Vintage homes for sale & real estate in Sherwood Forest, MD

19 homes

Sort:

Recommended

OPEN SAT, 1PM TO 3PMVIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
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 you seek, this is the house for you! Located just a few steps from the USNA stadium, walking paths and parks & playing fields! This home features a large, fenced back yard complete with paver patio and mature trees…perfect for BBQs and cozy fire pit evenings! On the main level you will find hardwood floors throughout, and sunlit beautiful living room including a wood burning fireplace! The kitchen offers white cabinets, granite countertops, and plenty of table space including built-in bench with st

$650,000

4 beds2 baths1,653 sq ft

309 N Woodlawn Ave N, Annapolis, MD 21401

8,210 sq ft lot • Built 1951

(410) 263-3400

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, 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 2 days

(410) 224-3600

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
This Murray Hill masterpiece is a 5-bedroom, 4 bathroom home that was originally built in 1913 and underwent a complete custom renovation a few years ago. Situated on a double lot on one of the most desirable streets in Annapolis. It blends formal sophistication with modern luxuries including an elevator! Offering rare private driveway, a two-car garage with separate storage room. Featuring over 7,000 sq ft, state-of-the-art custom kitchen with two dishwashers, first and second floor laundry rooms, electric window blinds, screened-in-porch, a fully fenced yard, irrigation system, mature landscaping, two fireplaces, high ceilings, crown and dental molding, custom cabinetry throughout, two zo

$3,750,000

5 beds3.5 baths6,789 sq ft

39 Southgate Ave, Annapolis, MD 21401

Private driveway • Two car garage • 0.28 acre lot

(410) 280-5600

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
Step into the heart of Eastport, where charm and convenience meet in this beautifully renovated Cape Cod. Just a short stroll from the water’s edge and downtown Annapolis, this home embodies the Eastport lifestyle — vibrant, nautical, and effortlessly welcoming. From the moment you enter, natural light pours through every window, illuminating three levels of thoughtfully designed living space. Classic details — arched doorways, hardwood floors, custom built-ins, and rich millwork — blend seamlessly with modern updates, creating a home that feels both timeless and fresh. The inviting floor plan offers room for every occasion. A serene primary suite with its own firepl

$1,730,000

3 beds3 baths2,815 sq ft

3 Chester Ave, Annapolis, MD 21403

Renovated cape cod • Natural light • Arched doorways

(410) 972-4000

COMING SOON

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
This is a must see! It is really two dwelling attached in one in Eastport Peninsula, Original Dwelling was a Church and was converted to 2 bedroom and 1.5 bathroom with open floor plan on the main level! 2nd dwelling in the rear is a cozy cottage with a bedroom and loft & kitchenet! Great for renting income!

$1,099,000

2 beds1.5 baths2,942 sq ft

200 Chesapeake Ave, Annapolis, MD 21403

3,360 sq ft lot • Built 1930 • Listed 8 days

(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 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 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 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 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 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 26 Pleasant St, Annapolis, MD 21401, 2 beds, 1 bath

$275,000

2 beds1 bath972 sq ft

26 Pleasant St, Annapolis, MD 21401

(443) 901-2200

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

$2,100,000

6 beds4 baths3,415 sq ft

192 Duke Of Gloucester, Annapolis, MD 21401

(410) 263-8686

Property at 32 East St, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,200,000

3 beds2.5 baths2,100 sq ft

32 East St, Annapolis, MD 21401

(410) 263-8686

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

$429,000

2 beds1.5 baths902 sq ft

198 Clay St, Annapolis, MD 21401

(443) 292-6767

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

Viewing page 1 of 1

End of results

Nearby homes that match your criteria

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
Tucked back from the road and surrounded by trees, this contemporary waterfront home offers privacy and a serene connection to nature. Unique original details have been thoughtfully preserved while the interior has been completely renovated for modern living. From the moment you enter, walls of glass draw your eye through the home to the expansive deck that stretches nearly the full length of the house, showcasing tranquil views of Weems Creek through the trees. The open floor plan features a living room with an electric fireplace providing supplemental heat, a beautifully remodeled gourmet kitchen with bar, a dining area, and a conveniently placed mudroom, pantry, and powder room. Upstairs

$1,425,000

4 beds3.5 baths2,382 sq ft

173 Williams Dr, Annapolis, MD 21401

0.92 acre lot • 6 parking spots • Built 1957

(410) 280-5600

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
Welcome to 1979 Baltimore Annapolis Blvd — where original charm meets opportunity. Set along one of the Severn River’s most desirable stretches with unobstructed views of the U. S. Naval Academy, this distinctive residence offers 5,522 finished square feet across three levels—seamlessly blending timeless character with a 2015 expansion and thoughtful modern updates. Enjoy a front-row seat to the annual Blue Angels air show right from your own waterfront! The property’s deep-water pier and bulkhead, constructed in 2003, feature a 40,000-lb lift, a 15,000-lb lift, and two 1,500-lb jet ski lifts, accommodating multiple vessels with ease. With 10 feet of water depth and

$3,200,000

5 beds2 baths5,522 sq ft

1979 Baltimore Annapolis Blvd, Annapolis, MD 21409

0.84 acre lot • 3 garage spots • Built 1940

(240) 383-1350

ABOUT THIS HOME
Vintage Home for sale in Sherwood Forest, MD:
Welcome to 228 Dubois Road in Annapolis Maryland * * Updated Cape Cod on . 81 Acres in Annapolis! Private Yard and Private Street * * Every Level of this Home has been Updated * * Main Level has Living Room & Kitchen * * Also on Main Level are Two Bedrooms and a Full Bath * * Sunroom on Side of Main Level * * Upper Level has Private Main Bedroom w/ Full Bath * * There is a Smaller Room off of the Primary Bedroom that could be used to a Office/Den/Nursery * * Lower Level has Family Room, Laundry, Full Bath and Another Bedroom * * Large Spacious Yard has been Professional Landscaped * * Roof and Gutters are 2024 * * HVAC is 2025 * * Close to ALL Annapolis has to Offer al

$675,000

4 beds3 baths2,900 sq ft

228 Dubois Rd, Annapolis, MD 21401

0.81 acre lot • 4 parking spots • Built 1950

(410) 260-2800

Vintage Homes for Sale in Sherwood Forest

There are currently 19 vintage homes for sale in Sherwood Forest at a median listing price of $527K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Sherwood Forest stay on the market for 156 days. Popular neighborhoods include Downtown Height District, West Annapolis, Greenbriar Gardens, Admiral Heights, and Wardour. This map is refreshed with the newest listings in Sherwood Forest every 15 minutes.

Find your dream home in Sherwood Forest 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 Sherwood Forest are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Sherwood Forest. Our Sherwood Forest real estate stats and trends will give you more information about home buying and selling trends in Sherwood Forest. If you're looking to sell your home in the Sherwood Forest area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Sherwood Forest with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

More real estate resources for Sherwood Forest, MD

Neighborhoods

Nearby Cities

Zip Codes

Nearby Cities with Vintage Homes

Nearby Neighborhoods with Vintage Homes

More to explore in Sherwood Forest, MD

How to buy a house in Sherwood Forest, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.