Rotonda West Oakland Hill Homes with Florida Architectural style

Rotonda West Oakland Hill Homes with Florida Architectural style

Welcome to Rotonda West Oakland Hill, a picturesque subdivision nestled in the heart of sunny Florida, specifically within the charming city of Rotonda West in Charlotte County. This vibrant community is renowned for its stunning natural beauty, featuring lush landscapes, serene waterways, and an abundance of outdoor recreational opportunities.

Rotonda West Oakland Hill boasts a collection of homes that exemplify the classic Florida architectural style, characterized by open floor plans, expansive windows, and inviting outdoor spaces that seamlessly blend indoor and outdoor living. These homes are designed to take full advantage of Florida’s year-round sunshine, with features such as spacious lanais and private pools perfect for entertaining or simply enjoying the tranquil surroundings.

Residents of this delightful subdivision enjoy access to a variety of amenities, including golf courses, parks, and walking trails, making it an ideal location for those who appreciate an active lifestyle. The community is also conveniently located near beautiful beaches, shopping centers, and dining options, ensuring that everything you need is just a short drive away.

Whether you are looking for a permanent residence or a seasonal retreat, Rotonda West Oakland Hill offers a perfect blend of comfort, elegance, and Florida charm. With its welcoming atmosphere and stunning homes, it’s no wonder that this subdivision is a sought-after destination for homebuyers looking to embrace the Florida lifestyle. Come and discover the beauty of Rotonda West Oakland Hill – your dream home awaits!

Newest Rotonda West Oakland Hill Homes with Florida Architectural style

90 Oakland Hills Court, Rotonda West
$339,000
4 Beds ⋅ 3 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
Space to Live. Room to Relax. A Florida Lifestyle Ready to Enjoy. Welcome to 90 Oakland Hills Court, where the hard work is already done, and the laid-back Florida lifestyle is waiting. With an impressive 2,305 square feet under air, 4 bedrooms, 3 full baths, and a two-car garage, this beautifully updated Rotonda West home combines generous living space with a golf-course setting that's hard to duplicate. Tucked away at the end of a quiet cul-de-sac, the property offers an extraordinary 270-degree golf-course frontage and view overlooking the Women’s 4th Tee of the Oakland Hills Golf Course. Mature landscaping frames the home and creates a beautiful backyard oasis where mornings can begin with coffee overlooking the greens and afternoons can be spent relaxing in the Florida sunshine as golfers make their way around the course. Step inside and you’ll immediately appreciate just how much space this home offers. The updated kitchen is fresh, light, bright, and inviting, with Shaker-style cabinetry, stainless steel appliances, a convenient center island, and updated flooring, making it equally suited for a quiet breakfast or a house full of family and friends. The spacious primary suite offers a private retreat, complete with a beautifully renovated ensuite bath featuring a freestanding soaking tub, dual sinks, and a separate walk-in shower. And then there’s the lower level—a convenient 'flex' space, currently in use as a fourth bedroom, that lets this home live even larger. Two sets of impact-resistant sliding glass doors open directly to the large backyard patio, while a renovated full bathroom makes the space exceptionally versatile. Create a private guest or mother-in-law suite, family room, home theater, billiards or game room, gym, home office, fourth bedroom—or combine several into one fabulous multifunctional living space. Whether you need room for visiting family, working from home, entertaining friends, or simply spreading out, this home gives you options. Better yet, many of the big-ticket improvements are already in place, including new plumbing in 2012, a new roof in 2023, impact-resistant windows, updated kitchen and baths, and updated flooring throughout. What makes 90 Oakland Hills Place special isn’t just one feature—it’s the combination of 2,305 square feet of air-conditioned living space, extensive updates, a two-car garage, flexible living areas, mature landscaping, an end-of-the-cul-de-sac location, and those sweeping golf-course views. The projects are done. The space is here. The Florida sunshine is waiting. Bring your flip-flops, move right in, and start enjoying the laid-back Florida lifestyle you’ve been dreaming about.

90 Oakland Hills Court, Rotonda West

160 Annapolis Lane, Rotonda West
$274,000
3 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
BRAND NEW 2026 ROOF!!! ** WATERFRONT HAVEN WITH CURB APPEAL IN ROTONDA WEST ** DO NOT MISS!!! From the moment you pull up the sweeping, expansive driveway, this property captivates with undeniable Florida charm. Step onto the stone pathway and pass through an artistic, open-air decorative gate that reveals a private, tranquil front courtyard. Double entry doors give more architectural design that seamlessly blends the unique style of this spacious waterfront 3-bedroom, 2-bath home offering 1,777 square feet of living space on a beautiful canal setting, in the Oakland Hills of Rotonda West. The welcoming oversized Foyer almost stretches the length of the house, and you'll appreciate the generous living areas and easy-flowing floor plan within, along with multiple views of the waterfront as you pass through. This home offers a great opportunity of easy living and at the price, the ability to update it to your own style. The primary bedroom and back bedroom showcase waterfront canal views with sliders that allow for easy access to the backyard. That's where the Florida lifestyle really comes into focus. Enjoy beautiful sunsets and your own waterfront backdrop, whether you're relaxing with your morning coffee, entertaining friends or simply unwinding at the end of the day. An attached 2-car garage provides additional parking, laundry area and storage. Located in established Rotonda West, you're close to golf, boating, fishing, beaches, shopping and dining, with Englewood Beach and Boca Grande within easy reach. If you've been searching for a waterfront home with HURRICANE ACCORDIAN SHUTTER PROTECTION ** IMPACT WINDOWS... With TLC... At this price point there is room to make it your own, 160 Annapolis Lane deserves a closer look. Come see the potential and stay for the water view. Use showing time or call for showings. This is an outstanding opportunity to own a canal-front home in Rotonda West. HVAC 2009, ROOF 2026, WATER HEATER 2013, Take a look today! Easy to show!

160 Annapolis Lane, Rotonda West

199 Caddy Road, 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

55 Rotonda Circle, Rotonda West
$599,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
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

231 Caddy Road, Rotonda West
$305,600
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv. ⋅ 33947 Zip Code
WATERFRONT • HEATED POOL • 4 BEDROOMS • TURNKEY OPTION Welcome to your Florida waterfront escape! This spacious 4-bedroom, 2-bath home combines relaxed indoor-outdoor living with a private heated pool, screened lanai and peaceful freshwater canal views in desirable Rotonda West. Step outside and enjoy the Florida lifestyle from your own backyard—morning coffee overlooking the water, afternoons by the pool and plenty of covered and screened space for entertaining family and friends. Inside, the home offers a comfortable split-bedroom layout with generous living spaces and flexibility for visiting family, guests or a home office. One of the guest bedrooms features sliding-door access directly to the pool deck and beautiful water views, creating a private retreat for visitors. MAJOR UPDATES provide added peace of mind: • Roof – 2021 • HVAC – 2020 • Electrical Panel – 2022 • Fiberglass Pool • Pool Heater – 2024 • Pool Motor – 2025 The home can be offered turnkey/furnished, making it easy to start enjoying Southwest Florida right away. Located in the established Rotonda West community with a remarkably low HOA, you'll be close to golf, Gulf beaches, boating, fishing, restaurants and everything the Englewood area has to offer. Whether you're looking for a full-time Florida home, a winter retreat or a property with flexible future possibilities, 231 Caddy Road offers a hard-to-find combination of 4 bedrooms, waterfront living and your own heated pool. Come experience the water, sunshine and Florida lifestyle for yourself.

231 Caddy Road, Rotonda West

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