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$995,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 2,916 Sq. Ft.
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HUGE PRICE IMPROVEMENT!!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.

Full Property Details for 1611 Chestnut Ave

General

  • Price: $995,000
  • Taxes: $3,589 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6402502
  • Updated: 9/1/2026
  • Added to Site: 142 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 4
  • Interior Features: Ceiling Fan(s), Solid Surface Counters, Thermostat, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Family Room, Stone
  • Appliances: Dishwasher, Disposal, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Ceramic Tile, Engineered Hardwood, Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 4

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Sidewalk, Sprinkler Metered

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: LAKE KNOWLES TERRACE
  • Driving Directions: From Lakemont Ave and Aloma head north on Lakemont, straight onto Arbor Park Drive, left on Chestnut house is on the right
  • Direction Faces: Southeast

School Information

  • Elementary School: Lakemont Elem
  • Middle School: Maitland Middle
  • High School: Winter Park High

Community

  • Community Name: 32789 - Winter Park

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Exterior Const.: Block, Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,916
  • Sq. Ft. Source: Public Records
  • Year Built: 1973

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,508
  • Lot Size: 7508
  • Street/Road Desc.: Brick

Financial Considerations

  • Tax Amount: $3,589.55
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LAKE KNOWLES TERRACE K/4 LOT 10 BLK 1
  • Flood Zone Info: X
  • APN: 322130453601100
  • Property ID: 322130453601100
  • Block/Lot/Section: 1

Listed by Fannie Hillman & Associates

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Listing agents

— 1611 Chestnut Ave —

  • Fannie Hillman & Associates

  • Fannie Hillman & Associates

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1611 Chestnut Ave

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-50.5 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-81.5 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1611 Chestnut Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/04/2026
Price Reduced
$995,000
-4.33%
MLS
7/10/2026
Price Reduced
$1,040,000
-2.8%
MLS
6/10/2026
Price Reduced
$1,070,000
-2.73%
MLS
4/30/2026
Listed
$1,100,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1611 Chestnut Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$3,590
4%
$261,830
6%
2024
$3,456
5%
$247,761
3%
2023
$3,303
96%
$240,545
64%
2021
$1,689
-2%
$146,393
-3%
2022
$1,719
2%
$150,785
4%
2021
$1,689
2%
$144,372
2%
2019
$1,664
1%
$141,126
2%
2018
$1,648
1%
$138,495
2%
2017
$1,624
2%
$135,646
2%
2016
$1,587
-2%
$132,856
1%
2015
$1,625
-1%
$131,932
1%
2014
$1,637
3%
$130,885
1%
2013
$1,593
—
$128,951
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1611 Chestnut Ave

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Fannie Hillman & Associates

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1611 Chestnut Avenue, Winter Park, FL 32789 (MLS# O6402502) is a Single Family property with 4 bedrooms and 4 full bathrooms. 1611 Chestnut Avenue is currently listed for $995,000 and was received on April 30, 2026. Want to learn more about 1611 Chestnut Avenue? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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