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$1,500,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 6 Beds
  • 5 Full Baths
  • 3,528 Sq. Ft.
  • Updated 9 days ago
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Under contract-accepting backup offers. Welcome to this exceptional RCB custom home with a pool located in the highly desirable Oakland Park community. Ideally positioned directly across from a green area and surrounded by walking trails on both sides, this home offers park and lake views from the front porch and an upstairs bedroom, creating a peaceful and picturesque setting. The residence features 6 bedrooms and 5 full bathrooms, with two bedrooms located on the first floor. One is a full guest suite with walk-in closet, while the second first-floor bedroom-currently used as a home office with elegant glass French doors excellent flexibility work-from-home needs. Designed for both everyday living and entertaining, the home showcases an outstanding kitchen overlooking the main living area, complemented by a large walk-in pantry, enhanced by a hidden oversized pantry/bar area with microwave and mini beverage refrigerator. Outdoor living is a highlight, featuring a resort-style pool and spa, covered patio, and retractable screen, ideal for year-round enjoyment. The home also offers a rare three-and-a-half car oversized garage, including a dedicated roll-up garage door with direct access to the pool area, plus a large built-out storage attic with staircase access. Additional features and upgrades include LVP flooring, wood beams, electric fireplace, crown molding, metal roof over the front porch, CAT 6 wiring throughout, whole-house water softener, whole-house surge protector, and a home that has been consistently maintained under an air-conditioning service plan. Located just three blocks from the West Orange Trail and within a golf-cart-approved community, the property is within walking distance to Tildenville Elementary School (9/10 rating) with magnet and global language programs, as well as Oakland Charter School and the local middle school. Just minutes from downtown Winter Garden, this home offers exceptional access to dining, shopping, and outdoor recreation. This thoughtfully designed residence combines quality craftsmanship, flexibility, and an outstanding location-offering refined Florida living in one of Oakland's most desirable communities.

Full Property Details for 1008 Tilden Oaks Trl

General

  • Price: $1,500,000
  • HOA FEE: $204/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $12,615 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6371482
  • Updated: 1/9/2026
  • Added to Site: 10 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, PrimaryBedroom Upstairs, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Electric, Living Room
  • Appliances: Dishwasher, Disposal, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 5

Bedrooms

  • Total Bedrooms: 6

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Clubhouse, Playground, Pool, Trail(s)
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Child Safety Fence, Gunite, In Ground, Salt Water
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Irrigation System, Other, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Deck, Front Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Deck, Front Porch, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Alley Access, Garage Door Opener, Garage Faces Rear, On Street, Oversized, Split Garage

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: OAKLAND PARK
  • Driving Directions: From Florida Turnpike, take Exit 272 for SR 50 West (Colonial Dr) toward Winter Garden. Continue west on SR 50. Turn right onto Avalon Rd. Turn left onto Oakland Ave. Proceed to the second entrance of Oakland Park and turn right onto Tilden Oaks Trail. Continue straight, crossing the West Orange Trail drive 1 min, the property will be on the left.
  • Direction Faces: East

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Dock, Clubhouse, Deed Restrictions, Dog Park, Golf Carts OK, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Clubhouse, Playground, Pool, Trail(s)
  • Association: Yes
  • Assoc. Name: Leland Management/Ed Rios
  • Assoc. Fees Include: Community Pool, Manager, Recreational Facilities
  • Pet Restrictions: Contact HOA for pet restrictions.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available

Structural Information

  • Exterior Const.: Block, Cement Siding, Stucco, Wood Siding
  • Roof: Metal, Shingle
  • Windows: Blinds
  • Stories/Levels: Two
  • Square Feet: 3,528
  • Sq. Ft. Source: Public Records
  • Year Built: 2022

Lot Features

  • Property View: Park/Greenbelt, Water
  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,562
  • Lot Size: 7562
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Water Features

  • Water View: Yes

Financial Considerations

  • Association Fee: $611
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $12,615.08
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: OAKLAND PARK UNIT 6B-1 104/67 LOT 78
  • Flood Zone Info: X
  • APN: 212227610200780
  • Property ID: 212227610200780

Listed by Charles Rutenberg Realty Orlando

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Listing agent

— 1008 Tilden Oaks Trl —

  • Charles Rutenberg Realty Orlando

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 1008 Tilden Oaks Trl

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-50.7 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-80.9 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-123.4 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 1008 Tilden Oaks Trl Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/08/2026
Listed
$1,500,000
10.09%
MLS
8/29/2024
Sold
$1,362,500
—
Public Record
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 1008 Tilden Oaks Trl

Year
Property Taxes
Change
Tax Assessment
Change
2024
$15,963
—
$737,089
-23%
2024
$15,963
17%
$961,132
22%
2023
$13,620
641%
$787,842
678%
2021
$1,839
-33%
$101,250
-35%
2022
$2,754
—
$155,000
—
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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Listed by Charles Rutenberg Realty Orlando

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1008 Tilden Oaks Trail, Oakland, FL 34787 (MLS# O6371482) is a Single Family property with 6 bedrooms and 5 full bathrooms. 1008 Tilden Oaks Trail is currently listed for $1,500,000 and was received on January 08, 2026. Want to learn more about 1008 Tilden Oaks Trail? 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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