$455,000
5755 Cypress Hill Road
Winter Garden, FL 34787
Property type
Year built
Lot size
Price / sq ft
HOA dues
Days on market
Garage spaces
Flood zone
About 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.
Local Insight
At $253/sqft for a 2019 townhouse in a rapidly expanding area, you're getting decent value, but the $338 monthly HOA is on the steeper side—make sure you factor that into your true cost of ownership over time. Winter Garden/Cypress Hill has exploded (315% population growth since 2010), which means strong long-term appreciation potential but also increasingly heavy traffic and school crowding, especially as you're looking at Keene Crossing Elementary and Bridgewater Middle, both absorbing significant new residents. The flood zone X designation is a real plus here, but verify the HOA reserves and any upcoming assessments before committing, since newer developments in fast-growth areas often face surprise special assessments once the community matures.
AI-generated insight based on listing data and neighborhood context. Verify independently.
Estimated monthly payment
Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.
Price & listing history4 days on market
- Status: ActiveMay 3, 2026
- Listed$455,000May 3, 2026
- Price increased$455,000
Virtual Tour
Facts & features
- Property type
- Residential
- Sub type
- Townhouse
- Status
- Active
- Days on market
- 4
- Subdivision
- Orchard Hills Ph 4
- County
- Orange
- Year built
- 2019
- Living area
- 1,797 sq ft
- Price/sq ft
- $253
- Building area
- 2,439 sq ft (Public Records)
- Lot size
- 4,180 sq ft
- Lot category
- 0 to less than 1/4
- Flood zone
- X (12095C0380H)
- Garage
- 2 spaces
- Annual taxes
- $4,506 (2025)
- Parcel #
- 15-23-27-5856-06-040
- Zoning
- P-D
- MLS #
- O6404161
Ask about this home
Have a question? Ask the broker directly.
Ryan Solberg answers personally — no call center, no spam. Your question goes straight to him.
Interior Details
- Bedrooms
- 3
- Full bathrooms
- 2
- Half bathrooms
- 1
- Flooring
- Carpet, Tile
- Appliances
- Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator, Washer
- Interior features
- Kitchen/Family Room Combo, PrimaryBedroom Upstairs, Stone Counters, Thermostat, Walk-In Closet(s)
- Laundry
- Inside, Laundry Room, Upper Level
- Stories / Levels
- Two
- Direction faces
- Southwest
Heating & Cooling
- Heating
- Central
- Cooling
- Central Air
Parking
- Garage spaces
- 2
- Attached garage
- Yes
- Parking features
- Driveway
HOA & Financial
- HOA fee
- $1,015 / Quarterly
- Monthly HOA
- $338/mo
- Total monthly fees
- $338/mo
- Total annual fees
- $4,060
- HOA name
- Orchard Hills
- CDD
- No
- Homestead exemption
- Yes
- Min lease term
- 7 Months
- Listing terms
- Cash, Conventional, VA Loan
- Ownership
- Fee Simple
- Available for lease
- Yes
- Lease restrictions
- Yes
- Additional lease restrictions
- Verify with HOA
- Approval process
- Verify with HOA
Exterior & Construction
- Exterior features
- Rain Gutters, Sidewalk
- Construction materials
- Block, Stucco
- Roof
- Shingle
- Foundation
- Slab
- Road surface
- Asphalt
Utilities
- Sewer
- Public Sewer
- Water source
- Public
- Utilities
- Cable Available
Community
- Pets allowed
- Breed Restrictions
Schools
Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.
Room Details
| Room | Level | Dimensions |
|---|---|---|
| Kitchen | First | |
| Great Room | First | |
| Primary Bedroom | Second | |
| Primary Bathroom | Second | |
| Bedroom 2 | Second |
Listing Details
- Listing date
- 2026-05-01
- On market date
- 2026-05-03
- Original list price
- $455,000
- Occupant type
- Owner
- MLS area
- 34787 - Winter Garden/Oakland
- Listing AOR
- Orlando Regional
- Status changed
- 2026-05-03
- Tax legal description
- ORCHARD HILLS PHASE 4 91/129 LOT 604
Flood risk
Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.
Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.
Location
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.
More homes like this
$434,900
5686 Cypress Hill Rd
Winter Garden, FL 34787
3 bd · 3 ba · 1,712 sqft
Orchard Hills Ph 4
MLS# O6410760
$460,000
5706 Cypress Hill Rd
Winter Garden, FL 34787
3 bd · 3 ba · 1,712 sqft
Orchard Hills Ph 4
MLS# O6386620
$546,490
6279 Sunny Time Avenue
Winter Garden, FL 34787
3 bd · 3 ba · 1,913 sqft
Silverleaf Oaks
MLS# O6412141
$600,000
14542 Black Cherry Trl
Winter Garden, FL 34787
4 bd · 3 ba · 2,234 sqft
Signature Lks-Pcl 01d Ph 01
MLS# O6410574
Listings courtesy of Stellar MLS as distributed by MLS GRID
IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Based on information submitted to the MLS GRID as of May 7, 2026 at 6:53 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA