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Overview

3 bd2 ba1,616 sqftSingle Family
TypeSingle Family
HOANone listed
Built1950
Lot8,440 sqft
Living area1,616 sqft
Price / sqft$248

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Pricing, comps, HOA, the neighborhood. Answers before you fill out anything.

About this home

Kitchen/Family Room ComboStone CountersVaulted Ceiling(s)LightingDishwasherMicrowaveRangeRefrigerator

420 E Cypress St is a 1950-built home in Overstreet Crate, Winter Garden. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,616 square feet of living space. Listed at $400,000 (about $248/sqft), 138 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

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.

The essentials

Built
1950
Price / sqft
$248
On market
138 days
Annual tax
$5,517
Flood zone
X · Low risk
Lot
8,440 sqft
Type
Single Family Residence

At a glance

Single family
Built 1950
8,440 sqft lot
Lot size
1,616 sqft
Living area

Payment

Est. monthly payment
$2,746/mo
Down payment (20%)
$80,000
Property taxes
$460/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1950
Lot
8,440 sqft
Cooling
Central Air
Heating
Central
Parking
-
Days on Market
138
Kitchen/Family Room Combo
Stone Counters
Vaulted Ceiling(s)
Lighting
Dishwasher
Microwave
Range
Refrigerator
Elementary
Maxey Elem
Middle
Lakeview Middle
High
West Orange High

Districts can re-zone, so verify directly with the district before relying on these.

Flood Zone X
Annual Tax (2025)
$5,517
Parcel #
12-22-27-6496-20-028

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
Overstreet Crate
County
Orange
MLS Area
34787 - Winter Garden/Oakland
Lot Size
8,440 sqft

Price history

Date
Event
Price
10/12/2026
Price change
Source: Stellar MLS #O6412414
$400,000-2.4%
$248/sqft
-
Price change
Source: Stellar MLS #O6412414
$410,000-3.5%
$254/sqft
6/1/2026
Listed for sale
Source: Stellar MLS #O6412414
$425,000
$263/sqft

Neighborhood

420 E Cypress St
Winter Garden, FL, 34787 · 34787 - Winter Garden/Oakland

Market insights

Offer Insights

Choose an offer strength

List price: $400,000
$397,500 – $400,000
99.5% – 100% of listTops out right at the list price
80% of listList price
221 of the last 441 home closings in 34787 landed at this number or higher (50%). The median one sat 22 days before it went under contract, and this one is on day 138 after a $25,000 cut.

Sample: 441 closed home sales in 34787 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$2,746/mo
Principal & interest$2,086
Property taxes$460
Insurance$200
Down payment20% · $80,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$400,000

$248 per sq ft

Beds and baths

3 beds, 2 baths

Size

1,616 sq ft

Time on market

138 days

Year built

1950

Monthly payment

About $2,746/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $5,517 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byKELLER WILLIAMS ELITE PARTNERS III REALTYListing agent: Trevor ZwickListing data from Stellar MLS, MLS# O6412414.

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