14760 Peekskill Dr, Winter Garden, FL 34787
Property image
Property image
OFF MARKET

$321,300

Trulia Estimate
as of Aug 30, 2026
  • 2 Beds
  • 2.5 Baths
  • 1,406 sqft
  • 2 Beds
  • 2.5 Baths
  • 1,406 sqft

14760 Peekskill Dr, Winter Garden, FL 34787

Home Highlights

Property Type
Townhouse
Living Area
1,406 sqft
Price/Sqft
$229

Local Information

  • Map ViewExplore the area around 14760 Peekskill Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Modern & Fully Renovated Townhome in Desirable Independence Community, Winter Garden/Windermere

Experience resort-style living in this rare, fully updated 2-bedroom, 2.5-bath townhome! This spacious property features two large master suites, a dining room, a living room, and a fenced backyard with a front porch perfect for relaxing in a quiet neighborhood. Located in the sought-after Independence community, just minutes from Disney and close to new shopping centers, restaurants, and top-rated schools.

Available November 1st This home has been fully renovated with brand-new appliances, updated bathrooms, a modern kitchen, fresh paint, and new flooring throughout.

Community Features:

 Two resort-style swimming pools
 Tennis and basketball courts
 Two fully-equipped fitness centers
 Two clubhouses with arcade and billiards
 Walking and biking trails
 Community boat ramp
 Multiple playgrounds and green spaces
 Dog parks
 Top-rated schools (Bridgewater Middle School located within the community)

Bonus: High-speed internet and cable are INCLUDED in the monthly rent!

Don't miss this opportunity to enjoy luxurious living in an upscale community where small pets are welcome! The property is within walking distance of the community park, which includes a playground, fitness stations, and dog parks.

Live the life you've always wanted, with incredible amenities and a fantastic location!

Listed in the lease.
14760 Peekskill Dr, Winter Garden, FL 34787 is a 2 bedroom, 3 bathroom, 1,406 sqft townhouse. It last sold for $150,900 on Jun 27, 2014 (5,936% above the $2,500 asking price). More recently, it was listed as a rental in October 2024 with an asking price of $2,750 per month. That rental listing was removed on November 14, 2024. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $321,300, with a rent estimate of $2,266/month.

Home Details for 14760 Peekskill Dr

Interior Features

Heating & Cooling
Heating: Heat PumpAir ConditioningCooling System: Central AirHeating Fuel: Heat Pump
Appliances & Utilities
DishwasherDryerWasher
Levels, Entrance, & Accessibility
Floors: Hardwood

Property Information

Property Type / Style
Property Type: Townhouse

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Exterior Features

Pool
Pool
Parking & Garage
Parking: Detached Off Street, On Site

Building

Community rooms
Fitness Center

Additional Information

Pool

Comparable Sales for 14760 Peekskill Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14778 PEEKSKILL DRIVE, Winter Garden, FL
0.02
Townhouse
$410,000
08/19/26
3
3
1,831 sqft
14814 PEEKSKILL DRIVE, Winter Garden, FL
0.06
Townhouse
$419,497
02/26/26
3
2.5
1,624 sqft
14447 PRUNNINGWOOD PLACE, Winter Garden, FL
0.38
Townhouse
$330,000
06/05/26
2
2.5
1,250 sqft
14531 PLEACH STREET, Winter Garden, FL
0.30
Townhouse
$349,900
10/30/25
3
2.5
1,496 sqft
14488 WHITTRIDGE DRIVE, Winter Garden, FL
0.08
Townhouse
$464,000
02/25/26
4
3
2,159 sqft
14421 VASHONS WAY, Winter Garden, FL
0.45
Townhouse
$325,000
03/31/26
2
2.5
1,088 sqft
14267 AVENUE OF THE GROVES, Winter Garden, FL
0.50
Townhouse
$332,500
05/15/26
2
2.5
1,289 sqft
14287 AVENUE OF THE GROVES, Winter Garden, FL
0.49
Townhouse
$315,000
03/17/26
2
2.5
1,152 sqft
14433 PLEACH ST, Winter Garden, FL
0.32
Townhouse
$407,000
09/15/25
3
2.5
1,639 sqft
14467 PRUNNINGWOOD PLACE, Winter Garden, FL
0.39
Townhouse
$380,000
11/25/25
3
2.5
1,476 sqft

Nearby homes

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Around this home

What Locals Say about Winter Garden

At least 513 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 86 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 76 % Say it's quiet

  • 75 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 72 % Say yards are well-kept

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 54 % Say there's wildlife

  • 50 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • jhp331
    "A rated schools and lots to do for families "
    0
    Flag
  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
    Flag
  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
    Flag
  • Ypgs9v7hpd
    "It is a nice area and the schools are nice. It is good area to raise children away from the tourists area and the city ."
    0
    Flag
  • Ypgs9v7hpd
    "The only thing that is unique about this neighborhood is the people that are friendly and the kids get along great. The only downside of living here in Wintergarden is it’s not enough places to go out to eat and it is not enough places for kids to hang out or teenagers to hang out and the closest place for teenagers to hang out is at the Wintergarden Grove area where you have to take off the exit 9, which I think that’s a bit too far for them to hang out when they can remain closer, it would be better if they had a place to hang out within the neighborhood. Also, Price is over here for a living is very high so if you’re not making a decent amount of money, it is expensive even the apartments that are surrounding it. It’s expensive.."
    0
    Flag
  • Emilye Chasen
    "Downtown events occur all the time. Christmas, Halloween, 4th of July etc. Santa comes down my street"
    1
    Flag
  • Ypgs9v7hpd
    "I’ve living here for the last 3 yrs. It’s nice area, people are nice. It’s nice area to raise your family there."
    0
    Flag
  • Heather Kotyk
    "I work near the airport and the commute using the turnpike and I4 is about 25-30 minutes. Traffic is usually manageable and continuously is moving "
    0
    Flag
  • Erin
    "There are many families in the neighborhood, a great playground and an A rated school nearby. There’s also a grocery store and pharmacy conveniently within a mile. "
    0
    Flag
  • Maria Rojas
    "Great place to have a family, lots of parks and activities for kids. Amazing schools and the community is very united. Most communities have hoa "
    0
    Flag
  • Rosa Aguilar
    "There’s lots of places, activities, parks, trails to take kids. There’s also lots of churches with daycare and city programs for children to take part in."
    0
    Flag
  • Andres.toro
    "Mostly all good schools. A lot of parks (and a few others upcoming) and services are increasing in availability. "
    0
    Flag
  • Logan Mahalek
    "The historic area of downtown winter garden boasts local shops and restaurants and also hosts a farmers market every weekend. There is also plenty of name brands within 15 minutes "
    0
    Flag
  • Cfbranf3rd
    "I’m don’t have a commute, as I’m retired. I’m in Cypress Reserve, and Avalon Road can be a nightmare at school drop off/pick up times."
    0
    Flag
  • Kelly
    "Beautiful, safe & friendly area. Winter Garden is a great place to raise a family! This is a very active area with tons of activities. Lots of wildlife & opportunities to get in touch with nature. Big, beautiful Florida birds and animals all around. Great restaurants too! "
    0
    Flag
  • Geisha
    "In Winter Garden for the area's of Horizon West, Hamlin, Summerlake, Waterleight, The Grove is amazing is like living in a perfect community bubble completely recomend"
    0
    Flag
  • Catherine Law
    "There is a private lake side park and a bbq area. Dogs poop trash and bags available. Dogs need to be on leash all the time. No many houses are fenced. "
    0
    Flag
  • Vanessaasantini
    "Wonderful , Safe, beatiful, peaceful, very good, clean, good school, nice and bog city Close to supermarket, gas station "
    2
    Flag
  • Aj2636
    "Halloween costume parties for kids. Community Easter egg hunts. Santa Claus visits on a fire truck. Community watch parties for football games. A soccer field, tennis courts, pickleball courts and basketball courts that allow the neighborhood to enjoy each other’s company. During COVID, we had live music performances in the park."
    0
    Flag
  • Cara Conley
    "The area is established and offers. Great amenities within 15 minutes. Clean and safe and welcoming."
    1
    Flag
  • Isaac Peterson
    "Very friendly and helpful neighbors, and the schools are awesome. Very safe "
    2
    Flag
  • Aj2636
    "I’ve lived here for 11 years. It’s close to shopping. The neighborhood feels comfortable with homes far apart from each other. Nice lakes nearby that most neighborhoods have access to. Hospital close-by for emergencies."
    1
    Flag
  • Felton.amanda
    "I lived here for 10 years and just now moving this month. The neighborhood is safe not a lot of crime just a few thieves here and there that steal packages from ppls door steps occasionally."
    1
    Flag
  • Dismiki24
    "Lots of dogs in our neighborhood but many don’t pick up after their dogs. There is a dog park nearby "
    0
    Flag
  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
    Flag
  • Megan E.
    "You will love it! Lots of dog owners and very kind. Lots of doggy poop bag stations as we all know! Great dog parks and trails to go on lovely long walks. "
    13
    Flag
  • Zimmiac
    "Everything is very nice ,and the persons are very nice ,very quite area and the schools are good also,parks and events as well very nice"
    0
    Flag
  • Lil D.
    "The people and shops are great. Love all the bike tails as well. Every Saturday they have the farmers market and quite enjoyable to go to and walk around. "
    0
    Flag
  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
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  • Hollister M.
    "Lots of dogs. Most people are very polite about their dogs. People with cats do not keep them indoors and they roam the streets a lot. Most people pick up after their dogs and keep them on leashes."
    0
    Flag
  • Jim
    "It’s an amazing place to love. Doesn’t feel like living in Florida. I love living the country and still being close to Disney"
    6
    Flag
  • Cathy
    "Great it is safe and very homey the people are friendly and irs all clean. Very close to shopping places to eat and nice bars "
    5
    Flag
  • Jonathancrespo21
    "We have a neighborhood Facebook page open to everyone and we use this to communicate with each other regularly. We participate in food drives, raise money for special causes, and even sponsor dinners for our local police, firefighters, and nurses."
    0
    Flag
  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
    Flag
  • Valerie
    "Weekend Farmers Market. Beautiful downtown area. Older historic feeling. Very convenient with shops food and stores. Best city I've lived in since being here in Florida."
    0
    Flag
  • jay j
    "People love dogs. They are loving animals that make everyone happy when they see them. Most people now a days have dogs"
    0
    Flag
  • Nicola O.
    "Some neighbors don’t clean up after their pets or leave their pets on the balcony barking all night long, but there is a lot of open grass fields and dog stations all throughout. "
    0
    Flag
  • Candy H.
    "Winter Garden Farmer’s Market and shows going on at the Garden Theatre, along with more dog friendly mom and pop places."
    0
    Flag
  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
Nov 14, 2024
Source: Zillow Rentals
ListingRemoved
$2,500
Nov 14, 2024
Source: Zillow Rentals
PriceChange
$2,500
Price decreased by 2%
Oct 28, 2024
Source: Zillow Rentals
PriceChange
$2,550
Price decreased by 4%
Oct 15, 2024
Source: Zillow Rentals
PriceChange
$2,650
Price decreased by 4%
Oct 6, 2024
Source: Zillow Rentals
Listed For Rent
$2,750

Frequently asked questions about 14760 Peekskill Dr

  • What is 14760 Peekskill Dr estimated to be worth?
    Trulia's estimated value for 14760 Peekskill Dr in Winter Garden, FL is $321,300.
  • What is the price history for 14760 Peekskill Dr?
    14760 Peekskill Dr in Winter Garden, FL last sold for $150,900 in June 2014.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $583K. That is down $3.33K from the prior month.
  • Does 14760 Peekskill Dr have air conditioning?
    Yes, 14760 Peekskill Dr in Winter Garden, FL has air conditioning.
  • Does 14760 Peekskill Dr have a pool?
    Yes, 14760 Peekskill Dr in Winter Garden, FL has a pool.

Homes for rent near 14760 Peekskill Dr

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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.
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