311 E 8TH AVENUE Windermere, FL $ 1,660,000
311 E 8TH AVENUE
$ 1,660,000
Share Save

311 E 8TH AVENUE

Windermere, FL, 34786
$ 1,660,000
Bedrooms5 Baths4.0 Sq 3,805

Monthly Estimate*

$ 10,356

311 E 8TH AVENUE, Windermere, FL 34786 - Image 1
311 E 8TH AVENUE, Windermere, FL 34786 - Image 2
311 E 8TH AVENUE, Windermere, FL 34786 - Image 3
311 E 8TH AVENUE, Windermere, FL 34786 - Image 4
311 E 8TH AVENUE, Windermere, FL 34786 - Image 5
311 E 8TH AVENUE, Windermere, FL 34786 - Image 6
311 E 8TH AVENUE, Windermere, FL 34786 - Image 7
311 E 8TH AVENUE, Windermere, FL 34786 - Image 8
311 E 8TH AVENUE, Windermere, FL 34786 - Image 9
311 E 8TH AVENUE, Windermere, FL 34786 - Image 10
311 E 8TH AVENUE, Windermere, FL 34786 - Image 11
311 E 8TH AVENUE, Windermere, FL 34786 - Image 12
311 E 8TH AVENUE, Windermere, FL 34786 - Image 13
311 E 8TH AVENUE, Windermere, FL 34786 - Image 14
311 E 8TH AVENUE, Windermere, FL 34786 - Image 15
311 E 8TH AVENUE, Windermere, FL 34786 - Image 16
311 E 8TH AVENUE, Windermere, FL 34786 - Image 17
311 E 8TH AVENUE, Windermere, FL 34786 - Image 18
311 E 8TH AVENUE, Windermere, FL 34786 - Image 19
311 E 8TH AVENUE, Windermere, FL 34786 - Image 20
311 E 8TH AVENUE, Windermere, FL 34786 - Image 21
311 E 8TH AVENUE, Windermere, FL 34786 - Image 22
311 E 8TH AVENUE, Windermere, FL 34786 - Image 23
311 E 8TH AVENUE, Windermere, FL 34786 - Image 24
311 E 8TH AVENUE, Windermere, FL 34786 - Image 25
311 E 8TH AVENUE, Windermere, FL 34786 - Image 26
311 E 8TH AVENUE, Windermere, FL 34786 - Image 27
311 E 8TH AVENUE, Windermere, FL 34786 - Image 28
311 E 8TH AVENUE, Windermere, FL 34786 - Image 29
311 E 8TH AVENUE, Windermere, FL 34786 - Image 30
311 E 8TH AVENUE, Windermere, FL 34786 - Image 31
311 E 8TH AVENUE, Windermere, FL 34786 - Image 32
311 E 8TH AVENUE, Windermere, FL 34786 - Image 33
311 E 8TH AVENUE, Windermere, FL 34786 - Image 34
311 E 8TH AVENUE, Windermere, FL 34786 - Image 35
311 E 8TH AVENUE, Windermere, FL 34786 - Image 36
311 E 8TH AVENUE, Windermere, FL 34786 - Image 37
311 E 8TH AVENUE, Windermere, FL 34786 - Image 38
311 E 8TH AVENUE, Windermere, FL 34786 - Image 39
311 E 8TH AVENUE, Windermere, FL 34786 - Image 40
311 E 8TH AVENUE, Windermere, FL 34786 - Image 41
311 E 8TH AVENUE, Windermere, FL 34786 - Image 42
311 E 8TH AVENUE, Windermere, FL 34786 - Image 43
311 E 8TH AVENUE, Windermere, FL 34786 - Image 44
311 E 8TH AVENUE, Windermere, FL 34786 - Image 45
311 E 8TH AVENUE, Windermere, FL 34786 - Image 46
311 E 8TH AVENUE, Windermere, FL 34786 - Image 47
311 E 8TH AVENUE, Windermere, FL 34786 - Image 48
311 E 8TH AVENUE, Windermere, FL 34786 - Image 49
311 E 8TH AVENUE, Windermere, FL 34786 - Image 50
311 E 8TH AVENUE, Windermere, FL 34786 - Image 51
311 E 8TH AVENUE, Windermere, FL 34786 - Image 52
311 E 8TH AVENUE, Windermere, FL 34786 - Image 53
311 E 8TH AVENUE, Windermere, FL 34786 - Image 54
311 E 8TH AVENUE, Windermere, FL 34786 - Image 55
311 E 8TH AVENUE, Windermere, FL 34786 - Image 56
311 E 8TH AVENUE, Windermere, FL 34786 - Image 57
311 E 8TH AVENUE, Windermere, FL 34786 - Image 58
311 E 8TH AVENUE, Windermere, FL 34786 - Image 59
View a Virtual Tour

Single Family Home for sale in Windermere, FL

for $1,660,000 with 5 bedrooms and 4 full baths. This 3,805 square foot home was built in 1913 on a lot size of 0.23.

Luxury Lakefront Living in Downtown Windermere | Fresh Opportunity on Lake Bessie. Welcome to your private slice of lakefront paradise on Lake Bessie, where luxury living meets laid-back charm in the heart of Downtown Windermere. Imagine waking up to shimmering water views, paddle-boarding before breakfast, and ending each day with sunsets that paint the sky—this is everyday life at 311 E 8th Avenue. Tucked within one of Central Florida’s most desirable communities, this home offers unmatched privacy, no HOA, and timeless design with modern updates. A screened front porch sets a relaxed tone, leading into an open floor plan that blends comfort and sophistication. The chef’s kitchen with stainless steel appliances, natural gas range, and custom cabinetry opens to sunlit gathering spaces that overlook the lake, creating an effortless flow for entertaining. A cozy fireplace anchors the dining area, framed by windows with views of the koi pond and rock waterfall. Two main-floor ensuite bedrooms provide convenience for family or guests, while the upstairs primary suite feels like a private sanctuary with panoramic views of Lake Bessie and Isleworth Golf Course, a spa-inspired bath, and a spacious walk-in closet. Outside, life slows down. Start your mornings lakeside with coffee and birdsong, spend afternoons fishing or paddle-boarding from your own shoreline, and wind down by the firepit under the stars. Recent updates—50-year architectural roof, Carrier AC units, new flooring, water softener, updated drain field, and fresh paint inside and out—offer peace of mind for years to come. Here, every day feels like a getaway. Windermere’s golf cart-friendly lifestyle puts you steps from weekly farmers markets, local cafés, food truck Fridays, and the Butler Chain of Lakes. Zoned for top-rated schools and only minutes from Winter Garden, Dr. Phillips, and Disney, this rare property blends luxury, lifestyle, and lakefront living in one unforgettable home. Your lakefront story begins here. Schedule your private tour today. One or more pictures are virtually staged.

See more

Single Family Active

Price

$ 1,660,000

Bedrooms

5

Full Bath

4

Property Type

Single Family

Taxes

$ 15,684

Style

Single Family Residence

Lot Size

0.23

Year Built

1913

Town/City

Windermere

County/Region

Orange

MLS | Web ID

O6333319

Features
Interior
Interior Amenities built-in features ceiling fan(s) crown molding eating space in kitchen open floorplan primarybedroom upstairs solid surface counters solid wood cabinets split bedroom walk-in closet(s)
Flooring carpet ceramic tile vinyl
Fireplace Features family room gas
Air Conditioning Y/N yes
Heating Y/N yes
Fireplace Y/N yes
Half Baths 0
Laundry Features inside
Total Bedrooms 5
Total Baths 4
See more
General
Sewer septic tank
Heating central
Cooling central air
Utilities bb/hs internet available electricity connected natural gas available natural gas connected
Roof shingle
Appliances dishwasher disposal dryer gas water heater microwave range refrigerator washer water softener wine refrigerator
Zoning sfr
Construction Materials wood frame wood siding
Year Built 1913
Levels two
Property Subtype single family residence
Tax Year 2024
Ownership fee simple
Waterfront Features lake waterfront lake front
Community Features community boat ramp fishing lake water access waterfront golf carts ok
County orange
New Construction no
Property Type residential
HOA N
Subdivision Name windermere town
Facing Direction southeast
Garage Y/N no
Total Rooms 8
Full Baths 4
Status active
Directions head west on 6th avenue from conroy windermere road left on bessie street home is on the right.
High School olympia high
City windermere
Body of Water lake bessie
Senior Community Y/N no
MLS Area 34786 - windermere
Lot Size Units square feet
Lot Size Square Feet 10000
Carport Spaces 2
Carport Y/N yes
Listing Terms cash conventional va loan
Elementary School windermere elem
Land Lease Y/N no
Tax Annual Amount 15684
Middle/Junior High School gotha middle
Additional Parcels Y/N no
Lease Considered Y/N yes
Virtual Tour https://www.propertypanorama.com/instaview/stellar/o6333319
Building Area Units square feet
Living Area Units square feet
Standard Status active
Occupancy Type vacant
Tax Lot 164
Legal Description plat of windermere g/36 the e 100 ft oflot 164
Water View lake
Water Access Type lake
Minimum Lease 8-12 months
Water Access Y/N yes
Water View Y/N yes
Flood Zone Code x
DockY/N no
See more
Exterior
Exterior Amenities french doors garden irrigation system lighting rain gutters
Fencing wood
Parking Features assigned covered driveway off street
Water Source well
Lot Size Area 10000
Foundation Details crawlspace slab
Building Area Total 3805
Lot Size Acres 0.23
Road Surface Type dirt gravel
Private Pool no
Waterfront Y/N yes
Covered Spaces 2
See more
Internal Only
Street Number 1 311
See more
* Excluded Features
List By
Coldwell Banker Residential Re

Broker

karen72.oneil@gmail.com

Email

Affordability Calculator

$11,663
Per Month
89%
11%
0%
Monthly Principal & Interest
$10,356
Monthly Property Taxes
$1,307
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
3324044 Elementary School
3219949 Middle School
Olympia High High School
Pricing History
DatePricePrice ChangeDescription
10/21/2025$1,660,000 -5.14% Price Down
8/8/2025$1,750,000 Listed Price

Map


See all

311 E 8TH AVENUE, Windermere, FL, 34786 is a Single Family Home for sale at $1,660,000 with 3,805 sqft and a lot size of 0.23. 311 E 8TH AVENUE has 5 bedrooms, 4.0 baths, and was built in 1913. The property's zip code is 34786 which is in Windermere, FL