14743 Peekskill Dr, Winter Garden, FL 34787
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Property image
OFF MARKET

14743 Peekskill Dr
Winter Garden, FL 34787

  • 3 Beds
  • 3 Baths
  • 1,816 sqft

$396,300

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $2,790/mo*
Refinance Your Home

$396,300

Trulia Estimate
as of Aug 17, 2026
Est. Refi. Payment $2,790/mo*
Refinance Your Home
3 Beds
3 Baths
1,816 sqft

Home Value

Trulia Estimate
$396K
Since last month
Increased$400 (+0.1%)
Since last year
Decreased$8K (-2%)
Since last sale
Increased$136K (+52.1%)
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 +69% in the last 10 years
MonthEstimated value
2026
August 2026$397K
July 2026$398K
June 2026$397K
May 2026$397K
April 2026$398K
March 2026$397K
February 2026$393K
January 2026$389K
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
14778 PEEKSKILL DRIVE, Winter Garden, FL
0.06
Townhouse
$344,000
04/27/26
3
3
1,831
14814 PEEKSKILL DRIVE, Winter Garden, FL
0.09
Townhouse
$419,497
02/26/26
3
2.5
1,624
14488 WHITTRIDGE DRIVE, Winter Garden, FL
0.06
Townhouse
$464,000
02/25/26
4
3
2,159
6530 PASTURELANDS PLACE, Winter Garden, FL
0.26
Townhouse
$470,000
07/22/26
3
2.5
2,067
14433 PLEACH ST, Winter Garden, FL
0.29
Townhouse
$407,000
09/15/25
3
2.5
1,639
14433 VASHONS WAY, Winter Garden, FL
0.42
Townhouse
$365,000
09/22/25
3
2.5
1,464
14531 PLEACH STREET, Winter Garden, FL
0.29
Townhouse
$349,900
10/30/25
3
2.5
1,496
14467 PRUNNINGWOOD PLACE, Winter Garden, FL
0.37
Townhouse
$380,000
11/25/25
3
2.5
1,476
6524 PASTURELANDS PLACE, Winter Garden, FL
0.26
Townhouse
$495,000
05/26/26
4
3
2,328
14141 Avenue Of The Grvs, Winter Garden, FL
0.54
Townhouse
$197,500
04/16/26
3
2.5
1,476

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
14446 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.03
$417,687
3
2
1,650
Recently Sold
14477 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.07
$674,200
3
2
2,224
Off Market
14488 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.06
$464,000
4
3
2,159
Recently Sold
14494 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.07
$443,900
3
2.5
2,067
Off Market
14797 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.06
$383,400
3
2.5
1,644
Off Market
14495 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.09
$532,100
3
2
2,026
Off Market
14742 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.05
$424,900
3
3
1,763
Off Market
6475 NEW INDEPENDENCE PARKWAY, Winter Garden, FL 34787
0.07
$595,200
6
4.5
3,142
Off Market
14790 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.07
$384,100
3
2.5
1,625
Off Market
6478 OLD CARRIAGE ROAD, Winter Garden, FL 34787
0.09
$522,600
3
2.5
2,184
Off Market
14833 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.10
$429,700
3
2.5
1,816
Off Market
14814 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.09
$419,497
3
2.5
1,624
Recently Sold

Local Information

  • Map ViewExplore the area around 14743 Peekskill Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Townhouse
Year Built
2007
Living Area
1,816 sqft
Price/Sqft
$218
Parking
Garage

About this House

Rare find in Independence. An end unit townhouse with 3 FULL Bathrooms and Master's bedroom on the GROUND floor! This spacious townhouse also has a den/office, a separate dining room and 2 other bedrooms. The kitchen has granite countertops, 42" cabinets and stainless steel appliances. The family room adjacent to the kitchen opens to a brick pavered courtyard. The master bathroom has a separate glass enclosed tile shower, his and her sinks, a whirlpool tub and a walk in closet. HOA includes basic cable and internet. Community amenities include access to 2 pools, play areas, fitness center, dog park, tennis and basketball courts, walking/bike path and boat ramps. Centrally located to schools, shopping, restaurants and hospital. Close to theme parks.
14743 Peekskill Dr, Winter Garden, FL 34787 is a 3 bedroom, 3 bathroom, 1,816 sqft townhouse built in 2007. It last sold for $261,000 on Oct 3, 2019. More recently, it was listed as a rental in March 2017 with an asking price of $1,795 per month. That rental listing was removed on April 17, 2017. It is currently off market. The Trulia Estimate is $396,300, with a rent estimate of $2,659/month.

Home Details for 14743 Peekskill Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Linoleum Vinyl
Interior Details
AtticTypes of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath, OfficeCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Jetted Bath Tub
Windows, Doors, Floors & Walls
Double Paned Windows

Exterior Features

Exterior Home Features
Roof: CompositionPatioPorch
Parking & Garage
GarageParking: Garage

Property Information

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

Community

Units in Building: 1

Lot Information

Lot Area: 4695 sqft

Building

Fitness & Sports
Basketball CourtTennis Court
Community rooms
Fitness Center

Price and Tax history

DateEventPrice
Oct 3, 2019
Source: N/A
Sold
$261,000
Aug 21, 2019
Source: Agent Provided
Listed For Sale
$270,000
Apr 17, 2017
Source: Agent Provided
ListingRemoved
$1,695
Mar 30, 2017
Source: Agent Provided
PriceChange
$1,695
Price decreased by 3%
Mar 21, 2017
Source: Agent Provided
PriceChange
$1,750
Price decreased by 3%

Market trends in Winter Garden

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$583K
$3.33KMoM
Sale-to-List Price
98.3%
0.2%MoM
Price per sq ft
$254
$3MoM
Available listings
760
4MoM
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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 "
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  • 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
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  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
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  • 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 ."
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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

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Apartments for Rent

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Explore by feature - Pet Friendly

157 pet-friendly rentals in Winter Garden, FL

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Homes for sale near 14743 Peekskill Dr

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Off Market Homes Near 14743 Peekskill Dr

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Frequently asked questions about 14743 Peekskill Dr

  • What is 14743 Peekskill Dr estimated to be worth?
    Trulia's estimated value for 14743 Peekskill Dr in Winter Garden, FL is $396,300.
  • What is the price history for 14743 Peekskill Dr?
    14743 Peekskill Dr in Winter Garden, FL last sold for $261,000 in October 2019.
  • 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 14743 Peekskill Dr have air conditioning?
    Yes, 14743 Peekskill Dr in Winter Garden, FL has air conditioning.
  • Does 14743 Peekskill Dr have laundry facilities?
    Yes, 14743 Peekskill Dr in Winter Garden, FL has in-unit laundry.