HUGE PRICE IMPROVEMENT!! BRING ALL OFFERS!! Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — every step of this rennovation was completed with quality and permanence in mind. With elevated finishes, like designer tile and quartz countertops, beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.
For sale
Price cut: $45K (8/4)
$995,000
1611 CHESTNUT AVENUE, WINTER PARK, FL 32789
4beds
2,916sqft
Single Family Residence
Built in 1973
7,508 Square Feet Lot
$963,900 Zestimate®
$341/sqft
$-- HOA
What's special
Home officeQuartz countertopsElevated finishesDesigner tileCustom tile workWelcoming fireplaceLush mature landscaping
- 123 days
- 2,056
- 98
Zillow last checked:
Listing updated:
Listed by:
Olivia Maxwell 407-222-4440,
FANNIE HILLMAN & ASSOCIATES 407-644-1234,
Julia Dalessandro 407-486-9651,
FANNIE HILLMAN & ASSOCIATES
Source: Stellar MLS,MLS#: O6402502
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 4
Primary bedroom
- Features: Built-in Features, Walk-In Closet(s)
- Level: Second
- Area: 504 Square Feet
- Dimensions: 21x24
Bedroom 1
- Features: Walk-In Closet(s)
- Level: First
- Area: 168 Square Feet
- Dimensions: 12x14
Kitchen
- Features: Kitchen Island
- Level: First
- Area: 216 Square Feet
- Dimensions: 18x12
Living room
- Features: Built-In Shelving
- Level: First
- Area: 336 Square Feet
- Dimensions: 16x21
Heating
- Central, Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Range, Refrigerator
- Laundry: Laundry Room
Features
- Ceiling Fan(s), Solid Surface Counters, Thermostat, Walk-In Closet(s)
- Flooring: Ceramic Tile, Engineered Hardwood, Luxury Vinyl
- Has fireplace: Yes
- Fireplace features: Family Room, Stone
Interior area
- Total structure area: 3,316
- Total interior livable area: 2,916 sqft
Video & virtual tour
Property
Parking
- Total spaces: 2
- Parking features: Garage - Attached
- Attached garage spaces: 2
Features
- Levels: Two
- Stories: 2
- Exterior features: Sidewalk, Sprinkler Metered
Lot
- Size: 7,508 Square Feet
Details
- Parcel number: 322130453601100
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Block, Stucco, Wood Frame
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1973
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Electricity Connected, Sewer Connected, Water Connected
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: $341/sqft
- Tax assessed value: $747,448
- Annual tax amount: $3,589
- Date on market: 4/30/2026
- Cumulative days on market: 123 days
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Brick
Estimated market value
$963,900
$916,000 - $1.01M
$6,444/mo
Price history
| Date | Event | Price |
|---|---|---|
| 8/4/2026 | Price change | $995,000-4.3%$341/sqft |
Source:  Stellar MLS #O6402502 Report a problem | ||
| 7/10/2026 | Price change | $1,040,000-2.8%$357/sqft |
Source: Stellar MLS #O6402502 Report a problem | ||
| 6/10/2026 | Price change | $1,070,000-2.7%$367/sqft |
Source: Stellar MLS #O6402502 Report a problem | ||
| 4/30/2026 | Listed for sale | $1,100,000-7.9%$377/sqft |
Source: Stellar MLS #O6402502 Report a problem | ||
| 8/15/2025 | Listing removed | $1,195,000$410/sqft |
Source: Stellar MLS #O6281275 Report a problem | ||
| 7/3/2025 | Price change | $1,195,000-7.7%$410/sqft |
Source: Stellar MLS #O6281275 Report a problem | ||
| 2/15/2025 | Listed for sale | $1,295,000+4.4%$444/sqft |
Source: Stellar MLS #O6281275 Report a problem | ||
| 10/18/2023 | Listing removed | -- |
Source: Stellar MLS #O6133987 Report a problem | ||
| 8/14/2023 | Listed for sale | $1,240,000+188.4%$425/sqft |
Source: Stellar MLS #O6133987 Report a problem | ||
| 5/22/2017 | Listing removed | $429,900$147/sqft |
Source: RE/MAX 200 REALTY #O5470306 Report a problem | ||
| 10/12/2016 | Listed for sale | $429,900+343.2%$147/sqft |
Source: RE/MAX 200 REALTY #O5470306 Report a problem | ||
| 11/26/1991 | Sold | $97,000$33/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $3,456 +4.6% | $247,761 +3% |
| 2023 | $3,303 +92.2% | $240,545 +59.5% |
| 2022 | $1,719 +1.8% | $150,785 +3% |
| 2021 | $1,689 +0.2% | $146,393 +1.4% |
| 2020 | $1,685 +1.2% | $144,372 +2.3% |
| 2019 | $1,665 +1% | $141,126 +1.9% |
| 2018 | $1,648 | $138,495 -58.9% |
| 2017 | $1,648 +1.5% | $337,079 +2.7% |
| 2016 | $1,624 +2.3% | $328,178 +11.2% |
| 2015 | $1,587 -3% | $295,210 +24.4% |
| 2014 | $1,637 +2.8% | $237,242 +16.5% |
| 2013 | $1,593 +1.6% | $203,698 +9.6% |
| 2012 | $1,568 +3.9% | $185,892 -1.1% |
| 2011 | $1,510 +6.2% | $188,002 -10.7% |
| 2010 | $1,422 | $210,516 -17.9% |
| 2009 | -- | $256,505 -14.2% |
| 2008 | $1,293 -64% | $299,019 -13.9% |
| 2007 | $3,590 +8.1% | $347,345 +23.5% |
| 2006 | $3,322 +5.7% | $281,219 +10.8% |
| 2005 | $3,142 +26.3% | $253,884 +33.5% |
| 2004 | $2,487 +5.2% | $190,243 +1.1% |
| 2003 | $2,363 +12.3% | $188,103 +16.1% |
| 2002 | $2,105 +37.2% | $161,999 +31.9% |
| 2001 | $1,534 +3.3% | $122,812 +3.4% |
| 2000 | $1,485 | $118,781 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 32789
Nearby schools
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.
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