Under contract-accepting backup offers. Discover the perfect canvas for your dream home at 1960 Winter Park Road! With utilities and sewer connected, plus a complete roof replacement in 2019, newer gutters with gutter guards added in 2020, and various new appliances and thoughtful upgrades since, this ¼-acre lot presents the ideal opportunity to either build new, or remodel. Zoned for the highly esteemed Audubon K-8 School, this property offers an ideal location nestled in one of the most coveted pockets of Winter Park. Stroll down the brick-lined street and land at East End market, Kelly’s Homemade Ice Cream, and all the shops and restaurants along the vibrant Corrine Drive corridor; walk around the corner to Blue Jacket Park; or venture North just 2.5 miles to discover the cultural delights of Park Avenue in downtown Winter Park. The existing 1940's home is still bursting with charm and potential. From the moment you arrive, the circular paver driveway and inviting front porch set the tone for a home that balances warmth and functionality. The main residence offers 2 bedrooms and 2 bathrooms across 1,500+ square feet, complemented by a detached 1-bedroom, 1-bath guest cottage. Ideal for extended stays, a private office, hobby space, or flexible living arrangements, the detached cottage presents endless possibilities, with enough space available for creative modifications to suit your needs. A paver 2-car parking pad off the circular drive allows room for temporary or long-term guests, with the added convenience of private entry to the detached dwelling via a paved walkway through the side gate. The main home is well-laid-out, with multiple living & dining spaces to make everyday living and entertaining a breeze, all anchored by hardwood flooring throughout. A spacious, paver side patio and large rear deck offer separate, gated outdoor living areas for versatility and enjoyment, while the rear deck overlooks a private, fenced-in backyard just waiting to be transformed into the perfect Florida oasis. If you are looking to land just a few minutes from downtown Orlando and downtown Winter Park, with easy Access to I-4…this is the location for you!
Pending
$899,000
1960 Winter Park Rd, Winter Park, FL 32789
3beds
1,864sqft
Single Family Residence
Built in 1948
10,258 Square Feet Lot
$883,500 Zestimate®
$482/sqft
$-- HOA
What's special
Large rear deckInviting front porchHardwood flooring throughoutSpacious paver side patioCircular paver driveway
- 49 days |
- 126 |
- 0 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
MaryStuart Day 407-620-8683,
FANNIE HILLMAN & ASSOCIATES 407-644-1234
Source: Stellar MLS,MLS#: O6406091
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Rooms
- Room types: Family Room, Living Room, Utility Room
Primary bedroom
- Description: Room5
- Features: Built-in Closet
- Level: First
- Area: 150 Square Feet
- Dimensions: 12x12.5
Bedroom 2
- Description: Room7
- Features: Built-in Closet
- Level: First
- Area: 144 Square Feet
- Dimensions: 12x12
Primary bathroom
- Description: Room6
- Features: Walk-In Closet(s)
- Level: First
- Area: 99 Square Feet
- Dimensions: 11x9
Bathroom 2
- Description: Room8
- Level: First
- Area: 40 Square Feet
- Dimensions: 8x5
Balcony porch lanai
- Description: Room10
- Level: First
- Area: 297.5 Square Feet
- Dimensions: 17.5x17
Dining room
- Description: Room3
- Level: First
- Area: 170.5 Square Feet
- Dimensions: 15.5x11
Family room
- Description: Room4
- Level: First
- Area: 263.25 Square Feet
- Dimensions: 13.5x19.5
Kitchen
- Description: Room2
- Level: First
- Area: 175 Square Feet
- Dimensions: 14x12.5
Living room
- Description: Room1
- Level: First
- Area: 195 Square Feet
- Dimensions: 19.5x10
Other
- Description: Room9
- Features: Walk-In Closet(s)
- Level: First
- Area: 207 Square Feet
- Dimensions: 11.5x18
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater, Washer
- Laundry: Inside
Features
- Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Living Room/Dining Room Combo, Primary Bedroom Main Floor, Solid Wood Cabinets, Stone Counters, Walk-In Closet(s)
- Flooring: Ceramic Tile, Hardwood
- Doors: French Doors
- Windows: Blinds, Skylight(s), Window Treatments
- Has fireplace: No
Interior area
- Total structure area: 1,913
- Total interior livable area: 1,864 sqft
Property
Parking
- Parking features: Circular Driveway, Parking Pad
- Has uncovered spaces: Yes
Features
- Levels: One
- Stories: 1
- Patio & porch: Deck, Patio, Side Porch
- Exterior features: Rain Gutters, Sidewalk
- Fencing: Fenced,Vinyl,Wood
Lot
- Size: 10,258 Square Feet
- Dimensions: 123 x 83
- Features: City Lot, Sidewalk
- Residential vegetation: Mature Landscaping
Details
- Additional structures: Guest House, Shed(s)
- Parcel number: 072230125209160
- Zoning: R-1AA
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Metal Siding, Wood Frame
- Foundation: Crawlspace, Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1948
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: BB/HS Internet Available, Cable Available, Electricity Connected, Public, Sewer Connected, Street Lights, Water Connected
Community & HOA
Community
- Features: Sidewalks
- Security: Security System, Smoke Detector(s)
- Pet fee: $0 monthly
- Subdivision: CHARMONT
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $482/sqft
- Tax assessed value: $627,605
- Annual tax amount: $7,103
- Date on market: 5/7/2026
- Cumulative days on market: 50 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick
Estimated market value
$883,500
$839,000 - $928,000
$4,014/mo
Price history
| Date | Event | Price |
|---|---|---|
| 5/20/2026 | Pending sale | $899,000$482/sqft |
Source:  Stellar MLS #O6406091 Report a problem | ||
| 5/8/2026 | Listed for sale | $899,000+85.4%$482/sqft |
Source: Stellar MLS #O6406091 Report a problem | ||
| 6/27/2018 | Sold | $485,000-2.8%$260/sqft |
Source: Public Record Report a problem | ||
| 5/4/2018 | Listed for sale | $499,000+126.8%$268/sqft |
Source: FANNIE HILLMAN & ASSOCIATES #O5705571 Report a problem | ||
| 4/5/2012 | Sold | $220,000+48.6%$118/sqft |
Source: Stellar MLS #O5085511 Report a problem | ||
| 10/18/1995 | Sold | $148,000$79/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $6,879 +3.9% | $471,429 +3% |
| 2023 | $6,623 +5.9% | $457,698 +3% |
| 2022 | $6,255 +1.1% | $444,367 +3% |
| 2021 | $6,184 -0.8% | $431,424 +0.8% |
| 2020 | $6,232 -1% | $427,832 +0.6% |
| 2019 | $6,298 +126.2% | $425,105 +105.2% |
| 2018 | $2,784 | $207,129 -27.8% |
| 2017 | $2,784 +1.2% | $286,822 -0.5% |
| 2016 | $2,752 +2.2% | $288,214 +3.2% |
| 2015 | $2,693 -3.1% | $279,378 +18.1% |
| 2014 | $2,779 +2.4% | $236,540 +22.7% |
| 2013 | $2,713 -20.7% | $192,856 -0.4% |
| 2012 | $3,421 -1.9% | $193,693 -1.5% |
| 2011 | $3,487 -6.3% | $196,690 -9.2% |
| 2010 | $3,722 | $216,643 -24.6% |
| 2009 | -- | $287,374 -13% |
| 2008 | $5,415 -5.9% | $330,430 -6.5% |
| 2007 | $5,752 -4.5% | $353,318 +4.9% |
| 2006 | $6,025 +35.2% | $336,856 +39.6% |
| 2005 | $4,458 +31.5% | $241,253 +29.9% |
| 2004 | $3,391 +4.1% | $185,743 +0.7% |
| 2003 | $3,256 +17.5% | $184,523 +17.4% |
| 2002 | $2,771 +2.3% | $157,119 +3.7% |
| 2001 | $2,708 +44.9% | $151,514 +17.8% |
| 2000 | $1,869 | $128,659 |
Find assessor info on the county website
Monthly payment
Est. payment$--/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
Schools provided by the listing agent
- Middle: Audubon Park K-8
- High: Winter Park High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Florida
- Orange County
- Winter Park
- 32789
- 1960 Winter Park Rd
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