7729 Jailene Dr, Windermere, FL 34786
OFF MARKET

7729 Jailene Dr
Windermere, FL 34786

  • 3 Beds
  • 2.5 Baths
  • 1,644 sqft

$392,400

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $2,715/mo*
Refinance Your Home

$392,400

Trulia Estimate
as of Jun 27, 2026
Est. Refi. Payment $2,715/mo*
Refinance Your Home
3 Beds
2.5 Baths
1,644 sqft

Local Information

  • Map ViewExplore the area around 7729 Jailene Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautiful corner Townhouse in spectacular area and friendly neighborhood, Berkshire Place is at end of Berkshire park beautiful single homes subdivision.This townhouse was a model house in the first building built in 2007. Excellent interior design, all first floor is covered with ceramic tile, stair and second floor showing carpet in perfect condition. This has been a vacation home for a long time, the owner usually did use this townhouse for only 3 months per year the remaining time was vacant, only the last year has been rented fully furnished by a month to month contract. All appliances are in stainless steel, granite counter top in the kitchen and bathrooms. In front is a small lake with a forest reserve. The fireworks can be seen and enjoyed every night very close of this property. All schools for this address are the best of Orange county. This property has a car garage for two cars. This unit has a good size patio between the heated area and the car garage with paver flooring. The Association is in charge of the frontal garden and the lateral yard. Excellent ratio price-value and the best opportunity to get a property in consolidated area of Windermere. This price no included the furniture but is negotiable. No more search!, your new home inside of a big garden are waiting for you.
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
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 7729 Jailene Dr

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Appliances & Utilities
DishwasherDryer

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stone, Stucco
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: Townhouse

Community

Units in Building: 1

Lot Information

Lot Area: 3388 sqft

Price History for 7729 Jailene Dr

DatePriceEventSource
03/13/2018$238,000Sold
N/A
01/25/2018$236,000Listed For SaleAgent Provided
01/11/2008$229,700Sold
N/A

Market trends in Windermere

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$672K
$26.67KMoM
Sale-to-List Price
97.5%
0.3%MoM
Price per sq ft
$262
$6MoM
Available listings
291
2MoM
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Property Tax and Assessment

Year2024
Tax$5,608
Assessment$350,937
Home facts updated by county records

Comparable Sales for 7729 Jailene Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7719 Anselmo Ln, Windermere, FL
0.06
Townhouse
$375,000
06/22/26
3
2.5
1,644
7715 Anselmo Ln, Windermere, FL
0.06
Townhouse
$385,000
09/15/25
3
2.5
1,644
7752 Moser Ave, Windermere, FL
0.19
Townhouse
$388,000
11/05/25
3
2.5
1,644
7777 Moser Ave, Windermere, FL
0.22
Townhouse
$385,000
03/19/26
3
2.5
1,670
7711 Fairgrove Ave, Windermere, FL
0.17
Townhouse
$384,900
04/09/26
3
2.5
1,680
7768 Moser Ave, Windermere, FL
0.19
Townhouse
$365,000
03/14/26
3
2.5
1,644
7712 Moser Ave, Windermere, FL
0.19
Townhouse
$393,000
03/12/26
3
2.5
1,680
12838 Strode Ln, Windermere, FL
0.25
Townhouse
$405,000
12/22/25
3
2.5
1,748
12963 Garridan Ave, Windermere, FL
0.38
Townhouse
$378,250
07/08/25
3
2.5
1,535
12975 Calderdale Ave, Windermere, FL
0.46
Townhouse
$392,000
10/24/25
3
2.5
1,645

Nearby homes

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Assigned Schools

These are the assigned schools for 7729 Jailene 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
    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
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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
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  • 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
    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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Apartments for Rent

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Explore by feature - Pet Friendly

53 pet-friendly rentals in Windermere, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

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Explore by feature - Pool

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Explore by feature - Outdoor Space

18 rentals with an outdoor space in Windermere, FL

Homes for sale near 7729 Jailene Dr

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Off Market Homes Near 7729 Jailene Dr

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7729 Jailene Dr, Windermere, FL 34786 is a 3 bedroom, 3 bathroom, 1,644 sqft townhouse built in 2007. This property is not currently available for sale. 7729 Jailene Dr was last sold on Mar 13, 2018 for $238,000. The current Trulia Estimate for 7729 Jailene Dr is $392,400.