14755 Peekskill Dr
Winter Garden, FL 34787
- 3 Beds
- 3 Baths
- 1,634 sqft
3 Beds
3 Baths
1,634 sqft
Local Information
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Description
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!
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
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 14755 Peekskill Dr
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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 |
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Exterior Home Features Roof: CompositionDeckExterior: StuccoPatioPorch |
Parking & Garage GarageParking: Garage Detached |
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Year Built Year Built: 2007Year Updated: 2007 |
Property Type / Style Property Type: TownhouseArchitecture: Craftsman |
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Units in Building: 1 |
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Lot Area: 3484 sqft |
Price History for 14755 Peekskill Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 03/09/2017 | $225,000 | Sold | N/A |
| 01/26/2017 | $225,000 | Pending | Agent Provided |
| 01/03/2017 | $225,000 | Listed For Sale | Agent Provided |
| 03/31/2014 | $184,000 | Sold | N/A |
| 02/08/2014 | $179,000 | Listed For Sale | Agent Provided |
| 06/17/2010 | $125,000 | Sold | Stellar MLS #O4954210 |
| 03/26/2007 | $227,700 | Sold | N/A |
Market trends in Winter Garden
Last updated May 2026
Avg. sale price
$592K
$1.67KMoM
Sale-to-List Price
98.3%
0.3%MoM
Price per sq ft
$248
$3MoM
Available listings
744
17MoM
Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $3,243 |
| Assessment | $331,212 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$2,527/mo
Homes for rent near 14755 Peekskill Dr
See what comparable homes in the neighborhood are renting for.Comparable Sales for 14755 Peekskill Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Townhouse | $419,497 | 02/26/26 | 3 | 2.5 | 1,624 | |
0.05 | Townhouse | $344,000 | 04/27/26 | 3 | 3 | 1,831 | |
0.31 | Townhouse | $407,000 | 09/15/25 | 3 | 2.5 | 1,639 | |
0.05 | Townhouse | $464,000 | 02/25/26 | 4 | 3 | 2,159 | |
0.30 | Townhouse | $349,900 | 10/30/25 | 3 | 2.5 | 1,496 | |
0.55 | Townhouse | $197,500 | 04/16/26 | 3 | 2.5 | 1,476 | |
0.44 | Townhouse | $365,000 | 09/22/25 | 3 | 2.5 | 1,464 | |
0.51 | Townhouse | $415,000 | 04/10/26 | 3 | 2.5 | 1,512 | |
0.38 | Townhouse | $380,000 | 11/25/25 | 3 | 2.5 | 1,476 | |
0.27 | Townhouse | $495,000 | 05/26/26 | 4 | 3 | 2,328 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 14755 Peekskill Dr.
What Locals Say about Winter Garden
At least 510 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
42 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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Homes for sale near 14755 Peekskill Dr
Off Market Homes Near 14755 Peekskill Dr
14755 Peekskill Dr, Winter Garden, FL 34787 is a 3 bedroom, 3 bathroom, 1,634 sqft townhouse built in 2007. This property is not currently available for sale. 14755 Peekskill Dr was last sold on Mar 9, 2017 for $225,000. The current Trulia Estimate for 14755 Peekskill Dr is $378,800.

