Rotonda West Oakland Hills Single Family Homes For Sale in Rotonda West - 29 homes

Remarks: What a find! A beautifully remodeled 3 bed, 2 bath home with a living room, family room, dining area in kitchen and a bonus room/den!! The master bedroom has sliders into the bonus room/den and a large walk in closet. Outside you have a deck off the family room. The canal even has fish! The roof was replaced in 2022. There is an affordable HOA fee ($190/year) and an RV/Boat parking lot for an additional fee. The Hills restaurant and Lipinski's Tavern are located in Rotonda West, along with American Legion post 113. Furnishings can convey with a reasonable accepted offer. From AI: Rotonda West is a master-planned, deed-restricted golf community located on the Cape Haze Peninsula. Famous for its circular design, it features 26 miles of canals, multiple golf courses, and is located just 15–20 minutes from the pristine Gulf beaches of Manasota Key and Boca Grande. Outdoor & Golf Lifestyle: The community is centered around an active, outdoor lifestyle. Rotonda contains six golf courses within its boundaries and boasts 30-plus miles of freshwater canals great for fishing, kayaking, and viewing local wildlife.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Claudia Debruyn (781-799-7570)

Remarks: Come take a look at this open concept, 3 Bedroom, 2 Bath, 2 car garage house in Rotonda West. The roof is 3 years old and the garage floor has a new epoxy finish. Sliding doors lead out to a screened in, newly carpeted lanai that has a pool and spa to relax in. A freshwater canal runs behind the property, adding to it's appeal. This property is located not far from local beaches.

Listing is courtesy of: COLDWELL BANKER SUNSTAR REALTY (941-214-3111)

Listing Agent: Tina Kolb (941-223-2027)

Remarks: 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!!!

Listing is courtesy of: KW COASTAL LIVING (941-473-7399)

Listing Agent: Laura Boyd (765-490-5626)

Remarks: 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, 2023 Low Maintenance 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.

Listing is courtesy of: R & R CONSULTING LLC (941-916-1662)

Listing Agent: Ruth Keiling (941-916-1662)

Remarks: Discover **Paradise on a dime** in this fully remodeled **three level home** featuring **3 bedrooms plus a bonus room that can easily convert back into a **4th bedroom**. The property offers **3 full bathrooms”, a **large, updated kitchen**, and an impressive list of recent upgrades including a **new roof**, **impact windows and sliding glass doors**, **new appliances**, **new kitchen cabinets**, **all new flooring throughout**, and a two car garage. Rotonda West is just minutes away from the beautiful beaches of Gasparilla and Boca Grande Islands. Not only does the property have views of five different fairways, but Rotonda West includes five championship golf courses inside your neighborhood.

Listing is courtesy of: BY OWNER.COM (800-296-9637)

Listing Agent: Greg Sullivan (800-296-9637)

Remarks: Under contract-accepting backup offers. Priced to Sell in Rotonda West Oakland Hills! Great investment opportunity or starter home. 2 bedroom, 2 bath, 2-car garage canal front home on the Cape Haze Peninsula close to numerous golf courses, fishing, boating and beautiful SWFL beaches. Ready for you to bring your own touches. Step inside to an open floor plan with living and family room spaces offering large slider to water views, tile flooring and kitchen with stainless appliances. Split floor plan provides privacy for all with large primary bedroom offering separate office area plus private bath with dual sinks. Lots of potential in the backyard to build the lanai and pool of your dreams. This home includes hurricane shutters with accordion shutter on lanai. New Roof in 2025 and A/C in 2022. Great location close to restaurants, shopping, schools and parks. Don't miss this opportunity! Schedule your private showing today!

Listing is courtesy of: COMPASS FLORIDA (941-205-8478)

Listing Agent: Brian Helgemo (941-205-8478)

Remarks: 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.

Listing is courtesy of: REALTY COOPERATIVE (800-704-6411)

Listing Agent: Tony Giglio (513-505-5222)

Remarks: Welcome To your Golf Course Facing Dream Home with an Oversized Pool. This 4 Bedroom 2 Bath Rotonda West Home is Perfect for any Golf enthusiast. The home is located on a nice quiet street with amazing views. This is one you truly must see to appreciate. The home does have a stage 2/ 240 Volt Auto Charger in the garage..

Listing is courtesy of: REALTY ONE GROUP SUNSHINE (727-325-5843)

Listing Agent: Arno Isaian (941-979-1147)

Remarks: Pride of Ownership is what you will see with this Peaceful Retreat! This 3 bedroom 2 bath home with a bright and cheerful open floorplan is in mint, move-in condition. The interior has been recently repainted, updated flooring and spotless throughout. Beautifully landscaped, this home has fantastic curb appeal in the front and a park-like, private retreat in the back with a large patio, hot tub and firepit. Behind this home is a nature preserve so you will always have the privacy - nothing will be built behind you. The well planned kitchen includes wood cabinetry and stainless steel appliances with a 9 ' breakfast bar for those quick meals. A cozy dinette at the end of the kitchen looks out over the backyard beauty. The split floorplan has the spacious master bedroom with en-site bathroom and walk in closet on one side of the home with the guest quarters on the other Two pleasant bedrooms and full bath complement the guest side of the home. The laundry room with newer washer and dryer is next to the kitchen and a large 2 car garage. BONUS: Full building lot is included with this property. Extra space between you and your neighbor! The roof was new in 2022, refrigerator, dishwasher, washer and dryer are new, hot water tank is 3 years old and the garage door opener is 2 years old. The A/C has been regularly serviced. This property never lost power through all three storms and had no storm damage. This home is a gem! A short drive to five beaches, shopping, medical care, schools, and great restaurants! You are going to love this property!

Listing is courtesy of: BRETT BARBER & COMPANY REAL ES (941-474-7121)

Listing Agent: Andrea Barber (941-270-6052)

Remarks: Welcome to 11 Oakland Hills Court in Rotonda West, a thoughtfully updated 3-bedroom, 2-bathroom pool home that blends modern improvements with comfortable Florida living. From the moment you enter, the home offers a bright, open feel with a layout designed for both everyday functionality and easy entertaining. The remodeled kitchen serves as the centerpiece, featuring updated cabinetry, sleek countertops, stainless steel appliances, and a clean, contemporary design that opens naturally to the main living areas. Additional interior updates include a refreshed family room and a remodeled guest bathroom, creating a cohesive, move-in-ready feel throughout the home. Large windows and sliding glass doors bring in natural light while connecting indoor spaces to the outdoor living area. Step outside to a screened-in pool with recently sealed pavers, offering a private and low-maintenance space to relax or entertain. The backyard overlooks a tranquil water view, providing a peaceful setting to enjoy the Florida lifestyle year-round. Major system updates include a new roof (November 2022) and an AC system replaced in 2020, offering added efficiency and long-term value. Located in the Rotonda West community, this home is close to multiple golf courses, parks, walking trails, shopping, dining, and Gulf Coast beaches, making it a convenient option for a variety of lifestyles.

Listing is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)

Listing Agent: Ryan Hesse (941-716-4448)

Remarks: Under contract-accepting backup offers. MOTIVATED SELLERS • GOLF COURSE POOL HOME • IMPACT WINDOWS !! Welcome to 168 Caddy Rd in Rotonda West — a beautifully updated and meticulously maintained pool home perfectly positioned on the golf course in one of Southwest Florida’s most sought-after deed-restricted communities. From the moment you walk in, you’ll notice the stylish modern upgrades throughout, including luxury vinyl plank flooring, sleek white cabinetry, and gorgeous grey granite countertops in both the kitchen and bathrooms. Every detail has been thoughtfully updated to create a bright, clean, and contemporary feel while still feeling warm and inviting. Step outside to your private outdoor oasis overlooking the fairway, where the pool area has been completely redone for peace of mind and effortless Florida living. The pool features new marcite, new tile, a newly resurfaced concrete deck with a beautiful knockdown finish, along with a new pool pump and timer, making this outdoor space as functional as it is relaxing. Plus, the home is protected with IMPACT WINDOWS, offering both security and energy efficiency. Located in the highly desirable Rotonda West community with incredibly low HOA fees of just $190/year, residents enjoy access to multiple championship golf courses while being only minutes from Boca Grande, boating, waterfront dining, shopping, and some of Florida’s most beautiful Gulf beaches. Just 8.5 miles to Englewood Beach on Manasota Key and 8.6 miles to Boca Grande ?? Whether you’re searching for a full-time residence, seasonal escape, or investment opportunity, this home offers the perfect blend of comfort, location, and Florida lifestyle living.

Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)

Listing Agent: Sean Seward, Pa (941-525-8083)

Remarks: This beautiful well maintained Rotonda West Oakland Hills home is situated on a large corner lot with a majestic Oak and some really nice features and upgrades you don't see from the outside. Once you enter the home you are welcomed with a Large Open Living Room/Kitchen/Dining Room area updated in 2019 including floors, granite counter tops, updated cabinets and appliances make you feel right at home in this kitchen. Making your way back to the master suite is the secondary suite with its own bathroom. As you enter the master bedroom sitting area the space really starts to open up as you make your way into the master suite. The first thing you notice is the master bathroom updated in 2021 with soaking tub and shower surrounded by glass and views of your very own private courtyard. If you're looking for the most peaceful area in the house then you found it. The master bedroom shares the pool area and private courtyard with 2 large sliders. If hanging out at the pool with a cocktail is your thing then grab a seat or jump right in, 365 days a year because it's heated which was replaced in 2019 and a new pump in 2025 ! ! The shingle roof was replaced in 2022. New Impact Rated Dining Room Slider in 2023. New soffit & fascia in 2024 along with new gutters in 2025. The current owners took care of most everything leaving you with the responsibility of enjoying it. Schedule your showing today and start enjoying life by the pool in beautiful sunny Florida.

Listing is courtesy of: THE SUNNYBROOK REALTY LLC (941-474-8000)

Listing Agent: Tim Bronson (941-661-5591)

Remarks: Under contract-accepting backup offers. Short Sale. Short Sale Opportunity. Come and see this amazing updated home. It has all new cabinets, Granite Countertops, New Bathrooms and more. The roof is from 2024. A truly must see to appreciate home. It is also in a Cull de sack so not a lot of traffic. A real Nice place to call home. Hurry at this price this one will fly..

Listing is courtesy of: REALTY ONE GROUP SUNSHINE (727-325-5843)

Listing Agent: Arno Isaian (941-979-1147)

Remarks: 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.

Listing is courtesy of: REALTY ONE GROUP MVP (800-896-8790)

Listing Agent: Oleg Lisitsyn (941-441-5277)

Remarks: 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!

Listing is courtesy of: FIVE STAR REAL ESTATE OF FL (616-791-1500)

Listing Agent: Gerald Buck (231-690-0565)

Remarks: One or more photo(s) has been virtually staged. Welcome to your next chapter in Rotonda West's PREMIER GOLFING COMMUNITY! This 3-bedroom, 2-bathroom home with a two-car garage sits on over a QUARTER ACRE with direct golf course views, offering an unbeatable combination of location, lifestyle, and value. Step inside to discover recently updated luxury vinyl plank in the living/dining areas and tile flooring throughout the rest of the home, complemented by modern recessed lighting. The bright, open kitchen features generous cabinet space and flows seamlessly into the dining area—perfect for daily living and entertaining. The spacious living room opens to an expansive backyard with room to add your dream pool while enjoying front-row views of the fairway. The primary suite provides a private retreat with an en-suite bathroom and walk-in closet. Two adjacent bedrooms are perfect for a growing family, guests or home office! Recent upgrades include a newer roof, AC unit with updated ductwork, and hurricane fabric panels for added protection and peace of mind. Rotonda West offers an exceptional Southwest Florida lifestyle, nestled between Englewood and Port Charlotte with access to five golf courses totaling 99 holes. The community features walking and biking trails, a 165-acre park, tennis and pickleball courts, and a playground with pavilion. Pristine Gulf beaches at Manasota Key and Boca Grande are minutes away, while fishing, boating, and kayaking opportunities abound. Explore charming downtown Punta Gorda or Dearborn Street in Englewood for local shops, restaurants, and farmers markets. Convenient to local and regional airports. Low annual HOA fees and city water/sewer services complete this exceptional opportunity—ideal for investors, first-time buyers, or those seeking a seasonal retreat.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-429-3506)

Listing Agent: Barbara Hamerton, Llc (305-496-4732)

Remarks: Peaceful pool home with preserve view! Nestled in a serene setting, this delightful 2-bedroom, 2-bathroom home offers the best of Florida living with lush preserve views and a tranquil backdrop. Located in desirable Rotonda West, this single-family gem includes a spacious open floor plan, a one-car garage, and a private pool—perfect for relaxation or entertaining. As you step inside, you're greeted by an airy living space with abundant natural light that highlights the beautiful tile flooring. The fully equipped kitchen, with plenty of counter space and storage, opens to the dining and living areas, making it ideal for both everyday living and gatherings. The open layout offers privacy, with the spacious primary suite featuring an en-suite bath and large closet, while the second bedroom is perfect for guests or a home office. The screened-in lanai invites you to enjoy Florida’s year-round sunshine, complete with a sparkling pool overlooking the pristine, protected preserve—a natural extension of your backyard that promises peace, quiet, and visits from local wildlife. Situated minutes from golfing, beautiful Gulf beaches, shopping, and dining, this home captures the relaxed Rotonda West lifestyle. Don’t miss this rare opportunity to own a private, peaceful pool home in a stunning location!

Listing is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)

Listing Agent: Alex Bowermaster (513-275-2396)

Remarks: 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!

Listing is courtesy of: EXCELLENT CHOICE REALTY, LLC (941-412-6477)

Listing Agent: Alex Solovyev (941-408-4400)

Remarks: Welcome to paradise located inside the circle of Rotonda West Community, wether you want to be a owner or a investor, this fully furnished, remodeled 4 bed, 2 bath home sits on oversized lote 9,600 sq ft with 1839 Sq ft of living area, new roof, new AC with a high-efficient thermostat, impact windows and doors, dryer and washer, stainless steel kitchen, dishwasher, microwave, electric range with self-cleaning oven, double doors refrigerator, double sink, ceiling fan in all rooms, primary bedroom with walk-in closet, 1 car garage with automatic garage door opener, big paved driveway, sprinkler system, well, smoke detector, screened terrace with lake view, landscaped backyard, close proximity to Manasota Key, low HOA, no CDD.

Listing is courtesy of: LANDMARKS INTERNATIONAL REALTY, INC. (305-310-6961)

Listing Agent: Amed Chavez Santo Tomas (786-405-4054)

Remarks: From the moment you arrive at 242 Annapolis Lane, you’ll feel the soothing natural ambiance that makes Rotonda West so special. Sunshine dances across the façade, welcoming you home, while the peaceful freshwater canal in your backyard quietly calls to the angler in you. Cast a line, sip your morning coffee, or simply watch the water shimmer—this is Florida living at its finest. Step outside to your private oasis, where two majestic mango trees provide shade and seasonal treats. The stamped concrete patio is the perfect place to unwind, entertain, or soak up the coastal breeze. With a fully fenced backyard, your fur babies and little ones can roam freely while you relax knowing they’re safe. Inside, nearly 1,400 square feet of thoughtfully designed living space unfolds. The split-bedroom floor plan offers privacy, with both bedrooms featuring their own en-suite bathrooms. You’ll love the no-carpet design, easy-care flooring, and the bonus den/office/craft room—perfect for hobbies, remote work, or quiet retreats. The kitchen is conveniently located near the laundry room and garage, making grocery days a breeze, and a charming nook beneath the window invites you to create a cozy bistro corner or workspace overlooking the backyard. This home has been lovingly maintained with major updates already done for you: a new roof in 2023, A/C in 2022, new windows in 2021, full repiping in 2013, and a brand-new hot water heater in 2025. Sitting high at 10.2 feet above sea level, the homeowner reports no flooding during recent hurricanes—offering priceless peace of mind. Can be purchased *TURNKEY FURNISHED* for $5,000 (with a few exclusions) outside of the contract! On city water and sewer, and includes a two-car garage. Rotonda West’s low annual HOA of just $190 keeps community standards high without breaking the bank. Need space for your toys? There’s community storage available for boats or RVs. Golfers will love having five public golf courses right in the neighborhood, and beach lovers will appreciate being just 20 minutes from Manasota Key and Boca Grande’s pristine shores. This is more than a home—it’s a lifestyle. Schedule your showing today and start living the Florida dream you’ve been waiting for!

Listing is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)

Listing Agent: Tawnya Hile (941-467-2349)