2756 SHERIFF WAY, WINTER PARK, FL 32792
Home value
$588,000
$541,000 - $641,000
$3,023/mo
Owner options
$3,023/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,023/mo
Rent Zestimate®
$4,251/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$4,251/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Kasey Hilyard, PLLC 407-488-9879,
PALM CIRCLE REALTY 352-988-4975
Jeff Taulbee, 675960
CHARLES RUTENBERG REALTY ORLANDO

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 173.25 Square Feet
- Dimensions: 16.5x10.5
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 246 Square Feet
- Dimensions: 12x20.5
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 120.75 Square Feet
- Dimensions: 11.5x10.5
Dining room
- Level: First
- Area: 130 Square Feet
- Dimensions: 10x13
Kitchen
- Level: First
- Area: 156 Square Feet
- Dimensions: 13x12
Living room
- Level: First
- Area: 270 Square Feet
- Dimensions: 18x15
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
- Laundry: Washer Hookup
Features
- Ceiling Fan(s)
- Flooring: Tile
- Has fireplace: No
Interior area
- Total structure area: 2,388
- Total interior livable area: 1,812 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: One
- Stories: 1
- Exterior features: Sidewalk
Lot
- Size: 8,758 Square Feet
Details
- Parcel number: 092230942703010
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1965
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Connected
Community & HOA
Community
- Features: Pool
- Pet fee: $0 monthly
- Subdivision: WINTER PARK PINES
HOA
- Has HOA: Yes
- HOA name: Peter Mason
- HOA phone: 407-671-0785
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $325/sqft
- Tax assessed value: $512,270
- Annual tax amount: $5,547
- Date on market: 5/12/2026
- Cumulative days on market: 25 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Paved
Price history
| Date | Event | Price |
|---|---|---|
| 7/8/2026 | Sold | $588,000-1.2%$325/sqft |
Source: | ||
| 7/8/2026 | Contingent | $595,000$328/sqft |
Source: | ||
| 6/7/2026 | Pending sale | $595,000$328/sqft |
Source: | ||
| 6/5/2026 | Price change | $595,000-4.8%$328/sqft |
Source: | ||
| 5/12/2026 | Listed for sale | $625,000+76.1%$345/sqft |
Source: | ||
| 5/17/2018 | Sold | $355,000-2%$196/sqft |
Source: Public Record Report a problem | ||
| 3/13/2018 | Listed for sale | $362,329+24.9%$200/sqft |
Source: ORLANDO HUB REAL ESTATE INC #O5568134 Report a problem | ||
| 2/26/2016 | Sold | $290,000-3.3%$160/sqft |
Source: Stellar MLS #O5403224 Report a problem | ||
| 1/5/2016 | Price change | $299,900-5.6%$166/sqft |
Source: RE/MAX 200 REALTY #O5403224 Report a problem | ||
| 11/9/2015 | Listed for sale | $317,800+11.5%$175/sqft |
Source: RE/MAX 200 REALTY #O5403224 Report a problem | ||
| 8/12/2008 | Listing removed | $285,000$157/sqft |
Source: Owner Report a problem | ||
| 3/12/2008 | Price change | $285,000-5%$157/sqft |
Source: Owner Report a problem | ||
| 11/12/2007 | Listed for sale | $299,900+177.7%$166/sqft |
Source: Owner Report a problem | ||
| 12/28/1998 | Sold | $108,000$60/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $5,297 +7.4% | $346,893 +3% |
| 2023 | $4,932 +4.3% | $336,789 +3.6% |
| 2022 | $4,729 +1.7% | $325,038 +3% |
| 2021 | $4,651 +0.8% | $315,571 +1.4% |
| 2020 | $4,614 +1.2% | $311,214 +2.3% |
| 2019 | $4,562 +21.3% | $304,217 +20.8% |
| 2018 | $3,760 | $251,913 +2.1% |
| 2017 | $3,760 +1.6% | $246,732 +1.1% |
| 2016 | $3,702 -6.5% | $243,945 +20.6% |
| 2015 | $3,959 +11.4% | $202,319 +16% |
| 2014 | $3,553 +22.7% | $174,427 +16.4% |
| 2013 | $2,896 +0.2% | $149,881 +1.1% |
| 2012 | $2,890 -11.3% | $148,305 -12.1% |
| 2011 | $3,259 -3.9% | $168,658 -7.4% |
| 2010 | $3,392 | $182,083 -4.1% |
| 2009 | -- | $189,817 -10.8% |
| 2008 | $3,750 +108.6% | $212,844 -2.6% |
| 2007 | $1,798 -5.4% | $218,511 +3.6% |
| 2006 | $1,900 +1.7% | $210,875 +18.6% |
| 2005 | $1,868 +4.9% | $177,781 +11% |
| 2004 | $1,781 +0.7% | $160,152 +1.4% |
| 2003 | $1,767 +2.8% | $157,999 +18.8% |
| 2002 | $1,720 -0.6% | $133,029 +7.2% |
| 2001 | $1,731 +2.5% | $124,083 +20.1% |
| 2000 | $1,688 | $103,279 |
Neighborhood: 32792
Nearby homes
- $461,5004 bd2 ba1.6k sqft2764 Sheriff Way, Winter Park, FL 32792Off Market
- $483,4004 bd2 ba1.7k sqft2757 Cady Way, Winter Park, FL 32792Off Market
- $475,7004 bd2 ba2k sqft2765 Cady Way, Winter Park, FL 32792Off Market

- $475,8004 bd2 ba1.7k sqft2772 Sheriff Way, Winter Park, FL 32792Off Market

- $516,1003 bd2 ba1.7k sqft2755 Sheriff Way, Winter Park, FL 32792Off Market
- $595,0004 bd3 ba1.7k sqft337 Gilbert Rd, Winter Park, FL 32792Off Market
- $476,4003 bd2 ba1.6k sqft329 Gilbert Rd, Winter Park, FL 32792Off Market
- $511,0004 bd2 ba1.7k sqft2763 Sheriff Way, Winter Park, FL 32792Off Market
Nearby schools
GreatSchools rating
- 4/10Aloma Elementary SchoolGrades: PK-5Distance: 0.5 mi
- 7/10Glenridge Middle SchoolGrades: 6-8Distance: 1.7 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 0.8 mi
Schools provided by the listing agent
- Elementary: Aloma Elem
- Middle: Glenridge Middle
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Get a cash offer in 3 minutes
- Florida
- Orange County
- Winter Park
- 32792
- 2756 SHERIFF WAY