8764 LOOKOUT POINTE DRIVE, Windermere, FL 34786
SOLD
JAN 20, 2026

$1,035,700

Trulia Estimate
  • 4 Beds
  • 3.5 Baths
  • 3,423 sqft

8764 LOOKOUT POINTE DRIVE, Windermere, FL 34786

Est. Refi. Payment $7,420/mo*
Refinance Your Home
Currently Off Market - Sold Jan 20, 2026 for $1,045,000 (4% below list price)

Home Value

Trulia Estimate
$1.04M
Since last month
Decreased$10K (-0.9%)
Since last year
Increased$26K (+2.5%)
Since last sale
Decreased$11K (-1%)
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 +114% in the last 10 years
MonthEstimated value
2026
September 2026$1.03M
August 2026$1.04M
July 2026$1.05M
June 2026$1.06M
May 2026$1.05M
April 2026$1.04M
March 2026$1.04M
February 2026$1.04M
January 2026$1.04M
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
8626 CRESCENDO AVENUE, Windermere, FL
0.19
Single-Family Home
$722,500
12/02/25
4
3.5
3,399
11903 CAVE RUN AVENUE, Windermere, FL
0.21
Single-Family Home
$725,000
07/10/26
4
3.5
3,413
11922 ANGLE POND AVENUE, Windermere, FL
0.24
Single-Family Home
$745,000
05/21/26
4
3.5
3,382
11849 CAVE RUN AVENUE, Windermere, FL
0.25
Single-Family Home
$740,000
01/08/26
4
3.5
3,414
11816 ANGLE POND AVENUE, Windermere, FL
0.30
Single-Family Home
$830,000
05/29/26
4
3.5
3,391
8776 CRESCENDO AVENUE, Windermere, FL
0.06
Single-Family Home
$619,000
12/18/25
3
2.5
2,072
8715 QUIET MEADOWS TRAIL, Windermere, FL
0.30
Single-Family Home
$814,500
07/31/26
4
3.5
3,388
9197 OUTLOOK ROCK TRAIL, Windermere, FL
0.35
Single-Family Home
$1,040,000
10/22/25
5
3.5
4,056
9257 OUTLOOK ROCK TRAIL, Windermere, FL
0.28
Single-Family Home
$879,900
07/10/26
5
4.5
3,619

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
8757 LOOKOUT POINTE DRIVE, Windermere, FL 34786
0.03
$719,600
4
3.5
3,452
Off Market
8776 CRESCENDO AVENUE, Windermere, FL 34786
0.06
$619,000
3
2.5
2,072
Recently Sold
8728 LOOKOUT POINTE DRIVE, Windermere, FL 34786
0.06
$960,900
4
3.5
3,600
Off Market
8799 CRESCENDO AVENUE, Windermere, FL 34786
0.11
$1,157,200
6
4.5
4,502
Off Market
8711 LOOKOUT POINTE DRIVE, Windermere, FL 34786
0.10
$748,100
4
3.5
3,419
Off Market
8712 CRESCENDO AVENUE, Windermere, FL 34786
0.11
$678,700
4
3.5
2,926
Off Market
8705 LOOKOUT POINTE DRIVE, Windermere, FL 34786
0.11
$782,300
4
3.5
3,304
Off Market
8931 LOOKOUT POINTE DRIVE, Windermere, FL 34786
0.19
$740,000
5
4
2,989
For Sale
8713 Crescendo Other City In The State, Florida, FL 34786
0.13
$780,000
3
2.5
-
For Sale
12016 OTTERBROOKE TRAIL, Windermere, FL 34786
0.17
$1,030,200
6
4.5
4,457
Off Market
9036 ARBORS EDGE TRAIL, Windermere, FL 34786
0.20
$824,100
4
3
2,835
Off Market

Local Information

  • Map ViewExplore the area around 8764 LOOKOUT POINTE DRIVE.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2015
3,423 sqft
$305/sqft
2 Car Garage
HOA $83/mo

About this House

What's unique:Pool bathroomCommunity pool and playgroundAbundant storagePutting green
Experience all the MAGIC that living in Windermere has to offer with DISNEY FIREWORK VIEWS from your private pool deck every night! Waterviews, Florida Pines, blue skies, and palm trees right in your own backyard. A true outdoor oasis with TRAVERTINE TILE pool deck, a shady covered lanai, pool and spa with water feature, a FENCED YARD, and a miniature golf PUTTING GREEN! Located in Windermere Trails you have access to a beautiful WALKING AND BIKING TRAIL behind your home that winds through the community green spaces and along Lake Reams to the community pool and playground. DOORSTEP TO DISNEY IN ABOUT TEN MINUTES! Windermere is one of the most comfortable and convenient neighborhoods to live in in Central Florida. Zoned for A-RATED SCHOOLS Bay Lake Elementary, Horizon West Middle, and Windermere High School. Windermere Preparatory Academy is nearby as well. BRAND NEW HVAC with UV light filter installed in 2025. Solar panels are PAID OFF saving you every month on your electric bill! Downstairs office. Open concept living. Pool bathroom. Shaded front porch. Upstairs is a large enclosed loft. A private balcony off the secondary bedroom. Lots of closets for good storage space. Great NATURAL LIGHT. The home is in fantastic condition. Lakeside Village Plaza is right outside the community with everything you need like Publix grocery and pharmacy, doctors offices, dental, ortho, eye, gym, pilates, sports medicine, Kid Strong, Rokkas Market, Chipotle, UPS, bars, Mavis Tire, daycares, banks, Starbucks, salons, restaurants and so much more. Thirty minutes to downtown Orlando and MCO.
8764 LOOKOUT POINTE DRIVE, Windermere, FL 34786 is a 4 bedroom, 4 bathroom, 3,423 sqft single-family home built in 2015. It last sold for $1,045,000 on Jan 20, 2026 (4% below the $1,085,000 asking price). More recently, it was listed as a rental in January 2026 with an asking price of $4,800 per month. That rental listing was removed on February 1, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,035,700, with a rent estimate of $4,395/month.
Last check for updates: about 5 hours ago
Listed by Ken Pozek, (407) 717-0197
REAL BROKER, LLC, (855) 450-0442
Brianna Sawyer, (407) 289-9271
REAL BROKER, LLC, (855) 450-0442
Bought with: Susan Heron, (404) 209-9029, HOMESMART, (407) 476-0451
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6350484
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 8764 LOOKOUT POINTE DRIVE

Interior Features

Interior Details
Number of Rooms: 6Types of Rooms: Primary Bedroom, Primary Bathroom, Family Room, Kitchen, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3423 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Water ConnectedAppliances: Dishwasher, Dryer, Microwave, Range, Refrigerator, WasherDishwasherDryerLaundry: Laundry Room,Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Gas & Electric
Electric: Photovoltaics Seller OwnedHas Electric on Property
Windows, Doors, Floors & Walls
Flooring: Ceramic Tile, Luxury Vinyl
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Ceramic Tile, Luxury Vinyl
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Other, SidewalkFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Pool
Pool: In GroundPool
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 40

Property Information

Year Built
Year Built: 2015
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 362327916203730

Price & Status

Price
List Price: $1,085,000Price Per Sqft: $305/sqft
Status Change & Dates
Off Market Date: Fri Dec 26 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: WINDERMERECommunity: WINDERMERE TRLS PH 3A
School Information
Elementary School: Bay Lake ElementaryJr High / Middle School: Horizon West Middle SchoolHigh School: Windermere High School

Building

Building Area
Building Area: 4136 Square Feet

Community

Community Features: Dog Park, Park, Playground, Pool, SidewalksNot Senior Community
Other
Playground

HOA

HOA Name: Jamie Stevens/Premiere Association ManagementHOA Phone: 352-432-3312Association for this Listing: Orlando RegionalHas an HOAHOA Fee: $83/Monthly

Lot Information

Lot Area: 6138 sqft

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6350484Back On Market Date: Fri Dec 12 2025Showing Requirements: Appointment Only, ShowingTimeUniversal Property Id: US-12095-N-362327916203730-R-N

Additional Information

Dog ParkParkPlaygroundPoolSidewalks

Price and Tax history

DateEventPrice
Feb 1, 2026
Source: HomeSmart
ListingRemoved
$4,800
Jan 24, 2026
Source: HomeSmart
Listed For Rent
$4,800
Jan 20, 2026
Source: Stellar MLS #O6350484
Sold
$1,045,000
Jan 2, 2026
Source: Stellar MLS #O6350484
Pending
$1,085,000
Dec 12, 2025
Source: Stellar MLS #O6350484
PendingToActive
$1,085,000

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

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
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  • 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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 8764 LOOKOUT POINTE DRIVE

  • What is 8764 LOOKOUT POINTE DRIVE estimated to be worth?
    Trulia's estimated value for 8764 LOOKOUT POINTE DRIVE in Windermere, FL is $1,035,700.
  • What is the price history for 8764 LOOKOUT POINTE DRIVE?
    8764 LOOKOUT POINTE DRIVE in Windermere, FL last sold for $1,045,000 in January 2026.
  • 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 8764 LOOKOUT POINTE DRIVE have air conditioning?
    Yes, 8764 LOOKOUT POINTE DRIVE in Windermere, FL has air conditioning.
  • Does 8764 LOOKOUT POINTE DRIVE have a pool?
    Yes, 8764 LOOKOUT POINTE DRIVE in Windermere, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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