755 Woodside Road, FL

$999,999

755 Woodside Road

Maitland, FL 32751

Active
3
Beds
3
Baths
3,049
Sq Ft
0.31
Acres
1974
Built
Private poolFireplace$328/sqft
Single Family Residence

Property type

1974

Year built

13,173 sqft

Lot size

$328

Price / sq ft

$8/mo

HOA dues

17

Days on market

2

Garage spaces

X

Flood zone

About this home

This is the one you've been waiting for- a SLEEK MODERN HOME, where EVERY MAJOR SYSTEM AND FINISH has been REPLACED, REFRESHED and ELEVATED to perfection and minutes from Winter Park without the WP price tag! 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. UTITLITIES $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!

Estimated monthly payment

Principal & interest$5,057
Property taxes$542
Home insurance (est.)$458
HOA dues$8

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history17 days on market

  1. Status: Active
    Apr 29, 2026
  2. Listed$999,999
    Apr 29, 2026
  3. Price increased$999,999

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
17
Subdivision
Forest Brook 5th Sec
County
Seminole
Year built
1974
Living area
3,049 sq ft
Price/sq ft
$328
Building area
3,451 sq ft (Public Records)
Lot size
13,173 sq ft
Lot category
1/4 to less than 1/2
Flood zone
X (12117C0165F)
Garage
2 spaces
Pool
Private pool
Annual taxes
$6,508 (2024)
Parcel #
28-21-30-508-0000-4250
Zoning
R-1A
MLS #
O6402797

Interior Details

Bedrooms
3
Full bathrooms
3
Flooring
Marble
Appliances
Dishwasher, Disposal, Electric Water Heater, Microwave, Range, Refrigerator
Interior features
Built-in Features, Ceiling Fans(s), Dry Bar, Eat-in Kitchen, High Ceilings, Open Floorplan, Solid Surface Counters, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry
Electric Dryer Hookup, Inside, Laundry Room
Stories / Levels
One
Direction faces
Southeast
Fireplace
Yes

Heating & Cooling

Heating
Electric
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
No

HOA & Financial

HOA fee
$100 / Annually
Monthly HOA
$8/mo
Total monthly fees
$8/mo
Total annual fees
$100
CDD
No
Homestead exemption
Yes
Min lease term
No Minimum
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Information is deemed correct but not guaranteed. Buyer and Buyer's Agent to verify any restrictions with the county/city.

Exterior & Construction

Exterior features
Lighting, Sidewalk
Construction materials
Block, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Road surface
Concrete

Utilities

Sewer
Public Sewer
Water source
Public, Well
Utilities
Cable Available, Electricity Connected, Sewer Connected, Water Connected

Community

Pets allowed
Yes

Room Details

RoomLevelDimensions
Living RoomFirst21x22
Dining RoomFirst17x13
Florida RoomFirst13x16
KitchenFirst13x15
Primary BedroomFirst23x16
Primary BathroomFirst13x8
Bedroom 2First11x12
Bedroom 3First11x10
Bathroom 2First10x5
Bathroom 3First12x10

Listing Details

Listing date
2026-04-29
On market date
2026-04-29
Original list price
$999,999
Occupant type
Owner
MLS area
32751 - Maitland / Eatonville
Listing AOR
Orlando Regional
Status changed
2026-04-29
Tax legal description
LOT 425 FOREST BROOK SEC 5 PB 17 PG 26

Flood risk

Minimal riskFEMA Zone XPanel 12117C0165F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

I-4 East, take Exit 90AB- SR 414, Merge onto 414 E/Maitland Blvd, Follow US Hghwy 17/92 to FL-436, Continue on 436 E, Turn Right onto Lake Howell Rd, Right on Derbyshire Rd, Left on Woodside.

More homes like this

MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

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.

Based on information submitted to the MLS GRID as of May 16, 2026 at 10:46 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA