20

Annapolis, MD Open Houses

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  • /67

    $579,900

    Open Sat 1PM - 3PM $15K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,237 Sq Ft

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403

    Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting,

    Agent Photo

    Lorna Kaim

    Compass

    (410) 584-3520

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
  • /96

    $650,000

    Open Sun 1PM - 3PM $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403

    Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community

    Agent Photo

    Lorna Kaim

    Compass

    (443) 543-8416

    2108 Chesapeake Harbour Dr Unit 201, Annapolis, MD 21403
  • /87

    $940,000

    Open Sat 12PM - 2PM $110K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,800 Sq Ft

    3249 Arundel on The Bay Rd, Annapolis, MD 21403

    VIRTUAL TOUR: ***PRICE DROPPED TO SELL, seller is moving away and just wants the home sold. Property appraised for $1,049,000 January 2026 so this is a great chance to walk into equity! Buyer may keep all furnishings if desired, all items in garage will be removed prior to sale. Welcome to 3249 Arundel on the Bay Road — where coastal charm meets timeless character in one of Annapolis’ most

    Justin Walker Keller Williams Flagship

    3249 Arundel on The Bay Rd, Annapolis, MD 21403
  • /43

    $1,990,000

    New Construction Open Sat 1PM - 3PM
    • 4 Beds
    • 4 Baths
    • 4,200 Sq Ft

    400 Jefferson St, Annapolis, MD 21403

    Nestled in the heart of historic Eastport Annapolis, this coastal craftsman has been extensively remodeled, offering a perfect blend of classic Eastport charm and craftman finishes. The home is set on a generously sized lot, providing abundant green space, and fresh sod. Premium exterior finishes include an inviting front porch, James Hardi siding and Anderson 400 windows. Inside, the home

    Brian Jacobs Coldwell Banker Realty

    400 Jefferson St, Annapolis, MD 21403
  • /99

    $3,195,000

    Open Sun 1PM - 3PM
    • 6 Beds
    • 4.5 Baths
    • 6,639 Sq Ft

    1588 Eaton Way, Annapolis, MD 21401

    Welcome to 1588 Eaton Way, an extraordinary, waterfront Chesapeake Bay retreat offering the very best of Annapolis living. Located in the highly coveted Downs on the Severn neighborhood, this custom California Deck‐style home spans 7,000+ square feet on 2 private acres with deep‐water access (6+ ft MLW) and stunning views of Clements Creek. Designed as a true waterfront estate, this home blends

    Jeannie Miller Long & Foster Real Estate, Inc.

    1588 Eaton Way, Annapolis, MD 21401
  • /55

    $1,895,000

    Open Sat 1PM - 3PM
    • 8 Beds
    • 5.5 Baths
    • 7,389 Sq Ft

    234 Meadowgate Dr, Annapolis, MD 21409

    Set on nearly two serene acres, this stately brick-front colonial commands attention with timeless curb appeal. Inside, a formal living room and a separate office or study offer refined spaces for quiet pursuits, while the expansive great room and adjoining den are connected by a dramatic double-sided fireplace, one of four throughout the home. The partially open layout flows with intention,

    Jeff Lockard TTR Sotheby's International Realty

    234 Meadowgate Dr, Annapolis, MD 21409
  • /75

    $1,250,000

    Open Sun 12PM - 2PM
    • 5 Beds
    • 4.5 Baths
    • 4,692 Sq Ft

    128 Stilly Way, Annapolis, MD 21403

    Move-in ready and beautifully upgraded, welcome to 128 Stilly Way — a barely lived-in showpiece located in Annapolis’ sought-after Parkside Preserve community. Built in 2024 and offered in pristine condition, this exceptional residence combines the advantages of brand-new construction with the convenience of immediate enjoyment. No builder delays, no design center decisions, and no construction

    Dee Dee McCracken Coldwell Banker Realty

    128 Stilly Way, Annapolis, MD 21403
  • /41

    $569,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 4 Baths
    • 2,020 Sq Ft

    2638 Foremast Aly, Annapolis, MD 21401

    Welcome to 2638 Foremast Aly in Annapolis - a beautifully appointed townhome offering stylish finishes, functional living space, and an unbeatable location! This spacious home features 3 bedrooms, 2 full baths, and 2 half baths, thoughtfully designed across multiple levels with tall ceilings and gorgeous hardwood floors that create a bright, open feel throughout.The heart of the home is the

    Caroline Paper Next Step Realty

    2638 Foremast Aly, Annapolis, MD 21401
  • /78

    $3,750,000

    Open House 7/02
    • 4 Beds
    • 4.5 Baths
    • 3,036 Sq Ft

    5 Market Quay, Annapolis, MD 21401

    Welcome home. Perfectly positioned at the end of Market Street, this rare waterfront residence offers an exceptional blend of privacy, design, and lifestyle. Located within an intimate six residence enclave, this fully reimagined contemporary brick townhome captures sweeping views of Spa Creek from every level, delivering a front row experience to Annapolis’ most iconic moments, from the Blue

    Kathleen Moore Engel & Völkers Annapolis

    5 Market Quay, Annapolis, MD 21401
  • /50

    $995,000

    Open Sun 11AM - 1PM $55K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 6,027 Sq Ft

    704 Caleb Ln, Annapolis, MD 21401

    704 Caleb Lane is beautifully maintained and loaded with recent updates in the highly sought-after, amenity-rich Kingsport community of Annapolis. The spacious, open floor plan is enhanced by the many value-added updates in the home, including the renovated kitchen, roof (2022), HVAC systems (2025 and 2022), and water heater (2022). The light-filled walk-out lower level is a complete in-law/au

    Alex Tower Sears TTR Sotheby's International Realty

    704 Caleb Ln, Annapolis, MD 21401
  • /42

    $464,000

    Open Sat 12PM - 2PM
    • 3 Beds
    • 1 Bath
    • 1,368 Sq Ft

    410 Walnut Dr, Annapolis, MD 21403

    A CHERISHED FAMILY CLASSIC IN WATERFRONT HILLSMERE ESTATES! 410 Walnut Road presents a rare opportunity in one of Annapolis’s most coveted water-privileged communities. Lovingly maintained by the same family, this home serves as a beautiful foundation for your future memories and personal design touches. Three bedrooms with a traditional layout which include rich hardwood flooring, adding a layer

    Linda Pelton Taylor Properties

    410 Walnut Dr, Annapolis, MD 21403
  • /2

    $1,500,000

    Open Sun 1PM - 3PM Coming Soon
    • 4 Beds
    • 3.5 Baths
    • 3,159 Sq Ft

    107 Monticello Ave, Annapolis, MD 21401

    Nestled in the highly coveted Murray Hill neighborhood, one of Annapolis' most picturesque enclaves, this exceptional 1925 Craftsman masterpiece effortlessly blends historic charm with sophisticated modern luxury. Rich in architectural character and thoughtfully enhanced with extensive renovations, this remarkable residence offers an unparalleled lifestyle defined by elegance, convenience, and

    Alexandra Ryan EXP Realty, LLC

    107 Monticello Ave, Annapolis, MD 21401
  • /50

    $695,000

    Open Sat 2PM - 4PM
    • 2 Beds
    • 1.5 Baths
    • 1,040 Sq Ft

    34 Pinkney St, Annapolis, MD 21401

    How many times have you strolled Annapolis' streets and thought, "I wish I lived here!"? 34 Pinkney is your opportunity to be in the center of the good life Annapolis has to offer! This renovated home is the perfect pied-à-terre. Some of the recent updates include New HVAC -2025, New Metal Roof-2020. Cozy living room flows to the dining with fun shiplap walls and built-in seating. The

    Alex Tower Sears TTR Sotheby's International Realty

    34 Pinkney St, Annapolis, MD 21401
  • /32

    $369,900

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 1,320 Sq Ft

    1008 Cedar Ridge Ct, Annapolis, MD 21403

    Welcome to this updated 3-bedroom, 2 full and 1 half bath townhome in the Cedar Ridge community, just minutes from downtown Annapolis! From the moment you arrive, this home invites you to slow down, settle in, and enjoy a lifestyle filled with comfort, convenience, and charm. Step inside and discover fresh updates that make everyday living feel special. New luxury vinyl plank flooring flows

    Diane Donnelly Keller Williams Flagship

    1008 Cedar Ridge Ct, Annapolis, MD 21403
  • /55

    $479,000

    Open Sun 11AM - 1:30PM $16K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,740 Sq Ft

    149 Quiet Waters Place, Annapolis, MD 21403

    PRICE REDUCED! OPEN HOUSE SUNDAY, June 28th 11-12:30PM. Tons of Upgrades Throughout! Beautifully updated by the current owners, this move-in ready home offers a fresh, modern feel with stylish finishes throughout and a rare opportunity to own in Annapolis at this price point, just minutes from Eastport, Downtown Annapolis, and Quiet Waters Park. Boasting over 2,000 square feet, the spacious floor

    Joanna Dalton Coldwell Banker Realty

    149 Quiet Waters Place, Annapolis, MD 21403
  • /50

    $1,150,000

    Open Sun 2PM - 4PM
    • 3 Beds
    • 3 Baths
    • 1,650 Sq Ft

    2127 Beach Village Ct Unit 202, Annapolis, MD 21403

    With just one look, you will fall in love! Vacation every day in your stunning two-level condo with exceptional views and amazing privacy! Wonderful open floor plan and walls of glass make you feel like you are on a boat and create outstanding views from every room. Exceptional features include smart technology throughout, a wood-burning fireplace, soaring ceilings, GE Cafe appliances (new in

    Alex Tower Sears TTR Sotheby's International Realty

    2127 Beach Village Ct Unit 202, Annapolis, MD 21403
  • /40

    $299,900

    Open Thu 5PM - 7PM $5K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,229 Sq Ft

    40 Greystone Ct Unit L, Annapolis, MD 21403

    Welcome to this fully renovated penthouse condo in the highly desirable Annapolis Overlook community. This spacious 2-bedroom, 2-bath residence features soaring 10-foot ceilings in the main living area, creating an airy, open feel filled with natural light, along with a cozy wood-burning fireplace perfect for cooler evenings. The thoughtfully designed open-concept layout flows seamlessly from the

    Kara Shaffer Engel & Völkers Annapolis

    40 Greystone Ct Unit L, Annapolis, MD 21403
  • /39

    $775,000

    Open Sat 11AM - 1PM
    • 3 Beds
    • 2.5 Baths
    • 4,497 Sq Ft

    211 N Pindell Ave, Annapolis, MD 21401

    Tucked just off Poplar Trail, 211 Pindell Avenue is a classic brick rancher that lives far larger than expected—4,497 square feet of light-filled, entertainer-ready space waiting to be enjoyed. Inside, walls of oversized windows pour sunshine across hardwood floors and custom trim. The living room rises to a vaulted ceiling anchored by a wood-burning fireplace, while the dining room charms with a

    June Steinweg Long & Foster Real Estate, Inc.

    211 N Pindell Ave, Annapolis, MD 21401
  • /47

    $774,900

    Open Sat 2PM - 4PM $25K PRICE DROP
    • 2 Beds
    • 1.5 Baths
    • 1,064 Sq Ft

    32 Cornhill St, Annapolis, MD 21401

    Great historic home built in 1850 in the heart of downtown historic Annapolis. Completely renovated and remodeled in 2023. New kitchen, new bathroom, recessed lights, new ceiling fans, lighting. Stainless steel appliances. Original hardwood floors. Front bedroom has cathedral ceiling. Exterior home has been completely painted in 2025. New decking off rear of home with a patio. Walking distance to

    Mark Feen Coldwell Banker Realty

    32 Cornhill St, Annapolis, MD 21401
  • /71

    $989,000

    Open Sat 1PM - 3PM
    • 8 Beds
    • 4 Baths
    • 3,108 Sq Ft

    1422 West St, Annapolis, MD 21401

    One of Homewood’s most distinctive homes, this 8-bedroom, 4-bath residence offers over 3,100 square feet and a truly unique story. Once known as the “Gables Tourist Home” Bed & Breakfast, the property (built in 1938) still carries subtle nods to its past—including the numbered bedroom doors—while the current owners have thoughtfully updated the interiors and major systems for comfortable modern

    Rachel Holmes Coldwell Banker Realty

    1422 West St, Annapolis, MD 21401

Home Prices in Annapolis, MD

Home Price Trends

Median Sale Price
$625,000
Median Single Family Sale Price
$839,950
Median Townhouse Sale Price
$462,000
Median 2 Bedroom Sale Price
$452,450
Median 1 Bedroom Sale Price
$453,700
Average Price Per Sq Ft
$363
Number of Homes for Sale
286
Last 12 months Home Sales
1,323
Months of Supply
2.60
Median List Price
$649,250
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
1%
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