Displaying: For Sale
Location: Rotonda West
Property Type(s): Single Family
Living Area Square Feet: 1000 to 1499
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Rotonda West - 22 properties found
202 CADDY RD, ROTONDA WEST, FL 33947
$359,90035 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,632
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
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)
155 CADDY RD, ROTONDA WEST, FL 33947
$329,90012 Days on yellowkey MLS ID: D6147136
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1346 Built: 1979Monthly Fee: $16 Tax: $4,928 (2025)Community: Oakland Hills SecSingle Family
Taxes:$4,928
Elementary School: Vineland Elementary
High School: Lemon Bay High
Middle School: L.A. Ainger Middle
Remarks: Make your Florida dreams come true with this WATERFRONT home in Rotonda West, where BREATHTAKING WATER VIEWS, a NEW PRIVATE DOCK, and resort-style outdoor living create an unforgettable first impression. This home is designed to stand out, featuring a HEATED INGROUND POOL, OUTDOOR SHOWER, and an OVERSIZED SCREENED-IN LANAI with a PARTIAL COVERED AREA—perfect for entertaining, relaxing, and enjoying the coastal breeze year-round. Enjoy added peace of mind with HURRICANE-IMPACT WINDOWS, a NEWER ROOF, and a desirable location in the X FLOOD ZONE. Simply pack your swimsuits and flip flops and come enjoy this TURNKEY FURNISHED RETREAT. Whether you’re hosting sunset dinners or savoring quiet mornings by the water, this home delivers the lifestyle people move to Florida for. Inside, the home blends standout features with a smart layout. The SPACIOUS PRIMARY SUITE offers a large WALK-IN CLOSET, a PRIVATE EN-SUITE BATHROOM, and sliding glass doors that open directly to the lanai, bringing the outdoors in. The SPLIT-BEDROOM DESIGN adds privacy, with the second bedroom tucked into its own wing alongside a FULL BATHROOM THAT ALSO FUNCTIONS AS A POOL BATH with DIRECT LANAI ACCESS. The kitchen is both stylish and functional, boasting GRANITE COUNTERTOPS and STAINLESS STEEL APPLIANCES with an easy flow into the main living space—perfect for everyday living and entertaining alike. Located a short drive from the pristine Gulf shores of Boca Grande Beach and Englewood Beach, this home places you close to some of the best boating, fishing, and beach days Southwest Florida has to offer. Rotonda West is known for its active lifestyle, with multiple GOLF COURSES, parks, and scenic surroundings that make it a highly desirable place to call home. With its combination of key upgrades, thoughtful design, and unbeatable WATERFRONT setting, this property truly stands apart. Call today to view this property and start living the life you deserve!
Listing is courtesy of: KW COASTAL LIVING (941-473-7399)
Listing Agent: Leslie Brown Pa (941-681-3420)
84 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$339,0004 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
$140,0004 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)
529 SUNSET RD N, ROTONDA WEST, FL 33947
$299,00068 Days on yellowkey MLS ID: A4683876
REDUCED by $9,750 (3.2%) on 04/27/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1487 Built: 2017Monthly Fee: $8 Tax: $2,921 (2025)Community: Rotonda HeightsSingle Family
Taxes:$2,921
Remarks: Welcome to Rotonda Heights! On a quiet street, this beautifully maintained 2017 Luke Brothers custom-built 3 bedroom, 2 full bathroom, 2 car garage block home in the desirable community of Rotonda West! Enter to foyer and living room with high ceilings and a double tray with lights. LIVING-KITCHEN - FAMILY ROOMS are open. KITCHEN features a breakfast bar. The Living Room has sliding glass doors to the screened lanai. The 2-car garage that walks into the hallway with laundry closet with a clothes washer and dryer that convey. This thoughtfully designed residence combines comfort, efficiency, and Florida lifestyle. The open floor plan and functional layout is enhanced by ceramic tile flooring throughout, providing a seamless look that’s both stylish, easy to maintain and cool underfoot in hot summer weather. Enjoy peace of mind with energy-efficient windows, helping to keep utility costs down while maximizing natural light. For added storm protection, hurricane shutters are conveniently stored in the garage. Recent exterior updates include new landscaping and a freshly painted front door, adding to the home’s inviting curb appeal. Landscaped yard includes palm trees, a plumeria tree that blooms beautifully in warmer months and offering a touch of tropical charm and seasonal color. Concrete driveway and sidewalks are well poured and have no cracks. Step outside to relax or entertain on the screened-in rear patio, perfect for enjoying Florida’s year-round sunshine without the bugs. ROOM FOR A POOL. This move-in-ready home is ideal for full-time living, a seasonal retreat, or an investment opportunity. Schedule your private showing today and experience the best of Florida living!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Anna Lee Williams (240-315-4672)
15 MARINER LN, ROTONDA WEST, FL 33947
$369,00011 Days on yellowkey MLS ID: D6147164
0 Days Off yellowkey (back on 4/27/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1480 Built: 1992Monthly Fee: $16 Tax: $5,831 (2025)Community: Rotonda West PinehurstSpa: YesSingle Family
Taxes:$5,831
Elementary School: Myakka River Elementary
Middle School: SKY Academy Englewood
Remarks: Under contract-accepting backup offers. DON'T FORGET TO TAKE A LOOK AT THE VIDEO AND VIRTUAL TOUR ABOVE** Discover your own backyard sanctuary at 15 Mariner Ln in Rotonda West. This fully furnished "Turn-Key" 3-bed, 2-bath home delivers style, updates, and location. Standout Features: Outdoor Living: Sparkling solar-heated pool resurfaced in 2026, with a spa, all under a screened-in lanai for year-round enjoyment. New Pentair pool motor & equipment installed in 2025 (pool automation via your phone). Kitchen: Custom wood cabinetry paired with granite countertops and stainless steel appliances from 2021.Throughout: Wood plank porcelain tile, custom shelving in all closets, and epoxy garage floor for a polished finish.Systems: Irrigation pump upgraded in 2026, plus an irrigation well for efficient landscaping.Location Amenities: Minutes from Rotonda West golf courses, Englewood and Boca Grande beaches, local boat marinas, walking/biking paths, and nature preserves. This one blends modern updates with Florida resort living, all in a sought-after Rotonda West community.
Listing Agent: Benjamin Webb (941-592-9490)
72 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$220,00054 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)
33 CADDY RD, ROTONDA WEST, FL 33947
$320,000154 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
$275,00052 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.
66 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$169,00089 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
$259,90055 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 is courtesy of: PARADISE EXCLUSIVE INC (941-698-0303)
Listing Agent: Ryan Hesse (941-716-4448)
36 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$300,00053 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)
39 CADDY RD, ROTONDA WEST, FL 33947
$244,800308 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
Tax Year: 2024
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)
244 ROTONDA CIR, ROTONDA WEST, FL 33947
$330,00020 Days on yellowkey MLS ID: D6147037
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1303 Built: 1984Monthly Fee: $16 Tax: $4,299 (2025)Community: Rotonda West Pebble BeachSingle Family
Taxes:$4,299
Remarks: IMMACULATE & FULLY UPDATED home with increible water and golf course views located in the desirable deed-restricted community of Rotonda West. This home has been completed remodeled featuring new porcelain tile throughout, updated kitchen & baths, new lighting & ceiling fans, all interior doors replaced, the interior and exterior have recently been painted, & the roof was replaced in 2023. Approaching the front screened-in entry and entering the home, you will find everything you could ever want in a home and more! This open floor plan is desirable for every occasion featuring a large living room, dining area, family room, and a Florida room. The spacious eat-in kitchen area--recently remodeled with soft-close wood cabinets and drawers, new recessed lighting, quality LG stainless steel appliances including a double oven, range, refrigerator, microwave, and garbage disposal all replaced within the last 4 years, beautiful granite countertops, plus a closet pantry, and a breakfast bar--all open to the family room where you can catch a glimpse of tranquil views and surroundings. Easily expand your living space outdoors where you can enjoy the sun and shade in your backyard oasis with a private, solar heated, salt water pool with a newer pool pump (2024), and ample seating space under the covered lanai--all surrounded by peaceful water and golf course views, you will never want to leave. There is plenty of room inside with the "split" bedroom layout--the primary suite is separate with a spacious bedroom featuring the same easy to maintain porcelain tile flooring, a roomy walk-in closet, sliding glass doors out to the Florida Room & the ensuite bathroom-- tastefully upgraded with granite countertops, a new vanity with wood cabinets and pullout drawers, upgraded lighting, new toilet and a spacious shower with floor-to-ceiling tiled walls, and matching stone floor. On the opposite end of the home, there is the guest bedroom & bathroom--the bedroom features a walk-in closet, ceiling fan, and light and airy colored walls--just across the hallway is the guest bathroom that has been updated with a new vanity, granite countertops, new lighting, a new toilet, and a walk-in shower with floor-to-ceiling tiled walls. Combine all of this with an interior laundry room that has a utility sink, plus cabinets and a closet for additional storage and a door to the roomy 2-car garage. Additional updates include: Hot Water Heater: 2024, Side garage door replaced in 2021 & overhead garage opener replaced in 2022, and the solar heat for the pool was installed in 2016. Don’t wait, come live the Florida dream! Enjoy the five golf courses Rotonda West offers along with walking trails, pickleball courts and freshwater canals for kayaking all just minutes away. Conveniently located near shopping, restaurants, beaches, fishing, local farmers markets and so much more. Make this home your dream come true.
Listing Agent: Katie Smallwood, Pa (941-468-1189)
31 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$222,00037 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)
22 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$234,99968 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)
295 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$280,00041 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)
157 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$239,00033 Days on yellowkey MLS ID: D6146859
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1172 Built: 1996Monthly Fee: $16 Tax: $4,015 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$4,015
Remarks: Welcome to wonderful Rotonda, hidden away but close to everything. Minutes to local Gulf Beaches and Rotonda is a great golfing community with 5 beautiful courses. Fresh water canals and lakes throughout. A must to see for your winter getaway or your full time home in Paradise. This 3 bedroom and 2 bath home has a large lanai across the back of the home with a large back yard with privacy there are no houses behind you.
Listing Agent: Barbara Luciano (941-223-4337)
33 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$234,00087 Days on yellowkey MLS ID: D6145987
REDUCED by $11,000 (4.5%) on 04/02/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1185 Built: 1975Monthly Fee: $16 Tax: $3,583 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,583
Remarks: Move in Ready Turnkey 2 car garage home in Rotonda West! Excellent location and opportunity for a full-time residence or an AIRBNB income producing property. Close to numerous local Tiki-Bars, Fine Dining, Golfing, Public Boat Ramps and Storage Marinas. Short car drive or boat ride to either Boca Grande or Manasota Key Beach. This home has the popular desired split bedroom floor plan. The primary bedroom and has lots of natural light and private sliding doors out to the enclosed screen lanai. There is another slider off the dining room into the lanai which features an amazing tranquil backyard view of the Preserve. The backyard is enclosed with a black cable vinyl fence with two gates for easy access. Updates include: 2023 Roof *2019 A/C *2026 Hot water heater *2019 Electric Panel and 2019 remodeled kitchen. Call for a Private Showing!
Listing Agent: Tina Evans (315-408-8159)
118 ROTONDA CIR, ROTONDA WEST, FL 33947
$254,00082 Days on yellowkey MLS ID: D6146103
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1986Monthly Fee: $16 Tax: $3,753 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,753
Remarks: ATTENTION GOLFERS + BOATERS! Positioned on an ELEVATED CORNER LOT in Rotonda West, this property captures SWEEPING GOLF COURSE VIEWS of The Hills Golf Course while placing you in the center of it all. A NEW 2023 METAL ROOF adds lasting value and peace of mind, but it’s the setting that truly sets this home apart. Caddy corner to ROTONDA GOLF & COUNTRY CLUB and THE HILLS RESTAURANT, your tee time or dinner reservation is literally a hop, jump and a skip away! Directly across the street, OAKLAND HILLS MARINA AND COMMUNITY BOAT RAMP provide access to approximately 25 MILES OF NAVIGABLE CANALS, dockage and benches on the Rotonda River — ideal for cruising, kayaking, or casting a line at sunset. An expansive circular drive provides generous on-site parking, and with additional open PARKING DIRECTLY ACROSS THE STREET so hosting friends, family gatherings, or larger get-togethers is refreshingly easy (or book the clubhouse next door!) Inside, the home is light, bright, and coastal in feel with wood-look plank tile and an open floor plan designed for easy living. A spacious living room anchors the front of the home, welcoming in natural light and marina views. At the center, an updated galley kitchen features STAINLESS STEEL APPLIANCES, SOLID WOOD CABINETRY, and a breakfast bar that overlooks the oversized dining room — a flexible space that could easily transition into an additional sitting area, den, or media lounge depending on your needs. The split bedroom layout offers privacy for owners and guests alike. The primary suite is generously sized with a walk-in closet, ensuite bath, and direct access to the lanai — ideal for morning coffee without an audience. The second bedroom is equally spacious, complete with a mirrored closet and an ensuite bath that functions as a guest bath in a smart Jack-and-Jill design. The large garage provides built-in storage and houses the laundry area, keeping things practical and organized. Out back, the SCREENED LANAI becomes your front-row seat to the course. Quiet, peaceful mornings when play is light. Lively, entertaining views during peak hours. All of it framed by open green space that adds distance between you and the next home — something you’ll appreciate more and more over time. While this location provides an unmatched lifestyle right outside your door, this area also provides immediate access to other greater area taverns, parks, beaches and so much more! Call today to explore it all!
Listing Agent: Alisha Weaver (941-270-0389)
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