Location: Rotonda West Oakland Hills, Rotonda West
Do Not Show Listings
181 CADDY RD, ROTONDA WEST, FL 33947
$322,500225 Days on yellowkey MLS ID: D6142842
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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,028
Elementary School: Vineland Elementary
High School: Lemon Bay High
Tax Year: 2024
Middle School: L.A. Ainger Middle
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 is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)
Listing Agent: Terri Hesse (941-662-6466)
202 CADDY RD, ROTONDA WEST, FL 33947
$384,90026 Days on yellowkey MLS ID: D6146788
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
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: 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, hurricane impact windows and an impact garage door, complemented by additional high end 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)
33 CADDY RD, ROTONDA WEST, FL 33947
$320,000145 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
$275,00043 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.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-473-8484)
Listing Agent: Carla Stiver, Pa (941-270-1460)
30 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$129,200149 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
$354,000778 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
$169,00080 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
$259,90046 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.
Listing Agent: Ryan Hesse (941-716-4448)
18 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$359,0009 Days on yellowkey MLS ID: C7524184
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
Taxes:$6,402
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)
36 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$300,00044 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
$375,00097 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)
231 CADDY RD, ROTONDA WEST, FL 33947
$328,00017 Days on yellowkey MLS ID: C7524452
REDUCED by $10,000 (3.0%) on 04/17/2026
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)
39 CADDY RD, ROTONDA WEST, FL 33947
$244,800299 Days on yellowkey MLS ID: D6142884
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1480 Built: 1974Monthly Fee: $16 Tax: $1,386 (2024)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$1,386
Remarks: Beautifully Updated Home with Owned Solar Power & Canal Views in Rotonda West This move-in ready 2-bedroom + den, 1-car garage home offers incredible value, modern upgrades, and eco-friendly living. With a seller-paid solar system (with strong offer) installed in 2023, enjoy ultra-low electric bills—averaging under $50/month. Set on a wide canal with a fully fenced backyard, this property offers both privacy and space. You'll love the large sunroom, dedicated tanning area, and plenty of room to add a pool, creating your own Florida oasis. Recent upgrades include a new roof (2022), re-piped plumbing (2009), and impact windows 2009, in most windows for peace of mind. Inside, the home features a beautifully remodeled kitchen, granite counters and updated bathrooms, no carpet throughout, and a flexible floor plan with a den that can easily be converted back into a third bedroom. Located in an established neighborhood just 9 miles or 17 minutes to the Manasota Key beaches. Golf courses within the community, shopping, and dining are close by. This home is perfect for full-time living, a seasonal getaway, or an investment opportunity. Don’t miss your chance to own this upgraded Florida gem—schedule your private showing today!
Listing Agent: Tom Wenck Llc (941-276-5824)
31 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$222,00028 Days on yellowkey MLS ID: D6146511
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1192 Built: 1984Monthly Fee: $16 Tax: $3,590 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$3,590
Remarks: If you are looking for a home on the golf course with a lovely water view, without breaking the bank, this is one you will want to check out. Located on the 8th hole of The Hills Golf Course in the popular deed-restricted community of Rotonda West, this 2 bedroom, 2 bath, 2 car garage home has had many updates, and is just waiting for someone to add their personal touch. A new roof was put on in 2024, and a new AC system and Water Heater were installed in August of 2020. Recent updates this year include new solid shaker-style wood kitchen cabinets with soft-close doors and drawers, new quartz kitchen countertops, a new garbage disposal, new carpeting in the primary bedroom, as well as a new bathroom vanity and quartz countertop. New ceiling fans and new window blinds have also recently been installed. The home features ceramic tile throughout the house (except for the primary bedroom), a split bedroom floorplan, and sliding doors to the ceramic tiled lanai. Enjoy Rotonda's 165-acre community park, 30-mile fresh water canal system and excellent golf courses, along with the area's sparkling intercoastal waterways, beautiful Gulf of Mexico beaches, miles of walking and biking trails, tennis courts, restaurants, shopping, and world-class fishing. Make your appointment today! Time to enjoy the Florida sun!
Listing is courtesy of: TALL PINES REALTY (941-475-5015)
Listing Agent: Mary Ann Schmitt (607-329-5415)
12 GOLFVIEW CT, ROTONDA WEST, FL 33947
$289,90012 Days on yellowkey MLS ID: D6147006
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1596 Built: 1974Monthly Fee: $16 Tax: $3,163 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,163
Remarks: This charming two-bedroom, two-bath bungalow blends character with comfort, featuring open-beamed cathedral ceilings, abundant natural light, newer windows, and updated flooring. Located on a quiet cul-de-sac with minimal traffic, this home places you right in the heart of a welcoming golf community—bring your clubs and enjoy easy access to the clubhouse and nearby Boca Grande and Gulf beaches. The spacious family room provides relaxing views of the golf course driving range, while the cozy living room features a rare fireplace—perfect for unwinding at the end of the day. An oversized garage adds exceptional versatility, ideal for storage, hobbies, or showcasing your favorite projects. The private primary suite offers a beautifully updated en-suite bathroom, creating a comfortable retreat with modern finishes and thoughtful design. Thoughtfully maintained and move-in ready, the home offers peace of mind with major updates already completed, including a new roof (2022), A/C (2020), updated electrical panel (2019), hurricane protection (2017), and whole-home repiping (2012).
Listing Agent: Chris Lee (941-467-5537)
2 GOLFVIEW RD, ROTONDA WEST, FL 33947
$365,00021 Days on yellowkey MLS ID: D6146900
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1878 Built: 1973Monthly Fee: $17 Tax: $3,002 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$3,002
Remarks: This beautiful Rotonda West Oakland Hills home is situated on a large corner lot with a majestic Oak and some really nice features 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. 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 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 when you need it ! ! ! Schedule your showing today and see everything this home has to offer.
Listing is courtesy of: THE SUNNYBROOK REALTY LLC (941-474-8000)
Listing Agent: Tim Bronson (941-661-5591)
22 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$234,99959 Days on yellowkey MLS ID: C7522427
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1450 Built: 1981Monthly Fee: $16 Tax: $3,031 (2025)Community: Rotonda WestSpa: NoSingle Family
Taxes:$3,031
Remarks: Enjoy peaceful mornings and beautiful fairway views in this well-maintained Florida home overlooking the Oakland Hills Golf Course, perfectly positioned along the 1st hole. This prime golf course home offers wide green views and a calm setting you will love coming home to every day. The chain-link fenced backyard provides both privacy and function, complete with two man gates and oversized access. It’s perfect for pets, outdoor projects, or extra storage needs. There is plenty of room to create the outdoor space you’ve always wanted while enjoying open golf course views right behind you. Inside, you’ll find new laminate flooring throughout the entire home, giving every room a fresh and modern look. The interior walls have been recently retextured and freshly painted, creating a clean and bright feel from the moment you walk in. Most rooms feature updated light fixtures and ceiling fans, adding style and comfort throughout the home. The primary bedroom stands out with a gorgeous barn door that opens to a thoughtfully designed split bathroom layout. The vanity and sink area offer great function and charm. Both bathrooms have been upgraded with new toilets and shower heads, adding value and peace of mind. The kitchen and bathroom remodels are ready for your inspiration, giving you the chance to design spaces that match your personal taste and style. A home warranty for the new buyer is included, offering extra confidence. There is also a comfortable enclosed area that is perfect for laundry, hobbies, or additional workspace. Major improvements bring lasting value to this Florida golf course property. The roof was replaced in 2022, overhead plumbing was re-piped in 2022, and the lanai was partially rescreened in 2022. Hurricane shutters and a hurricane impact front door installed in 2025 add strong storm protection. Located just 20 minutes from Boca Grande, with easy access to shopping, dining, and Englewood Beach, this move-in ready home combines golf course views, functional outdoor space, and key system upgrades in one great location. Don’t miss this opportunity to relax, entertain, and enjoy the view — this is Florida living done right. Call today to schedule a showing of this great home – it's ready and waiting for you!
Listing is courtesy of: KW PEACE RIVER PARTNERS (941-875-9060)
Listing Agent: Rhonda Gustitus (941-426-4394)
4 GOLFVIEW RD, ROTONDA WEST, FL 33947
$264,90094 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)
76 ROTONDA CIR, ROTONDA WEST, FL 33947
$280,000186 Days on yellowkey MLS ID: D6144344
REDUCED by $10,000 (3.4%) on 04/07/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1743 Built: 1972Monthly Fee: $16 Tax: $4,128 (2024)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$4,128
Remarks: Pool Home with Golf Course Views – Minutes to Beaches! Move right in and enjoy this beautifully maintained 3-bedroom, 2-bathroom pool home in Rotonda West, perfectly situated along the 8th and 9th holes of The Hills Golf Course. Highlights: • Newer Roof for peace of mind • New Pool Cage just completed • Heated Pool with golf course views • Fresh Interior Paint with bright, open living spaces • Turnkey Furnished – ready to enjoy or rent • Oversized Lot with room to garden or add landscaping Location: • Minutes to Boca Grande and Manasota Beaches • Close to five golf courses, boating, and marinas • Near shopping, dining, and medical facilities • Enjoy farmers markets, art festivals, and a low HOA community with walking paths and canals Whether you’re looking for a full-time Florida home or a vacation retreat, this property offers the perfect blend of comfort, convenience, and coastal living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-473-7750)
Listing Agent: Amy Gonzales (360-431-6910)
295 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$280,00032 Days on yellowkey MLS ID: A4687428
REDUCED by $10,000 (3.4%) on 04/06/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1200 Built: 1981Monthly Fee: $18 Tax: $4,836 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,836
Remarks: A True Gem in Rotonda West! Fully renovated and absolutely turnkey, this stunning home is a rare opportunity—perfect for a high-performing Airbnb or your own slice of the Florida lifestyle. Featuring 2 bedrooms plus a bonus room used as a 3rd bedroom, it offers a bright and inviting open-concept living space with a modern kitchen flowing seamlessly into the dining and living areas. Step outside to your spacious heated pool, designed for year-round enjoyment and ultimate relaxation. Major upgrades provide total peace of mind: roof (2022), A/C (2022), new electrical panel, and pool heater (2024). No updates needed, no delays—move in or start generating income from day one. ? This one won’t last!
Listing is courtesy of: VIGOREON INVESTMENTS LLC (941-278-1000)
Listing Agent: Sandrine Maquet (941-278-1000)
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