855 OAKLAND PARK BOULEVARD Winter Garden, FL $ 875,000
855 OAKLAND PARK BOULEVARD
$ 875,000
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855 OAKLAND PARK BOULEVARD

Winter Garden, FL, 34787
$ 875,000
Bedrooms4 Baths2.1 Sq 2,553

Monthly Estimate*

$ 5,388

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Single Family Home for sale in Winter Garden, FL

for $875,000 with 4 bedrooms and 2 full baths, 1 half bath. This 2,553 square foot home was built in 2014 on a lot size of 0.16.

Welcome to Oakland Park, one of Winter Garden’s most desirable communities. Thoughtfully built by David Weekley Homes, this beautifully maintained 4-bedroom, 2.5-bath Oakland Park Boulevard home features a First-Floor primary suite, First-Floor home office, and a peaceful water view with no rear neighbors. Stylish updates include Luxury Vinyl Plank flooring, modernized kitchen cabinetry with new backsplash, and a freshly painted exterior (December 2024). Additional highlights include a whole-house 22kW generator, NEW A/C (October 2025), and an EV charging station. Ideally situated within the golf cart district, enjoy direct access to the West Orange Trail and an easy ride to Downtown Winter Garden. Oakland Park residents love the resort-style amenities—two community pools, scenic walking and biking trails, multiple parks, playgrounds, and a clubhouse—offering the perfect blend of luxury, comfort, and community living.

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Single Family Active

Price

$ 875,000

Bedrooms

4

Full Bath

2

Half Bath

1

Property Type

Single Family

Taxes

$ 6,405

Style

Elevated

Lot Size

0.16

Year Built

2014

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6383325

Features
General
Sewer Public Sewer
Heating Central Natural Gas
Cooling Central Air
Utilities Cable Available Electricity Connected Natural Gas Connected Public Street Lights Underground Utilities Water Connected
Roof Shingle
Appliances Dishwasher Disposal Dryer Gas Water Heater Microwave Other Range Refrigerator Trash Compactor Washer
Zoning PUD
HOA Fee 625
Garage Spaces 2
Association Fee Includes Community Pool Manager Pool Maintenance Recreational Facilities
Patio/Porch Features Covered Enclosed Front Porch Patio Porch
Architectural Style Elevated
Security Features Security System
Construction Materials Stucco
Pets Allowed Yes
Year Built 2014
View Water
Levels Two
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Community Features Clubhouse Deed Restrictions Dog Park Golf Carts OK Park Playground Pool Sidewalks
Assoc Fee Paid Per Quarterly
County Orange
New Construction false
Property Type Residential
Association Amenities Clubhouse Park Playground Pool Spa/Hot Tub Trail(s)
Attached Garage false
Energy Efficient Insulation
Subdivision Name OAKLAND PARK UT 1B - 1A
Facing Direction West
Garage Y/N true
Total Rooms 4
Full Baths 2
Status Active
Directions From the turnpike take exit 267B and stay left on ramp heading towards Clermont and travel 3 miles on SR 50 to tildenville school road then turn right. Go to the first light. Oakland Ave/Plant street and turn left onto Oakland Ave. Community is on the R.
High School West Orange High
City WINTER GARDEN
Association Name Oakland Park Association INC.
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 7002
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Tildenville Elem
Land Lease Y/N false
Tax Annual Amount 6405
Home Warranty Y/N true
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N false
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 73
Legal Description OAKLAND PARK UNIT 1B - 1A 76/8 LOT 73
Water View Pond
Minimum Lease 8-12 Months
Water Access Y/N false
Monthly HOA Amount 208.33
Additional Rooms Bonus Room Den/Library/Office Family Room Loft Media Room Storage Rooms
Water View Y/N true
Flood Zone Code X
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Interior
Interior Amenities Built-in Features Ceiling Fan(s) Eating Space In Kitchen High Ceilings Kitchen/Family Room Combo Living Room/Dining Room Combo Open Floorplan Other Primary Bedroom Main Floor Smart Home Solid Surface Counters Solid Wood Cabinets Split Bedroom Stone Counters Walk-In Closet(s) Window Treatments
Flooring Luxury Vinyl Tile
Furnished Y/N Unfurnished
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Double Pane Windows ENERGY STAR Qualified Windows Window Treatments
Fireplace Y/N false
Half Baths 1
Laundry Features Gas Dryer Hookup Inside
Total Bedrooms 4
Total Baths 3
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Exterior
Exterior Amenities Garden Irrigation System Lighting Other Rain Gutters Sidewalk
Vegetation Oak Trees Trees/Landscaped
Fencing Fenced
Parking Features Garage Door Opener Golf Cart Parking Guest Off Street Oversized
Lot Features Cleared City Lot Irregular Lot Landscaped
Water Source Public
Lot Size Area 7002
Foundation Details Slab
Spa false
Building Area Total 3566
Lot Size Acres 0.16
Road Surface Type Asphalt Paved
Private Pool false
Waterfront Y/N false
Covered Spaces 2
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* Excluded Features
List By
Homevest Realty

Broker

erica@ericadiazteam.com

Email

Affordability Calculator

$5,921
Per Month
91%
9%
0%
Monthly Principal & Interest
$5,388
Monthly Property Taxes
$534
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
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
2/18/2026$875,000 Listed Price

Map


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855 OAKLAND PARK BOULEVARD, Winter Garden, FL, 34787 is a Single Family Home for sale at $875,000 with 2,553 sqft and a lot size of 0.16. 855 OAKLAND PARK BOULEVARD has 4 bedrooms, 2.1 baths, and was built in 2014. The property's zip code is 34787 which is in Winter Garden, FL