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Annapolis, MD Homes for Sale with Pool

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  • 933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    933 Breakwater Dr, Annapolis, MD 21403
    /20

    $390,000

    • 2 Beds
    • 2.5 Baths
    • 1,319 Sq Ft

    933 Breakwater Dr, Annapolis, MD 21403

    This spacious and well-maintained townhouse offers comfortable living in a highly desirable Annapolis location. The main level features a welcoming living room centered around a classic wood-burning fireplace, creating a warm focal point and cozy atmosphere, while the French doors provide access to the backyard, allowing natural light to fill the space while offering an easy transition to outdoor

    Agent Photo

    Scott Smolen

    RE/MAX Leading Edge

    (443) 323-0308

    933 Breakwater Dr, Annapolis, MD 21403
  • 2006 Peggy Stewart Way Unit 204, Annapolis, MD 21401
    2006 Peggy Stewart Way Unit 204, Annapolis, MD 21401
    2006 Peggy Stewart Way Unit 204, Annapolis, MD 21401
    /33

    $345,000

    • 2 Beds
    • 2 Baths
    • 1,046 Sq Ft

    2006 Peggy Stewart Way Unit 204, Annapolis, MD 21401

    Welcome to this beautiful 2-bedroom, 2-bath condo in the highly sought-after Tidewater Colony community of Annapolis. Inside, you’ll find 9-foot ceilings, luxury vinyl plank floors, custom blinds, and a modern kitchen with granite countertops, gas cooking, and a built-in microwave. The spacious primary suite features a double vanity and a luxurious bath with separate shower and soaking tub.

    Agent Photo

    Julie Procopio

    Berkshire Hathaway HomeServices Homesale Realty

    (443) 501-2774

    2006 Peggy Stewart Way Unit 204, Annapolis, MD 21401
  • 50 Hearthstone Ct, Annapolis, MD 21403
    50 Hearthstone Ct, Annapolis, MD 21403
    50 Hearthstone Ct, Annapolis, MD 21403
    /37

    $360,000

    • 3 Beds
    • 2.5 Baths
    • 1,620 Sq Ft

    50 Hearthstone Ct, Annapolis, MD 21403

    NEW KITCHEN just installed! The eat-in kitchen has been updated with NEW tall, white kitchen cabinetry w/brushed bronze handles, NEW upgraded quartz countertops,NEW lighting, freshly painted, and boasts all stainless steel appliances including a gas range, french door refrigerator, dishwasher, and microwave—all installed within the past year. Enjoy Annapolis living with a community pool and

    Agent Photo

    Sandy Wing

    RE/MAX Leading Edge

    (410) 989-4664

    50 Hearthstone Ct, Annapolis, MD 21403
  • 860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    860 Woodmont Rd, Annapolis, MD 21401
    /55

    $629,000 Open Sat 1:30PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,623 Sq Ft

    860 Woodmont Rd, Annapolis, MD 21401

    Welcome to this beautifully updated 3-bedroom, 2-bath single-family home in the highly sought-after, amenity-rich Heritage Harbour community in Annapolis. Thoughtfully designed for comfortable main-level living, this home features a spacious primary suite with a gorgeous updated bath and walk-in closet, along with a second bedroom, 2nd updated full bath, and convenient main-level laundry.The

    Agent Photo

    Kara Leddy

    Coldwell Banker Realty

    (410) 883-7342

    860 Woodmont Rd, Annapolis, MD 21401
  • 2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
    /62

    $750,000

    • 3 Beds
    • 3 Baths
    • 1,645 Sq Ft

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403

    Welcome to an exceptional living experience at Chesapeake Harbour, where this well maintained 3 bedroom, 3 full bath condo offers not just a home but a lifestyle. Perfectly situated in a premium location, this residence boasts breathtaking views of the Bay Bridge and the sparkling waters of the Bay, providing a serene backdrop to your daily life. Step into a well-designed space that seamlessly

    Agent Photo

    Lorna Kaim

    Compass

    (410) 305-9422

    2018 Quay Village Ct Unit 201, Annapolis, MD 21403
  • 5 Park Place Unit 107, Annapolis, MD 21401
    5 Park Place Unit 107, Annapolis, MD 21401
    5 Park Place Unit 107, Annapolis, MD 21401
    /29

    $625,000

    • 2 Beds
    • 2 Baths
    • 1,272 Sq Ft

    5 Park Place Unit 107, Annapolis, MD 21401

    Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming hardwood floors, spacious and bright layout, and a stylish kitchen, this residence combines comfort and convenience. Park Place offers exceptional amenities including 24/7 concierge service, a pool, fitness center, meeting and party rooms, library, and a rear outdoor patio with a kitchen and grilling

    Wemmy Collins Redfin Corp

    5 Park Place Unit 107, Annapolis, MD 21401
  • 1943 Marconi Cir, Annapolis, MD 21401
    1943 Marconi Cir, Annapolis, MD 21401
    1943 Marconi Cir, Annapolis, MD 21401
    /27

    $430,000

    • 2 Beds
    • 2 Baths
    • 1,032 Sq Ft

    1943 Marconi Cir, Annapolis, MD 21401

    Back on the market! Buyer's loss is your gain.One-level living in the highly desired 55+ community of Heritage Harbour! This well-maintained 2-bedroom, 2-bath villa townhome offers updates including: NEW ANDERSON WINDOWS, roof approximately 3 years old, luxury vinyl plank flooring, carpeted bedrooms, and solar tubes providing added natural light.The renovated kitchen (approx. 5 years)

    Deborah Wade RE/MAX Executive

    1943 Marconi Cir, Annapolis, MD 21401
  • 1165 Green Holly Ct, Annapolis, MD 21409
    1165 Green Holly Ct, Annapolis, MD 21409
    1165 Green Holly Ct, Annapolis, MD 21409
    /47

    $650,000

    • 3 Beds
    • 2 Baths
    • 2,218 Sq Ft

    1165 Green Holly Ct, Annapolis, MD 21409

    Cape St. Claire Home sold with Extra Lot included! This lovely Cape St. Claire property boasts an extra lot, offering more space for your family to enjoy. Build a detached garage with extra living space or possible ADU. Upon entering the home, you’ll immediately feel at ease. The spacious living room, which could also serve as a formal dining area, features a cozy fireplace. The kitchen, with its

    Darlene Winegardner RE/MAX Executive

    1165 Green Holly Ct, Annapolis, MD 21409
  • 926 Perry Landing Ct, Annapolis, MD 21401
    926 Perry Landing Ct, Annapolis, MD 21401
    926 Perry Landing Ct, Annapolis, MD 21401
    /40

    $445,000

    • 2 Beds
    • 2.5 Baths
    • 2,106 Sq Ft

    926 Perry Landing Ct, Annapolis, MD 21401

    Welcome to 926 Perry Landing Court, located in the highly sought-after Heritage Harbour, Annapolis’ premier 55+ active adult waterfront community. Tucked away on a quiet court, this home offers a functional layout, generous room sizes, and great natural light throughout. The property will need some cosmetic updates and improvements to truly make it your own and has been priced accordingly to

    Rick Gloekler RE/MAX Executive

    926 Perry Landing Ct, Annapolis, MD 21401
  • 1344 Tydings Rd, Annapolis, MD 21409
    1344 Tydings Rd, Annapolis, MD 21409
    1344 Tydings Rd, Annapolis, MD 21409
    /43

    $1,599,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 4.5 Baths
    • 5,536 Sq Ft

    1344 Tydings Rd, Annapolis, MD 21409

    Old-world elegance is masterfully expressed in this exceptional Villa, a true work of art set on a lush and private 1.26-acre homesite just one block from the Chesapeake Bay. A rare offering that seamlessly blends timeless European craftsmanship with modern luxury, the residence is defined by hand-chiseled stone, classic stucco, and a striking terracotta tile roof, creating a presence that is

    Brad Kappel TTR Sotheby's International Realty

    1344 Tydings Rd, Annapolis, MD 21409
  • 1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
    /24

    $695,000

    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft

    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401

    Welcome to the highly sought-after “Davenport” corner unit in the prestigious GrandView community — perfectly positioned in one of the most desirable locations in the Annapolis Town Center. This exceptional residence is filled with natural light thanks to a stunning wall of windows, offering breathtaking sunset views each evening. Step outside to your private covered corner balcony and enjoy the

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 403, Annapolis, MD 21401
  • 1292 Spa Rd, Annapolis, MD 21403
    1292 Spa Rd, Annapolis, MD 21403
    1292 Spa Rd, Annapolis, MD 21403
    /62

    $1,595,000

    • 5 Beds
    • 4.5 Baths
    • 4,672 Sq Ft

    1292 Spa Rd, Annapolis, MD 21403

    CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL HOME INSPIRED BY ARCHITECT A. HAYS TOWN. THIS HOME IS AN ENTERTAINER'S DREAM. THIS 5-BEDROM, 4.FULL & 2 HALF-BATH(2ND HALF BATH IN THE POOL HOUSE) HAS IT ALL! EXQUISITE DETAILS THROUGHOUT, RESORT STYLE HEATED SALT WATER POOL W/SUN DECK & WATER FEATURES. THERE IS AN AMAZING POOL HOUSE W/BATH, OUTDOOR TV, GORGEOUS WOOD BEAM PAVILION THAT LEADS TO AN

    Pamela Tierney Coldwell Banker Realty

    1292 Spa Rd, Annapolis, MD 21403
  • 22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    /79

    $2,550,000 Open House 4/11

    • 3 Beds
    • 2.5 Baths
    • 2,338 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Welcome to 22 E Lake Drive! This exceptional waterfront residence offers striking architectural elements with expansive, light-filled interiors and seamless indoor-outdoor living along the Chesapeake Bay.The main level open floor plan is designed for effortless flow and everyday living. The living room anchors the space, featuring a floor-to-ceiling stone fireplace and a wall of bi-fold glass

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    22 E Lake Dr, Annapolis, MD 21403
  • 1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
    /26

    $549,000

    • 2 Beds
    • 2 Baths
    • 1,485 Sq Ft

    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401

    This exceptional 5th-floor condo offers a one-of-a-kind, unique floor plan with breathtaking panoramic views and an abundance of natural light from its sunny southern exposure. Featuring two generously sized bedrooms with expansive closets, this upscale residence combines comfort and style. Inside, you’ll find beautiful hardwood floors, soaring 10-foot ceilings, and elegant granite countertops

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 513, Annapolis, MD 21401
  • 40 Ironstone Ct, Annapolis, MD 21403
    40 Ironstone Ct, Annapolis, MD 21403
    40 Ironstone Ct, Annapolis, MD 21403
    /36

    $359,999 Open Sat 12PM - 2PM

    • 3 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    40 Ironstone Ct, Annapolis, MD 21403

    Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll

    Lisa Gilmore Keller Williams Flagship

    40 Ironstone Ct, Annapolis, MD 21403
  • 707 Pilot House Dr, Annapolis, MD 21401
    707 Pilot House Dr, Annapolis, MD 21401
    707 Pilot House Dr, Annapolis, MD 21401
    /45

    $945,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 4.5 Baths
    • 4,797 Sq Ft

    707 Pilot House Dr, Annapolis, MD 21401

    Welcome to this exceptional Kingsport 4 BR, 5 BA home with over 4600+ SF of beautifully designed finished living space tailored for both everyday comfort and unforgettable entertaining. Thoughtfully enhanced by its original owners, the home features over $150K in state of the art, commercial grade electronics, seamlessly integrating lighting, whole-home audio, and premium theatre systems

    Moe Farley Coldwell Banker Realty

    707 Pilot House Dr, Annapolis, MD 21401
  • 30 Hearthstone Ct Unit J, Annapolis, MD 21403
    30 Hearthstone Ct Unit J, Annapolis, MD 21403
    30 Hearthstone Ct Unit J, Annapolis, MD 21403
    /38

    $295,000 Open Sat 12PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,376 Sq Ft

    30 Hearthstone Ct Unit J, Annapolis, MD 21403

    Welcome to this beautifully maintained 2-bedroom, 2-bath condominium in the desirable Annapolis Overlook community, offering 1,376 square feet of comfortable living space. This inviting home features warm wood flooring and a cozy wood-burning fireplace, creating the perfect setting for both everyday living and relaxing evenings. Step outside onto your private balcony and enjoy peaceful wooded

    Billy Barr Keller Williams Realty Delmarva

    30 Hearthstone Ct Unit J, Annapolis, MD 21403
  • 1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    1519 Winchester Rd, Annapolis, MD 21409
    /34

    $849,000 Open Sat 11AM - 3PM

    • 5 Beds
    • 3 Baths
    • 2,375 Sq Ft

    1519 Winchester Rd, Annapolis, MD 21409

    Set on a beautifully landscaped 0.34-acre corner lot in sought-after Winchester-on-the-Severn, this thoughtfully renovated residence offers a seamless blend of style, comfort, and everyday livability. A fully fenced backyard creates a private outdoor retreat, complete with a deck, patio, garden, playground, and storage shed, perfectly designed for both entertaining and relaxed daily living.

    Brad Kappel TTR Sotheby's International Realty

    1519 Winchester Rd, Annapolis, MD 21409
  • 5 Silverwood Cir Unit 1, Annapolis, MD 21403
    5 Silverwood Cir Unit 1, Annapolis, MD 21403
    5 Silverwood Cir Unit 1, Annapolis, MD 21403
    /25

    $293,500 Open House 4/11

    • 2 Beds
    • 2 Baths

    5 Silverwood Cir Unit 1, Annapolis, MD 21403

    Popular Fairwinds Condo is a great place to live!! Two Bedroom Two Bath with den condominium ! Newer stainless steel appliances ! Freshly painted 2026 ! Luxury Vinyl thru living areas and carpet in bedrooms! Lots of closets and storage! Extra storage area included in basement ! Master bedroom has full bath ! Updated kitchen ! New light fixtures including eyeball lights! New glass door in shower

    Bev Langley Coldwell Banker Realty

    5 Silverwood Cir Unit 1, Annapolis, MD 21403
  • 930 Astern Way Unit 510, Annapolis, MD 21401
    930 Astern Way Unit 510, Annapolis, MD 21401
    930 Astern Way Unit 510, Annapolis, MD 21401
    /22

    $195,000

    • 1 Bed
    • 1.5 Baths
    • 1,152 Sq Ft

    930 Astern Way Unit 510, Annapolis, MD 21401

    Welcome to 930 Astern Way — a spacious 1-bedroom, 11⁄2-bath condominium located in the sought-after 55+ community of Heritage Harbour. This bright and inviting unit offers modern comfort and low-maintenance living. The open layout creates an airy feel, with abundant natural light flowing throughout the home. The generously sized bedroom includes a private full bath, while the additional half bath

    Jack Papaleonti Academy Realty Inc.

    930 Astern Way Unit 510, Annapolis, MD 21401
  • 906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    906 Perry Landing Ct, Annapolis, MD 21401
    /59

    $609,900

    • 2 Beds
    • 2.5 Baths
    • 2,569 Sq Ft

    906 Perry Landing Ct, Annapolis, MD 21401

    Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and an unmatched lifestyle.This spacious end-unit villa boasts over 2,500 square feet of living space and is filled with natural light thanks to its desirable end-unit location. Freshly painted throughout with brand new flooring and carpet, this home is truly move-in ready and features soaring ceilings

    Jack Papaleonti Academy Realty Inc.

    906 Perry Landing Ct, Annapolis, MD 21401
  • 5 Park Place Unit 425, Annapolis, MD 21401
    5 Park Place Unit 425, Annapolis, MD 21401
    5 Park Place Unit 425, Annapolis, MD 21401
    /10

    $477,900

    • 1 Bed
    • 1 Bath
    • 838 Sq Ft

    5 Park Place Unit 425, Annapolis, MD 21401

    Beautiful 1Br/1Bath facing east w pool/courtyard view. Hardwood floor, GE Stainless Steel appliances, Granite counter. Full Size W/D inside unit. 24 Hour concierge/security in lobby. 25 amenities including most utilities included in condo fee. Outdoor Pool, Fitness center, Party Room, Library, Outdoor Dining area with BBQ grills, Hot Tub, Dog Park and much more. Blocks to downtown City Dock

    George Gorayeb Anne Arundel Properties, Inc.

    5 Park Place Unit 425, Annapolis, MD 21401
  • 2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
    /58

    $595,000

    • 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,

    Lorna Kaim Compass

    2110 Chesapeake Harbour Dr Unit 101, Annapolis, MD 21403
  • 605 Admiral Dr, Annapolis, MD 21401
    605 Admiral Dr, Annapolis, MD 21401
    605 Admiral Dr, Annapolis, MD 21401
    /41

    $395,000

    • 2 Beds
    • 2 Baths
    • 1,514 Sq Ft

    605 Admiral Dr, Annapolis, MD 21401

    HURRY! This location is EVERTHING! Ready for a low-maintenance lifestyle? Experience effortless living in this beautifully updated & meticulously maintained Penthouse/Loft unit in the heart of ALL that is Annapolis. Step inside & prepare to be dazzled by it's soaring ceilings & bright open vibe adorned with all the fun "toppings" necessary for comfort in living. NEW (2021-present) FANTASTIC

    Amy Faust Long & Foster Real Estate, Inc.

    605 Admiral Dr, Annapolis, MD 21401
  • 5 Park Place Unit 725, Annapolis, MD 21401
    5 Park Place Unit 725, Annapolis, MD 21401
    5 Park Place Unit 725, Annapolis, MD 21401
    /34

    $499,000

    • 1 Bed
    • 1 Bath
    • 792 Sq Ft

    5 Park Place Unit 725, Annapolis, MD 21401

    Downtown living at its finest! A Naval Academy family dream location! An open layout combines living and dining areas with a modern kitchen, creating a comfortable, functional main living space that’s ideal for everyday living and easy entertaining. Beautiful hardwood floors, stainless steel appliances, in-unit laundry, and plenty of storage enhance the interior, while large windows bring in

    Megan Koppe Compass

    5 Park Place Unit 725, Annapolis, MD 21401
  • 2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    2646 Quiet Water Cove, Annapolis, MD 21401
    /60

    $509,900

    • 3 Beds
    • 2 Baths
    • 2,354 Sq Ft

    2646 Quiet Water Cove, Annapolis, MD 21401

    Popular, one level floor plan in the 55+ community of Heritage Harbour offering just the right amount of space to enjoy the next phase of your life. You will feel right at home when you turn into this lovely, cul de sac with mature trees and attractive, brick or stone front homes. Pull into your one car garage with automatic door opener & immediate access to the kitchen for easy unloading of

    Martin Lanzino Douglas Realty, LLC

    2646 Quiet Water Cove, Annapolis, MD 21401
  • 930 Astern Way Unit 304, Annapolis, MD 21401
    930 Astern Way Unit 304, Annapolis, MD 21401
    930 Astern Way Unit 304, Annapolis, MD 21401
    /42

    $275,000

    • 1 Bed
    • 1.5 Baths
    • 1,152 Sq Ft

    930 Astern Way Unit 304, Annapolis, MD 21401

    Welcome to 930 Astern Way — a spacious and beautifully updated 1-bedroom, 11⁄2-bath condominium located in the sought-after 55+ community of Heritage Harbour. This bright and inviting unit has been thoughtfully refreshed with luxury vinyl plank flooring, an updated kitchen, and renovated bathrooms, offering modern comfort and low-maintenance living. The open layout creates an airy feel, with

    Jack Papaleonti Academy Realty Inc.

    930 Astern Way Unit 304, Annapolis, MD 21401
  • 21 Silverwood Cir Unit 11, Annapolis, MD 21403
    21 Silverwood Cir Unit 11, Annapolis, MD 21403
    21 Silverwood Cir Unit 11, Annapolis, MD 21403
    /33

    $325,000

    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    21 Silverwood Cir Unit 11, Annapolis, MD 21403

    Perched on the top floor of the sought-after Fairwinds of Annapolis community, this beautifully updated condo offers a quiet retreat with no neighbors above and serene courtyard views. Surrounded by mature trees and thoughtfully landscaped common areas, residents enjoy a well-maintained setting complete with a pool, tennis courts, tot lots, snow removal, picnic areas for grilling, bike and kayak

    Mr. Mason Lyon Northrop Realty

    21 Silverwood Cir Unit 11, Annapolis, MD 21403
  • 706 Drake Way, Annapolis, MD 21401
    706 Drake Way, Annapolis, MD 21401
    706 Drake Way, Annapolis, MD 21401
    /44

    $905,000 Open Sat 11:30AM - 1:30PM

    • 4 Beds
    • 4.5 Baths
    • 4,571 Sq Ft

    706 Drake Way, Annapolis, MD 21401

    Experience the best of Annapolis living in this beautifully cared-for Kingsport home, offering a perfect blend of comfort, style, and thoughtful upgrades. Built by Basheer & Edgemoore, this 4 bedroom, 4.5 bath residence welcomes you with a bright two-story foyer and an inviting layout designed for both everyday living and effortless entertaining.Hardwood floors, plantation shutters. recessed

    Anne Harrington Coldwell Banker Realty

    706 Drake Way, Annapolis, MD 21401
  • 1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    1106 Mainsail Dr, Annapolis, MD 21403
    /57

    $895,000

    • 5 Beds
    • 2.5 Baths
    • 2,059 Sq Ft

    1106 Mainsail Dr, Annapolis, MD 21403

    At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated

    Jill Windsor Long & Foster Real Estate, Inc.

    1106 Mainsail Dr, Annapolis, MD 21403
  • 1036 Mountain Top Dr, Annapolis, MD 21409
    1036 Mountain Top Dr, Annapolis, MD 21409
    1036 Mountain Top Dr, Annapolis, MD 21409
    /78

    $725,000

    • 4 Beds
    • 3 Baths
    • 2,692 Sq Ft

    1036 Mountain Top Dr, Annapolis, MD 21409

    Welcome Home - this beautiful property is located in the sought after Cape St. Claire community. First floor living meets comfort and charm. This beautifully designed home features a spacious primary suite with a stunning ensuite bath and private access to the backyard, creating a seamless indoor-outdoor retreat. Situated on a rare double lot, the outdoor space is truly exceptional. Enjoy your

    Jessica Ricciardi Welder Keller Williams Flagship

    1036 Mountain Top Dr, Annapolis, MD 21409
  • 2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    /50

    $3,850,000

    • 6 Beds
    • 4.5 Baths
    • 3,818 Sq Ft

    2 River Dr, Annapolis, MD 21403

    2 River with its stunning water views of the Severn River and of the Chesapeake Bay epitomizes the Annapolis Lifestyle! Located in this beloved multi-generational community of Bay Ridge, this exquisitely renovated classic home seamlessly blends the timeless updates and fabulous original detail such as leaded glass windows and brass chandeliers. The main level has the most incredible, breezy

    Alex Tower Sears TTR Sotheby's International Realty

    2 River Dr, Annapolis, MD 21403
  • 300 Hilltop Ln Unit H, Annapolis, MD 21403
    300 Hilltop Ln Unit H, Annapolis, MD 21403
    300 Hilltop Ln Unit H, Annapolis, MD 21403
    /27

    $275,000

    • 2 Beds
    • 2 Baths
    • 1,082 Sq Ft

    300 Hilltop Ln Unit H, Annapolis, MD 21403

    Welcome to easy Annapolis living at 300 Hilltop Lane! This well-maintained 2-bedroom, 2-bath second-level condo offers over 1,000 square feet of comfortable living space with a bright, open layout perfect for everyday living and entertaining. The spacious living and dining area features beautiful hardwood flooring and abundant natural light, creating a warm and inviting atmosphere. The kitchen is

    Christopher Sidoriak Keller Williams Flagship

    300 Hilltop Ln Unit H, Annapolis, MD 21403
  • 316 Burnside St Unit 203, Annapolis, MD 21403
    316 Burnside St Unit 203, Annapolis, MD 21403
    316 Burnside St Unit 203, Annapolis, MD 21403
    /34

    $482,000

    • 1 Bed
    • 1 Bath
    • 525 Sq Ft

    316 Burnside St Unit 203, Annapolis, MD 21403

    Welcome to the sought-after Newport Condominiums in Eastport, where coastal charm meets walkable Annapolis living. This beautifully updated 1 bedroom, 1 bath second-floor condo offers natural light, custom updates, and a coveted location just steps from Spa Creek and downtown Annapolis.The bright and inviting interior features built-in cabinetry, replaced windows, and stylish new light

    Jeannie Miller Long & Foster Real Estate, Inc.

    316 Burnside St Unit 203, Annapolis, MD 21403
  • 2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
    /39

    $725,000

    • 3 Beds
    • 3 Baths
    • 1,748 Sq Ft

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403

    WATCH THE SUNSETS & ENJOY THE BREATHTAKING MARINA VIEWS FROM THIS BEAUTIFUL 3 BEDROOM, 3 FULL BATH CONDO IN CHESAPEAKE HARBOUR! ENJOY LIFE BY THE WATER IN THIS TURN KEY RENOVATED CONDO. BOTH THE WATERSIDE PRIMARY AND LIVING ROOM HAVE SLIDERS TO THE WATERSIDE BALCONY. FEATURES INCLUDE GOURMET KITCHEN, DESIGNER LIGHTING, NEW ENTRY WAY, COUNTERTOPS, HVAC, SLIDERS, STAINLESS STEEL APPLIANCES,

    Pamela Tierney Coldwell Banker Realty

    2114 Chesapeake Harbour Dr E Unit 202, Annapolis, MD 21403
  • 78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409
    78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409
    /37

    $710,000

    • 2 Beds
    • 2 Baths
    • 1,723 Sq Ft

    78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409

    Experience refined living in this stunning second-floor corner residence, a brand-new 2024-built condominium offering 1,723 square feet of beautifully designed living space filled with natural light. Formerly the community’s model home, this exceptional residence showcases designer finishes, thoughtful upgrades, and meticulous attention to detail throughout. The well-designed floor plan features

    Shannon Thayer Douglas Realty, LLC

    78 Old Mill Bottom Rd N Unit 211, Annapolis, MD 21409
  • 1113 Primrose Ct Unit 204, Annapolis, MD 21403
    1113 Primrose Ct Unit 204, Annapolis, MD 21403
    1113 Primrose Ct Unit 204, Annapolis, MD 21403
    /37

    $279,000

    • 2 Beds
    • 1 Bath
    • 922 Sq Ft

    1113 Primrose Ct Unit 204, Annapolis, MD 21403

    Welcome to 1113 Primrose Court #204 in the ultra convenient community of The Landing at Spa Creek! Step into a recently refreshed building with secure keypad entry and head up to this spacious second floor, 2 bedroom, 1 bath condo. Inside, you’ll be delighted by the light filled living room and open floor plan, perfect for everyday living and entertaining. The updated kitchen features a large

    Chad Robertson Compass

    1113 Primrose Ct Unit 204, Annapolis, MD 21403
  • 2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
    /44

    $2,295,000

    • 4 Beds
    • 4.5 Baths
    • 2,513 Sq Ft

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403

    Indulge in resort-like living at Chesapeake Harbour, a gated community filled with amenities and stunning water views of the Chesapeake Bay. This modern and spacious 4 bedroom, 4.5 bathroom townhome with elevator spans 4 levels and just over 2,500 square feet, featuring high-end design and curated finishes. The open floor plan makes entertaining seamless and focuses the attention on the stunning

    Brad Kappel TTR Sotheby's International Realty

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
  • 1915 Towne Centre Blvd Unit 503, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 503, Annapolis, MD 21401
    1915 Towne Centre Blvd Unit 503, Annapolis, MD 21401
    /53

    $725,000

    • 2 Beds
    • 2 Baths
    • 1,602 Sq Ft

    1915 Towne Centre Blvd Unit 503, Annapolis, MD 21401

    Welcome to the highly sought-after “Davenport” corner unit in the prestigious GrandView community — perfectly positioned in one of the most desirable locations in the Annapolis Town Center. This exceptional residence is filled with natural light thanks to a stunning wall of windows, offering breathtaking sunset views each evening. Step outside to your private covered corner balcony and enjoy the

    David Yee Coldwell Banker Realty

    1915 Towne Centre Blvd Unit 503, Annapolis, MD 21401
  • 10 Amberstone Ct, Annapolis, MD 21403
    10 Amberstone Ct, Annapolis, MD 21403
    10 Amberstone Ct, Annapolis, MD 21403
    /30

    $315,000

    • 2 Beds
    • 2 Baths
    • 1,138 Sq Ft

    10 Amberstone Ct, Annapolis, MD 21403

    This lovely first floor condo, conveniently located in Annapolis, has two bedrooms, a den and two full bathrooms. Open concept living room, dining area and kitchen with a nice patio overlooking the woods behind it. Ceramic floors in the front hall and kitchen. Freshly painted throughout. New carpet in the den and two bedrooms. Luxury vinyl plank flooring in the living room and dining room area.

    Wilma Richards Long & Foster Real Estate, Inc.

    10 Amberstone Ct, Annapolis, MD 21403

Showing Results 1 - 40, Page 1 of 3

Maryland Anne Arundel County Annapolis

Homes for Sale with Pool in Annapolis, MD

Home Trends in Annapolis, MD

On average, homes in Annapolis, MD sell after 37 days on the market compared to the national average of 55 days. The median sale price for homes in Annapolis, MD over the last 12 months is $625,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$625,000
Median Single Family Sale Price
$822,500
Median Townhouse Sale Price
$450,000
Median 2 Bedroom Sale Price
$420,000
Median 1 Bedroom Sale Price
$447,500
Average Price Per Sq Ft
$354
Number of Homes for Sale
235
Last 12 months Home Sales
1,313
Months of Supply
2.10
Median List Price
$635,000
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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In Annapolis, there are currently 93 homes for sale with a pool, providing a refreshing retreat and a space for leisure. Whether it's a house for sale with a pool for those warm summer days, or a property featuring an indoor or screened-in pool for year-round enjoyment, these homes offer recreation right at home. Additionally, buyers can consider properties with access to community pools, offering a convenient space for relaxation and socializing. Whether you prefer a private pool or the convenience of a community pool, browse homes for sale with a pool in Annapolis, MD and discover your ideal residence.

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