
2755 Bobcat Chase Blvd Oakland, FL 34787
Estimated payment $3,489/month
Highlights
- Loft
- Great Room
- Community Pool
- West Orange High School Rated A
- Granite Countertops
- 2 Car Attached Garage
About This Home
Live just minutes from the charm of Downtown Winter Garden in the desirable Oakland community, where you'll find a modern 3-bedroom home with a bonus room—built in 2020, filled with upgrades and situated on a quiet cul-du-sac street. Located in Oakland, one of Central Florida’s most quaint and desirable small towns, 2755 Bobcat Chase offers a rare blend of peaceful living with unbeatable convenience. Oakland is known for its tree-lined streets, welcoming community feel and commitment to preserving nature—while still being just minutes from the shops, restaurants and year-round events of historic Downtown Winter Garden. Step inside this well-designed home to find an open-concept main level that connects your living, dining and kitchen areas seamlessly. The kitchen is a standout with quartz countertops, stainless steel appliances and a large pantry—perfect for entertaining or everyday use. Upstairs, enjoy a flexible bonus room that can serve as a home office, playroom or media space. The spacious primary suite offers a walk-in closet and private bath with dual vanities, while two additional bedrooms share a full bath. A convenient half-bath is located downstairs for guests. Built in 2020, this home features energy-efficient construction, an inside laundry room, a two-car garage, screened in lanai and a fully fenced backyard ready for pets or outdoor enjoyment. Outdoor enthusiasts will love the neighborhood’s prime location—situated just across the street from both the Oakland Nature Preserve and easy access to the West Orange Trail. The Oakland Nature Preserve offers over 100 acres of preserved land with scenic boardwalks, hiking trails and educational programs that immerse you in Florida’s native wildlife and habitats. Meanwhile, the West Orange Trail—a 22-mile paved pathway—provides a scenic route for walking, running, biking and skating, connecting you to downtown Winter Garden, local parks and other trail systems throughout Orange County.This rare combination of natural beauty and connectivity makes it easy to enjoy the outdoors just steps from your front door. With quick access to the Florida Turnpike, commuting to downtown Orlando, the airport or Disney is simple—making this location both practical and peaceful.Don’t miss your opportunity to own a modern, move-in-ready home in Oakland—where charm, community and convenience come together. Schedule your private tour today.
Listing Agent
KELLER WILLIAMS ELITE PARTNERS III REALTY Brokerage Phone: 321-527-5111 License #3232332 Listed on: 07/01/2025

Home Details
Home Type
- Single Family
Est. Annual Taxes
- $4,899
Year Built
- Built in 2020
Lot Details
- 4,800 Sq Ft Lot
- Southeast Facing Home
- Fenced
- Property is zoned PUD
HOA Fees
- $276 Monthly HOA Fees
Parking
- 2 Car Attached Garage
Home Design
- Slab Foundation
- Metal Roof
- Stucco
Interior Spaces
- 1,822 Sq Ft Home
- 2-Story Property
- Ceiling Fan
- Sliding Doors
- Great Room
- Family Room Off Kitchen
- Dining Room
- Loft
Kitchen
- Breakfast Bar
- Range
- Microwave
- Dishwasher
- Granite Countertops
- Disposal
Flooring
- Carpet
- Laminate
- Tile
Bedrooms and Bathrooms
- 3 Bedrooms
- Bathtub With Separate Shower Stall
- Shower Only
Laundry
- Laundry Room
- Laundry in Kitchen
- Washer and Electric Dryer Hookup
Outdoor Features
- Private Mailbox
Utilities
- Central Heating and Cooling System
- Electric Water Heater
- Cable TV Available
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 60 / 5101 00
- Assessor Parcel Number 20-22-27-5101-00-600
Community Details
Overview
- Association fees include pool
- Triad Assoc. Mgt / Martha Ledford Association, Phone Number (352) 602-4803
- Longleaf/Oakland Rep Subdivision
- Association Owns Recreation Facilities
- The community has rules related to deed restrictions
Amenities
- Community Mailbox
Recreation
- Community Playground
- Community Pool
- Park
Map
Home Values in the Area
Average Home Value in this Area
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $4,899 | $320,011 | -- | -- |
2024 | $4,622 | $320,011 | -- | -- |
2023 | $4,622 | $301,934 | $0 | $0 |
2022 | $4,482 | $293,140 | $0 | $0 |
2021 | $4,430 | $284,602 | $95,000 | $189,602 |
2020 | $1,324 | $75,000 | $75,000 | $0 |
2019 | $840 | $45,000 | $45,000 | $0 |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
07/29/2025 07/29/25 | Price Changed | $514,913 | -2.8% | $283 / Sq Ft |
07/01/2025 07/01/25 | For Sale | $529,500 | -- | $291 / Sq Ft |
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Quit Claim Deed | $100 | None Listed On Document | |
Special Warranty Deed | $347,700 | Pgp Title |
About the Listing Agent

At the Tania Matthews Team, they provide personal attention to each client's needs and build trust through transparency. They aim to make your real estate purchase or sale experience effortless. Their mission is to serve first and provide first-class services and expertise to discerning buyers locally and around the world. Tania's strong work ethic, negotiating skills, integrity, and commitment to protecting her client's best interest is what has made her one of the top agents in the Orlando
Tania's Other Listings
Source: Stellar MLS
MLS Number: G5098929

APN: 20-2227-5101-00-600
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