Location: Rotonda West Oakland Hills, Rotonda West
Do Not Show Listings
18 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$354,00020 Days on yellowkey MLS ID: C7524184
REDUCED by $5,000 (1.4%) on 05/05/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1680 Built: 1973Monthly Fee: $16 Tax: $6,402 (2025)Community: Rotonda West Oakland HillsSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,402
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Beautifully maintained pool home in Rotonda West with a fully screened lanai, perfect for entertaining. This spacious home features an open floor plan, updated flooring, and a modern kitchen with granite countertops, stainless steel appliances, and ample storage. The primary suite offers direct lanai access, and the home includes a new roof (2022) for added peace of mind. Enjoy canal frontage, a heated pool, and a prime location close to golf courses, beaches, dining, and more.
Listing is courtesy of: HOME MATCHMAKING REALTY (941-323-0020)
Listing Agent: Angel Gagliardi (651-703-4333)
11 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$359,9001 Day on yellowkey MLS ID: D6147336
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1737 Built: 1973Monthly Fee: $16 Tax: $5,193 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$5,193
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)
208 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$439,90099 Days on yellowkey MLS ID: D6145800
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1720 Built: 1986Monthly Fee: $16 Tax: $3,646 (2025)Community: Rotonda West Oakland HillsSpa: YesSingle Family
Taxes:$3,646
Elementary School: Vineland Elementary
High School: Lemon Bay High
Middle School: L.A. Ainger Middle
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)
202 CADDY RD, ROTONDA WEST, FL 33947
$359,90037 Days on yellowkey MLS ID: D6146788
REDUCED by $25,000 (6.5%) on 04/29/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1480 Built: 1974Monthly Fee: $16 Tax: $3,632 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,632
Remarks: $25,000 PRICE IMPROVEMENT April 2026!! Best Value in Rotonda! Experience the quintessential Florida lifestyle in this beautifully reimagined, fully remodeled residence situated in the heart of Rotonda West. Perfectly positioned on The Hills Golf Course with a serene pond backdrop, 202 Caddy Road offers a seamless blend of contemporary comfort and absolute peace of mind. This bright and airy open-concept home welcomes you with all-new luxury vinyl flooring and a flood of natural light that highlights the stunning chef’s kitchen. This centerpiece of the home is a showcase of both style and utility, featuring sleek quartz countertops, ample storage within custom soft-close cabinetry, a beautiful tile backsplash, and a suite of brand-new stainless steel appliances. Every detail has been meticulously addressed, from the dedicated interior laundry room with custom cabinets to the fresh interior and exterior paint that extends to expanded driveway and lanai. Designed for the modern homeowner, this property has been mechanically and structurally revitalized to offer a truly "worry-free" move-in experience. Updates include a new roof, new HVAC and ductwork, a new electrical panel, impact garage door, and high-end accordian style Hurricane shutters for added protection and insurance efficiency. Step through the sliders to find an outdoor sanctuary designed for entertaining or quiet relaxation. The beautiful heated pool is protected by a freshly re-screened cage and overlooks the manicured greens of the golf course, while the oversized lanai offers an extra storage room for pool equipment and beach necessities. The curb appeal is equally impressive, featuring all-new professional landscaping that frames the home’s crisp, updated exterior. Offered fully TURNKEY with stylish new furnishings, 202 Caddy Road is an exceptional opportunity for those seeking a year-round residence, a seasonal vacation home, or a high-potential investment for the local rental market. You are perfectly positioned to enjoy the best of the Rotonda area and Cape Haze Peninsula, located just minutes from five championship golf courses and miles of walking trails. Explore the pristine sands of Manasota Beach and the historic charm of Dearborn Street in Englewood, or take a short drive to the world-class fishing and secluded elegance of Boca Grande. With its "like-new" status and prime location, this home is ready for you to move in and start living your best Florida Life!
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Anneliese Morris (863-244-3724)
182 BOUNDARY BLVD #B, ROTONDA WEST, FL 33947
$475,0005 Days on yellowkey MLS ID: C7525347
Bed: 4 Bath: 0.0 Gar: 1 Liv Area Sq Ft: 2357 Built: 1985Monthly Fee: $32 Tax: $7,954 (2025)Community: Rotonda West Oakland HillsApartment
Taxes:$7,954
Remarks: WOW!!! What a great investment opportunity, weather you rent both sides or live in one and rent the other, can't go wrong with this kind of investment!! Fully furnished, very well maintained, NEW ROOF in 2020, NEW AC units in 2023, renovated kitchen and bathrooms!! Close to beautiful parks, nice restaurants and fantastic public beaches and golf courses!! Hurry to make the smartest decision of your life to own this duplex and invest in your future!!!
Listing is courtesy of: REAL ESTATE MAINSTREAM SERVICE (941-625-6200)
Listing Agent: Vadim Sizov (941-456-0067)
231 CADDY RD, ROTONDA WEST, FL 33947
$327,20028 Days on yellowkey MLS ID: C7524452
REDUCED by $800 (0.2%) on 05/01/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1819 Built: 1980Monthly Fee: $16 Tax: $6,012 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$6,012
Remarks: WATERFRONT!!! Welcome to this spacious 4-bedroom pool home located in the sought out golf course community of Rotonda West. Enjoy the best of Southwest Florida living—whether you're golfing at nearby courses or spending the day at the beautiful Gulf beaches just minutes away. Back at home, relax or entertain on the expansive, fenced pool deck overlooking a serene freshwater canal, complete with a heated pool for year-round enjoyment. This thoughtfully designed split floor plan offers generous living space and privacy, ideal for families or hosting guests. One of the standout features is a private guest bedroom with sliding glass doors leading directly to the pool area, offering 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. This home offers incredible versatility—perfect as a full-time residence, seasonal getaway, or investment opportunity. 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. Don’t miss the opportunity to own a well-maintained home in one of the area’s most sought-after communities.
Listing is courtesy of: R & R CONSULTING LLC (941-916-1662)
Listing Agent: Ruth Keiling (941-916-1662)
84 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$339,0006 Days on yellowkey MLS ID: D6147295
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1235 Built: 1986Monthly Fee: $16 Tax: $4,938 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,938
Remarks: Welcome to Annapolis Waterside Escape, a fully renovated (2024) canal-front pool home in Rotonda West offering immediate income potential and effortless Florida living. This 2-bedroom, 2-bathroom home features 1,235 sq ft of thoughtfully updated, open-concept space with luxury vinyl flooring throughout (no carpet), recessed lighting, and abundant natural light. The modern kitchen includes quartz countertops, stainless steel appliances, custom cabinetry, and a stylish tile backsplash, flowing seamlessly into the living and dining areas with views of the pool and lanai. Both bathrooms have been updated with contemporary finishes, and the home also includes an indoor laundry area and 2-car garage. Step outside to a private outdoor retreat with a paver stone pool deck, freeform pool, expansive screened enclosure, and a covered patio with wood-accent ceiling and ceiling fans, all overlooking a wide canal and spacious backyard. Located just minutes from golf courses, walking trails, and approximately 6–8 miles to Englewood Beach and Manasota Key, this property is also a proven turnkey short-term rental with $30,549.98 in gross revenue (Oct 2025–April 2026, excluding taxes/fees), an 84.91% occupancy rate, and $18,973.61 in future bookings as of April 30, 2026, all of which can transfer to a new owner for immediate income.
Listing is courtesy of: PARADISE BREEZE VACATION RENTALS AND REALTY, LLC (941-223-2656)
Listing Agent: Shannon Doell (941-223-2656)
192 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$140,0006 Days on yellowkey MLS ID: A4692021
0 Days Off yellowkey (back on 4/30/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1270 Built: 1984Monthly Fee: $16 Tax: $1,430 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$1,430
Remarks: Under contract-accepting backup offers. LISTED AND SOLD SIMULTANEOUSLY
Listing is courtesy of: PALM PARADISE REALTY GROUP (239-955-7256)
Listing Agent: Debbie Henninger (410-982-3476)
55 ROTONDA CIR, ROTONDA WEST, FL 33947
$645,0007 Days on yellowkey MLS ID: N6144131
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1862 Built: 2026Monthly Fee: $16 Tax: $982 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$982
Remarks: Welcome to your 2026 built, 4 Bedroom, 2 Bathroom, 2 car garage, Pool home on a canal in the charming Oakland Hills district of Rotonda West in beautiful SW Florida! This inviting property is perfect for anyone seeking a peaceful and convenient living experience this area has to offer. This spacious residence features ample square footage, with thoughtfully designed, contemporary living spaces that cater to all your needs. In terms of comfort, this home is equipped with central heating and cooling, high ceilings with trays and ceiling fans, stainless steel appliances, soft close cabinets, porcelain tile throughout, laundry storage and much much more. Slide-away corner glass door really connects indoor and outdoor spaces during those cooler days. Screened pool with large covered lanai offers plenty of room for entertaining and enjoyment. Enjoy nearby amenities, including local restaurants, shopping, beaches, parks, bike trails, fishing, vast canal network and much more. Don’t miss out on this wonderful opportunity to reside in this vibrant community! Schedule a viewing today and discover all that this property has to offer!
Listing is courtesy of: EXCELLENT CHOICE REALTY, LLC (941-412-6477)
Listing Agent: Alex Solovyev (941-408-4400)
4 GOLFVIEW RD, ROTONDA WEST, FL 33947
$264,900105 Days on yellowkey MLS ID: O6375854
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1675 Built: 1973Monthly Fee: $16 Tax: $3,666 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,666
Remarks: Nicely updated 3 Bedroom Home with pool, A. C. Kitchen with wood cabinets, Granite counters and Stainless Steel Appliances. Large Rooms with Living Room and Family Room. Very good condition inside and out! Large pool and located on the Greenbelt. Just a short drive to Englewood Beaches! One block away from the Golf Club House of Rotonda West. Located on a quiet street. 10 minutes to the beach. 5 minutes to Walmart. The house has all new plumbing done in 2023. No hurricane damage. Furniture can be included in the sale of the home.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
72 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$220,00056 Days on yellowkey MLS ID: D6146504
1 Days Off yellowkey (back on 4/27/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1337 Built: 1973Monthly Fee: $16 Tax: $3,121 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,121
Remarks: Under contract-accepting backup offers. 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)
181 CADDY RD, ROTONDA WEST, FL 33947
$322,500236 Days on yellowkey MLS ID: D6142842
0 Days Off yellowkey (back on 4/26/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1578 Built: 1977Monthly Fee: $16 Tax: $1,028 (2024)Community: Rotonda West Oakland HillsSingle Family
Taxes:$1,028
Tax Year: 2024
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.
Listing Agent: Terri Hesse (941-662-6466)
33 CADDY RD, ROTONDA WEST, FL 33947
$320,000156 Days on yellowkey MLS ID: A4673763
2 Days Off yellowkey (back on 4/7/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1490 Built: 1974Monthly Fee: $16 Tax: $5,087 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$5,087
Remarks: Under contract-accepting backup offers. Welcome to this beautifully renovated FULLY FURNISHED canal-front pool home located in the desirable deed-restricted golfing community of Rotonda West – Oakland Hills. This updated 3-bedroom, 2-bath, 2-car garage home offers modern comfort, serene water views, and an inviting layout perfect for enjoying the Florida lifestyle. Recent improvements include a 2024 steel pool cage, 2023 exterior paint, 2023 gutters, and luxury vinyl plank flooring throughout the home, providing both durability and a modern look. The kitchen features quartz countertops, updated cabinetry, and newer appliances, including a smooth-top stove and double-door refrigerator. A charming courtyard-style paver patio welcomes you at the entrance, ideally positioned facing northwest to capture beautiful Florida sunsets. Inside, the living and dining area features cathedral ceilings and an open, airy feel that flows comfortably throughout the home. The kitchen offers a convenient passthrough to the adjoining family room and opens to a cozy dinette area with additional cabinetry, a built-in desk, and sliding glass doors leading to the lanai, creating a perfect space for casual dining. The family room features extra storage, impact windows, and a comfortable setting for relaxing or entertaining guests. The primary suite, privately located at the rear of the home, includes two wall closets, a ceiling fan, and an updated ensuite bathroom with a raised-height vanity, modern lighting, new shower, new toilet, and updated flooring. The guest bedroom is generously sized with a wall closet and ceiling fan, while the guest bathroom has been refreshed with a new vanity with a cultured marble top, updated lighting, a new toilet, and a tub/shower combination. The spacious vinyl-enclosed lanai is ideal for outdoor entertaining and overlooks the pool and peaceful canal, offering a relaxing setting year-round. Additional updates include a new roof installed in 2023, a water heater replaced in 2020, and an impact-resistant garage door (2013). With five golf courses just minutes away, along with world-class fishing, beautiful Gulf beaches, dining, and shopping nearby, this home places you in the heart of the Southwest Florida lifestyle. Move-in ready and offered fully furnished, this canal-front pool home is the perfect opportunity to start enjoying Florida living.
Listing is courtesy of: CALL IT CLOSED INTL REALTY (407-338-3339)
Listing Agent: Sasha Volosevych (971-703-0307)
9 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$275,00054 Days on yellowkey MLS ID: D6146596
1 Days Off yellowkey (back on 4/12/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1192 Built: 1985Monthly Fee: $16 Tax: $3,548 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,548
Remarks: Under contract-accepting backup offers. Modern Luxury Meets Beautiful Pond and Golf Course Views in This Fully Remodeled Oakland Hills Home! Enjoy peace of mind with impact windows and an impact garage door, an X flood zone classification for the home structure, a 2024 roof, and a complete interior renovation. The charming exterior, highlighted by a long driveway, refreshed landscaping, and inviting curb appeal, sets the stage for the stylish updates found inside. Luxury vinyl plank flooring flows seamlessly throughout this two bedroom, two bathroom home, creating a cohesive and easy to maintain living space. Neutral paint tones and an open great room floor plan fill the home with natural light and create a bright, welcoming atmosphere. The beautifully updated kitchen features white shaker style cabinetry with soft close hinges, quartz countertops, custom hardware, a farmhouse sink, stainless steel appliances, and a large center island with pendant lighting for easy everyday living. The formal dining area offers flexibility with sliding glass doors that open to the screened patio, making it perfect as a dining room or additional family room space with easy access to outdoor living. The primary bedroom suite features sliding glass doors to the lanai, a spacious walk-in closet with a custom organizer system, and a barn style door leading to the private bathroom. Here you will find a dual sink vanity with quartz countertops and a large fully tiled walk-in shower with niche detail and a rain style shower head. The guest bedroom includes two reach-in closets and also functions as an ensuite with a beautifully updated bathroom featuring a quartz topped vanity and fully tiled walk-in shower. A convenient second door allows this bathroom to be accessed from the kitchen area as well. Step outside to the covered and screened patio with tile flooring that overlooks the backyard and the scenic pond and golf course beyond. The spacious yard offers room to add your own pool, expand the patio, or create a garden or outdoor entertaining area while enjoying peaceful water and golf course views as your backdrop for relaxing evenings under the stars. Located within the Oakland Hills section of Rotonda West, this deed restricted community offers an active Florida lifestyle with golf, tennis, pickleball, hiking trails, community events, and excellent fishing opportunities nearby. The home is also less than ten miles from Englewood Beach where residents can enjoy sunny days on the sand, waterfront dining, local restaurants and tiki bars, or beautiful Gulf Coast sunsets with live entertainment. From morning coffee overlooking the water and golf course to evenings enjoying the peaceful outdoor setting, this beautifully renovated home is ready to be enjoyed at 9 Oakland Hills Court.
30 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$129,200160 Days on yellowkey MLS ID: C7517487
2 Days Off yellowkey (back on 2/20/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1593 Built: 1973Monthly Fee: $16 Tax: $3,436 (2024)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,436
Remarks: Located in the desirable Rotonda West community, this three-bedroom, two-bath home offers excellent potential for buyers looking for a complete remodel. The property sits along a quiet canal, offering views of a golf course and a scenic backdrop for future improvements. The interior is ready for an update, making it an ideal canvas for redesign and added value. Rotonda West is known for its five community golf courses, plentiful walking paths, parks, and convenient access to beaches, dining, and shopping. With its prime location and solid footprint, this home offers a valuable opportunity for those seeking a high-potential project in the established Rotonda West Community. FHA Case # 095-024231-: IE (Insured Escrow) 203K Eligible. FHA $100 Down Eligible. Sold AS IS. See docs for disclosure. Information is not guaranteed. Equal Housing Opportunity. The buyer pays all transfer fees, doc stamps, and title insurance. The buyer is responsible for utilities during inspections.
Listing is courtesy of: FLORIDA REALTY COASTWIDE LLC (732-539-6539)
Listing Agent: William Cassie (732-539-6539)
76 CADDY RD, ROTONDA WEST, FL 33947
$354,000789 Days on yellowkey MLS ID: D6135265
3 Days Off yellowkey (back on 4/22/2026)
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2504 Built: 1973Monthly Fee: $32 Tax: $1,088 (2023)Community: Rotonda West Oakland HillsSingle Family
Taxes:$1,088
Tax Year: 2023
Remarks: Under contract-accepting backup offers. 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!
66 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$169,00091 Days on yellowkey MLS ID: A4681306
0 Days Off yellowkey (back on 2/19/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1459 Built: 1980Monthly Fee: $16 Tax: $4,174 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,174
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)
47 OAKLAND HILLS PL, ROTONDA WEST, FL 33947
$259,90057 Days on yellowkey MLS ID: D6146545
0 Days Off yellowkey (back on 4/20/2026)
REDUCED by $10,000 (3.7%) on 04/15/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1455 Built: 1978Monthly Fee: $16 Tax: $4,248 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,248
Remarks: Under contract-accepting backup offers. Welcome to 47 Oakland Hills Place in Rotonda West, Florida—a well-maintained 3-bedroom, 2-bathroom home with a 2-car garage offering scenic golf course and water views in a sought-after community setting. Important updates provide added value and peace of mind, including a new roof (December 2022), hurricane impact windows installed in 2017, and an HVAC system replaced in 2018. The interior has been recently refreshed with new paint and updated flooring, creating a bright and inviting atmosphere throughout the home. The spacious living room is filled with natural light and flows seamlessly into the dining area, where double sliding glass doors frame relaxing views of the golf course and lake. The kitchen offers generous cabinetry, ample countertop space, and a comfortable dinette area, while the adjacent flexible space can function as a family room, office, or additional seating area depending on your needs. The split-bedroom floor plan offers a functional layout with separation between the primary suite and guest bedrooms. The two guest bedrooms feature luxury vinyl plank flooring installed in January 2023 and share a full bathroom. The primary suite, updated with luxury vinyl plank flooring in 2025, includes two walk-in closets and a private en-suite bathroom. Outdoor living is highlighted by a covered and screened lanai where you can enjoy peaceful views of the golf course, water, and surrounding natural landscape. The property also includes a programmable irrigation system designed to maintain the lawn and landscaping with ease. Located within Rotonda West, the community features multiple golf courses, walking trails, and a clubhouse, while remaining just a short drive from shopping, dining, boating, fishing, and the Gulf Coast’s beautiful beaches. This property combines recent updates, comfortable living spaces, and a scenic setting in one of the area's well-known golf communities.
36 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$300,00055 Days on yellowkey MLS ID: D6146552
0 Days Off yellowkey (back on 4/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1389 Built: 1974Monthly Fee: $16 Tax: $2,622 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$2,622
Remarks: Welcome to relaxed Florida living in Rotonda West, located on the scenic Cape Haze Peninsula just minutes from the beaches and charm of Boca Grande. Surrounded by boating, fishing, kayaking, biking, golf, shopping, and fantastic restaurants, this home offers the perfect blend of comfort, convenience, and coastal lifestyle. This beautifully updated two-bedroom, two-bathroom home features a spacious, open floor plan designed for easy living and entertaining. The home offers both a living room and family room that flow seamlessly into the dining area, creating a bright and inviting space for gatherings. Large sliding glass doors open to the lanai, extending the living space outdoors and making entertaining effortless. The remodeled kitchen is ideal for hosting with white cabinetry, granite countertops, and generous prep space, offering plenty of room for two cooks. Tile flooring runs throughout the home, and both bathrooms have been tastefully updated with modern showers and vanities. Step outside to an expansive 50' screened lanai with a large 13' x 26' covered area, perfect for outdoor dining, relaxing by the pool, or enjoying beautiful Florida evenings. The second bathroom provides convenient access from the pool area, making outdoor living and entertaining even easier. The pool was resurfaced in 2023, and the pool heater thermostat was replaced in 2026. The canal-front setting includes a private dock—an ideal spot for fishing, bird watching, or simply enjoying peaceful water views. Spectacular sunsets from the lanai make every evening special. The yard is nicely landscaped, and a screened front porch welcomes you into the home. Additional updates and features include: • Roof replaced in 2022 • Exterior of the home painted in 2023 • A/C approximately 4 years old • Dishwasher and microwave only 1 year old • Sprinkler pump replaced 3 years ago • Irrigation supplied by the canal with a Raindance controller system • Driveway widened for easier parking • One-car garage with washer and dryer • No history of water intrusion The property is being sold turnkey, meaning everything stays, including a brand-new smart TV purchased in 2026, making this an easy move-in-ready opportunity. Public records reflect a three-bedroom home, though it is currently configured as two spacious bedrooms. Located in the quiet and desirable community of Rotonda West, this home offers easy access to the world-class fishing, beaches, and boating around Boca Grande, along with miles of nearby golf courses, scenic bike paths, and nature trails. Move right in and start enjoying the Southwest Florida lifestyle. ????
Listing is courtesy of: MICHAEL SAUNDERS & CO. - BOCA (941-964-2000)
Listing Agent: Marcy Davis (941-685-5005)
16 OAKLAND HILLS PL, ROTONDA WEST, FL 33947
$375,000108 Days on yellowkey MLS ID: D6145679
REDUCED by $14,900 (3.8%) on 04/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1804 Built: 1973Monthly Fee: $16 Tax: $4,825 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,825
Remarks: Looking for THE ONE that checks ALL THE BOXES?!...Golf Course view, Heated Pool, Open Floor Plan, Updated, and Turn-Key Furnished! This beautiful home has been extensively updated, featuring a NEW roof (2023), NEW A/C (2022), ALL impact windows (2022), and SOLAR PANELS for peace of mind and energy efficiency. The interior has been completely remodeled with new kitchen, baths, and luxury vinyl flooring throughout—no carpet anywhere. The bright, stunning kitchen is a showstopper, offering stainless steel appliances, a sit-up island, and a pantry cabinet, all open to the dining area and spacious family room with elegant plantation shutters—perfect for everyday living and entertaining. The second bathroom conveniently opens directly to the pool and lanai, ideal for seamless indoor-outdoor living. Enjoy incredible savings with solar panels - the average electric bill is only $45 a month, LOW HOA fees of only $190 a year, and NO CDD fees. Relax in the nice sized heated pool and take in the phenomenal views of the 16th hole and fairway of The Hills Golf Course. Rotonda offers an outstanding lifestyle with five public golf courses, walking trails, tennis courts, a playground, and a community center, all nearby to Englewood Beach and Boca Grande Island, with many shopping and dining options close by. Perfect home if you are looking for a permanent home, vacation getaway spot, or investment property. Move-in ready, stylish, and perfectly located—this home is a must-see!
Listing is courtesy of: RE/MAX PALM REALTY OF VENICE (941-451-2025)
Listing Agent: Laurie Sandoval (941-662-8190)
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