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

2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

Virtually Staged. BEAUTIFULLY RENOVATED and MOVE-IN READY! Enjoy a fantastic GOLF COURSE VIEW from this spacious 2-bedroom, 2-bath home in desirable Rotonda West. This home features a full 2-car garage, tile flooring, and a bright, comfortable floor plan offering both a living room and a separate family/Florida room perfect for relaxing or entertaining. The newly renovated interior is complemented by ALL NEW APPLIANCES, giving the home a fresh, updated feel throughout. Step outside and enjoy the peaceful golf course setting and beautiful views. Whether you're looking for a full-time Florida residence, seasonal getaway, or investment property, this home offers a great combination of location, updates, space, and Florida lifestyle!

66 Oakland Hills Court, Rotonda West

3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

Welcome to your effortless Florida getaway or lucrative investment opportunity! This beautifully updated 3-bedroom, 2-bathroom, 2-car garage home in Rotonda West’s desired Oakland Hills subdivision comes fully turn-key furnished—down to the dishes, linens, and silverware—so you can simply unpack your bags or start generating rental income from day one. Peace of mind comes built-in with major capital improvements, including a newer roof (2022), A/C (2018), new exterior fascia, brand-new gutters, and public water and sewer utilities. Inside, the remodeled chef's kitchen serves as the heart of the home, featuring a new center island, stunning new granite countertops with a matching backsplash, a new stainless steel sink and faucet, and sleek newer appliances. Freshly painted inside and out, the home shines with gorgeous waterproof laminate flooring throughout the main living areas, plush new carpet in all three bedrooms, and remote-controlled ceiling fans paired with updated light fixtures in every room. Boasting over 2000 square feet of bright, open-concept living space, the intuitive floor plan flows seamlessly between the formal living and dining areas into a sprawling 11x28 sunlit family room. The oversized 12x17 primary suite serves as a true retreat, complete with a large walk-in closet, a private bathroom with a walk-in shower, and a dedicated 11x19 adjoining den/office—perfect for remote work, hobbies, or a quiet reading nook. Step outside to enjoy serene waterfront living right in your own backyard along the crystal-blue freshwater canal, with peaceful neighborhood views framing the front. Nestled in a pristine, highly sought-after community with exceptionally low HOA fees of just $190 per year, you are only minutes away from five championship golf courses, local dining, shopping, and the world-class sandy beaches of Boca Grande and Englewood. Whether you are searching for your family's year-round dream home, a seasonal retreat, or a high-performing turn-key investment, this property delivers it all. Schedule your private tour today!

199 Caddy Road, Rotonda West

3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

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

3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

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

3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

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

3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.

NEW ROOF JULY OF 2026 add to the value of 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

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

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

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

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

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

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

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