Sherwood Forest, MD homes for sale & real estate

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ABOUT THIS HOME
Sherwood Forest, MD Homes for Sale
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
Sherwood Forest, MD Homes for Sale
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
Sherwood Forest, MD Homes for Sale
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
Sherwood Forest, MD Homes for Sale
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
Sherwood Forest, MD Homes for Sale
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 30 Gentry Ct, Annapolis, MD 21403, 3 beds, 2.5 baths

$349,000

3 beds2.5 baths1,460 sq ft

30 Gentry Ct, Annapolis, MD 21403

(410) 263-8686

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 215 Chester Ave, Annapolis, MD 21403, 4 beds, 3.5 baths

$1,895,000

4 beds3.5 baths3,421 sq ft

215 Chester Ave, Annapolis, MD 21403

(410) 263-8686

Property at 2 Southgate Ave #10, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,975,000

3 beds2.5 baths3,884 sq ft

2 Southgate Ave #10, Annapolis, MD 21401

(410) 280-5600

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 302 Forbes St Unit D, Annapolis, MD 21401, 2 beds, 2 baths

$450,000

2 beds2 baths844 sq ft

302 Forbes St Unit D, Annapolis, MD 21401

(410) 429-7425

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 1 Tucker St, Annapolis, MD 21401, 3 beds, 2.5 baths

$1,145,000

3 beds2.5 baths1,869 sq ft

1 Tucker St, Annapolis, MD 21401

(301) 921-4500

Property at 411 Ridgely Ave, Annapolis, MD 21401, 4 beds, 4.5 baths

$3,950,000

4 beds4.5 baths5,950 sq ft

411 Ridgely Ave, Annapolis, MD 21401

(410) 280-5600

Property at 513 Horn Point Dr, Annapolis, MD 21403, 4 beds, 3 baths

$3,500,000

4 beds3 baths3,186 sq ft

513 Horn Point Dr, Annapolis, MD 21403

(410) 263-8686

Property at 66 Franklin St #101, Annapolis, MD 21401, 2 beds, 2 baths

$699,000

2 beds2 baths1,296 sq ft

66 Franklin St #101, Annapolis, MD 21401

(410) 263-8686

Property at 289 State St #4, Annapolis, MD 21403, 2 beds, 2.5 baths

$3,975,000

2 beds2.5 baths1,938 sq ft

289 State St #4, Annapolis, MD 21403

(410) 260-2800

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 51 Franklin St, Annapolis, MD 21401, 2 beds, 2.5 baths

$1,749,900

2 beds2.5 baths2,269 sq ft

51 Franklin St, Annapolis, MD 21401

(410) 263-8686

Property at 1004 Primrose Rd #203, Annapolis, MD 21403, 2 beds, 2 baths

$298,500

2 beds2 baths1,020 sq ft

1004 Primrose Rd #203, Annapolis, MD 21403

(866) 987-3937

Property at 312 Severn Ave Unit W 401, Annapolis, MD 21403, 1 bed, 1 bath

$515,000

1 bed1 bath660 sq ft

312 Severn Ave Unit W 401, Annapolis, MD 21403

(410) 263-8686

Property at 285 West St #15, Annapolis, MD 21401, 4 beds, 4.5 baths

$1,595,000

4 beds4.5 baths2,720 sq ft

285 West St #15, Annapolis, MD 21401

(410) 280-5600

Property at 5 Park Pl #428, Annapolis, MD 21401, 3 beds, 2.5 baths

$925,000

3 beds2.5 baths1,822 sq ft

5 Park Pl #428, Annapolis, MD 21401

(410) 429-7425

Property at 139 Spa Dr, Annapolis, MD 21403, 4 beds, 4.5 baths

$2,850,000

4 beds4.5 baths4,628 sq ft

139 Spa Dr, Annapolis, MD 21403

(410) 505-9700

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 5 Park Pl #217, Annapolis, MD 21401, 2 beds, 2 baths

$679,900

2 beds2 baths1,343 sq ft

5 Park Pl #217, Annapolis, MD 21401

(302) 360-0300

Property at 1207 Mcguckian St, Annapolis, MD 21401, 4 beds, 3.5 baths

$1,395,000

4 beds3.5 baths3,150 sq ft

1207 Mcguckian St, Annapolis, MD 21401

(888) 860-7369

Property at 287 State St #3, Annapolis, MD 21403, 3 beds, 4.5 baths

$7,950,000

3 beds4.5 baths4,702 sq ft

287 State St #3, Annapolis, MD 21403

(410) 280-5600

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 5 Park Pl #602, Annapolis, MD 21401, 2 beds, 2 baths

$675,000

2 beds2 baths1,213 sq ft

5 Park Pl #602, 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 5 Park Pl #107, Annapolis, MD 21401, 2 beds, 2 baths

$625,000

2 beds2 baths1,272 sq ft

5 Park Pl #107, Annapolis, MD 21401

Property at 66 Franklin St #509, Annapolis, MD 21401, 3 beds, 3.5 baths

$1,850,000

3 beds3.5 baths2,477 sq ft

66 Franklin St #509, Annapolis, MD 21401

(410) 266-0600

Property at 5 Park Pl #314, Annapolis, MD 21401, 2 beds, 2 baths

$554,000

2 beds2 baths1,056 sq ft

5 Park Pl #314, Annapolis, MD 21401

(410) 224-3600

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