5863 CYPRESS HILL ROAD, WINTER GARDEN, FL, 34787
Active40 days on marketListed Jun 24, 2026MLS #TB8522840
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Upcoming open house
Sat, Aug 15
12:00 PM – 2:00 PM
About this home
5863 CYPRESS HILL ROAD
Welcome to Cypress Hill Road, featuring a beautifully maintained townhome located in the highly desirable Horizon West area of Winter Garden. Built in 2018, this move-in-ready residence offers approximately 1,594 square feet of thoughtfully designed living space featuring 2 spacious bedrooms, 2.5 bathrooms, and a rear-entry two-car garage. Step inside to discover an open-concept floor plan that seamlessly blends the living, dining, and kitchen areas, creating the perfect space for both everyday living and entertaining. Pride of ownership is evident throughout, with the home having been exceptionally maintained and cared for. Upstairs, you'll find two generously sized bedroom suites, each designed for comfort and privacy. The spacious secondary bedroom is a standout feature, offering its own private en-suite bathroom and a large walk-in close, making it ideal for guests, roommates, or a growing family. The primary suite provides a relaxing retreat with ample space and storage. Outside, enjoy the low-maintenance lifestyle that townhome living provides while taking advantage of the incredible community amenities nearby. Residents enjoy access to resort-style amenities, including community pools, playgrounds, walking trails, parks, sports courts, and beautifully maintained common areas that make this one of Winter Garden's most sought-after communities. Conveniently located near shopping, dining, entertainment, major roadways, and top-rated schools, this home places you in the heart of everything Horizon West and Winter Garden has to explore. Don't miss your opportunity to own this meticulously maintained townhome in one of Central Florida's most desirable locations. Schedule your private showing today!
Facts & features
The home at a glance
2
Bedrooms
2.5
Bathrooms
1,594
Sqft
0.07 ac
Lot size
2
Garage
2018
Year built
Two
Levels
$235
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 and the real association fee — not generic estimates.
$3,092 /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
$3,092/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
+0.8%
$/sqft vs Winter Garden actives
$235 vs $261
Days on market
40 vs 31 typical
Where $235/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 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 →
WINTER GARDEN 34787 — neighborhood snapshot
Population
93,064
Median age
37.4
Median income
$114,988
Median home value
$475,000
Avg household
3.02
Households w/ children
13,499
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)
163 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 29% 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 5863 CYPRESS HILL ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Feb ’26$419,497
14814 PEEKSKILL DRIVE
3 bd · 2.5 ba · 1,624 sqft · $258/sqft · 4 DOM
Sold · Jun ’26$399,000
14155 ANCILLA BOULEVARD
3 bd · 2.5 ba · 1,629 sqft · $245/sqft · 0 DOM
Sold · May ’26$417,687
14446 WHITTRIDGE DRIVE
3 bd · 2 ba · 1,650 sqft · $253/sqft · 53 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 5863 CYPRESS HILL ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 5863 CYPRESS HILL ROAD — 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
5863 CYPRESS HILL ROAD FAQs
What would the monthly payment be for 5863 CYPRESS HILL ROAD?+
With 3.5% down on a 30-year FHA loan at 6%, the all-in payment lands around $3,092/mo — principal and interest, the actual property-tax bill, the $339/mo association fee 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.
How much are the HOA fees at 5863 CYPRESS HILL ROAD?+
The association fee works out to $339 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 5863 CYPRESS HILL ROAD?+
The most recent tax bill on record (2025) was $2,633. A new owner's bill can differ once the sale price resets the assessed value — we can walk you through what to expect.
Are pets allowed at 5863 CYPRESS HILL ROAD?+
The listing reports pets: Yes. Communities often layer on breed or weight rules — we'll verify the specifics with the association before you commit.
How does the price compare to other homes in Winter Garden?+
At $375,000, this home is listed about 36% 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 5863 CYPRESS HILL ROAD?+
Sunridge Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — 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
$375,000 is 29% below the WINTER GARDEN 34787 median of $529,995, and at $235/sqft it sits under the Winter Garden average of $282.
02Strong assigned schools
Sunridge Elementary, Sunridge Middle, West Orange High — Sunridge Middle rates 4 of 5. Always verify assignments with the district.
03The price has already moved
Listed at $390,000, now $375,000 — a $15K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of ZENITH REALTY FIRM LLC · Brianna Gordon. MLS #TB8522840.
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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