Rotonda West Oakland Hill Homes with Waterfront

Rotonda West Oakland Hill Homes with Waterfront

Welcome to Rotonda West Oakland Hill, a picturesque subdivision nestled in the heart of sunny Florida, within the charming city of Rotonda West in Charlotte County. This serene community is a hidden gem, offering residents a perfect blend of tranquility and natural beauty, making it an ideal location for those seeking a peaceful retreat or a vibrant lifestyle.

One of the standout features of Rotonda West Oakland Hill is its stunning waterfront properties. Imagine waking up each morning to the gentle sounds of nature and breathtaking views right outside your window. Many homes in this subdivision boast direct access to sparkling lakes and serene canals, providing a perfect backdrop for outdoor activities like fishing, kayaking, or simply enjoying a leisurely stroll along the water's edge. The waterfront lifestyle here is truly unparalleled, allowing residents to embrace Florida's beautiful climate year-round.

The community is thoughtfully designed, featuring lush landscaping and an array of amenities that promote an active and engaging lifestyle. With nearby golf courses, parks, and nature trails, residents can easily immerse themselves in the great outdoors. Additionally, the friendly atmosphere and welcoming neighbors foster a sense of community that makes Rotonda West Oakland Hill feel like home.

Whether you are looking for a tranquil retreat or an active lifestyle, Rotonda West Oakland Hill offers an exceptional living experience. Come and discover your dream waterfront home in this idyllic subdivision, where every day feels like a vacation!

Newest Rotonda West Oakland Hill Homes with Waterfront

$239,500
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
$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
$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
$599,000
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
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
$305,700
4 Beds ⋅ 2 Baths ⋅ Rotonda West Oakland Hill SubDv.
Sold TURNKEY, or blank slate for your personalization. WATERFRONT and Well BELOW MARKET VALUE!!! Welcome to this spacious 4-bedroom pool home located in the active golf course community of Rotonda West. Enjoy the best of Southwest Florida living in this tastefully curated home that comes ready for immediate income production, full time enjoyment, or a perfect seasonal retreat. Whether you're golfing at one of the 5 community courses or spending the day at the beautiful nearby parks or Gulf beaches, you will find a dreamy Florida day at your doorstep. Relax or entertain on the expansive, pool deck overlooking a serene freshwater canal. The pool is heated for year-round usage and enjoyment. The rear yard is fenced and ready for your furry guests. A thoughtfully designed split floor plan of 2/2 bedrooms offers generous living space and privacy. The fully furnished set up for the comfortable occupancy of up to 10 occupants. Guests will love the private pool bedroom with sliding glass doors leading directly to the pool deck lounge area. This pool bedroom offers stunning water views and a true retreat-like feel. Recent updates provide peace of mind, including a 2020 HVAC system, 2021 roof, 2022 electrical panel, Fiberglass Pool, 2024 Pool Heater and 2025 Pool Motor. The Rotonda West community also features a private storage area for RVs, boats, and other recreational vehicles. Community is very scenic known for its quiet streets, multiple golf courses, parks, walking trails, and family-friendly amenities including playgrounds, bike paths, and nearby tennis and recreational facilities—making it a great fit for both relaxation and active lifestyles. Opportunity awaits, in this proven income producing home so don't hesitate.

231 Caddy Road, Rotonda West
$39,900
Rotonda West Oakland Hill SubDv.
Opportunity to own a residential homesite in Rotonda West, ideally positioned along Boundary Blvd within a well-established deed-restricted community. Zoned RMF-15, offering flexibility for residential development, including the potential for a custom home or multi-family investment. This property is well located near Rotonda’s golf courses, scenic waterways, parks, and walking trails, with convenient access to shopping, dining, boating, and the Gulf beaches of Englewood and Boca Grande. Whether you are looking to build or invest, this property offers solid potential in a desirable and growing Southwest Florida location.

44 Boundary Boulevard, Rotonda West
$39,000
Rotonda West Oakland Hill SubDv.
This charming, walkable neighborhood is surrounded by both new and mature homes and friendly neighbors. Clean and cleared lot 80 X 120 on a fresh water canal. Drink your coffee in the morning sun and towards the beautiful view of the canal. Build your dock and fish in your backyard and cruise the 20+ mile of connected waterways. It gets even better! City water and sewer and your future neighbors are already in place. Enjoy the sandy beaches nearby on Boca Grande or Manasota Key. 6 min drive to 6 different Golf Courses. Build your dream home or have a great investment! Welcome!

151 Caddy Road, Rotonda West
$39,900
Rotonda West Oakland Hill SubDv.
This cleared parcel is zoned for multi-family development and offers an excellent opportunity for builders and investors. Water, power sewer, & wifi are all available, making your project easier and more cost-effective. Conveniently located in a well- maintained community and just a short drive to area beaches, gold courses, boating, waterfront dining and everyday amenities. Build now or hold for future development in this desirable Southwest Florida location.

40 Boundary Boulevard, Rotonda West
$45,000
Rotonda West Oakland Hill SubDv.
Don't miss out on this cleared lot with city water and public sewer, situated in a peaceful highly sought community! This waterfront property is surrounded by natural beauty, perfect for constructing your dream home. Conveniently located near golf courses, beaches, and local amenities, this lot is ideal for both full-time living or a vacation retreat.

254 Annapolis Lane, Rotonda West
$29,900
Rotonda West Oakland Hill SubDv.
Build your dream home on this beautiful cleared 80x120 waterfront lot located on a freshwater canal in the highly desirable deed-restricted golf community of Rotonda West on the scenic Cape Haze Peninsula. Whether you are ready to build now or invest for the future, this property offers the perfect opportunity to enjoy the Southwest Florida lifestyle. Public water and sewer are available, and residents enjoy access to multiple golf courses, parks, and miles of walking and biking trails. Just a short drive to the Gulf beaches of Boca Grande and Manasota Key, where you can spend your days enjoying boating, fishing, marinas, waterfront dining, shopping, and world-class tarpon fishing. Start planning your Florida dream home today!

41 Caddy Rd, Rotonda West
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