5966 Cypress Hill Rd

Winter Garden, FL 34787

$719,000
Price
4
Beds
2,839 Sq. Ft.
$253 / Sq. Ft.
2,839
Sq. Ft.
$253
per Sq. Ft.
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Virtual Tour

Description

Welcome to 5966 Cypress Hill Rd, located in the highly desirable Independence community of Winter Garden. This beautifully maintained home offers a rare combination of privacy, space, and lifestyle perks that truly set it apart. One of the standout features is the solar system that will be fully paid off prior to closing, allowing the next owner to enjoy very low electric bills (approximately $35/month) — a huge long-term savings and peace of mind. The home sits on a larger lot than most homes in...Welcome to 5966 Cypress Hill Rd, located in the highly desirable Independence community of Winter Garden. This beautifully maintained home offers a rare combination of privacy, space, and lifestyle perks that truly set it apart. One of the standout features is the solar system that will be fully paid off prior to closing, allowing the next owner to enjoy very low electric bills (approximately $35/month) — a huge long-term savings and peace of mind. The home sits on a larger lot than most homes in the community and backs to an open area with no rear neighbors, creating a quiet, private setting perfect for relaxing or entertaining. The covered side lanai, long driveway, and detached garage add both functionality and a luxury feel, with plenty of space for parking and gatherings. Located in the sought-after Independence community, residents enjoy an unmatched lifestyle with:

Two private boat ramps with access to Lake Speer and Lake Hancock

Two clubhouses, resort-style pools, fitness centers, and basketball courts

Internet included through Spectrum as part of the HOA

Miles of walking trails, parks, and green spaces

Weekly community events such as food trucks and movie nights

The home is zoned for A-rated schools, including Independence Elementary, Bridgewater Middle, and Windermere High School, all nearby. This is a quiet, well-kept, family-friendly community that offers both convenience and a true neighborhood feel — close to shopping, dining, major highways, and everything Central Florida has to offer. Water softener is not included in the sale but may be purchased separately. This is a rare opportunity to own a home with privacy, energy efficiency, and resort-style amenities in one of Winter Garden’s most loved communities.
  1. Listed by Mahmoud Mango • Brokerage DRE #1047837 • DALTON WADE INC
    P: (321)-830-4678 C: (321)-830-4678 info@mangosrealty.com

Property Details for 5966 Cypress Hill Road

Subdivision Name
SIGNATURE LAKES PH 3B-4, 3B-5 & 3B-7 83/27 LOT 184
Township
23
Carport Spaces
1
Garage Spaces
2
Waterfront
No
Furnished
Unfurnished
LISTING UPDATED: 01/24/2026 06:57 AM

Property Details for 5966 Cypress Hill Road

StatusActive
MLS #O6376219
Days on Market2
Taxes$9,648 / year
HOA Fees$2,340 / year
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family Residence
Year Built2017
Lot Size0.22 AC / 9,798 SF
CountyOrange County

Location

Listing Courtesy of DALTON WADE INC, Mahmoud Mango
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Building Information for 5966 Cypress Hill Road

Stories2Year Built2017Building Size-Lot Size0.22 AC / 9,798 SF

Payment Calculator

$4,503 per month

30 year fixed, 6.15% Interest

Principal and Interest

$3,504

Property Taxes

$804

HOA Dues

$195

The Payment Calculator is for illustrative purposes only.

Property Information for 5966 Cypress Hill Road

Summary
Location and General Information
  • Building Area Source: Public Records
  • Building Area Total: 2839.0
  • Building Area Units: Square Feet
  • Community Features: Boat Slip, Fishing, Lake, Private Boat Ramp, Clubhouse, Dog Park, Fitness Center, Park, Playground, Pool, Sidewalks
  • Direction Faces: East
  • 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.
  • Elementary School: Independence Elementary
  • Middle Or Junior School: Bridgewater Middle
  • High School: Windermere High School
  • Mls Major Change Type: New Listing
  • Major Change Type: New Listing
  • Listing Service: Full Service
  • Senior Community: No
  • Unit Number: No
  • Street Number: 5966
  • Street Name: CYPRESS HILL
  • Street Suffix: ROAD
  • State: FL
  • City: WINTER GARDEN
Parking
  • Attached Garage: No
  • Carport: Yes
  • Garage: Yes
Taxes and HOA Information
  • Association Approval Required: No
  • Association Fee Includes: Internet
  • Association Fee Requirement: Required
  • Association Name: Tyler Parsons
  • Association Phone: 4076547479
  • Association: Yes
  • CDD: No
  • Pet 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.
  • Tax Block: 83/27
  • Tax Book Number: 83/27
  • Tax Legal Description: SIGNATURE LAKES PHASE 3B-4, 3B-5 AND 3B-7 83/27 LOT 1843
  • Tax Lot: 1843
  • Tax Year: 2025
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Property
Lot Information
  • Additional Parcels: No
  • Parcel Number: 162327813501843
  • Total Acreage: 0 to less than 1/4
  • Water Access: No
  • Water Extras: No
  • Zoning: P-D
  • Living Area: 2839
Property and Assessments
  • Year Built Numeric: 2017
  • Association Amenities: Clubhouse, Fitness Center, Park, Playground, Pool
  • Flood Zone Code: X
  • Flood Zone Date: 09-24-2021
  • Flood Zone Panel: 12095C0380H
  • Homestead: Yes
  • New Construction: No
  • Public Survey Range: 27
  • Public Survey Section: 16
Utilities
  • Electric: Photovoltaics Seller Owned
  • Green Energy Generation: Solar
  • Sewer: Public Sewer
  • Utilities: Cable Available, Electricity Available, Electricity Connected, Public, Solar, Water Connected
  • Water Source: Public
Interior and Exterior Features
Exterior Features
  • Construction Materials: Stucco
  • Exterior Features: Garden, Irrigation System
  • Foundation Details: Concrete Perimeter
  • Levels: Two
  • Pool Private: No
  • Pool: Community
  • Pool Private: Yes
  • Roof: Shingle
  • Waterfront Features: Lake
  • Waterfront Feet Total: 0
  • Number Of Stories: 2
Interior Features
  • Bedrooms Total: 4
  • Bathrooms Full: 3
  • Additional Rooms: Loft
  • Appliances: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Washer
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Carpet, Ceramic Tile
  • Heating: Central, Natural Gas
  • Interior Features: Ceiling Fan(s), Primary Bedroom Main Floor
  • Laundry Features: Laundry Room, Washer Hookup
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Room Count: 12.0
  • Water View: No
  • Bathrooms Half: 1
Rental
Rental Information
  • Minimum Lease Period: 0
  • Pets Allowed: Yes

Property History for 5966 Cypress Hill Road

DateEvent & SourcePriceAppreciation
Jan 23, 2026

Listed (Active)

MFRMLS #O6376219

$719,000—
Dec 15, 2021

Sold (Public Record)

Public Record #1480282616

$516,000

+7.0% / yr

Dec 15, 2021

Sold

MFRMLS #O5976348

$516,000—
Oct 14, 2021

Pending

MFRMLS #O5976348

—
Sep 29, 2021

Listed (Active)

MFRMLS #O5976348

$516,000—
Mar 20, 2017

Sold (Public Record)

Public Record #592627797

$373,900—
DateEvent & SourcePrice
01/23/2026

Listed (Active)

MFRMLS #O6376219

$719,000
12/15/2021

Sold (Public Record)

Public Record #1480282616

$516,000

+7.0% / yr

12/15/2021

Sold

MFRMLS #O5976348

$516,000
10/14/2021

Pending

MFRMLS #O5976348

—
09/29/2021

Listed (Active)

MFRMLS #O5976348

$516,000
03/20/2017

Sold (Public Record)

Public Record #592627797

$373,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 5966 Cypress Hill Road

Taxable ValueLand$110,000Additions$486,200Total$596,200
Tax Record2024$9,389 ($782 / month)
Home Facts
Beds4Total Finished SqFt2,839 SqFtAbove Grade Finished SqFt2,839 SqFtStories2Lot Size9,809 SqFtStyleSingle Family ResidenceYear Built2017ZoningP-DCountyORANGEAPN16-23-27-8135-01-843

Schools near 5966 Cypress Hill Road

This home is within Orange County Public Schools.
Rating
School
Type
Grades
Distance
Independence Elementary
Public - K to 5
Cornerstone Academy Charter
Charter - K to 8
Bridgewater Middle School
Public - 6 to 8
Windermere High School
Public - 9 to 12
Rating
School
Distance
Independence Elementary
PublicK to 5

Cornerstone Academy Charter
CharterK to 8

Bridgewater Middle School
Public6 to 8

Windermere High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 5966 Cypress Hill Road, Winter Garden, FL 34787

5966 Cypress Hill Road is a single family home for sale in Winter Garden, FL 34787. This property was listed for sale on January 23, 2026 by DALTON WADE INC, it's currently listed at $719,000. It has been on the market for a total of 2 days and was last sold on December 15, 2021. This listing's school district is Orange County Public Schools. Nearby schools include Independence Elementary, Cornerstone Academy Charter and Bridgewater Middle School. 5966 Cypress Hill Road is a 4-bed, 4-bath, 2,839 sqft single family home built in 2017.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of DALTON WADE INC, Mahmoud Mango

The information being provided by MFRMLS and Daytona Multiple Listing Service is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of MFRMLS or Daytona Multiple Listing Service. Real estate listings held by brokerage firms other than this site owner are marked with the IDX/MLS logo. Information deemed reliable but is not guaranteed accurate by MFRMLS or Daytona Multiple Listing Service. Last updated: 01/24/2026 06:57 AM