Gabriella Massaro

Gabriella Massaro Real Estate Agent 🇺🇸

$595,000.00
5561 CYPRESS HILL ROAD, WINTER GARDEN, FL - 34787
3 beds
2.5 baths
2,470 sqft
$595,000.00
5561 CYPRESS HILL ROAD, WINTER GARDEN, FL - 34787
Gabriella Massaro
$595,000.00
3 beds
2.5 baths
2,470 sqft
5561 CYPRESS HILL ROAD, WINTER GARDEN, FL - 34787
For Sale
Photo 1
  • Built in 2016
  • 2 garage spaces
  • $240.89/sqft
  • Lot size: 4,563 sqft

Welcome home to this truly exceptional, move-in ready two-story gem in the highly desirable Orchard Hills community of Winter Garden—showing like a brand-new model home! Meticulously maintained by the owners, this nine-year-old home feels fresh, modern, and beautifully cared for from the moment you arrive. Step inside to an inviting open-concept design featuring stylish wood-look tile throughout the first floor, a bright and spacious living area, and a stunning, modern kitchen complete with a large center island, stainless steel appliances, quartz countertops, and abundant cabinetry—perfect for entertaining or everyday living. A versatile bonus room near the rear of the home offers the ideal space for a home office or guest retreat, along with a convenient half bath and extra storage. Enjoy Florida living with the charming, enclosed patio that connects to the rear-entry two-car garage with additional storage. Upstairs, a generous loft leads to three bedrooms, including a serene primary suite with a private balcony overlooking tranquil pond views. The spa-like ensuite bath features a walk-in shower, soaking tub, and private water closet. Additional upgrades include a full home fire sprinkler system, helping reduce homeowners’ insurance costs, and rain gutters. Residents of Orchard Hills enjoy resort-style amenities, including a pool, clubhouse, fitness center, playgrounds, dog park, and grilling area, while the HOA covers exterior maintenance, lawn care, landscaping, and outdoor pest prevention—making life truly low-maintenance. Just minutes from Disney World, major highways, shopping and dining, this home is a rare opportunity you won't want to miss!

  • Directions: FL 429 to Winter Garden Vineland Rd and 535; turn left on 535, then right on Tilden Rd. and left on Tiny Rd, then left on Cypress Hill Rd. House is on the left.
  • County: Orange
  • Geo subdivision: ORCHARD HILLS PHASE 2

Nearby Schools

Keene Crossing Elementary

Bridgewater Middle

Windermere High School

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent 🇺🇸

See also

For Sale
17682 NORTHLAKE GROVE DRIVE, WINTER GARDEN, FL - 34787
$550,000.00
3 bds
2.5 ba
1,906 sqft
17682 NORTHLAKE GROVE DRIVE, WINTER GARDEN, FL - 34787
For Sale
9203 CUT SHOT DRIVE, WINTER GARDEN, FL - 34787
$578,000.00
5 bds
3.5 ba
2,461 sqft
9203 CUT SHOT DRIVE, WINTER GARDEN, FL - 34787
For Sale
17037 HAGGERTY HOLLOW DRIVE, WINTER GARDEN, FL - 34787
$609,611.00
4 bds
3.5 ba
2,520 sqft
17037 HAGGERTY HOLLOW DRIVE, WINTER GARDEN, FL - 34787
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6383015
Listing updated: February 17, 2026 at 12:19AM
Listing provided by: Kathy McDonald, WATSON REALTY CORP
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