451 SHEPHERD AVE., Winter Park, FL 32789
OFF MARKET

$2,269,700

Trulia Estimate
  • 5 Beds
  • 4.5 Baths
  • 4,312 sqft (on 0.29 acres)

451 SHEPHERD AVE., Winter Park, FL 32789

Est. Refi. Payment $15,797/mo*
Refinance Your Home
Currently Off Market - Sold Nov 4, 2024 for $1,900,000

Home Value

Trulia Estimate
$2.27M
Since last month
Increased$44K (+2%)
Since last year
Increased$401K (+21.4%)
Since last sale
Increased$372K (+19.6%)
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 +89% in the last 10 years
MonthEstimated value
2026
August 2026$2.27M
August 2026$2.27M
July 2026$2.23M
June 2026$2.13M
May 2026$1.97M
April 2026$1.84M
March 2026$1.82M
February 2026$1.84M
January 2026$1.84M
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 LASBURY AVENUE, Winter Park, FL
0.17
Single-Family Home
$2,650,000
07/31/26
5
4
4,917
473 FLETCHER PLACE, Winter Park, FL
0.15
Single-Family Home
$3,000,000
05/15/26
5
5.5
4,296
1560 WOODLAND AVENUE, Winter Park, FL
0.37
Single-Family Home
$1,675,000
05/08/26
5
4.5
3,851
785 N PHELPS AVENUE, Winter Park, FL
0.30
Single-Family Home
$1,825,000
07/30/26
5
3.5
2,964
1571 LASBURY AVENUE, Winter Park, FL
0.20
Single-Family Home
$1,700,000
02/26/26
4
3
2,749
715 VIA BELLA, Winter Park, FL
0.53
Single-Family Home
$2,078,500
12/11/25
5
4
4,328
1871 TAYLOR AVENUE, Winter Park, FL
0.35
Single-Family Home
$1,500,000
03/16/26
4
4.5
3,401
1521 HARRIS CIRCLE, Winter Park, FL
0.24
Single-Family Home
$4,500,000
05/29/26
4
4.5
3,922
1831 MIZELL AVENUE, Winter Park, FL
0.40
Single-Family Home
$1,545,000
10/09/25
4
3.5
3,204
185 SYLVAN BOULEVARD, Winter Park, FL
0.33
Single-Family Home
$2,500,000
03/06/26
4
4.5
3,138

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
420 SYLVAN DRIVE, Winter Park, FL 32789
0.04
$1,238,500
3
3.5
2,676
Off Market
362 Sylvan Dr, Winter Park, FL 32789
0.08
$2,401,700
4
5.5
3,912
Off Market
412 FLETCHER PLACE, Winter Park, FL 32789
0.12
$1,113,300
3
3.5
3,146
Off Market
465 N PHELPS AVENUE LOT 27, Winter Park, FL 32789
0.07
$850,000
-
-
-
Recently Sold
520 SHEPHERD AVENUE, Winter Park, FL 32789
0.07
$2,952,200
4
4
4,587
Off Market
363 N PHELPS AVENUE, Winter Park, FL 32789
0.10
$1,189,700
4
3
2,871
Off Market
431 FLETCHER PLACE, Winter Park, FL 32789
0.15
$2,166,200
4
3.5
4,045
Off Market
473 FLETCHER PLACE, Winter Park, FL 32789
0.15
$3,000,000
5
5.5
4,296
Recently Sold
313 SYLVAN DRIVE, Winter Park, FL 32789
0.15
$5,500,000
4
4.5
4,775
For Sale
313L SYLVAN DRIVE LOT 10, Winter Park, FL 32789
0.15
$1,750,000
-
-
-
For Sale
313 SYLVAN DRIVE LOT 10, Winter Park, FL 32789
0.15
-
-
-
-
Off Market

Local Information

  • Map ViewExplore the area around 451 SHEPHERD AVE..
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2004
0.29 acre lot
4,312 sqft
$526/sqft
Garage

About this House

WOW!!! Repainted! Refinished Wood Floors, Refreshed Throughout!!! Wait until you see this transformation: Entire interior, freshly painted, hardwood floors refinished, new roof, new pool heater, new downstairs washer/dryer, professionally cleaned and staged! Master shower and marble floors replaced 2024... the list goes on and on. Like NEW - Move in ready! Stunning traditional home on a tree lined street in Olde Winter Park. Gorgeous custom trim, woodworking and architectural details such as coffered ceilings, French doors, plantation shutters throughout, beautiful Schonbeck crystal chandeliers. Open concept with soaring ceilings, gourmet chef's kitchen, wine room, salt water pool and spa. Fabulous large and spacious primary suite, with walk-in closet, including a washer/dryer. Tennessee flagstone and brick walkways offer peace and tranquility among mature landscaping. Outdoor covered areas including a summer kitchen and a brick fireplace.
451 SHEPHERD AVE., Winter Park, FL 32789 is a 5 bedroom, 5 bathroom, 4,312 sqft single-family home built in 2004. It last sold for $1,900,000 on Nov 4, 2024 (13% below the $2,195,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $2,269,700, with a rent estimate of $7,984/month.
Last check for updates: about 10 hours ago
Listed by Pamela Ryan, (407) 721-4541
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#O6179257
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 451 SHEPHERD AVE.

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Primary Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 5, Primary Bathroom, Bonus Room, Dining Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4312 Square Feet
Appliances & Utilities
Utilities: Electricity Available, Electricity Connected, Natural Gas Available, Natural Gas Connected, Sewer Available, Street Lights, Water ConnectedAppliances: Bar Fridge, Convection Oven, Dishwasher, Disposal, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Wine RefrigeratorDishwasherDisposalLaundry: Inside,Other,Upper LevelMicrowaveRefrigerator
Heating & Cooling
Heating: Electric,Heat Pump,ZonedHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Electric
Fireplace & Spa
Fireplace: Living RoomHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Shutters, Window TreatmentsDoor: French Doors, Outdoor Grill, Outdoor ShowerFlooring: Carpet, Marble, Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Marble, Tile, Hardwood
View
Has a ViewView: Pool
Security
Security: Security Gate, Security System, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Rear PorchFencing: FencedVegetation: Mature LandscapingExterior: Irrigation System, Lighting, Outdoor Grill, Outdoor Shower, Rain Gutters, SidewalkFoundation: SlabHas a 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,Garage Faces Rear,Parking Pad
Pool
Pool: Deck, Gunite, Heated, In Ground, Outside Bath Access, Salt WaterPool
Frontage
Responsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 231

Property Information

Year Built
Year Built: 2004
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: Block, StuccoNot a New ConstructionNot Attached PropertyNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 302205850300100

Price & Status

Price
List Price: $2,195,000
Status Change & Dates
Off Market Date: Fri Oct 04 2024Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

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

Building

Building Area
Building Area: 5686 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOA

Lot Information

Lot Area: 0.29 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6179257Showing Advance Notice: 24Showing AttendedShowing Considerations: See RemarksShowing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, Listing Agent Must AccompanyUniversal Property Id: US-12095-N-302205850300100-R-N

Price and Tax history

DateEventPrice
Nov 4, 2024
Source: Stellar MLS #O6179257
Sold
$1,900,000
Oct 4, 2024
Source: Stellar MLS #O6179257
Pending
$2,195,000
Jun 17, 2024
Source: Stellar MLS #O6179257
PriceChange
$2,195,000
Price decreased by 2%
Mar 25, 2024
Source: Stellar MLS #O6179257
PriceChange
$2,250,000
Price decreased by 2%
Feb 16, 2024
Source: Stellar MLS #O6179257
Listed For Sale
$2,300,000

Market trends in Winter Park

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$451K
$833MoM
Sale-to-List Price
98.0%
0.3%MoM
Price per sq ft
$287
$0MoM
Available listings
368
12MoM

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
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  • 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
    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
    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
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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. "
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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"
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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. "
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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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LGBTQ Local Legal Protections

Frequently asked questions about 451 SHEPHERD AVE.

  • What is 451 SHEPHERD AVE. estimated to be worth?
    Trulia's estimated value for 451 SHEPHERD AVE. in Winter Park, FL is $2,269,700.
  • What is the price history for 451 SHEPHERD AVE.?
    451 SHEPHERD AVE. in Winter Park, FL last sold for $1,900,000 in November 2024.
  • 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 $451K. That is down $833 from the prior month.
  • Does 451 SHEPHERD AVE. have air conditioning?
    Yes, 451 SHEPHERD AVE. in Winter Park, FL has air conditioning.
  • Does 451 SHEPHERD AVE. have a pool?
    Yes, 451 SHEPHERD AVE. in Winter Park, FL has a pool.

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

57 rentals with an outdoor space in Winter Park, FL

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