2756 Sheriff Way, FL

$625,000

2756 Sheriff Way

Winter Park, FL 32792

Active
3
Beds
2
Baths
1,812
Sq Ft
0.2
Acres
1965
Built
$345/sqft
🏠Single Family Residence

Property type

🏗️1965

Year built

📐8,758 sqft

Lot size

📊$345

Price / sq ft

🏘️No HOA

HOA dues

📅10

Days on market

🚗2

Garage spaces

🌊X

Flood zone

About this home

**$10,000 BUYER INCENTIVE OFFERED!! This can be used for Closing Costs, Interest Rate Buydown, or Landscaping Credit!** 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!

Estimated monthly payment

Principal & interest$3,160
Property taxes$462
Home insurance (est.)$286

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history10 days on market

  1. Status: Active
    May 12, 2026
  2. Listed$625,000
    May 12, 2026
  3. Price increased$625,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
10
Subdivision
Winter Park Pines
County
Orange
Year built
1965
Living area
1,812 sq ft
Price/sq ft
$345
Building area
2,388 sq ft (Public Records)
Lot size
8,758 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12095C0255F)
Garage
2 spaces
Annual taxes
$5,547 (2025)
Parcel #
09-22-30-9427-03-010
Zoning
R-1A
MLS #
O6402570

Interior Details

Bedrooms
3
Full bathrooms
2
Flooring
Tile
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer, Wine Refrigerator
Interior features
Ceiling Fans(s)
Laundry
Washer Hookup
Stories / Levels
One
Direction faces
North

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
HOA name
Peter Mason
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Buyer/Buyer's Agent to verify all leasing restrictions with local government.

Exterior & Construction

Exterior features
Sidewalk
Construction materials
Block
Roof
Shingle
Foundation
Slab
Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Cable Available, Electricity Connected

Community

Pets allowed
Yes

Schools

ElementaryBAloma ElemGreatSchools ↗
MiddleAGlenridge MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
KitchenFirst13x12
Dining RoomFirst10x13
Living RoomFirst18x15
Primary BedroomFirst16.5x10.5
Bedroom 2First12x20.5
Bedroom 3First11.5x10.5

Listing Details

Listing date
2026-04-15
On market date
2026-05-12
Original list price
$625,000
Occupant type
Owner
MLS area
32792 - Winter Park/Aloma
Listing AOR
Orlando Regional
Status changed
2026-05-12
Tax legal description
WINTER PARK PINES UNIT FOUR Z/55 LOT 1 BLK C

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 22, 2026 at 9:50 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA