Downtown Annapolis Homes

/40
$1,750,000
- 4 Beds
- 2.5 Baths
- 2,550 Sq Ft
146 Prince George St, Annapolis, MD 21401

Own a Piece of Annapolis History – Don’t miss this rare opportunity to own an exquisitely restored historic home in the heart of downtown Annapolis. Welcome to The Quarter Deck on Prince George—a 4-bedroom, 2.5-bathroom retreat that blends timeless charm with modern convenience, all while boasting a proven short-term rental history. Financials are available upon request. This is the perfect

Rob Carter Douglas Realty, LLC

146 Prince George St, Annapolis, MD 21401
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Timothy House & Gardens

1-3 Beds

29 W Washington St, Annapolis, MD 21401

29 W Washington St, Annapolis, MD 21401
/25
$749,900 Sold May 02, 2025
- 1,590 Sq Ft
- $472/SF
- 0 Days On Market
- 1 Bed
- 2 Baths
- Built 2007
66 Franklin St Unit 10, Annapolis, MD 21401

Looking for the perfect downtown Annapolis condo? You've found it! Beautifully update and filled with natural light, offering a unique layout that flows perfectly. The gourmet kitchen is chef-ready and is ideally situated to the living area for entertaining your guests. The gorgeous primary bedroom is large, open, offers an updated bathroom and walk in closet. Although technically "one bedroom"

Joseph Wallman Coldwell Banker Realty

66 Franklin St Unit 10, Annapolis, MD 21401

/11
Not Listed For Sale
- 6 Beds
- 5 Baths
- 3,186 Sq Ft
179 Prince George St, Annapolis, MD 21401

179 Prince George St, Annapolis, MD 21401

/59
$2,150,000 Coming Soon
- 4 Beds
- 3.5 Baths
- 2,833 Sq Ft
19 Thompson St, Annapolis, MD 21401

This absolutely stunning 4-bedroom, 2.5-bath home in the heart of Murray Hill has just undergone a full-scale renovation by a top-tier local architect, designer, and builder—resulting in a true magazine-worthy masterpiece. Thoughtfully reimagined to blend timeless style with modern functionality, the home features a reconfigured floor plan, a chef’s kitchen with custom cabinetry, marble

Elizabeth Dooner Coldwell Banker Realty

19 Thompson St, Annapolis, MD 21401
/11
$3,450 per month
- 3 Beds
- 2.5 Baths
- 1,944 Sq Ft
- Townhouse for Rent
80 Charles St, Annapolis, MD 21401

JUST A BLOCK TO SPA CREEK AND ACTON COVE PARK. This 3 level home with 3 BR, 2.5 BA, located in the historic district has upgraded appliances, granite counter tops and includes a washer and dryer. The home has a rear deck and yard. Third level finished attic loft. All checks made payable to Kerry Muse Property Management. Listing agent runs credit.

Julie Harris KD Realty Inc

80 Charles St, Annapolis, MD 21401
/41
$1,425,000 Sold Apr 29, 2025
- 2,089 Sq Ft
- $682/SF
- 5 Days On Market
- 4 Beds
- 3.5 Baths
- Built 1900
144 Charles St, Annapolis, MD 21401

Timeless Elegance in the Heart of Historic Annapolis. Tucked away on one of Annapolis’ most charming streets, this circa-1900 home blends historic character with thoughtful, high-end renovations. Painted deep navy cedar shingles with crisp white trim, this unique home sits gracefully along a brick-paved sidewalk, just steps from the waterfront, the U.S. Naval Academy, and downtown’s best

Kate Hopkins Coldwell Banker Realty

144 Charles St, Annapolis, MD 21401

/30
Est $1,437,671 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 2,000 Sq Ft
33 East St Unit 1, Annapolis, MD 21401

33 East St Unit 1, Annapolis, MD 21401

/84
$1,725,000 Under Contract
- 4 Beds
- 2.5 Baths
- 3,160 Sq Ft
33 Southgate Ave, Annapolis, MD 21401

Charming Murray Hill Gem in the Heart of Annapolis!Discover this classic Murray Hill residence, perfectly situated on sought-after Southgate Avenue. This beautifully maintained home is move-in ready and offers timeless charm with modern updates.Step onto the inviting front porch and take in the tree-lined street before entering a home filled with character—hardwood floors, nine-foot ceilings,

Georgie Berkinshaw Coldwell Banker Realty

33 Southgate Ave, Annapolis, MD 21401
/5
$1,600 per month
- 1 Bed
- 1 Bath
- 600 Sq Ft
- Townhouse for Rent
41 Dean St, Annapolis, MD 21401

The bottom half of a rowhome has a front garden full of veggies and herbs; living room big enough for two couches, two desks, and a coffee table; bedroom with two closets; bathroom with a shower (no tub) and toilet; combined kitchen-dining room; and a grassy fenced-in backyard with patio. Almost all new appliances, including gas stove. It does not come furnished.The location could not be

41 Dean St, Annapolis, MD 21401
/56
$1,260,000 Sold Mar 31, 2025
- 1,820 Sq Ft
- $692/SF
- 2 Days On Market
- 3 Beds
- 3.5 Baths
- Built 2008
22 Dean St Unit 2, Annapolis, MD 21401

This exquisite three-bedroom, three-and-a-half-bath townhome-style condo in Historic Annapolis offers not just luxury and charm but also the rare convenience of two dedicated parking spots in the attached garage. Nestled in the heart of downtown, this elegant property features an eye-catching brick facade and blends sophisticated design with the allure of waterfront living just a short stroll

Teresa Klem Long & Foster Real Estate, Inc.

22 Dean St Unit 2, Annapolis, MD 21401

/56
Est $1,165,976 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,873 Sq Ft
66 Franklin St Unit 411, Annapolis, MD 21401

66 Franklin St Unit 411, Annapolis, MD 21401

/29
$1,175,000
- 2 Beds
- 1.5 Baths
- 1,656 Sq Ft
179 Green St, Annapolis, MD 21401

Experience the Essence of Annapolis Charm at 179 Green StreetNestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted

David Yee Long & Foster Real Estate, Inc.

179 Green St, Annapolis, MD 21401
/22
$2,500 per month
- 2 Beds
- 1 Bath
- 900 Sq Ft
- House for Rent
101 Charles St, Annapolis, MD 21401

The perfect in-town residence. This sunny apartment has a great floor plan and a nice kitchen with a large eat-at island that is open to the living room. Top level loft can be used as a bedroom or a great office. Separate entrances, utilities, washers and dryers conveniently located in the unit. Beautiful waterfront park with water access is one block away and Main Street is 3 blocks away!

Merrie Louise Raynolds TTR Sotheby's International Realty

101 Charles St, Annapolis, MD 21401
/95
$1,495,000 Sold Mar 31, 2025
- 4,192 Sq Ft
- $357/SF
- 84 Days On Market
- 6 Beds
- 3 Baths
- Built 1915
29 Southgate Ave, Annapolis, MD 21401

A Rare Opportunity Awaits at 29 Southgate, now priced at 1,549,900 & open this weekend.Every so often, a home comes along that stops people in their tracks. For those who’ve admired this Murray Hill icon, now is your chance to make it yours. Built in 1915, this Grand Dame blends timeless elegance with modern potential. Set on a 40' x 140' lot, the property features a repointed retaining wall,

Yael Beckman Coldwell Banker Realty

29 Southgate Ave, Annapolis, MD 21401

/40
Est $943,040 Not Listed For Sale
- 2 Beds
- 2.5 Baths
- 1,584 Sq Ft
66 Franklin St Unit 304, Annapolis, MD 21401

66 Franklin St Unit 304, Annapolis, MD 21401

/21
$225,000
- 3 Beds
- 1.5 Baths
- 1,037 Sq Ft
63 Town Pines Ct, Annapolis, MD 21401

Welcome to the heart of downtown Annapolis, where city living meets historic charm! This 3-bedroom, 1 Full and 1 Half-bathroom, townhome offers an incredible opportunity to be just 2 blocks away from the Capitol building, shopping, restaurants, and the picturesque waterfront filled with boats. Convenience is key with parking included, allowing you to explore the vibrant downtown area with ease.

Martin Tippet ExecuHome Realty

63 Town Pines Ct, Annapolis, MD 21401
/31
$4,600 per month
- 4 Beds
- 3.5 Baths
- 1,990 Sq Ft
- Townhouse for Rent
151 Duke of Gloucester St, Annapolis, MD 21401

Absolutely Gorgeous Historic Annapolis home , full of the charm and style yet completely restored with all of the modern conveniences . Close to everything 1 block from main street.....City Dock, Bar, Restaurants...... across from City Hall, Close to spa creek ..... Come sit back and enjoy the Annapolis life style.Pets allowed with non refundable pet fee of $250 per Pet and $50 a month pet rent

Heather Edmond Keller Williams Flagship

151 Duke of Gloucester St, Annapolis, MD 21401
/50
$900,000 Sold Mar 27, 2025
- 1,256 Sq Ft
- $717/SF
- 5 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1918
102 South St, Annapolis, MD 21401

A truly rare and spectacular home just completed and totally renovated in the heart of Annapolis' Historic District! It is like having a brand new townhouse in Downtown Annapolis. Banks of all new windows throughout the house highlight the sleek, beautiful finishes in the sunny, open spaces. Worry free living with the all new appliances, HVAC system, 2.5 baths, plumbing, electric and wood

Alex Tower Sears TTR Sotheby's International Realty

102 South St, Annapolis, MD 21401

/106
Est $2,126,445 Not Listed For Sale
- 4 Beds
- 4.5 Baths
- 4,053 Sq Ft
5 S Acton Place, Annapolis, MD 21401

5 S Acton Place, Annapolis, MD 21401

/50
$1,495,000
- 4 Beds
- 4 Baths
- 3,100 Sq Ft
138 Charles St, Annapolis, MD 21401

First time on the market in 40 years! This is a rare and special opportunity to own a detached home with both a garage and driveway in The Historic District of Downtown Annapolis. This elegant home seamlessly blends gorgeous original details with modern updates on three finished levels. Wrought iron fence frames the home which is ideally set back on the lot and leads to the inviting and spacious

Alex Tower Sears TTR Sotheby's International Realty

138 Charles St, Annapolis, MD 21401
/38
$905,000 Sold Mar 27, 2025
- 1,650 Sq Ft
- $548/SF
- 25 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1870
170 Green St, Annapolis, MD 21401

Welcome to the epitome of Annapolis charm! Nestled in the heart of the historic district, this stunning 1870 Victorian home—with its historic plaque—offers an extraordinary blend of period elegance and modern comfort. Located just steps from the waterfront and Annapolis Elementary, 170 Green Street immerses you in the vibrant, cultural essence of downtown Annapolis.This home is a

Nicole Callender Keller Williams Realty Delmarva

170 Green St, Annapolis, MD 21401

/32
Est $647,855 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,138 Sq Ft
5 Maryland Ave Unit 5, Annapolis, MD 21401

5 Maryland Ave Unit 5, Annapolis, MD 21401

/32
$1,200,000
- 4 Beds
- 2.5 Baths
- 2,322 Sq Ft
160 Green St, Annapolis, MD 21401

Step into a piece of Annapolis history with the Philip Clayton House, a cherished landmark dating back to 1834. Perfectly situated within walking distance to the City Dock, U.S. Naval Academy, and the vibrant shops and restaurants of Downtown Annapolis, this residence blends timeless character with everyday convenience. Over nearly two centuries, the home has undergone thoughtful renovations and

Lucie Dulin Compass

160 Green St, Annapolis, MD 21401
/39
$600,000 Sold Mar 25, 2025
- 1,188 Sq Ft
- $505/SF
- 1 Day On Market
- 3 Beds
- 2 Baths
- Built 1895
17 Lafayette Ave, Annapolis, MD 21401

Welcome to 17 Lafayette Avenue, a stunning three-bedroom, two-bathroom end-unit townhome nestled in the vibrant Arts District of Downtown Annapolis. Boasting a complete renovation in 2022. This impeccably maintained home seamlessly blends modern convenience with timeless charm. A welcoming covered entryway with stone accents leads you to a bright and airy open-concept floor plan. The family room

Carol Snyder Monument Sotheby's International Realty

17 Lafayette Ave, Annapolis, MD 21401

/30
Est $707,258 Not Listed For Sale
- 2 Beds
- 1.5 Baths
- 1,026 Sq Ft
28 Fleet St, Annapolis, MD 21401

28 Fleet St, Annapolis, MD 21401

/49
$1,475,000
- 4 Beds
- 3 Baths
- 2,649 Sq Ft
165 King George St, Annapolis, MD 21401

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will

Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

165 King George St, Annapolis, MD 21401
/54
$815,000 Sold Mar 17, 2025
- 2,770 Sq Ft
- $294/SF
- 9 Days On Market
- Studio
- Built 1900
263 Hanover St, Annapolis, MD 21401

Location, location, location. Great investment opportunity.One block off of King George Street you will find 263-265 Hanover Street. 3 unit building. A prime, quiet location next to the United States Naval Academy. This stately building is home to three exceptionally-large, light-filled, full-floor, one-bedroom apartments. The units have separate living rooms, dining rooms and kitchens.

Ginna Quinn Coldwell Banker Realty

263 Hanover St, Annapolis, MD 21401

/36
Est $1,399,095 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 2,280 Sq Ft
22 South St, Annapolis, MD 21401

22 South St, Annapolis, MD 21401

/49
$1,475,000
- Studio
- 2,649 Sq Ft
165 King George St, Annapolis, MD 21401

Back on the market with a DRAMATIC price improvement!! Welcome to your truly turnkey 3-unit investment property in the HEART of Annapolis!! All 3 units come FULLY furnished, down to the spoons and forks!! Literally STEPS away from the Naval Academy main gate and downtown Annapolis!! Unit 1 is a 1 bedroom, 1 bathroom unit with a family room and a full eat-in kitchen w/ dishwasher. You will

Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

165 King George St, Annapolis, MD 21401
/66
$1,350,000 Sold Mar 04, 2025
- 2,434 Sq Ft
- $555/SF
- 4 Days On Market
- 3 Beds
- 2.5 Baths
- Built 1875
163 Prince George St, Annapolis, MD 21401

Nestled on one of the most picturesque and sought-after streets in Historic Annapolis, this stunning 3-bedroom, 2.5-bathroom home beautifully blends 19th-century charm with modern-day luxury. With no direct neighbors in front or behind, the home feels remarkably open and offers a sense of privacy that’s rare in this prime location. Step inside and be captivated by meticulously preserved historic

Teresa Klem Long & Foster Real Estate, Inc.

163 Prince George St, Annapolis, MD 21401

/34
Est $1,239,303 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,806 Sq Ft
60 Cornhill St, Annapolis, MD 21401

60 Cornhill St, Annapolis, MD 21401

/48
$1,549,000
- 4 Beds
- 3.5 Baths
- 3,042 Sq Ft
146 Duke of Gloucester St, Annapolis, MD 21401

Experience Historic Charm & Modern Elegance in the Heart of Annapolis.Nestled in the heart of downtown Annapolis, this stunning historic Federal-style home offers the perfect blend of timeless character and modern sophistication. Located on the iconic Duke of Gloucester Street, this residence places you just steps away from the waterfront, top-tier dining, boutique shopping, and the rich history

Phil Gerdes Real Broker, LLC - Annapolis

146 Duke of Gloucester St, Annapolis, MD 21401
/57
$1,550,000 Sold Feb 26, 2025
- 2,760 Sq Ft
- $562/SF
- 0 Days On Market
- Studio
- Built 1900
107 Conduit St, Annapolis, MD 21401

The historic Smith House is a charming 4-unit home in the heart of downtown Annapolis, steps from Main Street and in the city's most desirable area. The home is the perfect turnkey opportunity for owner-occupy, long-term, and short-term rentals. Units 2, 3 and 4 fully furnished and fully built business ready for immediate income. The property generates a remarkable annual income through

Scott Schuetter Berkshire Hathaway HomeServices PenFed Realty

107 Conduit St, Annapolis, MD 21401

/45
Est $1,483,544 Not Listed For Sale
- 4 Beds
- 4 Baths
- 2,732 Sq Ft
57 Richards Ln, Annapolis, MD 21401

57 Richards Ln, Annapolis, MD 21401

/46
$3,495,000
- 3 Beds
- 2.5 Baths
- 2,621 Sq Ft
9 Shipwright St, Annapolis, MD 21401

Quintessential downtown Annapolis waterfront home on the sparkling waters of Spa Creek! This amazing property combines the best of both worlds; the charming historic feel of a downtown Annapolis home with the premier waterfront lifestyle that every resident is looking for. Nestled on a quiet street, this home is the perfect size for an easy to own, lock up and go property. With 3 bedrooms and

Brad Kappel TTR Sotheby's International Realty

9 Shipwright St, Annapolis, MD 21401
/50
$2,900,000 Sold Feb 18, 2025
- 5,911 Sq Ft
- $491/SF
- 10 Days On Market
- 5 Beds
- 7 Baths
- Built 1776
40 Cornhill St, Annapolis, MD 21401

Two perfect 18-century homes being sold together. 40 and 38 Cornhill is an exquisite residence in the heart of Downtown Annapolis. Flawlessly renovated and updated with extreme attention to detail, the house has outstanding space and a wonderfully versatile layout for today's lifestyle. No expense was spared in creating and preserving each gorgeous room with beautiful custom finishes on all 4

Alex Tower Sears TTR Sotheby's International Realty

40 Cornhill St, Annapolis, MD 21401

/6
Est $1,808,134 Not Listed For Sale
- 5 Beds
- 3.5 Baths
- 2,762 Sq Ft
92 Duke of Gloucester St, Annapolis, MD 21401

92 Duke of Gloucester St, Annapolis, MD 21401

/37
$2,300,000
- 4 Beds
- 2.5 Baths
- 4,404 Sq Ft
41 Cornhill St, Annapolis, MD 21401

Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood burning Fireplace; a Two Room Parlor, also with a

Lorain Shore Expert Realty, LLC.

41 Cornhill St, Annapolis, MD 21401
/56
$925,000 Sold Feb 11, 2025
- 1,800 Sq Ft
- $514/SF
- 6 Days On Market
- 2 Beds
- 2.5 Baths
- Built 2007
66 Franklin St Unit 418, Annapolis, MD 21401

Elegant Dual-Level Living with Exceptional Privacy. Experience modern luxury in this stunning 2-level condo, ideally situated in the heart of Downtown Annapolis. Just steps from Spa Creek and the water taxi, this highly sought-after residence at Acton’s Landing blends historic charm with contemporary design.With direct access to Franklin Street, you’ll bypass long hallways and elevators,

Jennifer McCormick Engel & Völkers Annapolis

66 Franklin St Unit 418, Annapolis, MD 21401

Showing Results 1 - 40, Page 1 of 18

Maryland Annapolis Downtown Annapolis

Learn more about living in Downtown Annapolis

Home Trends in Downtown Annapolis, MD

On average, homes in Downtown Annapolis, Annapolis sell after 17 days on the market compared to the national average of 49 days. The median sale price for homes in Downtown Annapolis, Annapolis over the last 12 months is $945,000, up 6% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$945,000

Median Single Family Sale Price

$1,510,000

Median Townhouse Sale Price

$902,500

Median 2 Bedroom Sale Price

$950,000

Median 1 Bedroom Sale Price

$546,449

Average Price Per Sq Ft

$554

Number of Homes for Sale

Last 12 months Home Sales

Months of Supply

3.10

Median List Price

$1,095,250

Median Change From 1st List Price

Median Home Sale Price YoY Change

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