1711 Chestnut Ave Winter Park, FL 32789
Estimated payment $6,013/month
Total Views
300
4
Beds
3
Baths
2,720
Sq Ft
$382
Price per Sq Ft
Highlights
- In Ground Pool
- Open Floorplan
- Deck
- Winter Park High Rated A+
- Midcentury Modern Architecture
- 5-minute walk to Phelps Park
About This Home
Under contract-accepting backup offers. Welcome home to this beautifully maintained property on more than a third of an acre in one of Winter Park's favorite neighborhoods -- affectionately known as the Tree Streets! 1711 Chestnut Ave blends classic Florida design with intentional, modern systems. In both the front and back of the home, you'll appreciate the attention to detail in the landscape design, which will be in full bloom each Spring. The irrigation system for the lawn is on it's own well system. Enter the home to enjoy two separate living spaces, a split plan that offers a spacious primary suite and three secondary bedrooms, and three full bathrooms. The kitchen has been renovated to include custom cabinetry, granite countertops, and stainless steel appliances. It is open to the Family Room with an incredible view of the oversized backyard and pool. The mature landscaping out back offers privacy to enjoy this retreat, complete with ample space for outdoor living and entertaining! Some notable upgrades to this property include brand new HVAC systems (2) in 2021 and 2022, water heater in 2019, hurricane-rated windows between 2015-2017, home security in 2015, engineered hardwood flooring in 2015, custom wood shutters in 2017, new pool pump in 2016, and a re-plumb in 2005. Zoned for highly rated Orange County Public Schools (Lakemont, Maitland, and Winter Park), you're also central to some of the best shopping and dining in Winter Park: 2 miles from Park Avenue, 0.4 miles from the Winter Park YMCA, 0.3 miles from Phelps Park (playground, pickleball, tennis), 1.5 miles from the nearest Publix, 1.1 miles from Interlachen Country Club, and 14 miles from Orlando International Airport.
Listing Agent
MILLER GRANT AND COMPANY Brokerage Phone: 407-399-6031 License #3493300 Listed on: 08/20/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $4,153
Year Built
- Built in 1963
Lot Details
- 0.36 Acre Lot
- South Facing Home
- Fenced
- Mature Landscaping
- Oversized Lot
- Irregular Lot
- Well Sprinkler System
- Cleared Lot
- Landscaped with Trees
- Property is zoned R-1A
Parking
- 2 Car Attached Garage
- Garage Door Opener
Home Design
- Midcentury Modern Architecture
- Traditional Architecture
- Slab Foundation
- Shingle Roof
- Built-Up Roof
- Block Exterior
Interior Spaces
- 2,720 Sq Ft Home
- 1-Story Property
- Open Floorplan
- Crown Molding
- Ceiling Fan
- Skylights
- Shutters
- French Doors
- Family Room with Fireplace
- Great Room
- Family Room Off Kitchen
- Combination Dining and Living Room
- Home Security System
Kitchen
- Eat-In Kitchen
- Built-In Oven
- Cooktop with Range Hood
- Recirculated Exhaust Fan
- Ice Maker
- Dishwasher
- Stone Countertops
- Solid Wood Cabinet
- Disposal
Flooring
- Engineered Wood
- Slate Flooring
Bedrooms and Bathrooms
- 4 Bedrooms
- Walk-In Closet
- 3 Full Bathrooms
Laundry
- Laundry in Garage
- Dryer
- Washer
Pool
- In Ground Pool
- Gunite Pool
- Pool Deck
- Outside Bathroom Access
- Diving Board
Outdoor Features
- Deck
- Patio
- Exterior Lighting
- Rain Gutters
- Private Mailbox
- Front Porch
Schools
- Lakemont Elementary School
- Maitland Middle School
- Winter Park High School
Utilities
- Zoned Heating and Cooling
- Heat Pump System
- Vented Exhaust Fan
- Thermostat
- Underground Utilities
- Electric Water Heater
- High Speed Internet
- Phone Available
- Cable TV Available
Community Details
- No Home Owners Association
- Conwill Estates Subdivision
Listing and Financial Details
- Visit Down Payment Resource Website
- Legal Lot and Block 7 / A
- Assessor Parcel Number 32-21-30-1708-01-070
Map
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Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $4,153 | $297,299 | -- | -- |
| 2024 | $3,971 | $297,299 | -- | -- |
| 2023 | $3,971 | $280,505 | $0 | $0 |
| 2022 | $3,597 | $272,335 | $0 | $0 |
| 2021 | $3,550 | $264,403 | $0 | $0 |
| 2020 | $3,410 | $260,752 | $0 | $0 |
| 2019 | $3,521 | $254,890 | $0 | $0 |
| 2018 | $3,496 | $250,137 | $0 | $0 |
| 2017 | $3,459 | $464,239 | $329,600 | $134,639 |
| 2016 | $3,386 | $452,056 | $320,000 | $132,056 |
| 2015 | $3,467 | $433,354 | $310,000 | $123,354 |
| 2014 | $3,495 | $344,488 | $236,000 | $108,488 |
Source: Public Records
Property History
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 08/20/2025 08/20/25 | Pending | -- | -- | -- |
| 08/20/2025 08/20/25 | For Sale | $1,040,000 | -- | $382 / Sq Ft |
Source: Stellar MLS
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Deed | $220,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $150,000 | Credit Line Revolving | |
| Closed | $165,500 | New Conventional | |
| Closed | $176,000 | No Value Available |
Source: Public Records
Similar Homes in Winter Park, FL
Source: Stellar MLS
MLS Number: O6335913
APN: 32-2130-1708-01-070
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Listing Information presented by local MLS brokerage: Ten-X - (888)-952-6393
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