Positioned in one of Central Florida’s most iconic and sought-after locations, this rare opportunity at 1900 Winter Park Road in Winter Park invites you to create something truly exceptional. Set on a spacious homesite, this property offers the flexibility to renovate, expand, or build your custom dream home from the ground up. Whether you envision a modern architectural masterpiece or a timeless estate, this is your canvas to bring that vision to life. What makes this opportunity even more compelling is the location. Just minutes from the charm and sophistication of Park Avenue, you’ll find yourself surrounded by brick-lined streets, boutique shopping, fine dining, and vibrant cultural experiences. Spend your mornings enjoying coffee at local cafés, your afternoons exploring art galleries, and your evenings dining under the lights of one of Central Florida’s most beloved destinations. Living in Winter Park is more than owning a home—it’s embracing a lifestyle. From the scenic beauty of the Winter Park Chain of Lakes, to the historic elegance of Rollins College, this area blends natural beauty, culture, and community in a way few places can. Residents enjoy: Boat tours and waterfront living along the chain of lakes Weekly farmers markets and local events A thriving arts scene including museums, galleries, and theaters Top-rated dining and boutique retail experiences A true sense of community with timeless charm This is more than just land. This is where vision meets opportunity. This is where your next chapter begins. Build the life you’ve been dreaming of—in the heart of Winter Park
For sale
Price cut: $50.9K (6/16)
$799,000
1900 Winter Park Rd, Winter Park, FL 32789
4beds
1,511sqft
Single Family Residence
Built in 1947
8,705 Square Feet Lot
$778,200 Zestimate®
$529/sqft
$-- HOA
What's special
Spacious homesiteBrick-lined streets
- 57 days |
- 1,347 |
- 41 |
Zillow last checked:
Listing updated:
Listed by:
William Grim, III 407-314-9784,
RE/MAX ASSURED 800-393-8600
Source: Stellar MLS,MLS#: O6402566
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 270 Square Feet
- Dimensions: 18x15
Bedroom 1
- Features: Built-in Closet
- Level: First
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 100 Square Feet
- Dimensions: 10x10
Bedroom 3
- Features: Built-in Closet
- Level: First
- Area: 100 Square Feet
- Dimensions: 10x10
Great room
- Level: First
- Area: 540 Square Feet
- Dimensions: 30x18
Kitchen
- Level: First
- Area: 96 Square Feet
- Dimensions: 12x8
Living room
- Level: First
- Area: 360 Square Feet
- Dimensions: 20x18
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Convection Oven, Dishwasher, Microwave, Refrigerator
- Laundry: Inside
Features
- Ceiling Fan(s), Crown Molding, Walk-In Closet(s)
- Flooring: Ceramic Tile, Hardwood
- Windows: Window Treatments
- Has fireplace: Yes
- Fireplace features: Living Room, Wood Burning
- Common walls with other units/homes: Corner Unit
Interior area
- Total structure area: 2,100
- Total interior livable area: 1,511 sqft
Video & virtual tour
Property
Parking
- Total spaces: 1
- Parking features: Garage - Attached
- Attached garage spaces: 1
- Details: Garage Dimensions: 11x11
Features
- Levels: One
- Stories: 1
- Exterior features: Irrigation System
Lot
- Size: 8,705 Square Feet
Details
- Parcel number: 072230125209010
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block
- Foundation: Block
- Roof: Shingle
Condition
- New construction: No
- Year built: 1947
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: CHARMONT
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $529/sqft
- Tax assessed value: $613,683
- Annual tax amount: $2,803
- Date on market: 4/27/2026
- Cumulative days on market: 55 days
- Listing terms: Cash,Conventional,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Road surface type: Brick
Estimated market value
$778,200
$739,000 - $817,000
$3,006/mo
Price history
| Date | Event | Price |
|---|---|---|
| 6/16/2026 | Price change | $799,000-6%$529/sqft |
Source:  Stellar MLS #O6402566 Report a problem | ||
| 5/15/2026 | Price change | $849,900-9.7%$562/sqft |
Source: Stellar MLS #O6402566 Report a problem | ||
| 5/14/2026 | Listed for sale | $941,000$623/sqft |
Source: Stellar MLS #O6402566 Report a problem | ||
| 5/11/2026 | Pending sale | $941,000$623/sqft |
Source: Stellar MLS #O6402566 Report a problem | ||
| 4/28/2026 | Listed for sale | $941,000+109.1%$623/sqft |
Source: Stellar MLS #O6402566 Report a problem | ||
| 6/1/2016 | Listing removed | $450,000$298/sqft |
Source: RE/MAX 200 REALTY #O5369516 Report a problem | ||
| 5/28/2015 | Listed for sale | $450,000+328.9%$298/sqft |
Source: RE/MAX 200 REALTY #O5369516 Report a problem | ||
| 3/7/2001 | Sold | $104,928$69/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $2,698 +4.7% | $202,869 +3% |
| 2023 | $2,576 +9.9% | $196,960 +3% |
| 2022 | $2,344 +1.5% | $191,223 +3% |
| 2021 | $2,308 +0.1% | $185,653 +1.4% |
| 2020 | $2,306 +1.1% | $183,090 +2.3% |
| 2019 | $2,282 +0.9% | $178,974 +1.9% |
| 2018 | $2,263 | $175,637 -28.9% |
| 2017 | $2,263 +1.3% | $246,862 +0.3% |
| 2016 | $2,235 +2.2% | $246,087 +7.5% |
| 2015 | $2,186 -3.1% | $228,931 +11.7% |
| 2014 | $2,255 +2.6% | $204,931 +25.3% |
| 2013 | $2,199 -7% | $163,534 -6.6% |
| 2012 | $2,364 +3.5% | $175,082 -0.3% |
| 2011 | $2,284 +5.7% | $175,671 -8.9% |
| 2010 | $2,162 | $192,859 -29% |
| 2009 | -- | $271,518 -12.5% |
| 2008 | $1,979 -6.6% | $310,455 -6.3% |
| 2007 | $2,120 -6.3% | $331,176 +5.1% |
| 2006 | $2,261 +0.3% | $315,241 +40.1% |
| 2005 | $2,254 +4.9% | $224,933 +32% |
| 2004 | $2,149 +5.8% | $170,348 +4.8% |
| 2003 | $2,031 +3% | $162,471 +18.8% |
| 2002 | $1,972 +35.6% | $136,790 +5.2% |
| 2001 | $1,454 +8% | $130,067 +19.8% |
| 2000 | $1,347 | $108,590 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 32789
Nearby schools
GreatSchools rating
- 10/10AUDUBON PARK SCHOOLGrades: PK-8Distance: 0.9 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 1.4 mi
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Winter Park
- 32789
- 1900 Winter Park Rd
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