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$625,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 2,204 Sq. Ft.
  • Updated 3 days ago
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Exquisitely upgraded 4-bedroom, 3-bath smart home in the highly sought-after Orchard Hills community of Winter Garden. Situated on a premium lot with no rear neighbors, this move-in-ready home offers a peaceful pond view and exceptional privacy. Soaring ceilings, elegant 20" tile flooring, and abundant natural light enhance the open-concept design. The designer kitchen features upgraded mocha cabinetry, granite countertops, an oversized eat-in island, drinking water filtration system, and a new Samsung refrigerator with transferable warranty through November 2030. High-end upgrades include dimmable lighting throughout, Level 2 EV charger, and a private home theater with Klipsch Reference Premiere speakers, Dolby Atmos surround sound, and a 150" motorized screen (theater components negotiable). Additional highlights include a two-car garage with custom built-in cabinetry and charging station. Residents enjoy resort-style amenities: zero-entry pool, clubhouse, fitness center, playgrounds, dog park, scenic bike trails, and included lawn care and landscaping. Prime location just minutes to Publix, Walmart, Aldi, TJ Maxx, Cinepolis, Urban Air, dining and cafés; 10 minutes to Winter Garden Village, 17 minutes to Costco. Zoned for A-rated, highly sought-after schools within a short bike ride.

Full Property Details for 5531 Cypress Hill Rd

General

  • Price: $625,000
  • HOA FEE: $188/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $8,644 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6378167
  • Updated: 1/30/2026
  • Added to Site: 5 day(s) ago

Rental Information

  • Min. Lease: 6 Months

Interior

  • Number of Rooms: 7
  • Interior Features: Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Primary Bedroom Main Floor, Smart Home, Solid Surface Counters, Stone Counters, Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Disposal, Dryer, Exhaust Fan, Ice Maker, Microwave, Range, Refrigerator, Washer
  • Furnishings: Negotiable
  • Flooring: Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside

Additional Information

  • Shared Amenities: Clubhouse, Fitness Center, Maintenance, Park, Playground, Pool, Recreation Facilities, Trail(s)
  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Irrigation System, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Patio
  • Porch/Patio/Deck: Covered, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: ORCHARD HILLS PH 2 SIGNATURE LAKES
  • Driving Directions: 535 S and right onto Tilden Rd. Left onto Tiny Rd. Left onto Cypress Hill Rd. Home is on the left.
  • Direction Faces: North

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, Deed Restrictions, Dog Park, Fitness Center, Irrigation-Reclaimed Water, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Clubhouse, Fitness Center, Maintenance, Park, Playground, Pool, Recreation Facilities, Trail(s)
  • Association: Yes
  • Assoc. Name: PAUL CLARK
  • Assoc. Fees Include: Community Pool, Maintenance Structure, Maintenance Grounds, Recreational Facilities
  • Pet Restrictions: PER HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Available, Phone Available, Sprinkler Recycled, Water Connected

Structural Information

  • Exterior Const.: Stucco
  • Roof: Shingle
  • Windows: Blinds, Drapes, Window Treatments
  • Stories/Levels: One
  • Square Feet: 2,204
  • Sq. Ft. Source: Public Records
  • Year Built: 2016

Lot Features

  • Lot Size (Acres): 0.15
  • Lot Size (Sq. Ft.): 6,744
  • Lot Size: 6744
  • Street/Road Desc.: Asphalt, Concrete, Paved

Financial Considerations

  • Association Fee: $565
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $8,644
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: ORCHARD HILLS PHASE 2 85/35 LOT 369
  • APN: 152327584903690
  • Property ID: 152327584903690
  • Block/Lot/Section: 369

Listed by Olympus Executive Realty Inc

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Listing agent

— 5531 Cypress Hill Rd —

  • Olympus Executive Realty Inc

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 5531 Cypress Hill Rd

School District:Orange County School District
NameGradesDistance
Keenes Crossing Elementary School
5240 Keenes Pheasant Drive, Windermere, FL 34786
PK-50.7 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-80.5 mi
Windermere High School
5523 Winter Garden Vineland Road, Windermere, FL 34786
9-121.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5531 Cypress Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
1/29/2026
Listed
$625,000
48.81%
MLS
5/14/2021
Sold
$420,000
—
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 5531 Cypress Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$8,584
—
$515,330
4%
2024
$8,584
12%
$496,300
6%
2023
$7,636
74%
$467,335
63%
2021
$4,393
-35%
$286,184
-30%
2022
$6,799
55%
$406,594
44%
2021
$4,393
2%
$282,233
2%
2019
$4,306
1%
$275,888
2%
2018
$4,273
-12%
$270,744
2%
2017
$4,852
277%
$264,637
429%
2016
$1,286
85%
$50,000
25%
2015
$697
—
$40,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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

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NMLS#: 1598647

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Listed by Olympus Executive Realty Inc

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5531 Cypress Hill Road, Winter Garden, FL 34787 (MLS# O6378167) is a Single Family property with 4 bedrooms and 3 full bathrooms. 5531 Cypress Hill Road is currently listed for $625,000 and was received on January 29, 2026. Want to learn more about 5531 Cypress Hill Road? Do you have questions about finding other Single Family 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.

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