7741 Jailene Dr, Windermere, FL 34786
Property image
Property image
OFF MARKET

7741 Jailene Dr
Windermere, FL 34786

  • 3 Beds
  • 3 Baths
  • 1,724 sqft

$384,300

Trulia Estimate
as of Aug 22, 2026

$384,300

Trulia Estimate
as of Aug 22, 2026
  • 3 Beds
  • 3 Baths
  • 1,724 sqft

Home Highlights

Property Type
Townhouse
Living Area
1,724 sqft
Price/Sqft
$223
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 7741 Jailene Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Spacious 3-Bedroom, 2.5-Bath Townhome for Rent in Windermere Private Patio, and 2-Car Garage - located in a quiet and welcoming neighborhood close to top-rated schools, shopping, dining, major highways, and Orlando's world-famous attractions.

Step into comfort and convenience at a 3-bedroom, 2.5-bath townhome with 1,724 sq ft of living space nestled in one of Windermere's most desirable communities. This well-kept two-story home features neutral tones, tile flooring on the first floor, carpet upstairs, and a private fenced patio perfect for enjoying Florida's sunshine.

The main level includes a defined living area, a modern kitchen with granite countertops, stainless steel appliances, breakfast bar seating, a dining area with natural light, and a convenient laundry room and half bath.

Upstairs, you'll find a spacious primary suite with a ceiling fan, large walk-in closet, and a private bathroom with a double vanity, walk-in shower, and separate toilet room. Two additional bedrooms share a full bath with a tub/shower combo and generous vanity space ideal for families, guests, or a home office.

Community Amenities:
 Swimming Pool
 Tennis Court
 Basketball Court
 Sidewalks & Open Green Spaces

NO SHORT TERM RENTALS
7741 Jailene Dr, Windermere, FL 34786 is a 3 bedroom, 3 bathroom, 1,724 sqft townhouse. It last sold for $249,000 on Nov 21, 2019 (9,860% above the $2,500 asking price). More recently, it was listed as a rental in May 2026 with an asking price of $2,600 per month. That rental listing was removed on June 17, 2026. It is currently off market. The Trulia Estimate is $384,300, with a rent estimate of $2,638/month.

Home Details for 7741 Jailene Dr

Property Information

Property Type / Style
Property Type: Townhouse

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DryerWasher
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 7741 Jailene Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
7719 ANSELMO LANE, Windermere, FL
0.07
Townhouse
$375,000
06/22/26
3
2.5
1,644 sqft
7715 ANSELMO LANE, Windermere, FL
0.07
Townhouse
$385,000
09/15/25
3
2.5
1,644 sqft
7711 FAIRGROVE AVENUE, Windermere, FL
0.17
Townhouse
$384,900
04/09/26
3
2.5
1,680 sqft
7768 MOSER AVENUE, Windermere, FL
0.19
Townhouse
$365,000
03/14/26
3
2.5
1,644 sqft
7752 MOSER AVENUE, Windermere, FL
0.19
Townhouse
$388,000
11/05/25
3
2.5
1,644 sqft
7712 MOSER AVENUE, Windermere, FL
0.19
Townhouse
$393,000
03/12/26
3
2.5
1,680 sqft
7777 MOSER AVENUE, Windermere, FL
0.22
Townhouse
$385,000
03/19/26
3
2.5
1,670 sqft
12838 STRODE LANE, Windermere, FL
0.26
Townhouse
$405,000
12/22/25
3
2.5
1,748 sqft
7628 BILLINGHAM STREET, Windermere, FL
0.43
Townhouse
$402,000
12/30/25
3
2.5
1,480 sqft
12975 CALDERDALE AVENUE, Windermere, FL
0.47
Townhouse
$392,000
10/24/25
3
2.5
1,645 sqft

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

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

Price and Tax history

DateEventPrice
Jun 17, 2026
Source: Zillow Rentals
ListingRemoved
$2,500
Jun 10, 2026
Source: Zillow Rentals
PriceChange
$2,500
Price decreased by 2%
Jun 2, 2026
Source: Zillow Rentals
PriceChange
$2,545
Price decreased by 2%
May 26, 2026
Source: Zillow Rentals
Listed For Rent
$2,600
Jun 12, 2025
Source: Zillow Rentals
ListingRemoved
$2,500

Frequently asked questions about 7741 Jailene Dr

  • What is 7741 Jailene Dr estimated to be worth?
    Trulia's estimated value for 7741 Jailene Dr in Windermere, FL is $384,300.
  • What is the price history for 7741 Jailene Dr?
    7741 Jailene Dr in Windermere, FL last sold for $249,000 in November 2019.
  • 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 7741 Jailene Dr have air conditioning?
    Yes, 7741 Jailene Dr in Windermere, FL has air conditioning.
  • Does 7741 Jailene Dr have laundry facilities?
    Yes, 7741 Jailene Dr in Windermere, FL has in-unit laundry.

Homes for rent near 7741 Jailene Dr

Skip to last item
Skip to first item

Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
Skip to last item
  • Results are loading
Skip to first item