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$880,000

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 6 Full Baths
  • 1 Partial Bath
  • 5,700 Sq. Ft.
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Discover unparalleled versatility and breathtaking lakefront living with this beautifully remodeled/converted dual-unit home on the shores of Lake Jessie in Winter Haven, Florida. Although zoned single-family residential, this property has been thoughtfully converted into two stunning living spaces-ideal for multigenerational families, in-law accommodations, or dual-family living side-by-side. Unit 1- 2,900 SF welcomes you with a fully renovated two-story layout featuring 4 bedrooms and 3 full bathrooms and 1 half bath. Enjoy gorgeous lakefront views from multiple vantage points and modern finishes throughout, creating the perfect blend of comfort and style. Unit 2- 2,800 SF, mirrors the same level of craftsmanship, two story offering 5 bedrooms and 3 full bathrooms. This spacious unit is also fully remodeled and showcases sweeping views of Lake Jessie, making every day feel like a retreat. Two car garage with additional storage room off the front of the garage. Your backyard becomes a true private oasis-complete with a fire pit, outdoor grill area with a pergola, and a covered boat dock equipped with a boat lift, water, and electric. Watch sea planes take off and land daily from Brown's Sea Plane Base right from your own waterfront sanctuary. Whether you're seeking a unique multigenerational setup, an expansive home for a large family, or the ultimate lakeside lifestyle, this exceptional property delivers it all. Don't miss the opportunity to own this one-of-a-kind lakefront retreat in beautiful Winter Haven, Florida.

Full Property Details for 906 Lake Jessie Dr

General

  • Price: $880,000
  • Taxes: $5,236 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: L4957757
  • Updated: 12/7/2025
  • Added to Site: 42 day(s) ago

Rental Information

  • Min. Lease: 1-7 Days

Interior

  • Number of Rooms: 6
  • Interior Features: Ceiling Fan(s), Stone Counters, Thermostat
  • Appliances: Dishwasher, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 7
  • Full Bathrooms: 6
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 9

Other Rooms

  • Laundry: Inside

Exterior

  • Exterior Features: Fire Pit, Outdoor Grill, Private Mailbox, Private Yard

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway, Garage Door Opener

Location

  • Area: 33881 - Winter Haven / Florence Villa
  • County: Polk
  • Development Name: 33881 - Winter Haven / Florence Villa
  • Subdivision: EAST VIEW PKWY
  • Driving Directions: Take Havendale Blvd. west from Winter Haven to Jersey Rd. Take a right on Jersey and take Jersey to Sherry Avenue NW and take a right. Take Sherry to Lake Jessie Dr. At Lake Jessie Drive take a right and the property will be down on your left.
  • Direction Faces: West

School Information

  • Elementary School: Auburndale Central Elem
  • Middle School: Westwood Middle
  • High School: Auburndale High School

Community

  • Community Name: 33881 - Winter Haven / Florence Villa

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water District: LAKE JESSIE
  • Water: Public
  • Utility Description: Electricity Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 5,700
  • Sq. Ft. Source: Owner
  • Year Built: 1954

Additional Structures

  • Other Structures: Guest House, Other, Outdoor Kitchen

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.47
  • Lot Size (Sq. Ft.): 20,604
  • Lot Size: 20604
  • Lot Dimensions: 93 x 204
  • Street/Road Desc.: Paved

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Lake - Chain of Lakes
  • Water Extras: Yes
  • Water Front Name: LAKE JESSIE
  • Water Front Desc.: Lake - Chain of Lakes

Financial Considerations

  • Tax Amount: $5,236.7
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: EAST VIEW PARKWAY PB 13 PG 4 LOT 15 LESS N 15 FT & N 45 FT OF 16
  • Flood Zone Info: AE*
  • APN: 252812338500000152
  • Property ID: 252812338500000152
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 906 Lake Jessie Dr —

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NMLS#: 1598647

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Be ready to buy your new home!

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NMLS#: 1598647

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Schools serving 906 Lake Jessie Dr

School District:Polk County School District
NameGradesDistance
Auburndale Central Elementary School
320 Lemon Street, Auburndale, FL 33823
PK-51.3 mi
Auburndale Senior High School
1 Bloodhound Trail, Auburndale, FL 33823
9-121.6 mi
Westwood Middle School, Winter Haven, FL
3520 Avenue J Northwest, Winter Haven, FL 33881
6-81.7 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 906 Lake Jessie Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/06/2025
Listed
$880,000
158.82%
MLS
11/21/2022
Sold
$340,000
—
Public Record
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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 906 Lake Jessie Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,237
13%
$344,467
—
2023
$4,624
221%
$342,858
93%
2022
$1,442
-24%
$177,770
3%
2021
$1,909
—
$172,592
1%
2021
$1,909
11%
$170,209
5%
2017
$1,725
—
$162,298
2%
2017
$1,725
-6%
$158,960
-4%
2019
$1,828
12%
$166,382
9%
2016
$1,631
-47%
$152,262
-13%
2015
$3,096
9%
$174,934
9%
2014
$2,844
-9%
$160,085
-8%
2013
$3,116
—
$173,509
—
View All
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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906 Lake Jessie Drive, Winter Haven, FL 33881 (MLS# L4957757) is a Single Family property with 9 bedrooms, 6 full bathrooms and 1 partial bathroom. 906 Lake Jessie Drive is currently listed for $880,000 and was received on December 06, 2025. This property is listed by Brandy Duncan Group from our Winter Haven / Lake Wales Office.Want to learn more about 906 Lake Jessie Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.

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