275 E Webster Ave, Winter Park, FL 32789
OFF MARKET

275 E Webster Ave
Winter Park, FL 32789

  • 8 Beds
  • 7.5 Baths
  • 6,730 sqft (on 0.57 acres)

$4,511,400

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $22,944/mo*
Refinance Your Home

$4,511,400

Trulia Estimate
as of May 15, 2026
Est. Refi. Payment $22,944/mo*
Refinance Your Home
8 Beds
7.5 Baths
6,730 sqft
(on 0.57 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

One of downtown Winter Park's most beloved homes is for sale! Situated on half an acre, 2 blocks from Park Ave. on the Winter Park Golf Course, its welcoming wrap-around front porch is the perfect place to relax and take in the beauty. Inside, the spacious study and dining room both offer sweeping views of the sprawling front yard and golf course. Step into the kitchen and you'll find the heart of the home. Equipped with granite and teak counter tops, custom framed double-sized Sub Zero refrigerator, custom blue 6-burner + grill Professional Viking range, 8' x 5' island, walk-in pantry/mudroom and much more. The kitchen opens to the inviting family room and large gathering room with fireplace. Also found on the first floor is the spacious master suite with vaulted beamed ceilings, fireplace and French doors that open to the pool. Upstairs are 5 bedrooms, 4 of which have en suite bathrooms and one bedroom that is currently the game room with its vaulted ceilings and plenty of space to play. Included upstairs is the full-size laundry room with large, walk-in storage area. (There is also a washer/dryer hook-up in the master bathroom). The backyard hosts a 20' x 40' pool, pool bath, laundry room, generator that runs the entire home and covered porch that is the length of the home. The breezeway attaches to the over-sized 3-car garage and has an 800 square foot 2/1 apartment with private entrance. This one-of-a-kind home is perfect for large entertaining or cozy family gatherings.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 275 E Webster Ave

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: Central, OtherHeating Fuel: Other
Interior Details
Types of Rooms: Dining Room, Family Room
Fireplace & Spa
Fireplace
Levels, Entrance, & Accessibility
Floors: Tile, Other, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: Other
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1978Year Updated: 1988
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 2

Lot Information

Lot Area: 0.57 acres

Price History for 275 E Webster Ave

DatePriceEventSource
03/05/2020$2,895,000Sold
N/A
10/03/2019$3,100,000PendingAgent Provided
10/03/2019$3,100,000Listed For SaleAgent Provided
02/25/2019$3,100,000ListingRemovedAgent Provided
01/07/2019$3,100,000Listed For SaleAgent Provided
10/18/2013$1,165,600Sold
N/A
05/21/2013$1,139,800ListingRemovedAgent Provided
03/23/2013$1,139,800Listed For SaleAgent Provided
11/21/2012$1,261,000ListingRemovedAgent Provided
09/24/2012$1,261,000PriceChange
Agent Provided
08/09/2012$2,200,000PriceChange
Agent Provided
03/24/2012$1,990,000Listed For SaleAgent Provided
02/15/2012$2,490,000ListingRemovedAgent Provided
12/15/2011$2,490,000PriceChange
Agent Provided
10/19/2011$2,775,000PriceChange
Agent Provided
03/18/2011$2,890,000PriceChange
Agent Provided
01/22/2008$4,000,000Listed For SaleN/A
01/02/2003$1,175,000Sold
N/A
11/02/2000$980,000Sold
N/A
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Property Tax and Assessment

Year2024
Tax$39,330
Assessment$3,835,478
Home facts updated by county records

Comparable Sales for 275 E Webster Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
887 Georgia Ave, Winter Park, FL
0.13
Single-Family Home
$4,500,000
04/30/26
6
5.5
5,759
575 Palmer Ave, Winter Park, FL
0.28
Single-Family Home
$2,650,000
10/24/25
6
5
4,767
851 Georgia Ave, Winter Park, FL
0.11
Single-Family Home
$3,600,000
05/21/25
4
3.5
4,314
940 Lincoln Cir, Winter Park, FL
0.15
Single-Family Home
$2,495,000
07/22/25
4
4.5
3,551
421 Lakewood Dr, Winter Park, FL
0.47
Single-Family Home
$4,087,500
08/20/25
5
8
5,847
985 Lincoln Cir, Winter Park, FL
0.16
Single-Family Home
$4,599,000
05/28/25
5
6
3,660
1240 Harding St, Winter Park, FL
0.51
Single-Family Home
$5,125,000
11/07/25
5
5.5
6,708
1400 Alabama Dr, Winter Park, FL
0.49
Single-Family Home
$5,400,000
02/27/26
5
7
7,916
984 Mayfield Ave, Winter Park, FL
0.59
Single-Family Home
$4,750,000
05/27/25
4
5.5
4,913
266 Chase Ave, Winter Park, FL
0.61
Single-Family Home
$2,935,000
05/27/25
5
5.5
4,088

Assigned Schools

These are the assigned schools for 275 E Webster Ave.
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What Locals Say about Winter Park

At least 594 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 85 % Say car is needed

  • 84 % Say there are sidewalks

  • 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

Learn more about our methodology.
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Oviedohome
    "Need to drive to work. Can walk to local parks. Walking or biking other places does not feel so friendly even though there are restaurants and grocery stores nearby. There are two commuter train stations close by. "
    2
    Flag

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275 E Webster Ave, Winter Park, FL 32789 is a 8 bedroom, 8 bathroom, 6,730 sqft single-family home built in 1978. This property is not currently available for sale. 275 E Webster Ave was last sold on Mar 5, 2020 for $2,895,000. The current Trulia Estimate for 275 E Webster Ave is $4,511,400.