Under contract-accepting backup offers. A rare opportunity to own a beautifully maintained home in the heart of Oakland, offered at an exceptional value under $500,000. Located in the sought-after Longleaf at Oakland community, this 3-bedroom, 2.5-bath home offers a thoughtful layout, beautiful outdoor space, and a prime location—all at a price point that is increasingly hard to find in this desirable area.
Set on a quiet cul-de-sac, the home welcomes you with a modern and functional layout designed for both everyday living and entertaining. Inside, luxury vinyl plank flooring, recessed lighting throughout, and a bright, comfortable feel create a welcoming atmosphere. The kitchen features granite countertops and custom shelving, while additional custom shelving in the laundry room adds both style and practical storage. Spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room provide flexibility for everyday living. A water softener system adds another thoughtful touch to the home.
Step outside to a fully fenced backyard offering privacy and flexibility for pets, play, gardening, or simply enjoying your own outdoor space. The peaceful setting and cul-de-sac location create an inviting sense of privacy while still keeping you close to everything Oakland and Winter Garden have to offer.
The location is hard to beat. Take a quick walk to the West Orange Trail or enjoy easy access to the Oakland Nature Preserve. Downtown Winter Garden’s shops, restaurants, farmers market, and charming atmosphere are just minutes away, while the Florida Turnpike provides convenient access throughout Central Florida. Orlando’s world-class theme parks are approximately 20 minutes away.
Beautifully cared for, ideally located, and thoughtfully priced, 1184 Bobcat Chase Blvd offers an exceptional opportunity to enjoy the best of Oakland living with comfort, convenience, and a price point that makes this home stand out.
Set on a quiet cul-de-sac, the home welcomes you with a modern and functional layout designed for both everyday living and entertaining. Inside, luxury vinyl plank flooring, recessed lighting throughout, and a bright, comfortable feel create a welcoming atmosphere. The kitchen features granite countertops and custom shelving, while additional custom shelving in the laundry room adds both style and practical storage. Spacious bedrooms, a versatile upstairs loft perfect for a home office, media room, or additional living space, and a comfortable family room provide flexibility for everyday living. A water softener system adds another thoughtful touch to the home.
Step outside to a fully fenced backyard offering privacy and flexibility for pets, play, gardening, or simply enjoying your own outdoor space. The peaceful setting and cul-de-sac location create an inviting sense of privacy while still keeping you close to everything Oakland and Winter Garden have to offer.
The location is hard to beat. Take a quick walk to the West Orange Trail or enjoy easy access to the Oakland Nature Preserve. Downtown Winter Garden’s shops, restaurants, farmers market, and charming atmosphere are just minutes away, while the Florida Turnpike provides convenient access throughout Central Florida. Orlando’s world-class theme parks are approximately 20 minutes away.
Beautifully cared for, ideally located, and thoughtfully priced, 1184 Bobcat Chase Blvd offers an exceptional opportunity to enjoy the best of Oakland living with comfort, convenience, and a price point that makes this home stand out.
Property Details
Price:
$499,900
MLS #:
O6442799
Status:
Active Under Contract
Beds:
3
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
LONGLEAF/OAKLAND
Neighborhood:
34787wintergardenoakland
Listed Date:
Sep 23, 2026
Finished Sq Ft:
1,811
Total Sq Ft:
2,547
Lot Size:
4,799 sqft / 0.11 acres (approx)
Year Built:
2019
See this Listing
Schools
Elementary School:
Tildenville Elem
Middle School:
Lakeview Middle
High School:
West Orange High
Interior
Appliances
Cooktop, Refrigerator
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Luxury Vinyl
Heating
Central
Interior Features
Ceiling Fan(s)
Laundry Features
Inside, Laundry Room
Levels
Two
Exterior
Architectural Style
Craftsman
Association Amenities
Playground, Pool
Attached Garage YN
1
Community Features
Community Mailbox, Playground, Pool, Sidewalks
Construction Materials
Block, Concrete, Stucco
Covered Spaces
2
Direction Faces
Northwest
Exterior Features
Irrigation System
Fencing
Vinyl
Garage Spaces
2
Lot Features
Cul-De-Sac
Patio And Porch Features
Covered, Rear Porch
Roof
Shingle
View
Trees/Woods
Financial
HOA Fee
$286
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Maintenance Grounds, Recreational Facilities
HOA Name
Steven Bressler
HOA Name 2
Triad Association Management
HOA Phone
352-602-4803
Tax Year
2025
Taxes
$4,459
Map
Community
- Address1184 BOBCAT CHASE BOULEVARD OAKLAND FL
- SubdivisionLONGLEAF/OAKLAND
- CityOAKLAND
- CountyOrange
- Zip Code34787
Subdivisions in OAKLAND
- BRILEY FARM
- GROVE AT THE HARVEST DISTRICT
- HULL ISLAND ESTATES FIRST ADD
- JOHNS COVE 43/104
- JOHNS LANDING
- JOHNS LANDING PH 01 44/47
- JOHNS LANDING PH 02 48 138
- JOHNS LANDING PHASE 1
- LONGLEAF
- LONGLEAF AT OAKLAND
- LONGLEAF/OAKLAND
- LONGLEAF/OAKLAND REP
- OAKLAND
- OAKLAND PARK
- OAKLAND PK UN 7 NORTH
- OAKLAND TOWN
- OAKLAND TRAILS
- OAKLAND TRAILS PH 1
- OAKLAND TRLS PH 1
- OAKLAND TRLS PH 2
- RYAN COURT
- THE GROVE AT OAKLAND
- WINTERS LNDG PH 01 A D F & G
Market Summary
Current real estate data for Single Family in OAKLAND as of Oct 15, 2026
40
Single Family Listed
104
Avg DOM
349
Avg $ / SqFt
$1,187,685
Avg List Price
Property Summary
- Located in the LONGLEAF/OAKLAND subdivision, 1184 BOBCAT CHASE BOULEVARD OAKLAND FL is a Single Family for sale in OAKLAND, FL, 34787. It is listed for $499,900 and features 3 beds, 3 baths, and has approximately 1,811 square feet of living space, and was originally constructed in 2019. The current price per square foot is $276. The average price per square foot for Single Family listings in OAKLAND is $349. The average listing price for Single Family in OAKLAND is $1,187,685. To schedule a showing of MLS#o6442799 at 1184 BOBCAT CHASE BOULEVARD in OAKLAND, FL, contact your CENTURY 21 Carioti agent at 2392986550.
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Courtesy of THE REAL ESTATE COLLECTION LLC. 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 CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti 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. 1184 BOBCAT CHASE BOULEVARD
OAKLAND, FL
