Address	Bed / Bath	Listing Price
120 CHESAPEAKE AVENUE Incredible Opportunity in the Heart of Eastport! Beautifully remodeled Victorian located on the Eastport Peninsula. Features include a welcoming front porch, wood floors, and a chef’s kitchen with Viking appliances, a 6-burner stove, and vented hood. Windows and roof were replaced in 2025; roof i ANNAPOLIS, MD Living Area: 2130 Sqft.	2 Beds, 3 Baths	$1,449,000
1005 HYDE PARK DRIVE Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, g ANNAPOLIS, MD Living Area: 1190 Sqft.	2 Beds, 1 Bath	$515,000
1007 PARK AVENUE Experience the Eastport Lifestyle in a Stunning Rebuilt Home Enjoy coastal living in this beautifully rebuilt Eastport residence. Completely gutted and expanded in 2023, this home combines modern luxury with timeless charm. The chef’s kitchen is a showstopper, featuring a 36-inch Bertazzoni rang ANNAPOLIS, MD Living Area: 2430 Sqft.	3 Beds, 4 Baths	$1,075,000
39 WINDWHISPER LANE RARE OPPORTUNITY TO BUY A WATERFRONT PROPERTY IN ANNAPOLIS AT THIS PRICE POINT! LOCATED ON A CUL-DE-SAC, THIS PROPERTY BACKS TO AND HAS SEASONAL VIEWS OF THE HEADWATERS OF BACK CREEK, CONNECTING TO THE CHESAPEAKE BAY. THE REAR OF THE PROPERTY IS WOODED AND IS HOME TO A PROTECTED BIRD SANCTUARY. THE ANNAPOLIS, MD Living Area: 3193 Sqft.	3 Beds, 4 Baths	$675,000
1002 TYLER AVENUE Location Location location!! Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 ANNAPOLIS, MD Living Area: 1920 Sqft.	5 Beds, 2 Baths	$580,000
10 SAILORS WAY This home is nestled in a lush garden setting, so close to dining, shopping and all that downtown Eastport and Annapolis have to offer yet this home feels tucked in to its own private space. This home has been lovingly cared for by the original owner. The private back stone patio with circular st ANNAPOLIS, MD Living Area: 2325 Sqft.	3 Beds, 4 Baths	$995,000
215 CHESTER AVENUE Embrace the Eastport lifestyle in this charming craftsman just steps from the water and downtown Annapolis. This beautifully maintained home offers 4 bedrooms, 3.5 baths, an elevator, and sitting areas on each level. The reverse floor plan features a gourmet kitchen, dining area, and living room wit ANNAPOLIS, MD Living Area: 3421 Sqft.	4 Beds, 4 Baths	$1,895,000
1016 CARRS ROAD Not one but two OPEN HOUSES this weekend! Visit this home Friday from 3PM-5PM or Saturday 2:30PM to 4:30PM! Tucked away in Carrs Manor on the Annapolis Neck Peninsula, this 2-bedroom, 2-bath rancher offers a peaceful, private setting with all the conveniences of city living. This desirable ranch-sty ANNAPOLIS, MD Living Area: 1205 Sqft.	2 Beds, 2 Baths	$450,000
320 CHESTER AVENUE Rare opportunity to own a charming 2-unit building in the heart of Eastport, offering water views from both units. Each residence features its own private entrance and deck, perfect for enjoying the sights and sounds of small town living and serene surroundings. Thoughtfully designed, both units inc ANNAPOLIS, MD Living Area: 1176 Sqft.	2 Beds, 2 Baths	$779,000
310 ADAMS STREET Love where you live and be within walking distance to nearly everything in Eastport and Downtown Annapolis. This home has been meticulously updated and maintained and features three full levels, a full-length front porch, rear deck and private driveway. The upper level boasts hardwood floors, three ANNAPOLIS, MD Living Area: 2572 Sqft.	3 Beds, 5 Baths	$1,598,000
742 WARREN DRIVE Updated, mid-century, 4 bed-, 2 bathroom home in desirable and quiet Eastport neighborhood with water privileges. Lots of professional interior & exterior pics coming next week! Only a short stroll to Downtown Annapolis shops and restaurants with easy access to Route 50. Private neighborhood waterf ANNAPOLIS, MD Living Area: 1740 Sqft.	4 Beds, 2 Baths	$679,000
1011 HYDE PARK DRIVE This updated home offers 3 bedrooms and 2 full baths, with flexible living spaces throughout. The main level features hardwood & tile floors, an updated kitchen with stainless steel appliances (including a brand-new dishwasher), white cabinetry, updated countertops, and plenty of space for a dining ANNAPOLIS, MD Living Area: 1928 Sqft.	3 Beds, 2 Baths	$575,000
412 JEFFERSON STREET Beautifully Appointed Eastport Home. Conveniently located in the heart of Eastport, Annapolis, this newer home offers the perfect blend of style, comfort, and walkability. Set on a premium corner lot, the property features a desirable detached garage and wonderful curb appeal. The main level showca ANNAPOLIS, MD Living Area: 2631 Sqft.	3 Beds, 3 Baths	$1,175,000
513 HORN POINT DRIVE Exceptional Waterfront and Beachfront living on Horn Point in coveted Eastport. Launch your kayak or SUP after morning coffee, and watch the sailboat races from your deck, yard, and beach later that day. This elegant charmer is the Perfect place to watch the Blue Angels without leaving home! The hom ANNAPOLIS, MD Living Area: 3186 Sqft.	4 Beds, 3 Baths	$3,500,000
13 ELLIOTT ROAD Perfectly situated just minutes from the heart of Downtown Annapolis, yet tucked away for privacy, this 4 br, 3.5 bath NEW CONSTRUCTION coastal inspired home with a 2 car garage and optional detached guest cottage by Whitehall Building & Company offers the best of both worlds—convenience and tranq ANNAPOLIS, MD Living Area: 3292 Sqft.	4 Beds, 4 Baths	$1,175,000
192 DUKE OF GLOUCESTER Price Improvement! 100k Reduction. Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after ANNAPOLIS, MD Living Area: 3415 Sqft.	6 Beds, 4 Baths	$2,100,000
703 A GLENDON AVENUE Stunning Waterfront New Construction 0n Back Creek in the Eastport area. Don't miss this rare opportunity to build your dream home in one of Annapolis’s most sought-after waterfront communities. Ideally located on a quiet, picturesque corner lot in Eastport, this beautifully designed custom home ANNAPOLIS, MD Living Area: 4300 Sqft.	4 Beds, 5 Baths	$2,375,000
179 GREEN STREET Experience the Essence of Annapolis Charm at 179 Green Street Nestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, t ANNAPOLIS, MD Living Area: 1656 Sqft.	2 Beds, 2 Baths	$1,175,000
9 SHIPWRIGHT STREET Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet stree ANNAPOLIS, MD Living Area: 2621 Sqft.	3 Beds, 3 Baths	$3,495,000
1 SHIPWRIGHT HARBOR Stately French Villa on Spa Creek in downtown Annapolis! This jewel box of a home was designed and built by renowned local architect as the culmination of an award winning career. The unsurpassed attention to architectural details, exquisitely curated finishes and breathtaking views of Spa Creek pl ANNAPOLIS, MD Living Area: 3108 Sqft.	3 Beds, 4 Baths	$5,898,000
986 YACHTSMAN WAY Beautiful 2 bedroom 2 bath home in highly sought after Mariners Point. The house has a brand new roof, kitchen cabinets, and new flooring has been installed throughout the house. The exterior of the house was freshly painted this summer. HOA is only $105 a month, can't beat that in Annapolis! Thi ANNAPOLIS, MD Living Area: 1174 Sqft.	2 Beds, 2 Baths	$405,999
600 SIXTH STREET Welcome to Eastport living at its finest—where timeless coastal design meets understated luxury just one block from the water. Perfectly situated on the highly sought Eastport Pennisula, this elegant two-story home blends craftsmanship, comfort, and walkable charm in one of Annapolis’s most desi ANNAPOLIS, MD Living Area: 3343 Sqft.	3 Beds, 4 Baths	$2,350,000

Annapolis, Maryland, United States

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Homes for sale near Dick Sims Park, Annapolis, MD, USA

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