2814 SHERIFF WAY, Winter Park, FL, 32792 | $574,900

Under contract-accepting backup offers. 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

  • Rooms: 9
  • Bedrooms: 4
  • Baths: 2 full
  • Laundry: In Garage
  • Style: Florida
  • Year Built: 1965
  • Heating: Central
  • Cooling: Central Air
  • Approx Sq. Feet: 1,948
  • Acreage: 0.18
  • Est. Taxes: $7,417
  • Middle School: Glenridge Middle
  • High School: Winter Park High
  • Pool: Gunite
  • Appliances: Disposal, Range, Refrigerator
  • MLS#: O6383098
  • Days on Market: 9 days
  • Website: https://www.raveis.com
    /prop/O6383098/2814sheriffway_winterpark_fl?source=qrflyer
This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this Site comes in part from the IDX Program of MFRMLS (My Florida Regional MLS DBA Stellar MLS). The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. (last updated 4/5/2026 4:47:06 PM)
Listing courtesy of CORCORAN PREMIER REALTY   Phone: 407-965-1155

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Melissa CohnRVP, Mortgage Banker, William Raveis Mortgage, LLC

NMLS Mortgage Loan Originator ID 16953

917.838.7300

Melissa.Cohn@raveis.com

Our Executive Mortgage Banker:

  • Is available to meet with you in our office, your home or office, evenings or weekends
  • Offers you pre-approval in minutes!
  • Provides a guaranteed closing date that meets your needs
  • Has access to hundreds of loan programs, all at competitive rates
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Pedro DelgadilloInsurance Sales Director, William Raveis Insurance

305.922.5393

Pedro.Delgadillo@raveis.com

Our Insurance Division:

  • Will Provide a home insurance quote within 24 hours
  • Offers full-service coverage such as Homeowner's, Auto, Life, Renter's, Flood and Valuable Items
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    Encompass, Travelers, Fireman's Fund, Middleoak Mutual, One Beacon and American Reliable

2814 SHERIFF WAY, Winter Park, FL, 32792

$574,900

Customer Service

William Raveis Real Estate

Phone: 888.699.8876

Contact@raveis.com

Melissa Cohn

RVP, Mortgage Banker

William Raveis Mortgage, LLC

Phone: 917.838.7300

Melissa.Cohn@raveis.com

NMLS Mortgage Loan Originator ID 16953

5/6 (30 Yr)
Adjustable Rate Conforming*
30 Year
Fixed-Rate Conforming
15 Year
Fixed-Rate Conforming
Loan Amount $459,920 $459,920 $459,920
Term 360 months 360 months 180 months
Initial Interest Rate** 5.875% 6.375% 5.500%
Interest Rate based on Index + Margin 8.125%
Annual Percentage Rate 6.357% 6.533% 5.794%
Monthly Tax Payment $618 $618 $618
H/O Insurance Payment $92 $92 $92
Initial Principal & Interest Pmt $2,721 $2,869 $3,758
Total Monthly Payment $3,431 $3,579 $4,468

* The Initial Interest Rate and Initial Principal & Interest Payment are fixed for the first and adjust every six months thereafter for the remainder of the loan term. The Interest Rate and annual percentage rate may increase after consummation. The Index for this product is the SOFR. The margin for this adjustable rate mortgage may vary with your unique credit history, and terms of your loan.

** Mortgage Rates are subject to change, loan amount and product restrictions and may not be available for your specific transaction at commitment or closing. Rates, and the margin for adjustable rate mortgages [if applicable], are subject to change without prior notice.

The rates and Annual Percentage Rate (APR) cited above may be only samples for the purpose of calculating payments and are based upon the following assumptions: minimum credit score of 740, 20% down payment (e.g. $20,000 down on a $100,000 purchase price), $1,950 in finance charges, and 30 days prepaid interest, 1 point, 30 day rate lock. The rates and APR will vary depending upon your unique credit history and the terms of your loan, e.g. the actual down payment percentages, points and fees for your transaction. Property taxes and homeowner's insurance are estimates and subject to change.