520 SHEPHERD AVENUE, Winter Park, FL 32789
OFF MARKET

520 SHEPHERD AVENUE
Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 4,587 sqft (on 0.43 acres)

$2,959,300

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $20,432/mo*
Refinance Your Home

$2,959,300

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $20,432/mo*
Refinance Your Home
4 Beds
4 Baths
4,587 sqft
(on 0.43 acres)

Local Information

  • Map ViewExplore the area around 520 SHEPHERD AVENUE.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1989
Lot Size
0.43 acres
Living Area
4,587 sqft
Price/Sqft
$645
Parking
2 Car Garage
HOA
None

About this House

This gracious estate is situated on a pristine 1/2 acre private lot just minutes to Park Avenue’s upscale boutiques & restaurants. As you enter this exquisite home you notice the light & bright open floor plan perfect for family living & entertaining. The fabulous chef’s kitchen has beautiful custom cabinets, Sile stone countertops, Thermador appliances including a 48” gas cooktop w/ pot filler, refrigerator, double ovens, microwave, 2 dishwashers & a large center island w/ prep sink. The expansive Great Room has a fireplace & French Doors . The Family Room is open to the kitchen w/ a cozy fireplace & French doors. There is a private office-den & fabulous walk-in temperature controlled wine room. The floor plan has 2 dining areas . The downstairs guest suite would be ideal for elderly parents or a 2nd master. Upstairs the exquisite & spacious Owners' Suite was recently renovated w/ 2 walk-in closets. Owners' spa bath has dual sinks, a soaking tub & large separate shower. There are 2 additional bedroom en suites upstairs & a laundry room. As you walk outside expect to be impressed by the spacious private park-like setting w/ masonry wall, classic open pool w/ firepit & fountains, a large screened & covered lanai & a sport court w/ reg. basketball. Add'l features: New: Roof, Windows, AC, Master Suite, Generator, electric charging station, ext. paint & flooring.
520 SHEPHERD AVENUE, Winter Park, FL 32789 is a 4 bedroom, 4 bathroom, 4,587 sqft single-family home built in 1989. It last sold for $2,600,000 on Feb 2, 2024 (2% below the $2,649,000 asking price). It is currently off market. The Trulia Estimate is $2,959,300, with a rent estimate of $7,587/month.

Home Details for 520 SHEPHERD AVENUE

Interior Features

Interior Details
Number of Rooms: 12Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Master Bathroom, Balcony Porch Lanai, Dining Room, Family Room, Kitchen, Laundry, Living Room, Office
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 4587 Square Feet
Appliances & Utilities
Utilities: Cable Connected, Electricity Connected, Fire Hydrant, Natural Gas Connected, Sewer Connected, Sprinkler Well, Street Lights, Underground Utilities, Water ConnectedAppliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Gas Water Heater, Microwave, Refrigerator, Tankless Water Heater, Washer, Water Filtration SystemDishwasherDisposalDryerLaundry: Inside,Laundry Room,Upper LevelMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Electric,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family Room, Living Room, Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Aluminum Frames, Blinds, Double Pane Windows, Drapes, Insulated Windows, Rods, Window Treatments, Wood FramesDoor: French DoorsFlooring: Brick/Stone, Carpet, Ceramic Tile, Marble, Vinyl
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Brick Stone, Carpet, Ceramic Tile, Marble, Vinyl
View
No View
Security
Security: Security Lights, Security System Leased, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: Membrane ShinglePatio / Porch: Covered, Porch, Rear Porch, ScreenedFencing: Fenced, Masonry, OtherVegetation: Mature LandscapingExterior: Irrigation System, Lighting, Private Mailbox, Rain GuttersFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Electric Vehicle Charging Station(s),Garage Door Opener
Pool
Pool: Gunite, In Ground, Pool SweepPool
Frontage
Road Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 3

Property Information

Year Built
Year Built: 1989
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Other
Building
Construction Materials: Other, Stucco, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 052230252800090

Price & Status

Price
List Price: $2,649,000
Status Change & Dates
Off Market Date: Sun Oct 29 2023

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER PARKCommunity: ETHEL PARK
School Information
Elementary School: Lakemont ElemJr High / Middle School: Maitland MiddleHigh School: Winter Park High

Building

Building Area
Building Area: 5695 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.43 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6150259Showing Advance Notice: 24Showing AttendedShowing Considerations: Pet(s) on PremisesShowing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must Accompany, ShowingTimeUniversal Property Id: US-12095-N-052230252800090-R-N
Last check for updates: about 12 hours ago
Listed by Shelley Heistand, (407) 718-9222
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Dan Haber, (321) 624-0966
PREMIER SOTHEBY'S INTL. REALTY, (407) 644-3295
Bought with: Abby Nelson, (407) 571-1445, RE/MAX 200 REALTY, (407) 629-6330
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6150259
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 520 SHEPHERD AVENUE

DatePriceEventSource
02/02/2024$2,600,000Sold
Stellar MLS #O6150259
11/01/2023$2,649,000PendingStellar MLS #O6150259
10/26/2023$2,649,000Listed For SaleStellar MLS #O6150259
08/29/2017$1,300,000Sold
N/A
07/26/2017$1,400,000PendingAgent Provided
06/23/2017$1,400,000PriceChange
Agent Provided
03/15/2017$1,475,000Listed For SaleAgent Provided
10/26/2016$1,475,000ListingRemovedAgent Provided
07/27/2016$1,475,000PriceChange
Agent Provided
07/13/2016$1,499,000PendingToActiveAgent Provided
07/12/2016$1,499,000PendingAgent Provided
06/20/2016$1,499,000Listed For SaleAgent Provided
09/23/2010$1,694,900ListingRemovedAgent Provided
08/06/2010$1,694,900PriceChange
Agent Provided
02/04/2010$1,495,000Listed For SaleAgent Provided
10/13/2005$1,800,000Sold
N/A

Market trends in Winter Park

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$452K
$7.33KMoM
Sale-to-List Price
97.7%
0.2%MoM
Price per sq ft
$288
$1MoM
Available listings
380
7MoM
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Property Tax and Assessment

Year2024
Tax$18,339
Assessment$2,093,952
Home facts updated by county records

Comparable Sales for 520 SHEPHERD AVENUE

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1630 LASBURY AVENUE, Winter Park, FL
0.11
Single-Family Home
$2,650,000
07/31/26
5
4
4,917
473 FLETCHER PLACE, Winter Park, FL
0.19
Single-Family Home
$3,000,000
05/15/26
5
5.5
4,296
1571 LASBURY AVENUE, Winter Park, FL
0.15
Single-Family Home
$1,700,000
02/26/26
4
3
2,749
1521 HARRIS CIRCLE, Winter Park, FL
0.31
Single-Family Home
$4,500,000
05/29/26
4
4.5
3,922
1871 TAYLOR AVENUE, Winter Park, FL
0.28
Single-Family Home
$1,500,000
03/16/26
4
4.5
3,401
641 BONITA DRIVE, Winter Park, FL
0.18
Single-Family Home
$4,800,000
01/02/26
5
5
6,699
1445 HOLTS GROVE, Winter Park, FL
0.56
Single-Family Home
$2,700,000
10/02/25
5
5
4,489
785 N PHELPS AVENUE, Winter Park, FL
0.23
Single-Family Home
$1,825,000
07/30/26
5
3.5
2,964
446 ALBERTA DRIVE, Winter Park, FL
0.38
Single-Family Home
$1,600,000
04/22/26
4
2.5
3,263
1560 WOODLAND AVENUE, Winter Park, FL
0.32
Single-Family Home
$1,675,000
05/08/26
5
4.5
3,851

Nearby homes

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Assigned Schools

These are the assigned schools for 520 SHEPHERD AVENUE.
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 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
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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
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  • 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
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  • 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
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  • 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
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  • 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

132 pet-friendly rentals in Winter Park, FL

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Homes for sale near 520 SHEPHERD AVENUE

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Off Market Homes Near 520 SHEPHERD AVENUE

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