808 Main St
Windermere, FL 34786
- 3 Beds
- 4 Baths
- 4,847 sqft (on 1.49 acres)
3 Beds
4 Baths
4,847 sqft
(on 1.49 acres)
Home Value
Trulia Estimate
$3.19MSince last month
Increased$26K (+0.8%)Since last year
Increased$220K (+7.4%)Since last sale
Increased$2M (+106%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +75% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| August 2026 | $3.19M |
| July 2026 | $3.17M |
| June 2026 | $3.2M |
| May 2026 | $3.2M |
| April 2026 | $3.16M |
| March 2026 | $3.18M |
| February 2026 | $3.14M |
| January 2026 | $3.06M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.42 | Single-Family Home | $2,175,000 | 06/18/26 | 4 | 4.5 | 4,471 | |
0.28 | Single-Family Home | $2,350,000 | 10/14/25 | 6 | 5.5 | 4,599 | |
0.14 | Single-Family Home | $1,700,000 | 10/10/25 | 4 | 4.5 | 3,670 | |
0.58 | Single-Family Home | $2,075,000 | 02/09/26 | 3 | 3 | 2,681 | |
0.15 | Single-Family Home | $975,000 | 10/20/25 | 3 | 3 | 2,353 | |
0.64 | Single-Family Home | $1,295,000 | 08/04/26 | 3 | 2.5 | 3,021 | |
0.07 | Single-Family Home | $850,000 | 10/21/25 | 3 | 2 | 2,778 | |
0.18 | Single-Family Home | $910,000 | 05/09/26 | 3 | 2.5 | 2,475 | |
0.23 | Single-Family Home | $2,171,470 | 04/29/26 | 5 | 4.5 | 3,994 | |
0.20 | Single-Family Home | $890,000 | 08/11/26 | 4 | 3 | 3,516 |
Nearby home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.06 | $3,598,500 | 4 | 5 | 6,079 | Off Market | |
0.05 | $10,200,000 | 6 | 8.5 | 6,457 | For Sale | |
0.07 | $849,500 | 3 | 2 | 2,778 | Off Market | |
0.11 | $1,434,800 | 4 | 5 | 3,191 | Off Market | |
0.11 | $1,014,700 | 3 | 3 | 2,412 | Off Market | |
0.11 | $2,052,700 | 5 | 4 | 3,950 | Off Market | |
0.14 | $1,045,800 | 5 | 2.5 | 2,971 | Off Market | |
0.15 | $974,300 | 3 | 3 | 2,353 | Off Market | |
0.13 | $1,375,800 | 4 | 6 | 3,753 | Off Market | |
0.14 | $1,697,600 | 4 | 4.5 | 3,670 | Off Market | |
0.14 | $2,046,500 | 4 | 4.5 | 3,917 | Off Market | |
0.14 | $2,170,000 | 6 | 5 | 5,031 | For Sale |
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2004
Lot Size
1.49 acres
Living Area
4,847 sqft
Price/Sqft
$658
Parking
Garage
About this House
HGTV Ready...all the work has already been done!! MILLION DOLLAR interior renovation and $500,000 exterior improvements. Located in downtown Windermere, Western facing on Lake Butler, on the famed Butler Chain of Lakes, this trophy property is a rare find! The design of the home recently featured on Houzz perfectly marries modern design with rustic farmhouse features that make it truly one-of-a-kind! Features include: 3 bedrooms, 3 full bathrooms, 2 half baths, bonus room, office, and a 3-car garage. From the award winning gourmet kitchen to the breathtaking lake views in just about every room, this house is filled with architectural details that are sure to impress. Exquisite master bath with dual sink vanity, large marble tile walk-in shower with soaking tub, down to the waterfront dining room with exposed beam ceilings, and custom cabinetry, the use of re-purposed barn wood, river stone fireplace and the antique doors that lead to a lower level room perfect for a wine cellar, add character to this unique home. The outdoor area is an entertainer's dream, with an outdoor bar, gazebo, resort-style swimming pool with infinity edge, and paver pool deck. Complete with dock and covered boat lift, and a sought after sandy beach, this home was created for those that want to live the ideal Florida lifestyle. Located just 20 minutes from Walt Disney World Resort, 30 minutes from downtown Orlando, and 40 minutes from Orlando International Airport, this is a home that comes along for sale once in a lifetime!
808 Main St, Windermere, FL 34786 is a 3 bedroom, 5 bathroom, 4,847 sqft single-family home built in 2004. It last sold for $1,549,000 on Mar 31, 2010. It is currently off market. The Trulia Estimate is $3,191,600, with a rent estimate of $7,617/month.
Home Details for 808 Main St
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Heating & Cooling Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2Floors: Tile, Carpet, Hardwood |
Interior Details Types of Rooms: Walk In ClosetWet BarCeiling Fan |
Appliances & Utilities Cable ReadyDishwasherDisposalRefrigerator |
Fireplace & Spa FireplaceHot Tub or Spa |
Security Security System |
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Exterior Home Features Roof: CompositionDeckExterior: OtherPatioPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 3Parking: Garage Attached |
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Year Built Year Built: 2004Year Updated: 2004 |
Property Type / Style Property Type: Single Family Home |
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Units in Building: 1 |
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Lot Area: 1.49 acres |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Feb 24, 2020 Source: Agent Provided | ListingRemoved | $3,300,000 |
Sep 23, 2019 Source: Agent Provided | Listed For Sale | $3,300,000 |
Apr 10, 2019 Source: Agent Provided | ListingRemoved | $3,300,000 |
Jan 29, 2019 Source: Agent Provided | Listed For Sale | $3,300,000 |
Mar 31, 2010 Source: N/A | Sold | $1,549,000 |
Dec 3, 2009 Source: Agent Provided | ListingRemoved | $1,598,000 |
Jul 1, 2009 Source: Agent Provided | PriceChange | $1,800,000 Price decreased by 10% |
Feb 16, 2009 Source: Agent Provided | Listed For Sale | $1,999,999 |
Jan 22, 1998 Source: N/A | Sold | $436,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2024 | $29,616 | $2,154,735 |
Home facts updated by county records
Market trends in Windermere
Last updated July 2026
Avg. sale price
$814K
$92.5KMoM
Sale-to-List Price
97.2%
0.1%MoM
Price per sq ft
$292
$18MoM
Available listings
296
11MoM
Around this home
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Frequently asked questions about 808 Main St
- What is 808 Main St estimated to be worth?Trulia's estimated value for 808 Main St in Windermere, FL is $3,191,600.
- What is the price history for 808 Main St?808 Main St in Windermere, FL last sold for $1,549,000 in March 2010.
- 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 $814K. That is up $92.5K from the prior month.
- Does 808 Main St have air conditioning?Yes, 808 Main St in Windermere, FL has air conditioning.
- Does 808 Main St have a pool?Yes, 808 Main St in Windermere, FL has a pool.

