Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$265,000

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,190 Sq. Ft.
See This Home
Save This Home
See This Home
Save This Home
New on market! 2/2/2 private villa in a quiet community. Lots of updates and well maintained. New ceiling fans, lighting, showers and more. Bar in kitchen for entertaining. Large 2 car garage with door opener. Accordian hurricane shutters. Enjoy the use of a nice community center, social activities, social activities director, walking trail, library, heated pool, fitness room, billiards room, boccie ball, pickleball, shuffleboard and more. Heritage Oak Park is well known for being a friendly, active community with beautiful large trees. Very private setting. Across street from YMCA and Franz Ross park. With a walk trail, tennis courts, pickleball and kids playground. 10 mins from shopping and 30 mins to charlotte harbor.

Full Property Details for 1448 Winding Oak Dr

General

  • Price: $265,000
  • HOA FEE: $217/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $5,997 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: R4910656
  • Updated: 2/3/2026
  • Added to Site: 20 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 6
  • Interior Features: Ceiling Fan(s), Open Floorplan, Thermostat, Window Treatments
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Negotiable
  • Flooring: Carpet, Ceramic Tile

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: In Garage

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Gated, Maintenance, Pool

Exterior

  • Exterior Features: Sidewalk
  • Deck/Patio: Covered, Enclosed, Front Porch
  • Porch/Patio/Deck: Covered, Enclosed, Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 33948 - Port Charlotte
  • County: Charlotte
  • Development Name: 33948 - Port Charlotte
  • Subdivision: HERITAGE OAK PARK 04
  • Driving Directions: Take Hwy 41, turn on Forrest Nelson Blvd, turn west on Quesada Ave, turn on Heritage Oak Blvd, turn on Winding Oak Dr, turn right on last driveway, unit is the last garage, walk on the sidewalk to the front door.
  • Direction Faces: North

School Information

  • Elementary School: Liberty Elementary
  • Middle School: Murdock Middle
  • High School: Port Charlotte High

Community

  • Community Name: 33948 - Port Charlotte
  • Community Features: Clubhouse, Fitness Center, Gated Community - No Guard, Pool
  • Optional Amenities: Clubhouse, Fitness Center, Gated, Maintenance, Pool
  • Association: Yes
  • Assoc. Name: Manager
  • Assoc. Fees Include: Maintenance Grounds, Pool Maintenance, Sewer, Trash
  • Number of Pets: 2
  • Pet Restrictions: 1 dog, 1 cat, see pet attachment for more

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available, Cable Connected, Electricity Available, Electricity Connected

Structural Information

  • Architectural Info: Other
  • Architectural Style: Other
  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,190
  • Sq. Ft. Source: Public Records
  • Year Built: 2003

Lot Features

  • Property View: Park/Greenbelt
  • Lot Size (Acres): 0.24
  • Lot Size (Sq. Ft.): 10,662
  • Lot Size: 10662
  • Frontage: Street Paved
  • Street/Road Desc.: Paved

Financial Considerations

  • Association Fee: $651
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $5,997.87
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Condominium
  • Special Conditions: None
  • Legal Description: HOP 04R 0000 0I27 HERITAGE OAK PARK 4TH REPL LT I-27 2394/1419 AFF3140/542 PR07-534-ALS 3153/1715 3173/983 PRD3173/986 3533/1602 3533/1603 3365979 DC3365973-LJW 3365979
  • Flood Zone Info: X500
  • APN: 402208253033
  • Property ID: 402208253033

Listed by Easy Realty

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 1448 Winding Oak Dr —

  • Easy Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1448 Winding Oak Dr

School District:Charlotte County School District
NameGradesDistance
Liberty Elementary School, Port Charlotte, FL
370 Atwater Street, Port Charlotte, FL 33954
PK-51.3 mi
Murdock Middle School
17325 Mariner Way, Port Charlotte, FL 33948
6-82.1 mi
Port Charlotte High School
18200 Cochran Boulevard, Port Charlotte, FL 33948
9-121.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1448 Winding Oak Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/02/2026
Listed
$265,000
23.26%
MLS
2/02/2024
Sold
$215,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1448 Winding Oak Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,339
-45%
$221,354
—
2024
$6,093
2%
$220,548
10%
2023
$5,972
14%
$200,498
5%
2022
$5,234
6%
$191,663
16%
2021
$4,956
—
$165,701
5%
2021
$4,956
17%
$158,547
11%
2018
$4,250
5%
$142,471
6%
2017
$4,058
-12%
$134,906
-12%
2019
$4,616
18%
$152,630
19%
2016
$3,910
4%
$128,235
13%
2015
$3,749
9%
$113,960
10%
2014
$3,447
2%
$103,600
4%
2013
$3,380
—
$99,765
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1448 Winding Oak Dr

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Easy Realty

Similar Properties near 1448 Winding Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

20347 Mt Prospect Ave, Port Charlotte, FL 33952 - Photo 1
$265,000

20347 Mt Prospect Ave  Port Charlotte, FL 33952

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,190
    Sq. Ft.
Listed by Marina Park Realty Llc
13440 SW Pembroke Cir N, Lake Suzy, FL 34269 - Photo 1
$265,000

13440 SW Pembroke Cir N  Lake Suzy, FL 34269

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,449
    Sq. Ft.
Listed by Kw Peace River Partners
838 Springview Ave NW, Port Charlotte, FL 33948 - Photo 1
$267,000

838 Springview Ave NW  Port Charlotte, FL 33948

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,133
    Sq. Ft.
Listed by Century 21 Tropical Breeze
2113 Barksdale St, Port Charlotte, FL 33948 - Photo 1
$269,900

2113 Barksdale St  Port Charlotte, FL 33948

  • Single Family
  • Active
  • 2
    Beds
  • 2
    Total Baths
  • 1,395
    Sq. Ft.
Listed by Coldwell Banker Sunstar Realty

Just Listed near 1448 Winding Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16768 San Edmundo Rd, Punta Gorda, FL 33955 - Photo 1 Just Listed
$699,999

16768 San Edmundo Rd  Punta Gorda, FL 33955

  • Single Family
  • Active
  • Updated 12 hours ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,469
    Sq. Ft.
Listed by The Forneris Group (239) 945-1414
16768 San Edmundo Rd, Punta Gorda, FL 33955 - Photo 1 Just Listed
$699,900

16768 San Edmundo Rd  Punta Gorda, FL 33955

  • Single Family
  • Active
  • Updated 12 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,469
    Sq. Ft.
Listed by The Forneris Group (239) 945-1414
12253 Green Gulf Blvd, Punta Gorda, FL 33955 - Photo 1 Just Listed
$35,990

12253 Green Gulf Blvd  Punta Gorda, FL 33955

  • Lots/Land
  • Active
  • Updated 5 days ago
  • 0.47
    Acres
Listed by Frank Moore (239) 839-0471
17304 Vagabond Cir, Punta Gorda, FL 33955 - Photo 1 Just Listed
$645,000

17304 Vagabond Cir  Punta Gorda, FL 33955

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,919
    Sq. Ft.
Listed by Christle Arenas (520) 334-0877

Price Reduced near 1448 Winding Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

27 N Manatee Loop, Punta Gorda, FL 33950 - Photo 1 Price Reduced
-$7,500 (-3.75%)
$192,500

27 N Manatee Loop  Punta Gorda, FL 33950

  • Mobile Home
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,104
    Sq. Ft.
Listed by Lisa Spagenski (954) 401-2618
43 Tropicana Dr, Punta Gorda, FL 33950 - Photo 1 Price Reduced
-$100,000 (-9.09%)
$1,000,000

43 Tropicana Dr  Punta Gorda, FL 33950

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 2,114
    Sq. Ft.
Listed by Bradly Linenberg (941) 448-1026
24277 Treasure Island Blvd, Punta Gorda, FL 33955 - Photo 1 Price Reduced
-$19,500 (-3.42%)
$550,000

24277 Treasure Island Blvd  Punta Gorda, FL 33955

  • Single Family
  • Active
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,500
    Sq. Ft.
Listed by Carmen Henderson (407) 538-9216 and Peyton Blanton (407) 462-7891
39970 Little Farm Rd, Punta Gorda, FL 33982 - Photo 1 Price Reduced
-$10,000 (-2.86%)
$339,900

39970 Little Farm Rd  Punta Gorda, FL 33982

  • Lots/Land
  • Active
  • Updated 5 days ago
  • 5
    Acres
Listed by Villa & Company Inc

Recent Sales near 1448 Winding Oak Dr

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1249 White Oak Trail, Port Charlotte, FL 33948 - Photo 1 Sold
$277,500

1249 White Oak Trail  Port Charlotte, FL 33948

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,535
    Sq. Ft.
Listed by Grettel Piquero Dominguez and Carol Easton
Sold by Carol Easton
1260 White Oak Trail, Port Charlotte, FL 33948 - Photo 1 Sold
$289,500

1260 White Oak Trail  Port Charlotte, FL 33948

  • Single Family
  • Closed
  • 3
    Beds
  • 2
    Total Baths
  • 1,561
    Sq. Ft.
Listed by Re/Max Harbor Realty
Sold by Atlantic Realty & Investments
1318 Red Oak Ln, Port Charlotte, FL 33948 - Photo 1 Sold
$279,200

1318 Red Oak Ln  Port Charlotte, FL 33948

  • Single Family
  • Closed
  • 2
    Beds
  • 2
    Total Baths
  • 1,191
    Sq. Ft.
Listed and Sold by Coldwell Banker Sunstar Realty
1256 Green Oak Trail, Port Charlotte, FL 33948 - Photo 1 Sold
$265,000

1256 Green Oak Trail  Port Charlotte, FL 33948

  • Single Family
  • Closed
  • Updated 1 day ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,364
    Sq. Ft.
Listed and Sold by Coldwell Banker Sunstar Realty

1448 Winding Oak Drive, Port Charlotte, FL 33948 (MLS# R4910656) is a Single Family property with 2 bedrooms and 2 full bathrooms. 1448 Winding Oak Drive is currently listed for $265,000 and was received on February 02, 2026. Want to learn more about 1448 Winding Oak Drive? Do you have questions about finding other Single Family real estate for sale in Port Charlotte? You can browse all Port Charlotte real estate or contact a Coldwell Banker agent to request more information.

Tour this property