420 E CYPRESS STREET Winter Garden, FL $ 425,000
420 E CYPRESS STREET
$ 425,000
Recently Listed
Open House 6/5 5pm - 7pm
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420 E CYPRESS STREET

Winter Garden, FL, 34787
$ 425,000
Bedrooms3 Baths2.0 Sq 1,616

Monthly Estimate*

$ 2,617

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Single Family Home for sale in Winter Garden, FL

for $425,000 with 3 bedrooms and 2 full baths. This 1,616 square foot home was built in 1950 on a lot size of 0.19.

Welcome to this stunning, fully renovated and fully furnished home, perfectly situated on an oversized lot in one of Winter Garden's most exciting and rapidly growing areas. Whether you're looking for a primary residence, a turnkey investment, or a second home, this move-in-ready property offers the perfect blend of comfort, style, and convenience. Inside, you'll find an open-concept floor plan filled with natural light, featuring all-new flooring, recessed lighting throughout, energy-efficient double-pane windows, and a beautifully updated kitchen complete with stainless steel appliances. Major improvements include a new roof and a 3.5-ton AC system, providing peace of mind for years to come. Step outside and enjoy the spacious, fully fenced backyard, offering plenty of room for entertaining, pets, play, or simply relaxing outdoors. Located just one mile from Historic Downtown Winter Garden, you'll enjoy easy access to award-winning dining, shopping, farmers markets, and community events, all while living in a welcoming, family-friendly neighborhood. Fully furnished, beautifully updated, and truly move-in ready, this home offers a rare opportunity to enjoy all that Winter Garden has to offer from day one.

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Open House

6/5/2026 5:00 PM - 7:00 PM
6/6/2026 1:00 PM - 3:00 PM
6/7/2026 11:00 AM - 3:00 PM
420 E CYPRESS STREET Winter Garden, FL
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 425,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 5,517

Style

Single Family Residence

Lot Size

0.19

Year Built

1950

Town/City

Winter Garden

County/Region

Orange

MLS | Web ID

O6412414

Features
General
Sewer Public Sewer
Heating Central
Cooling Central Air
Utilities Electricity Available
Roof Shingle
Appliances Dishwasher Microwave Range Refrigerator
Zoning R-2
Construction Materials Stucco Wood Frame
Year Built 1950
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Subdivision Name OVERSTREET CRATE
Facing Direction North
Garage Y/N false
Total Rooms 3
Full Baths 2
Status Active
Directions FL-408 W. Exit 267B.Merge onto FL-50 W/W Colonial Dr. Turn right onto 9th St. Turn left onto E Cypress St. Destination will be on the left.
High School West Orange High
City WINTER GARDEN
Senior Community Y/N false
MLS Area 34787 - Winter Garden/Oakland
Lot Size Units Square Feet
Lot Size Square Feet 8440
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Maxey Elem
Land Lease Y/N false
Tax Annual Amount 5517.38
Middle/Junior High School Lakeview Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/O6412414
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Vacant
Tax Lot 28
Legal Description OVERSTREET CRATE COMPANYS F/9 THE E 60 FT OF W 199 FT OF S1/2 OF N1/2 OF S1/2 BLK S IN SEC 23-22-27 SE1/4
Minimum Lease No Minimum
Water Access Y/N false
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Kitchen/Family Room Combo Stone Counters Vaulted Ceiling(s)
Flooring Luxury Vinyl
Furnished Y/N Unfurnished
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Fireplace Y/N false
Half Baths 0
Laundry Features Other
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Lighting Other
Fencing Fenced Vinyl
Water Source Public
Lot Size Area 8440
Foundation Details Slab
Building Area Total 1616
Lot Size Acres 0.19
Road Surface Type Paved
Private Pool false
Waterfront Y/N false
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* Excluded Features
List By
Keller Williams Elite Partners Iii Realty

Broker

trevor@trusttrevor.com

Email

Affordability Calculator

$3,077
Per Month
85%
15%
0%
Monthly Principal & Interest
$2,617
Monthly Property Taxes
$460
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
West Orange High High School High School
Pricing History
DatePricePrice ChangeDescription
6/1/2026$425,000 Listed Price

Map


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420 E CYPRESS STREET, Winter Garden, FL, 34787 is a Single Family Home for sale at $425,000 with 1,616 sqft and a lot size of 0.19. 420 E CYPRESS STREET has 3 bedrooms, 2.0 baths, and was built in 1950. The property's zip code is 34787 which is in Winter Garden, FL