Welcome to 1255 Wispy Cypress Drive, a beautifully maintained 4 bedroom, 2.5 bathroom townhome with a 2-car garage located in the desirable Cypress Hammock community of Kissimmee. Built by Hanover Family Builders, this Allendale floor plan offers 1,918 square feet of living space with an open first-floor layout, spacious great room, dining area, covered rear lanai, and all bedrooms conveniently located upstairs. The kitchen features warm-tone finishes, quartz countertops, stainless steel appliances, a large island, and additional floor-to-ceiling cabinetry added in 2025 for extra storage and functionality. The home also includes thoughtful upgrades such as Hunter ceiling fans with LED lighting and remote controls in each bedroom and the living area, Ring security cameras at the entrance and patio, a remote-controlled garage door opener with digital keypad, Samsung refrigerator, Samsung washer and dryer, and blinds throughout the home. Cypress Hammock offers resort-style amenities including a community pool, playground, recreation areas, and wetland preserve views, while the location provides easy access to shopping, dining, major commuter routes, and Central Florida attractions including Disney Springs, Animal Kingdom, Hollywood Studios, EPCOT, and Magic Kingdom. With a spacious layout, modern finishes, added storage, community amenities, and a prime Kissimmee location, this townhome is move-in ready and offers the convenience of low-maintenance Florida living.
Property Details
Price:
$375,000
MLS #:
V4948931
Status:
Active
Beds:
4
Baths:
2.5
Type:
Townhouse
Subdivision:
CYPRESS HAMMOCK PH 1
Neighborhood:
34746kissimmeewestoftown
Listed Date:
Jun 3, 2026
Finished Sq Ft:
1,918
Total Sq Ft:
2,427
Lot Size:
3,485 sqft / 0.08 acres (approx)
Year Built:
2022
See this Listing
Schools
Interior
Appliances
Dishwasher, Dryer, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Central, Electric
Interior Features
Ceiling Fan(s), Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, PrimaryBedroom Upstairs, Walk-In Closet(s)
Laundry Features
Inside
Levels
Two
Exterior
Association Amenities
Playground, Recreation Facilities
Attached Garage YN
1
Common Walls
Corner Unit
Community Features
Dock, Community Mailbox, Irrigation-Reclaimed Water, Park, Playground, Sidewalks
Construction Materials
Block, Stucco, Wood Frame
Covered Spaces
2
Direction Faces
Northwest
Exterior Features
Irrigation System, Sidewalk, Sliding Doors
Garage Spaces
2
Lot Features
Corner Lot, Sidewalk
Patio And Porch Features
Rear Porch
Roof
Shingle
Window Features
Double Pane Windows, Shades
Financial
HOA Fee
$355
HOA Fee Frequency
Monthly
HOA Includes
Community Pool, Maintenance Structure, Maintenance Grounds, Recreational Facilities
HOA Name
Sentry Management
HOA Phone
407-846-6323
Tax Year
2025
Taxes
$4,397
Map
Community
- Address1255 WISPY CYPRESS DRIVE KISSIMMEE FL
- SubdivisionCYPRESS HAMMOCK PH 1
- CityKISSIMMEE
- CountyOsceola
- Zip Code34746
Subdivisions in KISSIMMEE
- Association of Poinciana Villages
- BELLALAGO
- BELLAVIDA PH 01
- COMPASS BAY
- EAGLE LAKE PH 1
- EAST PALM RESORT CONDO
- MargaritaVille
- POINCIANA NBRHD 5 NORTH VILL 3
- POINCIANA SUBDIVISION NBRHD 5 NORTH VIL 3
- POINCIANA VLG 2 NBHD 1
- ROLLING OAKS PH 7
- Siesta Lago
- SONOMA RESORT AT TAPESTRY PH 1
- STOREY CREEK PH6
- STOREY LAKE TR K
- SUMMERVILLE RESORT
- VENTURA AT WINDSOR HILLS CONDO PH 1
Market Summary
Property Summary
- Located in the CYPRESS HAMMOCK PH 1 subdivision, 1255 WISPY CYPRESS DRIVE KISSIMMEE FL is a Townhouse for sale in KISSIMMEE, FL, 34746. It is listed for $375,000 and features 4 beds, 3 baths, and has approximately 1,918 square feet of living space, and was originally constructed in 2022. The current price per square foot is $196. The average price per square foot for Townhouse listings in KISSIMMEE is $210. The average listing price for Townhouse in KISSIMMEE is $349,924. To schedule a showing of MLS#v4948931 at 1255 WISPY CYPRESS DRIVE in KISSIMMEE, FL, contact your InvestPro Properties, Inc. agent at 561-203-7022.
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Courtesy of KELLER WILLIAMS HERITAGE REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than InvestPro Properties, Inc. include the name of the listing broker. Neither the listing company nor InvestPro Properties, Inc. shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 1255 WISPY CYPRESS DRIVE
KISSIMMEE, FL
