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Investment - Homes for Sale in Annapolis, MD

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  • 290 Hilltop Ln, Annapolis, MD 21403
    290 Hilltop Ln, Annapolis, MD 21403
    290 Hilltop Ln, Annapolis, MD 21403
    /12

    $249,950

    • 2 Beds
    • 1.5 Baths
    • 1,024 Sq Ft

    290 Hilltop Ln, Annapolis, MD 21403

    Open House Sunday, Sept 7, 1-3 PM. Nice Townhome at the Saltaire in Annapolis. 2 bedroom, 1.5 Bath with a fireplace and large back deck. Well priced, vacant, and freshly painted in a popular community. Home is a great investment as a starter home, or rental in an investor friendly community.Across the street from Truxton Park with includes "The Pip Moyer Recreation Center, ball fields,

    Agent Photo

    Susan McConkey

    Sell DC Real Estate

    (410) 936-5499

    290 Hilltop Ln, Annapolis, MD 21403
  • 26 Pleasant St, Annapolis, MD 21401
    26 Pleasant St, Annapolis, MD 21401
    26 Pleasant St, Annapolis, MD 21401
    /34

    $349,900

    • 2 Beds
    • 1 Bath
    • 972 Sq Ft

    26 Pleasant St, Annapolis, MD 21401

    Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife.Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000

    Matthew Wyble Next Step Realty

    26 Pleasant St, Annapolis, MD 21401
  • 14 Jefferson Place, Annapolis, MD 21401
    14 Jefferson Place, Annapolis, MD 21401
    14 Jefferson Place, Annapolis, MD 21401
    /76

    $1,375,000

    • 6 Beds
    • 4 Baths
    • 2,568 Sq Ft

    14 Jefferson Place, Annapolis, MD 21401

    Welcome 14 Jefferson Place located in the highly sought-after President's Hill neighborhood of Downtown Annapolis! This six-bedroom, four-bathroom versatile property offers two side-by-side residences under one roof—perfect as a multi-generational home, short or long-term rental investment, or owner-occupied duplex. Each side of the home features three spacious bedrooms, one full bath, and one

    Jennifer Siska Long & Foster Real Estate, Inc.

    14 Jefferson Place, Annapolis, MD 21401
  • 113 Quiet Waters Place, Annapolis, MD 21403
    113 Quiet Waters Place, Annapolis, MD 21403
    113 Quiet Waters Place, Annapolis, MD 21403
    /48

    $434,900

    • 2 Beds
    • 2.5 Baths
    • 2,178 Sq Ft

    113 Quiet Waters Place, Annapolis, MD 21403

    Welcome to 113 Quiet Waters Place—an updated, brick-front townhome offering the best of Annapolis living. Tucked into a quiet, tree-lined community just minutes from downtown, this home combines convenience, comfort, and flexibility.Inside, you’ll find an open-concept main level with great natural light, a spacious living area, and a well-appointed kitchen that flows seamlessly out to a

    Matthew Wyble Next Step Realty

    113 Quiet Waters Place, Annapolis, MD 21403
  • 1007 Madison Ct, Annapolis, MD 21403
    1007 Madison Ct, Annapolis, MD 21403
    1007 Madison Ct, Annapolis, MD 21403
    /40

    $374,900

    • 3 Beds
    • 2 Baths
    • 900 Sq Ft

    1007 Madison Ct, Annapolis, MD 21403

    ***$5000 seller concession with full price offer by 9/28/25***Charming Townhome Near Downtown Annapolis & the U.S. Naval AcademyWelcome to 1007 Madison Ct, a well-maintained 3-bedroom, 2-bathroom townhome ideally situated just minutes from historic downtown Annapolis and the U.S. Naval Academy. This versatile layout offers comfortable living across three levels.Upstairs,

    SHERRI SPRIGGS Redfin Corp

    1007 Madison Ct, Annapolis, MD 21403
  • 198 Clay St, Annapolis, MD 21401
    198 Clay St, Annapolis, MD 21401
    198 Clay St, Annapolis, MD 21401
    /30

    $429,000

    • 2 Beds
    • 1.5 Baths
    • 902 Sq Ft

    198 Clay St, Annapolis, MD 21401

    Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water views of College Creek and a short stroll to downtown and West Annapolis, where shops, dining, entertainment, and the U.S. Naval Academy are right at your doorstep. The location also provides easy commuter access to Routes 50 and 97 for Washington, D.C., Baltimore, and BWI Airport. Thoughtfully updated in

    Kerry O'Hara Engel & Völkers Annapolis

    198 Clay St, Annapolis, MD 21401
  • 192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    192 Duke of Gloucester St, Annapolis, MD 21401
    /56

    $2,200,000

    • 6 Beds
    • 4 Baths
    • 3,415 Sq Ft

    192 Duke of Gloucester St, Annapolis, MD 21401

    Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare

    Brian Jacobs Coldwell Banker Realty

    192 Duke of Gloucester St, Annapolis, MD 21401
  • 5 Park Place Unit 217, Annapolis, MD 21401
    5 Park Place Unit 217, Annapolis, MD 21401
    5 Park Place Unit 217, Annapolis, MD 21401
    /46

    $699,900

    • 2 Beds
    • 2 Baths
    • 1,343 Sq Ft

    5 Park Place Unit 217, Annapolis, MD 21401

    The recent price adjustment makes this condo an exceptional value in the heart of historic Annapolis! Welcome to luxury living in the highly sought-after Residence at Park Place! This beautifully maintained 2-bedroom, 2-full bath condo offers comfort, convenience, and top-tier amenities — all in a secure, resort-style building. Step inside to find generously sized bedrooms, gorgeous hardwood

    Leslie Bauer Keller Williams Realty

    5 Park Place Unit 217, Annapolis, MD 21401
  • 316 Burnside St Unit 304, Annapolis, MD 21403
    316 Burnside St Unit 304, Annapolis, MD 21403
    316 Burnside St Unit 304, Annapolis, MD 21403
    /34

    $460,000

    • 1 Bed
    • 1 Bath
    • 526 Sq Ft

    316 Burnside St Unit 304, Annapolis, MD 21403

    Beautiful Condo on Spa Creek! PRICE IMPROVEMENT TO $460K. Great investment property, second home or live in downtown Annapolis! Located in the heart of desirable Eastport, this inviting condo offers the best of Annapolis nautically inspired living. 316 Burnside Street has big water views of the serene waters of Spa Creek! This home offers an ideal retreat for those seeking both tranquility in

    Jeannie Miller Long & Foster Real Estate, Inc.

    316 Burnside St Unit 304, Annapolis, MD 21403
  • 14 Oak Ct, Annapolis, MD 21401
    14 Oak Ct, Annapolis, MD 21401
    /2

    $349,900 Coming Soon

    • 0.5 Baths
    • 725 Sq Ft

    14 Oak Ct, Annapolis, MD 21401

    Unique opportunity for investors and entrepreneurs! This versatile commercial/residential property offers exceptional potential for renovation or redevelopment. Formerly used as office space, the building features 2 rooms (ideal as bedrooms or offices) and 1 half bath.Additional features include a rear deck, storage shed, and off-street parking for up to 12 vehicles. The structure is

    Kenneth Chamberlain RE/MAX Concierge Realty

    14 Oak Ct, Annapolis, MD 21401
  • 40 Oak Ct, Annapolis, MD 21401
    40 Oak Ct, Annapolis, MD 21401
    40 Oak Ct, Annapolis, MD 21401
    /15

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,061 Sq Ft

    40 Oak Ct, Annapolis, MD 21401

    Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring

    Gregory Golding ExecuHome Realty

    40 Oak Ct, Annapolis, MD 21401
Maryland Anne Arundel County Annapolis

Real Estate & Homes for Sale in Annapolis, MD

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 32 days on the market compared to the national average of 52 days. The median sale price for homes in Annapolis, MD over the last 12 months is $620,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$620,000
Median Single Family Sale Price
$800,000
Median Townhouse Sale Price
$455,000
Median 2 Bedroom Sale Price
$432,000
Median 1 Bedroom Sale Price
$442,450
Average Price Per Sq Ft
$356
Number of Homes for Sale
274
Last 12 months Home Sales
1,263
Months of Supply
2.60
Median List Price
$630,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%

Popular Home Searches in Annapolis, MD

In Annapolis, waterfront living and historic charm are top priorities, especially near Eastport and the historic district.

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