Location: Rotonda West Oakland Hills, Rotonda West
Do Not Show Listings
271 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$399,900153 Days on yellowkey MLS ID: D6144771
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1599 Built: 2010Monthly Fee: $32 Tax: $4,178 (2024)Community: Rotonda West Oakland HillsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,178
Elementary School: Vineland Elementary
High School: Lemon Bay High
Tax Year: 2024
Middle School: L.A. Ainger Middle
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)
208 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$439,90082 Days on yellowkey MLS ID: D6145800
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1720 Built: 1986Monthly Fee: $16 Tax: $3,646 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,646
Tax Year: 2025
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: Tanya Ciccarone (941-961-4383)
62 OAKLAND HILLS PL, ROTONDA WEST, FL 33947
$279,900392 Days on yellowkey MLS ID: D6141512
1 Days Off yellowkey (back on 3/26/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1610 Built: 1975Monthly Fee: $16 Tax: $4,108 (2024)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,108
Remarks: Under contract-accepting backup offers. PRICE REDUCED!!!! THE WHOLE PACKAGE! This sprawling ranch on an oversized lot includes 3 large bedrooms, 2 full baths with an open floor plan on a golf course with a pond in your back yard and comes TURNKEY FURNISHED! The updated kitchen has an abundance of cabinets and counter space including a breakfast bar. The cabinets and drawers are full of everything you could possibly need in a kitchen. The breakfast area in the kitchen has plenty of room for a table for family and guests. The spacious dining room could hold a very large table for entertaining and the the space off the living room includes a bar. Nearly new furnishings adorn the living room with couches that recline, have drink holders, charging stations and are soooo comfortable. There are several patio doors onto the expansive screened in lanai overlooking the golf course and a pond. The split floorplan includes a grand primary bedroom with an ensuite and plenty of closet space. On the other side of this terrific house are two plentiful bedrooms and a full guest bath. The extra 1/2 lot on the side is plenty of room for expansion if you so chose or just extra space for privacy. This home is in mint, move-in condition! What a perfect scenario. Just bring your personal items and move right in! A bonus - this home also has a new roof and is located on a quiet street with no outlet so no thru traffic!!! This beautifully landscaped, turnkey furnished home is PRICED TO SELL! Don't miss out on this one!
9 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$260,000526 Days on yellowkey MLS ID: D6138925
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1388 Built: 1972Community: Rotonda West Oakland HillsSingle Family
Taxes:
Elementary School: None
High School: None
Tax Year:
Middle School: None
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)
72 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$220,00039 Days on yellowkey MLS ID: D6146504
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1337 Built: 1973Community: Rotonda West Oakland HillsSingle Family
Remarks: Exceptional Renovated Home Overlooking the Fairway in the Oakland Hills Section of Rotonda West! This beautifully updated two bedroom, two bathroom classic home offers peace of mind with a 2022 roof and a 2023 air conditioning system, along with a complete interior remodel that makes the home feel like new. The wide driveway and charming exterior create wonderful curb appeal, enhanced by beautiful new landscaping that welcomes you at the entryway. Inside, gleaming luxury vinyl flooring flows consistently throughout the home, making everyday maintenance easy. A large bay window, soft neutral color palette, and an open floor plan connect the kitchen, dining area, formal living room, and family room. Two sets of sliding glass doors fill the space with natural light and create a bright, comfortable setting for everyday living. The kitchen is designed to impress with shaker style cabinetry featuring soft close hinges, quartz countertops, a glass tile backsplash, and a center island that makes both cooking and entertaining enjoyable. The primary bedroom suite features large windows and a stylish barn door leads to the walk-in closet. In the primary bathroom you will find a double sink vanity with custom lighting and mirrors along with a large fully tiled step in shower. The guest bedroom is spacious and includes a reach-in closet, while the nearby guest bathroom features a custom wood vanity, a fully tiled step in shower, and a convenient door that provides access to the patio. A convenient interior laundry area has been thoughtfully incorporated into an oversized closet space, providing room for the washer and dryer while keeping everything easily accessible inside the home. The single car garage provides additional parking and storage so your golf clubs, beach chairs, and outdoor gear are always close at hand. Step outside to the open air patio where you have a front row seat to enjoy peaceful golf course views. Located in the deed restricted community of Oakland Hills, residents enjoy access to golf, tennis, walking and biking paths, and fishing, all just minutes from home. When the beach calls, Englewood Beach is less than 10 miles away and Boca Grande is just under 12 miles, offering beautiful white sand, coastal breezes, and plenty of waterfront dining and tiki bars. Discover the Florida lifestyle waiting for you at 72 Oakland Hills Court.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-473-8484)
Listing Agent: Carla Stiver, Pa (941-270-1460)
256 CADDY RD, ROTONDA WEST, FL 33947
$339,00041 Days on yellowkey MLS ID: D6146423
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1820 Built: 1973Community: Rotonda West Oakland HillsSingle Family
Remarks: Relaxed Golf Course Living on the 16th Green in Rotonda West! This four bedroom, two bathroom golf course pool home in the Oakland Hills section of Rotonda West offers a light and bright interior, open living spaces, and plenty of room for family and friends. Tropical landscaping welcomes you to the property, highlighted by a beautiful Bismark Palm and a distinctive entry wall. Step through the decorative lead glass front door into a split floor plan that opens to a welcoming formal living room, providing a comfortable space to unwind. The well designed kitchen features wood cabinetry, granite countertops, a tray ceiling, tile backsplash, breakfast bar, and closet pantry. Just off the kitchen is a perfect space for a dining nook, while the fully enclosed Florida room beyond overlooks the pool and includes a convenient pass through from the kitchen along with double French doors that open to the lanai and pool area. The ensuite primary bedroom offers a quiet retreat with two large reach in closets. The primary bathroom features a beautifully tiled step in shower, pedestal sink, and a door that leads to a private screened lanai, creating a peaceful outdoor space for reading, relaxing, or enjoying the fresh Florida air. Three additional guest bedrooms each include reach in closets, providing comfortable accommodations for visitors. The recently remodeled guest bathroom includes a solid surface vanity and a fully tiled tub and shower combination, along with a convenient door to the pool area to help keep wet feet off the interior floors. Outdoor living takes center stage on the partially covered and screened lanai, where golf course views create a peaceful backdrop. The PebbleTec deck surrounds the large 15 by 25 pool, offering plenty of room to float in the sunshine or swim laps. Additional updates and upgrades include a 2023 roof, whole house impact windows, a hurricane rated garage door, wood look vinyl and tile flooring throughout, a newer panel box with surge protector, a 2021 air conditioning system, newer gutters, an alarm system, and a Nest thermostat. Located in the golfing community of Oakland Hills within Rotonda West, this deed restricted neighborhood offers activities including golf, tennis, hiking trails, and fishing. The home is also less than ten miles from Englewood Beach where residents can spend the day enjoying the sand and water, dining at local restaurants or tiki bars, or ending the evening with a sunset and several options for live entertainment. From morning coffee overlooking the fairway to afternoons by the pool, this home is ready to be enjoyed at 256 Caddy Road.
66 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$169,000 MLS ID: A4681306
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1459 Built: 1980Community: Rotonda West Oakland HillsSingle Family
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)
168 CADDY RD, ROTONDA WEST, FL 33947
$369,000 MLS ID: A4672636
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1509 Built: 1978Community: Rotonda West Oakland HillsSingle Family
Remarks: MOTIVATED SELLERS! GORGEOUS HOME! Welcome to 168 Caddy Rd in Rotonda West, a beautifully well-maintained pool home perfectly positioned on the golf course in one of Southwest Florida’s most desirable deed-restricted communities. Ultra updated with stylist grey granite counters on sleek modern white cabinets in the kitchen and both bathrooms. This inviting residence features luxury vinyl plank flooring throughout, offering a modern look that’s both stylish and easy to maintain. The layout flows effortlessly to the outdoor living area, where you can relax or entertain while enjoying serene golf course views from your private pool—the perfect backdrop for Florida living all while safe and secure behind your IMPACT WINDOWS (All except the sliders). Rotonda West is known for its low HOA fees ($190 a year!), multiple championship golf courses, and a relaxed coastal lifestyle, all just minutes from Boca Grande beaches, boating, dining, and shopping. Whether you’re seeking a full-time residence, winter retreat, or investment opportunity, this home delivers comfort, value, and location—living the Florida dream on the fairway. 8.6 miles (by road) to Englewood Beach on Manasota Key.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Sean Seward, Pa (941-525-8083)
76 CADDY RD, ROTONDA WEST, FL 33947
$354,000 MLS ID: D6135265
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2504 Built: 1973Community: Rotonda West Oakland HillsSingle Family
Remarks: One or more photo(s) has been virtually staged. A RECENT PRICE ADJUSTMENT MAKES THIS HOME A MUST-SEE! NO FLOODING OR HURRICANE DAMAGE FROM HELENE OR MILTON--MOVE-IN-READY HOME! The opportunity to put your interior decorating skills into overdrive and transform this home into something magical lies within the walls of this charming home, located on a quiet street on a spacious double lot in the heart of the highly desired community of Rotonda West. The UBIQUITOUS UPDATES found here include a NEW roof, AC (split unit), a new pool heater, LVT floors, an updated kitchen and baths, all new interior/exterior doors, new baseboards, fresh interior/exterior paint, new insulation, and updated lighting and fans. For additional appeal, the seller is willing to contribute up to $5,000 towards CLOSING COSTS with an acceptable offer. TWO PRIMARY SUITES and two additional guest bedrooms have been incorporated to accommodate guests comfortably while allowing ample privacy, making this home an ideal seasonal rental. If you prefer, its 2500 sq. ft also allows plenty of room for full-time family life--the choice is yours. Rife with curb appeal, this attractive home stirs a sense of nostalgia with its timeless 'Old Florida' vibe. Upon entry, guests will appreciate a newly screened front porch and a split and open floor plan, with a kitchen designed to be the heart of family life. New shaker-style cabinetry, stainless steel appliances, a pantry closet, and granite countertops make food prep a pleasure. A convenient pass-through window is a whimsical touch, making it easy to deliver food to the dining room and its adjacent family room. The home offers a heated pool encircled with a new aluminum fence set to the backdrop of a tranquil water view with The Hills Golf Course just beyond. The home feels open and flows comfortably, yet traditional structural bones give each room its unique identity. As a result, the home's easy-living interior is open, airy, and washed in sunlight--the perfect milieu for the new homeowner's preferred color palette. Relaxing comes naturally in the TWO PRIMARY SUITES, designed as quiet retreats after a fun-filled and sun-kissed day at the beach, each with its newly updated ensuite bath offering refreshing walk-in showers. The guest bedrooms will comfortably accommodate visitors with a shared bathroom outfitted with a spacious walk-in shower. The large garage is home to a separate laundry room, and for added convenience, there is an additional garage perfect for storing your golf cart. This charming home is filled with memories of happy moments captured in time, and there is plenty of room for more picture-perfect memories to come. It is a comfortable and peaceful gathering place for family and friends and is just waiting for you to call it 'home.' This is your unique opportunity to add your personal decorating touches to create a home of distinction with a classic Old Florida vibe. Rotonda West is a quiet, friendly community located within a short drive to the pristine Gulf beaches of Englewood and Boca Grande. Golf enthusiasts will appreciate the five courses found within the community. The hard work has already been done, so grab your flip-flops and call today to schedule a private showing. Prepare to be captivated by this dynamic community where your vacation never has to end. Your truly sensational Florida lifestyle awaits!
Listing Agent: Terri Hesse (941-662-6466)
181 CADDY RD, ROTONDA WEST, FL 33947
$322,500 MLS ID: D6142842
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1578 Built: 1977Community: Rotonda West Oakland HillsSingle Family
Remarks: A recent price improvement makes this home a must-see! Discover the perfect Florida retreat in this charming and extensively updated home, located on a quiet street in the heart of Rotonda West. Here, you'll find a delightful blend of classic Florida charm and modern amenities. As you arrive, an attractive paver driveway and a cozy screened front porch invite you to explore further. Inside, you'll appreciate the meticulous attention to detail and the numerous updates that have been made throughout the home. The heart of the house is a beautifully designed kitchen, featuring stainless steel appliances, attractive Shaker-style cabinetry (with convenient pull-outs in several cabinets), a large prep island, and stunning Quartzite countertops imported from Brazil. The open-concept layout integrates the kitchen, dining, and living areas, making it an ideal setting for entertaining family and friends. A built-in dry bar (currently in use as a coffee station) in the dining room adds an extra touch of convenience. Sliders lead you to the outdoor entertaining space, where you can relax on the covered patio and enjoy the serene views of the canal. The home's eye-appealing, fresh coastal color palette reflects the tranquil yet vibrant hues of nearby beaches, creating a pleasing atmosphere throughout. The primary suite, along with its adjoining bath, offers a spa-like retreat—perfect for unwinding after a day at the beach. The fully updated ensuite bathroom showcases ADA ACCESSIBILITY FEATURES, including a Roman shower with beautiful subway tile (roll-in) and a 36" entry door. Two additional spacious bedrooms were designed to accommodate guests in comfort, along with a renovated shared bathroom featuring a tub/shower combination with a tile surround and a stylish vanity with a beautiful stone countertop. ADDITIONAL NOTABLE UPDATES INCLUDE A NEW ROOF (with third nail and tie-downs added), HVAC UNIT (with a Halo LED whole-home air purification system), PGT HURRICANE IMPACT-RESISTANT WINDOWS AND DOORS, 'WOOD-PLANK' PORCELAIN TILE THROUGHOUT THE HOME, UPDATED LIGHTING FIXTURES AND FANS, FRESH INTERIOR AND EXTERIOR PAINT, AN IMPACT RESISTANT GARAGE DOOR, WATER HEATER, NEW INTERIOR DOORS AND TRIM, AND AN EPOXY FINISH ON THE GARAGE FLOOR. Rotonda West is a quiet, friendly neighborhood within a short drive to the pristine Gulf beaches of Boca Grande and Englewood. There are world-class fishing and boating opportunities, eclectic dining establishments, and shopping venues nearby. Golf enthusiasts will appreciate the community's five golf courses. Call today to schedule a private showing if you're searching for a distinguished, updated home with numerous upgrades.
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