2756 SHERIFF WAY Winter Park, FL $ 595,000
2756 SHERIFF WAY
$ 595,000
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2756 SHERIFF WAY

Winter Park, FL, 32792
$ 595,000
Bedrooms3 Baths2.0 Sq 1,812

Monthly Estimate*

$ 3,664

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Single Family Home for sale in Winter Park, FL

for $595,000 with 3 bedrooms and 2 full baths. This 1,812 square foot home was built in 1965 on a lot size of 0.2.

Under contract-accepting backup offers. **$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, 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!

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Single Family Pending

Price

$ 595,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 5,547

Style

Single Family Residence

Lot Size

0.2

Year Built

1965

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

O6402570

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Cable Available Electricity Connected
Possession Close Of Escrow
Roof Shingle
Appliances Dishwasher Dryer Microwave Range Refrigerator Washer Wine Refrigerator
Zoning R-1A
Garage Spaces 2
Construction Materials Block
Pets Allowed Yes
Year Built 1965
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Pool
County Orange
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name WINTER PARK PINES
Facing Direction North
Garage Y/N true
Total Rooms 6
Full Baths 2
Status Pending
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.
High School Winter Park High
City WINTER PARK
Association Name Peter Mason
Senior Community Y/N false
MLS Area 32792 - Winter Park/Aloma
Lot Size Units Square Feet
Lot Size Square Feet 8758
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Aloma Elem
Land Lease Y/N false
Tax Annual Amount 5547
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.zillow.com/view-imx/f25c3dcc-b2f0-441d-9c62-adc13b338b6e?setAttribution=mls&wl=true&initialViewType=pano&utm_source=dashboard
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Owner
Tax Lot 1
Legal Description WINTER PARK PINES UNIT FOUR Z/55 LOT 1 BLK C
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Ceiling Fan(s)
Flooring Tile
Furnished Y/N Unfurnished
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Washer Hookup
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Sidewalk
Water Source Public
Lot Size Area 8758
Foundation Details Slab
Building Area Total 2388
Lot Size Acres 0.2
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Palm Circle Realty

Broker

kasey@sellingthefldream.com

Email

Affordability Calculator

$4,126
Per Month
89%
11%
0%
Monthly Principal & Interest
$3,664
Monthly Property Taxes
$462
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
6/5/2026$595,000 -4.80% Price Down
5/12/2026$625,000 Listed Price

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2756 SHERIFF WAY, Winter Park, FL, 32792 is a Single Family Home for sale at $595,000 with 1,812 sqft and a lot size of 0.2. 2756 SHERIFF WAY has 3 bedrooms, 2.0 baths, and was built in 1965. The property's zip code is 32792 which is in Winter Park, FL