, this impeccably maintained Annapolis treasure has been the backdrop for holidays, celebrat...
- 3 Beds
- 2 Baths
- MDAA2151766 MLS
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- 3 Beds
- 2 Baths
- MDAA2150910 MLS
Welcome to 307 Glen Ave, a charming cedar shake home in the heart of Annapolis's highly sought after Homewood community. Originally built in 1901 and thoughtfully renovat...
- 3 Beds
- 3 Baths
- MDAA2149470 MLS
HOMEWOOD/ANNAPOLIS in-town living at its finest—this charming and thoughtfully updated 1930s Foursquare colonial style home, with 1,620 total sq ft, offers a rare blend o...
- 2 Beds
- 2 Baths
- MDAA2145152 MLS
Just in time for Commissioning Week — walk to Navy-Marine Corps Memorial Stadium from this beautifully renovated Annapolis home that perfectly blends historic charm with ...
- 4 Beds
- 4 Baths
- MDAA2144946 MLS
Classic 1936 Foursquare reimagined with a thoughtfully designed addition by award-winning Studio 3 Architecture in sought-after Homewood. The architecture blends modern e...
- 4 Beds
- 4 Baths
- MDAA2143406 MLS
Listed for comp purposes
- 2 Beds
- 1 Baths
- MDAA2142850 MLS
This classic craftsman sits on a quiet corner of the desirable Homewood neighborhood, known for its tree-lined streets and easy access to downtown Annapolis. The stone a...
- 4 Beds
- 4 Baths
- MDAA2141492 MLS
**Unique Investor Opportunity in Historic Annapolis!** Location! Location! Location! This officially licensed two-unit rental boasts a stellar rental history since 2006...
- MDAA2072306 MLS
**Unique Investor Opportunity in Historic Annapolis!** Location! Location! Location! This officially licensed two-unit rental boasts a stellar rental history since 2006...
- 2 Beds
- 2 Baths
- MDAA2072292 MLS
Introducing 211 South Cherry Grove - a beautiful 5 bed/2.5 bath Cape Cod home in the heart of the charming Homewood community in Annapolis, Maryland! This spacious and in...
- 5 Beds
- 3 Baths
- MDAA2071162 MLS
!!! Back on the market, buyers got cold feet. !!! Home appraisal came back at $735k, bring your clients back through! Welcome Home...Nestled within the heart of Historic...
- 3 Beds
- 2 Baths
- MDAA2071024 MLS
Under Contract- Open house is Cancelled for Sunday 3/29. THIS COASTAL RANCH...
- 3 Beds
- 2 Baths
- MDAA2139724 MLS
Welcome to 202 Glen Ave, ideally situated in Annapolis’ sought-after Homewood neighborhood just minutes from Historic Downtown and West Annapolis. This beautifully maint...
- 3 Beds
- 4 Baths
- MDAA2138954 MLS
Located on one of the most desirable streets in Homewood, this classic four-square home offers timeless character and an exceptional Annapolis lifestyle. Just a short wal...
- 3 Beds
- 2 Baths
- MDAA2139062 MLS
Welcome to this charming Cape Cod on a desirable corner lot the highly sought-after Homewood neighborhood of Annapolis, where classic character meets modern comfort and c...
- 3 Beds
- 3 Baths
- MDAA2138870 MLS
BEST AND FINAL DUE MONDAY 3/16/2026 AT NOON! SUNDAY 3/15 from 12-2pm! This classic Craftsman sits on a quiet, spacious street in Homewood, directly facing the open fields...
- 4 Beds
- 2 Baths
- MDAA2137614 MLS
Beautifully updated Homewood residence with thoughtful improvements throughout. The backyard has been completely reimagined with new landscaping and plantings, creating a...
- 5 Beds
- 4 Baths
- MDAA2135764 MLS
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- 4 Beds
- 3 Baths
- MDAA2135652 MLS
Charming Cape Cod in sought-after Homewood, offering newly refinished hardwood floors throughout, a thoughtful layout, and inviting indoor and outdoor living spaces. The ...
- 3 Beds
- 2 Baths
- MDAA2134562 MLS
Tucked away at the end of a quiet, secluded street off No Cherry Grove (one of the prettiest streets in sought after Homewood) is the home you have been waiting for! Thi...
- 4 Beds
- 3 Baths
- MDAA2134282 MLS
Classic Cape Cod in Homewood with standout curb appeal, offering a timeless look straight out of a favorite home-inspo Instagram moment. A welcoming front porch sets the ...
- 3 Beds
- 3 Baths
- MDAA2133664 MLS
Welcome to a picture-perfect, expanded Cape Cod in Homewood! Situated just around the corner from Downtown Annapolis and the Navy Stadium, this home offers approximately ...
- 3 Beds
- 2 Baths
- MDAA2081110 MLS
RARE OPPORTUNITY TO BUILD YOUR ANNAPOLIS DREAM HOME IN HOMEWOOD. NESTLED IN BETWEEN MCGUCKIAN AND VIRGINIA STREETS, THIS .20 ACRE LOT IS A PRIME LOCATION TO BUILD. LOT I...
- MDAA2069552 MLS
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- 4 Beds
- 5 Baths
- MDAA2054946 MLS
Rare multi-family opportunity in the highly desirable Homewood community of Annapolis! This offering includes both 913 and 915 Ridgewood, being sold together for the list...
- MDAA2132682 MLS
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...
- 4 Beds
- 2 Baths
- MDAA2131908 MLS
Discover this enchanting 2 BR, 3 level Gingerbread Cottage in the heart of popular Homewood! A rare Sears 1929 kit home, it has been lovingly restored to showcase its his...
- 2 Beds
- 2 Baths
- MDAA2131228 MLS
Historic and Charming 2200+ft, 4 level 3 bedroom/3 full bath home. Hardwood floors, freshly painted. Kitchen with quartz countertops, stainless steel appliances, recessed...
- 3 Beds
- 3 Baths
- MDAA2130724 MLS
Brand-New in Homewood! Perfect layout with a front sitting room or office, and a spacious family room that opens to an extra-large, flat backyard — fully fenced with a g...
- 5 Beds
- 4 Baths
- MDAA2129520 MLS
CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL NANTUCKET CAPE COD IN THE HEART OF HOMEWOOD! THIS ADORABLE HOME TRANSFERS YOU BACK TO THE ISLAND OF MARTHA'S VINEYARD OR NANT...
- 3 Beds
- 2 Baths
- MDAA2128002 MLS
Opportunity knocks in the heart of Annapolis! This 4-bedroom, 2.5-bath home sits on a large corner lot in one of the city's most sought-after communities. While the home ...
- 4 Beds
- 3 Baths
- MDAA2121766 MLS
Rare opportunity in Homewood of Annapolis! On an oversized lot in one of the city's most sought-after neighborhoods, this 3-bedroom, 2-bathroom offers extra space for out...
- 3 Beds
- 2 Baths
- MDAA2121600 MLS
Meander off the beaten path, also known as Poplar Trail, and you will find yourself at a sweet little house with a purple door in Homewood. This is 23 Linden Avenue, also...
- 3 Beds
- 3 Baths
- MDAA2115226 MLS
Don't miss your chance to purchase this charming 3 bedroom, 1.5 bath home in the highly coveted neighborhood of Homewood. This home has been lovingly lived in and provide...
- 3 Beds
- 2 Baths
- MDAA2111578 MLS
This warm and inviting home features an open gourmet kitchen that leads to a large deck and a fully fenced backyard. The main level boasts a spacious living room, dining ...
- 5 Beds
- 4 Baths
- MDAA2103962 MLS
Fantastic location and vintage charm await at 18 Woodlawn Avenue in the coveted neighborhood of Homewood. If walkability to all of downtown Annapolis is what you seek, t...
- 3 Beds
- 2 Baths
- MDAA2101158 MLS
This property is a dream for both investors and families alike. Completely gutted and restored with all-new finishes in 2023, this colonial home is situated in the highly...
- 4 Beds
- 4 Baths
- MDAA2108422 MLS
Nestled in the heart of Homewood, on one of the prettiest streets in the neighborhood, this light-filled charming 5 bedroom, 4 bathroom home in Annapolis is just a short ...
- 5 Beds
- 4 Baths
- MDAA2110426 MLS
Enchanting Annapolis Cape Cod! Old world charm is found throughout this 3 bedroom, 1.5 bath home. Large living room with wood burning fireplace and built-ins. Hardwood fl...
- 3 Beds
- 2 Baths
- MDAA2109966 MLS
Nestled on one of Annapolis’ most beautiful Avenues, this meticulously maintained charming four-bedroom, 2.5-bath home is a rare find. Set on a private, fenced .46-acre l...
- 4 Beds
- 3 Baths
- MDAA2102804 MLS
Tucked away in the sought-after neighborhood of Homewood, this charming cottage blends character and charm within a functional living space, just steps from the US Naval ...
- 3 Beds
- 2 Baths
- MDAA2096866 MLS
Looking for delightful charm and character, yet an updated home in Homewood? Look no further! This immaculate 5-bedroom, 3-bath home is making its debut in Annapolis! Up...
- 5 Beds
- 3 Baths
- MDAA2091362 MLS
Welcome to an unparalleled living experience in the coveted Homewood community, renowned for its proximity to Historic Annapolis—an iconic city celebrated as the unoffici...
- 3 Beds
- 3 Baths
- MDAA2090258 MLS
Meticulously maintained. Stunning. Charming. This spacious four bedroom, 2.5 bath home in the Homewood community of Annapolis is one you do not want to miss. Located wi...
- 4 Beds
- 3 Baths
- MDAA2085854 MLS
It is all about the charm and location of this beautiful 3 Bedroom 2 Bath Cottage in the heart of Annapolis. Located in sought after Homewood on a beautiful quiet residen...
- 3 Beds
- 2 Baths
- MDAA2079898 MLS
Homewood Real Estate & Homes
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