BUYER GOT COLD FEET= YOUR OPPORTUNITY! Welcome to 1421 Sunset Drive – A Turnkey Gem in the Heart of Olde Winter Park! This is a rare opportunity to own a beautifully updated home on one of Olde Winter Park’s most charming, brick-lined, tree-canopied streets. Just steps from serene Lake Knowles and Lake Wilbar, and minutes from the vibrant dining, shopping, and cultural experiences of Park Avenue, this 3-bedroom, 3.5-bathroom residence offers the perfect blend of classic charm and modern convenience. Enjoy a low-maintenance lifestyle with eco-friendly landscaping and a thoughtfully designed floor plan featuring two spacious primary suites — one upstairs and one down — each with its own updated bathroom. Inside, the home boasts tall vaulted ceilings, warm wood plank LVT flooring, a cozy wood-burning fireplace, and multiple inviting living areas. The kitchen is a standout with sleek cabinetry, granite countertops, and stainless steel appliances, ideal for both daily living and entertaining. Step outside to enjoy Trex decking on both front and rear patios, a fenced backyard for privacy, and a convenient laundry/mudroom entry from the garage. Additional highlights include a standing seam metal roof, attached garage, and access to top-rated Winter Park schools. The home is also located near the YMCA, Interlachen Country Club, Winter Park Racquet Club, Rollins College, UCF, and AdventHealth Winter Park. This home is move-in ready and offers the very best of Winter Park living — schedule your private showing today!
Sold for $825,000
$825,000
1421 SUNSET DRIVE, WINTER PARK, FL 32789
3beds
1,672sqft
Single Family Residence
Built in 1977
5,477 Square Feet Lot
$820,200 Zestimate®
$493/sqft
$3,588 Estimated rent
Home value
$820,200
$746,000 - $902,000
$3,588/mo
Zestimate® history
Owner options
List your home for rent
$3,588/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$3,588/mo
Rent Zestimate®
Refinance and save
$4,952/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$4,952/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Zillow last checked:
Listing updated:
Listed by:
Sarah Tomlinson 407-721-7823,
COMPASS FLORIDA LLC 407-203-9441
Bought with:
James Gay, 3582257
PREMIUM PROPERTIES R.E SERVICE
Source: Stellar MLS,MLS#: O6330762
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Other
- Features: Walk-In Closet(s)
- Level: First
- Area: 135 Square Feet
- Dimensions: 15x9
Primary bedroom
- Features: Walk-In Closet(s)
- Level: Second
- Area: 154 Square Feet
- Dimensions: 14x11
Bedroom 2
- Features: Walk-In Closet(s)
- Level: Second
- Area: 110 Square Feet
- Dimensions: 11x10
Bonus room
- Features: No Closet
- Level: First
- Area: 154 Square Feet
- Dimensions: 14x11
Dining room
- Level: First
- Area: 100 Square Feet
- Dimensions: 10x10
Kitchen
- Level: First
- Area: 120 Square Feet
- Dimensions: 12x10
Laundry
- Level: First
- Area: 90 Square Feet
- Dimensions: 10x9
Living room
- Level: First
- Area: 150 Square Feet
- Dimensions: 15x10
Heating
- Central
Cooling
- Central Air
Appliances
- Included: Convection Oven, Dishwasher, Dryer, Freezer, Microwave, Refrigerator, Washer, Wine Refrigerator
- Laundry: Inside, Laundry Room
Features
- Solid Surface Counters, Walk-In Closet(s)
- Flooring: Tile, Vinyl
- Doors: Sliding Doors
- Has fireplace: Yes
- Fireplace features: Wood Burning
Interior area
- Total structure area: 1,930
- Total interior livable area: 1,672 sqft
Property
Parking
- Total spaces: 1
- Parking features: Garage - Attached
- Attached garage spaces: 1
Features
- Levels: Two
- Stories: 2
- Exterior features: Lighting, Other, Rain Gutters
Lot
- Size: 5,477 Square Feet
Details
- Parcel number: 322130453607080
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Cement Siding
- Foundation: Slab
- Roof: Metal
Condition
- New construction: No
- Year built: 1977
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Connected, Electricity Connected, Sewer Connected, Street Lights, Water Available
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: LAKE KNOWLES TERRACE
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $493/sqft
- Tax assessed value: $540,314
- Annual tax amount: $8,492
- Date on market: 7/30/2025
- Cumulative days on market: 20 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick
Price history
| Date | Event | Price |
|---|---|---|
| 9/15/2025 | Sold | $825,000-1.2%$493/sqft |
Source:  Stellar MLS #O6330762 Report a problem | ||
| 8/26/2025 | Pending sale | $835,000$499/sqft |
Source: Stellar MLS #O6330762 Report a problem | ||
| 8/14/2025 | Price change | $835,000-1.8%$499/sqft |
Source: Stellar MLS #O6330762 Report a problem | ||
| 8/13/2025 | Listed for sale | $850,000$508/sqft |
Source: Stellar MLS #O6330762 Report a problem | ||
| 8/6/2025 | Pending sale | $850,000$508/sqft |
Source: Stellar MLS #O6330762 Report a problem | ||
| 7/30/2025 | Listed for sale | $850,000+30.8%$508/sqft |
Source: Stellar MLS #O6330762 Report a problem | ||
| 9/21/2022 | Sold | $650,000-6.8%$389/sqft |
Source: Public Record Report a problem | ||
| 8/9/2022 | Pending sale | $697,500$417/sqft |
Source: Stellar MLS #O6043957 Report a problem | ||
| 7/30/2022 | Price change | $697,500-5.1%$417/sqft |
Source: Stellar MLS #O6043957 Report a problem | ||
| 7/18/2022 | Listed for sale | $735,000+56.4%$440/sqft |
Source: Stellar MLS #O6043957 Report a problem | ||
| 4/1/2020 | Sold | $469,900$281/sqft |
Source: Public Record Report a problem | ||
| 2/24/2020 | Pending sale | $469,900$281/sqft |
Source: BAR INVEST REALTY LLC #O5844629 Report a problem | ||
| 2/17/2020 | Listed for sale | $469,900+1.1%$281/sqft |
Source: BAR INVEST REALTY LLC #O5844629 Report a problem | ||
| 9/15/2019 | Listing removed | $3,400$2/sqft |
Source: Keller Williams At The Parks Report a problem | ||
| 9/13/2019 | Listed for rent | $3,400+13.5%$2/sqft |
Source: Keller Williams At The Parks Report a problem | ||
| 3/28/2019 | Listing removed | $465,000$278/sqft |
Source: Keller Williams Winter Park #O5754397 Report a problem | ||
| 3/9/2019 | Price change | $465,000-4.9%$278/sqft |
Source: Keller Williams Winter Park #O5754397 Report a problem | ||
| 2/27/2019 | Price change | $489,000-2.2%$292/sqft |
Source: Keller Williams Winter Park #O5754397 Report a problem | ||
| 2/7/2019 | Price change | $499,995-5.5%$299/sqft |
Source: Keller Williams Winter Park #O5754397 Report a problem | ||
| 1/28/2019 | Listing removed | $2,995$2/sqft |
Source: Keller Williams Winter Park #O5759033 Report a problem | ||
| 1/26/2019 | Listed for rent | $2,995-7.8%$2/sqft |
Source: KELLER WILLIAMS WINTER PARK #O5759033 Report a problem | ||
| 1/23/2019 | Price change | $529,000-1.9%$316/sqft |
Source: Keller Williams Winter Park #O5754397 Report a problem | ||
| 1/4/2019 | Listed for sale | $539,000+7.8%$322/sqft |
Source: KELLER WILLIAMS WINTER PARK #O5754397 Report a problem | ||
| 8/24/2018 | Listing removed | $3,250$2/sqft |
Source: Keller Williams at the Parks Realty #O5709459 Report a problem | ||
| 8/22/2018 | Listed for rent | $3,250$2/sqft |
Source: Keller Williams at the Parks Realty #O5709459 Report a problem | ||
| 8/6/2018 | Listing removed | $499,999$299/sqft |
Source: Keller Williams at the Parks Realty #O5700750 Report a problem | ||
| 7/20/2018 | Listed for sale | $499,999+68.3%$299/sqft |
Source: Keller Williams at the Parks Realty #O5700750 Report a problem | ||
| 4/14/2015 | Sold | $297,000-4.2%$178/sqft |
Source: Stellar MLS #O5346570 Report a problem | ||
| 1/16/2007 | Sold | $310,000+181.8%$185/sqft |
Source: Stellar MLS #O4708670 Report a problem | ||
| 12/7/1998 | Sold | $110,000$66/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $8,492 +3.7% | $540,314 +3.3% |
| 2023 | $8,188 +42.6% | $523,058 +27.2% |
| 2022 | $5,741 +1.2% | $411,102 +3% |
| 2021 | $5,675 +6.3% | $399,128 +19.9% |
| 2020 | $5,339 +24.5% | $332,829 +10.2% |
| 2019 | $4,290 +0.6% | $302,028 +1.9% |
| 2018 | $4,262 | $296,396 -0.1% |
| 2017 | $4,262 +1% | $296,834 +17.4% |
| 2016 | $4,220 +17.1% | $252,943 +10.3% |
| 2015 | $3,604 +56.9% | $229,224 +23.2% |
| 2014 | $2,297 +2.5% | $186,080 +2.2% |
| 2013 | $2,240 +1.4% | $182,163 +11.7% |
| 2012 | $2,209 -11.4% | $163,088 -8.7% |
| 2011 | $2,494 -12.2% | $178,626 -12.3% |
| 2010 | $2,839 | $203,787 -17.9% |
| 2009 | -- | $248,341 -17% |
| 2008 | $4,261 +207% | $299,106 -23% |
| 2007 | $1,388 -6% | $388,492 +47% |
| 2006 | $1,477 +0.6% | $264,364 +27.5% |
| 2005 | $1,468 +5.2% | $207,277 +49.7% |
| 2004 | $1,395 +6.1% | $138,421 +0.6% |
| 2003 | $1,315 +3.3% | $137,641 +18.7% |
| 2002 | $1,273 +0.8% | $115,949 +11.5% |
| 2001 | $1,263 +3.2% | $104,007 +3.3% |
| 2000 | $1,223 | $100,673 |
Find assessor info on the county website
Neighborhood: 32789
Nearby homes
- $530,0002 bd2 ba1.1k sqft1409 Sunset Dr, Winter Park, FL 32789Sold
- $683,1003 bd2 ba2.5k sqft1431 Sunset Dr, Winter Park, FL 32789Off Market
- $1,809,6004 bd4 ba3.1k sqft1371 Sunset Dr, Winter Park, FL 32789Off Market
- $2,194,7004 bd4 ba4.1k sqft1400 Lake Knowles Cir, Winter Park, FL 32789Off Market
- $1,207,7003 bd3 ba2.9k sqft1428 Lake Knowles Cir, Winter Park, FL 32789Off Market
- $1,262,2003 bd2 ba1.2k sqft1461 Sunset Dr, Winter Park, FL 32789Off Market
- $592,3003 bd2 ba1.2k sqft1434 Sunset Dr, Winter Park, FL 32789Off Market
- $1,464,0003 bd3 ba2.7k sqft1420 Sunset Dr, Winter Park, FL 32789Off Market
Nearby schools
GreatSchools rating
- 7/10Lakemont Elementary SchoolGrades: K-5Distance: 0.5 mi
- 6/10Maitland Middle SchoolGrades: 6-8Distance: 1.7 mi
- 7/10Winter Park High SchoolGrades: 9-12Distance: 2 mi
Schools provided by the listing agent
- Elementary: Lakemont Elem
- Middle: Maitland Middle
- 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.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$820,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$820,200
- Florida
- Orange County
- Winter Park
- 32789
- 1421 SUNSET DRIVE
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Winter Park Topics
