1069 W 2nd Ave, Windermere, FL 34786
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Property image
OFF MARKET

1069 W 2nd Ave
Windermere, FL 34786

  • 6 Beds
  • 7 Baths
  • 7,177 sqft (on 0.54 acres)

$4,204,200

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $28,906/mo*
Refinance Your Home

$4,204,200

Trulia Estimate
as of Aug 13, 2026
Est. Refi. Payment $28,906/mo*
Refinance Your Home
6 Beds
7 Baths
7,177 sqft
(on 0.54 acres)

Home Value

Trulia Estimate
$4.2M
Since last month
Decreased$107K (-2.5%)
Since last year
Increased$114K (+2.8%)
Since last sale
Increased$1M (+46.3%)
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 +50% in the last 10 years
MonthEstimated value
2026
August 2026$4.2M
July 2026$4.27M
June 2026$4.31M
May 2026$4.23M
April 2026$4.2M
March 2026$4.15M
February 2026$4.17M
January 2026$3.96M
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
805 W 2ND AVENUE, Windermere, FL
0.15
Single-Family Home
$4,125,000
09/05/25
5
5
4,783
800 W 2ND AVENUE, Windermere, FL
0.22
Single-Family Home
$2,400,000
09/05/25
5
4.5
5,511
105 PINE STREET, Windermere, FL
0.41
Single-Family Home
$2,335,000
06/10/26
5
5.5
5,696
409 W 2ND AVENUE, Windermere, FL
0.47
Single-Family Home
$2,250,000
03/09/26
5
4.5
4,688
11449 LAKE BUTLER BOULEVARD, Windermere, FL
0.30
Single-Family Home
$1,620,000
07/31/26
5
4
4,648
2828 MARQUESAS COURT, Windermere, FL
0.57
Single-Family Home
$2,500,000
01/05/26
6
5.5
6,819
2635 TRYON PLACE, Windermere, FL
0.52
Single-Family Home
$1,375,000
06/12/26
6
4.5
4,027
106 PALM STREET, Windermere, FL
0.45
Single-Family Home
$1,375,000
06/11/26
5
4.5
3,082
11018 LAKE BUTLER BOULEVARD, Windermere, FL
0.55
Single-Family Home
$3,100,000
09/02/25
4
3.5
3,923
11303 WINDERMERE ROAD, Windermere, FL
0.91
Single-Family Home
$2,550,000
06/22/26
5
5
5,277

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
805 W 2ND AVENUE, Windermere, FL 34786
0.15
$4,108,100
5
5
4,783
Off Market
803 W 2ND AVENUE, Windermere, FL 34786
0.17
$2,365,900
4
3.5
2,819
Off Market
801 W 2ND AVENUE, Windermere, FL 34786
0.18
$3,508,600
5
6
5,639
Off Market
800 W 2ND AVENUE, Windermere, FL 34786
0.22
$5,999,000
5
4.5
5,511
For Sale
11606 LAKE BUTLER BOULEVARD, Windermere, FL 34786
0.24
$5,121,000
6
7
7,400
Off Market
11539 LAKE BUTLER BOULEVARD, Windermere, FL 34786
0.27
$3,300,000
5
5
5,018
For Sale
724 W 2ND AVENUE, Windermere, FL 34786
0.31
$7,500,000
6
7.5
6,874
For Sale
12 PINE STREET, Windermere, FL 34786
0.31
$3,979,500
4
4.5
4,313
Off Market
11449 LAKE BUTLER BOULEVARD, Windermere, FL 34786
0.30
$1,620,000
5
4
4,648
Recently Sold
8 PINE STREET, Windermere, FL 34786
0.32
$3,816,000
5
5
5,639
Off Market
3328 WAX BERRY COURT, Windermere, FL 34786
0.36
$900,000
4
4
2,636
For Sale
105 PINE STREET, Windermere, FL 34786
0.41
$2,335,000
5
5.5
5,696
Recently Sold

Local Information

  • Map ViewExplore the area around 1069 W 2nd Ave.
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2007
Lot Size
0.54 acres
Living Area
7,177 sqft
Price/Sqft
$586
Parking
Garage

About this House

Luxury and elegance resonate throughout this exquisite French Provincial estate located in the heart of Downtown Windermere. From the custom millwork, to the hand carved wood beams, custom ceiling details, and the wood inlayed marble flooring, no expense was spared in the construction of this architectural masterpiece. The chef in the family will fall in love with the kitchen featuring a massive center island, two chandeliers, exotic granite counter tops, and top of the line appliances from Wolf, Sub Zero, and Meile. The spacious master retreat includes a separate sitting area with a wall of windows overlooking the lake, a morning bar, private fitness room, and a spa bath with a steam shower and a huge garden tub with a view of the water. There is also a large dressing room with a center island and a private court yard with a hot tub for soaking away the stresses of a long day. Additional interior amenities include a nanny's quarters with access to a separate garage and a second floor with two en-suite bedrooms, a game room, a loft, and an outdoor balcony overlooking Wauseon Bay. Exterior features include a large half acre lot, 140 feet of unobstructed shoreline, a covered dock with a boat lift, screened summer kitchen, and a refreshing pool for cooling off in the hot summer sun. This is your opportunity to live on one of downtown Windermere most sought after streets.
1069 W 2nd Ave, Windermere, FL 34786 is a 6 bedroom, 8 bathroom, 7,177 sqft single-family home built in 2007. It last sold for $2,873,400 on Jun 15, 2018. It is currently off market. The Trulia Estimate is $4,204,200, with a rent estimate of $6,615/month.

Home Details for 1069 W 2nd Ave

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
AtticTypes of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Other, Hardwood

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.54 acres

Price and Tax history

DateEventPrice
Jun 15, 2018
Source: Stellar MLS #O5555237
Sold
$2,873,400
Feb 24, 2018
Source: Agent Provided
PriceChange
$2,890,000
Price decreased by 4%
Aug 22, 2017
Source: Agent Provided
PriceChange
$2,995,000
Price decreased by 5%
Jul 18, 2017
Source: Agent Provided
PriceChange
$3,150,000
Price decreased by 1%
Apr 6, 2017
Source: Agent Provided
PriceChange
$3,195,000
Price decreased by 2%

Market trends in Windermere

Last updated July 2026
Buyer'sMarketSeller'sMarket
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
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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
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  • 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
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  • 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
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  • 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
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  • 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
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  • Anthony G.
    "People are very family oriented. Neighbors came about the appearance and condition of their property."
    0
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  • Jessica
    "There are so many open spaces and intermittent dog poop stations which are always stocked. There is even a small dog park."
    0
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  • 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
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  • 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
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Apartments for Rent

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Explore by feature - Pet Friendly

51 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

73 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

88 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

89 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

81 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

25 rentals with an outdoor space in Windermere, FL

Homes for sale near 1069 W 2nd Ave

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Off Market Homes Near 1069 W 2nd Ave

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Frequently asked questions about 1069 W 2nd Ave

  • What is 1069 W 2nd Ave estimated to be worth?
    Trulia's estimated value for 1069 W 2nd Ave in Windermere, FL is $4,204,200.
  • What is the price history for 1069 W 2nd Ave?
    1069 W 2nd Ave in Windermere, FL last sold for $2,873,400 in June 2018.
  • 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 1069 W 2nd Ave have air conditioning?
    Yes, 1069 W 2nd Ave in Windermere, FL has air conditioning.
  • Does 1069 W 2nd Ave have a pool?
    Yes, 1069 W 2nd Ave in Windermere, FL has a pool.