1506 CHESTNUT AVE., Winter Park, FL 32789
OFF MARKET

$2,444,700

Trulia Estimate
  • 5 Beds
  • 5 Baths
  • 3,545 sqft

1506 CHESTNUT AVE., Winter Park, FL 32789

Est. Refi. Payment $17,347/mo*
Refinance Your Home
Currently Off Market - Sold Feb 28, 2025 for $2,500,000

Home Value

Trulia Estimate
$2.44M
Since last month
Increased$13K (+0.5%)
Since last year
Decreased$16K (-0.7%)
Since last sale
Decreased$42K (-1.7%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +642% in the last 10 years
MonthEstimated value
2026
September 2026$2.46M
August 2026$2.44M
July 2026$2.46M
June 2026$2.47M
May 2026$2.46M
April 2026$2.44M
March 2026$2.41M
February 2026$2.43M
January 2026$2.44M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1630 ELM AVENUE, Winter Park, FL
0.23
Single-Family Home
$2,325,000
09/16/26
5
4.5
3,408
1540 PALM AVENUE, Winter Park, FL
0.07
Single-Family Home
$1,860,000
03/26/26
5
3.5
3,423
1351 MAGNOLIA AVENUE, Winter Park, FL
0.25
Single-Family Home
$3,000,000
07/22/26
5
4.5
3,460
1661 PALM AVENUE, Winter Park, FL
0.20
Single-Family Home
$2,295,000
12/16/25
4
5
3,570
1750 WALNUT AVENUE, Winter Park, FL
0.24
Single-Family Home
$1,950,000
09/04/26
4
4.5
3,691
1612 MAGNOLIA AVENUE, Winter Park, FL
0.22
Single-Family Home
$1,850,000
12/12/25
4
4
3,153
1710 ONECO AVENUE, Winter Park, FL
0.28
Single-Family Home
$1,810,000
03/31/26
5
4.5
3,240
1752 CHESTNUT AVENUE, Winter Park, FL
0.25
Single-Family Home
$1,875,000
01/01/26
4
4.5
3,314
1781 PINE AVENUE, Winter Park, FL
0.33
Single-Family Home
$2,037,500
11/24/25
5
4.5
3,882
1630 CHESTNUT AVENUE, Winter Park, FL
0.11
Single-Family Home
$1,690,000
03/06/26
3
4.5
3,164

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1525 WILBAR CIRCLE, Winter Park, FL 32789
0.04
$1,449,400
4
4.5
2,842
Off Market
1500 Sunset Dr, Winter Park, FL 32789
0.06
$1,082,200
4
2.5
2,190
Off Market
1611 WALNUT AVENUE, Winter Park, FL 32789
0.08
$1,150,000
4
3
2,635
Recently Sold
1450 CHESTNUT AVENUE, Winter Park, FL 32789
0.02
$1,095,000
3
3.5
1,942
Recently Sold
1580 CHESTNUT AVENUE, Winter Park, FL 32789
0.07
$684,900
3
2
1,482
Off Market
1541 CHESTNUT AVENUE, Winter Park, FL 32789
0.05
$1,585,900
4
3
2,840
Off Market
1511 CHESTNUT AVENUE, Winter Park, FL 32789
0.04
$665,100
2
2
1,275
Off Market
1610 CHESTNUT AVENUE, Winter Park, FL 32789
0.09
$968,600
3
2.5
2,140
Off Market
1531 SUNSET DRIVE, Winter Park, FL 32789
0.07
$1,277,500
4
2.5
2,619
Off Market
1585 CHESTNUT AVENUE, Winter Park, FL 32789
0.08
$973,900
4
2.5
2,220
Off Market
1601 CHESTNUT AVENUE, Winter Park, FL 32789
0.09
$1,269,900
4
3
2,795
Off Market

Local Information

  • Map ViewExplore the area around 1506 CHESTNUT AVE..
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2021
3,545 sqft
$690/sqft
2 Car Garage

About this House

In one of Winter Parks desired neighborhoods, this exquisite Bates Custom Homes house is a three-year-old modern farmhouse that offers the ideal blend of style, luxury and comfort. With five spacious bedrooms, a creative hub and 4.5 beautifully appointed baths, this home is designed for relaxed living and elegant entertaining. The primary suite is downstairs and boasts large windows and a spa-like bath with dual vanities, a soaking tub, a walk-in shower and a custom walk-in closet. An additional four bedrooms are upstairs. The heart of the home is the open-concept kitchen, featuring top-of-the-line appliances like Wolf and Sub-Zero, that make cooking a pleasure. Adjacent to the kitchen, you'll find a light-filled eating area and cozy living space, ideal for family gatherings while turning the surround sound on listening to your favorite tunes or watching your favorite movie. A thoughtfully designed office provides the space for remote work or study. Step outside to your own private oasis, where a charming veranda overlooks a sparkling heated pool and spa, and a fully equipped cabana house. Complete with a fireplace, outdoor kitchen and bath, this space is ideal for year-round entertaining. The expansive backyard is a peaceful retreat, with lush landscaping providing privacy and tranquility. Additional features include a large, functional laundry room with a dedicated dog-washing station making it convenient for the pet owner. There is also an extra washer and dryer upstairs. This home is a masterpiece, combining modern sophistication with comfort and practicality.
1506 CHESTNUT AVE., Winter Park, FL 32789 is a 5 bedroom, 6 bathroom, 3,545 sqft single-family home built in 2021. It last sold for the $2,495,000 asking price on Feb 28, 2025. More recently, it was listed as a rental in August 2019 with an asking price of $1,795 per month. That rental listing was removed on September 11, 2019. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,444,700, with a rent estimate of $10,112/month.
Last check for updates: about 1 hour ago
Listed by Alison Mosley, (407) 304-6458
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Bought with: Alison Mosley, (407) 304-6458, PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6272231
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 1506 CHESTNUT AVE.

Interior Features

Interior Details
Number of Rooms: 8Types of Rooms: Primary Bedroom, Bedroom 1, Bedroom 2, Bedroom 3, Bedroom 4, Den, Kitchen, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3545 Square Feet
Appliances & Utilities
Utilities: Cable Available, Cable Connected, Propane, Street Lights, Underground UtilitiesAppliances: Bar Fridge, Oven, Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, Range, Range Hood, Refrigerator, Trash Compactor, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Natural GasHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Spa: HeatedHas a FireplaceHas a Spa
Windows, Doors, Floors & Walls
Window: Window TreatmentsDoor: Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sliding DoorsFlooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Hardwood
View
No View
Security
Security: Fire Alarm, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: Metal ShingleFencing: FencedOther Structures: CabanaExterior: Dog Run, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Outdoor Shower, Sidewalk, StorageFoundation: Block, SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Garage Attached
Pool
Pool: Heated, In GroundPool
Frontage
Road Surface Type: BrickNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 3

Property Information

Year Built
Year Built: 2021
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: StuccoNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 322130453602181

Price & Status

Price
List Price: $2,495,000
Status Change & Dates
Off Market Date: Mon Jan 20 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: LAKE KNOWLES TERRACE
School Information
Elementary School: Lakemont ElemJr High / Middle School: Maitland MiddleHigh School: Winter Park High

Building

Building Details
Builder Name: Bates Custom Homes
Building Area
Building Area: 5131 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 9061 sqft

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6272231Showing Advance Notice: 24Showing Requirements: 24 Hour Notice, Call Before Showing, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-322130453602181-R-N

Price and Tax history

DateEventPrice
Feb 28, 2025
Source: Stellar MLS #O6272231
Sold
$2,500,000
Jan 21, 2025
Source: Stellar MLS #O6272231
Pending
$2,495,000
Jan 17, 2025
Source: Stellar MLS #O6272231
Listed For Sale
$2,495,000
Sep 11, 2019
Source: Agent Provided
ListingRemoved
$1,795
Aug 1, 2019
Source: Agent Provided
Listed For Rent
$1,795

Market trends in Winter Park

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$455K
$4.03KMoM
Sale-to-List Price
98.1%
0.1%MoM
Price per sq ft
$281
$6MoM
Available listings
382
13MoM

Around this home

What Locals Say about Winter Park

At least 596 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 80 % Say parking is easy

  • 74 % Say there's holiday spirit

  • 70 % Say yards are well-kept

  • 68 % Say it's quiet

  • 67 % Say streets are well-lit

  • 65 % Say people would walk alone at night

  • 62 % Say it's walkable to restaurants

  • 62 % Say kids play outside

  • 57 % Say it's walkable to grocery stores

  • 52 % Say they plan to stay for at least 5 years

  • 51 % Say neighbors are friendly

  • 39 % Say there's wildlife

  • 29 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "We are retired, so we do not need public transportation. I see many buses around the area, and there is a light rail train."
    0
    Flag
  • Giannina Munoz
    "All of them they are so family friendly especially around Halloween they have a haunted trail so cute "
    0
    Flag
  • Jasmine Miller
    "I see dogs everywhere. People often do meet and greets between dogs. There are always bowls of water as well as jars of dog treats often seen. "
    0
    Flag
  • Ed Agudelo
    "It is a nice neighborhood with lots to do locally and easy to walk to parks, restaurants and shops. "
    0
    Flag
  • Trulia User
    "Some people are great some aren’t great but close to shops and grocery stores sports cooking cleaning"
    0
    Flag
  • Heidiromy
    "The mature landscape, is safe and family friendly, pet friendly, quiet, beautiful, community oriented. "
    0
    Flag
  • Timothyjohnson
    "Winter park art festivals and Farmers Market are always a good time. There lots of great restaurants. "
    0
    Flag
  • andrea brewer
    "It’s a quiet and beautiful area that’s perfect for families and single professionals alike. Lots of great small businesses that thrive regardless of the time of year."
    0
    Flag
  • Paul Swain
    "Holidays are dull here. People keep to themselves. Everything is close by. Things are in good condition. Driving down town is a little hectic but worth it "
    0
    Flag
  • Gabrielcoello094
    "It’s a great place to live and raise your kids, I love it here, lot of things to do, good public schools around and safe."
    2
    Flag
  • Timothyjohnson
    "We used to have an annual parade for Goldenrod, but has not occurred in many years. There is a lack a “center” specifically for Goldenrod. "
    0
    Flag
  • Trulia User
    "I would say the only community events in this area are hosted by the elementary schools and those are okay but not enough "
    0
    Flag
  • Trulia User
    "It’s always traffic on Semoran. This area is just BUSY!! Early morning, all times of the day and late nights. "
    2
    Flag
  • Trulia User
    "You would need a car to get to most things, but there are a lot of little restaurants nearby if you like. "
    0
    Flag
  • Trulia User
    "everything is close buy like supermarkets post office and fat food places. it's a safe neighborhood. I have had no incidents since I moved here. it has that family feel to it as the people are friendly and look out for each other"
    3
    Flag
  • David S.
    "Very pet friendly. Lots of fellow dog owners in the area. Just make sure to clean up after your fur buddy"
    0
    Flag
  • Monique J.
    "Close to everything, 15 minutes to everything from downtown to schools. This neighborhood has a lot of good and is close to food and shopping. The neighborhood is kept clean with very little trash."
    8
    Flag
  • A R. S.
    "Rollins College and UCF colleges with events like sports close by. AmWay center and Campers World Stadium only 6 miles away for NBA , Football (Citrus Bowl) and Major music concerts. Park Ave beautiful shops, beautiful landscapes and beautiful people - - young and some what older."
    4
    Flag
  • Holly A. C.
    "No public transportation thats convenient.i drive a car and plenty Of parking lots and street parking "
    5
    Flag
  • Ross H.
    "I love winter Park have lived here for about 7 years and hope to live here longer. the people are nice and the area is clean "
    0
    Flag
  • Winterparkhomes
    "I have lived in Winter Park since 1988 and I Love it! It’s close proximity to groceries, hospital, restaurants and shopping is awesome !"
    2
    Flag
  • Messagedrop
    "Great place to live if you like to walk or ride bicycles. Close to shopping, entertainment, restaurants, college sports venues."
    0
    Flag
  • Francois B.
    "Most dog owners don’t pick up after them selfs and even when the park provides bags to clean the dogs needs"
    0
    Flag
  • Donna G.
    "Very trendy area! Family oriented! Grocery stores and great schools! A nice beautiful landscaped place to work and raise your family!"
    0
    Flag
  • Daylen C.
    "It’s historic and it’s established. Lots of charm and mature trees. You rarely see trash and the roads are lost. It’s very easy to grab a great bite to eat everywhere. My favorite place is the mead botanical gardens. A little escape in the middle of the city. "
    0
    Flag
  • Luna M.
    "It’s a safe and friendly neighborhood. Not really any crime, lots of people outside walking their dogs and parents feel safe enough to let their kids ride around on their bikes to the store or the parks or what have you. Great place to live all around. Highly recommend."
    6
    Flag
  • David C.
    "I just moved here last week and it seems like a nice area. There is a lot of traffic and it’s been warmer then up north."
    3
    Flag
  • George P.
    "right off a preserve and Lake Howell so lots of wildlife like turkeys, bald Eagles, hawks, herons, egrets, ibis and sandhill cranes always around. close to shopping restaurants and the gym"
    0
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  • Daniel V.
    "It’s a great and safe area, you’re in walking distances from lakes, parks, etc. you have a great shopping center and restaurants. "
    0
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  • Ross H.
    "area is amazing close to everything I've live around winter Park for about 7 years and can't find anything really wrong with it"
    0
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  • Heidi W.
    "Winter Park is a safe and happy place to raise a family. I have lived here since Kindergarten and I’m 33 now, raising my own family. "
    3
    Flag
  • Luna M.
    "I love it here. Can't go wrong living here. It's friendly, safe, quiet. I can't say enough good things about this neighborhood."
    2
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  • Nicole B.
    "Beautiful and very safe best place to raise a family. Lots of people go outdoors and exercise. Good for walking dogs and going to parks"
    2
    Flag
  • Elizabeth C.
    "Many restaurants are pet friendly. Park Ave is a great place to spend time at. Many public events are held there. On Saturday’s there’s the farmers market. "
    1
    Flag
  • Sarah S.
    "We have Cady way trail which is great for dogs and plenty of sidewalks and dog waste bag reciprocals. "
    1
    Flag
  • Blanca V.
    "I love this area. we moved here years ago. My children grew up here, went schools here and now they're in college. I wouldn't have it any other. Winter park has been good to us."
    3
    Flag
  • Joenaijah.sam
    "My neighbor has various restaurants to eat at all really good food. I truly enjoy cuban cafes and Japanese dishes. "
    0
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  • Jonvaden
    "I see people walking their dogs all the time on the sidewalks under streetlights so I think they are happy. I myself am not a pet owner."
    0
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  • Thompson C.
    "Perfect area to live. Close proximity to everything. Golfing, jogging, walks and casual stroll around the neighborhood is encouraged. Close access to major highways like I-4, 408 414. Plenty of restaurants to choose from Mexican, Thai, Indian, Italian etc. "
    1
    Flag
  • Blanca V.
    "There are many families living in this neighborhood and we have great parks and schools in the are. I love this place I've been living here for 7 years with my family and been happy to be in that one of the most beautiful cities in Florida. . Our schools are a plus schools in RL parks are amazingly beautiful the lakes are nice to be and spend an evening with your family or your couple "
    0
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LGBTQ Local Legal Protections

Frequently asked questions about 1506 CHESTNUT AVE.

  • What is 1506 CHESTNUT AVE. estimated to be worth?
    Trulia's estimated value for 1506 CHESTNUT AVE. in Winter Park, FL is $2,444,700.
  • What is the price history for 1506 CHESTNUT AVE.?
    1506 CHESTNUT AVE. in Winter Park, FL last sold for $2,500,000 in February 2025.
  • Is Winter Park a buyer's or seller's market?
    Winter Park is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Park?
    The median sale price in Winter Park is $455K. That is up $4.03K from the prior month.
  • Does 1506 CHESTNUT AVE. have air conditioning?
    Yes, 1506 CHESTNUT AVE. in Winter Park, FL has air conditioning.
  • Does 1506 CHESTNUT AVE. have a pool?
    Yes, 1506 CHESTNUT AVE. in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

160 pet-friendly rentals in Winter Park, FL

Explore by feature - Garage

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Explore by feature - Air Conditioning

173 rentals with air conditioning in Winter Park, FL

Explore by feature - Pool

145 rentals with a pool in Winter Park, FL

Explore by feature - Washer/dryer

188 rentals with a washer/dryer in Winter Park, FL

Explore by feature - Outdoor Space

57 rentals with an outdoor space in Winter Park, FL

Apartments for Rent

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Off Market Homes Near 1506 CHESTNUT AVE.

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