Under contract-accepting backup offers. Nestled in the highly coveted Courtlea Oaks community, within Winter Garden’s sought-after golf cart district, this beautifully updated home offers the perfect blend of timeless charm and modern luxury. Enjoy the lifestyle that has made historic downtown Winter Garden one of Central Florida’s most beloved destinations—just minutes away you’ll find award-winning restaurants, boutique shopping, the renowned Saturday Farmers Market, live entertainment, festivals, and miles of the West Orange Trail. Situated on an oversized .33-acre homesite, this exceptional residence offers 2,765 square feet with three bedrooms, two-and-a-half baths, and thoughtfully designed living spaces filled with architectural character. From the moment you enter, you’ll be welcomed by soaring ceilings, rich hardwood flooring, custom board-and-batten millwork, crown molding, and a stunning two-story foyer that creates an unforgettable first impression. At the heart of the home is a beautifully renovated kitchen featuring custom white cabinetry, a center island, farmhouse sink, professional-style gas range with pot filler, stainless steel appliances, and generous workspace—perfectly designed for both everyday living and effortless entertaining. The kitchen flows seamlessly into the spacious family room and sun-filled dining area overlooking the backyard oasis. Upstairs, the expansive loft provides exceptional flexibility as a media room, home office, fitness space, or could easily accommodate a fourth bedroom. The secondary bedrooms are generously sized, including one with a charming custom-built window desk. The beautifully updated bathrooms continue the home’s timeless design with quality finishes throughout. Step outside to your own private retreat featuring a sparkling pool, expansive brick paver deck, lush landscaping, and plenty of room for entertaining or simply relaxing under the Florida sun. Homes in Courtlea Oaks are rarely available. Combining an exceptional location, beautiful updates, timeless architecture, and one of Winter Garden’s most desirable lifestyles, this is a home you’ll be proud to call your own.
Accepting backups
Price cut: $11K (8/29)
$939,000
434 VALLEY VIEW DRIVE, WINTER GARDEN, FL 34787
3beds
2,765sqft
Single Family Residence
Built in 2000
0.33 Acres Lot
$-- Zestimate®
$340/sqft
$83/mo HOA
What's special
Center islandBeautifully renovated kitchenExpansive loftTwo-and-a-half bathsThree bedroomsCustom board-and-batten millworkSparkling pool
- 56 days
- 1,886
- 159
Zillow last checked:
Listing updated:
Listed by:
Jennifer Coon 321-948-8056,
LAKESIDE REALTY WINDERMERE INC 407-876-5575
Source: Stellar MLS,MLS#: O6425087
Originating MLS: Orlando Regional

Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Second
- Area: 280 Square Feet
- Dimensions: 20x14
Kitchen
- Level: First
- Area: 231 Square Feet
- Dimensions: 21x11
Living room
- Level: First
- Area: 434 Square Feet
- Dimensions: 31x14
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
- Laundry: Inside
Features
- Ceiling Fan(s), Crown Molding, Eating Space In Kitchen, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Flooring: Carpet, Tile, Hardwood
- Doors: French Doors
- Windows: Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 3,602
- Total interior livable area: 2,765 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Driveway, Garage Door Opener, Garage Faces Side, Oversized
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Front Porch, Patio, Porch
- Exterior features: Irrigation System, Lighting, Rain Gutters
- Has private pool: Yes
- Pool features: In Ground
Lot
- Size: 0.33 Acres
- Features: Landscaped
- Residential vegetation: Oak Trees, Trees/Landscaped
Details
- Parcel number: 142227194200410
- Zoning: R-1
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Wood Frame, Wood Siding
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Public, Street Lights, Underground Utilities
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: COURTLEA OAKS PH 01A
HOA
- Has HOA: Yes
- HOA fee: $83 monthly
- HOA name: Tracy Durham
- HOA phone: 407-317-5252
Location
- Region: Winter Garden
Financial & listing details
- Price per square foot: $340/sqft
- Tax assessed value: $565,706
- Annual tax amount: $4,087
- Date on market: 7/16/2026
- Cumulative days on market: 48 days
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Asphalt
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 8/29/2026 | Price change | $939,000-1.2%$340/sqft |
Source: | ||
| 7/31/2026 | Listed for sale | $950,000$344/sqft |
Source: | ||
| 7/24/2026 | Contingent | $950,000$344/sqft |
Source: | ||
| 7/16/2026 | Listed for sale | $950,000+216.8%$344/sqft |
Source: | ||
| 8/15/2013 | Listing removed | $299,900$108/sqft |
Source: Christy Clark-Weber #o5015334 Report a problem | ||
| 8/1/2013 | Listed for sale | $299,900$108/sqft |
Source: Christy Clark-Weber #o5015334 Report a problem | ||
| 8/28/2011 | Listing removed | $299,900+9.1%$108/sqft |
Source: Southern Heritage Realty, Inc. #o5007435 Report a problem | ||
| 5/26/2011 | Sold | $275,000-8.3%$99/sqft |
Source: Stellar MLS #O5015334 Report a problem | ||
| 9/30/2010 | Listed for sale | $299,900+33.3%$108/sqft |
Source: Southern Heritage Reatly, Inc. #o5007435 Report a problem | ||
| 9/20/2001 | Sold | $225,000+379.7%$81/sqft |
Source: Public Record Report a problem | ||
| 3/26/1999 | Sold | $46,900+17%$17/sqft |
Source: Public Record Report a problem | ||
| 9/25/1995 | Sold | $40,078$14/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $3,881 +4.2% | $283,163 +3.4% |
| 2023 | $3,723 +3.1% | $273,945 +3% |
| 2022 | $3,610 +1.5% | $265,966 +3% |
| 2021 | $3,555 +0.8% | $258,219 +1.4% |
| 2020 | $3,527 +1% | $254,654 +2.3% |
| 2019 | $3,492 +0.9% | $248,929 +1.9% |
| 2018 | $3,459 | $244,288 -16.5% |
| 2017 | $3,459 +2.7% | $292,707 -4.1% |
| 2016 | $3,367 +0.2% | $305,265 +8.6% |
| 2015 | $3,358 -2.4% | $281,080 +12.8% |
| 2014 | $3,440 +2.4% | $249,205 +9.6% |
| 2013 | $3,359 +0.5% | $227,454 +1% |
| 2012 | $3,344 -18.5% | $225,259 -1.5% |
| 2011 | $4,103 +17.6% | $228,738 -4.5% |
| 2010 | $3,490 | $239,539 -15.2% |
| 2009 | -- | $282,554 -21.2% |
| 2008 | $3,565 -2.4% | $358,365 -7.1% |
| 2007 | $3,652 -7.8% | $385,675 +19.9% |
| 2006 | $3,960 0% | $321,681 +28.6% |
| 2005 | $3,961 +15.2% | $250,156 +12.8% |
| 2004 | $3,438 +0.2% | $221,730 +0.8% |
| 2003 | $3,432 +2.8% | $219,981 +5.8% |
| 2002 | $3,339 | $208,000 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
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Neighborhood: 34787
Nearby schools
Schools provided by the listing agent
- Elementary: Dillard Street Elem
- Middle: Lakeview Middle
- High: West Orange High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.







