2865 Windsor Hill Dr, Windermere, FL 34786
Family Room
Master Bedroom
OFF MARKET

2865 Windsor Hill Dr
Windermere, FL 34786

  • 7 Beds
  • 4.5 Baths
  • 5,003 sqft (on 1.16 acres)

$1,709,000

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $11,912/mo*
Refinance Your Home

$1,709,000

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $11,912/mo*
Refinance Your Home
7 Beds
4.5 Baths
5,003 sqft
(on 1.16 acres)

Home Value

Trulia Estimate
$1.71M
Since last month
Decreased$4K (-0.3%)
Since last year
Increased$28K (+1.6%)
Since last sale
Increased$959K (+127.9%)
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 +79% in the last 10 years
MonthEstimated value
2026
August 2026$1.71M
July 2026$1.71M
June 2026$1.73M
May 2026$1.71M
April 2026$1.71M
March 2026$1.73M
February 2026$1.72M
January 2026$1.66M
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
9011 PINNACLE CIRCLE, Windermere, FL
0.31
Single-Family Home
$1,875,000
07/31/26
5
5
6,546
3138 SEIGNEURY DRIVE, Windermere, FL
0.25
Single-Family Home
$1,175,000
05/22/26
4
4.5
3,831
2828 INGEBORG COURT, Windermere, FL
0.44
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
9641 CROWN PRINCE LANE, Windermere, FL
0.55
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
2806 WINDSOR HILL DRIVE, Windermere, FL
0.17
Single-Family Home
$1,040,000
06/12/26
4
3
3,181
2722 PARK ROYAL DRIVE, Windermere, FL
0.19
Single-Family Home
$950,000
04/20/26
4
3
2,967
2722 INGEBORG COURT, Windermere, FL
0.46
Single-Family Home
$850,000
08/10/26
4
2.5
2,619
9439 WESTOVER CLUB CIRCLE, Windermere, FL
0.57
Single-Family Home
$1,099,995
10/24/25
6
4.5
4,445
8225 LYNCH DRIVE, Orlando, FL
0.47
Single-Family Home
$983,850
05/22/26
5
4.5
3,756
2016 WHITFIELD LANE, Orlando, FL
0.48
Single-Family Home
$935,000
08/07/26
4
3
2,895

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
3036 SEIGNEURY DRIVE, Windermere, FL 34786
0.13
$1,760,000
4
4
4,287
Off Market
9332 WINDY RIDGE ROAD, Windermere, FL 34786
0.11
$946,900
4
3.5
2,892
Off Market
3037 SEIGNEURY DRIVE, Windermere, FL 34786
0.16
$2,612,400
6
5.5
6,601
Off Market
3049 SEIGNEURY DRIVE, Windermere, FL 34786
0.18
$2,393,700
6
5.5
6,553
Off Market
3014 PORTO LAGO COURT, Windermere, FL 34786
0.17
$2,540,500
6
7
6,419
Off Market
2746 PARK ROYAL DRIVE, Windermere, FL 34786
0.14
$908,500
5
3
2,878
Off Market
9138 PINNACLE CIRCLE, Windermere, FL 34786
0.17
$1,213,800
4
4
3,808
Off Market
2818 WINDSOR HILL DRIVE, Windermere, FL 34786
0.15
$1,060,800
6
4.5
3,817
Off Market
3126 SEIGNEURY DRIVE, Windermere, FL 34786
0.23
$1,909,400
5
4.5
5,002
Off Market
2806 WINDSOR HILL DRIVE, Windermere, FL 34786
0.17
$1,040,000
4
3
3,181
Recently Sold
9042 PINNACLE CIRCLE, Windermere, FL 34786
0.19
$3,229,100
7
5.5
8,461
Off Market
2722 PARK ROYAL DRIVE, Windermere, FL 34786
0.19
$950,000
4
3
2,967
Recently Sold

Local Information

  • Map ViewExplore the area around 2865 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
2005
Lot Size
1.16 acres
Living Area
5,003 sqft
Price/Sqft
$342
Parking
Garage

About this House

Beautiful corner lot in an area of large custom homes close to Isleworth in Windermere. A solid quality home built to owner's taste with stunning features and elegant decor. Enter into a wide bright two-story foyer through the double entry doors, into an impressive living space with tall top-lit, decorative inset arches and stately columns defining the formal dining room overlooking the spacious backyard and patio through the Oversize Windows and French Doors. Crown moldings, tray ceilings and beautiful chandeliers adorn this elegant and homely and nicely Pass by the butler's pantry/pull-up Wet-bar to enter the large fully-equipped kitchen with wood cabinetry, steel appliances, large Centre island and Solid surfaces. A large eat-in area with enough counter space on the breakfast bar to make entertaining a breeze. A over-size Master suite, adjacent to a library/office a guest suite together with an indoor utility area with doggie shower completes the first floor. Upstairs is a versatile loft area and balcony overlooking the formal living areas with 4 bedrooms and with walk-in closets. Owner willing to sell it with furniture. Makes a great second home for out of state/country buyers.
2865 Windsor Hill Dr, Windermere, FL 34786 is a 7 bedroom, 5 bathroom, 5,003 sqft single-family home built in 2005. It last sold for $750,000 on Jul 18, 2013. It is currently off market. The Trulia Estimate is $1,709,000, with a rent estimate of $7,750/month.

Home Details for 2865 Windsor Hill Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, RadiantAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Interior Details
AtticNumber of Rooms: 7Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Master Bath, Office, Recreation RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: Other, TileExterior: StuccoLawnPatioPorchSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 1.16 acres

Additional Information

Sport Court

Price and Tax history

DateEventPrice
Jul 18, 2013
Source: N/A
Sold
$750,000
Oct 6, 2012
Source: Agent Provided
Listed For Sale
$799,999
Jun 28, 2012
Source: Agent Provided
ListingRemoved
$888,888
Mar 24, 2012
Source: Agent Provided
PriceChange
$888,888
Price decreased by 1%
Mar 2, 2012
Source: Agent Provided
PriceChange
$899,862
Price decreased by 10%

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 2865 Windsor Hill Dr

  • What is 2865 Windsor Hill Dr estimated to be worth?
    Trulia's estimated value for 2865 Windsor Hill Dr in Windermere, FL is $1,709,000.
  • What is the price history for 2865 Windsor Hill Dr?
    2865 Windsor Hill Dr in Windermere, FL last sold for $750,000 in July 2013.
  • 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 2865 Windsor Hill Dr have air conditioning?
    Yes, 2865 Windsor Hill Dr in Windermere, FL has air conditioning.
  • Does 2865 Windsor Hill Dr have a pool?
    Yes, 2865 Windsor Hill Dr in Windermere, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

79 rentals with a pool in Windermere, FL

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Explore by feature - Outdoor Space

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Off Market Homes Near 2865 Windsor Hill Dr

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