2829 Windsor Hill Dr, Windermere, FL 34786
Property image
Property image
OFF MARKET

2829 Windsor Hill Dr
Windermere, FL 34786

  • 4 Beds
  • 3.5 Baths
  • 3,267 sqft (on 1 acre)

$1,012,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $7,090/mo*
Refinance Your Home

$1,012,700

Trulia Estimate
as of Aug 22, 2026
Est. Refi. Payment $7,090/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,267 sqft
(on 1 acre)

Home Value

Trulia Estimate
$1.01M
Since last month
Decreased$16K (-1.6%)
Since last year
Increased$27K (+2.7%)
Since last sale
Increased$486K (+92.6%)
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 +74% in the last 10 years
MonthEstimated value
2026
August 2026$1.01M
July 2026$1.03M
June 2026$1.03M
May 2026$1.03M
April 2026$1.02M
March 2026$1.02M
February 2026$1.03M
January 2026$1M
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
2806 WINDSOR HILL DRIVE, Windermere, FL
0.07
Single-Family Home
$1,040,000
06/12/26
4
3
3,181
2722 PARK ROYAL DRIVE, Windermere, FL
0.17
Single-Family Home
$950,000
04/20/26
4
3
2,967
2722 INGEBORG COURT, Windermere, FL
0.45
Single-Family Home
$850,000
08/10/26
4
2.5
2,619
9641 CROWN PRINCE LANE, Windermere, FL
0.47
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
3138 SEIGNEURY DRIVE, Windermere, FL
0.37
Single-Family Home
$1,175,000
05/22/26
4
4.5
3,831
2641 HEMPEL AVENUE, Windermere, FL
0.49
Single-Family Home
$812,000
04/20/26
4
2
2,404
2828 INGEBORG COURT, Windermere, FL
0.46
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
2016 WHITFIELD LANE, Orlando, FL
0.45
Single-Family Home
$935,000
08/07/26
4
3
2,895
9495 WESTOVER CLUB CIRCLE, Windermere, FL
0.40
Single-Family Home
$830,000
02/27/26
4
3
2,773
9447 WESTOVER CLUB CIRCLE, Windermere, FL
0.46
Single-Family Home
$765,000
09/10/25
4
3
2,568

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
2818 WINDSOR HILL DRIVE, Windermere, FL 34786
0.06
$1,060,800
6
4.5
3,817
Off Market
2806 WINDSOR HILL DRIVE, Windermere, FL 34786
0.07
$1,040,000
4
3
3,181
Recently Sold
9506 KINGSBURY COURT, Windermere, FL 34786
0.11
$931,300
4
3
2,463
Off Market
9042 PINNACLE CIRCLE, Windermere, FL 34786
0.12
$3,229,100
7
5.5
8,461
Off Market
2746 PARK ROYAL DRIVE, Windermere, FL 34786
0.13
$908,500
5
3
2,878
Off Market
9542 KINGSBURY COURT, Windermere, FL 34786
0.15
$1,266,700
6
5.5
3,941
Off Market
9138 PINNACLE CIRCLE, Windermere, FL 34786
0.17
$1,213,800
4
4
3,808
Off Market
2722 PARK ROYAL DRIVE, Windermere, FL 34786
0.17
$950,000
4
3
2,967
Recently Sold
9012 PINNACLE CIRCLE, Windermere, FL 34786
0.17
$1,969,900
4
4.5
3,585
Off Market
9119 BALMORAL MEWS SQ, Windermere, FL 34786
0.17
$1,399,000
4
4
4,052
For Sale
9332 WINDY RIDGE ROAD, Windermere, FL 34786
0.21
$946,900
4
3.5
2,892
Off Market
9527 QUEENSBURY COURT, Windermere, FL 34786
0.21
$1,425,000
5
5
5,378
For Sale

Local Information

  • Map ViewExplore the area around 2829 Windsor Hill Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1994
Lot Size
1 acre
Living Area
3,267 sqft
Price/Sqft
$310
Parking
Garage

About this House

Opportunity awaits in one of Windermere's most sought-after locations. This estate home set on a full-acre with a sweeping circular drive beneath canopy oaks is ready to be transformed into the home of your dreams. Priced to sell and ready for renovation, this lovely home with unbeatable curb appeal and an excellent single-story floor plan has so much to offer. Boasting a split plan with 4 bedrooms plus a library/den and master retreat with mini-office or sitting area, this home is ready to impress. A large spacious foyer opens into separate formal living and dining spaces with French doors leading out to an oversized screened pool/spa deck enclosure. The kitchen and family room are generous in size. The fully-fenced backyard is shady and private. 3-car garage. Tile roof. Awesome location with easy access to 408/downtown Orlando, attractions, and Restaurant Row. Oh, and Thornebrooke Elementary! Priced below market value for a quick sale and to allow new buyer to customize this home that has tons of potential. Community has tennis courts and park.
2829 Windsor Hill Dr, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 3,267 sqft single-family home built in 1994. It last sold for $525,000 on Nov 13, 2017. It is currently off market. The Trulia Estimate is $1,012,700, with a rent estimate of $6,079/month.

Home Details for 2829 Windsor Hill Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: Stucco, WoodGardenPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1994Year Updated: 1994
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Additional Information

Intercom

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Nov 13, 2017
Source: N/A
Sold
$525,000
Sep 22, 2017
Source: Agent Provided
Listed For Sale
$550,000
May 26, 2005
Source: N/A
Sold
$595,000
May 6, 1996
Source: N/A
Sold
$347,000
Jun 8, 1994
Source: N/A
Sold
$349,000

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

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.
  • 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 2829 Windsor Hill Dr

  • What is 2829 Windsor Hill Dr estimated to be worth?
    Trulia's estimated value for 2829 Windsor Hill Dr in Windermere, FL is $1,012,700.
  • What is the price history for 2829 Windsor Hill Dr?
    2829 Windsor Hill Dr in Windermere, FL last sold for $525,000 in November 2017.
  • 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 2829 Windsor Hill Dr have air conditioning?
    Yes, 2829 Windsor Hill Dr in Windermere, FL has air conditioning.
  • Does 2829 Windsor Hill Dr have a pool?
    Yes, 2829 Windsor Hill Dr in Windermere, FL has a pool.

Explore by feature - Pet Friendly

49 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

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83 rentals with air conditioning in Windermere, FL

Explore by feature - Pool

80 rentals with a pool in Windermere, FL

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19 rentals with an outdoor space in Windermere, FL

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Off Market Homes Near 2829 Windsor Hill Dr

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