266 Chase Ave, Winter Park, FL 32789
OFF MARKET

266 Chase Ave
Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,088 sqft (on 0.31 acres)

$2,918,600

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $19,922/mo*
Refinance Your Home

$2,918,600

Trulia Estimate
as of Jul 8, 2026
Est. Refi. Payment $19,922/mo*
Refinance Your Home
5 Beds
5.5 Baths
4,088 sqft
(on 0.31 acres)

Local Information

  • Map ViewExplore the area around 266 Chase Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll to the world-renowned Park Avenue, this home offers not only luxurious living but an unparalleled lifestyle in one of Central Florida’s sought-after communities. Park Avenue is the heartbeat of Winter Park, a tree-lined promenade brimming with charm, home to award-winning restaurants, boutique shopping, art galleries and cultural landmarks. Residents and visitors alike are drawn to its timeless ambiance, where the rhythm of the day flows from morning coffee at a corner café to evening dinners under twinkling lights. Whether enjoying “Movies in the Park,” seasonal art festivals, the lively Winter Park Farmers’ Market or beloved holiday parades, living here means having a front-row seat to all of Winter Park’s treasured traditions. Originally built in the 1930s, this five-bedroom, 5.5-bath home has been meticulously renovated in recent years to preserve its historic character while seamlessly incorporating every modern convenience. From the moment you enter, you’re greeted by gleaming hardwood floors, classic architectural details and a warm, inviting atmosphere. The gracious living room centers around a charming fireplace, flanked by two sets of French doors that lead to a cozy sunroom, ideal for morning coffee or afternoon reading. A formal dining room provides an elegant setting for entertaining, while the open-concept kitchen and family room encompass a blend of functionality and style. The kitchen is a showpiece, featuring a large 15-foot Soma quartz island and countertops and marble backsplash, handcrafted cabinetry, top-of-the-line Wolf and Sub-Zero appliances, and a custom wet bar with under-counter wine refrigerator. It’s a space designed for gatherings, large or small. The expansive and private primary suite is on the main level and features a walk-in closet with custom built-ins and a luxurious en-suite bath with dual sinks and a marble/glass shower. Upstairs, you’ll find three additional bedroom suites, including one that could easily serve as a second primary suite, complete with French doors leading to a covered balcony. Each bedroom offers its own en-suite bath, hardwood floors and thoughtfully designed closet space with built-ins. A spacious first-floor laundry room offers ample storage, while the detached two-car garage includes a beautifully renovated first-floor guest cottage. Complete with a kitchenette, full bath, and cedar-lined walk-in closet, it’s the ideal space for guests, a home office or extended family. Surrounded by lush landscaping and a charming circular driveway, this home radiates curb appeal and classic Winter Park style. Whether you're walking to Park Avenue for dinner, enjoying a leisurely afternoon in Central Park, or simply soaking in the historic beauty of your neighborhood, this home places you at the center of it all. This is more than just a home, it’s a lifestyle and a rare chance to own one of Winter Park’s rare downtown area treasured properties.
266 Chase Ave, Winter Park, FL 32789 is a 5 bedroom, 6 bathroom, 4,088 sqft single-family home built in 1930. It last sold for $2,935,000 on May 27, 2025 (10% below the $3,250,000 asking price). It is currently off market. The Trulia Estimate is $2,918,600, with a rent estimate of $7,218/month.

Home Highlights

Parking
Garage
Outdoor
Porch, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 266 Chase Ave

Interior Features

Interior Details
Basement: PartialNumber of Rooms: 11Types of Rooms: Primary Bedroom, Primary Bedroom 2, Bedroom 3, Bedroom 5, Primary Bathroom, Bathroom 4, Dining Room, Family Room, Florida Room, Kitchen, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4088 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Natural Gas Connected, Public, Sewer Connected, Street Lights, Water ConnectedAppliances: Bar Fridge, Dishwasher, Disposal, Dryer, Range, Range Hood, Refrigerator, WasherDishwasherDisposalDryerLaundry: Inside,Laundry RoomRefrigeratorWasher
Heating & Cooling
Heating: Central,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Living RoomHas a Fireplace
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: ShuttersDoor: French DoorsFlooring: Marble, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Marble, Tile, Hardwood
View
No View
Security
Security: Security System, Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShakePatio / Porch: Covered, Deck, Front Porch, PorchVegetation: Mature Landscaping, Trees/LandscapedOther Structures: Guest HouseExterior: Irrigation System, Rain Gutters, SidewalkFoundation: Basement, Crawlspace, SlabNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener
Frontage
Road Surface Type: BrickNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 30

Property Information

Year Built
Year Built: 1930
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 072230297200030

Price & Status

Price
List Price: $3,250,000
Status Change & Dates
Off Market Date: Sat May 03 2025

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: GIBBS SUB
School Information
Elementary School: Audubon Park K8Jr High / Middle School: Audubon Park K-8High School: Winter Park High

Building

Building Area
Building Area: 4662 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.31 acres

Listing Info

Special Conditions: None

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: O6296421Showing AttendedShowing Considerations: See RemarksShowing Requirements: Appointment Only, Listing Agent Must Accompany, See Remarks, ShowingTimeUniversal Property Id: US-12095-N-072230297200030-R-N
Last check for updates: about 3 hours ago
Listed by Mick Night, (407) 629-4446
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Bought with: Padgett McCormick, (407) 929-5604, KELLY PRICE & COMPANY LLC, (407) 645-4321
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6296421
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

Price History for 266 Chase Ave

DatePriceEventSource
05/27/2025$2,935,000Sold
Stellar MLS #O6296421
05/06/2025$3,250,000PendingStellar MLS #O6296421
04/03/2025$3,250,000Listed For SaleStellar MLS #O6296421
07/12/2024$1,995,000ListingRemovedStellar MLS #O5932396
07/15/2021$1,993,500Sold
N/A
04/16/2021$1,995,000PendingStellar MLS #O5932396
04/13/2021$1,995,000Listed For SaleStellar MLS #O5932396
06/05/2019$2,149,000ListingRemovedAgent Provided
04/17/2019$2,149,000PriceChange
Agent Provided
03/11/2019$2,249,000PriceChange
Agent Provided
02/12/2019$2,399,000PriceChange
Agent Provided
10/29/2018$2,495,000Listed For SaleAgent Provided
04/15/2013$736,500Sold
Stellar MLS #O5148019
05/20/1994$330,000Sold
N/A

Market trends in Winter Park

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$445K
$11.4KMoM
Sale-to-List Price
97.4%
0.5%MoM
Price per sq ft
$289
$4MoM
Available listings
371
6MoM
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Property Tax and Assessment

Year2024
Tax$26,112
Assessment$2,035,141
Home facts updated by county records

Comparable Sales for 266 Chase Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
516 Henkel Cir, Winter Park, FL
0.36
Single-Family Home
$2,925,000
03/24/26
5
6
4,143
501 Henkel Cir, Winter Park, FL
0.29
Single-Family Home
$1,905,000
04/10/26
5
4.5
3,746
473 Fletcher Pl, Winter Park, FL
0.74
Single-Family Home
$3,000,000
05/15/26
5
5.5
4,296
234 Detmar Dr, Winter Park, FL
0.39
Single-Family Home
$1,400,000
06/25/26
4
5.5
3,609
185 Sylvan Blvd, Winter Park, FL
0.58
Single-Family Home
$2,500,000
03/06/26
4
4.5
3,138
255 Stirling Ave, Winter Park, FL
0.75
Single-Family Home
$2,835,000
11/24/25
4
3.5
3,635
374 Henkel Cir, Winter Park, FL
0.25
Single-Family Home
$5,700,000
10/30/25
5
5
4,735
1445 Holts Grove Cir, Winter Park, FL
0.81
Single-Family Home
$2,700,000
10/02/25
5
5
4,489
575 Palmer Ave, Winter Park, FL
0.78
Single-Family Home
$2,650,000
10/24/25
6
5
4,767
940 Lincoln Cir, Winter Park, FL
0.77
Single-Family Home
$2,495,000
07/22/25
4
4.5
3,551

Nearby homes

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Assigned Schools

These are the assigned schools for 266 Chase Ave.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Park

At least 595 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there are sidewalks

  • 84 % Say car is needed

  • 79 % 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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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Explore by feature - Pet Friendly

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Homes for sale near 266 Chase Ave

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Off Market Homes Near 266 Chase Ave

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