Annapolis Homes with Pool

Annapolis Homes with Pool

Welcome to Annapolis, Maryland – a charming city steeped in history and brimming with coastal allure. Nestled along the scenic shores of the Chesapeake Bay, Annapolis is not just the state capital; it’s a vibrant hub of culture, culinary delights, and waterfront adventures. With its rich maritime heritage, the city boasts beautifully preserved 18th-century architecture, making it a picturesque backdrop for everyday living.

Annapolis offers a unique blend of urban sophistication and small-town charm. Stroll through the cobblestone streets of the historic district, where boutique shops and gourmet restaurants await. For those who appreciate the great outdoors, the city is a paradise for boating enthusiasts, with endless opportunities for sailing, kayaking, and fishing. The nearby parks and waterfront areas provide a perfect setting for picnics, leisurely walks, and stunning sunsets.

For homebuyers seeking a slice of this idyllic lifestyle, Annapolis features a variety of properties, including exquisite homes with pools. Imagine relaxing in your own private oasis, soaking up the sun or hosting summer barbecues with friends and family. These homes not only offer the luxury of a pool but also the convenience of being close to the city’s vibrant amenities and breathtaking natural beauty.

Whether you're drawn to the historic charm, the bustling arts scene, or the serene waterfront, Annapolis invites you to make it your home. Discover the perfect property that offers both comfort and a lifestyle enriched by the beauty of Maryland’s capital. Dive into your dream home with a pool today and experience the enchanting lifestyle that Annapolis has to offer!

Newest Annapolis Homes with Pool

5 Beds ⋅ 4 Baths

Turn key and thoughtfully updated, this 5-bedroom, 4.5-bath single-family home offers a rare combination of spacious living, modern upgrades, and resort-style outdoor amenities in Annapolis. This impressive property features an attached two-car garage, a private in-ground pool, and a pool house. In addition, there is a rear entry apartment with its own private deck. The spacious main residence offers five bedrooms and four-and-a-half bathrooms with comfortable living areas throughout. The beautifully renovated kitchen is designed for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, brand-new Bosch appliances and new flooring. In addition, the home has been thoughtfully upgraded with a new gas furnace and a newly completed fully finished basement with a bedroom and full bath (completed just two months ago) providing additional space for recreation, guests, a media room, or flex space. Adding even more space, the separate apartment, with its own rear entry, provides exceptional flexibility for extended family, guests or potential rental opportunities. Step outside to enjoy your own private backyard oasis featuring an in-ground pool and pool house, perfect for entertaining, relaxing, and enjoying the Annapolis lifestyle. Also, the Arundel Olympic Swim Center, Anne Arundel County’s largest public year-round indoor swimming facility, is across the street. There is also a 1.5 mile running trail nearby along with all the tennis courts and track at Annapolis High School, all open to the public after school hours. Conveniently located near downtown Annapolis, waterfront dining, shopping, parks, and major commuter routes including US-50 and MD-2, this remarkable property offers the perfect blend of comfort, convenience, and versatility. Mortgage savings may be available for buyers of this listing.

112 Speicher Dr, Annapolis

Listing courtesy of Redfin Corp. Contact: 4102028454

2 Beds ⋅ 2 Baths

Welcome to effortless luxury living in one of downtown Annapolis' most desirable condominium communities. This beautifully appointed 2-bedroom, 2-bath residence offers 1,206 square feet of thoughtfully designed living space, where sophisticated finishes and an unparalleled location combine to create an exceptional place to call home. The heart of the home is a stunning, fully renovated gourmet kitchen that has been meticulously updated from top to bottom. Featuring elegant quartz countertops, custom cabinetry, premium stainless steel appliances, and newer designer ceramic tile flooring, it is equally suited for everyday living and entertaining. Rich hardwood flooring extends throughout the remainder of the residence, creating a warm, timeless aesthetic that complements virtually any style. The spacious primary suite provides a private retreat, while the second bedroom and full bath offer outstanding flexibility for guests, a home office, or additional living space. Two deeded parking spaces in the secure garage provide the convenience and peace of mind that are increasingly rare in downtown Annapolis. Beyond your front door, you'll enjoy an extraordinary collection of resort-inspired amenities designed to enhance everyday living. Residents have access to a spectacular outdoor swimming pool, beautifully landscaped community patio and gathering areas, a fitness center, dog park, library, elegant clubhouse with a catering kitchen and billiards room, private meeting space, television lounge for entertaining, and the added comfort of a 24-hour concierge. The lifestyle extends well beyond the building itself. The community is home to three outstanding restaurants, boutique shopping, professional services, a convenient dry cleaner, and the Westin Hotel—perfect for hosting family and friends when extra accommodations are needed. With an impressive Walk Score of 83, you're just moments from the waterfront, Navy Football games, City Dock, the United States Naval Academy, award-winning restaurants, art galleries, shopping, entertainment, and countless year-round events that make Annapolis one of Maryland's most treasured destinations. This is the rare opportunity to enjoy all of the charm, culture, dining, and waterfront lifestyle that downtown Annapolis is known for—while leaving behind the maintenance, upkeep, and responsibilities of traditional homeownership. Simply lock the door, travel when you please, and come home to luxury, convenience, and an exceptional lifestyle every single day. Professional interior photos coming 8/10.

5 Park Pl Unit #603, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

2 Beds ⋅ 2 Baths

Beautiful 2 Bedroom 2 Bath Condo in Highly Desirable Four Seasons At St Margaret's..... Coming Soon!

1501 Broadneck Pl Unit #303, Annapolis

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

3 Beds ⋅ 3 Baths

Welcome to coastal living at its finest in Annapolis’ gated Chesapeake Harbour community! Enjoy sweeping marina views, fantastic people watching, and resort style amenities including 2 pools, tennis/pickleball courts, kayak access, walking trails, beaches, cocktails and entertainment at the dock bar and waterfront dining at The Beacon Restaurant. This sun drenched 3 bedroom, 3 full bath condo boasts high ceilings and a seamless floor plan made for entertaining. The upper level loft doubles as a flexible 3rd bedroom or home office, offering an airy, open concept layout that overlooks the main living area to maximize light and space. Don't miss this coastal gem!

2102 Chesapeake Harbour Dr E, Annapolis

Listing courtesy of Compass. Contact: (410) 429-7425

5 Beds ⋅ 6 Baths

Bay Ridge Waterfront! Built by Pilli Custom Homes and beautifully curated by Erin Paige Pitts Interiors, this exceptional waterfront residence blends timeless architecture, impeccable craftsmanship, and extraordinary attention to detail. Rich custom millwork, extensive crown molding, elegant wainscoting, and coffered ceilings create an atmosphere of refined luxury throughout. A welcoming bluestone walkway and front porch opens to the foyer, while a dramatic circular foyer at the foot of the staircase serves as the heart of the home, seamlessly connecting the formal dining room, elegant club room, and expansive kitchen and family room. Designed for effortless entertaining and everyday living, the chef's kitchen opens to the spacious family room featuring coffered ceilings and a striking fireplace. Just beyond, the waterside deck expands the living space with a swim spa, outdoor kitchen, and an exterior half bath, thoughtfully positioned so guests coming from boating, swimming, or relaxing by the water never need to enter the home. These exceptional amenities create the perfect setting for entertaining while embracing the waterfront lifestyle. Off the 2-car garage, the thoughtfully designed mudroom offers a built-in workspace, abundant storage, and a convenient powder room. A private main-level guest suite with an ensuite bath provides ideal accommodations for guests or multigenerational living. The upper level offers four spacious bedrooms, including two with private ensuite baths, while two additional bedrooms share a beautifully appointed bath. One bedroom has been transformed into a custom dressing room and can easily be converted back if desired. A large bonus room above the garage, complete with its own powder room, provides endless flexibility as a media room, playroom, home gym, or studio. The luxurious primary suite is a true retreat, featuring sweeping Lake Ogleton views from its wraparound balcony, a private office, spacious walk-in closet, and a spa-inspired bath with heated floors, soaking tub, oversized walk-in shower with built-in bench, and designer finishes. The top level is designed for entertaining with an expansive recreation room and a dramatic spiral staircase leading to one of the home's most remarkable features, a private rooftop deck perched among the highest elevations in Bay Ridge, offering breathtaking panoramic views and the perfect setting for morning coffee, sunset cocktails, or evening stargazing. Outside, the waterfront experience is equally impressive with a newly constructed pier featuring upgraded electrical service, LED lighting, three boat lifts, including an impressive 40,000-pound lift, and convenient waterside shed, providing exceptional accommodations for a variety of vessels and effortless access to the Chesapeake Bay. Bay Ridge offers an unmatched waterfront lifestyle with a community pool and clubhouse overlooking the Chesapeake Bay, sandy beaches on both the Bay and the river, a marina with a newly renovated clubhouse, playgrounds, basketball courts, ball fields, and miles of scenic waterfront roads for walking and biking. An active social calendar and year-round events make Bay Ridge one of Annapolis' most sought-after communities. Just minutes from Historic Downtown Annapolis and Eastport, enjoy award-winning restaurants, boutique shopping, marinas, and waterfront parks, with convenient access to Routes 50 and 97 for commuting to Baltimore, BWI Airport, Fort Meade/NSA, Washington, D.C., or Maryland's Eastern Shore. Welcome Home!

14 E Lake Dr, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

5 Beds ⋅ 5 Baths

Discover the pinnacle of contemporary waterfront living in this extraordinary new construction residence by Cypress Homes, perfectly sited on a spectacular peninsula along the picturesque Little Magothy River. Surrounded by water on two sides and offering a rare 525 feet of waterfrontage, this remarkable property captures sweeping panoramic views extending across the Magothy River to the Chesapeake Bay beyond. This custom crafted luxury home offers an exceptional blend of refined craftsmanship, timeless elegance, and an unparalleled waterfront lifestyle. Located within the highly acclaimed Blue Ribbon Broadneck School District and just minutes from downtown Annapolis, Severna Park, Baltimore, Washington, D.C., and BWI Airport, this residence offers the perfect balance of peaceful waterfront living and everyday convenience. Designed with meticulous attention to detail, every space has been thoughtfully curated to capture the spectacular water views while offering exceptional comfort for everyday living and entertaining. The dramatic foyer immediately impresses with a stunning floor to ceiling glass wine cellar before opening to expansive living spaces where walls of glass frame the shimmering waters of the river and pool beyond. The open concept design seamlessly connects the living room with fireplace and wet bar, an elegant dining area, and a gourmet chef's kitchen featuring premium appliances, custom cabinetry, and sleek designer finishes. A private main level bedroom with an ensuite bath provides ideal accommodations for guests, extended family, or a dedicated home office. An architectural open tread staircase leads to the upper level, where four additional bedrooms and three beautifully appointed baths await. The primary suite is a true waterfront sanctuary, offering breathtaking views, a private balcony overlooking the heated saltwater pool, a spa style bath, and generous walk in closets. An additional ensuite bedroom and two spacious bedrooms connected by a shared bath provide flexibility for family and guests, while the expansive bonus room above the garage is ideal as a media room, playroom, fitness studio, or additional guest retreat. Step outside to experience a waterfront setting few can rival. Whether relaxing beside the heated saltwater pool, entertaining along the water's edge, or enjoying the serenity afforded by this rare peninsula setting, the connection to the water is ever present. Launch a kayak or paddleboard from your private pier, spend the day crabbing and fishing, or cruise the protected waters of the Little Magothy River before venturing out for endless boating adventures. Offering the rare combination of new construction, 525 feet of waterfrontage, a peninsula setting with water on two sides, luxurious finishes, panoramic water views, and an unbeatable location, this is a home designed to be enjoyed for generations. A truly remarkable opportunity to experience one of Annapolis' most extraordinary waterfront estates. Welcome home!

1100 Magothy Cir, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

2 Beds ⋅ 2 Baths

Welcome to effortless living in the highly sought-after 55+ community of Heritage Harbour! This exceptional 2-bedroom, 2-bath villa has been completely renovated with quality craftsmanship and attention to detail throughout. Every major component has been thoughtfully updated, making this a truly move-in-ready home where you can simply unpack and begin enjoying the Heritage Harbour lifestyle. The beautifully redesigned kitchen features custom cabinetry, quartz countertops, updated flooring, modern lighting, designer tile backsplash, and a full suite of new stainless steel appliances. Both bathrooms have been completely renovated with stylish finishes, new vanities, upgraded fixtures, ceramic tile, and comfort-height toilets. Throughout the home, you'll find new carpeting, fresh paint, updated lighting, new door hardware, upgraded electrical switches and outlets, and numerous other improvements. The exterior has also been refreshed with updated lighting, new door hardware and weatherstripping, a tiled front entry, and a rebuilt and sealed rear deck—perfect for relaxing or entertaining. The bright, open floor plan is filled with natural light and offers comfortable everyday living with inviting spaces for gathering with family and friends. Every renovation was completed with an emphasis on quality, comfort, and low-maintenance living. Beyond your front door, Heritage Harbour offers one of the area's premier active adult lifestyles. Residents enjoy a 9-hole executive golf course, indoor and outdoor pools, tennis and pickleball courts, a fitness center, walking and biking trails, a community lodge overlooking the South River, a restaurant, kayak launch, boat slips, woodworking shop, library, billiards room, and more than 90 clubs, organizations, and social activities. This is a rare opportunity to own a beautifully renovated villa in one of Annapolis' most desirable 55+ communities. Schedule your private showing today and discover everything Heritage Harbour has to offer.

2729 Yeomans Lantern Ct, Annapolis

Listing courtesy of Academy Realty Inc.. Contact: (410) 263-9105

2 Beds ⋅ 3 Baths

COMING SOON IN SOUGHT AFTER HUNT MEADOW COMMUNITY. RARE, END UNIT TOWNHOUSE WITH FINISHED BASEMENT. PRIVATE LOCATION BACKING TO WOODS. WELL MAINTAINED. NATURAL GAS FIREPLACE & STOVE. LARGE DECK. COMMUNITY AMENITIES: POOL, SWIM TEAM, TENNIS/PICKLEBALL COURTS, BASKETBALL COURT, WALKING TRAIL. PEDESTRIAN ACCESS TO QUIET WATERS PARK.

19 Dorset Ct, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact: 4439012200

3 Beds ⋅ 2 Baths

HUGE PRICE REDUCTION $25,000.00 Welcome Home! Don't let summer slip away before you have the chance to relax by this beautiful pool while enjoying one of the best waterfront views around .This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool. This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage. A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit. Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading. Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops. This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.

755 Fairview Ave Unit #755 D, Annapolis

Listing courtesy of RE/MAX Leading Edge. Contact:

3 Beds ⋅ 3 Baths

This 3 bedroom, 2.5-bath home with a large finished basement provides great value. Located in The Landings, this Annapolis home has been loved and had money spent on it on things that matter. NEW ROOF in 2025. Updated high-end efficient windows. Updated sliding doors. Updated bathroom vanities. Updated HVAC. New flooring throughout. Updated cedar siding. The main level provides wonderful living and entertaining space filled with natural light and features a cozy log burning fireplace. The upper level offers THREE bedrooms with wonderful natural light. The primary bedroom features a vaulted ceilings and its own en-suite bathroom; it is bright and spacious. The basement level includes large laundry room and a large living area that could easily be used as a media room or home office. The rear of the home offers a private deck looking out to a community greenspace which is perfect for relaxing or entertaining. The front of the home offers spacious parking. Ideally located, this home has easy access to Routes 50 and 97 but yet is minutes from downtown Annapolis’s shopping, dining, and waterfront attractions. Community amenities are substantial and include two pools, four pickleball courts and two tennis courts. The community cuts the grass and maintains the grounds... this is carefree living. This townhome is a must see!

6 Tiburon Ct, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

3 Beds ⋅ 3 Baths

COMING SOON!!!!!! One of the nicest lots in Heritage.

1302 Homewood Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: kelly.thompson@cbmove.com

3 Beds ⋅ 3 Baths

Experience the ultimate waterfront lifestyle in the prestigious Harbour Village Marina at Chesapeake Harbour, where panoramic marina views and exceptional amenities create one of Annapolis' most sought-after communities. This beautifully updated 3 bedroom 3 bath waterfront condominium offers an inviting blend of elegance, comfort, and coastal charm. Wake each morning to tranquil marina views from your private balcony, spend your afternoons enjoying the private sandy beach, waterfront pool, tennis and pickleball courts, or simply watch the boats come and go from one of the area's premier marinas. Whether you're an avid boater or simply appreciate life on the water, this is waterfront living at its finest. Inside, the spacious floor plan is designed for both everyday living and effortless entertaining. The living room and primary suite each feature a gas fireplace, creating warm and inviting spaces to unwind. Multiple balconies capture beautiful marina vistas, while the updated kitchen showcases granite countertops, stainless steel appliances, and generous workspace for preparing meals or gathering with family and friends. Thoughtful upgrades throughout the home provide both style and peace of mind, including fresh interior paint, engineered hardwood flooring, updated granite countertops, designer bathroom vanities with quartz countertops, newer interior doors with brushed bronze hardware and glass door knobs, LED ceiling lighting, Lutron switches, modern 15-amp outlets with USB and USB-C charging ports, and numerous electrical improvements. The oversized two-car garage with EV charging capability adds convenience for today's lifestyle. Residents of Chesapeake Harbour enjoy an unmatched collection of waterfront amenities, including a private beach, marina, waterfront swimming pools, tennis and pickleball courts, walking paths, and the popular Beacon Waterfront Galley & Bar...all within the gated community. No other condominium community in Annapolis offers this unique combination of waterfront recreation, boating, dining, and resort-style living. Whether you're searching for a full-time residence, an elegant weekend retreat, or the perfect lock and leave waterfront home, this exceptional condominium offers a rare opportunity to enjoy the Chesapeake Bay lifestyle in one of Annapolis' most exclusive waterfront communities.

7038 Clinton Ct Unit #11B, Annapolis

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

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