Queen Annes Homes with Pool

Queen Annes Homes with Pool

Welcome to Queen Anne’s County, Maryland, a picturesque gem nestled on the Eastern Shore. Known for its serene landscapes and charming small towns, this county offers a perfect blend of natural beauty and vibrant community life. With its stunning waterfront views, lush parks, and rich history, Queen Anne’s County is an ideal place for both relaxation and adventure.

One of the most enticing features of homes in this area is the availability of properties with pools. Imagine stepping out into your own backyard oasis on a warm summer day, where you can unwind in your sparkling pool while enjoying the gentle breeze and the sounds of nature. Whether you’re hosting a lively barbecue with friends or enjoying a quiet evening under the stars, a pool adds a touch of luxury and leisure to your home.

Queen Anne’s County boasts a variety of homes with pools, catering to diverse tastes and lifestyles. From charming single-family homes to luxurious estates, you’ll find properties that not only meet your needs but also enhance your quality of life. The local real estate market is thriving, offering a range of options that suit both first-time buyers and those looking for their dream retreat.

Beyond the allure of private pools, Queen Anne’s County is rich in recreational opportunities. With access to the Chesapeake Bay, hiking trails, and local parks, you can enjoy an active outdoor lifestyle. The county also hosts a variety of community events, fostering a strong sense of belonging among residents.

Discover the beauty of Queen Anne’s County and the joy of owning a home with a pool—your personal sanctuary awaits!

Newest Queen Annes Homes with Pool

4 Beds ⋅ 3 Baths

A must see home! Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home!

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact: (410) 823-0033

3 Beds ⋅ 2 Baths

Enjoy comfort, convenience, and scenic surroundings in this lovely3‑bedroom, 2‑bath condo located in the desirable Thompson Creek community. This inviting home features a cozy living room fireplace and a peaceful pond view, creating a warm and relaxing atmosphere year‑round. Residents benefit from outstanding community amenities, including a walking trail, outdoor pool, and fitness center. Perfectly situated for easy access to the Bay Bridge, local shopping, dining, and commuter routes, this location offers both practicality and lifestyle appeal. A wonderful opportunity to enjoy low‑maintenance Eastern Shore living in a beautifully maintained community.

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact: (443) 988-0483

3 Beds ⋅ 3 Baths

Welcome to Your Dream Home at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Lille Loft model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors. A chef's dream, the Gourmet Kitchen is the heart of the home, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining, and a separate beverage center! Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers a spacious loft, a flexible area perfect for a second family room, hobby space, and an additional bedroom and bathroom for overnight guests. Also, the large above attic storage room is fully finished. More storage is available in the oversized fully finished two car garage with extra room for a golf cart. Off the dining area is a screened-in porch and patio, and the community run irrigation system to keep your lawn lush and green! You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis (17 miles), DC (45 miles), Baltimore (45 miles), and BWI (30 miles). Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by endless views of the Chester River.

193 Spinnaker Way, Chester

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

3 Beds ⋅ 4 Baths

***COMING SOON!!*** Get ready for this beautifully updated end-unit townhome! Recently painted in coastal-inspired colors throughout, this home offers an abundance of recent updates, including new flooring, new kitchen countertops, appliances, a beautifully updated primary bath with a walk-in shower, stone refacing on the fireplace, and so many more improvements than I can list. All I can say is... get ready to be impressed! Not only does this townhome show beautifully, but it's also perfectly positioned with close proximity to Ellendale's clubhouse, pool, and playground, providing easy access to family fun. Featuring 3 bedrooms PLUS an office/den or optional 4th bedroom, 2 full baths + 2 half baths, and a rear-entry 2-car garage, this home checks all the boxes. The large deck off the kitchen provides the perfect extension of your living space for outdoor dining, morning coffee, or evening beverages. Location is key, as we know ...and this one delivers! With Kent Island's amenities just minutes away and the Chesapeake Bay Bridge only 2 minutes from your door... HELLO easy commute! You'll also be just minutes from wonderful waterfront dining, spa, resorts, marina, parks, public beach, schools, shopping, and so much more. Don't miss this one, it's the low-maintenance lifestyle you've been waiting for! COME SEE IT TODAY!!

101 Branta Lndg, Stevensville

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

4 Beds ⋅ 5 Baths

Welcome to this like-new, impeccably maintained stone front end-unit townhome offering four finished levels of thoughtfully designed living space, 4/5 bedrooms, 4.5 bathrooms, and numerous custom upgrades throughout. Perfectly located just one mile from the Chesapeake Bay Bridge, this stunning home combines modern luxury with the convenience of Eastern Shore living. You are welcomed to the home by a partial wrap around porch, ideal for decorating and offers coverage for deliveries. Inside you will discover a beautifully updated interior with all four levels of stairs completely renovated with new flooring (2026), representing a $10,000 investment, luxury vinyl plank flooring, new carpet in bedrooms (2025), fresh designer paint, custom blinds, and timeless finishes that make this home truly move-in ready. The heart of the home is the gourmet kitchen, complete with Quartz countertops, stainless steel appliances, gas range, custom lighting, a large center island with breakfast bar, and a custom-built coffee bar featuring its own beverage refrigerator. Just off the kitchen, enjoy a separate dining area and access to the private balcony; perfect for morning coffee or evening relaxation. The inviting living room is warm and welcoming with a custom shiplap accent wall and an electric fireplace, creating the perfect space for entertaining or cozy nights at home. The spacious Primary suite offers a walk-in closet and a beautiful bath featuring a custom tiled shower, tile flooring, and a double vanity. Two additional bedrooms, another full bath, and a thoughtfully designed laundry room complete the bedroom level. The laundry area includes a newer washer and dryer, linen closet, and a dedicated folding and sorting station for added convenience. The impressive fourth floor offers incredible flexibility with a bonus room ideal as a guest bedroom, home office, or playroom. This level also includes a full bathroom, two storage closets with 15x20 attic access for additional storage, and a large private balcony. The finished lower level provides even more living space with a family room, recreation room, or optional fourth bedroom, complete with its own full bathroom. The attached two-car garage is fully finished with heating and air conditioning unit, interior water spigot, and plenty of storage. Additional upgrades include: *Approximately $10,000 in new stair flooring (2026) * New luxury vinyl plank flooring and carpet throughout (2025) * New stainless steel appliances * Electric fireplace * Dual-zone HVAC * Gas heat * Gas Hot water heater * Full-house sprinkler system * Freshly painted interior * Beautiful custom finishes throughout. Beyond the home, you'll enjoy resort-style community amenities including a clubhouse, swimming pool, playground, scenic walking trails, RV and boat storage, a community fishing pier, and kayak launch; perfect for embracing the Chesapeake Bay lifestyle. Experience everything that makes Kent Island one of Maryland's most desirable waterfront communities. Spend weekends boating, fishing, crabbing, kayaking, or paddleboarding on the Chesapeake Bay. Explore miles of scenic walking and biking trails, relax at nearby beaches, visit local wineries, browse the charming shops of Historic Stevensville, or enjoy fresh seafood and waterfront dining along Kent Narrows. Whether you're watching breathtaking sunsets over the Bay, launching your kayak from the community pier, or heading to one of the area's many marinas, Kent Island offers the perfect balance of recreation, natural beauty, and small-town charm; all while remaining an easy commute to Annapolis, Baltimore, Washington, D.C., and the rest of Maryland's Eastern Shore. This exceptional home offers the perfect combination of luxury, location, and low-maintenance living. Simply unpack and enjoy! Dog friendly home. Buyer to verify all HOA fees, documents, and community information through the resale package.

222 Jessica Lyn Ave Unit #G5, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

3 Beds ⋅ 2 Baths

Get ready to be wowed!!! This home has undergone an extensive renovation over the last 5 years. The owners have poured so much love into this home, and it shows. On the interior one of the big standouts is the gourmet kitchen that will surely be the heart of the house. From the granite counters to the 10x4 quartz center island with seating and a built in beverage fridge, to the cozy built in window seating. The living area offers a great pellet stove for those chilly winter nights. Two bedrooms off the living area share a beautifully updated hall bath. The second sitting area is the family room that has a custom pine ceiling and direct access to your Trex deck to enjoy your morning coffee. But wait till you see the primary bedroom with a built in electric fireplace to cozy up too! Cold feet in the mornings no more with the heated primary bath floor, gorgeous shower with rainfall shower head and dual vanities. The exterior of this home is just as amazing as the interior. Get ready all you motorheads for this 30x46 outbuilding with 12 ft ceiling, 200-amp electric service, 2 automatic garage doors, a 18x10 bump out and a craft room for an added bonus! But wait there's more! The above ground pool was just purchased in 2022, with extensive decking for lounging about, or maybe an afternoon cocktail at your own tiki bar. Tired of having to purchase new plants every season well now you can safely store them over the winter in your own 10x12 greenhouse. The backyard even offers a great firepit area for those chilly evenings. Don't take my word for it come and experience all this property has to offer for yourself, you won't be disappointed!

2702 Harrington Rd, Chester

Listing courtesy of Rosendale Realty. Contact: 4107580333

2 Beds ⋅ 3 Baths

Welcome to the Taylor, a beautifully designed home that offers the perfect blend of comfort, style, and convenience. Available now, this home features 2 bedrooms, 2.5 baths, and a spacious 3-car garage, making it ideal for those seeking both functional living and elegant design. The open-concept layout is enhanced by a cozy fireplace and decorative ceiling beams that add warmth and architectural charm to the main living area. Step outside to the screened patio, where you can relax and take in peaceful waterfront views, creating the perfect setting for morning coffee or evening gatherings. The kitchen is equipped with a full suite of appliances, and a washer and dryer are also included, allowing you to move in with ease and enjoy modern convenience from day one. The primary bath features a spacious walk-in shower, offering a comfortable and spa-inspired retreat to unwind at the end of the day. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

216 Kingfisher Ln, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

2 Beds ⋅ 3 Baths

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit #2912, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500

5 Beds ⋅ 3 Baths

Your private resort awaits. From the moment you arrive, this stunning home commands attention with its timeless curb appeal, oversized corner lot, and impressive presence. Offering over 5,000 square feet across three levels, this is the perfect blend of luxury, comfort, and everyday functionality. Step inside to soaring ceilings, abundant natural light, and an open floor plan designed for both entertaining and daily living. The spacious two-story family room with a cozy fireplace flows seamlessly into the heart of the home, a beautifully appointed kitchen featuring a large center island, granite countertops, stainless steel appliances, abundant cabinetry, beverage refrigerator, and an oversized breakfast area overlooking the backyard. Whether you're hosting holiday dinners in the formal dining room, enjoying quiet mornings in the sun-filled living spaces, or gathering with friends around the kitchen island, every room has been thoughtfully designed for making memories. Upstairs, the expansive primary suite offers a true retreat with a spa-inspired ensuite bath, generous walk-in closet, and plenty of room to unwind. Spacious secondary bedrooms provide flexibility for family, guests, or a home office. The basement level adds even more living space with endless possibilities for a recreation room, fitness area, media room, or additional guest accommodations. Then step outside... The backyard is where this home truly shines. Imagine summer afternoons spent in the sparkling in-ground pool, evenings under the custom pavilion complete with an outdoor kitchen and bar, relaxing around the fire pit, and entertaining on the expansive paver patio, all surrounded by a fully fenced backyard offering privacy and space to enjoy. This isn't just a backyard, it's your own private vacation destination. Conveniently located near shopping, dining, parks, schools, and major commuter routes, this exceptional home offers the lifestyle you've been waiting for. Luxury. Space. Resort-style living. Welcome home.

122 Fair Brook Way, Centreville

Listing courtesy of RE/MAX Executive. Contact: 4432741900

2 Beds ⋅ 2 Baths

Welcome to coastal living in this beautifully updated first-floor, end-unit condo, offering the perfect blend of comfort, convenience, and resort-style amenities in one of Kent Island's most sought-after communities. With no stairs to navigate and handicap-accessible features, this home provides effortless everyday living while enjoying the added privacy and abundant natural light that only an end unit can offer. The beautifully updated kitchen features quartz countertops, a breakfast bar, newer stainless steel appliances, and abundant cabinetry, making it as functional as it is stylish. The adjoining dining area flows seamlessly to the private deck through sliding glass doors, bringing the outdoors in and making entertaining a breeze. HVAC and washer/dryer are less than 4 years old. The spacious primary suite serves as a relaxing retreat with a large walk-in closet and private ensuite bath. A second generously sized bedroom offers exceptional flexibility for guests, a home office, or family visits, while elegant plantation shutters add timeless charm and character to both bedrooms. Life at Bayside is about much more than the home itself. Residents enjoy a truly maintenance-free lifestyle, with exterior maintenance and community upkeep handled by the condominium association, leaving more time to enjoy everything Kent Island has to offer. Community amenities include a clubhouse, swimming pool, fitness center, tennis courts, beautifully landscaped grounds, and Castle Marina just a short walk away. Outdoor enthusiasts will appreciate being only steps from the Cross Island Trail, offering miles of scenic walking and biking paths showcasing the natural beauty of the Chesapeake Bay. Ideally located near waterfront dining, shopping, and local attractions, this home also provides easy access to Route 50 and the Chesapeake Bay Bridge, international airports and coastal beaches, making commuting and travel exceptionally convenient. Where every day feels like a vacation—and the only thing left to maintain is your schedule.

302 Merganser Ct Unit #A, Chester

Listing courtesy of Keller Williams Flagship. Contact:

1 Beds ⋅ 1 Baths

Bring your vision to one of the most affordable condos currently available in Queen’s Landing. This one-bedroom, one-bath unit offers approximately 640 square feet and is priced well below its tax-assessed value to reflect its original interior condition, giving buyers the flexibility to update and personalize the space to suit their own style. The condo overlooks Lake Amletto, offering a pleasant water view and the relaxing sound of the nearby fountain, while the Chester River is just a short walk away across the street. One-bedroom units benefit from a lower monthly condominium fee while still enjoying access to the community’s many amenities, including the waterfront pool, clubhouse, fitness center, pickleball and tennis courts, walking paths, marina setting, and beautifully maintained grounds. For a water-oriented lifestyle, boat slips may also be available for purchase or rental within the community, subject to availability. Whether you are looking for an affordable entry into Queen’s Landing, a renovation project, an investment opportunity, or a weekend retreat near the water, this property offers plenty of potential.

26 Queen Anne Way, Chester

Listing courtesy of Realty Navigator. Contact: 4106433404

5 Beds ⋅ 3 Baths

Classic Colonial Overlooking the Golf Course in Prospect Bay. Welcome to this beautifully maintained brick-front Colonial, perfectly positioned with picturesque golf course views in the sought-after Prospect Bay community. Filled with natural light from oversized windows, the open floor plan offers the perfect balance of comfortable everyday living and elegant spaces for entertaining. The home features four spacious bedrooms upstairs, plus a first-floor office or optional fifth bedroom, making it ideal for guests, multi-generational living, or working from home. Hardwood floors, two fireplaces, a formal dining room, and generously sized living spaces create timeless appeal throughout. The spacious primary suite offers a peaceful retreat with a walk-in closet and private bath. A three-car garage provides ample storage and convenience. Step outside to your private backyard oasis, where a heated swimming pool, expansive deck with a covered awning, and sweeping golf course views create the perfect setting for relaxing or entertaining. Enjoy watching golfers from your backyard while soaking in the peaceful surroundings. Living in Prospect Bay means enjoying resort-style amenities, including an 18-hole championship golf course, clubhouse with members-only restaurant and bar, marina with boat launch, swimming pool, tennis and pickleball courts, playground, and a full calendar of year-round social events. This exceptional home offers the perfect blend of classic elegance, modern comfort, and an unbeatable lifestyle.

4 Prospect Bay Dr W, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686

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