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Browse All Annapolis MD Historical Properties for Sale

2638 Greenbriar Ln, Annapolis image
2638 Greenbriar Ln, Annapolis $550,000

DIAMOND IN THE ROUGH! 1.90 Acres • Solid Brick Ranch Home • Exceptional Location • Possible Subdivision Potential Location, land, and possibilities! An outstanding opport...

  • 4 Beds
  • 2 Baths
  • MDAA2159546 MLS
127 Porter Dr, Annapolis image
127 Porter Dr, Annapolis $709,900

Nestled in the charming Admiral Heights neighborhood, this beautifully renovated ranch-style home offers a perfect blend of comfort and modern living. With three spacious...

  • 3 Beds
  • 2 Baths
  • MDAA2159916 MLS
795 Fairview Ave Unit 795 C, Annapolis image
795 Fairview Ave Unit 795 C, Annapolis $365,000

This property offers the perfect blend of convenience, comfort, and waterfront community living with a desirable lock-and-leave lifestyle on Back Creek. Relax or enterta...

  • 2 Beds
  • 2 Baths
  • MDAA2159918 MLS
900 Blue Ridge Dr, Annapolis image
900 Blue Ridge Dr, Annapolis $539,900

Welcome to this spacious 3-bedroom, 3-full-bath home in the sought-after, water-privileged community of Cape St. Claire! This home features a versatile layout with room ...

  • 3 Beds
  • 3 Baths
  • MDAA2159812 MLS
1105 Little Magothy Vw, Annapolis image
1105 Little Magothy Vw, Annapolis $299,900

This absolutely charming cottage is on the market for sale for the first time since it was built. The price reflects the condition, but with some elbow grease it will be...

  • 2 Beds
  • 1 Baths
  • MDAA2159732 MLS
173 Williams Dr, Annapolis image
173 Williams Dr, Annapolis $1,749,000

Stress melts away the moment you pull into the driveway. Set on 1.06 peaceful acres in sought-after Admiral Heights, this mid-century modern home offers expansive views o...

  • 4 Beds
  • 4 Baths
  • MDAA2159708 MLS
830 Chester Ave, Annapolis image
830 Chester Ave, Annapolis $1,895,000

This delightful and updated Eastport beauty embodies the true charm of Eastport! The classic style and curb appeal abound, and the updates are already done for you! Centr...

  • 4 Beds
  • 4 Baths
  • MDAA2159664 MLS
2 Murray Ave, Annapolis image
2 Murray Ave, Annapolis $1,149,000

Classic Annapolis Charm Meets Downtown Convenience Built in 1928, this quintessential Annapolis colonial at 2 Murray Avenue puts you in the heart of downtown living. Str...

  • 3 Beds
  • 3 Baths
  • MDAA2159376 MLS
303 Dreams Landing Way Unit 303, Annapolis image
303 Dreams Landing Way Unit 303, Annapolis — Dreams Landing Condo $424,900

Welcome to Dreams Landing, one of Annapolis's most desirable water-privileged condominium communities. Offering beautiful views of the Severn River, this charming two-bed...

  • 2 Beds
  • 1 Baths
  • MDAA2159298 MLS
  • Dreams Landing Condo Bldg.
1858 Burley Rd, Annapolis image
1858 Burley Rd, Annapolis $1,895,000

Experience the timeless charm of waterfront living along the protected waters of Burley Creek, where beautifully landscaped grounds, a distinctive boathouse and exception...

  • 3 Beds
  • 3 Baths
  • MDAA2158646 MLS
1759 Ebling Trl, Annapolis image
1759 Ebling Trl, Annapolis $699,900

Community Amenity Photos Coming Soon! Welcome home to this charming 4-bedroom, 2.5 bath home on a spacious, flat, fenced-in, corner lot in the heart of Epping Forest. T...

  • 4 Beds
  • 3 Baths
  • MDAA2159128 MLS
765 Fairview Ave Unit 765 C, Annapolis image
765 Fairview Ave Unit 765 C, Annapolis — Severn House $399,900

Rarely Available, Beautifully Redesigned 2 Bedroom, 2 Full Bath Condo in Severn House! Enjoy the best of Annapolis waterfront living in this beautifully updated condo, fe...

  • 2 Beds
  • 2 Baths
  • MDAA2159242 MLS
  • Severn House Bldg.
1846 Lindamoor Dr, Annapolis image
1846 Lindamoor Dr, Annapolis $435,000

Damaged by storm. Listed and sold simutaneously.

  • 4 Beds
  • 2 Baths
  • MDAA2159140 MLS
30 Woodlawn Ave, Annapolis image
30 Woodlawn Ave, Annapolis $619,000 ▼

Charming Homewood cottage with numerous recent updates! This property is located on a partially secluded lot bordering city-owned, undevelopable land encompassing the hea...

  • 2 Beds
  • 1 Baths
  • MDAA2159126 MLS
720 Second St, Annapolis image
720 Second St, Annapolis $2,200,000

None

  • MDAA2156998 MLS
1033 Forest Hills Ave, Annapolis image
1033 Forest Hills Ave, Annapolis $525,000

Truly charming 4 bed- & 2 bathroom Cape Cod on almost half acre lot with 2 sheds/ work shops; in Eastport general area. Really nice big porch to enjoy your morning coffee...

  • 4 Beds
  • 2 Baths
  • MDAA2159050 MLS
760 Fairview Ave Unit 760 C, Annapolis image
760 Fairview Ave Unit 760 C, Annapolis — Severn House Condo $600,000

Bring your boat. At Severn House in Eastport, this 3-bedroom, 2-bath condominium comes with a 40-foot boat slip on Back Creek — a rare find in one of Annapolis’s most sou...

  • 3 Beds
  • 2 Baths
  • MDAA2158856 MLS
  • Severn House Condo Bldg.
130 Great Lake Dr, Annapolis image
130 Great Lake Dr, Annapolis $650,000

SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 103 Great Lake Drive, an exciting new opportunity in one of Annapolis' most sought-after w...

  • 4 Beds
  • 3 Baths
  • MDAA2159016 MLS
1925 Fairfax Rd, Annapolis image
1925 Fairfax Rd, Annapolis $700,000

Stunning, updated home on a spacious .6-acre lot located just 2 miles from historic downtown Annapolis. The main level boasts beautifully refinished hardwood floors, upda...

  • 5 Beds
  • 3 Baths
  • MDAA2158848 MLS
3134 Anchorage Dr, Annapolis image
3134 Anchorage Dr, Annapolis $925,000 ▼

Annapolis Renovated Gem A distinctive Annapolis residence where updates, architectural detail, and an enviable waterfront-community setting come together. Welcome to 313...

  • 4 Beds
  • 3 Baths
  • MDAA2158766 MLS
1954 Baltimore Annapolis Blvd, Annapolis image
1954 Baltimore Annapolis Blvd, Annapolis $1,200,000

Set on a beautiful one acre lot with a U shaped driveway, this expansive 4,500 square foot contemporary rancher offers seven bedrooms, three full baths, generous living s...

  • 7 Beds
  • 4 Baths
  • MDAA2158182 MLS
531 Second St, Annapolis image
531 Second St, Annapolis $1,199,000

This charming historic Eastport home was built in the early 1900s and moved to Second Street in 1937. David Fogle, renowned preservationist architect and professor, purc...

  • 2 Beds
  • 3 Baths
  • MDAA2158578 MLS
1952 Forest Dr, Annapolis image
1952 Forest Dr, Annapolis $435,000

Beautiful Move-In Ready Home with Spacious Fenced Backyard! Welcome to this clean, beautiful, and well-maintained 3-bedroom, 2-full-bath home, offering comfortable livin...

  • 3 Beds
  • 2 Baths
  • MDAA2158428 MLS
784 Fairviw Av Unit E, Annapolis image
784 Fairviw Av Unit E, Annapolis $539,000

None

  • 2 Beds
  • 1 Baths
  • MDAA2158754 MLS
208 Admiral Dr, Annapolis image
208 Admiral Dr, Annapolis $314,900 ▼

None

  • 2 Beds
  • 1 Baths
  • MDAA2158706 MLS
property image
1024 College Pkwy E, Annapolis $1,000

Accepting offers until 11/16/26. See engineering plans. This complex on ±23 acres allows a congregation to occupy the church while building a larger facility on the addit...

  • MDAA2158542 MLS
3124 Starboard Dr, Annapolis image
3124 Starboard Dr, Annapolis $1,690,000 ▼

A Builder’s Personal Residence | A Signature Annapolis Home A rare opportunity to own the personal residence of a builder and an interior designer, whose expertise and...

  • 5 Beds
  • 4 Baths
  • MDAA2158448 MLS
1161 Green Holly Dr, Annapolis image
1161 Green Holly Dr, Annapolis $525,000

Welcome to this spacious Colonial in the sought after water privileged community of Cape St. Claire. Step inside to a bright and inviting main level filled with natural l...

  • 3 Beds
  • 3 Baths
  • MDAA2157576 MLS
19 Dean St, Annapolis image
19 Dean St, Annapolis $725,000 ▼

OPEN Saturday, 10/24, 1-3PM! Charming Historic District living in an enviable location! This inviting rowhouse is tucked away on picturesque Dean Street in the heart of d...

  • 2 Beds
  • 1 Baths
  • MDAA2158200 MLS
9 Hull Ave, Annapolis image
9 Hull Ave, Annapolis $1,200,000

OPEN Sunday 1-4pm! This lovely home in the sought after community of BAY RIDGE sits on a level 50x200ft lot just 4 houses from the Bay, and 2 blocks from the amazing Bay ...

  • 3 Beds
  • 3 Baths
  • MDAA2158082 MLS
827 Bay Ridge Ave, Annapolis image
827 Bay Ridge Ave, Annapolis $869,000

Enjoy the convenience and charm of Eastport living at 827 Bay Ridge, just a short walk to local restaurants, shops, marinas, parks, and downtown Annapolis. This updated a...

  • 3 Beds
  • 3 Baths
  • MDAA2157996 MLS
1230 Hilltop Dr, Annapolis image
1230 Hilltop Dr, Annapolis $550,000

Welcome home to Cape St. Claire! Offering plenty of space inside and out, this beautifully updated rancher features a fully finished basement, five bedrooms, two full bat...

  • 5 Beds
  • 2 Baths
  • MDAA2158270 MLS
416 Walnut Dr, Annapolis image
416 Walnut Dr, Annapolis $574,990 ▼

Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the communi...

  • 3 Beds
  • 3 Baths
  • MDAA2157998 MLS
102 Melvin Ave, Annapolis image
102 Melvin Ave, Annapolis $2,199,000 ▼

Welcome to one of Annapolis’ most sought-after water-access communities, where timeless character meets extensive, thoughtful improvements. Since 2022, the sellers have i...

  • 3 Beds
  • 3 Baths
  • MDAA2157260 MLS
1518 Winchester Rd, Annapolis image
1518 Winchester Rd, Annapolis $799,000

Listed and sold simultaneously

  • 4 Beds
  • 3 Baths
  • MDAA2157274 MLS
308 Halsey Rd, Annapolis image
308 Halsey Rd, Annapolis $895,000

Welcome to this beautifully renovated 3-bedroom, 2.5-bath home in the highly sought-after Admiral Heights neighborhood. This home has undergone a stunning, custom renovat...

  • 3 Beds
  • 3 Baths
  • MDAA2108722 MLS
128 Market St, Annapolis image
128 Market St, Annapolis $815,000

Historic Annapolis, with the city’s best right outside your door. Just two blocks to Main Street, with restaurants, shops, the waterfront and the Naval Academy all just m...

  • 2 Beds
  • 2 Baths
  • MDAA2157964 MLS
98 Monticello Ave, Annapolis image
98 Monticello Ave, Annapolis $975,000 ▼

Welcome to 98 Monticello Avenue, a charming Murray Hill residence that captures the character and ease of the Annapolis lifestyle. From the moment you step inside, a welc...

  • 3 Beds
  • 3 Baths
  • MDAA2155160 MLS
391 Hilltop Ln, Annapolis image
391 Hilltop Ln, Annapolis $540,000 ▼

Like a new look, new windows, new appliances, new HVAC systems, new Central unit, new cabinets, fully updated from top to bottom. Nestled in the serene community of Pr...

  • 5 Beds
  • 2 Baths
  • MDAA2157950 MLS
356 Severn Rd, Annapolis image
356 Severn Rd, Annapolis $799,900

Opportunity awaits in the sought-after private, gated waterfront community of Epping Forest on the Severn River! If you have been looking for an opportunity to call Eppin...

  • 4 Beds
  • 2 Baths
  • MDAA2154280 MLS
1130 Mainsail Dr, Annapolis image
1130 Mainsail Dr, Annapolis $949,000

Annapolis Turnkey Luxury Colonial - Coastal Elegance, Timeless Charm & Exceptional Privacy in Anchorage: Welcome to 1130 Mainsail Drive, a beautifully renovated Colonial...

  • 3 Beds
  • 3 Baths
  • MDAA2157844 MLS
21 Woodlawn Ave, Annapolis image
21 Woodlawn Ave, Annapolis $859,000

NEWLY UPDATED! NEW BATHROOMS, GARAGE, and A BONUS 3rd FLOOR ROOM. Boasting 1,670 sq. ft. of finished historic charm, this 1905 Homewood treasure sits on a rare, oversized...

  • 3 Beds
  • 2 Baths
  • MDAA2157812 MLS
312 Severn Unit W308, Annapolis image
312 Severn Unit W308, Annapolis — The Tecumseh $765,000

Welcome to 312 Severn Avenue, Unit W308—a rarely available two-story, two-bedroom, two-bath condominium at The Tecumseh, one of Eastport’s most distinctive waterfront com...

  • 2 Beds
  • 2 Baths
  • MDAA2149960 MLS
  • The Tecumseh Bldg.
219 King George St, Annapolis image
219 King George St, Annapolis $1,700,000

Experience the ultimate walkable lifestyle in the heart of Downtown Annapolis with this charming traditional home in the Historic District, where timeless character meets...

  • 3 Beds
  • 3 Baths
  • MDAA2157512 MLS
1030 Mountain Top Dr, Annapolis image
1030 Mountain Top Dr, Annapolis $500,000 ▼

Beautifully appointed rancher in the sought-after Cape St. Claire community of Annapolis, just one block from the Magothy River and the Chesapeake Bay! Step inside to a s...

  • 3 Beds
  • 3 Baths
  • MDAA2142866 MLS
100 Conduit St, Annapolis image
100 Conduit St, Annapolis $1,249,000

An exceptional offering in the heart of the Annapolis Historic District, 100 Conduit Street captures the timeless elegance and effortless lifestyle that make downtown Ann...

  • 4 Beds
  • 3 Baths
  • MDAA2157442 MLS
626 Edwards Rd, Annapolis image
626 Edwards Rd, Annapolis $574,900 ▼

Price Improvement Incredibly maintained home in the sought-after water-privileged community of Beechwood on the Burley. This two-level home offers comfortable living, ...

  • 4 Beds
  • 2 Baths
  • MDAA2157270 MLS
755 Fairview Ave Unit 755 D, Annapolis image
755 Fairview Ave Unit 755 D, Annapolis — Severn House Condo $479,900 ▼

Welcome Home! YOU DON'T WANT TO MISS THIS GREAT NEWS!! The seller's loan is ASSUMABLE @ 2.875 % to qualified buyers.This beautifully Renovated Eastport Marina Condo with...

  • 3 Beds
  • 2 Baths
  • MDAA2157174 MLS
  • Severn House Condo Bldg.
327 Beach Dr, Annapolis image
327 Beach Dr, Annapolis $850,000

Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfron...

  • 4 Beds
  • 3 Baths
  • MDAA2157350 MLS
211 Mckendree Ave, Annapolis image
211 Mckendree Ave, Annapolis $1,125,000

Situated on one of the best lots in Homewood, seconds from downtown Annapolis, this charming home must be seen to appreciate it. With 5 bedrooms, 3 full bathrooms, and ov...

  • 5 Beds
  • 3 Baths
  • MDAA2157084 MLS

Annapolis Historical Real Estate

Our website features the best real estate search for historical properties available in Annapolis and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

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