Rotonda West Oakland Hill Homes for Sale

Rotonda West Oakland Hill Homes for Sale

Welcome to Rotonda West Oakland Hill, a hidden gem nestled in the heart of Charlotte County, Florida. This charming subdivision offers a unique blend of serene living and vibrant community life, making it the perfect destination for families, retirees, and anyone seeking a peaceful retreat. With its picturesque landscapes and abundant natural beauty, Rotonda West is a haven for outdoor enthusiasts, featuring an array of parks, golf courses, and scenic trails that invite you to explore the great Florida outdoors.

As you navigate through the winding streets of Oakland Hill, you’ll discover a variety of homes for sale that cater to diverse tastes and lifestyles. From cozy single-family homes to spacious custom builds, each property reflects the unique character of the community. Many homes boast stunning views of the lush greenery and sparkling lakes that define this area, creating a tranquil backdrop for your everyday life.

The community is not only about beautiful homes; it also fosters a strong sense of belonging. Residents here enjoy a friendly atmosphere, with regular neighborhood events and activities that encourage connection and camaraderie. Whether you’re taking a leisurely stroll along the well-maintained sidewalks or joining in on community gatherings, you’ll quickly feel at home in Rotonda West Oakland Hill.

With its prime location, stunning homes, and welcoming community spirit, Rotonda West Oakland Hill is more than just a subdivision; it’s a lifestyle waiting to be embraced. Discover your dream home today and experience the charm of Rotonda West for yourself!

Newest Rotonda West Oakland Hill Homes for Sale

$229,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Welcome to Rotonda West Oakland Hills, where this turnkey furnished 3 bedroom, 2 bath home sits on a quiet street with a tranquil nature preserve just beyond the backyard fence. Offering 1,743 square feet under air, a one car garage, and no rear neighbors, this is a smart opportunity for a primary residence, seasonal getaway, or investment property in one of Southwest Florida's most amenity-rich communities. Fresh interior paint, new entrance tile, a replaced front window, and an updated kitchen were all completed in 2025, and the home comes fully furnished and ready to enjoy from day one. The spacious living room is anchored by a wide bay window that fills the space with natural light, with laminate flooring running through the main living areas. The dining room flows into a generous family room lined with windows overlooking the green backyard. The kitchen connects it all with granite countertops, maple cabinetry, a subway tile backsplash with a glass mosaic accent, and a pass-through that keeps the cook part of the conversation. The oversized primary suite features a full wall of closets and a private bath with a tub and shower. Two additional guest bedrooms with built-in closets share a second full bath with a walk-in shower and its own door to the backyard, a convenient touch after a day outside. Sliding doors open to an expansive covered lanai, an easy spot for morning coffee or evening gatherings with preserve views as the backdrop. The fully fenced backyard offers two gated entrances, a paver patio, and a fire pit, with plenty of room for pets, play, or a future pool. Rotonda West is known for its golf courses, walking and biking trails, parks, and canals, all supported by an association fee of just $190 per year. Boca Grande and the beaches of Englewood are a short drive away, along with dining, shopping, and everyday conveniences. Come see the space, quiet, and easygoing Gulf Coast lifestyle this home delivers. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

113 Annapolis Lane, Rotonda West
$220,000
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Short Sale. SHORT SALE – Fantastic Opportunity to Own a Golf Course Home in Rotonda West! If you've been dreaming of affordable Florida golf course living, this is your chance! Perfectly situated overlooking the golf course, this inviting 2-bedroom, 2-bath, 2-car garage home offers peaceful fairway views from the screened lanai—Slider doors take you out to the screened in lanai. An ideal spot to enjoy your morning coffee while watching golfers, native birds, and Florida wildlife. Inside, you'll find tile flooring throughout, a newer roof, neutral colors, an open living and dining area, and an eat-in kitchen with a breakfast bar that's perfect for casual meals or entertaining. The spacious primary suite features a walk-in closet and private bath, while the guest bedroom is conveniently located near a dual-access guest bath, providing comfort and privacy for family and guests. Priced to give you the opportunity to make it your own, this home offers endless potential whether you're looking for a year-round residence, seasonal getaway, or investment opportunity in one of Southwest Florida's most desirable golf course communities. Conveniently located near the Rotonda West clubhouse, community center, dining, shopping, boating, world-class fishing, and the beautiful Gulf beaches of Boca Grande, you'll enjoy everything Southwest Florida has to offer. Don't miss this exceptional opportunity to own a golf course home at an incredible value. Short sale—lender approval required.

144 Rotonda Circle, Rotonda West
$289,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Welcome to this beautifully reimagined 3-bedroom, 2-bath home, where nearly every detail has been thoughtfully updated to provide a fresh, modern living experience. From the moment you step inside, you'll appreciate the bright, open feel created by the brand-new flooring, new drywall, and abundant natural light streaming through the new windows. The stunning kitchen serves as the heart of the home, featuring elegant solid stone countertops, new cabinetry, and modern finishes that blend style with functionality. Whether you're preparing everyday meals or entertaining family and friends, this space is designed to impress. The extensive renovation continues throughout the home with beautifully updated bathrooms, refreshed living spaces, and an updated A/C system for year-round comfort. A new roof installed in 2023 provides additional peace of mind, making this home truly move-in ready. Located in the highly desirable golf community of Rotonda West, residents enjoy multiple championship golf courses, scenic walking and biking trails, beautiful parks, and easy access to Boca Grande, Englewood Beach, Manasota Key, world-class fishing, boating, shopping, dining, and all that Southwest Florida has to offer. Every inch of this home reflects quality craftsmanship and attention to detail. The incredible professional photography tells the story even better, this is a home you simply have to experience in person. Don't miss this exceptional opportunity to own a fully renovated home in one of Florida's most sought-after communities.

30 Oakland Hills Court, Rotonda West
$285,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
If you're searching for a full-time residence, seasonal getaway, or investment opportunity, this move-in-ready home deserves a spot at the top of your list. Located in the highly desirable, deed-restricted golf community of Rotonda West, this lovingly maintained 3-bedroom, 2-bath home with a 1-car garage offers exceptional curb appeal with mature landscaping and a fenced backyard overlooking a peaceful preserve. Featuring 1,839 square feet of living space, this home provides plenty of room to spread out with both a formal living room and family room, as well as a dining room and a breakfast area adjacent to the beautifully updated kitchen. The kitchen features upgraded cabinetry, granite countertops, and ample workspace, making it ideal for everyday living and entertaining. The split-bedroom floor plan offers privacy for both owners and guests, with generously sized bedrooms and abundant closet space. Tile flooring throughout provides easy maintenance and complements a variety of decorating styles. Oversized covered and screened lanai with tile flooring. Privacy fenced backyard and tranquil preserve views. The home has been extensively updated with hurricane-impact windows, hurricane-impact sliding glass doors, hurricane shutters, and a hurricane-rated garage door. A spacious 9' x 14' storage room located at the rear of the garage, complete with double doors leading to the backyard, provides excellent storage for lawn equipment, tools, and recreational gear. Residents of Rotonda West enjoy access to a 165-acre community park, Rotonda W Community Center, multiple championship golf courses, walking and biking trails, tennis courts, and easy access to the area's pristine Gulf beaches, Intracoastal waterways, world-class fishing, shopping, dining, and entertainment. AC replaced 2023, new roof 2022, new water heater 2025. This meticulously maintained home is truly move-in ready. Schedule your private showing today and start enjoying the Florida lifestyle!

27 Annapolis Lane, Rotonda West
$239,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Welcome to Rotonda West, Florida, home to several of the area's finest golf courses and conveniently located just minutes from beautiful Gulf beaches, world-class fishing, shopping, dining, and more. This recently updated 3-bedroom home is sure to impress from the moment you arrive. An expansive, oversized breezeway leads to the front entrance, creating an inviting first impression. Inside, you'll find fresh interior paint, updated flooring, and a beautifully remodeled kitchen featuring shaker-style cabinetry, quartz countertops, and a stylish tile backsplash. The updates continue with both bathrooms, which have been tastefully renovated. In addition to the spacious front breezeway, the home offers an impressive 35-foot rear lanai, providing the perfect space for relaxing or entertaining. For added peace of mind, the roof was just replaced in July and includes a secondary water barrier for enhanced storm protection. Need more space? The lot next door is also available under seperate contract by a party related to the Seller.

267 Annapolis Lane, Rotonda West
$239,500
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
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. ⋅ 33947 Zip Code
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. ⋅ 33947 Zip Code
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. ⋅ 33947 Zip Code
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
$275,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
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. ⋅ 33947 Zip Code
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. ⋅ 33947 Zip Code
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
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