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$574,900 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1,948 Sq. Ft.
  • Updated 25 minutes ago
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Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two bathrooms (both showers renovated 5/25) perfect for family living or entertaining guests. As you step inside, you'll be welcomed by a spacious living area that effortlessly transitions into the dining space, creating a warm and inviting setting for gatherings and family meals. The kitchen is thoughtfully designed for both functionality and efficiency, ready to cater to all your culinary needs. Additional living areas include a sunroom back porch and a screened-in carport, providing versatile spaces for relaxation or entertainment. The home is perfect for entertaining, with a rear sunroom/porch, pool, offering a personal oasis for unwinding or hosting friends and family. This outdoor retreat is destined to become a favorite spot for relaxation and enjoyment. The 2-car carport with a screen creates another space to entertain. Located just minutes from Cady Way Trail, Ward Park, Cady Way Community Pool, Lake Baldwin Dog Park, Winter Park Pines Golf Club, and the iconic Park Avenue, this home is perfectly positioned for both convenience and leisure.

Full Property Details for 2814 Sheriff Way

General

  • Price: $574,900
  • Taxes: $7,417 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6383098
  • Updated: Today (3/4/2026)
  • Added to Site: Today

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 9
  • Interior Features: Ceiling Fan(s), Primary Bedroom Main Floor
  • Fireplace: Yes
  • Fireplace(s): Family Room
  • Appliances: Disposal, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: In Garage

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite

Exterior

  • Exterior Features: Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Enclosed, Rear Porch, Screened
  • Porch/Patio/Deck: Enclosed, Rear Porch, Screened

Parking

  • Carports: Yes
  • Carport: 2
  • Carport Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Orange
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: WINTER PARK PINES
  • Driving Directions: From the intersection of Aloma Ave and Ranger Blvd head south on Ranger. Continue .64 miles to Ranger and Sheriff Way. Turn right on Sheriff Way. Property is .12 miles down on the left.
  • Direction Faces: North

School Information

  • Elementary School: Aloma Elem
  • Middle School: Glenridge Middle
  • High School: Winter Park High

Community

  • Community Name: 32792 - Winter Park/Aloma

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: None
  • Utility Description: Cable TV Available, Electricity Connected, Sewer Connected

Structural Information

  • Architectural Info: Florida
  • Architectural Style: Florida
  • Exterior Const.: Block
  • Roof: Shingle
  • Stories/Levels: One
  • Square Feet: 1,948
  • Sq. Ft. Source: Public Records
  • Year Built: 1965

Lot Features

  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,797
  • Lot Size: 7797
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Tax Amount: $7,417.27
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTER PARK PINES UNIT FOUR Z/55 LOT 5 BLK C
  • Flood Zone Info: X
  • APN: 92230942703050
  • Property ID: 92230942703050
  • Block/Lot/Section: C

Listed by Corcoran Premier Realty

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Listing agent

— 2814 Sheriff Way —

  • Corcoran Premier 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 2814 Sheriff Way

School District:Orange County School District
NameGradesDistance
Aloma Elementary School
2949 Scarlet Road, Winter Park, FL 32792
K-50.4 mi
Glenridge Middle School
2900 Upper Park Road, Orlando, FL 32814
6-81.8 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-120.9 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 2814 Sheriff Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/04/2026
Listed
$574,900
51.29%
MLS
7/15/2021
Sold
$380,000
—
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 2814 Sheriff Way

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,417
—
$463,250
2%
2024
$7,417
10%
$454,665
2%
2023
$6,713
253%
$445,388
214%
2021
$1,902
-67%
$141,711
-60%
2022
$5,787
204%
$353,610
153%
2021
$1,902
3%
$139,754
2%
2019
$1,845
1%
$136,612
2%
2018
$1,826
2%
$134,065
2%
2017
$1,786
2%
$131,308
2%
2016
$1,757
-2%
$128,607
1%
2015
$1,785
-2%
$127,713
1%
2014
$1,827
2%
$126,699
1%
2013
$1,788
—
$124,827
—
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.

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NMLS#: 1598647

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Listed by Corcoran Premier Realty

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2814 Sheriff Way, Winter Park, FL 32792 (MLS# O6383098) is a Single Family property with 4 bedrooms and 2 full bathrooms. 2814 Sheriff Way is currently listed for $574,900 and was received on March 04, 2026. Want to learn more about 2814 Sheriff Way? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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