To schedule a showing of 2756 Sheriff Way, Winter Park, Florida, Call David Shippey at 863-521-4517 TODAY!

$595,000 Reduced -$30,000
2756 Sheriff Way
Winter Park, FL 32792
  • 3Beds
  • 2.00Total Baths
  • 2 Full, 0 HalfBaths
  • 1,812SqFt
  • 1965Year Built
  • 0.20Acres
  • MLS# O6402570
  • Residential
  • SingleFamilyResidence
  • Active

  • Approx Time on Market1 month, 9 days
  • Area32792 - Winter Park/aloma
  • CountyOrange
  • Subdivision Winter Park Pines

Overview

**$30,000 Price Improvement!! 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, youll 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 FRIDGEperfect 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 youre 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!



Agriculture / Farm

Association Fees / Info

Community Features:  Pool, Sidewalks

Pets Allowed:  Yes

Association:  Yes

Bathroom Info

Total Baths:  2.00

Fullbaths:  2

Building Info

Roof:  Shingle

Building Area Source:  PublicRecords

Buyer Compensation

Exterior Features

Pool Features:  Community

Fees / Restrictions

Financial

Original Price:  $625,000

Garage / Parking

Attached Garage:  Yes

Garage:  Yes

Green / Env Info

Interior Features

Floors:  Tile

Levels:  One

Laundry Features:  WasherHookup

Interior Features:  CeilingFans

Appliances:  Dryer, Dishwasher, Microwave, Range, Refrigerator, WineRefrigerator, Washer

Lot Info

Direction Remarks:  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.

Lot Size Units:  Acres

Lot Size Acres:  0.2

Lot Sqft:  8,758

Misc

Other

Special Conditions:  None

Other Rooms Info

Property Info

Section:  09

Class Type:  SingleFamilyResidence

Property Sub Type:  SingleFamilyResidence

Construction Materials:  Block

Stories:  1

Foundation:  Slab

Human Modified:  Yes

Room Info

Total Rooms:  6

Sqft Info

Sqft:  1,812

Bulding Area Sqft:  2,388

Living Area Units:  SquareFeet

Living Area Source:  PublicRecords

Tax Info

Tax Year:  2,025

Tax Lot:  1

Tax Legal Description:  WINTER PARK PINES UNIT FOUR Z/55 LOT 1 BLK C

Tax Block:  C

Tax Annual Amount:  5547

Tax Book Number:  Z-55

Unit Info

Utilities / Hvac

Heating:  Central

Water Source:  Public

Sewer:  PublicSewer

Cool System:  CentralAir, CeilingFans

Cooling:  Yes

Heating:  Yes

Utilities:  CableAvailable, ElectricityConnected

Waterfront / Water

Schools

Elem:  Aloma Elem

Middle:  Glenridge Middle

High:  Winter Park High

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.

This listing courtesy of Palm Circle Realty 

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Price & Status History (on davidshippey.com since Tue, Apr 28th 2026)
  • Original Price: $625,000
  • Current Price: $595,000
  • Price Reduced: $30,000
Date ChangedFromTo
06/05/2026$625,000 $595,000 Reduced by $30,000

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If you have any questions on 2756 Sheriff Way, Winter Park, Florida, please call David Shippey at 863-521-4517.


MLS# O6402570 located at 2756 Sheriff Way, Winter Park, Florida is brought to you by David Shippey REALTOR®

2756 Sheriff Way, Winter Park, Florida has 3 Beds, 2 Full Bath, and 0 Half Bath.
The MLS Number for 2756 Sheriff Way, Winter Park, Florida is O6402570.
The price for 2756 Sheriff Way, Winter Park, Florida is $595,000.
The status of 2756 Sheriff Way, Winter Park, Florida is Active.
The subdivision of 2756 Sheriff Way, Winter Park, Florida is Winter Park Pines.
The home located at 2756 Sheriff Way, Winter Park, Florida was built in 2026.