Single Family Residence at 420 E CYPRESS ST, WINTER GARDEN
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$410,000

420 E CYPRESS ST
WINTER GARDEN, FL 34787
Listed by Trevor Zwick · KELLER WILLIAMS ELITE PARTNERS III REALTY
Bedrooms
3
Bathrooms
2
Living area
1,616 sqft
Year built
1950

About this home

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

MLS #
MFRO6412414
Property type
Single Family Residence
Subdivision
OVERSTREET CRATE
Status
Active
Days on market
100
On market date
June 1, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
N/A
Parking spaces
N/A
Lot size
0.19 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
WILLIAM S MAXEY ELEMENTARY
0.21 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
423
Student:teacher ratio
14.6:1
District
ORANGE
Middle
LAKEVIEW MIDDLE
1.62 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
2.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
828
Student:teacher ratio
18.8:1
District
ORANGE
High
ORANGE TECHNICAL COLLEGE WESTSIDE CAMPUS
0.51 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
0
Student:teacher ratio
0.0:1
District
ORANGE

Walkability

Blended score for WINTER GARDEN's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

91
Highly walkable
out of 100
EPA National Walkability Index
16.8 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores19
Parks7
Schools20
Transit stops20
Pharmacies9

Market position

How this listing compares to current activity in WINTER GARDEN, from live MLS data.

On the market 100 days -- 25 more days than WINTER GARDEN's current average of 75 days.
For reference, the median list price across 1,032 active listings in WINTER GARDEN right now is $489,070.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$2,619/mo
$82,000 down
$328,000 loan
Principal & interest$2,127
Property tax (est.)$342
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 21 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.