20 Pine St
Windermere, FL 34786
- 5 Beds
- 4.5 Baths
- 4,534 sqft (on 1.38 acres)
5 Beds
4.5 Baths
4,534 sqft
(on 1.38 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
2000
Lot Size
1.38 acres
Living Area
4,534 sqft
Price/Sqft
$618
Parking
Garage
About this House
This Exceptional Butler Chain property sits on Bumby point with Wauseon bay views from the front and rear of the house. Amazing lake views from almost every room in the home. Property underwent an extensive makeover in 2013 with new kitchen and high end appliances. Within the last 2 years the property has received a new seawall with a 50 yr warranty, new composite decking to the dock and a whole house generator system also all the patio deck and balconies in stone have just been replaced. The home is a split level property with a fifth bedroom in the basement being used as a TV room which adds a further 321 sq foot to the property not included in the appraisal measure, 1 bedroom and a library on the first floor and the master, 2 additional bedrooms and an original British pub and games room located on the second floor. Boat on Dock and some contents of the house available for sale separately.
20 Pine St, Windermere, FL 34786 is a 5 bedroom, 5 bathroom, 4,534 sqft single-family home built in 2000. It last sold for $1,600,000 on May 9, 2019. It is currently off market. The Trulia Estimate is $2,800,600, with a rent estimate of $7,932/month.
Home Details for 20 Pine St
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Heating & Cooling Heating: Forced Air, ElectricCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 3Floors: Other, Hardwood |
Interior Details Types of Rooms: Walk In Closet, Breakfast Nook, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, Pantry, Recreation RoomWet BarCeiling Fan |
Appliances & Utilities DishwasherDisposalDryerMicrowaveWasher |
Fireplace & Spa Fireplace |
Windows, Doors, Floors & Walls Double Paned Windows |
Security Security System |
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Exterior Home Features Roof: TileDeckExterior: Stone, StuccoLawnPatio |
Parking & Garage GarageParking Spaces: 8Parking: Garage Attached |
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Year Built Year Built: 2000Year Updated: 2000 |
Property Type / Style Property Type: Single Family Home |
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Units in Building: 1 |
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Lot Area: 1.38 acres |
Price History for 20 Pine St
| Date | Price | Event | Source |
|---|---|---|---|
| 05/09/2019 | $1,600,000 | Sold | N/A |
| 04/01/2019 | $1,595,000 | Listed For Sale | Agent Provided |
| 01/31/2013 | $750,000 | Sold | N/A |
| 03/11/1998 | $257,500 | Sold | N/A |
Market trends in Windermere
Last updated June 2026
Avg. sale price
$722K
$50KMoM
Sale-to-List Price
97.3%
0.2%MoM
Price per sq ft
$273
$11MoM
Available listings
285
6MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $23,169 |
| Assessment | $1,879,557 |
Home facts updated by county records
Comparable Sales for 20 Pine St
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.41 | Single-Family Home | $1,620,000 | 07/31/26 | 5 | 4 | 4,648 | |
0.27 | Single-Family Home | $2,250,000 | 03/09/26 | 5 | 4.5 | 4,688 | |
0.20 | Single-Family Home | $2,335,000 | 06/10/26 | 5 | 5.5 | 5,696 | |
0.30 | Single-Family Home | $3,100,000 | 09/02/25 | 4 | 3.5 | 3,923 | |
0.22 | Single-Family Home | $1,375,000 | 06/11/26 | 5 | 4.5 | 3,082 | |
0.31 | Single-Family Home | $2,400,000 | 09/05/25 | 5 | 4.5 | 5,511 | |
0.49 | Single-Family Home | $1,375,000 | 06/12/26 | 6 | 4.5 | 4,027 | |
0.44 | Single-Family Home | $880,000 | 06/17/26 | 5 | 3.5 | 3,166 | |
0.26 | Single-Family Home | $4,125,000 | 09/05/25 | 5 | 5 | 4,783 | |
0.65 | Single-Family Home | $1,999,000 | 06/23/26 | 5 | 4 | 3,649 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 20 Pine St.
What Locals Say about Windermere
At least 270 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
79 % 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
Apartments for Rent
Homes for sale near 20 Pine St
Off Market Homes Near 20 Pine St
Frequently asked questions about 20 Pine St
- What is 20 Pine St estimated to be worth?Trulia's estimated value for 20 Pine St in Windermere, FL is $2,800,600.
- What is the price history for 20 Pine St?20 Pine St in Windermere, FL last sold for $1,600,000 in May 2019.
- 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 $722K. That is up $50K from the prior month.
- Does 20 Pine St have air conditioning?Yes, 20 Pine St in Windermere, FL has air conditioning.
- Does 20 Pine St have laundry facilities?Yes, 20 Pine St in Windermere, FL has in-unit laundry.

