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Back 2814 Sheriff Way
Off Market

2814 Sheriff Way

Winter Park FL 32792

4
2
2
1948 sq. ft.
7797 sq. ft.
Single-Family
Last sold for $545,000
Angela CarneyAngela Carney, last sold this property on 22 April 2026 after 48 days on market.

Overview

Under Contract. Backup offers welcome.Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two bathrooms (both showers renovated 5/25) perfect for family living or entertaining guests. As you step inside, you'll be welcomed by a spacious living area that effortlessly transitions into the dining space, creating a warm and inviting setting for gatherings and family meals. The kitchen is thoughtfully designed for both functionality and efficiency, ready to cater to all your culinary needs. Additional living areas include a sunroom back porch and a screened-in carport, providing versatile spaces for relaxation or entertainment. The home is perfect for entertaining, with a rear sunroom/porch, pool, offering a personal oasis for unwinding or hosting friends and family. This outdoor retreat is destined to become a favorite spot for relaxation and enjoyment. The 2-car carport with a screen creates another space to entertain. Located just minutes from Cady Way Trail, Ward Park, Cady Way Community Pool, Lake Baldwin Dog Park, Winter Park Pines Golf Club, and the iconic Park Avenue, this home is perfectly positioned for both convenience and leisure.

Features

4 bedrooms
2 bathrooms
2 carspaces
2 carport spaces
1948 sq. ft. floor area
7797 sq. ft. lot size
Single-Family

Estimated Value

Based on this property and similar 4 bedroom single-family properties sold in Winter Park over the last 12 months, the estimated median property value of 2814 Sheriff Way is $545k.

Median value
$545k
Estimated value range
$298k - $1.5m
Median days on market
25
Estimated value trend
1%
increase over the last 12 months
Average days on market is based on recent, comparable sales in Winter Park. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 2814 Sheriff Way

2026
Sold
$545,000
22 Apr 2026 by Angela Carney, of CORCORAN PREMIER REALTY
2021
Sold
$380,000
15 Jul 2021 by Rex Hunter, of WEICHERT REALTORS HALLMARK PRO

Happy sellers in Winter Park

89%
89% of sellers in Winter Park reported that their sale price either exceeded or met their price expectations.

Winter Park stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 17 reviews in Winter Park over the last 12 months.

Local market activity for 4 bedroom single-family properties in Winter Park

In the last 12 months, 131 four-bedroom single-family properties similar to 2814 Sheriff Way, have been sold.

This represents a 14% increase in four-bedroom single-family properties sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Winter Park

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Abby Greenberg

Sellers who recommend Abby Greenberg have praised them for being local expert, supportive, clear communication, responsive, trustworthy, great negotiation, and reliable

  •   4.9   (44 reviews)
  •  2 Reviews in Winter Park
  •  2 Sales in Winter Park
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Jorge Martinez, Jr

Sellers who recommend Jorge Martinez, Jr have praised them for being clear communication, local expert, supportive, well-prepared, friendly, great negotiation, and hard-working

  •   5   (86 reviews)
  •  2 Reviews in Winter Park
  •  1 Sale in Winter Park
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Lisa Gould

Sellers who recommend Lisa Gould have praised them for being local expert, clear communication, supportive, responsive, patient, reliable, and empathetic

  •   5   (204 reviews)
  •  1 Review in Winter Park
  •  7 Sales in Winter Park
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Allison Day

Sellers who recommend Allison Day have praised them for being local expert, responsive, clear communication, supportive, patient, friendly, and empathetic

  •   5   (109 reviews)
  •  1 Review in Winter Park
  •  6 Sales in Winter Park
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