Welcome to this thoughtfully expanded one-story home in Winter Park’s coveted “Tree Streets” neighborhood. A paved double drive and circular driveway create a gracious arrival with ample guest parking. Originally built in 1962 and expanded over time, this home offers a flexible floor plan designed for comfortable everyday living and effortless entertaining. Spacious living areas and the primary suite open to a stunning garden-like backyard, seamlessly connected by a full-length covered portico perfect for enjoying Florida’s indoor-outdoor lifestyle. The main hallway leads to the primary and guest bedrooms, along with a quiet sitting room overlooking the charming front porch. Expanded in the early 2000s, the private primary suite includes a generous bath with an oversized whirlpool tub, dual vanities, separate shower, dressing table, private water closet, and a spacious walk-in closet. At the heart of the home, the kitchen features solid wood cabinetry and solid-surface countertops, opening to the central family room with a traditional fireplace and casual dining area, all adjacent to the formal dining room. Just off the kitchen, a large flex space offers extensive built-ins, a desk area, dry bar, wine refrigerator, and integrated washer and dryer ideal for a home office, hobby room, or additional entertaining space. Located just minutes from Park Avenue, enjoy easy access to fine dining, boutique shopping, cafés, museums, and year-round community events. This one-story home offers abundant living space, exceptional entertaining areas, and a beautifully landscaped backyard complete with pool and outdoor living spaces all situated on a generous 77 x 150 lot.
Sold for $1,201,000
Zestimate®
$1,201,000
1723 Chestnut Ave, Winter Park, FL 32789
3beds
2,608sqft
Single Family Residence
Built in 1962
0.27 Acres Lot
$1,201,000 Zestimate®
$461/sqft
$4,343 Estimated rent
Home value
$1,201,000
$1.10M - $1.30M
$4,343/mo
Zestimate® history
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List your homeWhat's special
Dressing tableFormal dining roomSeparate showerPrivate primary suiteDual vanitiesPrivate water closetSpacious walk-in closet
Zillow last checked:
Listing updated:
Listed by:
Anne Rogers 407-649-4141,
ANNE ROGERS REALTY GROUP INC 407-649-4141
Bought with:
Kelly Price, 571579
KELLY PRICE & COMPANY LLC
Source: Stellar MLS,MLS#: O6402563
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 2
- 1/2 bathrooms: 1
Rooms
- Room types: Den/Library/Office, Family Room, Dining Room, Utility Room
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 323 Square Feet
- Dimensions: 19x17
Bedroom 1
- Features: Shower No Tub, Built-in Closet
- Level: First
- Area: 143 Square Feet
- Dimensions: 13x11
Bedroom 2
- Features: Built-in Closet
- Level: First
- Area: 120 Square Feet
- Dimensions: 12x10
Primary bathroom
- Features: Bath With Whirlpool, Dual Sinks, Tub with Separate Shower Stall, Water Closet/Priv Toilet
- Level: First
- Area: 209 Square Feet
- Dimensions: 19x11
Dining room
- Level: First
- Area: 238 Square Feet
- Dimensions: 17x14
Family room
- Level: First
- Area: 525 Square Feet
- Dimensions: 25x21
Kitchen
- Features: Pantry, Kitchen Island
- Level: First
- Area: 169 Square Feet
- Dimensions: 13x13
Living room
- Level: First
- Area: 234 Square Feet
- Dimensions: 18x13
Office
- Features: Bar, Built-in Features, Stone Counters
- Level: First
- Area: 221 Square Feet
- Dimensions: 17x13
Heating
- Central, Heat Pump
Cooling
- Central Air
Appliances
- Included: Bar Fridge, Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Refrigerator, Tankless Water Heater
- Laundry: Inside, Laundry Room
Features
- Crown Molding, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Walk-In Closet(s)
- Flooring: Hardwood
- Doors: French Doors
- Has fireplace: Yes
- Fireplace features: Family Room
Interior area
- Total structure area: 3,882
- Total interior livable area: 2,608 sqft
Property
Parking
- Total spaces: 2
- Parking features: Circular Driveway, Driveway, Garage Door Opener, Guest
- Attached garage spaces: 2
- Has uncovered spaces: Yes
- Details: Garage Dimensions: 24X18
Features
- Levels: One
- Stories: 1
- Patio & porch: Covered, Front Porch, Patio, Rear Porch
- Exterior features: Irrigation System, Rain Gutters
- Has private pool: Yes
- Pool features: Gunite, In Ground, Tile
- Has spa: Yes
- Spa features: In Ground
- Fencing: Fenced,Vinyl
Lot
- Size: 0.27 Acres
- Dimensions: 77 x 150
- Features: Landscaped
- Residential vegetation: Mature Landscaping
Details
- Parcel number: 322130170801060
- Zoning: R-1A
- Special conditions: None
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Traditional
- Property subtype: Single Family Residence
Materials
- Block, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1962
Utilities & green energy
- Sewer: Public Sewer
- Water: None
- Utilities for property: Cable Connected, Electricity Connected, Propane, Sewer Connected
Community & HOA
Community
- Pet fee: $0 monthly
- Subdivision: CONWILL ESTATES
HOA
- Has HOA: No
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $461/sqft
- Tax assessed value: $996,491
- Annual tax amount: $4,879
- Date on market: 5/7/2026
- Cumulative days on market: 1 day
- Listing terms: Cash,Conventional
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 6/18/2026 | Sold | $1,201,000+6.8%$461/sqft |
Source:  Stellar MLS #O6402563 Report a problem | ||
| 5/8/2026 | Pending sale | $1,125,000$431/sqft |
Source: Stellar MLS #O6402563 Report a problem | ||
| 5/7/2026 | Listed for sale | $1,125,000+1117.5%$431/sqft |
Source: Stellar MLS #O6402563 Report a problem | ||
| 1/1/1986 | Sold | $92,400$35/sqft |
Source: Agent Provided Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2024 | $4,687 +4.8% | $313,222 +3% |
| 2023 | $4,471 +13.2% | $304,099 +3% |
| 2022 | $3,951 +1.3% | $295,242 +3% |
| 2021 | $3,901 -0.1% | $286,643 +1.4% |
| 2020 | $3,904 +0.9% | $282,685 +2.3% |
| 2019 | $3,870 +0.7% | $276,329 +1.9% |
| 2018 | $3,845 | $271,177 -42.7% |
| 2017 | $3,845 +1% | $473,380 +2.5% |
| 2016 | $3,805 +2.1% | $461,950 +5.9% |
| 2015 | $3,725 -3.1% | $436,187 +24.1% |
| 2014 | $3,846 +2.3% | $351,620 +17% |
| 2013 | $3,758 +1.2% | $300,622 +8.2% |
| 2012 | $3,714 +3.2% | $277,933 -4.8% |
| 2011 | $3,600 +5.3% | $291,998 -10.2% |
| 2010 | $3,418 | $325,224 -18% |
| 2009 | -- | $396,452 -12.7% |
| 2008 | $3,145 -3.1% | $454,372 +1% |
| 2007 | $3,244 -6.4% | $449,989 +22.4% |
| 2006 | $3,466 +0.1% | $367,743 +19.4% |
| 2005 | $3,463 +4.7% | $307,885 +19.8% |
| 2004 | $3,309 +5.7% | $256,978 +0.9% |
| 2003 | $3,131 +2.8% | $254,708 +12.8% |
| 2002 | $3,045 +0.5% | $225,742 +10.7% |
| 2001 | $3,030 +16.4% | $203,954 +15.9% |
| 2000 | $2,603 | $175,968 |
Find assessor info on the county website
Neighborhood: 32789
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Nearby schools
GreatSchools rating
- 7/10Lakemont Elementary SchoolGrades: K-5Distance: 0.5 mi
- 6/10Maitland Middle SchoolGrades: 6-8Distance: 1.6 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.
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Estimated market value
$1,201,000
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Estimated market value
$1,201,000
- Florida
- Orange County
- Winter Park
- 32789
- 1723 Chestnut Ave
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