Vintage homes for sale & real estate in Annapolis, MD

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3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Annapolis, MD:
There are so many option available for this property in the heart of Historic Annapolis. You may want to convert the entire home back to one living unit. You may want to live in one, long-term rent the other two or short term rent one. You may choose that it be be used for a couple/single person to live in one apt and rent out 2 or have a multigenerational combined family living in 1, 2 (while renting 1) or all 3. There are so many possibilities to enjoy this amazing property. Currently it is utilized via short term rentals per unit. This is 3 fully finished levels and units above grade. The basement level houses the storage area, HVAC and shared laundry area. All of the units are fully fu

$1,375,000

4 beds3 baths2,649 sq ft

165 King George St, Annapolis, MD 21401

Built 1900

(410) 266-9005

ABOUT THIS HOME
Vintage Home for sale in Annapolis, MD:
This is an estate sale and being sold "As Is. " A rancher that has been in this family for years, it does require updating--the value of this property is in the land and located in Pendennis Mount as many individuals would love to build a larger home in this community or rehab an existing home. This property is located in the well-desired subdivision of Pendennis Mount with properties selling for up to $9M on the water. . This property in not located in the "city" of Anapolis so no city property tax assessed. There is a private community access to the waters of the Severn River that has a pier and boat slips. .. . If one wants to join the Boat Club, one can join--age

$900,000

3 beds1.5 baths1,936 sq ft

16 Brice Rd, Annapolis, MD 21409

0.27 acre lot • 3 parking spots • Built 1954

(410) 255-3690

ABOUT THIS HOME
Vintage Home for sale in Annapolis, MD:
INVESTOR ALERT!!! This cottage has a newer roof, 2018, and a encapsulated and sump installed in a sealed crawl space 2022. Large back yard with rain garden. She needs some good TLC but excellent investment opportunity! Over 1400 sq ft, 3 bedroom, 2 full bath, Peek-a-boo water view and great location . Close to all the community privledges and being sold strictly "AS IS". More photos are on their way!

$450,000

3 beds2 baths1,412 sq ft

3426 Narragansett Ave, Annapolis, MD 21403

Newer roof • Large back yard • Rain garden

(410) 263-8686

ABOUT THIS HOME
Vintage Home for sale in Annapolis, MD:
Stunningly Updated Historic District Charmer! Nestled near the top of iconic Cornhill Street—just steps from State Circle and the boutiques and restaurants of Maryland Avenue—this beautifully restored brick end-unit blends timeless Annapolis character with modern luxury. Step inside to an inviting open floor plan filled with natural light and accented by gleaming heart pine floors. The highlight of the main level is the completely renovated gourmet kitchen, featuring quartz countertops, stainless steel appliances, custom cabinetry, and designer finishes—a perfect blend of elegance and functionality. The flexible living/dining space offers built-ins, a wood-burning fireplac

$875,000

3 beds2 baths1,376 sq ft

54 Cornhill St, Annapolis, MD 21401

Built 1800 • Listed 6 days

(410) 224-3600

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Annapolis, MD:
Set in the sought-after Hillsmere neighborhood of Annapolis, this 2,200-square-foot rancher offers a calm, coastal feel enhanced by a single serene water view and a long list of significant updates. The home features a brand new kitchen with fully custom cabinets and a Wolf Range, newly renovated bathrooms, a roof replaced in 2021 with a 10-year warranty as reported by the seller, new windows added in 2022 according to seller-provided information, a new HVAC system also installed in 2022 per seller records, a new hot water heater from 2023 as stated by the seller, and a water softener from 2019 based on the seller’s account, along with numerous additional upgrades throughout the prope

$995,000

3 beds2 baths2,187 sq ft

150 E Bay View Dr, Annapolis, MD 21403

0.48 acre lot • 2 garage spots • Community pool

(410) 486-4504

Property at 219 Glen Ave, Annapolis, MD 21401, 2 beds, 1.5 baths

$675,000

2 beds1.5 baths1,540 sq ft

219 Glen Ave, Annapolis, MD 21401

(410) 263-8686

Property at 106 Roselawn Rd, Annapolis, MD 21403, 4 beds, 2 baths

$350,000

4 beds2 baths1,323 sq ft

106 Roselawn Rd, Annapolis, MD 21403

(410) 544-8800

Property at 39 Southgate Ave, Annapolis, MD 21401, 5 beds, 3.5 baths

$3,750,000

5 beds3.5 baths6,789 sq ft

39 Southgate Ave, Annapolis, MD 21401

(410) 280-5600

Property at 3 Chester Ave, Annapolis, MD 21403, 3 beds, 3 baths

$1,730,000

3 beds3 baths2,815 sq ft

3 Chester Ave, Annapolis, MD 21403

(410) 972-4000

Property at 30 Decatur Ave, Annapolis, MD 21403, 4 beds, 2 baths

$1,100,000

4 beds2 baths1,477 sq ft

30 Decatur Ave, Annapolis, MD 21403

(410) 280-5600

Property at 6 Victor Pkwy, Annapolis, MD 21403, 3 beds, 1 bath

$374,900

3 beds1 bath912 sq ft

6 Victor Pkwy, Annapolis, MD 21403

(410) 729-7700

Property at 200 Chesapeake Ave, Annapolis, MD 21403, 2 beds, 1.5 baths

$1,099,000

2 beds1.5 baths2,942 sq ft

200 Chesapeake Ave, Annapolis, MD 21403

(703) 310-6111

Property at 1007 Park Ave, Annapolis, MD 21403, 3 beds, 3 baths

$1,075,000

3 beds3 baths2,430 sq ft

1007 Park Ave, Annapolis, MD 21403

(410) 972-4000

Property at 1913 Dulaney Pl, Annapolis, MD 21409, 5 beds, 2 baths

$925,000

5 beds2 baths2,969 sq ft

1913 Dulaney Pl, Annapolis, MD 21409

(410) 224-3200

Property at 1831 Drew St, Annapolis, MD 21401, 5 beds, 2 baths

$570,000

5 beds2 baths2,236 sq ft

1831 Drew St, Annapolis, MD 21401

(443) 318-8800

Property at 2638 Greenbriar Ln, Annapolis, MD 21401, 4 beds, 2 baths

$650,000

4 beds2 baths2,606 sq ft

2638 Greenbriar Ln, Annapolis, MD 21401

(410) 296-8440

Property at 120 Chesapeake Ave, Annapolis, MD 21403, 2 beds, 2.5 baths

$1,449,000

2 beds2.5 baths2,130 sq ft

120 Chesapeake Ave, Annapolis, MD 21403

(410) 972-4000

Property at 3137 Catrina Ln, Annapolis, MD 21403, 3 beds, 2 baths

$1,750,000

3 beds2 baths2,970 sq ft

3137 Catrina Ln, Annapolis, MD 21403

(410) 280-5600

Property at 212 Duke Of Gloucester St, Annapolis, MD 21401

$599,900

0 beds— baths2,300 sq ft

212 Duke Of Gloucester St, Annapolis, MD 21401

(443) 573-9200

Property at 34 Lafayette Ave, Annapolis, MD 21401, 3 beds, 1 bath

$599,900

3 beds1 bath2,280 sq ft

34 Lafayette Ave, Annapolis, MD 21401

(410) 547-1116

Property at 48 Murray Ave, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,595,000

4 beds3.5 baths2,580 sq ft

48 Murray Ave, Annapolis, MD 21401

(202) 386-6330

Property at 320 Chester Ave, Annapolis, MD 21403, 2 beds, 2 baths

$779,000

2 beds2 baths1,176 sq ft

320 Chester Ave, Annapolis, MD 21403

(410) 224-4999

Property at 1808 Lincoln Dr, Annapolis, MD 21401, 3 beds, 1 bath

$419,000

3 beds1 bath1,008 sq ft

1808 Lincoln Dr, Annapolis, MD 21401

(410) 547-1116

Property at 228 Dubois Rd, Annapolis, MD 21401, 4 beds, 3 baths

$675,000

4 beds3 baths2,900 sq ft

228 Dubois Rd, Annapolis, MD 21401

(410) 260-2800

Property at 111 Clay St, Annapolis, MD 21401, 3 beds, 1.5 baths

$525,000

3 beds1.5 baths1,568 sq ft

111 Clay St, Annapolis, MD 21401

(855) 450-0442

Property at 173 Williams Dr, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,425,000

4 beds3.5 baths2,382 sq ft

173 Williams Dr, Annapolis, MD 21401

(410) 280-5600

Property at 192 Clay St, Annapolis, MD 21401, 2 beds, 1.5 baths

$299,900

2 beds1.5 baths1,244 sq ft

192 Clay St, Annapolis, MD 21401

(410) 260-2800

Property at 1979 Baltimore Annapolis Blvd, Annapolis, MD 21409, 5 beds, 2 baths

$3,200,000

5 beds2 baths5,522 sq ft

1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

(240) 383-1350

Property at 1715 Porters Hill Rd, Annapolis, MD 21401, 4 beds, 5 baths

$3,995,000

4 beds5 baths6,594 sq ft

1715 Porters Hill Rd, Annapolis, MD 21401

(410) 260-2800

Property at 1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409, 5 beds, 2 baths

$1,300,000

5 beds2 baths1,919 sq ft

1814 & 1836 Pleasant Plains & Cherry Rd, Annapolis, MD 21409

(410) 224-0600

Property at 3276 Kitty Duvall Dr, Annapolis, MD 21403, 2 beds, 2 baths

$549,000

2 beds2 baths1,434 sq ft

3276 Kitty Duvall Dr, Annapolis, MD 21403

(240) 219-2422

Property at 1014 St Charles Dr, Annapolis, MD 21409, 5 beds, 3 baths

$699,900

5 beds3 baths3,312 sq ft

1014 St Charles Dr, Annapolis, MD 21409

(301) 854-2155

Property at 41 Cornhill St, Annapolis, MD 21401, 4 beds, 2.5 baths

$2,100,000

4 beds2.5 baths4,404 sq ft

41 Cornhill St, Annapolis, MD 21401

(301) 661-5222

Property at 179 Green St, Annapolis, MD 21401, 2 beds, 1.5 baths

$1,175,000

2 beds1.5 baths1,656 sq ft

179 Green St, Annapolis, MD 21401

(410) 263-3400

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

Property at 14-A Dorsey Ave, Annapolis, MD 21401, 4 beds, 2.5 baths

$600,000

4 beds2.5 baths2,037 sq ft

14-A Dorsey Ave, Annapolis, MD 21401

(410) 220-4648

Property at 1016 E College Pkwy, Annapolis, MD 21409

$1,995,000

— beds— baths— sq ft

1016 E College Pkwy, Annapolis, MD 21409

(410) 280-5600

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Vintage Homes for Sale in Annapolis

There are currently 37 vintage homes for sale in Annapolis at a median listing price of $675K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Annapolis stay on the market for 50 days and receive 4 offers. Popular neighborhoods include Anchorage, West Annapolis, Gingerville, Admiral Heights, and Old Annapolis Neck. This map is refreshed with the newest listings in Annapolis every 15 minutes.

In the past month, 37 homes have been sold in Annapolis. In addition to houses in Annapolis, there were also 46 condos, 54 townhouses, and 1 multi-family unit for sale in Annapolis last month. Annapolis is a minimally walkable city in Maryland with a Walk Score of 48. Annapolis is home to approximately 37,699 people and 25,456 jobs. Find your dream home in Annapolis 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 Annapolis are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Annapolis. Our Annapolis real estate stats and trends will give you more information about home buying and selling trends in Annapolis. If you're looking to sell your home in the Annapolis area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Annapolis with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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