$695,000

5966 Cypress Hill Road

Winter Garden, FL 34787

Listing updated: April 26, 2026 at 10:44 AM ET

Active

Beds

Baths

2,839

Sq Ft

0.22

Acres

2017

Built

◆$245/sqft

Single Family Residence

Property type

2017

Year built

9,798 sqft

Lot size

$245

Price / sq ft

$195/mo

HOA dues

Days on market

Garage spaces

Flood zone

About this home

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.

Estimated monthly payment

Principal & interest$3,514

Property taxes$804

Home insurance (est.)$319

HOA dues$195

Down payment

20%

$139,000 downRate

6.5%

Term

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history93 days on market

Status: Active
Jan 23, 2026
Listed$719,000
Jan 23, 2026
Price reduced$695,000

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Facts & features

Property type: Residential
Sub type: Single Family Residence
Status: Active
Days on market: 93
Subdivision: Signature Lakes Ph 3b-4, 3b-5 & 3b-7 83/27 Lot 184
County: Orange
Year built: 2017
Living area: 2,839 sq ft
Price/sq ft: $245
Lot size: 9,798 sq ft
Lot category: 0 to less than 1/4
Flood zone: X (12095C0380H)
Garage: 2 spaces
Annual taxes: $9,648 (2025)
Parcel #: 16-23-27-8135-01-843
Zoning: P-D
MLS #: O6376219

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Interior Details

Bedrooms: 4
Full bathrooms: 3
Half bathrooms: 1
Flooring: Carpet, Ceramic Tile
Appliances: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Washer
Interior features: Ceiling Fans(s), Primary Bedroom Main Floor
Laundry: Laundry Room, Washer Hookup
Stories / Levels: Two
Direction faces: East

Heating & Cooling

Heating: Central, Natural Gas
Cooling: Central Air

Parking

Garage spaces: 2
Attached garage: No
Carport: Yes

HOA & Financial

HOA fee: $195 / Monthly
Monthly HOA: $195/mo
Total monthly fees: $195/mo
Total annual fees: $2,340
HOA name: Tyler Parsons
CDD: No
Homestead exemption: Yes
Min lease term: 7 Months
Listing terms: Cash, Conventional, FHA, Other, VA Loan
Ownership: Fee Simple
Available for lease: Yes
Lease restrictions: Yes
Additional lease restrictions: Buyer and buyer’s agent are solely responsible for verifying all information, including but not limited to property details, restrictions, square footage, HOA rules, and any use limitations. Listing agent and seller make no representations or warranties.

Exterior & Construction

Exterior features: Garden
Construction materials: Stucco
Roof: Shingle
Foundation: Concrete Perimeter
Road surface: Asphalt

Utilities

Sewer: Public Sewer
Water source: Public
Utilities: Cable Available, Electricity Available, Electricity Connected, Public, Water Connected

Community

Pets allowed: Yes

Schools

ElementaryAIndependence ElementaryGreatSchools ↗

MiddleABridgewater MiddleGreatSchools ↗

High SchoolAWindermere High SchoolGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

Room	Level	Dimensions
Primary Bedroom	First	14x15
Bathroom 2	Second	15x12
Bathroom 3	Second	12x12
Bedroom 4	Second	12x12
Loft	Second	12x12
Dining Room	First	11x12
Family Room	First	19x17
Living Room	First	20x8
Balcony/Porch/Lanai	First	13x9
Balcony/Porch/Lanai	First	13x9
Kitchen	First
Primary Bathroom	First

Listing Details

Listing date: 2026-01-21
On market date: 2026-01-23
Original list price: $719,000
Occupant type: Owner
MLS area: 34787 - Winter Garden/Oakland
Listing AOR: Suncoast Tampa
Status changed: 2026-01-23
Tax legal description: SIGNATURE LAKES PHASE 3B-4, 3B-5 AND 3B-7 83/27 LOT 1843

Flood risk

Minimal riskFEMA Zone XPanel 12095C0380H

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of April 26, 2026 at 10:44 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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