Location: Rotonda West Oakland Hills, Rotonda West
Do Not Show Listings
271 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$379,900199 Days on yellowkey MLS ID: D6144771
REDUCED by $20,000 (5.0%) on 05/11/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1599 Built: 2010Monthly Fee: $32 Tax: $4,178 (2024)Community: Rotonda West Oakland HillsSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,178
Elementary School: Vineland Elementary
High School: Lemon Bay High
Tax Year: 2024
Middle School: L.A. Ainger Middle
Remarks: Pride of Ownership is what you will see with this Peaceful Retreat! This 3 bedroom 2 bath home with a bright and cheerful open floorplan is in mint, move-in condition. The interior has been recently repainted, updated flooring and spotless throughout. Beautifully landscaped, this home has fantastic curb appeal in the front and a park-like, private retreat in the back with a large patio, hot tub and firepit. Behind this home is a nature preserve so you will always have the privacy - nothing will be built behind you. The well planned kitchen includes wood cabinetry and stainless steel appliances with a 9 ' breakfast bar for those quick meals. A cozy dinette at the end of the kitchen looks out over the backyard beauty. The split floorplan has the spacious master bedroom with en-site bathroom and walk in closet on one side of the home with the guest quarters on the other Two pleasant bedrooms and full bath complement the guest side of the home. The laundry room with newer washer and dryer is next to the kitchen and a large 2 car garage. BONUS: Full building lot is included with this property. Extra space between you and your neighbor! The roof was new in 2022, refrigerator, dishwasher, washer and dryer are new, hot water tank is 3 years old and the garage door opener is 2 years old. The A/C has been regularly serviced. This property never lost power through all three storms and had no storm damage. This home is a gem! A short drive to five beaches, shopping, medical care, schools, and great restaurants! You are going to love this property!
Listing is courtesy of: BRETT BARBER & COMPANY REAL ES (941-474-7121)
Listing Agent: Andrea Barber (941-270-6052)
52 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$259,90011 Days on yellowkey MLS ID: O6410119
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1055 Built: 1973Monthly Fee: $190 Tax: $3,528 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$3,528
Tax Year: 2025
Remarks: Live your best life at this WATERFRONT home in the highly sought after ROTONDA WEST community! This 2-BEDROOM, 2 BATH home is a true hidden gem, nestled along the tranquil canals in Rotonda West! Enjoy 5 GOLF COURSES, BROADMOOR PARK, tons of walking trails & 26 miles of picturesque canals! This is the place to be with many lakes, ponds and lots of wildlife! Just a short drive south to world class BOATING & FISHING in Boca Grande & Englewood! 9.1 miles to MANASOTA BEACHES! This waterfront home includes a NEW ROOF installed in 2021 & HURRICANE IMPACT RATED WINDOWS ensuring peace of mind for years to come! A covered screened patio entrance with a frosted glass door leads into a charming open floor plan with MANY UPDATES THROUGHOUT! Living/Dining combo with tile flooring creates a bright & airy coastal living space! Sliding doors lead to a screened patio (21 x 10) with beautiful views of the waterfront canal! You'll love the UPGRADED KITCHEN, featuring STAINLESS-STEEL APPLIANCES, shaker style cabinets & the DYNAMITE countertops & backsplash! Two comfortably sized bedrooms with the primary bedroom featuring a nice WALK-IN CLOSET. The primary bathroom includes a single cabinet vanity & WALK-IN SHOWER. The attached 2-CAR GARAGE offers ample storage space including built-in shelving & a second bathroom with shower! The spacious backyard would be a great spot for adding your own private pool or you could even add a dock to park a pontoon boat for cruising the canals! Enjoy a variety of fabulous & unique restaurants & great SHOPPING along Route 776! This is the perfect route to find all the desirable destinations along the Gulf! Enjoy soaking up the sun on the gulf shores of Manasota Beach known for shelling & shark teeth hunting! If you love Major League Baseball attending a spring training game is always a great time just 30 minutes away! Live your best life at Florida's hidden gem on the Southwest Gulf Coast~ Rotonda West! Call now to schedule your private tour today!
Listing is courtesy of: FIVE STAR REAL ESTATE OF FL (616-791-1500)
Listing Agent: Gerald Buck (231-690-0565)
231 CADDY RD, ROTONDA WEST, FL 33947
$324,50057 Days on yellowkey MLS ID: C7524452
REDUCED by $2,700 (0.8%) on 05/28/2026
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
Elementary School: None
High School: None
Middle School: None
Remarks: Sold TURNKEY, or blank slate for your personalization. WATERFRONT and Well BELOW MARKET VALUE!!! Welcome to this spacious 4-bedroom pool home located in the active golf course community of Rotonda West. Enjoy the best of Southwest Florida living in this tastefully curated home that comes ready for immediate income production, full time enjoyment, or a perfect seasonal retreat. Whether you're golfing at one of the 5 community courses or spending the day at the beautiful nearby parks or Gulf beaches, you will find a dreamy Florida day at your doorstep. Relax or entertain on the expansive, pool deck overlooking a serene freshwater canal. The pool is heated for year-round usage and enjoyment. The rear yard is fenced and ready for your furry guests. A thoughtfully designed split floor plan of 2/2 bedrooms offers generous living space and privacy. The fully furnished set up for the comfortable occupancy of up to 10 occupants. Guests will love the private pool bedroom with sliding glass doors leading directly to the pool deck lounge area. This pool bedroom offers stunning water views and a true retreat-like feel. Recent updates provide peace of mind, including a 2020 HVAC system, 2021 roof, 2022 electrical panel, 2023 Low Maintenance Fiberglass Pool, 2024 Pool Heater and 2025 Pool Motor. The Rotonda West community also features a private storage area for RVs, boats, and other recreational vehicles. Community is very scenic known for its quiet streets, multiple golf courses, parks, walking trails, and family-friendly amenities including playgrounds, bike paths, and nearby tennis and recreational facilities—making it a great fit for both relaxation and active lifestyles. Opportunity awaits, in this proven income producing home so don't hesitate.
Listing is courtesy of: R & R CONSULTING LLC (941-916-1662)
Listing Agent: Ruth Keiling (941-916-1662)
60 ROTONDA CIR, ROTONDA WEST, FL 33947
$246,500107 Days on yellowkey MLS ID: D6146148
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1231 Built: 1980Monthly Fee: $16 Tax: $3,462 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$3,462
Remarks: One or more photo(s) has been virtually staged. Welcome to your next chapter in Rotonda West's PREMIER GOLFING COMMUNITY! This 3-bedroom, 2-bathroom home with a two-car garage sits on over a QUARTER ACRE with direct golf course views, offering an unbeatable combination of location, lifestyle, and value. Step inside to discover recently updated luxury vinyl plank in the living/dining areas and tile flooring throughout the rest of the home, complemented by modern recessed lighting. The bright, open kitchen features generous cabinet space and flows seamlessly into the dining area—perfect for daily living and entertaining. The spacious living room opens to an expansive backyard with room to add your dream pool while enjoying front-row views of the fairway. The primary suite provides a private retreat with an en-suite bathroom and walk-in closet. Two adjacent bedrooms are perfect for a growing family, guests or home office! Recent upgrades include a newer roof, AC unit with updated ductwork, and hurricane fabric panels for added protection and peace of mind. Rotonda West offers an exceptional Southwest Florida lifestyle, nestled between Englewood and Port Charlotte with access to five golf courses totaling 99 holes. The community features walking and biking trails, a 165-acre park, tennis and pickleball courts, and a playground with pavilion. Pristine Gulf beaches at Manasota Key and Boca Grande are minutes away, while fishing, boating, and kayaking opportunities abound. Explore charming downtown Punta Gorda or Dearborn Street in Englewood for local shops, restaurants, and farmers markets. Convenient to local and regional airports. Low annual HOA fees and city water/sewer services complete this exceptional opportunity—ideal for investors, first-time buyers, or those seeking a seasonal retreat.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-429-3506)
Listing Agent: Barbara Hamerton, Llc (305-496-4732)
11 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$359,90031 Days 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)
33 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$225,000118 Days on yellowkey MLS ID: D6145987
REDUCED by $9,000 (3.8%) on 05/12/2026
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)
256 CADDY RD, ROTONDA WEST, FL 33947
$329,00087 Days on yellowkey MLS ID: D6146423
0 Days Off yellowkey (back on 5/29/2026)
REDUCED by $5,000 (1.5%) on 05/25/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1820 Built: 1973Monthly Fee: $16 Tax: $2,950 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$2,950
Remarks: Under contract-accepting backup offers. Relaxed Golf Course Living on the 16th Green in Rotonda West! This four bedroom, two bathroom golf course pool home in the Oakland Hills section of Rotonda West offers a light and bright interior, open living spaces, and plenty of room for family and friends. Tropical landscaping welcomes you to the property, highlighted by a beautiful Bismark Palm and a distinctive entry wall. Step through the decorative lead glass front door into a split floor plan that opens to a welcoming formal living room, providing a comfortable space to unwind. The well designed kitchen features wood cabinetry, granite countertops, a tray ceiling, tile backsplash, breakfast bar, and closet pantry. Just off the kitchen is a perfect space for a dining nook, while the fully enclosed Florida room beyond overlooks the pool and includes a convenient pass through from the kitchen along with double French doors that open to the lanai and pool area. The ensuite primary bedroom offers a quiet retreat with two large reach in closets. The primary bathroom features a beautifully tiled step in shower, pedestal sink, and a door that leads to a private screened lanai, creating a peaceful outdoor space for reading, relaxing, or enjoying the fresh Florida air. Three additional guest bedrooms each include reach in closets, providing comfortable accommodations for visitors. The recently remodeled guest bathroom includes a solid surface vanity and a fully tiled tub and shower combination, along with a convenient door to the pool area to help keep wet feet off the interior floors. Outdoor living takes center stage on the partially covered and screened lanai, where golf course views create a peaceful backdrop. The PebbleTec deck surrounds the large 15 by 25 pool, offering plenty of room to float in the sunshine or swim laps. Additional updates and upgrades include a 2023 roof, whole house impact windows, a hurricane rated garage door, wood look vinyl and tile flooring throughout, a newer panel box with surge protector, a 2021 air conditioning system, newer gutters, an alarm system, and a Nest thermostat. Located in the golfing community of Oakland Hills within Rotonda West, this deed restricted neighborhood offers activities including golf, tennis, hiking trails, and fishing. The home is also less than ten miles from Englewood Beach where residents can spend the day enjoying the sand and water, dining at local restaurants or tiki bars, or ending the evening with a sunset and several options for live entertainment. From morning coffee overlooking the fairway to afternoons by the pool, this home is ready to be enjoyed at 256 Caddy Road.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-473-8484)
Listing Agent: Carla Stiver, Pa (941-270-1460)
9 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$249,900572 Days on yellowkey MLS ID: D6138925
REDUCED by $10,100 (3.9%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1388 Built: 1972Monthly Fee: $16 Tax: $1,485 (2023)Community: Rotonda West Oakland HillsSingle Family
Taxes:$1,485
Tax Year: 2023
Remarks: Peaceful pool home with preserve view! Nestled in a serene setting, this delightful 2-bedroom, 2-bathroom home offers the best of Florida living with lush preserve views and a tranquil backdrop. Located in desirable Rotonda West, this single-family gem includes a spacious open floor plan, a one-car garage, and a private pool—perfect for relaxation or entertaining. As you step inside, you're greeted by an airy living space with abundant natural light that highlights the beautiful tile flooring. The fully equipped kitchen, with plenty of counter space and storage, opens to the dining and living areas, making it ideal for both everyday living and gatherings. The open layout offers privacy, with the spacious primary suite featuring an en-suite bath and large closet, while the second bedroom is perfect for guests or a home office. The screened-in lanai invites you to enjoy Florida’s year-round sunshine, complete with a sparkling pool overlooking the pristine, protected preserve—a natural extension of your backyard that promises peace, quiet, and visits from local wildlife. Situated minutes from golfing, beautiful Gulf beaches, shopping, and dining, this home captures the relaxed Rotonda West lifestyle. Don’t miss this rare opportunity to own a private, peaceful pool home in a stunning location!
Listing Agent: Alex Bowermaster (513-275-2396)
31 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$222,00068 Days on yellowkey MLS ID: D6146511
1 Days Off yellowkey (back on 5/24/2026)
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: Under contract-accepting backup offers. 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 ceiling fans and window blinds; 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. In addition, a brand new electrical panel has just been installed, with all new breakers, surge protection, and new grounding system. 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)
55 ROTONDA CIR, ROTONDA WEST, FL 33947
$599,00036 Days on yellowkey MLS ID: N6144131
REDUCED by $46,000 (7.1%) on 05/20/2026
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: Discover modern Florida waterfront living at its finest in this stunning brand-new 2026-built 4-bedroom, 2-bathroom pool home with 2-car garage, perfectly situated on a freshwater canal in the desirable Oakland Hills section of Rotonda West! Boasting 1,862 sq ft of thoughtfully designed living space on a generous 10,000 sq ft lot with 80 feet of direct canal frontage, this turnkey new-construction residence offers exceptional quality, contemporary elegance and seamless indoor-outdoor living. Step inside to an open-concept layout with porcelain tile flooring throughout, soaring tray ceilings, and abundant natural light. The gourmet kitchen shines with quartz countertops, a large island, stainless steel appliances, and soft-close solid wood cabinetry—ideal for effortless entertaining. A split-bedroom floor plan ensures privacy, while dramatic corner slide-away glass doors connect the main living areas directly to the expansive screened pool and large covered lanai, creating the perfect setting for year-round outdoor enjoyment with serene canal views. Additional highlights include ceiling fans, central air conditioning and heating, inside laundry room, and a 2-car attached garage. Outside, relax by your private screened in-ground pool or entertain on the spacious lanai overlooking the water. Community boat docks and ramp are less than half a mile away, giving easy access to Rotonda West’s vast navigable canal network for fishing, kayaking, or boating adventures. Rotonda West delivers an unparalleled Southwest Florida lifestyle with low HOA fees of just $16/month, multiple golf courses (including nearby The Hills Golf Course), parks, bike trails, pickleball and tennis courts, and a true sense of community. Enjoy convenient access to world-class Gulf beaches, shopping, dining, and top-rated schools (Vineland Elementary, L.A. Ainger Middle, Lemon Bay High). Don’t miss your chance to own a brand-new canal-front pool home in one of Charlotte County’s most sought-after established communities. Schedule your private showing today and experience everything this exceptional property has to offer!
Listing is courtesy of: EXCELLENT CHOICE REALTY, LLC (941-412-6477)
Listing Agent: Alex Solovyev (941-408-4400)
124 CADDY RD, ROTONDA WEST, FL 33947
$296,000211 Days on yellowkey MLS ID: D6144573
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1839 Built: 1973Monthly Fee: $7 Tax: $2,847 (2024)Community: Rotonda West Oakland HillsSingle Family
Taxes:$2,847
Remarks: Welcome to paradise located inside the circle of Rotonda West Community, wether you want to be a owner or a investor, this fully furnished, remodeled 4 bed, 2 bath home sits on oversized lote 9,600 sq ft with 1839 Sq ft of living area, new roof, new AC with a high-efficient thermostat, impact windows and doors, dryer and washer, stainless steel kitchen, dishwasher, microwave, electric range with self-cleaning oven, double doors refrigerator, double sink, ceiling fan in all rooms, primary bedroom with walk-in closet, 1 car garage with automatic garage door opener, big paved driveway, sprinkler system, well, smoke detector, screened terrace with lake view, landscaped backyard, close proximity to Manasota Key, low HOA, no CDD.
Listing is courtesy of: LANDMARKS INTERNATIONAL REALTY, INC. (305-310-6961)
Listing Agent: Amed Chavez Santo Tomas (786-405-4054)
22 OAKLAND HILLS CT, ROTONDA WEST, FL 33947
$234,99999 Days on yellowkey MLS ID: C7522427
0 Days Off yellowkey (back on 5/19/2026)
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)
240 CADDY RD, ROTONDA WEST, FL 33947
$599,90021 Days on yellowkey MLS ID: A4693678
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2145 Built: 2021Monthly Fee: $16 Tax: $7,026 (2025)Community: Rotonda West Oakland HillsSingle Family
Taxes:$7,026
Remarks: Welcome To your Golf Course Facing Dream Home with an Oversized Pool. This 4 Bedroom 2 Bath Rotonda West Home is Perfect for any Golf enthusiast. The home is located on a nice quiet street with amazing views. This is one you truly must see to appreciate. The home does have a stage 2/ 240 Volt Auto Charger in the garage..
Listing is courtesy of: REALTY ONE GROUP SUNSHINE (727-325-5843)
Listing Agent: Arno Isaian (941-979-1147)
242 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$249,999133 Days on yellowkey MLS ID: C7520633
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1387 Built: 1986Monthly Fee: $16 Tax: $2,366 (2025)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$2,366
Remarks: From the moment you arrive at 242 Annapolis Lane, you’ll feel the soothing natural ambiance that makes Rotonda West so special. Sunshine dances across the façade, welcoming you home, while the peaceful freshwater canal in your backyard quietly calls to the angler in you. Cast a line, sip your morning coffee, or simply watch the water shimmer—this is Florida living at its finest. Step outside to your private oasis, where two majestic mango trees provide shade and seasonal treats. The stamped concrete patio is the perfect place to unwind, entertain, or soak up the coastal breeze. With a fully fenced backyard, your fur babies and little ones can roam freely while you relax knowing they’re safe. Inside, nearly 1,400 square feet of thoughtfully designed living space unfolds. The split-bedroom floor plan offers privacy, with both bedrooms featuring their own en-suite bathrooms. You’ll love the no-carpet design, easy-care flooring, and the bonus den/office/craft room—perfect for hobbies, remote work, or quiet retreats. The kitchen is conveniently located near the laundry room and garage, making grocery days a breeze, and a charming nook beneath the window invites you to create a cozy bistro corner or workspace overlooking the backyard. This home has been lovingly maintained with major updates already done for you: a new roof in 2023, A/C in 2022, new windows in 2021, full repiping in 2013, and a brand-new hot water heater in 2025. Sitting high at 10.2 feet above sea level, the homeowner reports no flooding during recent hurricanes—offering priceless peace of mind. Can be purchased *TURNKEY FURNISHED* for $5,000 (with a few exclusions) outside of the contract! On city water and sewer, and includes a two-car garage. Rotonda West’s low annual HOA of just $190 keeps community standards high without breaking the bank. Need space for your toys? There’s community storage available for boats or RVs. Golfers will love having five public golf courses right in the neighborhood, and beach lovers will appreciate being just 20 minutes from Manasota Key and Boca Grande’s pristine shores. This is more than a home—it’s a lifestyle. Schedule your showing today and start living the Florida dream you’ve been waiting for!
Listing Agent: Tawnya Hile (941-467-2349)
208 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$439,900128 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
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)
2 GOLFVIEW RD, ROTONDA WEST, FL 33947
$350,00061 Days on yellowkey MLS ID: D6146900
REDUCED by $15,000 (4.1%) on 05/14/2026
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 well maintained Rotonda West Oakland Hills home is situated on a large corner lot with a majestic Oak and some really nice features and upgrades you don't see from the outside. Once you enter the home you are welcomed with a Large Open Living Room/Kitchen/Dining Room area updated in 2019 including floors, granite counter tops, updated cabinets and appliances make you feel right at home in this kitchen. Making your way back to the master suite is the secondary suite with its own bathroom. As you enter the master bedroom sitting area the space really starts to open up as you make your way into the master suite. The first thing you notice is the master bathroom updated in 2021 with soaking tub and shower surrounded by glass and views of your very own private courtyard. If you're looking for the most peaceful area in the house then you found it. The master bedroom shares the pool area and private courtyard with 2 large sliders. If hanging out at the pool with a cocktail is your thing then grab a seat or jump right in, 365 days a year because it's heated which was replaced in 2019 and a new pump in 2025 ! ! The shingle roof was replaced in 2022. New Impact Rated Dining Room Slider in 2023. New soffit & fascia in 2024 along with new gutters in 2025. The current owners took care of most everything leaving you with the responsibility of enjoying it. Schedule your showing today and start enjoying life by the pool in beautiful sunny Florida.
Listing is courtesy of: THE SUNNYBROOK REALTY LLC (941-474-8000)
Listing Agent: Tim Bronson (941-661-5591)
12 GOLFVIEW CT, ROTONDA WEST, FL 33947
$289,90052 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)
202 CADDY RD, ROTONDA WEST, FL 33947
$359,90066 Days on yellowkey MLS ID: D6146788
0 Days Off yellowkey (back on 5/14/2026)
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: Under contract-accepting backup offers. $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)
75 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$262,000749 Days on yellowkey MLS ID: C7492843
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1455 Built: 1974Monthly Fee: $16 Tax: $3,789 (2023)Community: Rotonda West Oakland HillsSpa: NoSingle Family
Taxes:$3,789
Remarks: Great house in Rotonda West! Almost 1500 sqft of a full renovated 2 bed 2 bath house, with new roof! new kitchen, new floor, painted inside and outside. Beautiful pool in a huge screened lanai. Huge open floorplan. Close to beaches, shopping, restaurant. Ready to move in!
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Federico Burger (201-210-9949)
18 ANNAPOLIS LN, ROTONDA WEST, FL 33947
$350,00049 Days on yellowkey MLS ID: C7524184
REDUCED by $4,000 (1.1%) on 05/14/2026
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
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)
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