28

Annapolis Neck, MD Homes for Sale with Pool

Section Image
  • 2014 Sams Way Unit 8A, Annapolis, MD 21403
    2014 Sams Way Unit 8A, Annapolis, MD 21403
    2014 Sams Way Unit 8A, Annapolis, MD 21403
    /44

    $599,900

    • 2 Beds
    • 2 Baths
    • 1,923 Sq Ft

    2014 Sams Way Unit 8A, Annapolis, MD 21403

    Nestled in the gated waterfront condo community of Chesapeake Harbor, this home offers an array of resort-style amenities, including two pools, a private beach, two fishing piers, kayak storage, jogging paths, a gym, a marina, tennis and pickleball courts, and an on-site waterfront restaurant. Inside, you'll find a spacious primary bedroom featuring a cozy reading nook, a large walk-in closet,

    Rick Gloekler RE/MAX Executive

    2014 Sams Way Unit 8A, Annapolis, MD 21403
  • 917 Arbutus Rd, Annapolis, MD 21403
    917 Arbutus Rd, Annapolis, MD 21403
    917 Arbutus Rd, Annapolis, MD 21403
    /121

    $5,250,000

    • 5 Beds
    • 3.5 Baths
    • 3,945 Sq Ft

    917 Arbutus Rd, Annapolis, MD 21403

    Welcome to 917 Arbutus Road—an extraordinary waterfront property nestled on 5 private acres with deep water on Crab Creek minutes from downtown Annapolis. This mid-century modern home offers over 3656 SF of light-filled living space, with soaring ceilings, expansive glass walls, and panoramic views of water and nature. The main level boasts four bedrooms and open-concept living areas designed

    Georgie Berkinshaw Coldwell Banker Realty

    917 Arbutus Rd, Annapolis, MD 21403
  • 48 Poplar Point Rd, Edgewater, MD 21037
    48 Poplar Point Rd, Edgewater, MD 21037
    48 Poplar Point Rd, Edgewater, MD 21037
    /41

    $3,750,000

    • 6 Beds
    • 5.5 Baths
    • 6,380 Sq Ft

    48 Poplar Point Rd, Edgewater, MD 21037

    Breathtaking water views and private deep water pier combine for effortless waterfront living. Nestled in the heart of Poplar Point on a serene lot with 350 feet of shoreline, this beautifully updated waterfront home offers panoramic views, exceptional privacy, and a lifestyle designed around comfort, nature, and time on the water. Nearly every room faces the water, with full-width views enjoyed

    Brad Kappel TTR Sotheby's International Realty

    48 Poplar Point Rd, Edgewater, MD 21037
  • 917 Childs Point Rd, Annapolis, MD 21401
    917 Childs Point Rd, Annapolis, MD 21401
    917 Childs Point Rd, Annapolis, MD 21401
    /40

    $3,700,000

    • 5 Beds
    • 6 Baths
    • 6,094 Sq Ft

    917 Childs Point Rd, Annapolis, MD 21401

    This stunning waterfront retreat offers privacy, breathtaking views of Crab Creek and the South River, and a waterside pool. The newly extended pier can accommodate a 50' sailboat. South-facing exposure and walls of windows let in tons of natural light and the sunlight sparkles off the serene waters at the shoreline. The beautiful renovation by Gate One Builders and new hardwood flooring created

    Brad Kappel TTR Sotheby's International Realty

    917 Childs Point Rd, Annapolis, MD 21401
  • 2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    2 River Dr, Annapolis, MD 21403
    /50

    $4,950,000

    • 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
  • 90 River Dr, Annapolis, MD 21403
    90 River Dr, Annapolis, MD 21403
    90 River Dr, Annapolis, MD 21403
    /44

    $2,550,000

    • 3 Beds
    • 4 Baths
    • 1,830 Sq Ft

    90 River Dr, Annapolis, MD 21403

    Coastal Charm with Iconic Views | 90 River Drive, Bay Ridge!Experience timeless waterfront living at 90 River Drive in the heart of Bay Ridge, Annapolis. This beautifully appointed 3–4 bedroom, 4-bath home features a detached guest house, ideal for guests, a home office, or a studio space. Enjoy breathtaking views of the Bay Bridge and direct access to one of the area’s most spectacular

    Salley Widmayer TTR Sotheby's International Realty

    90 River Dr, Annapolis, MD 21403
  • 22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    22 E Lake Dr, Annapolis, MD 21403
    /50

    $2,775,000

    • 3 Beds
    • 3.5 Baths
    • 3,320 Sq Ft

    22 E Lake Dr, Annapolis, MD 21403

    Previous Buyer's financing fell thru so back on the market with a huge 200k price reduction . Take advantage of this opportunity to vacation at home this summer and enjoy it now!Welcome to 22 East Lake, located in the sought-after waterfront community of Bay Ridge. This 3 bedroom 3.1 bath exceptional home blends refined sophistication with relaxed coastal living, offering the perfect space

    Betsy Dunigan TTR Sotheby's International Realty

    22 E Lake Dr, Annapolis, MD 21403
  • 3412 Hidden River View Rd, Annapolis, MD 21403
    3412 Hidden River View Rd, Annapolis, MD 21403
    3412 Hidden River View Rd, Annapolis, MD 21403
    /73

    $2,650,000

    • 5 Beds
    • 5.5 Baths
    • 5,671 Sq Ft

    3412 Hidden River View Rd, Annapolis, MD 21403

    CASUAL ELEGANCE BEST DESCRIBES THIS COASTAL STYLE HOME IN THE SOUGHT AFTER COMMUNITY OF FISHING CREEK FARM. THIS HOME IS AN ENTERTAINERS DREAM! THIS 5 BEDROOM, 5 BATH HOME HAS IT ALL! EXQUISITE DETAILS THROUGHOUT, RESORT STYLE HEATED POOL WITH WATERFALLS, OUTDOOR SHOWER, OUTDOOR FIREPLACE THAT LEADS TO A GREAT ENTERTAINING AREA UNDER THE DECK OFF THE POOL WITH WET BARS, HIGH TOPS, OUT DOOR TV'S,

    Pamela Tierney Coldwell Banker Realty

    3412 Hidden River View Rd, Annapolis, MD 21403
  • 1241 Cherry Tree Ln, Annapolis, MD 21403
    1241 Cherry Tree Ln, Annapolis, MD 21403
    1241 Cherry Tree Ln, Annapolis, MD 21403
    /47

    $2,675,000

    • 5 Beds
    • 5.5 Baths
    • 6,428 Sq Ft

    1241 Cherry Tree Ln, Annapolis, MD 21403

    Exquisite Savannah Style custom-built home in sought after, amenities-rich, Fishing Creek Farm community in Annapolis. This non-riparian waterfront home is nestled between 2 bodies of water providing endless water views from almost every room of the house. Wake up early to watch the wildlife and the sunrise over Cherry Tree Cove from the rear screened porch or enjoy peaceful water views and

    Brad Kappel TTR Sotheby's International Realty

    1241 Cherry Tree Ln, Annapolis, MD 21403
  • 3126 Port Way, Annapolis, MD 21403
    3126 Port Way, Annapolis, MD 21403
    3126 Port Way, Annapolis, MD 21403
    /59

    $1,675,000

    • 4 Beds
    • 5 Baths
    • 3,200 Sq Ft

    3126 Port Way, Annapolis, MD 21403

    Annapolis New Turnkey Masterpiece: Welcome to 3126 Port Way - an extraordinary residential real estate transformation in the highly sought-after Anchorage waterfront community in Annapolis. This fully reimagined masterpiece is the creation of a partnership between a contractor and an interior and space designer firm. Mac O’Brien, the owner of Great Eastern Contracting, and his wife Becca O’Brien

    Ani Gonzalez-Brunet Coldwell Banker Realty

    3126 Port Way, Annapolis, MD 21403
  • 2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
    /82

    $650,000

    • 3 Beds
    • 3 Baths
    • 1,700 Sq Ft

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403

    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 allows you to vacation at home year

    Lorna Kaim Compass

    2108 Chesapeake Harbour Dr E Unit 201, Annapolis, MD 21403
  • 45 E Lake Dr, Annapolis, MD 21403
    45 E Lake Dr, Annapolis, MD 21403
    45 E Lake Dr, Annapolis, MD 21403
    /67

    $1,498,000

    • 3 Beds
    • 3 Baths
    • 2,043 Sq Ft

    45 E Lake Dr, Annapolis, MD 21403

    Rare Bay Ridge Opportunity – 150’ Wide Lot - Across the street from Lake Ogleton.Don’t miss this incredible chance to build your dream home on one of Bay Ridge’s most coveted lots! Spanning 150 feet in width, this level property offers endless potential. Enjoy views of the Chesapeake Bay and Bay Bridge from a future two-story home—while living comfortably in the existing, move-in-ready

    Georgie Berkinshaw Coldwell Banker Realty

    45 E Lake Dr, Annapolis, MD 21403
  • 3140 Anchorage Dr, Annapolis, MD 21403
    3140 Anchorage Dr, Annapolis, MD 21403
    3140 Anchorage Dr, Annapolis, MD 21403
    /56

    $849,900

    • 4 Beds
    • 3 Baths
    • 2,555 Sq Ft

    3140 Anchorage Dr, Annapolis, MD 21403

    Priced to sell: Annapolis Stunning Contemporary - Located in the highly sought-after waterfront community of Anchorage, this stunning 3,000+ square foot contemporary 4-bedroom/3-bathroom home offers the perfect blend of architectural sophistication, modern upgrades, and serene coastal living. Main level living and open layout floor plan at its finest! This elegant home sits on a professionally

    Ani Gonzalez-Brunet Coldwell Banker Realty

    3140 Anchorage Dr, Annapolis, MD 21403
  • 13 Lawrence Ave, Annapolis, MD 21403
    13 Lawrence Ave, Annapolis, MD 21403
    13 Lawrence Ave, Annapolis, MD 21403
    /68

    $849,000

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft

    13 Lawrence Ave, Annapolis, MD 21403

    Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this Home Your Own! USE YOUR IMAGINATION! July 2025: Waterproofed entire interior basement with a below floor drain field w/ Durawall panels, new sump pump & Replace and raise window well and establish a drain (right side of home) SEE MLS DOCUMENTS SECTION FOR DETAILS & TRANSFERABLE GUARANTEE!. Great Location

    Gary Schneider Long & Foster Real Estate, Inc.

    13 Lawrence Ave, Annapolis, MD 21403
  • 3117 Port Way, Annapolis, MD 21403
    3117 Port Way, Annapolis, MD 21403
    3117 Port Way, Annapolis, MD 21403
    /60

    $797,000

    • 5 Beds
    • 3 Baths
    • 2,288 Sq Ft

    3117 Port Way, Annapolis, MD 21403

    Dramatic Price Reduction - Priced to Sell: Annapolis Hidden Gem in the Sought-After Anchorage Waterfront Community: Welcome to 3117 Port Way, a beautifully updated home nestled in the highly desirable Anchorage Waterfront community of Annapolis. This spacious 5-bedroom, 3-bathroom residence offers approximately 2,400 square feet of open-concept living space on a 0.34-acre lot, complete with a

    Ani Gonzalez-Brunet Coldwell Banker Realty

    3117 Port Way, Annapolis, MD 21403
  • 2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
    /95

    $1,700,000

    • 3 Beds
    • 3.5 Baths
    • 2,719 Sq Ft

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403

    Unprecedented waterfront opportunity in The Community of Chesapeake Harbour! Unduplicatable Gated Chesapeake Harbour offers lavish Chesapeake Bayfront Annapolitan style living. This community could never be built today and this property completes the trifecta with perfect location and luxurious refinements. 4 Levels of spectacular waterfront perfection masterfully done. Fully renovated and

    Christy Bishop Berkshire Hathaway HomeServices PenFed Realty

    2186 Chesapeake Harbour Dr E, Annapolis, MD 21403
  • 130 Great Lake Dr, Annapolis, MD 21403
    130 Great Lake Dr, Annapolis, MD 21403
    130 Great Lake Dr, Annapolis, MD 21403
    /71

    $650,000

    • 5 Beds
    • 2.5 Baths
    • 2,014 Sq Ft

    130 Great Lake Dr, Annapolis, MD 21403

    PRIVATE WATER COMMUNITY! 5 BEDROOM 2.5 FULL BATH BRICK HOME SITS ON .42 ACRE LOT IN SOUGHT AFTER HILLSMERE ESTATES! FRESHLY PAINTED THROUGHOUT! UPPER LEVEL HARDWOOD FLOORS HAVE BEEN REFINISHED! UPDATED KITCHEN W/ SS APPLIANCES, QUARTZ COUNTER TOPS, TILED BACKSPLASH, TABLE SPACE W/ BREAKFAST BAR & RECESSED LIGHTING. LIVING ROOM HAS BRICK FIREPLACE AND MANTEL, HARDWOOD FLOORS, BAY WINDOW W/

    Jennifer Drennan Taylor Properties

    130 Great Lake Dr, Annapolis, MD 21403
  • 840 Childs Point Rd, Annapolis, MD 21401
    840 Childs Point Rd, Annapolis, MD 21401
    840 Childs Point Rd, Annapolis, MD 21401
    /126

    $4,450,000

    • 6 Beds
    • 9 Baths
    • 12,374 Sq Ft

    840 Childs Point Rd, Annapolis, MD 21401

    One-of-a-kind Waterfront Luxury in Annapolis, Maryland! Secluded on 2.59 lush, park-like acres along the shores of one of the Chesapeake Bay’s most serene and protected tributaries, this exceptional estate offers an unparalleled blend of privacy, elegance, and premier waterfront living rarely found in Annapolis. From the moment you arrive down the tree-lined drive, a sense of calm and

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    840 Childs Point Rd, Annapolis, MD 21401
  • 54 River Dr, Annapolis, MD 21403
    54 River Dr, Annapolis, MD 21403
    54 River Dr, Annapolis, MD 21403
    /43

    $3,995,000

    • 4 Beds
    • 4.5 Baths
    • 3,250 Sq Ft

    54 River Dr, Annapolis, MD 21403

    Gorgeous coastal style home in the coveted Bay Ridge community with stunning and thoughtful renovations that highlight the expansive Chesapeake and Bay Bridge views! The extensive renovation by M Homes elevated the appeal and functionality of the home by adding 2 additional ensuite bedrooms and laundry room on the 2nd level and much more. No expense was spared to make this a home of distinction,

    Brad Kappel TTR Sotheby's International Realty

    54 River Dr, 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

    $2,595,000

    • 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 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 panoramic

    Brad Kappel TTR Sotheby's International Realty

    2175 Chesapeake Harbour Dr, Annapolis, MD 21403
  • 133 Lake View Dr, Annapolis, MD 21403
    133 Lake View Dr, Annapolis, MD 21403
    133 Lake View Dr, Annapolis, MD 21403
    /36

    $1,400,000

    • 5 Beds
    • 5 Baths
    • 4,308 Sq Ft

    133 Lake View Dr, Annapolis, MD 21403

    Absolutely transformed with a recently completed interior remodel this stunning contemporary home boasts panoramic water views across Lake Hillsmere and out to the South River; located in the coveted Hillsmere Shores community. With 5 bedrooms that all provide newly updated private baths, over 4,000 sqft of living space, 9'+ ceilings, freshly renovated first floor office, multiple decks including

    Brad Kappel TTR Sotheby's International Realty

    133 Lake View Dr, Annapolis, MD 21403
  • 7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
    /80

    $985,000

    • 3 Beds
    • 3 Baths
    • 2,041 Sq Ft

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403

    Welcome to this DESIGNER SHOWCASE including a custom painted entry that draws you in the moment you open the door. Owner worked with a reputable interior designer to select all finishes to include designer light fixtures, gorgeous real hardwood floors, custom designed bathrooms, and so many interesting trim details. Transitional timeless design with a coast twist. ONE OF A KIND and RARE

    Ann Chumney Coldwell Banker Realty

    7015 Chesapeake Harbour Dr Unit 23B, Annapolis, MD 21403
  • 48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    48 E Lake Dr, Annapolis, MD 21403
    /18

    $3,795,000 New Construction

    • 5 Beds
    • 4.5 Baths
    • 4,600 Sq Ft

    48 E Lake Dr, Annapolis, MD 21403

    Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. Don't miss your chance to own the last remaining waterfront lot and be in your new home by next boating season in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to work with the builder to design and build your dream home on a premium lot offering 57 feet of serene waterfront

    Colleen Smith EXP Realty, LLC

    48 E Lake Dr, Annapolis, MD 21403
  • 527 Lee Cir, Annapolis, MD 21403
    527 Lee Cir, Annapolis, MD 21403
    527 Lee Cir, Annapolis, MD 21403
    /8

    $1,300,000 Open Sat 11:30AM - 1:30PM

    • 4 Beds
    • 4 Baths
    • 3,065 Sq Ft

    527 Lee Cir, Annapolis, MD 21403

    Professional Photos Coming Next Wednesday, Open House 8/2 11:30-1:30PTucked at the end of a quiet cul-de-sac, this stylish home offers a private pier for your boat plus a floating dock for kayaks, paddleboards, and crabbing—the ideal setup for embracing the waterfront lifestyle. From cozy evenings around the firepit to vibrant gatherings on the two-tier Trex deck, this home is a true

    Jennifer McCormick Engel & Völkers Annapolis

    527 Lee Cir, Annapolis, MD 21403
  • 911 Breakwater Dr, Annapolis, MD 21403
    911 Breakwater Dr, Annapolis, MD 21403
    911 Breakwater Dr, Annapolis, MD 21403
    /43

    $425,000

    • 2 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    911 Breakwater Dr, Annapolis, MD 21403

    Welcome to this Updated Townhome boasting 2 Primary Bedrooms with Ensuites in the highly desired community of Mariners Landing where charm meets convenience. Open the door to this spacious home that was updated in 2021. Some of the numerous upgrades include new Kitchen Cabinets, Countertops, Microwave, all new Windows and Blinds, new HVAC, Carpeting, Vinyl Flooring, Retaining Wall and more,

    Joan Eisenhardt RE/MAX Executive

    911 Breakwater Dr, Annapolis, MD 21403
  • 7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
    /43

    $320,000

    • 1 Bed
    • 1.5 Baths
    • 1,000 Sq Ft

    7101 Bay Front Dr Unit 204, Annapolis, MD 21403

    Gorgeous 1 bedroom, 1.5 bath condo on the second floor. Freshly painted and new carpet have been installed. This is one MOVE IN READY. Enjoy all the ammenities that Baywoods has to offer and enjoy being directly on the Chesapeake Bay. Luxury and convenience at it's finest.

    Crystal Smith RE/MAX Executive

    7101 Bay Front Dr Unit 204, Annapolis, MD 21403
  • 7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
    /63

    $275,000

    • 1 Bed
    • 1 Bath
    • 1,000 Sq Ft

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403

    Are you ready to relax and let someone else do the cooking and cleaning? Now is your opportunity! One monthly payment takes care of food, cleaning, ALL utilities, taxes, insurance, maintenance, everything is included in the monthly fee!! There's even medical staff on duty 24 hours a day/seven days a week. And it's all located within a luxurious Annapolis retirement community for those

    Diane Gavin Long & Foster Real Estate, Inc.

    7101 Bay Front Dr Unit 400, Annapolis, MD 21403
  • 712 Pearson Point Place, Annapolis, MD 21401
    712 Pearson Point Place, Annapolis, MD 21401
    712 Pearson Point Place, Annapolis, MD 21401
    /44

    $950,000

    • 5 Beds
    • 4.5 Baths
    • 5,184 Sq Ft

    712 Pearson Point Place, Annapolis, MD 21401

    Nestled in sought-after Kingsport, this impeccably maintained residence offers a rare combination of comfort, style, and convenience. Kingsport residents enjoy exclusive access to a private pool, community dock, and beautifully landscaped walking trails—perfect for morning jogs, evening strolls, or weekend paddle-boarding adventures.This expansive home features five generously sized

    Amber Krause TTR Sotheby's International Realty

    712 Pearson Point Place, Annapolis, MD 21401
Maryland Annapolis Neck

Homes for Sale with Pool in Annapolis Neck, MD

How to Buy a Home How to Finance a Home How to Sell a Home

In Annapolis Neck, there are currently 28 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 Neck, MD and discover your ideal residence.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group