1415 SHERBOURNE STREET, WINTER GARDEN, FL, 34787
Active27 days on marketListed Sep 28, 2026MLS #O6445531
About this home
1415 SHERBOURNE STREET
Welcome to this beautifully updated 3-bedroom, 2.5-bath home in the heart of Winter Garden! Ideally located just 5 minutes from Winter Garden Village, 10 minutes to Downtown Winter Garden & Plant Street Market, and walking distance to top-rated Whispering Oak Elementary. The open floor plan features high ceilings and a spacious living area overlooking the remodeled kitchen with a large island, quartz countertops, subway tile backsplash, ample storage, and stainless steel appliances. The adjacent dining area flows into a screened-in patio with extra-high ceilings—perfect for indoor/outdoor living.The fully fenced backyard offers shade and space for outdoor activities. Upstairs, the large owner’s suite features a walk-in closet and a fully remodeled ensuite with double vanities, tiled floors, and a glass-enclosed shower. Two additional bedrooms share an updated bathroom with new tile, vanity, and tub. This move-in ready home has been thoughtfully updated for a turnkey experience. Major upgrades include: * New Water Heater (2026) * New Roof (2019) * New HVAC (2022 & just serviced 9/2026) * New Fence (2022) * New Kitchen Appliances (2022) * Upgraded Bathrooms (2022) * Updated Kitchen (2022) Neighborhood amenities include a brand new playground with sunshades and turf, plus a nearby path leading to open green space with basketball courts, baseball and soccer fields—all en route to Whispering Oak Elementary. Schedule a tour today! *Owners will be adding a washer/dryer for tenant use prior to move in.*
Facts & features
The home at a glance
3
Bedrooms
2.5
Bathrooms
1,369
Sqft
0.1 ac
Lot size
2
Garage
2002
Year built
Two
Levels
$2
Per sqft
Inside
Outside & construction
Community & fees
Utilities & systems
The numbers
What it really costs
Principal and interest plus estimated taxes and insurance. Run your own numbers below.
$182 /mo · 3.5% down FHA, 30-yr fixed at 7.5%
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
$182/mo
Includes FHA mortgage insurance and the financed 1.75% upfront premium. Estimates only — taxes at 1.1%/yr and typical insurance; your lender’s numbers will differ. CENTURY 21 Edge partners with Florida’s best lenders.
Can I afford this home? → See what you can comfortably afford from your income, debts and savings.
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.
$/sqft vs Winter Garden actives
$2 vs $260
Days on market
27 vs 60 typical
Where $2/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 Stone Creek
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Winter Garden. See the full Winter Garden guide →
Stone Creek — neighborhood snapshot
Population
1,146
Median age
36
Median income
$108,399
Median home value
$496,400
Avg household
3
Households w/ children
202
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
$585K → $611K
Winter Garden median sold, yr/yr
97.6%
Sale-to-list ratio (12 mo)
203 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 99% 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 1415 SHERBOURNE STREET
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Oct ’26$915,000
16104 SANDHILL ROAD
3 bd · 2 ba · 1,364 sqft · $671/sqft · 96 DOM
Sold · Oct ’26$521,505
13865 EASDALE ALLEY
4 bd · 3.5 ba · 1,678 sqft · $311/sqft · 0 DOM
Sold · Aug ’26$536,191
17049 HAGGERTY HOLLOW DRIVE
3 bd · 2 ba · 1,772 sqft · $303/sqft · 21 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
Emanuel Marin Maldonado
Real estate agent · CENTURY 21 Edge
Tours, negotiation, and every question about 1415 SHERBOURNE STREET — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 1415 SHERBOURNE STREET — before you fall in love.
See it in person
Schedule a tour
Live availability from Emanuel's calendar — pick a time and it's booked. Confirmation lands in your inbox immediately.
Straight answers
1415 SHERBOURNE STREET FAQs
What would the monthly payment be for 1415 SHERBOURNE STREET?+
With 3.5% down on a 30-year FHA loan at 7.5%, the all-in payment lands around $182/mo — principal and interest, estimated property taxes 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.
Are pets allowed at 1415 SHERBOURNE STREET?+
The listing reports pets: Breed Restrictions, Number Limit, Pet Deposit, Size Limit, 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 $2,650, this home is listed about 100% below the Winter Garden median of $595,000. The market section on this page shows how the area is trending.
Which schools are assigned to 1415 SHERBOURNE STREET?+
Whispering Oak Elementary (elementary), Sunridge Middle (middle), West Orange High (high) — Orange County School District. Always verify school assignments with the district before relying on them.
Keep looking
Similar homes nearby
Listing courtesy of ALL REAL ESTATE & INVESTMENTS · Lindsey Hahn. MLS #O6445531.
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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