Rotonda West Oakland Hill Real Estate

Rotonda West Oakland Hill Real Estate

Welcome to Rotonda West Oakland Hill, a hidden gem nestled in the heart of sunny Florida! Located in Charlotte County, this picturesque subdivision is a part of the charming community of Rotonda West, known for its serene landscapes and friendly atmosphere. With its lush greenery, scenic lakes, and an abundance of wildlife, Oakland Hill offers a tranquil retreat for those seeking a peaceful lifestyle.

This vibrant community is designed for both relaxation and recreation, featuring an array of amenities that cater to residents of all ages. Enjoy leisurely strolls along the beautifully maintained walking paths or challenge your friends to a round of golf at one of the nearby courses, including the renowned Rotonda Golf & Country Club. For nature lovers, the area boasts stunning parks and preserves, perfect for hiking, biking, or simply soaking up the Florida sunshine.

Families will appreciate the close-knit community feel, with local events and activities that foster connections among neighbors. The subdivision is conveniently located near shopping centers, dining options, and top-rated schools, ensuring that everything you need is just a short drive away.

Whether you’re looking to build your dream home or find a serene getaway, Rotonda West Oakland Hill offers the perfect blend of tranquility and convenience. With its stunning natural beauty and welcoming community spirit, this subdivision is more than just a place to live; it’s a lifestyle waiting to be embraced. Come discover the charm of Rotonda West Oakland Hill, where your dream home awaits!

Newest Listings in Rotonda West Oakland Hill

$225,000
2 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
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
$425,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
FULLY RENTED WATERFRONT DUPLEX IN ROTONDA WEST! Add a turnkey income-producing property to your portfolio with this beautifully renovated duplex overlooking the water, park, marina, and golf club in one of Southwest Florida’s most desirable communities. Both units are currently rented, providing immediate rental income from day one! Each unit features 2 bedrooms, 1 bathroom, and a large private screened lanai designed to take full advantage of the peaceful waterfront setting and scenic views. Step outside and enjoy the private dock, perfect for fishing, relaxing by the water, or simply enjoying the Florida lifestyle. The property overlooks Oakland Hills Island and its charming gazebo, creating a picturesque backdrop rarely found in an investment property. Major improvements provide added peace of mind, including TWO BRAND-NEW A/C UNITS and 2023 ROOFS. The duplex has been extensively renovated with updated kitchens and bathrooms, newer cabinetry, modern ceiling fans, fresh interior and exterior paint, and updated appliances including washer/dryer combinations, ranges, refrigerators, microwaves, and disposals. The large screened lanais provide valuable additional outdoor living space for both units. A newly sealed asphalt parking area accommodates up to six vehicles, making the property convenient for tenants and guests. Located in the heart of Rotonda West, residents enjoy easy access to multiple golf courses, the nearby marina and community boat ramp, walking and biking trails, dining, RV and boat storage, and numerous recreational amenities. Boca Grande and Englewood beaches are approximately 8 miles away, placing world-class boating, fishing, beaches, and the Gulf Coast lifestyle within easy reach. With both units already occupied, substantial renovations completed, newer roofs, brand-new A/C systems, waterfront views, a dock, and desirable outdoor living spaces, this property offers an attractive combination of current income and long-term investment potential. A rare opportunity to own a fully rented waterfront duplex in beautiful Rotonda West!

108 Boundary Boulevard Unit B, Rotonda West
$314,900
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
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
$26,900
Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
AFFORDABLE RESIDENTIAL SINGLE-FAMILY LOT IN BEAUTIFUL ROTONDA WEST! Discover the opportunity to build your dream home in one of Southwest Florida's most desirable golf communities. This vacant residential lot is located in the popular Rotonda West Golf & Deed-Restricted Community and is ideally situated for enjoying the best of the Florida lifestyle. Public water and sewer are available on site, making this an excellent opportunity for building your new home. Per the Charlotte County website, no scrub jay habitat is identified on the property. Rotonda West offers an exceptional location with easy access to Gulf beaches, boating, fishing, golf, shopping, restaurants, and entertainment. Nearby Boca Grande is renowned for its beautiful beaches and world-class fishing, while Englewood and Port Charlotte provide additional shopping, dining, and everyday conveniences. Golf enthusiasts will appreciate the Rotonda Golf & Country Club, featuring five golf courses with a total of 99 holes, offering plenty of opportunities to enjoy a round of golf close to home. Rotonda West also offers approximately 26 miles of picturesque canals, ponds, and lakes, creating a beautiful natural setting with abundant fish and wildlife. Whether you're looking to build your primary residence, seasonal Florida getaway, or simply invest in land for the future, this affordable Rotonda West lot offers a great opportunity to own property in a desirable Southwest Florida community. Don't miss the opportunity to own a piece of paradise in SW Florida.

227 Annapolis Lane, Rotonda West
$219,000
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
$279,000
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
$25,000
Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Build your dream home on this exceptional vacant lot located in the desirable Oakland Hills section of Rotonda West, a beautifully maintained, deed-restricted golf community renowned for its lush landscaping, peaceful atmosphere, and exceptional quality of life. Surrounded by well-kept homes and scenic green spaces, this build-ready homesite offers the perfect setting to create your ideal Southwest Florida retreat. Golf enthusiasts will appreciate Rotonda West's five professionally designed golf courses featuring 99 championship holes, while nature lovers can enjoy the community's tranquil lakes, canals, and abundant wildlife. With city water and sewer already available, the building process is simple and convenient. Residents enjoy low HOA fees and the benefits of a meticulously maintained community that reflects pride of ownership throughout. Ideally situated just minutes from pristine Gulf Coast beaches, boating, fishing, shopping, dining, and endless outdoor recreation, this property offers the perfect balance of peaceful living and everyday convenience. Whether you're planning to build your forever home, a seasonal getaway, or invest in one of Southwest Florida's most sought-after communities, this Oakland Hills homesite presents an outstanding opportunity to enjoy the best of Florida's relaxed coastal lifestyle.

269 Annapolis Lane, Rotonda West
$227,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
NEW ROOF JULY OF 2026 add to the value of this recently updated 3-bedroom home which 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
$425,000
Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Exceptional development opportunity in the Oakland Hills subdivision of Rotonda West. This approximately 3.43-acre parcel offers nearly 149,500 square feet of land, substantial frontage along Golfview Road. The property is currently zoned RSF-5, Residential Single-Family, allowing up to five residential units per acre, subject to county requirements and development approvals. Seller-provided conceptual development plans illustrate the potential for a boutique residential community of approximately 12 to 17 single-family homes. Preliminary layouts include internal roadway access, cul-de-sac configurations, stormwater retention, and individual residential homesites. One concept depicts a 15-lot development surrounding a private roadway and retention pond, while an alternative “Version 2” layout depicts as many as 17 homesites. The parcel’s size, established residential surroundings, and proximity to Gulf beaches, golf courses, boating, shopping, and dining make this an intriguing opportunity for a builder, developer, or investor seeking a residential project in Southwest Florida. Conceptual plans are preliminary and are not represented as approved or currently permitted. The number of buildable homesites will depend upon Charlotte County approval, zoning and density requirements, roadway standards, utility availability, stormwater management, wetlands, flood-zone boundaries, environmental conditions, association requirements, and other applicable regulations. Buyers should conduct independent due diligence and verify all development potential with Charlotte County and the appropriate governing authorities.

3 Golfview Road, Rotonda West
$209,000
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
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