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$1,725,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,243 Sq. Ft.
  • Updated 1 day ago
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Welcome to 121 West Maple Street...a Downtown Winter Garden one-of-a-kind statement home spanning nearly 5,500 square feet of indoor & outdoor living space. Originally constructed in 1999 and thoughtfully expanded in 2019...yet this special residence has the heart & soul of a time long ago when character, craftsmanship and attention to details mattered. Private Pool & Spa. Poolhouse. Drawing Room & Study. Courtyard with Fountain. Renovated Kitchen & Bathrooms. 10' Ceilings. Wood Floors. Handmade (USA) Solid Wood Doors. Custom Wood Trim Throughout. Three-Car Garage with Carriage House. Three Fireplaces. Natural Gas. Custom Built Wood Fence with Copper Caps. Located on one of the few remaining brick roads just TWO BLOCKS from Plant Street, this home with spectacular curb appeal is situated on a rare corner double lot with extensive landscaping & beautiful mature trees...including the incredible Southern Live Oak in front that is part of the Winter Garden Heritage Trees project & walking tour. Enjoy historical charm appropriate for the location...yet live without the pains & aches of owning an old historic home. The incredible drawing room & study (2019) was designed by the historical architect for the City of Charleston...twenty-nine windows, extensive trim work & built-ins, historically accurate sconces & lighting and automatic privacy shades. Live the Florida lifestyle outdoors in this incredible outdoor oasis with heated pebble tec saltwater pool & spa. Following a 2023 transformation with a cost of $225,000, the outdoor living space now features a custom poolhouse cabana with a gas fireplace, multiple seating areas, outdoor kitchen with island, built-in grill, burner and refrigerator, retractable screen to astroturf lawn, Trex decking, custom lighting, water features, extended covered lanai and SunBrite outdoor television. (Hayward Natural Gas Pool/Spa Heater - 2025; Hayward Tristar Pool Pump - 2023; Filter Unit - 2020; Salt Cell - 2020). Fantastic & FLEXIBLE floor plan...four bedrooms, three full bathrooms and one half bathroom. Primary suite on main floor. The carriage house above the garage features a separate staircase entrance with private bedroom, bathroom and walk-in closet with built-ins. Stunning kitchen renovation (2021) including custom cabinetry, backsplash, quartz countertops, farm sink, designer lighting, new appliances and an open-concept design that flows effortlessly into the family room. Roof -- July 2019. HVAC -- 2025 (upstairs); 2018 (downstairs - damper system). Tankless Gas Water Heater -- Dec 2015. Garage Epoxy Floor. Whole Home Natural Gas Generator. FULL UPGRADE & SPECIAL FEATURES LIST AVAILABLE. Furnishings and decor (inside & outside), golf cart & custom holiday decorations NEGOTIABLE. Zoned R-2. NO HOA...live without rules & restrictions. You COULD NOT be closer to enjoying the lifestyle of Central Florida's most desirable and growing historic downtown...GOLF CART LIFE, the West Orange Trail, HUGE weekly farmer's market, incredible annual festivals, shopping, dining, art gallery, the Crooked Can Brewery & Plant Street Market, parks & recreation...come JOIN THE FUN! Also conveniently located minutes from the Winter Garden Village shopping center and just minutes from HWY 429 with direct connect to the Turnpike and 408 for an easy commute to anywhere in Central Florida. This is THE ONE you have been waiting for in Downtown Winter Garden...DO NOT MISS your opportunity to own this one-of-a-kind dream home & property!

Full Property Details for 121 W Maple St

General

  • Price: $1,725,000
  • Taxes: $10,571 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6417649
  • Updated: 6/17/2026
  • Added to Site: 2 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 9
  • Interior Features: Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Wet Bar, Window Treatments
  • Fireplace: Yes
  • Fireplace(s): Family Room, Gas, Other Room, Outside
  • Appliances: Bar Fridge, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
  • Furnishings: Furnished
  • Flooring: Brick/Stone, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Child Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
  • Spa: Yes
  • Spa Description: Heated, In Ground
  • Security/Safety: Security System

Exterior

  • Exterior Features: French Doors, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
  • Deck/Patio: Covered, Front Porch, Rear Porch, Screened
  • Porch/Patio/Deck: Covered, Front Porch, Rear Porch, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3
  • Parking Features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, RV Parking, Workshop in Garage

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: G T SMITH SUB 2
  • Driving Directions: In Downtown Winter Garden...corner of West Maple Street & South Highland Avenue.
  • Direction Faces: South

Community

  • Community Name: 34787 - Winter Garden/Oakland

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected

Structural Information

  • Architectural Info: Colonial, Craftsman, Historical, Traditional
  • Architectural Style: Colonial, Craftsman, Historical, Traditional
  • Exterior Const.: Block, HardiPlank Type, Stucco, Wood Frame
  • Roof: Shingle
  • Windows: Blinds, Double Pane Windows, Drapes, Rods, Shades, Shutters, Window Treatments
  • Stories/Levels: Two
  • Square Feet: 3,243
  • Sq. Ft. Source: Appraiser
  • Year Built: 1999

Additional Structures

  • Other Structures: Cabana, Gazebo, Guest House

Lot Features

  • Lot Size (Acres): 0.3
  • Lot Size (Sq. Ft.): 12,852
  • Lot Size: 12852
  • Frontage: Street Brick
  • Street/Road Desc.: Brick
  • Fencing (Description): Wood

Financial Considerations

  • Tax Amount: $10,571.88
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: G T SMITH SUB NO 2 K/103 LOTS 11 & 14 (LESS E 28 FT THEREOF)
  • Flood Zone Info: X
  • APN: 232227810000110
  • Property ID: 232227810000110

Listed by Tara Moore Real Estate

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Listing agent

— 121 W Maple St —

  • Tara Moore Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 121 W Maple St

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.7 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 121 W Maple St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/17/2026
Listed
$1,725,000
563.72%
MLS
10/08/2010
Sold
$259,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 121 W Maple St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,572
5%
$707,962
6%
2024
$10,051
9%
$669,922
8%
2023
$9,219
115%
$619,395
104%
2021
$4,289
-52%
$303,318
-50%
2022
$8,966
109%
$601,354
101%
2021
$4,289
27%
$299,130
24%
2019
$3,371
1%
$241,676
2%
2018
$3,339
3%
$237,170
2%
2017
$3,250
—
$232,292
2%
2016
$3,241
1%
$227,514
3%
2015
$3,211
-1%
$220,967
1%
2014
$3,232
2%
$219,213
2%
2013
$3,155
—
$215,973
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Tara Moore Real Estate

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121 W Maple Street, Winter Garden, FL 34787 (MLS# O6417649) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 121 W Maple Street is currently listed for $1,725,000 and was received on June 17, 2026. Want to learn more about 121 W Maple Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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