$625,000
2756 Sheriff Way
Winter Park, FL 32792
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
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
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
- Status: ActiveMay 12, 2026
- Listed$625,000May 12, 2026
- 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
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
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | 13x12 |
| Dining Room | First | 10x13 |
| Living Room | First | 18x15 |
| Primary Bedroom | First | 16.5x10.5 |
| Bedroom 2 | First | 12x20.5 |
| Bedroom 3 | First | 11.5x10.5 |
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-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.
More homes like this
$475,000
346 S Ranger Blvd
Winter Park, FL 32792
3 bd · 2 ba · 1,592 sqft
Winter Park Pines
MLS# S5134662
$495,000
2803 Banchory Rd
Winter Park, FL 32792
4 bd · 2 ba · 1,596 sqft
Winter Park Pines
MLS# O6404011
$579,000
333 Cornwall Rd
Winter Park, FL 32792
4 bd · 2 ba · 1,660 sqft
Winter Park Pines
MLS# O6409379
$598,000
2758 Banchory Rd
Winter Park, FL 32792
3 bd · 3 ba · 1,539 sqft
Winter Park Pines
MLS# O6329628
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