5966 CYPRESS HILL ROAD, WINTER GARDEN, FL 34787
SIGNATURE LAKES PH 3B-4, 3B-5 & 3B-7 83/27 LOT 184 · Orange County
Key Facts
Description
Price Improvement – Welcome to 5966 Cypress Hill Rd, located in the highly sought-after Independence community of Winter Garden. This well-maintained home offers a rare blend of privacy, space, and lifestyle amenities. Situated on a larger-than-average lot with no rear neighbors, the home backs up to an open area, creating a peaceful and private setting—perfect for relaxing or entertaining. Features include a covered side lanai, extended driveway, and detached garage, offering both functionality and additional space. Enjoy resort-style living in Independence, including: • Two private boat ramps with access to Lake Speer and Lake Hancock • Two clubhouses, pools, fitness centers, and sports courts • Internet included through Spectrum as part of the HOA • Walking trails, parks, and frequent community events • Internet included through Spectrum as part of the HOA The home is zoned for top-rated schools and conveniently located near shopping, dining, and major highways. Solar System: Property includes a solar system with an existing loan. Buyer to assume solar loan. Note: Water softener not included but may be purchased separately. Solar loan assumption required; details available upon request.
Property Information
Property Type
Residential
Sub-Type
Single Family Residence
Year Built
2017
Stories
2
Living Area
2,839 sq ft
Lot Size
0.22 acres
Garage Spaces
2
Ownership
Fee Simple
Zoning
P-D
Days on Market
145
MLS® Listing#
O6376219
Property Features
Exterior
Appliances
Cooling
Heating
Flooring
Laundry
Construction
Foundation
Roof
Community
Utilities
Sewer
Water Source
Rooms
- 13x9First
- 13x9First
- Bathroom 215x12Second
- Bathroom 312x12Second
- Bedroom 412x12Second
- Dining Room11x12First
- Family Room19x17First
- KitchenFirst
- Living Room20x8First
- Loft12x12Second
- Master BathroomFirst
- Master Bedroom14x15First
Schools
- Elementary:
- Independence Elementary
- Middle:
- Bridgewater Middle
- High:
- Windermere High School
Financial Details
HOA
$195 / Monthly
Tyler Parsons
Annual Taxes
$9,648
Tax year 2025
Parcel Number
16-23-27-8135-01-843
Directions
From FL-429, take the Seidel Rd exit and head west. Turn right onto Independence Pkwy, then turn left onto Cypress Hill Rd. Property will be on your right at 5966 Cypress Hill Rd, Winter Garden, FL 34786.
Affordability Calculator
$139,000
Estimated monthly payment
$3,699/mo
Principal $556,000 · Est. interest $775,669 over 30 yrs
Neighborhood Market Statistics
How this home compares to active listings in WINTER GARDEN, FL
- $395,280
- Median Listing Price
- 70
- Median Days on Market
- 1,846
- Median Sq Ft
- $225
- Median Price / Sq Ft
- 2,006
- Active Listings
- This home’s price is 76% above the area median.
- Its price per sq ft is 9% above the area median.
Market statistics compiled from active EXIT Realty® and MLS listings in WINTER GARDEN, FL.
Location
- 5966 CYPRESS HILL ROAD, WINTER GARDEN, FL 34787
Points of Interest in WINTER GARDEN, FL
Showing the WINTER GARDEN area map.
Nearby Schools
Bridgewater Middle School
Secondary · 0.4 mi away
Champions at Bridgewater Middle School
Elementary · 0.4 mi away
Keenes Crossing Elementary
Elementary · 0.7 mi away
Champions at Independence Elementary School
Elementary · 1.2 mi away
Independence Elementary School
Elementary · 1.2 mi away
Foundation Academy
School · 1.5 mi away
The New Academy
School · 1.7 mi away
Cranium Academy
School · 1.7 mi away
Windermere High School
Secondary · 1.7 mi away
Whispering Oak Elementary School
Elementary · 2.0 mi away
Champions at Summerlake Elementary School
Elementary · 2.3 mi away
Summerlake Elementary Pto
Elementary · 2.3 mi away
Windermere Preparatory School
Elementary · 2.5 mi away
Hamlin Middle School
Secondary · 2.6 mi away
Hamlin Elementary School - Ocps
Elementary · 2.7 mi away
Primrose Schools
Elementary · 3.3 mi away
Horizon West Middle School - Ocps
Secondary · 3.4 mi away
Primrose School of Horizon West
School · 3.4 mi away
Sunset Park Elementary
Elementary · 3.5 mi away
Sunridge Elementary
Elementary · 3.6 mi away
Commute Calculator
Nearby Homes
Similar Homes Nearby
Similar Home Values
Comparable nearby listings and their asking prices.
| Address | Price | Beds | Baths | Sq Ft |
|---|---|---|---|---|
| 1304 ORTEGA STREET, WINTER SPRINGS, FL | $488,000 | 4 | 3 | 2,152 |
| 5413 NEW INDEPENDENCE PARKWAY, WINTER GARDEN, FL | $488,000 | 4 | 3 | 2,131 |
| 131 LISA LOOP, WINTER SPRINGS, FL | $489,000 | 4 | 3 | 2,309 |
| 1491 AXEL CIRCLE, WINTER HAVEN, FL | $489,000 | 5 | 3 | 3,022 |
| 986 TURKEY HOLLOW CIRCLE, WINTER SPRINGS, FL | $489,000 | 4 | 2 | 1,864 |
| 986 Turkey Hollow Circle, Winter Springs, FL | $489,000 | 4 | 2 | 1,864 |
Moving Cost Estimate
EXIT Agents in WINTER GARDEN
Listing Courtesy: DALTON WADE INC - 888-668-8283
Last Updated: 2026-01-21