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$625,000 Just Listed
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Property Description
Welcome to your beautifully updated slice of the Florida Dream here in Winter Park! Perfectly positioned on a desirable corner lot, this thoughtfully renovated home blends modern design, comfort, and functionality - minutes away from Advent Health, Park Avenue, and Schools! From the moment you step inside, you'll notice the extensive tile flooring, upgraded lighting, and stylish finishes throughout. The heart of the home is the stunning RENOVATED KITCHEN featuring QUARTZ countertops, rich NAVY cabinetry, stainless steel appliances, and a gorgeous wine & coffee bar complete with a built-in WINE FRIDGE-perfect for entertaining or slow Florida mornings at home. Need space to work or unwind? The dedicated OFFICE with MODERN BARN DOORS creates the ideal work-from-home setup, while the additional BONUS ROOM offers endless flexibility as a playroom, reading retreat, media space, or hobby room. Down the hall, the spacious and serene Primary Suite invites you to unwind in the renovated, spa-inspired rain showerhead for a relaxing start or finish to your day. The 2nd bedroom has been dubbed the "Hotel Room" by guests because of its larger size and additional sitting area. This space is perfect for MULTIGENERATIONAL LIVING, whether they are coming home for the summer, guests visiting Central Florida on vacation, or extended family needing a space of their own! The 3rd bedroom is across the hall from the Primary and features laminate flooring, so you truly have 3 dedicated bedrooms PLUS an office! Practical upgrades set this home apart from others in the community, including CUSTOM BLINDS Throughout & 5 1/4 INCH BASEBOARDS in the main living areas, an indoor, heated & cooled LAUNDRY ROOM, Replaced A/C (Inside 2020, Outside 2019), NEW ROOF (2022), PVC REPIPE (2018), NEW SEWER, NEWLY FENCED BACKYARD (2022), WIFI Garage Opener (2020)a storage shed, and a NEW (2021) COVERED & SCREENED LANAI with waterproof and weatherproof interlocking flooring, designed for year-round indoor/outdoor living enjoyment. This move-in-ready abode delivers the perfect balance of style and everyday living! Whether you're hosting friends, working remotely, or simply enjoying the Florida lifestyle, this remarkable gem is located blocks away from Cady Way Trail and Ward Park, and just minutes from the award-winning restaurants on Park Avenue, and in the Baldwin Park & Mills50 shopping districts! Don't sleep on this one, call and schedule your private showing today!
Full Property Details
Full Property Details for 2756 Sheriff Way
General
- Price: $625,000
- Taxes: $5,547 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6402570
- Updated: 5/12/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: No Minimum
Interior
- Number of Rooms: 6
- Interior Features: Ceiling Fan(s)
- Appliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Tile
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Washer Hookup
Exterior
- Exterior Features: Sidewalk
Parking
- Garage: Yes
- Attached garage: Yes
- Garage 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 I-4 Northbound, take W. Fairbanks Ave Exit into Winter Park (FL426) Turns into Aloma Ave. Turn Right onto N. Ranger Blvd, Right onto Cady Way, Right onto Gilbert Rd. and home will be on your Right. Corner of Sheriff Way and Gilbert Ave.
- 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
- Pet Restrictions: Buyer/Buyer's Agent to verify all pet restrictions with local government.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Cable TV Available, Electricity Connected
Structural Information
- Exterior Const.: Block
- Roof: Shingle
- Stories/Levels: One
- Square Feet: 1,812
- Sq. Ft. Source: Public Records
- Year Built: 1965
Lot Features
- Lot Size (Acres): 0.2
- Lot Size (Sq. Ft.): 8,758
- Lot Size: 8758
- Street/Road Desc.: Paved
Financial Considerations
- Tax Amount: $5,547
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: WINTER PARK PINES UNIT FOUR Z/55 LOT 1 BLK C
- Flood Zone Info: X
- APN: 92230942703010
- Property ID: 92230942703010
- Block/Lot/Section: C
Listed by Palm Circle Realty
Get Pre-Approved Today
Schools
Schools serving 2756 Sheriff Way
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Aloma Elementary School 2949 Scarlet Road, Winter Park, FL 32792 | K-5 | 0.5 mi |
Glenridge Middle School 2900 Upper Park Road, Orlando, FL 32814 | 6-8 | 1.7 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 0.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 2756 Sheriff Way
Date
Details
Price
Change
Source
5/12/2026
Listed
$625,000
76.06%
MLS
4/30/2018
Sold
$355,000
—
Public Record
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
Tax History for 2756 Sheriff Way
Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,547
5%
$366,591
6%
2024
$5,297
7%
$346,893
3%
2023
$4,932
6%
$336,789
7%
2021
$4,651
-2%
$315,571
-3%
2022
$4,729
2%
$325,038
4%
2021
$4,651
2%
$311,214
2%
2019
$4,562
21%
$304,217
21%
2018
$3,760
2%
$251,913
2%
2017
$3,702
-6%
$246,732
1%
2016
$3,959
11%
$243,945
35%
2015
$3,553
9%
$181,356
10%
2014
$3,252
12%
$164,869
10%
2013
$2,896
—
$149,881
—
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
Estimate the Cost for 2756 Sheriff Way
2756 Sheriff Way, Winter Park, FL 32792 (MLS# O6402570) is a Single Family property with 3 bedrooms and 2 full bathrooms. 2756 Sheriff Way is currently listed for $625,000 and was received on May 12, 2026. Want to learn more about 2756 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.

