5966 CYPRESS HILL ROAD, WINTER GARDEN, FL 34787 | MLS #MFRO6376219 | Berkshire Hathaway HomeServices Florida Network Realty
Maria Wilkes

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Listing provided courtesy of DALTON WADE INCas Distributed by MLSGrid- MLS# MFRO6376219MLS Provider

5966 CYPRESS HILL ROADWINTER GARDEN, FL 34787

Single Family · 4 Beds · 3 Full Baths · 1 Half Bath · 2,839 Sq. ft. | 0.22 Acres
$695,000 Active

5966 CYPRESS HILL ROAD Overview

Time on Site:
158 days
Visits:
0

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.

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5966 CYPRESS HILL ROAD Facts & Features

  • Type Single Family
  • Sq. ft. 2,839
  • Price/Sq.ft. $245
  • Lot 0.22 Acres

Details

General

Association/HOA

  • Association Amenities: Clubhouse,Fitness Center,Park,Playground,Pool
  • Association Fee: 195
  • Association Fee Frequency: Monthly
  • Association Fee Includes: Internet
  • Association Name: Tyler Parsons
  • Association: Yes

School Information

  • Elementary School: Independence Elementary
  • Middle Or Junior School: Bridgewater Middle
  • High School: Windermere High School

Green Features

  • Green Energy Generation: Solar

Building Information

  • New Construction: No
  • Year Built: 2017

Location/Region

  • Country: US
  • County Or Parish: Orange
  • MLS Area Major: 34787 - Winter Garden/Oakland
  • Subdivision Name: SIGNATURE LAKES PH 3B-4, 3B-5 & 3B-7 83/27 LOT 184
  • Township: 23

Community/Development

  • Community Features: Clubhouse,Dog Park,Fitness Center,Park,Playground,Pool,Sidewalks

Tax Information

  • Tax Annual Amount: 9648
  • Tax Year: 2025

General Information

  • Furnished: Unfurnished
  • Listing Terms: Cash,Conventional,FHA,Other,VA Loan
  • Ownership: Fee Simple
  • Parcel Number: 16-23-27-8135-01-843
  • Pets Allowed: Yes
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Senior Community: No
  • Special Listing Conditions: None
  • Zoning: P-D

Interior

Parking Information

  • Garage Spaces: 2
  • Garage: Yes

Beds/Baths

  • Bathrooms Full: 3
  • Bathrooms Half: 1
  • Bathrooms Total: 4
  • Bedrooms Total: 4

Building Interior

  • Building Area Source: Public Records
  • Building Area Total: 2839
  • Building Area Units: Square Feet

General Information

  • Appliances: Cooktop,Dishwasher,Disposal,Dryer,Microwave,Washer
  • Cooling: Central Air
  • Fireplace: No
  • Flooring: Carpet,Ceramic Tile
  • Foundation Details: Concrete Perimeter
  • Heating: Central,Natural Gas
  • Interior Features: Ceiling Fans(s),Primary Bedroom Main Floor
  • Laundry Features: Laundry Room,Washer Hookup
  • Levels: Two
  • Living Area: 2839
  • Living Area Source: Public Records
  • Living Area Units: Square Feet
  • Other Equipment: Irrigation Equipment
  • Stories Total: 2

Exterior

Lot Information

  • Additional Parcels: No
  • Lot Size Acres: 0.22
  • Lot Size Square Feet: 9798
  • Road Surface Type: Asphalt
  • Water Source: Public

Waterfront/View

  • Waterfront: No

Building Exterior/Construction

  • Attached Garage: No
  • Construction Materials: Stucco
  • Direction Faces: East
  • Roof: Shingle

General Information

  • Carport Spaces: 1
  • Carport: Yes
  • Exterior Features: Garden
  • Pool Private: No
  • Sewer: Public Sewer
  • Utilities: Cable Available,Electricity Available,Electricity Connected,Public,Water Connected

Room Information

Room: Balcony/Porch/Lanai

  • Level: First
  • Dimensions: 13x9
  • Length: 9
  • Width: 13

Room: Balcony/Porch/Lanai

  • Level: First
  • Dimensions: 13x9

Room: Dining Room

  • Level: First
  • Dimensions: 11x12
  • Length: 12
  • Width: 11

Room: Family Room

  • Level: First
  • Dimensions: 19x17
  • Length: 17
  • Width: 19

Room: Kitchen

  • Level: First

Room: Living Room

  • Level: First
  • Dimensions: 20x8
  • Length: 8
  • Width: 20

Room: Primary Bathroom

  • Level: First

Room: Primary Bedroom

  • Level: First
  • Dimensions: 14x15
  • Length: 15
  • Width: 14

Room: Bathroom 2

  • Level: Second
  • Dimensions: 15x12
  • Length: 12
  • Width: 15

Room: Bathroom 3

  • Level: Second
  • Dimensions: 12x12
  • Length: 12
  • Width: 12

Room: Bedroom 4

  • Level: Second
  • Dimensions: 12x12
  • Length: 12
  • Width: 12

Room: Loft

  • Level: Second
  • Dimensions: 12x12
  • Length: 12
  • Width: 12

5966 CYPRESS HILL ROAD Neighborhood

Community

34787 (WINTER GARDEN) Demographics

37
Median Age
941
Population Density (per sq. mile)
54%
College Educated
$94,038
Estimated Median Income
17,911
Estimated Total Home Owners
6,766
Estimated Total Renters
73% / 27%
Estimated Owner / Renter Divide
3
Estimated Average Household Size
Community data courtesy of LiveBy, Inc.

Schools

School data courtesy of LiveBy, Inc. School ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating.

5966 CYPRESS HILL ROAD Monthly Cost

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Dylan Leitman
* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

5966 CYPRESS HILL ROAD Market Data

Based on the last 30 days in this zip code

$715,510
Average List Price
$287
Average Price per Square Foot
154
Properties Sold
104
Average Days on Market
1,100
Properties for Sale
Calculations provided by Reliance Network

5966 CYPRESS HILL ROAD History

Date Event Value Agent
4/26/2026Source: My Florida Regional MLS Price Reduction
$695,000 -3.3%
1/23/2026Source: My Florida Regional MLS Added to Database
January 23, 2026
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022
10/14/2022Source: My Florida Regional MLS Added to Database
October 14, 2022