Short Sale. Welcome to 50 Caddy Road in the desirable Oakland Hills section of Rotonda West! This beautifully maintained 3-bedroom, 2-bath pool home offers the perfect blend of comfort, style, and Florida living. Situated on the golf course with tranquil water views, the property features an expansive screened lanai, heated saltwater pool and spa, and a spacious split-bedroom floor plan designed for both relaxation and entertaining. The updated kitchen boasts stainless steel appliances, an island, and ample cabinetry, while multiple sliding glass doors seamlessly connect indoor and outdoor living spaces. A circular driveway, oversized side-entry garage, and mature landscaping enhance the home's curb appeal. Located near championship golf courses, beaches, boating, fishing, dining, and shopping, this home offers an exceptional opportunity to enjoy the Southwest Florida lifestyle.
Oakland Hills, located between Rotonda Circle and Gasparilla Road, is a canal-side and golf-adjacent Rotonda neighborhood with curving streets and wide water views. The neighborhood’s character concentrates around Rotonda Circle, where palms, roundabout traffic, and low-slung plazas set a relaxed, coastal tone. Homes lean toward Florida ranch and contemporary builds, many oriented to docks, screened lanais, and backyard water frontage. The landscape reads as manicured and open, with long sightlines across fairways and canals. Daily rhythms track the water—kayaks, small boats, and evening walks along quiet bends. Nearby greens and clubhouse-style gathering spots give the area a resort-like cadence without feeling busy.
Provided by Walk Score and Local Logic
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Interior features
Ceiling fans
Eat-in kitchen
Open floorplan
Living room/dining room combo
Solid wood cabinets
Bedrooms
3 bedrooms
Bathrooms
2 full bathrooms
Kitchen
Eat-in kitchen layout
Laundry & utility
Laundry in garage
Flooring
Tile flooring
Heating & cooling
Central heating
Central air conditioning
Exterior features
Awning(s)
French doors
Rain gutters
Private heated saltwater gunite pool with screen enclosure (in-ground)
Home design
Single family residence
One story
Southeast-facing
Homestead property
Parking
Attached 2-car garage
Construction
Stucco construction
Concrete and tile roof
Slab foundation
Lot about 0.22 acres (approximately 0 to less than 1/4 acre)
Utilities
Public water
Public sewer
Electricity connected
Water connected
Sewer connected
HOA & community
Part of Rotonda West Association
HOA required; $190 annually (about $15.83 monthly)
Pets allowed
Other
Living area approximately 1,687 (public records)
Roads are asphalt/paved
Electricity and solar
View estimated energy costs and solar savings for this home
Welcome home to the highly sought-after neighborhood of Oakland Hills in Rotonda West. This community includes access to five golf courses operated by Rotonda Golf and Country Club. Thirty miles of picturesque canals wind through the community and endless fishing and boating opportunities for its residents at the Rotonda Marina. Discover this fully furnished eye catching 3-bedroom, 2-bathroom pool home nestled on a quiet street in Oakland Hills Community. With over 2,753 square feet of total space, the home boasts a brand new kitchen with all stainless steel appliances and island, expansive 10' x 45' screened lanai and a heated saltwater pool with a spa, all overlooking the serene 7th hole and pond of the Oakland Hills Golf Course. The split floor plan ensures privacy, with a generous master suite featuring a renovated en-suite bath with dual sinks and a walk-in shower and direct access to the lanai. Enjoy seamless indoor-outdoor living with three sets of double sliders that open from the bedrooms and dining room to the lanai with an inviting and open space, offering picturesque views of the heated saltwater pool and golf course. A circular driveway and two-car side-entry garage add to the home's charm and functionality. Recent updates include new roof 2023, new AC 2024 and new interior paint. Pool pump 2016. Plumbing repipe in 2013. Come experience the coastal lifestyle! Play on 5 championship golf courses, enjoy world-class fishing, dozens of waterfront dining options. Close to Englewood, Manasota, and Boca Grande providing the ultimate coastal lifestyle.
Stellar MLS as Distributed by MLS Grid #C7419441
Oct 15, 2019
Sold
$231,900
$137/sq ft
Aug 29, 2019
Pending
—
Aug 26, 2019
Listed
$214,900
$127/sq ft
Welcome home to this beautiful 3 bedroom, 2 Bathroom, pool home located in deed restricted Golf Course Community of Oakland Hills in Rotonda West. Just minutes from Boca Grande and Manasota Beaches! The home is located on a quiet street, has over 2753 total square feet of space with a super large 10’X45’ screened lanai/Florida room and heated saltwater pool with spa overlooking the manicured Oakland Hills golf course 7th hole and pond. Clean and move in ready. Rotonda West offers five golf courses and is a short drive to Englewood's Manasota Key Beach and Boca Grande world class fishing and beaches. Split floor plan separates the 2 guest bedrooms from the Master suite. Large master has en-suite private bath with walk-in shower and sliders leading to lanai and pool. Three sets of double sliders lead from bedrooms and dining room to lanai/pool and provide in home views of pool and golf course. Home features a circular driveway with two car side-entry garage. Tool shed. Minutes from world class fishing and boating in the Gulf of Mexico with numerous nearby marinas and boat launches. All furnishings are available. A/C 2013, Plumbing re-pipe 2013, Pool 2000, Pool Pump 2017. Come Enjoy Florida Lifestyle!
Stellar MLS as Distributed by MLS Grid #D6105354
May 4, 2019
Listing Removed
—
Mar 10, 2019
Price Changed
*
Feb 15, 2019
Listed
*
Stellar MLS as Distributed by MLS Grid #D5923459
Apr 26, 2018
Listing Removed
—
Apr 26, 2018
Relisted
—
Apr 20, 2018
Listing Removed
—
Mar 2, 2018
Listed
*
Public Records
Nov 4, 2015
Sold
$185,000
$110/sq ft
Stellar MLS as Distributed by MLS Grid #D490642
Sep 13, 2005
Listed
*
Public Records
Feb 18, 1997
Sold
$83,000
$49/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$5,561 (+51.4%)
$33,150 + $261,464
$294,614
2024
$3,673 (+1.4%)
$33,150 + $261,464
$294,614
2023
$3,622 (+2.5%)
2022
$3,534 (+0.5%)
2021
$3,517 (+7.6%)
2020
$3,270 (+8.3%)
$13,175 + $177,747
$190,922
2019
$3,018 (+8.4%)
$13,175 + $177,747
$190,922
2018
$2,785 (+1.5%)
$14,450 + $134,628
$149,078
2017
$2,742 (+7.5%)
$14,450 + $126,047
$140,497
2016
$2,551 (+153.3%)
$14,450 + $110,395
$124,845
2014
$1,007
2013
$1,007 (+2.2%)
2012
$986
Public record
Public record
Zoning
Permits
Beds
3
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
9,599 Sq. Ft.
Year renovated
1984
Finished Sq. Ft.
1,687
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,687
Year built
1973
Style
Single Family Residential
County
Charlotte County
APN
412026106009
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 23, 2026.
RSF5
Residential Single-Family District
The purpose and intent of these districts is to provide for single-family residential dwellings and other uses normally associated therewith. Among RSF-2, RSF-3.5 and RSF-5 districts, there are variations in requirements for lot area, width, and certain yards.
Permitted uses
Include but are not limited to:
Day care facility
Housing-Single unit
Housing-Senior
Communications tower
Housing-Mobile home park
Park & open space
Oct 21, 2024 • Final
Residential electrical
Perform a small kitchen remodel and install a new kitchen island.
Electrical
Kitchen
Sep 11, 2024 • Final
Residential mechanical
Install a complete heating and air conditioning system.
HVAC
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
9/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
4/10 Fire Factor
1% chance of being in a wildfire in next 30 years
10/10 Heat Factor
7 days above 107° expected this year, 28 days in 30 years
10/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Rotonda West, FL • 33947
Average low and high temperatures (°F)
72
50
77
56
81
60
85
65
89
72
91
75
91
77
91
78
90
76
86
70
82
61
77
56
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
94/ 100
Exceptional sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.9 hrs
7.4 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 50 Caddy Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $250,000 and $407,500.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $250K to $408K.