**MULTIPLE OFFERS RECEIVED** 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.
Pending
$1,725,000
121 W Maple St, Winter Garden, FL 34787
4beds
3,243sqft
Single Family Residence
Built in 1999
0.3 Acres Lot
$1,688,600 Zestimate®
$532/sqft
$-- HOA
What's special
Garage epoxy floorThree fireplacesCourtyard with fountainTrex deckingSunbrite outdoor televisionPrivate pool and spaTwenty-nine windows
- 17 days |
- 2,173 |
- 206 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
Tara Moore 407-765-3700,
TARA MOORE REAL ESTATE 407-738-5588
Source: Stellar MLS,MLS#: O6417649
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Rooms
- Room types: Den/Library/Office, Family Room, Dining Room, Living Room, Garage Apartment, Great Room, Utility Room, Storage Rooms
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 224 Square Feet
- Dimensions: 14x16
Bedroom 2
- Features: Built-in Closet
- Level: Second
- Area: 192 Square Feet
- Dimensions: 12x16
Bedroom 3
- Features: Built-in Closet
- Level: Second
- Area: 156 Square Feet
- Dimensions: 12x13
Bedroom 4
- Features: Walk-In Closet(s)
- Level: Second
- Area: 408 Square Feet
- Dimensions: 17x24
Den
- Level: First
- Area: 240 Square Feet
- Dimensions: 12x20
Dining room
- Level: First
- Area: 195 Square Feet
- Dimensions: 13x15
Family room
- Level: First
- Area: 320 Square Feet
- Dimensions: 16x20
Kitchen
- Level: First
- Area: 132 Square Feet
- Dimensions: 11x12
Living room
- Level: First
- Area: 400 Square Feet
- Dimensions: 20x20
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Dishwasher, Disposal, Dryer, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
- Laundry: Electric Dryer Hookup, Gas Dryer Hookup, Laundry Room
Features
- Built-in Features, Ceiling Fan(s), Coffered Ceiling(s), Crown Molding, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Tray Ceiling(s), Walk-In Closet(s), Wet Bar
- Flooring: Brick/Stone, Hardwood
- Doors: French Doors, Outdoor Grill, Outdoor Kitchen
- Windows: Blinds, Window Treatments
- Has fireplace: Yes
- Fireplace features: Family Room, Gas, Other Room, Outside
- Furnished: Yes
Interior area
- Total structure area: 5,489
- Total interior livable area: 3,243 sqft
Video & virtual tour
Property
Parking
- Total spaces: 3
- Parking features: Driveway, Garage Door Opener, Garage Faces Side, Golf Cart Parking, Oversized, RV Access/Parking, Workshop in Garage
- Attached garage spaces: 3
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 29x32
Features
- Levels: Two
- Stories: 2
- Patio & porch: Covered, Front Porch, Rear Porch, Screened
- Exterior features: Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Mailbox, Private Yard, Rain Gutters, Sidewalk
- Has private pool: Yes
- Pool features: Child Safety Fence, Heated, In Ground, Lighting, Salt Water, Screen Enclosure
- Has spa: Yes
- Spa features: Heated, In Ground
- Fencing: Wood
Lot
- Size: 0.3 Acres
- Features: Corner Lot, City Lot, Landscaped, Oversized Lot, Sidewalk
- Residential vegetation: Mature Landscaping, Oak Trees, Trees/Landscaped
Details
- Additional structures: Cabana, Gazebo, Guest House
- Parcel number: 232227810000110
- Zoning: R-2
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Craftsman,Historical,Traditional
- Property subtype: Single Family Residence
Materials
- Block, HardiPlank Type, Stucco, Wood Frame
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1999
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Natural Gas Connected, Street Lights, Water Connected
Community & HOA
Community
- Security: Security System
- Pet fee: $0 monthly
- Subdivision: G T SMITH SUB 2
HOA
- Has HOA: No
Location
- Region: Winter Garden
Financial & listing details
- Price per square foot: $532/sqft
- Tax assessed value: $896,854
- Annual tax amount: $10,571
- Date on market: 6/17/2026
- Cumulative days on market: 16 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick
Estimated market value
$1,688,600
$1.60M - $1.77M
$4,698/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/24/2026 | Pending sale | $1,725,000$532/sqft |
Source:  Stellar MLS #O6417649 Report a problem | ||
| 6/17/2026 | Listed for sale | $1,725,000+122.6%$532/sqft |
Source: Stellar MLS #O6417649 Report a problem | ||
| 5/4/2021 | Sold | $775,000+198.2%$239/sqft |
Source: Public Record Report a problem | ||
| 10/13/2010 | Sold | $259,900+1006%$80/sqft |
Source: Public Record Report a problem | ||
| 8/2/1997 | Sold | $23,500$7/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $10,051 +9% | $669,922 +8.2% |
| 2023 | $9,219 +2.8% | $619,395 +3% |
| 2022 | $8,966 +109.1% | $601,354 +98.3% |
| 2021 | $4,289 +0.8% | $303,318 +1.4% |
| 2020 | $4,256 +26.3% | $299,130 +23.8% |
| 2019 | $3,371 +1% | $241,676 +1.9% |
| 2018 | $3,339 | $237,170 -27.2% |
| 2017 | $3,339 +2.8% | $325,715 +16.1% |
| 2016 | $3,250 +0.3% | $280,478 +9.9% |
| 2015 | $3,241 +0.3% | $255,328 +10.9% |
| 2014 | $3,232 +2.4% | $230,243 +6.6% |
| 2013 | $3,155 +0.7% | $215,973 +1.2% |
| 2012 | $3,134 -3.3% | $213,501 -2.4% |
| 2011 | $3,240 +8% | $218,737 -5.9% |
| 2010 | $2,999 | $232,480 -16% |
| 2009 | -- | $276,638 -15.6% |
| 2008 | $2,630 -4.2% | $327,648 -9.2% |
| 2007 | $2,746 -7.7% | $360,887 +26.4% |
| 2006 | $2,975 +0.7% | $285,521 +19% |
| 2005 | $2,955 +4.7% | $240,027 +19% |
| 2004 | $2,821 +14.9% | $201,674 +15.7% |
| 2003 | $2,456 +2.9% | $174,233 +5% |
| 2002 | $2,386 -1.1% | $165,944 +8.2% |
| 2001 | $2,413 -15.9% | $153,336 +1.3% |
| 2000 | $2,870 | $151,382 |
Find assessor info on the county website
Monthly payment
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Payment breakdown
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Climate risks
Neighborhood: 34787
Nearby schools
GreatSchools rating
- 5/10Dillard Street Elementary SchoolGrades: PK-5Distance: 0.7 mi
- 4/10Lakeview Middle SchoolGrades: 6-9Distance: 0.9 mi
- 7/10West Orange High SchoolGrades: 9-12Distance: 1.7 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Winter Garden
- 34787
- 121 W Maple St
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