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$495,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,822 Sq. Ft.
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Welcome to 2755 Bobcat Chase Blvd, a modern 3-bedroom, 2.5-bath home with a bonus room, built in 2020 and tucked away on a quiet cul-de-sac in the highly desirable town of Oakland. This home offers a beautifully designed open-concept main level with a spacious living area that flows seamlessly into the dining space and upgraded kitchen featuring quartz countertops, stainless steel appliances, a large pantry, and a functional layout ideal for everyday living or entertaining. Upstairs, the bonus room provides flexible space for an office, media room, or play area. The primary suite includes a walk-in closet and private bath with dual sinks, while two additional bedrooms and a full bath complete the second level. Additional highlights include energy-efficient construction, a two-car garage, an inside laundry room, a screened lanai, and a fully fenced backyard. Located minutes from Downtown Winter Garden and directly across from the Oakland Nature Preserve and the West Orange Trail, this home offers the rare blend of peaceful living and exceptional convenience. Enjoy access to miles of walking and biking trails, scenic boardwalks, parks, and year-round community activities. With nearby access to the Florida Turnpike, commuting to Orlando, the airport, or the theme parks is quick and easy. This move-in-ready Oakland home is the perfect combination of comfort, style, and location.

Full Property Details for 2755 Bobcat Chase Blvd

General

  • Price: $495,000
  • HOA FEE: $276/month
  • Taxes: $4,899 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: G5098929
  • Updated: 1/1/2026
  • Added to Site: 201 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 10
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination
  • Appliances: Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
  • Flooring: Carpet, Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Electric Dryer Hookup, In Kitchen, Laundry Room, Washer Hookup

Exterior

  • Exterior Features: Private Mailbox, Sliding Doors

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: LONGLEAF/OAKLAND REP
  • Driving Directions: State Rte 50 E/E Hwy 50, Turn left onto W Oakland Ave, At the traffic circle, take the 1st exit and stay on W Oakland Ave, Turn right onto Sansparilla Rd, Turn right onto Bobcat Chase Blvd, Destination will be on the right
  • Direction Faces: Southeast

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Association Recreation - Owned, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Sidewalks
  • Association: Yes
  • Assoc. Name: Triad Assoc. Mgt / Martha Ledford
  • Assoc. Fees Include: Community Pool
  • Pet Restrictions: Buyer to verify HOA GUIDELINES FOR ANY PET RESTRICTIONS as well as any City/County GUIDELINES FOR ANY PET RESTRICTIONS

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Public, Sewer Connected

Structural Information

  • Exterior Const.: Stucco
  • Roof: Metal
  • Stories/Levels: Two
  • Square Feet: 1,822
  • Sq. Ft. Source: Public Records
  • Year Built: 2020

Lot Features

  • Lot Size (Acres): 0.11
  • Lot Size (Sq. Ft.): 4,800
  • Lot Size: 4800
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Fenced, Other

Financial Considerations

  • Association Fee: $276
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,899.34
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LONGLEAF AT OAKLAND, A REPLAT 99/17 LOT60
  • Flood Zone Info: X
  • APN: 202227510100600
  • Property ID: 202227510100600
  • Block/Lot/Section: 5101 00

Listed by Keller Williams Elite Partners Iii Realty

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Listing agent

— 2755 Bobcat Chase Blvd —

  • Keller Williams Elite Partners Iii Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2755 Bobcat Chase Blvd

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-52 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-82.4 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-124.5 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2755 Bobcat Chase Blvd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/01/2026
Price Reduced
$495,000
-1%
MLS
11/28/2025
Price Reduced
$500,000
-0.99%
MLS
10/22/2025
Price Reduced
$504,995
-1.93%
MLS
7/29/2025
Price Reduced
$514,913
-2.75%
MLS
7/01/2025
Listed
$529,500
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2755 Bobcat Chase Blvd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$4,899
—
$320,011
3%
2024
$4,899
6%
$310,992
3%
2023
$4,622
3%
$301,934
3%
2022
$4,482
1%
$293,140
3%
2021
$4,430
—
$284,602
279%
2021
$4,430
—
$75,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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NMLS#: 1598647

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Listed by Keller Williams Elite Partners Iii Realty

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2755 Bobcat Chase Boulevard, Oakland, FL 34787 (MLS# G5098929) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 2755 Bobcat Chase Boulevard is currently listed for $495,000 and was received on July 01, 2025. Want to learn more about 2755 Bobcat Chase Boulevard? Do you have questions about finding other Single Family real estate for sale in Oakland? You can browse all Oakland real estate or contact a Coldwell Banker agent to request more information.

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