Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$455,000 Just Listed

  • For Sale
  • Active
  • Townhouse
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,797 Sq. Ft.
  • Updated 4 days ago
See This Home
Save This Home
See This Home
Save This Home
Welcome to this beautifully maintained corner townhouse in the sought-after Orchard Hills community of Winter Garden, offering 3 bedrooms, 2.5 baths, a 2-car garage, and abundant natural light throughout. As you enter the home, you are welcomed into the dining area which then flows seamlessly into the spacious living room and kitchen, creating an inviting layout perfect for everyday living and entertaining. Tile flooring extends throughout the downstairs living areas, kitchen, and wet areas for style and easy maintenance. The kitchen features stunning granite countertops that contrast beautifully with the white cabinetry, along with stainless steel appliances all included. Upstairs, you'll find all three bedrooms with comfortable carpet flooring, as well as a convenient laundry room complete with washer and dryer. The primary bedroom offers private access to a balcony where you can enjoy peaceful water views and relax in a serene outdoor setting. Residents of Orchard Hills enjoy exceptional amenities including a clubhouse, fitness center, picnic area with grills, dog park, playground, and a vibrant community atmosphere with events and social clubs designed to build lasting relationships.

Full Property Details for 5755 Cypress Hill Rd

General

  • Price: $455,000
  • HOA FEE: $338/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $4,506 (2025)
  • Status: Active
  • Type: Townhouse
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6404161
  • Updated: 5/3/2026
  • Added to Site: 5 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 5
  • Interior Features: Kitchen and Family Room Combination, PrimaryBedroom Upstairs, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room, Upper Level

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Park, Playground, Pool, Recreation Facilities

Exterior

  • Exterior Features: Rain Gutters, Sidewalk

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: ORCHARD HILLS PH 4
  • Driving Directions: From Florida’s Turnpike, take the exit for SR429 North toward Apopka. Take exit to Schofield Rd and turn left and turn right onto Avalon Road, then turn left on Orchard Hills Blvd. Turn onto Cypress Hill Rd.
  • Direction Faces: Southwest

School Information

  • Elementary School: Keene Crossing Elementary
  • Middle School: Bridgewater Middle
  • High School: Windermere High School

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Clubhouse, Dog Park, Fitness Center, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Clubhouse, Fitness Center, Park, Playground, Pool, Recreation Facilities
  • Association: Yes
  • Assoc. Name: Orchard Hills
  • Assoc. Fees Include: Community Pool, Maintenance Grounds, Pool Maintenance, Recreational Facilities
  • Pet Restrictions: Verify with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable TV Available

Structural Information

  • Architectural Info: Contemporary
  • Architectural Style: Contemporary
  • Exterior Const.: Block, Stucco
  • Roof: Shingle
  • Windows: Drapes
  • Stories/Levels: Two
  • Square Feet: 1,797
  • Sq. Ft. Source: Public Records
  • Year Built: 2019

Lot Features

  • Lot Size (Acres): 0.1
  • Lot Size (Sq. Ft.): 4,180
  • Lot Size: 4180
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt

Financial Considerations

  • Association Fee: $1,015
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,506.07
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ORCHARD HILLS PHASE 4 91/129 LOT 604
  • Flood Zone Info: X
  • APN: 152327585606040
  • Property ID: 152327585606040

Listed by Ct Homes Realty Corporation

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5755 Cypress Hill Rd —

  • Ct Homes Realty Corporation

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5755 Cypress Hill Rd

School District:Orange County School District
NameGradesDistance
Keenes Crossing Elementary School
5240 Keenes Pheasant Drive, Windermere, FL 34786
PK-50.4 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-80.6 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5755 Cypress Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/03/2026
Listed
$455,000
46.3%
MLS
8/14/2020
Sold
$311,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5755 Cypress Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,506
6%
$284,485
6%
2024
$4,270
7%
$269,199
3%
2023
$3,973
6%
$261,358
6%
2021
$3,762
-1%
$246,355
-3%
2022
$3,806
1%
$253,746
7%
2021
$3,762
266%
$237,704
579%
2019
$1,028
28%
$35,000
—
2018
$805
38%
$35,000
—
2017
$582
—
$35,000
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5755 Cypress Hill Rd

$
Down Payment
%
$
%

$
$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Ct Homes Realty Corporation

Similar Properties near 5755 Cypress Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

13733 Bressler Aly, Windermere, FL 34786 - Photo 1
$455,000

13733 Bressler Aly  Windermere, FL 34786

  • Townhouse
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 2,002
    Sq. Ft.
Listed by Corcoran Premier Realty
7327 Millstone St, Windermere, FL 34786 - Photo 1
$459,000

7327 Millstone St  Windermere, FL 34786

  • Townhouse
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 1,531
    Sq. Ft.
Listed by Compass Florida Llc
12333 Via Derna Pl, Windermere, FL 34786 - Photo 1
$459,000

12333 Via Derna Pl  Windermere, FL 34786

  • Townhouse
  • Active
  • 3
    Beds
  • 3
    Total Baths
  • 1,919
    Sq. Ft.
Listed by Yellow Rock Realty Corp
5706 Cypress Hill Rd, Winter Garden, FL 34787 - Photo 1
$460,000

5706 Cypress Hill Rd  Winter Garden, FL 34787

  • Townhouse
  • Active
  • Updated 12 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,712
    Sq. Ft.
Listed by Wra Business & Real Estate

Just Listed near 5755 Cypress Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

16802 Sugar Berry Ln, Montverde, FL 34756 - Photo 1 Just Listed
$202,000

16802 Sugar Berry Ln  Montverde, FL 34756

  • Mobile Home
  • Active
  • Updated 51 minutes ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,456
    Sq. Ft.
Listed by Arellano Realty & Investments
16846 Florence View Dr, Montverde, FL 34756 - Photo 1 Just Listed
$575,000

16846 Florence View Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 18 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,972
    Sq. Ft.
Listed by Kw Coastal Living Ii
1433 Shira Rd, Minneola, FL 34715 - Photo 1 Just Listed
$600,000

1433 Shira Rd  Minneola, FL 34715

  • Single Family
  • Active
  • Updated 5 hours ago
  • 5
    Beds
  • 4
    Total Baths
  • 2,700
    Sq. Ft.
Listed by Don Harkins Realty Llc
1234 Whispering Ln, Minneola, FL 34715 - Photo 1 Just Listed
$659,990
Open House

1234 Whispering Ln  Minneola, FL 34715

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,021
    Sq. Ft.
Listed by Exp Realty Llc

Price Reduced near 5755 Cypress Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

15966 Winding Bluff Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$20,000 (-2.99%)
$649,000

15966 Winding Bluff Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 2 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,037
    Sq. Ft.
Listed by Dw&Co. Real Estate, Llc
15742 Vetta Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$10,000 (-1.16%)
$850,000

15742 Vetta Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 2,817
    Sq. Ft.
Listed by Redfin Corporation
15436 Vinola Dr, Montverde, FL 34756 - Photo 1 Price Reduced
-$1 (0%)
$1,149,000

15436 Vinola Dr  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,079
    Sq. Ft.
Listed by Charles Rutenberg Realty Orlando
17034 Medici Way, Montverde, FL 34756 - Photo 1 Price Reduced
-$50,000 (-2.09%)
$2,345,000

17034 Medici Way  Montverde, FL 34756

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 6
    Total Baths
  • 5,878
    Sq. Ft.
Listed by Vista Cay Realty Company

Recent Sales near 5755 Cypress Hill Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

14815 Driftwater Dr, Winter Garden, FL 34787 - Photo 1 Sold
$425,000

14815 Driftwater Dr  Winter Garden, FL 34787

  • Townhouse
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 1,997
    Sq. Ft.
Listed by Fathom Realty Fl Llc
Sold by The Simon Simaan Group
14897 Evergreen Oak Loop, Winter Garden, FL 34787 - Photo 1 Sold
$410,000

14897 Evergreen Oak Loop  Winter Garden, FL 34787

  • Townhouse
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 1,748
    Sq. Ft.
Listed by Keller Williams Realty At The Parks
Sold by Exp Realty Llc
5771 Mangrove Cove Ave, Winter Garden, FL 34787 - Photo 1 Sold
$515,000

5771 Mangrove Cove Ave  Winter Garden, FL 34787

  • Single Family
  • Closed
  • 3
    Beds
  • 3
    Total Baths
  • 2,124
    Sq. Ft.
Listed by Florida Connexion Properties
Sold by Eternity Realty Llc
14717 Magnolia Ridge Loop, Winter Garden, FL 34787 - Photo 1 Sold
$515,000

14717 Magnolia Ridge Loop  Winter Garden, FL 34787

  • Single Family
  • Closed
  • Updated 2 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,770
    Sq. Ft.
Listed by Lifestyle International Realty
Sold by Homesmart

5755 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6404161) is a Townhouse property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 5755 Cypress Hill Road is currently listed for $455,000 and was received on May 03, 2026. Want to learn more about 5755 Cypress Hill Road? Do you have questions about finding other Townhouse real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

Tour this property