Rotonda West Oakland Hill Homes for Sale

Rotonda West Oakland Hill Homes for Sale

Welcome to Rotonda West, specifically the picturesque enclave of Oakland Hill, where your dream home awaits! Nestled in the heart of Charlotte County, Florida, this charming subdivision is renowned for its stunning natural beauty and vibrant community spirit. With its lush landscapes and serene surroundings, Oakland Hill is the perfect place to call home.

As you explore this delightful neighborhood, you’ll discover a variety of homes for sale, each offering unique features that cater to diverse lifestyles. From spacious single-family residences to cozy villas, there’s something for everyone in Oakland Hill. Many properties boast stunning views of the nearby lakes and golf courses, providing a tranquil backdrop for your daily life. The architectural styles range from contemporary designs to classic Floridian aesthetics, ensuring that you’ll find a home that resonates with your personal taste.

Living in Rotonda West means embracing an active lifestyle. The area is surrounded by pristine parks, scenic walking trails, and world-class golf courses, offering endless opportunities for outdoor recreation. Plus, with nearby beaches just a short drive away, you can easily indulge in sun-soaked days by the Gulf of Mexico.

The community is also known for its friendly atmosphere and welcoming neighbors, making it an ideal place for families and retirees alike. With a variety of local shops, restaurants, and amenities at your fingertips, everything you need is just around the corner.

Discover the charm of Oakland Hill in Rotonda West today, where your ideal home and vibrant community await! Explore our listings and take the first step toward your new life in sunny Florida.

Newest Rotonda West Oakland Hill Homes for Sale

$249,500
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Enjoy peaceful waterfront living at this beautifully updated canal-front home in Rotonda West. This move-in-ready 2-bedroom, 2-bath residence features tile flooring throughout, a remodeled kitchen with quartz countertops, updated bathrooms, new lighting, fixtures, and electrical receptacles. Both spacious bedrooms offer walk-in closets for plenty of storage. Relax and enjoy the tranquil canal views from your backyard while being just minutes from Gulf beaches, golf courses, boating, fishing, shopping, and dining. Whether you're looking for a full-time residence, seasonal retreat, or investment property, this home is ready to impress.

192 Annapolis Lane, Rotonda West
$279,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Welcome to Southwest Florida~UPDATED~ This Spacious~Turnkey~ home has been completely upgraded and ready for you to make fantastic memories with your loved ones. This 3 bedroom, 2 bath home located on a Golf Course in a quaint court. Sit outback, grill and watch the golf game or join in at one of the several courses located in Rotonda! An affordable flexible home owners association makes this property a perfect investment if you are not quite ready to retire. This home has a successful rental record. This COMPLETELY RENOVATED HOME is Beautiful and has a wide open Golf Course View. New Impact Windows for your protection, New Kitchen, New Baths, New Flooring, New Hot water Heater, Freshly Neutral colors throughout and the Exterior has just received a fresh coat of paint. Make this your choice to invest in our community. Rotonda West has a Rich History all the way back with Ed Mcmhon~He helped put ROTONA WEST ON THE MAP. This community has Parks, to Play, Sidewalks to bike and long walks~ while enjoying our Sunshine. This property is minutes from local restaurants, beaches, shopping, fishing and several golf courses. Like Baseball? Watch the Rays or the Braves locally!

18 Golfview Court, Rotonda West
$219,000
2 Beds ⋅ 1 Baths ⋅ Rotonda West Oakland Hill SubDv.
Full of charm and character in the Oakland Hills section of Rotonda West, this 2 bedroom, 1 bathroom home combines colorful coastal style with valuable updates including a 2023 roof, impact windows, and an impact garage door. Backing to a greenbelt with no homes directly behind, the property enjoys added privacy and peaceful natural views. A screened front porch and entry create a welcoming first impression, complemented by distinctive rock landscape beds, an expanded driveway with additional parking, and a single car garage. Inside, the open floor plan features both a formal living room and a large family room offering plenty of space for everyday living and entertaining. The family room features crown molding, beadboard accents, built-in cabinetry with a dry bar, and French door access to the covered screened lanai, while luxury vinyl plank and tile flooring, along with plantation shutters throughout, create a bright and inviting atmosphere. The kitchen offers a tray ceiling with recessed lighting, laminate cabinetry and countertops, tile backsplash, white appliances, and a movable island that provides additional workspace or serving space when entertaining. The primary bedroom includes a walk-in closet, while a large walk-in hallway storage closet provides additional storage. The guest bedroom features a reach-in closet and the bathroom has a step-in tiled shower. The covered screened lanai overlooks the Charlotte County preserve, where the peaceful natural setting attracts a variety of native birds and Florida wildlife, while the fenced backyard provides additional space for pets, gardening, or simply enjoying the outdoors. Additional updates include a 2022 A/C, newer interior and exterior paint, 2025 kitchen appliances, newer washer and dryer, and custom plantation shutters throughout. Located in deed restricted Rotonda West, residents enjoy five championship golf courses, miles of walking and biking trails, parks, 26 miles of canals and lakes, and abundant natural areas perfect for fishing, kayaking, and observing wildlife. Nearby marinas provide easy access to boating on Lemon Bay and the Gulf, while Englewood Beach and Boca Grande are just a short drive away for white sand beaches, waterfront dining, shopping, fishing, and spectacular Florida sunsets. Whether you're looking for a full-time home, seasonal retreat, or investment opportunity, 23 Annapolis Lane is ready for its next owner to enjoy everything Rotonda West has to offer.

23 Annapolis Lane, Rotonda West
$451,100
4 Beds ⋅ 3 Baths ⋅ Rotonda West Oakland Hill SubDv.
Under Construction. Step into luxury with this brand-new 4-bedroom, 3-bath, 3-car garage home with the CR elevation, designed with an exceptional open layout and an expansive extended lanai—perfect for relaxing or entertaining. Premium Features Throughout -Tile flooring Whole House, Lavish master bath with a 5-foot tiled shower & tiled floor, elegant Granite countertops in kitchen & bathrooms, upgraded cabinetry for a sleek, modern feel, High-end stainless-steel appliances (dishwasher, stove, microwave), Step ceiling in bedroom for added elegance. Beautiful exterior French glass doors leading to the covered lanai. Irrigation system with Bahai sod. Always ask about flex cash because it does change often. Adams Homes pays the majority of closing costs when using a preferred lender—making homeownership easier than ever! Prices are subject to change. All details are subject to errors & omissions.

18 Caddy Road, Rotonda West
$349,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
What a find! A beautifully remodeled 3 bed, 2 bath home with a living room, family room, dining area in kitchen and a bonus room/den!! The master bedroom has sliders into the bonus room/den and a large walk in closet. Outside you have a deck off the family room. The canal even has fish! The roof was replaced in 2022. There is an affordable HOA fee ($190/year) and an RV/Boat parking lot for an additional fee. The Hills restaurant and Lipinski's Tavern are located in Rotonda West, along with American Legion post 113. Furnishings can convey with a reasonable accepted offer. From AI: Rotonda West is a master-planned, deed-restricted golf community located on the Cape Haze Peninsula. Famous for its circular design, it features 26 miles of canals, multiple golf courses, and is located just 15–20 minutes from the pristine Gulf beaches of Manasota Key and Boca Grande. Outdoor & Golf Lifestyle: The community is centered around an active, outdoor lifestyle. Rotonda contains six golf courses within its boundaries and boasts 30-plus miles of freshwater canals great for fishing, kayaking, and viewing local wildlife.

199 Caddy Road, Rotonda West
$300,000
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
$315,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
JUST RENOVATED & SHOWS LIKE NEW! Welcome to your waterfront paradise in Rotonda West! This spectacular 4-bed, 2-bath home plus den sits right on a peaceful canal and radiates a fun, modern beach vibe. What’s New? Everything! • Brand-new impact windows & doors for total peace of mind • Chef's kitchen with quartzite counters & soft-close cabinets • Luxury vinyl flooring & fresh paint inside and out • Huge, screened lanai with custom epoxy floors Perfect as a forever home, a vacation getaway, or a lucrative rental investment. This Florida gem is ready for you to move right in and start enjoying the paradise lifestyle!! ASSUMABLE FLOOD INSURANCE AT A GREAT RATE. CALL TODAY to schedule your showing!!!

219 Caddy Road, Rotonda West
$350,000
4 Beds ⋅ 3 Baths ⋅ Rotonda West Oakland Hill SubDv.
Discover **Paradise on a dime** in this fully remodeled **three level home** featuring **3 bedrooms plus a bonus room that can easily convert back into a **4th bedroom**. The property offers **3 full bathrooms”, a **large, updated kitchen**, and an impressive list of recent upgrades including a **new roof**, **impact windows and sliding glass doors**, **new appliances**, **new kitchen cabinets**, **all new flooring throughout**, and a two car garage. Rotonda West is just minutes away from the beautiful beaches of Gasparilla and Boca Grande Islands. Not only does the property have views of five different fairways, but Rotonda West includes five championship golf courses inside your neighborhood.

90 Oakland Hills Court, Rotonda West
$339,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Welcome to 249 Rotonda Blvd W, a beautifully maintained 2021-built home located in the desirable Oakland Hills section of Rotonda West. This spacious 4-bedroom, 2-bath home offers 1,755 square feet of comfortable living space, a 3-car garage, and an oversized 0.37-acre lot. Step inside to an open and inviting floor plan featuring cathedral ceilings, tray ceiling accents, stone countertops, upgraded cabinetry, and a kitchen/family room combination designed for everyday living and entertaining. The main living areas feature tile flooring, while the bedrooms offer a comfortable private retreat. The primary suite includes a walk-in closet and a well-appointed bathroom with a tiled shower and dual-sink layout. Enjoy Florida living from the covered rear lanai overlooking the spacious backyard, with plenty of room to relax, garden, entertain, or explore future outdoor possibilities. Additional features include hurricane shutters, an irrigation system, public water and sewer, and low annual HOA fees. Rotonda West offers a peaceful residential setting near golf courses, parks, boating, fishing, Gulf beaches, shopping, restaurants, and everything Southwest Florida living has to offer. Furniture is available to stay, making this home an attractive option for buyers looking for a move-in-ready opportunity. Schedule your private showing today and see why this Rotonda West home is a strong value in today’s market.

249 Rotonda Boulevard W, Rotonda West
$249,500
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Live your best life at this WATERFRONT home in the highly sought after ROTONDA WEST community! This 2-BEDROOM, 2 BATH home is a true hidden gem, nestled along the tranquil canals in Rotonda West! Enjoy 5 GOLF COURSES, BROADMOOR PARK, tons of walking trails & 26 miles of picturesque canals! This is the place to be with many lakes, ponds and lots of wildlife! Just a short drive south to world class BOATING & FISHING in Boca Grande & Englewood! 9.1 miles to MANASOTA BEACHES! This waterfront home includes a NEW ROOF installed in 2021 & HURRICANE IMPACT RATED WINDOWS ensuring peace of mind for years to come! A covered screened patio entrance with a frosted glass door leads into a charming open floor plan with MANY UPDATES THROUGHOUT! Living/Dining combo with tile flooring creates a bright & airy coastal living space! Sliding doors lead to a screened patio (21 x 10) with beautiful views of the waterfront canal! You'll love the UPGRADED KITCHEN, featuring STAINLESS-STEEL APPLIANCES, shaker style cabinets & the DYNAMITE countertops & backsplash! Two comfortably sized bedrooms with the primary bedroom featuring a nice WALK-IN CLOSET. The primary bathroom includes a single cabinet vanity & WALK-IN SHOWER. The attached 2-CAR GARAGE offers ample storage space including built-in shelving & a second bathroom with shower! The spacious backyard would be a great spot for adding your own private pool or you could even add a dock to park a pontoon boat for cruising the canals! Enjoy a variety of fabulous & unique restaurants & great SHOPPING along Route 776! This is the perfect route to find all the desirable destinations along the Gulf! Enjoy soaking up the sun on the gulf shores of Manasota Beach known for shelling & shark teeth hunting! If you love Major League Baseball attending a spring training game is always a great time just 30 minutes away! Live your best life at Florida's hidden gem on the Southwest Gulf Coast~ Rotonda West! Call now to schedule your private tour today!

52 Annapolis Lane, 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
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