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Some homes offer a change of scenery. Others offer an entirely different perspective. Tucked away on 2.75 wooded acres bordering the Sherwood Forest Nature Preserve, 929 Sherwood Forest Road is a refreshing departure from the expected. Mature trees, natural beauty, and an exceptional sense of privacy create a setting that feels worlds away, yet remains just minutes from the heart of Annapolis. It's a rare balance of seclusion, convenience, and character. Inside, the home is every bit as compelling as its surroundings. Soaring vaulted ceilings, expansive windows, and a thoughtfully connected floor plan create an immediate sense of openness, with natural light and wooded views taking center stage. At the heart of the home, a beautifully designed kitchen makes a statement with a quartz waterfall island, a quartz backsplash, and a custom, handcrafted Italian induction range and oven. Envisioned for everyday living and effortless entertaining, the kitchen flows seamlessly into the main gathering spaces, including an inviting family room anchored by a wood-burning fireplace. Multiple decks extend the living experience outdoors. The upper level continues the home's inviting atmosphere, with the primary suite and additional bedrooms offering comfortable accommodations and flexibility for family or other evolving needs. The primary suite brings an entirely different level of comfort to everyday living. A beautifully renovated en-suite bath with dual vanities and an oversized shower creates a spa-like experience, while a spacious walk-in closet adds thoughtful functionality. The true standout is a private balcony overlooking the wooded landscape, where the natural surroundings become an extension of your own personal retreat. With more than 4,600 square feet of finished living space, there's room to entertain, create, unwind, and everything in between. The finished walkout lower level offers additional space for recreation and guests, while a detached custom studio presents an inspiring opportunity for a private office, creative retreat, or something entirely your own. An attached two-car garage adds everyday convenience without compromising the home's distinctive character. Beyond its architectural appeal, the property has benefited from substantial improvements, including a new roof (2020), a new front porch (2022), a new HVAC system (2025), and all-new electrical throughout. The septic system was also professionally pumped in 2025, further reflecting the care and attention invested in the home. 929 Sherwood Forest Road is more than a beautiful place to call home. It's an opportunity to experience Annapolis living from an entirely different perspective.

5 Beds ⋅ 4 Baths

Some homes offer a change of scenery. Others offer an entirely different perspective. Tucked away on 2.75 wooded acres bordering the Sherwood Forest Nature Preserve, 929 Sherwood Forest Road is a refreshing departure from the expected. Mature trees, natural beauty, and an exceptional sense of privacy create a setting that feels worlds away, yet remains just minutes from the heart of Annapolis. It's a rare balance of seclusion, convenience, and character. Inside, the home is every bit as compelling as its surroundings. Soaring vaulted ceilings, expansive windows, and a thoughtfully connected floor plan create an immediate sense of openness, with natural light and wooded views taking center stage. At the heart of the home, a beautifully designed kitchen makes a statement with a quartz waterfall island, a quartz backsplash, and a custom, handcrafted Italian induction range and oven. Envisioned for everyday living and effortless entertaining, the kitchen flows seamlessly into the main gathering spaces, including an inviting family room anchored by a wood-burning fireplace. Multiple decks extend the living experience outdoors. The upper level continues the home's inviting atmosphere, with the primary suite and additional bedrooms offering comfortable accommodations and flexibility for family or other evolving needs. The primary suite brings an entirely different level of comfort to everyday living. A beautifully renovated en-suite bath with dual vanities and an oversized shower creates a spa-like experience, while a spacious walk-in closet adds thoughtful functionality. The true standout is a private balcony overlooking the wooded landscape, where the natural surroundings become an extension of your own personal retreat. With more than 4,600 square feet of finished living space, there's room to entertain, create, unwind, and everything in between. The finished walkout lower level offers additional space for recreation and guests, while a detached custom studio presents an inspiring opportunity for a private office, creative retreat, or something entirely your own. An attached two-car garage adds everyday convenience without compromising the home's distinctive character. Beyond its architectural appeal, the property has benefited from substantial improvements, including a new roof (2020), a new front porch (2022), a new HVAC system (2025), and all-new electrical throughout. The septic system was also professionally pumped in 2025, further reflecting the care and attention invested in the home. 929 Sherwood Forest Road is more than a beautiful place to call home. It's an opportunity to experience Annapolis living from an entirely different perspective.

929 Sherwood Forest Rd, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

$550,000

DIAMOND IN THE ROUGH! 1.90 Acres • Solid Brick Ranch Home • Exceptional Location • Possible Subdivision Potential Location, land, and possibilities! An outstanding opportunity to renovate, reimagine, or potentially redevelop an unusually large residential property consisting of nearly two acres of land in one of the Annapolis area's most desirable and established residential locations. Situated toward the end of Greenbriar Lane, just off Forest Drive and literally minutes from Routes 665, 50, and 97, this spacious brick ranch home offers something increasingly difficult to find in the Annapolis area: a substantial parcel of land, a convenient location, and the flexibility to create something truly special. Built in 1955, the residence has served as a rental property for many years and is ready for a comprehensive cosmetic renovation and modernization. The home also features a substantial 20-by-30-foot addition constructed in the late 1980s, incorporating a large primary bedroom with cathedral ceilings, a small side porch, and a primary bathroom with his-and-hers vanities and closets. According to Anne Arundel County GIS records, the property contains approximately 2,500 square feet across the main level and approximately 1,300 square feet of unfinished space in the lower level. The existing floor plan includes four bedrooms, two full bathrooms, living and dining areas, a family room, kitchen, laundry room, and an enclosed sunroom or three-season room. The house presents an excellent opportunity for someone looking to transform an older, solid residence into an attractive modern home without sacrificing the character and space of an established property. THE LAND The property encompasses approximately 1.90 acres, with an unusually generous amount of frontage along Greenbriar Lane. Previous county mapping information indicates approximately 370 feet of road frontage and a rear property boundary of approximately 360 feet adjoining land owned by the City of Annapolis. Mature trees, established landscaping, and the property's substantial dimensions provide an attractive setting with considerable possibilities for landscaping, outdoor recreation, expansion, or potential additional residential development. The property is zoned R2 Residential, which may offer subdivision or additional building opportunities, subject to applicable zoning, minimum lot sizes, access requirements, utility availability, and county approvals. For a builder, investor, or homeowner interested in maximizing the value of a nearly two-acre parcel, this represents an especially intriguing opportunity. A LOCATION THAT IS HARD TO DUPLICATE Greenbriar Lane is an established residential street conveniently located off Forest Drive, with excellent access to shopping, restaurants, grocery stores, and the many amenities of the Annapolis area. The property is situated across the street from Crab Creek, a tributary of the South River, and is surrounded by neighborhoods featuring attractive custom-built homes, generously sized properties, and numerous waterfront residences. Historic downtown Annapolis, City Dock, the United States Naval Academy, and the city's renowned waterfront restaurants and attractions are approximately four miles away. The surrounding area offers a combination of suburban privacy and convenient access to everything Annapolis has to offer. AN OPPORTUNITY WITH MULTIPLE POSSIBILITIES. Properties offering this combination of acreage, location, road frontage, and potential are increasingly difficult to find in the Annapolis market.The home needs renovation. The location and land are the attractions. The possibilities are what make this property special. The property is offered in its present condition. Acreage, square footage, lot dimensions, zoning, permitted uses, and subdivision potential should be independently verified by prospective purchasers with Anne Arundel County and other applicable authorities.

4 Beds ⋅ 2 Baths

DIAMOND IN THE ROUGH! 1.90 Acres • Solid Brick Ranch Home • Exceptional Location • Possible Subdivision Potential Location, land, and possibilities! An outstanding opportunity to renovate, reimagine, or potentially redevelop an unusually large residential property consisting of nearly two acres of land in one of the Annapolis area's most desirable and established residential locations. Situated toward the end of Greenbriar Lane, just off Forest Drive and literally minutes from Routes 665, 50, and 97, this spacious brick ranch home offers something increasingly difficult to find in the Annapolis area: a substantial parcel of land, a convenient location, and the flexibility to create something truly special. Built in 1955, the residence has served as a rental property for many years and is ready for a comprehensive cosmetic renovation and modernization. The home also features a substantial 20-by-30-foot addition constructed in the late 1980s, incorporating a large primary bedroom with cathedral ceilings, a small side porch, and a primary bathroom with his-and-hers vanities and closets. According to Anne Arundel County GIS records, the property contains approximately 2,500 square feet across the main level and approximately 1,300 square feet of unfinished space in the lower level. The existing floor plan includes four bedrooms, two full bathrooms, living and dining areas, a family room, kitchen, laundry room, and an enclosed sunroom or three-season room. The house presents an excellent opportunity for someone looking to transform an older, solid residence into an attractive modern home without sacrificing the character and space of an established property. THE LAND The property encompasses approximately 1.90 acres, with an unusually generous amount of frontage along Greenbriar Lane. Previous county mapping information indicates approximately 370 feet of road frontage and a rear property boundary of approximately 360 feet adjoining land owned by the City of Annapolis. Mature trees, established landscaping, and the property's substantial dimensions provide an attractive setting with considerable possibilities for landscaping, outdoor recreation, expansion, or potential additional residential development. The property is zoned R2 Residential, which may offer subdivision or additional building opportunities, subject to applicable zoning, minimum lot sizes, access requirements, utility availability, and county approvals. For a builder, investor, or homeowner interested in maximizing the value of a nearly two-acre parcel, this represents an especially intriguing opportunity. A LOCATION THAT IS HARD TO DUPLICATE Greenbriar Lane is an established residential street conveniently located off Forest Drive, with excellent access to shopping, restaurants, grocery stores, and the many amenities of the Annapolis area. The property is situated across the street from Crab Creek, a tributary of the South River, and is surrounded by neighborhoods featuring attractive custom-built homes, generously sized properties, and numerous waterfront residences. Historic downtown Annapolis, City Dock, the United States Naval Academy, and the city's renowned waterfront restaurants and attractions are approximately four miles away. The surrounding area offers a combination of suburban privacy and convenient access to everything Annapolis has to offer. AN OPPORTUNITY WITH MULTIPLE POSSIBILITIES. Properties offering this combination of acreage, location, road frontage, and potential are increasingly difficult to find in the Annapolis market.The home needs renovation. The location and land are the attractions. The possibilities are what make this property special. The property is offered in its present condition. Acreage, square footage, lot dimensions, zoning, permitted uses, and subdivision potential should be independently verified by prospective purchasers with Anne Arundel County and other applicable authorities.

2638 Greenbriar Ln, Annapolis

Listing courtesy of Cottage Street Realty LLC. Contact:

$250,000

Opportunity awaits! Fully updated: Annapolis home being sold in an ONLINE AUCTION. The auction closes Tuesday, November 24, 2026, at 2:00 PM EST. Fully updated three-bedroom, three-full-bath brick-and-siding split-foyer in Cape St. Claire on approximately 0.21 acre. Features include an expansive primary bedroom, an updated kitchen with new appliances, living and dining areas, a lower-level recreation room and third bedroom, laundry and mechanical rooms, a rear deck, driveway parking, central air, a private well, a public sewer, and one fireplace. Original list price: $585,000; opening bid: $250,000. Open house viewing and inspection opportunities: Sunday, November 1, 2:00–4:00 PM; Thursday, November 12, 11:00 AM–1:00 PM; Sunday, November 22, 10:00 AM–12:00 PM EST. Register at Prime Auction Solutions. Review complete auction terms, documents, buyer's premium, deposit requirements, and property documents before bidding. The final price to be set at auction. Excellent investor and investment opportunity. Register and bid your price at Prime Auction Solutions. Contact the agent for more specific information. Watch video.

3 Beds ⋅ 3 Baths

Opportunity awaits! Fully updated: Annapolis home being sold in an ONLINE AUCTION. The auction closes Tuesday, November 24, 2026, at 2:00 PM EST. Fully updated three-bedroom, three-full-bath brick-and-siding split-foyer in Cape St. Claire on approximately 0.21 acre. Features include an expansive primary bedroom, an updated kitchen with new appliances, living and dining areas, a lower-level recreation room and third bedroom, laundry and mechanical rooms, a rear deck, driveway parking, central air, a private well, a public sewer, and one fireplace. Original list price: $585,000; opening bid: $250,000. Open house viewing and inspection opportunities: Sunday, November 1, 2:00–4:00 PM; Thursday, November 12, 11:00 AM–1:00 PM; Sunday, November 22, 10:00 AM–12:00 PM EST. Register at Prime Auction Solutions. Review complete auction terms, documents, buyer's premium, deposit requirements, and property documents before bidding. The final price to be set at auction. Excellent investor and investment opportunity. Register and bid your price at Prime Auction Solutions. Contact the agent for more specific information. Watch video.

721 Fairway Dr, Annapolis

Listing courtesy of Keller Williams Realty. Contact:

$314,900

2 Beds ⋅ 1 Baths

208 Admiral Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

$1,950,000

Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

4 Beds ⋅ 4 Baths

Price improvement!!! Welcome to 146 Duke of Gloucester Street! As you approach the home, a welcoming front porch will greet you, offering a place to sit and take in all that Annapolis has to offer. Nestled in the heart of historic Annapolis, this beautifully appointed 4-bedroom, 3.5-bath residence seamlessly blends timeless charm with modern sophistication. Rich in character and thoughtfully updated throughout, this exceptional home offers an inviting open-concept main level designed for both comfortable living and effortless entertaining. Step inside to discover sun-filled living and dining spaces anchored by a stunning exposed brick fireplace that adds warmth and historic appeal. The modern kitchen is a true centerpiece, featuring stylish finishes, ample cabinetry, and a functional layout perfect for everyday living and hosting guests alike. The second level features three spacious bedrooms filled with natural light from oversized windows, generous closet space, and two beautifully appointed full bathrooms, creating comfortable accommodations for family and guests alike. Occupying the entire third floor, the expansive primary suite serves as a private retreat complete with a luxurious spa-inspired bath designed for relaxation and rejuvenation. Outside, enjoy a charming backyard—an ideal setting for outdoor dining, gardening, or simply unwinding in your own private oasis. Perfectly situated just moments from the waterfront, renowned restaurants, boutique shopping, and the rich history of downtown Annapolis, this home offers a rare opportunity to experience historic living with all the comforts of modern design.

146 Duke Of Gloucester St, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

$824,900

Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

3 Beds ⋅ 2 Baths

Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.

220 West St, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

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