Orlando Realtor Specializing in Family Relocation

Helping families move near Walt Disney World without the tourist traffic

420 E CYPRESS STREET
WINTER GARDEN, FL, 34787
$425,000
3 Beds
2 Baths
1,616 SqFt
0.19 Acres
Add
MLS #O6412414 image #0
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.

Property Details

Price:
$425,000
MLS #:
O6412414
Status:
Active
Beds:
3
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OVERSTREET CRATE
Neighborhood:
34787wintergardenoakland
Listed Date:
Jun 1, 2026
Finished Sq Ft:
1,616
Total Sq Ft:
1,616
Lot Size:
8,440 sqft / 0.19 acres (approx)
Year Built:
1950
34787 – Winter Garden/oakland34787wintergardenoaklandOverstreet CrateMaxey ElemLakeview MiddleWest Orange HighBuyer And Buyer’s Agent Must Verify Any Restrictions.No Minimum

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Maxey Elem
Middle School:
Lakeview Middle
High School:
West Orange High

Interior

Appliances
Dishwasher, Microwave, Range, Refrigerator
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Luxury Vinyl
Heating
Central
Interior Features
Kitchen/Family Room Combo, Stone Counters, Vaulted Ceiling(s)
Laundry Features
Other
Levels
One

Exterior

Construction Materials
Stucco, Wood Frame
Direction Faces
North
Exterior Features
Lighting, Other
Fencing
Fenced, Vinyl
Roof
Shingle

Financial

Tax Year
2025
Taxes
$5,517

Map

Community

Subdivisions in WINTER GARDEN

Market Summary

Current real estate data for Single Family in WINTER GARDEN as of Jun 09, 2026
833
Single Family Listed
105
Avg DOM
280
Avg $ / SqFt
$766,868
Avg List Price

Property Summary

    Located in the OVERSTREET CRATE subdivision, 420 E CYPRESS STREET WINTER GARDEN FL is a Single Family for sale in WINTER GARDEN, FL, 34787. It is listed for $425,000 and features 3 beds, 2 baths, and has approximately 1,616 square feet of living space, and was originally constructed in 1950. The current price per square foot is $263. The average price per square foot for Single Family listings in WINTER GARDEN is $280. The average listing price for Single Family in WINTER GARDEN is $766,868. To schedule a showing of MLS#o6412414 at 420 E CYPRESS STREET in WINTER GARDEN, FL, contact your Preferred Real Estate Brokers agent at 4076987254.

Similar Listings Nearby

broker reciprocity
MLS# O6391938broker reciprocity
1626 REGAL RIVER CIRCLE
OCOEE, FL

$550,000

3.6 miles away

broker reciprocity
MLS# O6410232broker reciprocity
1028 SPRING LANDING DRIVE
WINTER GARDEN, FL

$550,000

2.3 miles away

broker reciprocity
MLS# O6400904broker reciprocity
776 RAINFALL DRIVE
WINTER GARDEN, FL

$550,000

2.0 miles away

broker reciprocity
MLS# S5150294broker reciprocity
909 GROVESMERE LOOP
OCOEE, FL

$549,999

2.6 miles away

broker reciprocity
MLS# O6408720broker reciprocity
46 W VINING STREET
WINTER GARDEN, FL

$549,900

0.6 miles away

broker reciprocity
MLS# S5142675broker reciprocity
512 GARDEN HEIGHTS DRIVE
WINTER GARDEN, FL

$549,900

1.7 miles away

broker reciprocity
MLS# O6410568broker reciprocity
1348 OLYMPIA PARK CIRCLE
OCOEE, FL

$540,000

3.3 miles away

broker reciprocity
MLS# S5148787broker reciprocity
113 W DIVISION STREET
WINTER GARDEN, FL

$539,900

1.3 miles away

broker reciprocity
MLS# O6379741broker reciprocity
2065 WHITE FEATHER LOOP
OAKLAND, FL

$539,900

4.7 miles away

broker reciprocity
MLS# G5113349broker reciprocity
1061 PORTMOOR WAY
WINTER GARDEN, FL

$535,000

3.1 miles away

420 E CYPRESS STREET
WINTER GARDEN, FL