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Browse All Homewood Properties for Sale
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
Listing courtesy of EXP Realty, LLC. Contact:
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
Listing courtesy of Compass. Contact:
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
Listing courtesy of Real Broker, LLC - Annapolis. Contact:
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
Listing courtesy of TTR Sotheby's International Realty. Contact:
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
Listing courtesy of Compass. Contact:
Selling Office: Compass.
None
- 3 Beds
- 2 Baths
Listing courtesy of EXP Realty, LLC. Contact:
Selling Office: Real Broker, LLC - Annapolis.
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
Listing courtesy of Corner House Realty. Contact:
Selling Office: TTR Sotheby's International Realty.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Berkshire Hathaway HomeServices PenFed Realty.
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
Listing courtesy of RE/MAX Executive. Contact:
Selling Office: May Realty.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: TTR Sotheby's International Realty.
Listed for comp purposes
- 2 Beds
- 1 Baths
Listing courtesy of RE/MAX United Real Estate. Contact:
Selling Office: Keller Williams Flagship.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Engel & Volkers Annapolis.
**Unique Investor Opportunity in Historic Annapolis!** Location! Location! Location! This officially licensed two-unit rental boasts a stellar rental history since 2006...
Listing courtesy of Curtis Real Estate Company. Contact:
Selling Office: Long & Foster Real Estate, Inc..
**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
Listing courtesy of Curtis Real Estate Company. Contact:
Selling Office: Long & Foster Real Estate, Inc..
Open house 10/15 from 11-1!! Beautiful home in sought after community of Homewood is this large 4 bedroom 3.5 bath colonial situated on a corner lot with views of the Nav...
- 4 Beds
- 4 Baths
Listing courtesy of Engel & Volkers Annapolis. Contact:
Selling Office: Canopy Real Estate, LLC..
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Engel & Volkers Annapolis.
!!! 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
Listing courtesy of EXIT Results Realty. Contact:
Selling Office: Coldwell Banker Realty.
Under Contract- Open house is Cancelled for Sunday 3/29. THIS COASTAL RANCH...
- 3 Beds
- 2 Baths
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Monument Sotheby's International Realty.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: TTR Sotheby's International Realty.
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
Listing courtesy of Samson Properties. Contact:
Selling Office: Samson Properties.
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
Listing courtesy of EXP Realty, LLC. Contact:
Selling Office: Coldwell Banker Realty.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Martz and Associates Real Estate LLC.
None
- 4 Beds
- 3 Baths
Listing courtesy of Compass. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: EXP Realty, LLC.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Anne Arundel Properties, Inc..
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: RLAH @properties.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Compass.
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...
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Coldwell Banker Realty.
None
- 4 Beds
- 5 Baths
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: GybeSet Homes.
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...
Listing courtesy of Academy Realty Inc.. Contact:
Selling Office: Engel & Volkers Annapolis.
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Coldwell Banker Realty.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: EXP Realty, LLC.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Samson Properties.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Taylor Properties.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Academy Realty Inc.. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Academy Realty Inc.. Contact:
Selling Office: Non Subscribing Office.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Coldwell Banker Realty.
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
Listing courtesy of Veterans First Realty. Contact:
Selling Office: Keller Williams Flagship.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: EXP Realty, LLC.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Engel & Volkers Annapolis.
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
Listing courtesy of Keller Williams Capital Properties. Contact:
Selling Office: Veterans First Realty.
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Berkshire Hathaway HomeServices PenFed Realty.
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Real Broker, LLC - Annapolis.
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
Listing courtesy of Coldwell Banker Realty. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Long & Foster Real Estate, Inc.. Contact:
Selling Office: Long & Foster Real Estate, Inc..
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
Listing courtesy of Compass. Contact:
Selling Office: Berkshire Hathaway HomeServices PenFed Realty.
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
Listing courtesy of RE/MAX Leading Edge. Contact:
Selling Office: Coldwell Banker Realty.
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
Listing courtesy of Taylor Properties. Contact:
Selling Office: Coldwell Banker Realty.Homewood Real Estate & Homes
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