Sherwood Forest, MD homes for sale & real estate

33 homes

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COMING SOON

ABOUT THIS HOME
Sherwood Forest, MD Homes for Sale
Coming Soon in Homewood. Classic Cape Cod with standout curb appeal, offering a timeless look straight out of a favorite home-inspo Instagram moment. A rare two-car garage, large flat rear yard, and thoughtful updates including an open kitchen, new flooring, and reconfigured living spaces. Newer HardiePlank® exterior and a spacious primary bedroom with a large primary bath. Just a short stroll along the Homewood Walking Trail to downtown Annapolis—one of the area’s most sought-after neighborhoods.

$889,000

3 beds2.5 baths1,890 sq ft

25 Locust Ave, Annapolis, MD 21401

7,500 sq ft lot • 2 garage spots • Built 1930

(410) 263-8686

ABOUT THIS HOME
Sherwood Forest, MD Homes for Sale
Discover this enchanting 2 BR, 3 level Gingerbread Cottage in the heart of popular Homewood! A rare Sears 1929 kit home, it has been lovingly restored to showcase its historic charm, featuring original hardwood floors throughout, plaster walls, curved archways and a wonderfully preserved eat-in Kitchen complete with banquet booth. The main level offers an inviting flow: a separate Family Room with built-ins and rear entrance, a Living Room with refurbished gas fireplace and a formal Dining Room that leads into the cozy, character filled Kitchen equipped with 5 burner stove and double oven. All great entertaining spaces! Storage is exceptional, with an oversized attic brimming with potential

$675,000

2 beds1.5 baths1,540 sq ft

219 Glen Ave, Annapolis, MD 21401

Plaster walls • Curved archways • Banquet booth

(410) 263-8686

3D WALKTHROUGH

ABOUT THIS HOME
Sherwood Forest, MD Homes for Sale
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. 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 furnished with kitchen appliances, items, dishware, glasswar

$1,375,000

4 beds3 baths2,649 sq ft

165 King George St, Annapolis, MD 21401

Built 1900 • Listed 25 days

(410) 266-9005

ABOUT THIS HOME
Sherwood Forest, MD Homes for Sale
Stunningly Updated Historic District Charmer, One Block From The Water/Ego Alley! 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 offer

$875,000

3 beds2 baths1,376 sq ft

54 Cornhill St, Annapolis, MD 21401

Built 1800 • Listed 30 days

(410) 224-3600

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

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

$1,799,000

4 beds3.5 baths3,421 sq ft

215 Chester Ave, Annapolis, MD 21403

(410) 263-8686

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

$1,695,000

2 beds2.5 baths2,269 sq ft

51 Franklin St, Annapolis, MD 21401

(410) 263-8686

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 7101 Bay Front Dr #204, Annapolis, MD 21403, 1 bed, 1.5 baths

$320,000

1 bed1.5 baths1,000 sq ft

7101 Bay Front Dr #204, Annapolis, MD 21403

(443) 274-1900

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 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 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 5 Park Pl #626, Annapolis, MD 21401, 2 beds, 2 baths

$679,000

2 beds2 baths1,314 sq ft

5 Park Pl #626, Annapolis, MD 21401

(410) 263-3400

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 #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 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 5 Park Pl #431, Annapolis, MD 21401, 1 bed, 1 bath

$489,900

1 bed1 bath839 sq ft

5 Park Pl #431, Annapolis, MD 21401

(410) 224-3600

Property at 5 Park Pl #722, Annapolis, MD 21401, 2 beds, 2 baths

$799,000

2 beds2 baths1,285 sq ft

5 Park Pl #722, Annapolis, MD 21401

(410) 280-5600

Property at 10 Annapolis St, Annapolis, MD 21401

$975,000

— beds— baths— sq ft

10 Annapolis St, Annapolis, MD 21401

(410) 263-8686

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