14755 Peekskill Dr, Winter Garden, FL 34787
Property image
Property image
OFF MARKET

$378,400

Trulia Estimate
  • 3 Beds
  • 3 Baths
  • 1,634 sqft

14755 Peekskill Dr, Winter Garden, FL 34787

Est. Refi. Payment $2,702/mo*
Refinance Your Home
Currently Off Market - Sold Mar 9, 2017 for $225,000

Home Value

Trulia Estimate
$378K
Since last month
Decreased$400 (-0.1%)
Since last year
Decreased$3K (-0.9%)
Since last sale
Increased$152K (+67.7%)
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 +80% in the last 10 years
MonthEstimated value
2026
August 2026$377K
August 2026$377K
July 2026$378K
June 2026$376K
May 2026$379K
April 2026$379K
March 2026$378K
February 2026$374K
January 2026$372K
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
14814 PEEKSKILL DRIVE, Winter Garden, FL
0.08
Townhouse
$419,497
02/26/26
3
2.5
1,624
14778 PEEKSKILL DRIVE, Winter Garden, FL
0.05
Townhouse
$410,000
08/19/26
3
3
1,831
14433 PLEACH ST, Winter Garden, FL
0.31
Townhouse
$407,000
09/15/25
3
2.5
1,639
14488 WHITTRIDGE DRIVE, Winter Garden, FL
0.05
Townhouse
$464,000
02/25/26
4
3
2,159
14531 PLEACH STREET, Winter Garden, FL
0.30
Townhouse
$349,900
10/30/25
3
2.5
1,496
6530 PASTURELANDS PLACE, Winter Garden, FL
0.27
Townhouse
$470,000
07/22/26
3
2.5
2,067
14141 Avenue Of The Grvs, Winter Garden, FL
0.55
Townhouse
$197,500
04/16/26
3
2.5
1,476
14433 VASHONS WAY, Winter Garden, FL
0.44
Townhouse
$365,000
09/22/25
3
2.5
1,464
6923 PASTURELANDS PLACE, Winter Garden, FL
0.51
Townhouse
$415,000
04/10/26
3
2.5
1,512
14467 PRUNNINGWOOD PLACE, Winter Garden, FL
0.38
Townhouse
$380,000
11/25/25
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
$680,000
3
2
2,224
Off Market
14488 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.05
$464,000
4
3
2,159
Recently Sold
14494 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.06
$441,000
3
2.5
2,067
Off Market
14797 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.05
$384,900
3
2.5
1,644
Off Market
14495 WHITTRIDGE DRIVE, Winter Garden, FL 34787
0.08
$534,900
3
2
2,026
Off Market
14778 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.05
$410,000
3
3
1,831
Recently Sold
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
0.08
$590,700
6
4.5
3,142
Off Market
14790 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.06
$382,800
3
2.5
1,625
Off Market
6478 OLD CARRIAGE ROAD, Winter Garden, FL 34787
0.09
$525,600
3
2.5
2,184
Off Market
14833 PEEKSKILL DRIVE, Winter Garden, FL 34787
0.08
$431,300
3
2.5
1,816
Off Market

Local Information

  • Map ViewExplore the area around 14755 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
1,634 sqft
Price/Sqft
$232
Parking
Garage

About this House

From its spacious, open floor plan to its private courtyard paradise, this townhouse is filled with features youll love! Located in the hot Independence neighborhood of Winter Garden just a short walk from the main clubhouse and Independence Elementary School. Beautifully maintained landscaping throughout the community--especially on Peekskill Drive--gives this unit tremendous curb appeal. Theres plenty of street parking for guests, plus a detached 2-car garage with alley access. A covered front porch enters onto the impressively designed 1st floor, with an open dining area, living room, kitchen, and breakfast nook. Upgrades include Silestone quartz counters and cabinet crown molding in the kitchen, built-in surround sound, ceramic tile throughout, and updated lighting fixtures. Theres also a powder room and large pantry/under-stair storage closet. Youll be drawn to the fantastic back courtyard with a raised pergola, outdoor speakers, and custom irrigation system for plants and herbs. Its a relaxing oasis and a perfect place to entertain. Upstairs, the master bedroom boasts a huge bath with dual sinks, garden tub, and separate shower, and a large walk-in closet. Two other bedrooms and the additional full bath are split to the other side of 2nd floor. The laundry is also located upstairs for convenience. Lovingly maintained and close to Disney, Windermere, and Winter Garden Village, this townhouse is sure to impress. Schedule your showing today before someone else makes it their home sweet home!
14755 Peekskill Dr, Winter Garden, FL 34787 is a 3 bedroom, 3 bathroom, 1,634 sqft townhouse built in 2007. It last sold for $225,000 on Mar 9, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $378,400, with a rent estimate of $2,399/month.

Home Details for 14755 Peekskill Dr

Interior Features

Heating & Cooling
Heating: Heat Pump, ElectricAir ConditioningCooling System: CentralHeating Fuel: Heat Pump
Levels, Entrance, & Accessibility
Stories: 2Floors: Tile, Carpet
Interior Details
Types of Rooms: Walk In Closet, Dining RoomCeiling Fan
Appliances & Utilities
DishwasherMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: CompositionDeckExterior: StuccoPatioPorch
Parking & Garage
GarageParking: Garage Detached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: TownhouseArchitecture: Craftsman

Community

Units in Building: 1

Lot Information

Lot Area: 3484 sqft

Price and Tax history

DateEventPrice
Mar 9, 2017
Source: N/A
Sold
$225,000
Jan 26, 2017
Source: Agent Provided
Pending
$225,000
Jan 3, 2017
Source: Agent Provided
Listed For Sale
$225,000
Mar 31, 2014
Source: N/A
Sold
$184,000
Feb 8, 2014
Source: Agent Provided
Listed For Sale
$179,000

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

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
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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
    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 ."
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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
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  • 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
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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
    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
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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
    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
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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

LGBTQ Local Legal Protections

Frequently asked questions about 14755 Peekskill Dr

  • What is 14755 Peekskill Dr estimated to be worth?
    Trulia's estimated value for 14755 Peekskill Dr in Winter Garden, FL is $378,400.
  • What is the price history for 14755 Peekskill Dr?
    14755 Peekskill Dr in Winter Garden, FL last sold for $225,000 in March 2017.
  • 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 14755 Peekskill Dr have air conditioning?
    Yes, 14755 Peekskill Dr in Winter Garden, FL has air conditioning.
  • Does 14755 Peekskill Dr have a garage?
    Yes, 14755 Peekskill Dr in Winter Garden, FL has a garage.

Explore by feature - Pet Friendly

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Off Market Homes Near 14755 Peekskill Dr

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