83 Pine St, Windermere, FL 34786
Property image
Property image
OFF MARKET

$1,193,700

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 4,010 sqft (on 0.39 acres)

83 Pine St, Windermere, FL 34786

Est. Refi. Payment $8,767/mo*
Refinance Your Home
Currently Off Market - Sold Aug 26, 2016 for $465,000

Home Value

Trulia Estimate
$1.19M
Since last month
Decreased$37K (-3%)
Since last year
Increased$24K (+2%)
Since last sale
Increased$729K (+156.7%)
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 +156% in the last 10 years
MonthEstimated value
2026
September 2026$1.19M
August 2026$1.23M
July 2026$1.23M
June 2026$1.24M
May 2026$1.24M
April 2026$1.23M
March 2026$1.25M
February 2026$1.21M
January 2026$1.16M
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
106 PALM STREET, Windermere, FL
0.05
Single-Family Home
$1,375,000
06/11/26
5
4.5
3,082
299 W 4TH AVENUE, Windermere, FL
0.31
Single-Family Home
$862,000
01/08/26
4
3
2,410
412 FOREST STREET, Windermere, FL
0.37
Single-Family Home
$765,000
07/30/26
5
2.5
2,539
409 W 2ND AVENUE, Windermere, FL
0.10
Single-Family Home
$2,250,000
03/09/26
5
4.5
4,688
105 PINE STREET, Windermere, FL
0.04
Single-Family Home
$2,335,000
06/10/26
5
5.5
5,696
111 MAIN STREET, Windermere, FL
0.32
Single-Family Home
$849,000
07/01/26
3
2
2,272
65 OAKDALE STREET, Windermere, FL
0.40
Single-Family Home
$1,050,000
10/31/25
4
2
2,191
84 OAKDALE ST, Windermere, FL
0.35
Single-Family Home
$1,750,000
06/23/26
4
5
3,519
81 OAKDALE STREET, Windermere, FL
0.40
Single-Family Home
$2,200,000
07/31/26
5
4.5
4,284
20 OAKDALE STREET, Windermere, FL
0.38
Single-Family Home
$1,400,000
09/04/26
3
2.5
2,188

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
105 PINE STREET, Windermere, FL 34786
0.04
$2,335,000
5
5.5
5,696
Recently Sold
106 PALM STREET, Windermere, FL 34786
0.05
$1,375,000
5
4.5
3,082
Recently Sold
409 W 2ND AVENUE, Windermere, FL 34786
0.10
$2,250,000
5
4.5
4,688
Recently Sold
515 W 2ND AVENUE, Windermere, FL 34786
0.09
$3,300,000
4
5.5
3,966
For Sale
400 W 2ND AVENUE, Windermere, FL 34786
0.13
$884,100
3
2.5
2,346
Off Market
212 W 1ST AVENUE, Windermere, FL 34786
0.18
$1,600,000
4
2
2,627
For Sale
407 W 1ST AVENUE, Windermere, FL 34786
0.14
$2,710,400
6
5.5
4,091
Off Market
7 1ST COURT, Windermere, FL 34786
0.18
$2,777,500
4
3
3,149
Off Market
50 FOREST STREET, Windermere, FL 34786
0.20
$7,391,900
6
5.5
7,388
Off Market
226 FOREST STREET, Windermere, FL 34786
0.25
$787,700
3
2
1,532
Off Market
307 4TH AVENUE, Windermere, FL 34786
0.29
$1,218,700
4
3
3,190
Off Market
116 MAIN STREET, Windermere, FL 34786
0.27
$680,500
3
2
1,269
Off Market

Local Information

  • Map ViewExplore the area around 83 Pine St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1927
0.39 acre lot
4,010 sqft
$298/sqft

About this House

For all showings, questions & offers please contact "Ginna & Tim" (321) 663-4321. Welcome to 83 Pine Street! One of the most prestigious and coveted streets in Windermere. This home is located in the heart of Windermere which is situated among large mature oak trees and the renowned Butler Chain of Lakes. It is an easy stroll to the farmer's market, tennis courts for Windermere residents only, Allen's Ice Cream Parlor, and many other boutique stores nestled in the charming community of Windermere. The property also has access to the Town of Windermere's private boat ramps. Upon entering the property, you will be greeted by a beautiful oasis with a water feature, fire-pit, a large planter area, and beautiful outdoor kitchen which is perfect for entertaining. The first floor has an over sized remodeled kitchen with an extra-large pantry you have to see to believe. The bright and airy kitchen has many new appliances and a gas stove. There is a combo dining room/playroom/sitting area that leads to the large sunken living room adorned by a beautiful brick wood-burning fireplace. The first floor also boasts a large master or mother-in-law suite with a full bathroom and plenty of living and closet space. This room also has its own entrance that leads you into a beautiful garden and easy in-and-out access. Just steps away is a large, 20x12 newly built storage space. The second floor has 3 bedrooms, including a master with a full bath that features a Jacuzzi tub and over-sized shower. The master has an attached 340 sq. ft. bonus room that can be used as a home office, nursery or theater room. This room also has its own private entrance. There are also 2 other spacious bedrooms, that share a full bath. Each bedroom boasts 2 closets. Transferable termite bond. Transferable Full Coverage Home Warranty from Old Republic Home Protection This is truly a unique home that reflects the essence of Windermere. Much of the home has been updated recently by current owners.
83 Pine St, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 4,010 sqft single-family home built in 1927. It last sold for $465,000 on Aug 26, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,193,700, with a rent estimate of $7,700/month.

Home Details for 83 Pine St

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Number of Rooms: 10Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, PantryCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
FireplaceJetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: BrickGardenLawnSprinkler System

Property Information

Year Built
Year Built: 1927Year Updated: 1985
Property Type / Style
Property Type: Single Family HomeArchitecture: Craftsman

Community

Units in Building: 1

Lot Information

Lot Area: 0.39 acres

Price and Tax history

DateEventPrice
Nov 13, 2020
Source: Agent Provided
ListingRemoved
$699,000
Oct 27, 2020
Source: Agent Provided
PriceChange
$699,000
Price decreased by 4%
Oct 12, 2020
Source: Agent Provided
PriceChange
$725,000
Price decreased by 5%
Sep 16, 2020
Source: Agent Provided
PriceChange
$765,000
Price decreased by 4%
Aug 14, 2020
Source: Agent Provided
PriceChange
$799,000
Price decreased by 3%

Market trends in Windermere

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$856K
$41.5KMoM
Sale-to-List Price
96.8%
0.4%MoM
Price per sq ft
$297
$5MoM
Available listings
274
22MoM

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

Frequently asked questions about 83 Pine St

  • What is 83 Pine St estimated to be worth?
    Trulia's estimated value for 83 Pine St in Windermere, FL is $1,193,700.
  • What is the price history for 83 Pine St?
    83 Pine St in Windermere, FL last sold for $465,000 in August 2016.
  • 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 83 Pine St have air conditioning?
    Yes, 83 Pine St in Windermere, FL has air conditioning.
  • Does 83 Pine St have laundry facilities?
    Yes, 83 Pine St in Windermere, FL has laundry facilities.

Explore by feature - Pet Friendly

54 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

68 rentals with a garage in Windermere, FL

Explore by feature - Air Conditioning

85 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

78 rentals with a pool in Windermere, FL

Explore by feature - Washer/dryer

92 rentals with a washer/dryer in Windermere, FL

Explore by feature - Outdoor Space

22 rentals with an outdoor space in Windermere, FL

Apartments for Rent

Skip to last item
Skip to first item

Off Market Homes Near 83 Pine St

Skip to last item
Skip to first item

Homes for sale near 83 Pine St

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item