755 WOODSIDE ROAD, MAITLAND, FL, 32751
Active95 days on marketListed Apr 29, 2026MLS #O6402797
About this home
755 WOODSIDE ROAD
NEWLY PRICED TO SELL, UNDER APPRAISED VALUE, DO NOT MISS THIS OPPORTUNITY!! SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and just minutes from Winter Park. Located at 755 Woodside Road in the community of Forest Brook in Maitland with 3,054 Sq Ft. of living space, in a quiet CUL-DE- SAC, this 3 BEDROOM 3 FULL BATHROOM POOL home with 2 Car garage on a .31 ACRE LOT is effortless Florida living.**SOLAR PANELS-(Avg. utilities $40/MONTH) From the moment you arrive you will be impressed with the mature, manicured landscaping and architectural features that sets the tone for the quality you will find inside. The EXPANSIVE OPEN FLOOR PLAN draws you in with an effortless flow between living, dining, and entertaining spaces. SLEEK MODERN CABINETRY, MARBLE FLOORING and DESIGNER FIXTURES elevate every room. The chef-inspired kitchen features a LARGE CENTER ISLAND perfect for casual dining, meal prep or gathering with guests. A stylish PASS THROUG BAR connects seamlessly to the Florida Room making entertaining a breeze. The OVERSIZED PRIMARY SUITE is a true retreat with MARBLE FLOORING, an abundance of natural light and CUSTOM SLIDING GLASS DOORS leading to the expansive pool deck. The en-suite bathroom features FLOATING VANITIES, MARBLE FLOORING and a SEAMLESS GLASS ENCLOSED SHOWER and STAND ALONE TUB that continues the modern aesthetic that feels like a five star hotel everyday. Laundry with sink and overhead cabinets is centrally located near the kitchen and primary suite. The focal point of the family room is the stunning MARBLE FACED FIREPLACE. Two generously sized secondary bedrooms are located off the family room, sharing a beautiful bathroom featuring marble floors, floating dual sink vanity and walk-in shower-consistent with the finishes throughout. The Florida Room is where the fun truly begins. Currently set up as the ultimate entertainment space, this incredible space offers endless possibilities- playroom, game room, movie room or the perfect indoor/outdoor lounge for hosting family and friends.NEW OVERSIZED WINDOWS frame spectacular views of the pool, floods the space with natural light and seamlessly connect the indoors to the out. The THIRD FULL BATH located off the Florida Room serves as the POOL BATH with walk-in shower, Jacuzzi, floating vanity and premium finishes. This homes outdoor spaces provide something for everyone. The large, screened-in pool deck features a Tiki Bar and dedicated PROJECTOR SCREEN AREA (Screen & Tiki Bar CONVEY IN THE SALE) perfect for entertaining pool side.The side yard with artificial turf is clean, low maintenance, and pet friendly. A charming brick paver seating area creates as cozy spot to relax, unwind or let the pets roam freely. Enjoy the tranquility of this homes beautiful backyard. ADDITIONAL LIST OF UPGRADES: 2020 HARDSCAPE & LANDSCAPING, 2021 NEW WATER HEATER & POOL PUMP, 2024/2025 REPLACED LARGE AC AND DUCTWORK, AC PRIMARY SIDE UNIT, 2025 NEW FLORIDA ROOM WINDOWS, ADDED RID-O-RUST SYSTEM TO WELL FOR IRRIGATION, SCREENED IN POOL/DECK, SOLAR PANELS (to be paid off at closing) ADDED DRY BAR WITH UPPER AND LOWER CABINETS IN DINING AREA. Conveniently located minutes away from boutique shopping, acclaimed dining and vibrant entertainment of the beautiful city of Winter Park with easy access to Orlando and surrounding communities. This home won't last long. Call your Agent to schedule a showing today!
Facts & features
The home at a glance
3
Bedrooms
3
Bathrooms
3,049
Sqft
0.31 ac
Lot size
2
Garage
1974
Year built
One
Levels
$303
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.
$6,048 /mo · 10% down Conventional, 30-yr fixed at 6%
The assumptions
Above the FHA loan limit for our service areas, so Conventional is the default. VA buyers: switch below — $0 down.
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
FHA isn’t available at this price — the loan would exceed the $541,287 FHA limit for our service areas.
Estimated payment
$6,048/mo
Includes estimated PMI — it drops off once you reach 20% equity. 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.
$/sqft vs Maitland actives
$303 vs $287
Days on market
95 vs 41 typical
Where $303/sqft sits among the 110 Maitland 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 Maitland
Drive times from this address
Estimated driving times, typical traffic. Data © OpenStreetMap contributors.
Get to know Maitland. See the full Maitland guide →
MAITLAND 32751 — neighborhood snapshot
Population
22,853
Median age
38.7
Median income
$94,277
Median home value
$433,100
Avg household
2.27
Households w/ children
2,397
For the school run
Seminole County School District
School assignments and ratings via edgeAI — always verify with the district.
The numbers that matter
The Maitland market
$526K → $469K
Maitland median sold, yr/yr
96.8%
Sale-to-list ratio (12 mo)
59 of 110
Maitland actives have cut their price
Median sold price, Maitland, trailing 36 months (3-month rolling) · live MLS data.
This home is listed 115% above the MAITLAND 32751 median. See the full Maitland market guide →
Paper trail
This home's history
Reality check
What actually sold near 755 WOODSIDE ROAD
Asking prices are opinions — closed sales are facts. The most comparable homes that actually changed hands nearby in the last twelve months.
Sold · Mar ’26$450,000
736 FOREST GLEN COURT · same community
4 bd · 2 ba · 1,647 sqft · $273/sqft · 168 DOM
Sold · Jun ’26$424,000
775 WOODSIDE ROAD · same community
3 bd · 2 ba · 1,456 sqft · $291/sqft · 9 DOM
Sold · Sep ’25$1,635,000
2402.5 TEMPLE DRIVE
4 bd · 4.5 ba · 3,248 sqft · $503/sqft · 85 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 755 WOODSIDE ROAD — start here.
Your lender
Andrew Acosta
Acosta Home Loans with PRMG · NMLS #1468866
Pre-approval, rates, and the real monthly number for 755 WOODSIDE 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
755 WOODSIDE ROAD FAQs
What would the monthly payment be for 755 WOODSIDE ROAD?+
With 10% down on a 30-year Conventional loan at 6%, the all-in payment lands around $6,048/mo — principal and interest, the actual property-tax bill, the $8/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 755 WOODSIDE ROAD?+
The association fee works out to $8 per month. Ask us for the full association documents — they spell out exactly what the fee covers.
What are the property taxes on 755 WOODSIDE ROAD?+
The most recent tax bill on record (2024) was $6,508. 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 755 WOODSIDE 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 Maitland?+
At $925,000, this home is listed about 64% above the Maitland median of $564,950. The market section on this page shows how the area is trending.
Which schools are assigned to 755 WOODSIDE ROAD?+
Lake Orienta Elementary School (elementary), Milwee Middle School (middle), Lyman High School (high) — Seminole County School District. Always verify school assignments with the district before relying on them.
The brief
Four things that matter here
01Positioned at the premium end
$925,000 runs 115% above the MAITLAND 32751 median — but at 3,049 sqft it's also 64% larger than the typical Maitland listing.
02Your own pool
A private pool — the feature Florida buyers ask for first, already in the ground and included in the price.
03Time on market is leverage
95 days on market against a Maitland median of 41 — sellers in this position are usually ready to negotiate.
04The price has already moved
Listed at $999,999, now $925,000 — a $75K cut. The full history is in the market section below.
Keep looking
Similar homes nearby
Listing courtesy of EMPIRE NETWORK REALTY · Diane Heiken. MLS #O6402797.
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.
Never miss a listing
New Maitland homes, in your inbox
Like 755 WOODSIDE ROAD but not quite? A daily digest of every new listing in Maitland — straight from the MLS, hours after it goes live. Unsubscribe anytime.
Just watching this one home? Ask David to ping you on any price or status change →