Vintage homes for sale & real estate in 21401, MD

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COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21401, MD:
The ideal Murray Hill home with a little bit of everything: one-level living, a private driveway, lovely yard, and fully updated. A wonderful single-family home and an appealing alternative to condo living, with your own outdoor space and parking right outside your door. This stylish home is fully renovated and truly move-in ready, with dramatic open-beam ceilings that give the interior a style all its own. The most recent improvements include new quartz countertops, newly reconfigured front steps with new railings, a widened and expanded driveway, and a new skylight that brings even more natural light inside. The screened front porch is a great spot for a morning cup of coffee and to enjoy

$975,000

3 beds2 baths1,100 sq ft

Private driveway • Fully updated • Outdoor space

122 Smith Ave, Annapolis, MD 21401

(410) 263-8686

OPEN SAT, 9:30AM TO 11AM

ABOUT THIS HOME
Vintage Home for sale in 21401, MD:
Nestled in the coveted Dreams Landing community, this charming 2-bedroom townhouse offers a unique blend of comfort and luxury, perfectly situated on the Severn River. Enjoy dinner al-fresco on your own private patio! The property boasts water access, allowing residents to choose boating, fishing or just observing the river right at their doorstep. Enjoy leisurely strolls along walking paths or unwind at the community pool, where the gentle sounds of the river create a tranquil atmosphere. The community amenities are exceptional, featuring a well-maintained marina, outdoor pool, and common grounds perfect for gatherings. This residence harmonizes traditional charm with modern conveniences.

$519,900

2 beds1.5 baths992 sq ft

Community pool • Common grounds • Private patio

1006 Dreams Landing Way, Annapolis, MD 21401

(410) 823-0033

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in 21401, MD:
COMING SOON! On the market this Thursday 8/20/2026. 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, blending all the comforts of modern design with the historic charm of Homewood. A traditional front porch, turned white columns and soft buttery siding announce the home from the street while a long driveway offers the rare luxury of off street parking in one of Annapolis's most walkable in-town pockets. Inside, tall ceilings and recessed lighting set an airy tone against gorgeous oak flooring on the main level and the beautifully refinished original pine flooring on the stai

$835,000

3 beds2.5 baths1,512 sq ft

Fully renovated • Lovely front porch • Attic storage

16 Woodlawn Ave, Annapolis, MD 21401

(410) 280-5600

ABOUT THIS HOME
Vintage Home for sale in 21401, MD:
AUCTION! Occupied property and inspections NOT available - sold as-is. No for sale sign. Contact with occupants is prohibited. No financed offers/bids as there is NO access. Property is being sold occupied with any and all occupants in AS IS/WHERE IS condition. Neither the seller nor the listing broker can verify the existence of any lease agreement, either written or verbal, nor any rental amount being paid, due or owing. Please DO NOT disturb the occupants. Access for inspections or other purposes is NOT available. Buyer is assuming ALL responsibility for any necessary eviction action. Do not email any offers as the property is being sold via auction and all bids are to be submitted onlin

$385,000

3 beds1 bath1,296 sq ft

6,750 sq ft lot • Built 1950 • Listed 6 days

208 Parker Ave, Annapolis, MD 21401

(410) 531-0321

ABOUT THIS HOME
Vintage Home for sale in 21401, MD:
Welcome to 145 Prince George St. , a distinctive historic home that blends classic architectural character with thoughtful modern updates. From its welcoming front porch and slate roof to its original wood details and spacious interior, this home offers a rare combination of charm, character, and versatility. The main level features beautiful wood floors and an inviting floor plan designed for both everyday living and entertaining. The spacious kitchen offers abundant cabinetry and storage, including a built-in pantry cabinet, along with an island and granite countertops. Stainless steel appliances include a dishwasher and microwave, a new four-burner gas range/oven and new French-door refr

$1,199,000

3 beds3 baths1,476 sq ft

Spacious kitchen • Historic home • Slate roof

145 Prince George St, Annapolis, MD 21401

(410) 465-8300

Property at 1204 Dreams Landing Way #1204, Annapolis, MD 21401, 2 beds, 1 bath

$449,000

2 beds1 bath981 sq ft

1204 Dreams Landing Way #1204, Annapolis, MD 21401

(410) 263-8686

Property at 62 Southgate Ave, Annapolis, MD 21401, 4 beds, 4 baths

$2,400,000

4 beds4 baths3,415 sq ft

62 Southgate Ave, Annapolis, MD 21401

(410) 263-8686

Property at 709 Glenwood St #57, Annapolis, MD 21401, 1 bed, 1 bath

$190,000

1 bed1 bath595 sq ft

709 Glenwood St #57, Annapolis, MD 21401

(410) 544-8800

Property at 20 Shaw St, Annapolis, MD 21401, 3 beds, 2.5 baths

$999,500

3 beds2.5 baths1,500 sq ft

20 Shaw St, Annapolis, MD 21401

(410) 263-8686

Property at 268 King George St, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,575,000

4 beds3.5 baths2,372 sq ft

268 King George St, Annapolis, MD 21401

(443) 906-3848

Property at 87 Shipwright St, Annapolis, MD 21401, 6 beds, 4.5 baths

$1,699,900

6 beds4.5 baths2,744 sq ft

87 Shipwright St, Annapolis, MD 21401

(443) 274-1900

Property at 1724 Robinhood Rd, Annapolis, MD 21401, 4 beds, 3 baths

$959,000

4 beds3 baths3,080 sq ft

1724 Robinhood Rd, Annapolis, MD 21401

(410) 266-0600

Property at 107 Monticello Ave, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,350,000

4 beds3.5 baths3,316 sq ft

107 Monticello Ave, Annapolis, MD 21401

(888) 860-7369

Property at 111 Conduit St, Annapolis, MD 21401, 4 beds, 3 baths

$985,000

4 beds3 baths2,000 sq ft

111 Conduit St, Annapolis, MD 21401

(410) 268-8400

Property at 34 Pinkney St, Annapolis, MD 21401, 2 beds, 1.5 baths

$685,000

2 beds1.5 baths1,040 sq ft

34 Pinkney St, Annapolis, MD 21401

(410) 280-5600

Property at 310 Epping Way, Annapolis, MD 21401, 3 beds, 2 baths

$1,050,000

3 beds2 baths2,036 sq ft

310 Epping Way, Annapolis, MD 21401

(410) 280-5600

Property at 11 1/2 College Ave, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,295,000

3 beds2.5 baths1,501 sq ft

11 1/2 College Ave, Annapolis, MD 21401

(410) 263-8686

Property at 607 Melvin Ave, Annapolis, MD 21401, 2 beds, 2 baths

$899,000

2 beds2 baths1,102 sq ft

607 Melvin Ave, Annapolis, MD 21401

(410) 263-8686

Property at 202 Wardour Dr, Annapolis, MD 21401, 5 beds, 2 baths

$2,149,000

5 beds2 baths2,100 sq ft

202 Wardour Dr, Annapolis, MD 21401

(443) 372-7171

Property at 25 Dorsey Ave, Annapolis, MD 21401, 4 beds, 3 baths

$529,900

4 beds3 baths1,092 sq ft

25 Dorsey Ave, Annapolis, MD 21401

Property at 16 Maryland Ave, Annapolis, MD 21401, 6 beds, 4.5 baths

$3,849,000

6 beds4.5 baths4,474 sq ft

16 Maryland Ave, Annapolis, MD 21401

(410) 263-8686

Property at 102 Louis Dr, Annapolis, MD 21401, 2 beds, 1 bath

$360,000

2 beds1 bath714 sq ft

102 Louis Dr, Annapolis, MD 21401

Property at 238 King George St, Annapolis, MD 21401, 4 beds, 4 baths

$2,950,000

4 beds4 baths3,750 sq ft

238 King George St, Annapolis, MD 21401

(410) 263-8686

Property at 11 S Acton Pl, Annapolis, MD 21401, 4 beds, 3.5 baths

$7,250,000

4 beds3.5 baths3,658 sq ft

11 S Acton Pl, Annapolis, MD 21401

(844) 551-7325

Property at 75 Shipwright St, Annapolis, MD 21401, 5 beds, 3.5 baths

$1,449,000

5 beds3.5 baths2,557 sq ft

75 Shipwright St, Annapolis, MD 21401

(410) 224-3600

Property at 19 Old Solomons Island Rd, Annapolis, MD 21401, 4 beds, 1.5 baths

$1,150,000

4 beds1.5 baths1,176 sq ft

19 Old Solomons Island Rd, Annapolis, MD 21401

(410) 823-0033

Property at 198 Clay St, Annapolis, MD 21401, 2 beds, 1.5 baths

$375,000

2 beds1.5 baths902 sq ft

198 Clay St, Annapolis, MD 21401

(443) 292-6767

Property at 83 Market St, Annapolis, MD 21401, 5 beds, 4 baths

$2,295,000

5 beds4 baths3,178 sq ft

83 Market St, Annapolis, MD 21401

(410) 263-8686

Property at 192 Duke Of Gloucester, Annapolis, MD 21401, 6 beds, 4 baths

$1,950,000

6 beds4 baths3,415 sq ft

192 Duke Of Gloucester, Annapolis, MD 21401

(301) 755-5613

Property at 805 Spa Rd, Annapolis, MD 21401, 9 beds, 4.5 baths

$1,148,000

9 beds4.5 baths2,800 sq ft

805 Spa Rd, Annapolis, MD 21401

(301) 459-5040

Property at 146 Duke Of Gloucester St, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,999,999

4 beds3.5 baths3,042 sq ft

146 Duke Of Gloucester St, Annapolis, MD 21401

(410) 255-3690

Property at 165 King George St, Annapolis, MD 21401, 4 beds, 3 baths

$1,375,000

4 beds3 baths2,649 sq ft

165 King George St, Annapolis, MD 21401

(410) 266-9005

Property at 9 Shipwright St, Annapolis, MD 21401, 3 beds, 2.5 baths

$3,495,000

3 beds2.5 baths2,621 sq ft

9 Shipwright St, Annapolis, MD 21401

(410) 280-5600

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Vintage Homes for Sale in 21401

There are currently 33 vintage homes for sale in 21401 at a median listing price of $845K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21401 stay on the market for 53 days and receive 1 offers. This map is refreshed with the newest listings in 21401 every 15 minutes.

In the past month, 73 homes have been sold in 21401. In addition to houses in 21401, there were also 40 condos, 49 townhouses, and 1 multi-family unit for sale in 21401 last month. Find your dream home in 21401 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21401 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21401. If you're looking to sell your home in the 21401 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21401 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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