Welcome home to this beautifully maintained 3-bedroom, 2.5-bath home in the highly sought-after Longleaf at Oakland community! From the moment you arrive, you will appreciate the inviting feel, thoughtful layout, and pride of ownership throughout. Inside, enjoy spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room designed for everyday living and entertaining. Step outside to a wonderful backyard and porch area, with both the family room and porch pre-wired for speakers—perfect for creating an effortless indoor-outdoor entertaining experience. The two-car garage even features an electric vehicle charging outlet. The location is hard to beat— take a quick 5-minute walk to the West Orange Trail, enjoy the shops, dining, and charm of Downtown Winter Garden just 10 minutes away, and reach the Florida Turnpike in minutes. Beautifully cared for, ideally located, and truly move-in ready—this is the Oakland home you’ve been waiting for!
Property Details
Price:
$515,000
MLS #:
S5158021
Status:
Active
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LONGLEAF/OAKLAND REP
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 21, 2026
Finished Sq Ft:
1,811
Total Sq Ft:
2,547
Lot Size:
4,800 sqft / 0.11 acres (approx)
Year Built:
2020
See this Listing
Schools
Interior
Appliances
Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Ice Maker, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Tile, Vinyl
Heating
Central
Interior Features
Ceiling Fan(s), High Ceilings, In Wall Pest System, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s)
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Levels
Two
Exterior
Association Amenities
Park, Pool, Trail(s)
Attached Garage YN
1
Community Features
Community Mailbox, Park, Playground, Pool, Sidewalks
Construction Materials
Block, Concrete, Stucco, Wood Frame
Covered Spaces
2
Direction Faces
North
Exterior Features
Irrigation System, Private Yard, Sidewalk, Sliding Doors
Fencing
Fenced
Garage Spaces
2
Green Energy Efficient
Energy Monitoring System
Lot Features
Sidewalk
Open Parking YN
1
Parking Features
Driveway, Electric Vehicle Charging Station(s), Garage Door Opener
Patio And Porch Features
Covered, Patio
Roof
Shingle
Security Features
Smoke Detector(s)
Window Features
Blinds, Drapes
Financial
HOA Fee
$286
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Maintenance Grounds
HOA Name
Steven Bressler
HOA Phone
352-602-4803
Tax Year
2025
Taxes
$5,045
Map
Community
- Address2696 BOBCAT CHASE BOULEVARD OAKLAND FL
- SubdivisionLONGLEAF/OAKLAND REP
- CityOAKLAND
- CountyOrange
- Zip Code34787
Subdivisions in OAKLAND
- BRILEY FARM
- BRILEY FARM PH 1A
- BRILEY FARM PH 1B
- GROVE AT THE HARVEST DISTRICT
- GROVE/OAKLAND
- HULL ISLAND AT OAKLAND
- HULL ISLAND/OAKLAND PH 2
- JOHNS COVE
- JOHNS COVE 43/104
- JOHNS LANDING
- JOHNS LANDING PH 2
- LAKE JOHNS MOTEL APTS. & TR. PK
- LONGLEAF/OAKLAND REP
- OAKLAND
- OAKLAND PARK
- OAKLAND PARKB-3
- OAKLAND POINTE
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- TOWN/OAKLAND
- VERDE PARK PH 1
Market Summary
Current real estate data for Single Family in OAKLAND as of Sep 22, 2026
39
Single Family Listed
106
Avg DOM
369
Avg $ / SqFt
$1,350,038
Avg List Price
Property Summary
- Located in the LONGLEAF/OAKLAND REP subdivision, 2696 BOBCAT CHASE BOULEVARD OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34787. It is listed for $515,000 and features 3 beds, 3 baths, and has approximately 1,811 square feet of living space, and was originally constructed in 2020. The current price per square foot is $284. The average price per square foot for Single Family listings in OAKLAND is $369. The average listing price for Single Family in OAKLAND is $1,350,038. To schedule a showing of MLS#s5158021 at 2696 BOBCAT CHASE BOULEVARD in OAKLAND, FL, contact your WINDERMERE INTERNATIONAL REALTY agent at 4079901329.
Similar Listings Nearby
Courtesy of THE PROPERTY FIRM. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than WINDERMERE INTERNATIONAL REALTY include the name of the listing broker. Neither the listing company nor WINDERMERE INTERNATIONAL REALTY shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 2696 BOBCAT CHASE BOULEVARD
OAKLAND, FL