Anna Maria Homes with Pool Community Features

Anna Maria Homes with Pool Community Features

Welcome to Anna Maria, Florida, a picturesque island city that embodies the quintessential charm of coastal living. Nestled on the stunning Gulf Coast, Anna Maria is renowned for its pristine beaches, vibrant local culture, and a laid-back atmosphere that invites relaxation and enjoyment. With its rich history and friendly community, this idyllic destination offers a unique blend of small-town warmth and natural beauty.

Anna Maria is not just a place to visit; it’s a lifestyle. The city boasts a variety of homes that cater to those seeking the ultimate Florida experience, especially for families and individuals who cherish outdoor living. Many properties in Anna Maria come with private pools, allowing residents to soak up the sun in their own backyard oasis. Imagine sipping your morning coffee by the poolside or hosting delightful summer barbecues with friends and family, all while surrounded by the lush tropical landscape that defines this enchanting locale.

In addition to the luxurious homes with pool community features, Anna Maria offers an array of recreational activities. From kayaking through tranquil waters to exploring the scenic nature trails, the island is a haven for outdoor enthusiasts. The vibrant local dining scene, boutique shopping, and art galleries further enhance the charm of this coastal gem.

Whether you’re looking to invest in a vacation home or seeking a permanent residence, Anna Maria, Florida, promises a lifestyle filled with sunshine, community, and endless opportunities for adventure. Discover your dream home in this idyllic paradise and experience the magic of Anna Maria for yourself!

Newest Anna Maria Homes with Pool Community Features

1722 W Del Webb Boulevard, Sun City Center
$219,900
2 Beds ⋅ 2 Baths ⋅ Del Webbs Sun City Florida Un SubDv. ⋅ 33573 Zip Code
Virtually Staged. Welcome to this charming 2-bedroom, 2-bathroom, 1,369-square-foot single-family home located in the heart of Sun City Center. Curb appeal abounds with a beautifully paved driveway, mature palm trees, and distinctive stone accent trim framing the front exterior. Inside, the home offers a flexible layout featuring a spacious main living area, a dedicated dinette nook, and an expansive secondary living or sitting room illuminated by large windows. The functional kitchen comes well-equipped with abundant cabinetry and a stylish tiled backsplash, while a generous dedicated laundry room provides built-in shelving and extra storage capability. The primary suite is comfortably sized with built-in closet space and an en-suite bath featuring a walk-in shower. The second bedroom also offers generous closet space with convenient access to a full hall bathroom with a tub/shower combo. Enjoy Florida living year-round in the large enclosed sunroom overlooking a great, serene backyard with no rear neighbors. Adding even more peace of mind is a brand-new roof installed in 2026. You’ll love Sun City Center with its amazing facilities, pools, and clubs just waiting for you to enjoy. Nestled between Sarasota and Tampa, this location offers a convenient ride to airports, great shopping, dining, and professional entertainment. With easy access to award-winning, sandy beaches, this home provides the best of all worlds without the stress of big city life. Leave it all behind and enjoy your new life here in one of Florida’s most affordable 55-and-better communities!

1722 W Del Webb Boulevard, Sun City Center

2617 Cove Cay Drive Unit 604, Clearwater
$225,000
2 Beds ⋅ 2 Baths ⋅ Cove Cay 26-17 Village I SubDv. ⋅ 33760 Zip Code
Discover the beauty of waterfront living in this stylishly updated 2-bedroom, 2-bath condo at sought-after Cove Cay Village 1 in Clearwater. Perched on the 6th floor, this 1,050 sq ft home offers sweeping views of Old Tampa Bay from the main living areas and enclosed porch, creating a peaceful, coastal backdrop to everyday life. Step inside to a light-filled, open layout accented with sleek tile flooring throughout. The kitchen stands out with granite countertops, crisp white cabinetry, matching appliances, and a tray ceiling with crown molding detail. Recent upgrades include a brand-new kitchen faucet and updated plumbing, adding both style and functionality. The adjoining dining area flows seamlessly into the oversized living room, where a wall of windows frames the sparkling bay. The primary suite features a generous walk-in closet and an ensuite bath with dual sinks and a walk-in shower. The second bedroom is well-sized and situated near the guest bath with a tub/shower combination. Your own private laundry and storage room—located just steps from the front door on the same floor—offers convenience and extra space. Cove Cay Village 1 delivers a resort-like lifestyle with a renovated clubhouse, card and social rooms, sauna, fitness center, heated pool and spa, and shuffleboard courts. Optional memberships are available for golf at the Cove Cay Golf Club or boating at the Cove Cay Marina. With its prime location, upgraded finishes, and unmatched water views, this home is move-in ready for your next chapter in Florida living. Schedule your private showing today. Kitchen appliances, countertop, cabinets done in 2017. Primary bath full upgrade 2017, tile floor throughout 2017, roof replaced 2020. Some electrical outlets updated 2025, interior paint 2023, kitchen faucet and plumbing 2025. New A/C 2022. Brand new sliding windows in living room 2026. Primary Bath painted 2026.

2617 Cove Cay Drive Unit 604, Clearwater

11624 Foxworth Lane, New Port Richey
$255,999
2 Beds ⋅ 2 Baths ⋅ Summertree 01a Ph 01 SubDv. ⋅ 34654 Zip Code
Welcome to easy Florida living in the desirable 55+ community of Summertree! This immaculately maintained 2-bedroom, 2-bath villa is ideally situated on a spacious corner lot near the end of a quiet cul-de-sac, offering added privacy and a peaceful wooded backdrop. Recent improvements include a NEW HVAC system in 2026, fresh interior paint, and new appliances, making this home truly move-in ready. Inside, you’ll find a bright, comfortable floor plan with generous living spaces and plenty of natural light. The kitchen offers plenty of cabinet and counter space, a convenient pass-through overlooking the living area, and stainless steel appliances. The spacious primary suite features a large en-suite bath with dual sinks, walk-in shower, and walk-in closet, while the secondary bedroom and guest bath provide a welcoming space for visitors. Enjoy Florida living year-round from the screened lanai, overlooking the back yard with mature trees and no homes directly behind you. The inside laundry room offers additional cabinetry, utility sink, and convenient storage, while the attached 2-car garage and oversized driveway provide plenty of parking and functionality. And then there’s the Summertree lifestyle! This 55+ community offers an active and social atmosphere centered around a beautiful clubhouse overlooking the community’s scenic 9-hole golf course. Residents enjoy a heated pool and spa, fitness facilities, tennis, pickleball, bocce, shuffleboard, billiards, arts and crafts, and a variety of clubs, classes, social gatherings and activities. Nature lovers will appreciate the community’s peaceful natural surroundings, scenic ponds, abundant Florida wildlife and deer, along with sidewalks and walking areas that make it enjoyable to get outside and take a leisurely stroll or go on a bike ride. Whether you want to stay active, meet neighbors and make new friends, play a round of golf, relax by the pool, or simply enjoy the tranquility of the natural surroundings, Summertree offers the opportunity to enjoy as much—or as little—of the active Florida lifestyle as you choose. Conveniently located near shopping, dining, medical facilities, major roadways, this home combines comfortable living, privacy, and an active 55+ community lifestyle. Major updates are already done—move in, relax, and start enjoying everything this home has to offer!

11624 Foxworth Lane, New Port Richey

4750 Dolphin Cay Lane S Unit 107, St Petersburg
$575,000
2 Beds ⋅ 2 Baths ⋅ Dolphin Cay Dominica SubDv. ⋅ 33711 Zip Code
Discover a nature lover’s paradise in the lush waterfront community of Dolphin Cay. This rare first-floor residence in the Dominica building offers the perfect blend of coastal serenity and effortless indoor-outdoor living. Meticulously maintained and thoughtfully designed, the home features a spacious open floor plan that flows seamlessly onto an extraordinary private veranda and expansive outdoor deck spanning the full width of the residence—an exceptional space to enjoy peaceful garden views, coastal breezes, and the surrounding tropical landscape. Inside, hurricane-rated windows and sliding doors invite natural light while framing tranquil views of the beautifully landscaped grounds. The living room, dining area, and open kitchen create a welcoming environment ideal for both everyday living and entertaining. The primary suite is a relaxing retreat featuring 8-foot sliding glass doors that open directly to the outdoor deck, a custom walk-in closet, additional linen storage, and a spacious primary bath. A private guest bedroom with plantation shutters enjoys picturesque views of mature palms and lush landscaping, offering comfort and privacy for visiting guests. The versatile bonus room with distinctive barn doors is currently used as a home office but is generously sized and easily adaptable as a third bedroom, den, or creative studio. Located in the Dominica building directly across from the lake, the association has completed its Structural Integrity Reserve Study and has recently undergone significant improvements including a new roof, new elevators, exterior painting, and enhanced landscaping. Residents of Dolphin Cay, a gated 88-acre waterfront nature preserve, enjoy an exceptional resort-style lifestyle with amenities that include:Three heated waterfront pools and spa, Private beach and fishing pier, Kayak launch and waterfront walking trails, Three Har-Tru lighted tennis courts, Fitness center and waterfront grilling areas, Clubhouse with billiards room and library. On-site professional management. Perfectly positioned, Dolphin Cay is just minutes from the vibrant arts scene, waterfront parks, and renowned dining of Downtown St. Petersburg, as well as the sugar-sand beaches of St. Pete Beach and Pass-a-Grille. Tampa International Airport and St. Pete-Clearwater International Airport are both easily accessible. An exceptional opportunity to enjoy peaceful waterfront living surrounded by nature while remaining close to the best of St. Petersburg’s coastal lifestyle.

4750 Dolphin Cay Lane S Unit 107, St Petersburg

12400 Park Boulevard Unit 419, Seminole
$178,000
2 Beds ⋅ 1 Baths ⋅ Seminole Hill Villas SubDv. ⋅ 33772 Zip Code
Charming, well-maintained 2-bedroom, 1-bathroom villa in the established 55+ community of Seminole Hill Villas. Enjoy the added peace of mind of a non-flood-zone location without giving up proximity to the coast, with the renowned Gulf beaches approximately two miles away. The Pinellas Trail, nearby parks, Seminole City Center, local dining, and entertainment are also within easy reach, placing both everyday conveniences and outdoor recreation close to home. Inside this lovely villa, an abundance of natural light pours into a welcoming and peaceful interior. The open floor plan flows seamlessly from the living room into the dining area and kitchen, where a sliding glass door opens to your private screened-in patio—an inviting space for morning coffee, entertaining guests, or unwinding in the Florida sunshine. The bonus room functions as a second bedroom, complete with a closet, electrical service, and an A/C vent. Improvements include luxury vinyl flooring (2023); quartz countertops, a subway tile backsplash, and fresh interior paint (2024); and decorative wood paneling and new patio pavers (2025). Along with these thoughtful improvements, the home features updated systems and appliances, including a newer water heater (2024), refrigerator (2025), and stackable washer and dryer (2025). Life at Seminole Hill Villas includes plenty of ways to relax, stay active, and connect with neighbors—from afternoons at the heated pool and games on the shuffleboard courts to time spent at the community clubhouse, fitness area, and library. Equally suited for year-round living or a seasonal retreat, this delightful villa offers a comfortable, low-maintenance home base for enjoying the best of Seminole and the Gulf Coast.

12400 Park Boulevard Unit 419, Seminole

6363 99th Way N Unit 12I, St Petersburg
$321,000
3 Beds ⋅ 2 Baths ⋅ Shores Of Long Bayou Condo SubDv. ⋅ 33708 Zip Code
From the moment you open the front door, your eye is immediately drawn to the beautiful lake view beyond the living room, setting the tone for relaxed Florida living. Lake views, a private oversized balcony, a private garage, and resort-style amenities make this spacious 3-bedroom, 2-bath second-floor condo in the gated and guarded Shores of Long Bayou a wonderful Seminole opportunity! Step inside to a comfortable, functional layout designed for easy Florida living. The kitchen offers ample cabinetry, plenty of workspace, and a convenient built-in pantry. The living room has large sliding glass doors that lead out to an impressive 6' x 19' private balcony overlooking one of the community’s beautiful lakes, creating an ideal space for morning coffee, outdoor dining, entertaining, or simply relaxing while enjoying the peaceful water views. Insulated, sun-blocking window treatments in the living room and sun-blocking screens on most of the condo’s windows and doors provide added comfort and help create a cooler, more comfortable interior. The spacious primary suite features an ensuite bath with dual sinks, walk-in shower, private water closet, and walk-in closet. The third bedroom, accented by elegant French doors, offers flexibility as a guest room, home office, den, or additional living space. A single-car garage located directly in front of the condo provides convenient parking and valuable additional storage. Enjoy easy access to one of two community pools, one located just a building away, as well as a clubhouse, ponds, lakes, and walking trail. This community offers a desirable combination of amenities, privacy, and convenience. The condo fee includes cable, internet, water, sewer, and trash, adding even more value. Schedule your showing today and start living the relaxed, resort-style waterfront experience you’ve been searching for!

6363 99th Way N Unit 12I, St Petersburg

1937 Blue River Road, Holiday
$550,000
4 Beds ⋅ 3 Baths ⋅ Key Vista Prcl 18 SubDv. ⋅ 34691 Zip Code
Welcome to 1937 Blue River Road, located in the highly sought-after Key Vista community in Holiday. This spacious 4-bedroom, 3-bath home with a 3-car garage also features a bonus room and additional flex space, offering plenty of room for a home office, gym, playroom, media room, or guest space. The large kitchen features a generous eat-in area and several newer updates, including the stove, dishwasher, and sink, along with updated sinks and fixtures throughout the home. The interior has also been freshly painted, giving the home a bright, refreshed feel. Major improvements include a 2023 roof and updated front and rear windows with hurricane protection for added peace of mind. The outdoor living space is one of the home’s best features. Situated on an extra-large conservation lot in a non-flood zone, the backyard offers a peaceful and private setting with tranquil views of the surrounding natural landscape. A spacious screened lanai provides the perfect place for morning coffee, outdoor dining, or relaxing in the shade, while the separate pergola area with paver decking creates an additional outdoor entertaining space. Whether hosting friends, grilling on the weekends, or simply enjoying the quiet conservation views, the backyard offers multiple areas to enjoy Florida living year-round. The landscape lighting adds ambiance in the evenings and highlights the outdoor space beautifully. Additional features include an EV charger, garage shelving, and the convenience of a 3-car garage with plenty of room for vehicles, storage, and hobbies. With its flexible floor plan, newer roof, expansive conservation lot, inviting outdoor living areas, and desirable Key Vista location, this home offers an exceptional combination of space, privacy, and Florida lifestyle living.

1937 Blue River Road, Holiday

1524 Lakeview Road Unit 304, Clearwater
$115,900
2 Beds ⋅ 2 Baths ⋅ Kalmia Condo SubDv. ⋅ 33756 Zip Code
Welcome to Kalmia Condos and easy Florida living in the heart of Clearwater! This spacious 2-bedroom, 2-bath condo offers an open and inviting floor plan with generous living spaces, plenty of natural light and excellent potential to make it your own. One of the biggest highlights is the BRAND-NEW HVAC SYSTEM installed September 2026, complete with a 10-year transferable warranty, a major upgrade offering comfort and peace of mind for years to come. The spacious kitchen provides plenty of room for cooking, storage and entertaining and flows easily into the large living and dining areas, creating a comfortable open-concept space for everyday living or hosting family and friends. The generously sized primary bedroom offers a walk-in closet and private en-suite bathroom, while the second bedroom and full guest bath provide flexibility for visitors, a home office or additional living space. HERE'S AN ADDED BONUS: The seller is offering a concession at closing toward updating the primary en-suite, giving the new owner an opportunity to personalize the space and select finishes that reflect their own style and taste! Located in the established 55+ Kalmia Condo community, residents enjoy beautifully maintained, park-like grounds and amenities that include a heated community pool, clubhouse, billiards/recreation areas and shuffleboard. It's an inviting setting for enjoying the Florida lifestyle without the maintenance of a single-family home. Centrally located in Clearwater with convenient access to shopping, restaurants, medical facilities, golf and some of the Gulf Coast's most beautiful beaches. Clearwater Beach, surrounding coastal communities and major roadways are all within easy reach. Whether you're looking for a full-time Florida residence or a seasonal retreat, this spacious condo offers a fantastic combination of location, community amenities, generous living space and a major NEW HVAC upgrade. Come see the possibilities and make 1524 Lakeview Rd #304 your own!

1524 Lakeview Road Unit 304, Clearwater

567 Deer Run N, Palm Harbor
$610,000
3 Beds ⋅ 2 Baths ⋅ Deer Run At Woodland Hills 2 SubDv. ⋅ 34684 Zip Code
Welcome to 567 Deer Run N, a 3-bedroom, 2-bath Palm Harbor retreat with a separate office/den, where the view beyond the lanai may be the first thing that stays with you. Set against a peaceful conservation area with no rear neighbors, the backyard feels wonderfully removed from the pace of everyday life. Deer often wander through, adding an unexpected touch of wild Florida to an already beautiful setting. Inside, the home has an easy elegance. A distinctive pass-through fireplace creates a warm focal point and connects the living spaces, while fresh paint and thoughtful touches throughout allow the home’s character to take center stage. The office/den adds valuable flexibility for working from home, hobbies, or an additional sitting space. The primary suite offers its own quiet escape, with a beautifully appointed bath featuring dual sinks, a soaking tub, and a walk-in shower. The screened pool and covered lanai become another room of the house, only here, the walls are open to the sky, the pool, and the conservation beyond. Imagine morning coffee as the neighborhood wakes, an afternoon spent poolside, or an evening that stretches well past sunset with friends gathered under the covered lanai. This is where the home begins to feel less like a property and more like a place you could see yourself staying. Community amenities add another dimension, with access to a community pool and pickleball/tennis courts. For the discerning buyer, the practical details have been thoughtfully addressed as well: 2020 roof, 2021 HVAC system, 2021 pool heater and variable-speed pool pump, 2025 pool pavers and pool tile, 2025 covered lanai with hurricane-rated materials, and newer carpet in the primary bedroom installed in 2026. Additional updates include fresh interior paint, iAquaLink Wi-Fi pool automation with convenient smartphone control, leaf-protection gutters, an irrigation system, landscape lighting, and a beautifully updated second bathroom. And then there is the location. Palm Harbor puts you close to some of the best of the Gulf Coast, with Honeymoon Island and Caladesi Island nearby, along with the beaches, parks, and trails that make this area such a special place to call home. Enjoy convenient access to shopping, dining, and entertainment at Countryside Mall, as well as the restaurants, shops, and waterfront charm of nearby Dunedin/Safety Harbor. Convenient access to US-19 and other major roadways also makes it easy to reach Clearwater, Tampa, area beaches, shopping, dining, and more. Some homes impress you with what they have. Others stay with you because of how they make you feel. 567 Deer Run N is one of those homes.

567 Deer Run N, Palm Harbor

18087 Ramble On Way, Land O' Lakes
$739,900
5 Beds ⋅ 3 Baths ⋅ Bexley South 4-4 & North 3-1 P SubDv. ⋅ 34638 Zip Code
TRULY MODEL-WORTHY IN BEXLEY WITH POND AND CONSERVATION VIEWS! Tucked toward the back of this highly desirable Land O’ Lakes community, this beautifully upgraded 5-bedroom, 3-bath home offers 3,336 square feet, a dedicated home office, oversized loft, 3-car tandem garage, and a move-in-ready interior where nearly every detail has already been thoughtfully finished. Step inside to stylish luxury vinyl plank flooring extending through nearly the entire home, complemented by plantation shutters throughout. Just off the entry, the dedicated home office has been transformed with custom built-in cabinetry and workspace, creating a polished and functional place to work from home. Continue into the main living area, where the upgrades take center stage. The kitchen features stylish cabinetry, stone countertops, additional cabinetry, upgraded hardware and lighting, stainless steel appliances, a gas cooktop, an updated and extended backsplash, and a brick accent wall that adds warmth and character. The kitchen opens to the dining area and spacious living room, creating an open-concept layout designed for everyday living and entertaining. Custom living room built-ins, shiplap accents, designer finishes, and abundant natural light give the space the feel of a professionally designed model home. Large sliding glass doors extend the living area outside to an expanded screened lanai with added pavers, an extended screen enclosure, and a picture-frame screen designed to maximize the peaceful pond and conservation views. The fenced backyard adds function and privacy, while the scenic backdrop creates a beautiful setting for relaxing and entertaining. Also located on the first floor is a private guest bedroom with a nearby full bathroom and direct access to the lanai, providing a flexible setup for overnight guests and convenient outdoor access. Upstairs, an oversized loft creates an impressive second living space with room for a media area, game room, home gym, or combination of uses. Three additional secondary bedrooms provide plenty of flexibility, including two tucked together near a shared full bathroom. The spacious primary suite feels like its own retreat, complete with a separate sitting area positioned to take advantage of the beautiful pond and conservation views. The en-suite bathroom features dual sinks, a frameless glass shower, and a large walk-in closet. An upstairs laundry room located just outside the primary suite adds everyday convenience. Located in the popular master-planned community of Bexley in Land O’ Lakes, residents enjoy miles of trails, resort-style pools, a fitness center, parks and playgrounds, a dog park, and the on-site Twisted Sprocket Café, along with convenient access to the Suncoast Parkway, shopping, dining, and the greater Tampa Bay area. This is a rare opportunity to own a beautifully finished, move-in-ready Bexley home where the interior, floor plan, and setting are equally impressive.

18087 Ramble On Way, Land O' Lakes

6244 Spoonbill Drive, New Port Richey
$725,000
5 Beds ⋅ 4 Baths ⋅ Gulf Harbors Sea Forest SubDv. ⋅ 34652 Zip Code
WATERFRONT OPPORTUNITY WITH 3,500+ SF, 2 PRIMARY SUITES, HEATED POOL & GULF ACCESS! BOAT OWNER? THIS IS YOUR CHANCE TO ACTUALLY USE THAT BOAT! MOTIVATED SELLER! Welcome to 6244 Spoonbill Drive—a NEVER-FLOODED, elevated waterfront home with 50FT seawall of water frontage! This is an incredible combination of space, flexibility, and Florida lifestyle. Situated on a coveted cul-de-sac/corner-edge lot with canal access toward the Gulf of Mexico, this property gives you the rare opportunity to have the boat, pool, entertaining space, and room for everyone—all in one place. With 5 bedrooms, 4 baths, 3,500+ SF, TWO PRIMARY SUITES, multiple living areas, and an exceptionally versatile floor plan, this home is perfectly suited for multigenerational living. The entire first floor creates an incredible IN-LAW SUITE/guest suite opportunity, complete with its own entrance, living spaces, bedroom, full bath, and direct access to the pool. Use it as a private retreat, guest quarters, media area, or extended-family living space—the flexibility is exceptional. The downstairs den also features a true wood-burning fireplace, adding warmth and character rarely found in today's homes. Upstairs, the main living level welcomes you with abundant natural light, an expansive great room, beautiful water views, and a spacious kitchen featuring custom cabinetry, extensive drawers and storage, stainless steel appliances, granite countertops, and an oversized island built for gathering. The primary suite overlooks the water and offers a generous bathroom, large walk-in closet, and crown molding, while the second primary suite downstairs provides its own private retreat. Crown molding continues through the common areas, adding an elegant finishing detail throughout the home. Storage is abundant, with oversized closets, linen closets, huge garage, cabinetry, and flexible spaces throughout. Step outside and the lifestyle gets even better. The backyard features a heated pool, multiple entertaining areas, gazebo/ pergola, outdoor dining, fire pit, fenced side yard, seawall, and floating dock—ready for pool parties, BBQs, music, sunset cocktails, and unforgettable gatherings. Take the boat out through the canal toward the Gulf, launch your kayak or paddleboard, or simply enjoy the dolphins, manatees, birds, and sunsets from your own backyard. This is the Florida dream—with the space to actually live it. The home has been exceptionally cared for and features a 2017 roof, 2022 AC, newer water heater, updated flooring throughout both levels, full paver driveway and sidewalk, professionally maintained AC, extensive storage, oversized closets, and a large custom kitchen. The bones are fantastic, the floor plan is incredibly versatile, and the cosmetic details offer an opportunity to personalize the home and create something truly special. Select virtually renovated bathroom images are included to help buyers envision the possibilities; no structural changes are represented. Gulf Harbors residents can enjoy the community clubhouse, pool, pickleball/tennis amenities and the option to join the private Gulf Harbors Beach Club. MOTIVATED SELLER + A HOME WITH THIS MUCH SPACE, WATERFRONT, POOL, BOATING ACCESS, AND MULTIGENERATIONAL POTENTIAL = A RARE OPPORTUNITY, ESPECIALLY IN THIS COMMUNITY AND PRICE POINT. Bring your vision, bring your boat, and make this Gulf Coast retreat your own!

6244 Spoonbill Drive, New Port Richey

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