311 E 8th Ave, Windermere, FL 34786
Property image
Property image
OFF MARKET

$1,438,800

Trulia Estimate
as of Sep 29, 2026
  • 5 Beds
  • 4 Baths
  • 3,805 sqft

311 E 8th Ave, Windermere, FL 34786

Home Highlights

Single-Family Home
3,805 sqft
$378/sqft

Local Information

  • Map ViewExplore the area around 311 E 8th Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:Two main-floor ensuite bedroomsNatural gas rangeCustom cabinetryPeaceful water frontageScreened front porchSpa-inspired bath
Luxury Lakefront Executive Rental in Downtown Windermere on Lake Bessie. Now offered at a newly adjusted price, this rare 5-bedroom lakefront home presents one of the most compelling rental opportunities in Windermere.Set on Lake Bessie, this renovated residence offers panoramic water views, flexible living spaces, and true indoor-outdoor Florida living, a feature not commonly found in the current rental inventory. Many competing properties offer limited outdoor space or no water access; this home provides a lakefront setting with room to relax and entertain. The open-concept floor plan features a chef's kitchen with gas range, custom cabinetry, and premium finishes, flowing into spacious living and dining areas. Two first-floor ensuite bedrooms offer ideal flexibility for guests, home office, or multigenerational living. The second-floor primary suite provides a private retreat with elevated lake views. Outdoor features include a screened porch, landscaped yard, fire-pit area, and koi pond, creating a peaceful setting for everyday living or entertaining. Located in Downtown Windermere, this home offers golf-cart-friendly access to local shops, weekly farmers markets, and community events, with convenient proximity to Orlando's major employment centers, top-rated schools, and world-class attractions including Disney and Universal. Rarely available as a rental, this lakeview property combines location, space, and lifestyle in one of Central Florida's most sought-after communities. Schedule your private showing today.

Application fee $50 / tenant over the age of 18. Additional fees - Cleaning Fee $1250. Pond Use and Maintenance at Tenants discretion and costs. Lease Terms - First month and Security Deposit. 12month Lease Term.
Sewer, Water, Landscaping included in Rent
311 E 8th Ave, Windermere, FL 34786 is a 5 bedroom, 4 bathroom, 3,805 sqft single-family home. It last sold for $800,000 on May 20, 2021 (13,233% above the $6,000 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $6,000 per month. That rental listing was removed on May 18, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,438,800, with a rent estimate of $6,074/month.

Home Details for 311 E 8th Ave

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Media

Comparable Sales for 311 E 8th Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1002 OAKDALE STREET, Windermere, FL
0.24
Single-Family Home
$890,000
08/11/26
4
3
3,516 sqft
725 OAKDALE STREET, Windermere, FL
0.08
Single-Family Home
$1,000,000
08/28/26
3
2.5
2,795 sqft
735 OAKDALE STREET, Windermere, FL
0.08
Single-Family Home
$910,000
05/09/26
3
2.5
2,475 sqft
830 OAKDALE STREET, Windermere, FL
0.14
Single-Family Home
$1,700,000
10/10/25
4
4.5
3,670 sqft
616 MAGNOLIA STREET, Windermere, FL
0.13
Single-Family Home
$830,000
10/27/25
4
2
2,582 sqft
316 E 5TH AVENUE, Windermere, FL
0.22
Single-Family Home
$1,050,000
05/21/26
4
3
2,412 sqft
606 E 6TH AVENUE, Windermere, FL
0.16
Single-Family Home
$2,175,000
06/18/26
4
4.5
4,471 sqft
1020 OAKDALE STREET, Windermere, FL
0.26
Single-Family Home
$2,171,470
04/29/26
5
4.5
3,994 sqft
412 FOREST STREET, Windermere, FL
0.41
Single-Family Home
$765,000
07/30/26
5
2.5
2,539 sqft
109 E 12TH AVENUE, Windermere, FL
0.37
Single-Family Home
$1,150,000
08/28/26
4
3.5
2,791 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Rental Market Trends in Windermere

Last updated Sep 2026
Trulia Rent Estimate$6,074/mo
Average rent
$2.95K
$100MoM
Available listings
129
View rental market trends in Windermere, FL

Around this home

View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Windermere

At least 271 Trulia users voted on each feature.

  • 93 % Say it's dog friendly

  • 92 % Say there are sidewalks

  • 87 % Say car is needed

  • 87 % Say parking is easy

  • 81 % Say people would walk alone at night

  • 80 % Say it's quiet

  • 80 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 75 % Say streets are well-lit

  • 64 % Say yards are well-kept

  • 60 % Say they plan to stay for at least 5 years

  • 59 % Say it's walkable to grocery stores

  • 56 % Say there's wildlife

  • 55 % Say it's walkable to restaurants

  • 54 % Say neighbors are friendly

  • 40 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Anjalique Creative Concepts
    "We’ve lived in this area for 5 years and absolutely love it! The people in the community are always friendly, welcoming and supportive of one another. All the surrounding neighborhoods are well maintained and there are always organized activities in the community that makes it fun to meet new residents moving in."
    0
    Flag
  • Snkdrwbwms
    "Very safe area. Police is very present and effective. Amazing place to live. I will definitely be here forever."
    0
    Flag
  • Valentina
    "Trick or treating is big but it’s more about small groups of neighbors doing things together rather than large activities in the entire neighborhood."
    0
    Flag
  • Juliana Daurio
    "I moved to Windermere in 2004. When my kids were 3 and 4. This feels like home since then. Now that my kids are gone I see no need to move. I have many nice neighbors and enjoy everything that this area has to offer. "
    0
    Flag
  • Snkdrwbwms
    "Great neighborhood! I live here for 12 years and intend to stay. Very safe with great administrative support from the HOA. "
    0
    Flag
  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
    Flag
  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
    Flag
  • Datylberman
    "I work at home so I’m not versed in the commute anywhere.many people in Windermere work at hone also.friends who work downtown are happy with their commute."
    0
    Flag
  • John Malloy
    "Work from home Commute to stores, health care, friendly community. Safe and secure in my neighborhood. "
    0
    Flag
  • Garrett Hendrickson
    "Some home owners don’t want neighbors dogs to relieve themselves in their yard. This is even if you clean up after your pet. "
    0
    Flag
  • Ngandhi62
    "Great areas to walk dogs and great puppy parks. Very close convenient veterinarians and pet supply stores. There are also many pet owners in area, therefore a nice social community is created."
    5
    Flag
  • Sean H.
    "It is a very pet friendly neighborhood. And has many fenced in dog areas and 90% of people are respectful enough to clean up after their dogs."
    3
    Flag
  • Limegreenlilo
    "Quiet & neighbors look out for one another. We have a FB page for residents to help each other out. I have been a resident ten years and love living here. HOA is good and they keep everything nice."
    0
    Flag
  • Carylpalmerini17
    "Great place to raise children and just enjoy life. Schools are amazing and the 4th is no joke. Get a move on ....."
    3
    Flag
  • Carylpalmerini17
    "Great place to live in. Everyone has been kind, neighborhood is well kept, activities are always taking place. "
    3
    Flag
  • Shariel A.
    "tons of baggies available. tons of space and good clean environment for your pets. worth living for safety and pet compliance. "
    1
    Flag
  • Msldancer
    "See lots of dogs in the area, most are very social. But I do not like that some owners do not put their dogs on leashes, they also then get mad when you come by even though you’re dog is leashes as it should be."
    2
    Flag
  • Mckenziejl
    "They would like the many trails and dog parks. Most of the neighborhoods are not gated or man guarded, so you can easily move in and out of them. Each neighborhood is unique and wherher you're going for walk with or without you pet, the time would be enjoyable."
    0
    Flag
  • Jessica
    "30min or less to get to any of the central Florida locations. Some locations can even see fireworks. Traffic can be a little heavy during the am/pm rush but nothing super crazy."
    2
    Flag
  • Stephanie F.
    "Easy to get to Disney. I work on Disney property. High traffic during rush hour times. Very quick during non peak rush hour times. "
    1
    Flag
  • Afanador713
    "Great parks for families to bike, walk and enjoy a picnic. The area is beautiful, homes are very well cared for."
    0
    Flag
  • Saige L.
    "Lot of area to walk the dogs on leashes. Not so many dog parks are available where they can run free. "
    0
    Flag
  • David M.
    "I’ve lived in Windermere for 3+ years and absolutely love it! Great schools, homes and atmosphere! Wouldnt live in any other neighborhood! "
    0
    Flag
  • Jessica
    "lots of families and super safe and pet friendly. also super active community and lots of greenspace to excercise in. "
    2
    Flag
  • Fabiana B.
    "Great family neighborhood. Great Lakes for water activities. Good for walking with your family, pet or go for a bike ride. "
    1
    Flag
  • Dasom.jang
    "It’s a nice and safe area to live in. There isn’t much going on, but there are food truck nights once a month, and farmer’s market on every Saturday in Winter Garden. "
    0
    Flag
  • John F.
    "I have lived in Windermere for 20 years. Very safe and good clean people. The cops are very responsive and people are rich and have class "
    0
    Flag
  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
    Flag
  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
    Flag
  • Evelyn T.
    "It’s a small oasis away from the hustle and bustle of such a vacation heavy town. I love getting to feel like I’m actually away from work and in a calm space but still be a 20 minute commute."
    1
    Flag
  • Alex P.
    "Great neighborhood. Family oriented. Great schools. Affluent, but not overly pretentious. Not much to in town. "
    0
    Flag
  • Jessica M.
    "Great neighborhood, great people, great atmosphere. I always love visiting this area. Communities are kept clean and look inviting. "
    1
    Flag
  • Jamesgkoshy
    "Quiet neighborhood, that is short distance to major attractions. Safe with great schools. Beautiful, clean and uncrowded. "
    0
    Flag
  • Loypippin
    "It’s a safe area but growing too quickly. Too many new houses and schools getting crowded. The schools are great, but need to be built faster to keep up. "
    1
    Flag
  • Beverly B.
    "It is very safe well lighted small community with many families with and without children. Everyone is friendly and keep their properties in great shape"
    0
    Flag
  • Joanna T.
    "Accessibility, close to highways, malls, restaurants. the community is safe and they have frequent events for the family"
    1
    Flag
  • Princess J.
    "Great place to live, and I feel safe in this area. I moved to this area when I moved to Florida and it was the best decision. "
    1
    Flag
  • Windy
    "Nice , clean , safe area . Okay with my kids playing out side with other kids. Nice pool area friendly people . "
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 18, 2026
Source: Zillow Rentals
ListingRemoved
$6,000
Apr 1, 2026
Source: Stellar MLS #O6333319
ListingRemoved
$1,549,000
Mar 17, 2026
Source: Zillow Rentals
Listed For Rent
$6,000
Mar 17, 2026
Source: Stellar MLS #O6364016
ListingRemoved
$6,000
Mar 17, 2026
Source: Stellar MLS #O6364016
PriceChange
$6,000
Price decreased by 100%

Frequently asked questions about 311 E 8th Ave

  • What is 311 E 8th Ave estimated to be worth?
    Trulia's estimated value for 311 E 8th Ave in Windermere, FL is $1,438,800.
  • What is the price history for 311 E 8th Ave?
    311 E 8th Ave in Windermere, FL last sold for $800,000 in May 2021.
  • Is Windermere a buyer's or seller's market?
    Windermere is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Windermere?
    The median sale price in Windermere is $856K. That is up $41.5K from the prior month.
  • Does 311 E 8th Ave have air conditioning?
    Yes, 311 E 8th Ave in Windermere, FL has air conditioning.
  • Does 311 E 8th Ave have laundry facilities?
    Yes, 311 E 8th Ave in Windermere, FL has in-unit laundry.

Homes for rent near 311 E 8th Ave

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item