Browse All Annapolis MD Properties with Pool for Sale

BIG $50K PRICE REDUCTION ON THIS BEAUTIFUL 2 BR UNIT! Look no further! This Chesapeake Harbour marina view condo, is available immediately in one of Annapolis' most sought after waterfront communities. This beautifully renovated 2 BR | 2 BA | 1200 SF condo on the second level is truly turn key offering over $100K in high end improvements crafted with top of the line materials throughout. Enjoy stunning tranquil marina views from your deck and living space, creating a peaceful coastal retreat. The sumptuous Primary Suite features access to deck, a spa-inspired Bath with an impressive walk in shower and custom closet with built-ins. Recent updates include new carpet throughout and a new oversized water heater, ensuring comfort and peace of mind. Residents of Chesapeake Harbour enjoy an exceptional lifestyle with front entrance security , waterfront dining at the Beacon Waterfront Bar, marina access, waterfront pools, tennis, private beach and walking trails and just minutes to Downtown Annapolis.

7022 Channel Village Ct Unit #101, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$568,000

4 Beds ⋅ 3 Baths

Elegant brick and siding split-foyer residence offering 4 bedrooms and 3 renovated full bathrooms on a beautifully sized 0.21-acre lot. The thoughtfully designed upper level features a sun-filled living room, formal dining area, well-appointed brand new kitchen with new appliances, and seamless access to the rear deck—perfect for refined indoor-outdoor living. Three bedrooms and two full baths complete the main level. The lower level is highlighted by a private primary suite with a generously renovated full bathroom, providing an ideal owner’s retreat or guest quarters, along with a spacious family/recreation room, laundry area, and mechanical room. Luxury vinyl flooring extends throughout both levels, complemented by windows in excellent condition. Major updates include the roof and HVAC system. Serviced by well and public sewer. A well-maintained home offering comfort, privacy, and timeless appeal.

721 Fairway Dr, Annapolis

Listing courtesy of KW Metro Center. Contact: 7032246000

$1,157,456

4 Beds ⋅ 4 Baths

Foreclosure opportunity in sought-after Annapolis! Spacious 4BR/3.5BA Colonial with over 4,500 sq ft of living space. Features include multiple living areas, large kitchen footprint, finished lower level, and generous bedroom sizes. Private backyard with in-ground pool ready to be restored. Excellent potential for renovation or investment. Convenient to shopping, dining, major routes, and downtown Annapolis. Sold strictly AS-IS. Schedule your showing now!

371 Carriage Park Way, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

$624,900

2 Beds ⋅ 2 Baths

Welcome to the gated community of Chesapeake Harbour, offering a stress-free lifestyle! This second-floor condo features two balconies. The large wrap-around balcony provides stunning views of the marina, while the second balcony, located off the kitchen, offers views of the bay. Inside, the main level features an open-concept living area and a spacious kitchen with stainless steel appliances and abundant cabinet and counter space. The primary suite is also located on this level. Up the beautiful spiral staircase, you will find a loft/bedroom and an additional sitting area. Chesapeake Harbour provides residents with a swimming pool, tennis courts, a beach, and much more. You are also within walking distance of the marina, shopping, and restaurants.

2106 Chesapeake Harbour Dr Unit #202, Annapolis

Listing courtesy of Keller Williams Realty. Contact: 3028467839

$305,000

3 Beds ⋅ 2 Baths

Spring has arrived, and this beautifully updated 3-bedroom, 2-bath condo offers the perfect opportunity to enjoy the best of the Annapolis lifestyle. Located on the 3rd floor, this light-filled home combines modern upgrades, comfort, and unbeatable access to outdoor recreation and waterfront attractions. Inside, the open-concept living, dining, and kitchen area creates a warm and inviting flow, complete with a cozy fireplace—perfect for relaxing after a day on the water or exploring the city. The renovated kitchen (2022) features granite countertops, farmhouse sink, stainless steel appliances, and contemporary cabinetry designed for both everyday living and entertaining. Brand-new windows (2021) fill the home with natural light. The spacious primary suite includes a private en-suite bath and direct access to a walkout patio overlooking the community pool—an ideal spot for morning coffee, evening sunsets, or enjoying the spring breeze. Generous closet space throughout and updated bathroom finishes add to the home’s appeal. For buyers who love the outdoors, this location is exceptional. Just minutes away, enjoy scenic walking and biking trails, waterfront views, picnic areas, dog-friendly spaces, and seasonal outdoor activities at Quiet Waters Park, a local favorite with over 300 acres of trails and water access. You’re also moments from Historic Downtown Annapolis, Spa Creek, Back Creek marinas, waterfront dining, kayaking, sailing, and Chesapeake Bay attractions, making it easy to enjoy the coastal lifestyle that makes Annapolis so desirable. Community amenities include a swimming pool and convenient pet stations for easy living. Whether you're looking for a primary residence, a low-maintenance coastal retreat, or a home close to parks and the waterfront, this condo offers outstanding value and location. Now is the perfect time to make your move—schedule your private showing today and experience spring in Annapolis at its best.

10 Sandstone Ct, Annapolis

Listing courtesy of Smart Realty, LLC. Contact: 3012525515

$275,000

1 Beds ⋅ 1 Baths

Wonderful Price Reduction - Motivated Seller!! Perhaps the finest Annapolis has to offer...A premiere, resort style retirement living option for those 60+ Time to let someone one else take care of the daily cooking and cleaning, you only need to relax, socialize with your friends and enjoy all Annapolis, Md has to offer! One monthly fee takes care of ALL utilities, daily meal, weekly cleaning, taxes, insurance, garage parking, maintenance/replacement of all appliances and HVAC. You've earned this!

7101 Bay Front Dr Unit #301, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

$500,000

2 Beds ⋅ 2 Baths

The Seasons change the views. Tremendous price reduction. See the virtually staged photos of the living room. A great opportunity just before the summer. Quiet tranquil setting for this 2 bedroom 2 bath unit with a view of the Bay in the distance, Windows in second bedroom replaced in 2024. To be sold in As-is condition. Enjoy the community amenities - 24 hour security, swimming pools, tennis courts, a beach and walking trails. Bay Ridge Rd. to Route 50 and 97 to DC and Baltimore. Easy to show, just call Showings to log in.

2010 Quay Village Ct Unit #101, Annapolis

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

$1,250,000

3 Beds ⋅ 2 Baths

769 Robinhood Road is one of the most desirable Waterfront properties in Sherwood Forest. Uniquely situated on a point you will enjoy river breezes from your living room and front porch while experiencing stunning views of the Severn River Bridges into Annapolis and down the Idle toward the Sherwood Forest Marina. On a clear day you can see the Eastern Shore! Watch as sail boats, wind surfers and yachts cruise by your front porch. Another unique benefit of 769 is that, unlike many of the Sherwood properties, it has ample parking for 5+ cars. This 1 level, 3 bedroom, 2 bathroom home, has been in the same family since 1940. Included in the listing documents are a home inspection report, already developed building plans, and information about a brand new septic in the works. Home is being sold AS IS. Take advantage of the varied Club amenities while you savor one of the best views in all of Sherwood Forest. **Sherwood Forest is a gated Community of 341 homes, situated on the Severn River. It's peninsula shape and sweeping elevations create gorgeous vistas of the surrounding creeks, river and the Severn River Bridge. **Walk along the 2 mile waterfront road and take in bridges framing the mouth of the Chesapeake Bay. **Bike or hike the 5 miles of outer Forest trails. Most residents prefer their Golf Carts for easily navigating the scenic hills. **Established in 1915, the Community is anchored by a grand nostalgic Clubhouse which overlooks the Community Pool - and houses a Dance Hall, Duckpin Bowling Alley, a Stage for Community Productions, a Grand Stone Fireplace, Library, and a Nature Lab for educating the children about Chesapeake life. Members enjoy many events at the Clubhouse including Community Dances, Anniversary Celebrations, and Cultural Arts Presentations. The Clubhouse is available to members to rent for Weddings or Private Events. ** The Sherwood Forest Market serves ready-made meals and stocks staples for your cottage kitchen. ** Sherwood is known for the Children's Summer camp where your children learn numerous activities including Sailing, Swimming and Archery. **Other outstanding amenities are a 9-Hole Golf Course, Tennis Courts, Pickleball Courts, Basketball Court, Badminton, Softball field and a Lacrosse/Soccer field. ** For the Chesapeake lovers, Sherwood has a Marina, a , Small Piers and a Main Pier where river swim meets are held. **Make memories with events like the 3rd of July Fireworks, 4th of July Parade and and Annual "not be be missed" Corn Roast. There are tennis, golf and pickleball tournaments for adults and children alike. *With a purchase of a home, Sherwood Forest requires a one-time $20,000 club membership fee.

769 Robinhood Rd, Annapolis

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

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Annapolis Homes with Pool

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