Rotonda West Oakland Hill Homes with Pool

Rotonda West Oakland Hill Homes with Pool

Welcome to Rotonda West Oakland Hill, a serene and picturesque subdivision nestled in the heart of Rotonda West, Florida. This charming community is part of Charlotte County, where the natural beauty of the Sunshine State meets the tranquility of suburban living. With its lush landscapes and friendly atmosphere, Rotonda West Oakland Hill is the perfect place to call home.

One of the standout features of this subdivision is the abundance of homes with pools, offering a refreshing oasis right in your backyard. Imagine stepping out of your beautifully designed home to dive into your private pool on a warm Florida day, soaking up the sun or hosting delightful gatherings with family and friends. The homes in this area are thoughtfully designed, featuring modern amenities and spacious layouts that cater to the needs of families and individuals alike.

The community is surrounded by stunning golf courses, nature trails, and scenic parks, making it an ideal spot for outdoor enthusiasts. Whether you enjoy golfing, biking, or simply taking leisurely strolls, Rotonda West Oakland Hill provides endless opportunities for recreation and relaxation. Plus, with its proximity to pristine beaches and vibrant local attractions, you’ll never be far from the best that Florida has to offer.

Experience the charm of Rotonda West Oakland Hill, where beautiful homes with pools await you. Embrace a lifestyle of comfort, community, and sunshine in this idyllic subdivision. Your dream home is just a visit away!

Newest Rotonda West Oakland Hill Homes with Pool

$285,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Short Sale. Welcome to 50 Caddy Road in the desirable Oakland Hills section of Rotonda West! This beautifully maintained 3-bedroom, 2-bath pool home offers the perfect blend of comfort, style, and Florida living. Situated on the golf course with tranquil water views, the property features an expansive screened lanai, heated saltwater pool and spa, and a spacious split-bedroom floor plan designed for both relaxation and entertaining. The updated kitchen boasts stainless steel appliances, an island, and ample cabinetry, while multiple sliding glass doors seamlessly connect indoor and outdoor living spaces. A circular driveway, oversized side-entry garage, and mature landscaping enhance the home's curb appeal. Located near championship golf courses, beaches, boating, fishing, dining, and shopping, this home offers an exceptional opportunity to enjoy the Southwest Florida lifestyle.

50 Caddy Road, Rotonda West
$400,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Move-In Ready GOLF COURSE POOL HOME with NO REAR NEIGHBORS! Welcome to this beautifully maintained 3-bedroom, 2-bath ranch home overlooking the golf course in the heart of Rotonda West, one of Southwest Florida's premier golf communities featuring five championship courses with 99 holes of golf. Step inside to a bright, open floor plan where natural light fills the spacious living and dining areas. The kitchen is designed for both everyday living and entertaining, featuring granite countertops, stainless steel appliances, warm wood cabinetry, and generous counter space. Enjoy tile flooring throughout the main living areas and plank flooring in all three bedrooms. Offered completely furnished and turnkey, this home is ready for immediate enjoyment as a primary residence, seasonal getaway, or investment property. The spacious primary suite offers ample closet space and a private en-suite bath with a walk-in tiled shower and single vanity. Two additional generously sized bedrooms share a convenient guest bath with direct access to the pool. The true highlight is the outdoor living space. Relax in your heated, screened-in pool beneath a full cage enclosure while enjoying peaceful golf course views with no rear neighbors. Whether you're sipping your morning coffee, entertaining friends, or unwinding after a day at the beach, this private backyard setting captures the best of the Florida lifestyle. Additional features include a 2023 roof, 2025 pool pump, an attached garage, and a circular driveway providing plenty of parking. With HOA fees of just $190 annually, residents enjoy exceptional value in a community offering a clubhouse, restaurant, playground, walking and biking paths, scenic canals, and access to a local marina. Outdoor enthusiasts will appreciate being just 2.5 miles from Don Pedro Island State Park, with the beautiful beaches of Boca Grande and Englewood (Manasota Key) only minutes away. Conveniently located between Sarasota, Punta Gorda, Fort Myers, and Naples, you'll enjoy easy access to airports, shopping, dining, boating, fishing, and everything Southwest Florida has. Whether you're looking for a full-time residence, winter retreat, or income-producing investment, this move-in-ready golf course pool home offers the perfect combination of comfort, location, and Florida lifestyle.

82 Rotonda Circle, Rotonda West
$539,900
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Welcome To your Golf Course Facing Dream Home with an Oversized Pool. This 4 Bedroom 2 Bath Rotonda West Home is Perfect for any Golf enthusiast. The home is located on a nice quiet street with amazing views. This is one you truly must see to appreciate. The home does have a stage 2/ 240 Volt Auto Charger in the garage..

240 Caddy Road, Rotonda West
$599,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Discover modern Florida waterfront living at its finest in this stunning brand-new 2026-built 4-bedroom, 2-bathroom pool home with 2-car garage, perfectly situated on a freshwater canal in the desirable Oakland Hills section of Rotonda West! Boasting 1,862 sq ft of thoughtfully designed living space on a generous 10,000 sq ft lot with 80 feet of direct canal frontage, this turnkey new-construction residence offers exceptional quality, contemporary elegance and seamless indoor-outdoor living. Step inside to an open-concept layout with porcelain tile flooring throughout, soaring tray ceilings, and abundant natural light. The gourmet kitchen shines with quartz countertops, a large island, stainless steel appliances, and soft-close solid wood cabinetry—ideal for effortless entertaining. A split-bedroom floor plan ensures privacy, while dramatic corner slide-away glass doors connect the main living areas directly to the expansive screened pool and large covered lanai, creating the perfect setting for year-round outdoor enjoyment with serene canal views. Additional highlights include ceiling fans, central air conditioning and heating, inside laundry room, and a 2-car attached garage. Outside, relax by your private screened in-ground pool or entertain on the spacious lanai overlooking the water. Community boat docks and ramp are less than half a mile away, giving easy access to Rotonda West’s vast navigable canal network for fishing, kayaking, or boating adventures. Rotonda West delivers an unparalleled Southwest Florida lifestyle with low HOA fees of just $16/month, multiple golf courses (including nearby The Hills Golf Course), parks, bike trails, pickleball and tennis courts, and a true sense of community. Enjoy convenient access to world-class Gulf beaches, shopping, dining, and top-rated schools (Vineland Elementary, L.A. Ainger Middle, Lemon Bay High). Don’t miss your chance to own a brand-new canal-front pool home in one of Charlotte County’s most sought-after established communities. Schedule your private showing today and experience everything this exceptional property has to offer!

55 Rotonda Circle, Rotonda West
$305,700
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Sold TURNKEY, or blank slate for your personalization. WATERFRONT and Well BELOW MARKET VALUE!!! Welcome to this spacious 4-bedroom pool home located in the active golf course community of Rotonda West. Enjoy the best of Southwest Florida living in this tastefully curated home that comes ready for immediate income production, full time enjoyment, or a perfect seasonal retreat. Whether you're golfing at one of the 5 community courses or spending the day at the beautiful nearby parks or Gulf beaches, you will find a dreamy Florida day at your doorstep. Relax or entertain on the expansive, pool deck overlooking a serene freshwater canal. The pool is heated for year-round usage and enjoyment. The rear yard is fenced and ready for your furry guests. A thoughtfully designed split floor plan of 2/2 bedrooms offers generous living space and privacy. The fully furnished set up for the comfortable occupancy of up to 10 occupants. Guests will love the private pool bedroom with sliding glass doors leading directly to the pool deck lounge area. This pool bedroom offers stunning water views and a true retreat-like feel. Recent updates provide peace of mind, including a 2020 HVAC system, 2021 roof, 2022 electrical panel, Fiberglass Pool, 2024 Pool Heater and 2025 Pool Motor. The Rotonda West community also features a private storage area for RVs, boats, and other recreational vehicles. Community is very scenic known for its quiet streets, multiple golf courses, parks, walking trails, and family-friendly amenities including playgrounds, bike paths, and nearby tennis and recreational facilities—making it a great fit for both relaxation and active lifestyles. Opportunity awaits, in this proven income producing home so don't hesitate.

231 Caddy Road, Rotonda West
$278,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Welcome to 295 Annapolis Lane in beautiful Rotonda West, Florida, where comfort, privacy, and Florida living come together. This charming home offers two spacious bedrooms, two bathrooms, and a versatile den that can easily serve as a third bedroom, home office, or guest space. From the moment you arrive, you'll appreciate the peaceful setting and the inviting atmosphere that makes this property feel like home. Step outside to your private screened lanai and enjoy the heated swimming pool year-round, whether you're relaxing with your morning coffee or entertaining family and friends. The home has been thoughtfully maintained and benefits from several major recent improvements, including a new roof (2022), new air conditioning system (2022), new electrical panel (2024), and a new pool heater (2024), providing peace of mind for years to come. Inside, you'll notice a professionally installed European stretch ceiling, a premium architectural finish widely used throughout Europe for its sleek, seamless appearance, durability, and moisture-resistant qualities. It is a modern decorative feature that complements the home's clean and inviting interior. Ideally located just minutes from golf courses, marinas, Boca Grande beaches, shopping, dining, and all that Southwest Florida has to offer, this home is equally suited as a full-time residence, a seasonal retreat, or an income-producing investment. Whether you're searching for your own piece of paradise or your next smart investment, 295 Annapolis Lane is ready to welcome you.

295 Annapolis Lane, Rotonda West
$264,900
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Nicely updated 3 Bedroom Home with pool, A. C. Kitchen with wood cabinets, Granite counters and Stainless Steel Appliances. Large Rooms with Living Room and Family Room. Very good condition inside and out! Large pool and located on the Greenbelt. Just a short drive to Englewood Beaches! One block away from the Golf Club House of Rotonda West. Located on a quiet street. 10 minutes to the beach. 5 minutes to Walmart. The house has all new plumbing done in 2023. No hurricane damage. Furniture can be included in the sale of the home.

4 Golfview Road, Rotonda West
$375,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
This 2020 NEW BUILT stylish and move-in ready three-bedroom, two-bath home with a heated saltwater pool is located in the sought-after community of Rotonda West. Offering a bright, open layout, the home features soaring ceilings, luxury vinyl plank flooring throughout, recessed lighting, and a beautifully designed kitchen with granite counters, upgraded cabinetry, stainless steel appliances, and an oversized breakfast bar. There’s plenty of room to cook and entertain in the spacious kitchen, or you can enjoy more formal meals in the separate dining area. The primary suite includes two walk-in closets, a roomy Roman-style shower, and a dual-sink vanity topped with granite. Two guest bedrooms sit on the opposite side of the home, along with a full bathroom featuring a tub/shower combination. Additional perks include PUBLIC water and sewer, and furnishings can be purchased separately if desired. Situated just a short drive from beaches, golf courses, dining options, and shopping. Don’t miss your chance—schedule a tour today!

241 Annapolis Lane, Rotonda West
$249,900
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Peaceful pool home with preserve view! Nestled in a serene setting, this delightful 2-bedroom, 2-bathroom home offers the best of Florida living with lush preserve views and a tranquil backdrop. Located in desirable Rotonda West, this single-family gem includes a spacious open floor plan, a one-car garage, and a private pool—perfect for relaxation or entertaining. As you step inside, you're greeted by an airy living space with abundant natural light that highlights the beautiful tile flooring. The fully equipped kitchen, with plenty of counter space and storage, opens to the dining and living areas, making it ideal for both everyday living and gatherings. The open layout offers privacy, with the spacious primary suite featuring an en-suite bath and large closet, while the second bedroom is perfect for guests or a home office. The screened-in lanai invites you to enjoy Florida’s year-round sunshine, complete with a sparkling pool overlooking the pristine, protected preserve—a natural extension of your backyard that promises peace, quiet, and visits from local wildlife. Situated minutes from golfing, beautiful Gulf beaches, shopping, and dining, this home captures the relaxed Rotonda West lifestyle. Don’t miss this rare opportunity to own a private, peaceful pool home in a stunning location!

9 Annapolis Lane, Rotonda West
$262,000
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Great house in Rotonda West! Almost 1500 sqft of a full renovated 2 bed 2 bath house, with new roof! new kitchen, new floor, painted inside and outside. Beautiful pool in a huge screened lanai. Huge open floorplan. Close to beaches, shopping, restaurant. Ready to move in!

75 Annapolis Lane, Rotonda West
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