420 E CYPRESS STREET, WINTER GARDEN, FL, 34787
Active53 days on marketListed Jun 1, 2026MLS #O6412414
Come see it
Upcoming open house
Sun, Jul 26
12:30 PM – 3:30 PM
About this home
420 E CYPRESS STREET
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.
Facts & features
The home at a glance
3
Bedrooms
2
Bathrooms
1,616
Sqft
0.19 ac
Lot size
1950
Year built
One
Levels
$254
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Built from this home's actual numbers — the most recent property-tax bill on record — not generic estimates.
$3,215 /mo · 3.5% down FHA, 30-yr fixed at 6%
The assumptions
FHA is the default here because it gets you in the door with just 3.5% down. Switch to Conventional or VA below.
These numbers assume a generic buyer — your credit, down payment and loan program change them. Get the real quote in minutes:
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Run your own numbers
Estimated payment
$3,215/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Taxes reflect the most recent bill on record; insurance is a typical-Florida estimate. Your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Value check
Is the price right?
The internet’s favorite home-value number comes from a single automated model that has never seen the street, the finishes, or the view — which is why it routinely misses by tens of thousands of dollars. The edgeAI estimate combines multiple independent data sources with our team’s on-the-ground expertise in this exact market.
vs edgeAI estimate
−6.4%
$/sqft vs Winter Garden actives
$254 vs $261
Days on market
53 vs 31 typical
Where $254/sqft sits among the 400 Winter Garden actives
The edgeAI estimate is a starting point, not an appraisal or a broker price opinion. It is generated from public records, listing data and market modeling, and is subject to change once a licensed real estate professional personally inspects the property. Condition, floor, view and lot are not fully captured by any model — ask us for a full comparative market analysis.
Where it sits
Inside East Winter Garden
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
East Winter Garden — neighborhood snapshot
Population
4,427
Median age
35
Median income
$48,340
Median home value
$232,691
Avg household
4
Households w/ children
414
For the school run
Orange County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Winter Garden market
$580K → $570K
Winter Garden median sold, yr/yr
97.7%
Sale-to-list ratio (12 mo)
160 of 400
Winter Garden actives have cut their price
Median sold price, Winter Garden, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 23% below the WINTER GARDEN 34787 median. See the full Winter Garden market guide →
Paper trail
This home's history
Reality check
What actually sold near 420 E CYPRESS STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · May ’26$273,000
838 BETHUNE AVENUE · same community
3 bd · 2 ba · 985 sqft · $277/sqft · 64 DOM
Sold · Feb ’26$420,900
774 CITRUS COVE DRIVE
3 bd · 2 ba · 1,613 sqft · $261/sqft · 6 DOM
Sold · Sep ’25$430,000
705 SUNBURST COVE LANE
4 bd · 2 ba · 1,626 sqft · $264/sqft · 43 DOM
Closed-sale data from the MLS, last 12 months, selected for similarity in size and location. No two homes are identical — ask us for a full comparative analysis.
Your home team
The pros in your corner
Buying a home is two conversations — the home and the money. Here’s who handles each, side by side, already working together.
Your agent
David Ramirez
Real Estate Agent · CENTURY 21 Edge
Tours, negotiation, and every question about 420 E CYPRESS STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 420 E CYPRESS STREET — before you fall in love.
See it in person
Schedule a tour
Pick a day that works — this goes straight to David's phone and CRM.
Straight answers
420 E CYPRESS STREET FAQs
What would the monthly payment be for 420 E CYPRESS STREET?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,215/mo — principal and interest, the actual property-tax bill and typical Florida insurance. The payment calculator on this page lets you switch loan type (FHA, Conventional, VA) and adjust the down payment, rate and term.
What are the property taxes on 420 E CYPRESS STREET?+
The most recent tax bill on record (2025) was $5,517. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
How does the price compare to other homes in Winter Garden?+
At $410,000, this home is listed about 31% below the Winter Garden median of $589,945. The market section on this page shows how the area is trending.
Which schools are assigned to 420 E CYPRESS STREET?+
William S Maxey Elementary (elementary), West Orange High (high), Lakeview Middle (middle) — Orange County School District. Always verify school assignments with the district before relying on them.
The brief
Three things that matter here
01Under the WINTER GARDEN 34787 market on paper
$410,000 is 23% below the WINTER GARDEN 34787 median of $530,000, and at $254/sqft it sits under the Winter Garden average of $282.
02Strong assigned schools
William S Maxey Elementary, West Orange High, Lakeview Middle — West Orange High rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $425,000, now $410,000 — a $15K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY · Trevor Zwick. MLS #O6412414.
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. Data is deemed reliable but is not guaranteed accurate by Stellar MLS.
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