2865 Windsor Hill Dr, Windermere, FL 34786
OFF MARKET

2865 Windsor Hill Dr
Windermere, FL 34786

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

$1,741,400

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $11,935/mo*
Refinance Your Home

$1,741,400

Trulia Estimate
as of May 25, 2026
Est. Refi. Payment $11,935/mo*
Refinance Your Home
7 Beds
4.5 Baths
5,003 sqft
(on 1.16 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Porch, Patio, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 2865 Windsor Hill Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, Other, 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 History for 2865 Windsor Hill Dr

DatePriceEventSource
07/18/2013$750,000Sold
N/A
10/06/2012$799,999Listed For SaleAgent Provided
06/28/2012$888,888ListingRemovedAgent Provided
03/24/2012$888,888PriceChange
Agent Provided
03/02/2012$899,862PriceChange
Agent Provided
01/11/2012$999,268PriceChange
Agent Provided
08/20/2011$999,862PriceChange
Agent Provided
09/25/2010$1,222,222Listed For SaleAgent Provided
07/08/2002$158,000Sold
N/A
06/18/2001$127,500Sold
N/A
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Property Tax and Assessment

Year2024
Tax$19,111
Assessment$1,291,421
Home facts updated by county records

Comparable Sales for 2865 Windsor Hill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
9502 Hempel Cove Blvd, Windermere, FL
0.37
Single-Family Home
$925,000
06/12/25
5
4.5
4,524
9138 Pinnacle Cir, Windermere, FL
0.17
Single-Family Home
$1,225,000
06/30/25
4
4
3,808
9501 Hempel Cove Blvd, Windermere, FL
0.35
Single-Family Home
$1,325,000
06/12/25
4
4
4,789
3138 Seigneury Dr, Windermere, FL
0.25
Single-Family Home
$1,175,000
05/22/26
4
4.5
3,831
2828 Ingeborg Ct, Windermere, FL
0.44
Single-Family Home
$1,220,000
01/23/26
5
4.5
3,190
9641 Crown Prince Ln, Windermere, FL
0.55
Single-Family Home
$1,070,000
09/30/25
5
4
3,924
2722 Park Royal Dr, Windermere, FL
0.19
Single-Family Home
$950,000
04/20/26
4
3
2,967
9538 Lavill Ct, Windermere, FL
0.47
Single-Family Home
$799,000
08/22/25
4
3
2,748
8208 Westminster Abbey Blvd, Orlando, FL
0.43
Single-Family Home
$925,000
05/27/25
5
4
3,741
9601 Ambleside Dr, Windermere, FL
0.59
Single-Family Home
$815,000
07/21/25
4
2.5
3,018

Nearby homes

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Assigned Schools

These are the assigned schools for 2865 Windsor Hill Dr.
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 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.
  • 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
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  • 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
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  • Snkdrwbwms
    "Easy to go everywhere. Sometimes traffic delays due to school drop off and pick up. I love to live here."
    0
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  • Juliana Daurio
    "Festivals , school events,Hallowed, Christmas and food truck events on Fridays in downtown Windermere "
    0
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  • 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
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  • 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
    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
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Homes for sale near 2865 Windsor Hill Dr

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2865 Windsor Hill Dr, Windermere, FL 34786 is a 7 bedroom, 5 bathroom, 5,003 sqft single-family home built in 2005. This property is not currently available for sale. 2865 Windsor Hill Dr was last sold on Jul 18, 2013 for $750,000. The current Trulia Estimate for 2865 Windsor Hill Dr is $1,741,400.