Sarasota's Premier Homes

Florida

2814 SHERIFF WAY

WINTER PARK , FL 32792

MLS#: O6383098

$574,900

Status: Active
Listing number: O6383098
Listing provided by: CORCORAN PREMIER REALTY
Listing agent phone: None
Last update: 43 minutes ago
New on site today
Browse Properties
WINTER PARK PINES - Residential

Property

Beds

4

Full Baths

2

1/2 Baths

None

Year Built

1965

Sq.Footage

1,948

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 & Amenities

Interior

  • Total Bedrooms

    4

  • Bathrooms

    2

  • Cooling YN

    YES

  • Cooling

    Central Air

  • Fireplace YN

    YES

  • Heating YN

    YES

  • Heating

    Central

  • Pet friendly

    N/A

Exterior

  • Garage

    No

  • Construction Materials

    Block

  • Other Exterior Features

    Rain Gutters

  • Patio and Porch Features

    Enclosed, Rear Porch, Screened

  • Pool

    Yes

  • Pool Features

    Gunite, Private

  • Waterfront YN

    NO

Area & Lot

  • Lot Size(acres)

    0.18

  • Property Type

    Residential

  • Property Sub Type

    Single Family Residence

  • Architectural Style

    Florida

Price

  • Sales Price

    $574,900

  • Tax Amount

    $7,417.27

  • Sq. Footage

    1, 948

  • Price/SqFt

    $295

HOA

  • Association

    No

School District

  • Elementary School

    Aloma Elem

  • Middle School

    Glenridge Middle

  • High School

    Winter Park High

Property Features

  • Stories

    1

  • Foundation Details

    Block

  • Ownership

    Fee Simple

  • Senior Community YN

    NO

  • Sewer

    Public Sewer

  • Tax Lot

    5

  • Water Source

    None

Schedule a Showing

Showing scheduled successfully.

<
>
IN PERSON
VIA CHAT

What is 3 + 4 ?


Change time

Mortgage calculator

Estimate your monthly mortgage payment, including the principal and interest, property taxes, and HOA. Adjust the values to generate a more accurate rate.

Your payment

Principal and Interest:

$

Property taxes:

$

HOA fees:

$

Total loan payment:

$

Total interest amount:

$

Location

County

Orange

Elementary School

Aloma Elem

Middle School

Glenridge Middle

High School

Winter Park High

Listing Courtesy of Angela Carney , CORCORAN PREMIER REALTY

RealHub Information is provided exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. RealHub website owner shall not be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

Agent Emil Garinga

Executive Assistant

Emil Garinga

Call Emil today to schedule a private showing.


* Listings on this website come from the FMLS IDX Compilation and may be held by brokerage firms other than the owner of this website. The listing brokerage is identified in any listing details. Information is deemed reliable but is not guaranteed. If you believe any FMLS listing contains material that infringes your copyrighted work please click here to review our DMCA policy and learn how to submit a takedown request.© 2024 FMLS.
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.

2814 SHERIFF WAY

Message successfully sent.

What would you like to know?

What is 3 + 4 ?

Related Properties

One or more photo(s) has been virtually staged. Welcome to 2809 Casa Aloma — a beautifully updated 3-bedroom, 2-bath charming home located on a quiet cul-de-sac in desirable Winter Park. Originally one of the subdivision’s model homes "Monaco", this property blends French Provincial design with extensive modern upgrades. Major improvements include a 2021 Architectural roof, 2019 A/C system, 2021 Series 4000 double hung double pane hurricane impact windows with built in screens/tinting, upgraded gas meter for generator, Culligan high efficiency water softener, 2022 gas water heater, 2021 vinyl fencing, Comfort A34 jacuzzi hot tub, Ring security devices transferrable, and a Generac 24000 standby natural gas whole-house generator 2022 — providing efficiency and peace of mind. The renovated interior features a bright, functional layout and a natural gas range in the updated kitchen, Bathrooms with Moen All in One Spa. Enjoy Florida living year-round from the large covered back porch overlooking a fully fenced backyard with low-maintenance artificial turf, Jacuzzi, and storage shed. The oversized two-car garage adds convenience and additional storage. Ideally located just minutes from the shopping and dining of Park Avenue, outdoor recreation at Kraft Azalea Garden, and cultural attractions including the Charles Hosmer Morse Museum of American Art. Convenient access to Advent Health Winter Park and nearby commuter routes make this location as practical as it is desirable. Experience the comfort of a move-in ready home in one of Central Florida’s most established and sought-after communities. Ring security system is active on the exterior and has audio/visual capabilities.
#O6379719

WINTER PARK

2809 CASA ALOMA WAY

3 Beds

2 Baths

1,627 Sq.Ft.

$499,000

MLS#: O6379719

One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just one mile from Park Avenue, SunRail, and Rollins College, and only half a mile from Hannibal Square, local parks, and the Winter Park Library, this property offers an unbeatable blend of convenience, walkability, and lifestyle. As you step inside, you are greeted by a modern open floor plan enhanced with luxury vinyl plank flooring that flows seamlessly throughout the home. The spacious living and dining areas create an inviting environment ideal for both everyday living and entertaining. The updated kitchen serves as the heart of the home, featuring stainless steel appliances, granite countertops, and timeless white shaker cabinetry. Its thoughtful layout allows for easy conversation and connection while preparing meals, making it as functional as it is stylish. The oversized great room provides flexibility for relaxing, hosting guests, or creating a dedicated workspace. Both bedrooms are generously sized, offering comfort and versatility. The owner’s bedroom is especially appealing, complete with a custom closet organizer and direct access to a private paver patio—an ideal setting to enjoy Florida’s year-round sunshine. The bathroom has been tastefully updated with granite countertops and a shower/tub combination accented by classic white subway tile, creating a clean and timeless aesthetic. Outdoors, the secluded backyard offers privacy and future potential, with room to expand or customize according to your vision. Whether you are searching for a primary residence, a downsizing opportunity, or an investment in the heart of Winter Park, this property presents a rare chance to own a beautifully updated home in a prime location. Experience the charm, convenience, and lifestyle that 1036 Aragon Avenue has to offer. Schedule your private showing today.
#O6382491

WINTER PARK

1036 ARAGON AVENUE

2 Beds

1 Baths

1,073 Sq.Ft.

$525,000

MLS#: O6382491

Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed floor plan provides generous living spaces, well-proportioned bedrooms, and an effortless flow for everyday living and entertaining. Located just minutes from Winter Park’s renowned shopping, dining, parks, and top-rated schools, this home presents an exceptional opportunity to enjoy low-maintenance living in one of Central Florida’s most desirable neighborhoods.
#O6381195

WINTER PARK

1781 INDIANA AVENUE A

3 Beds

2 Baths

1,616 Sq.Ft.

$575,000

MLS#: O6381195

STUNNING 6-BEDROOM HOME FOR SALE: 2600 Euston Rd, Winter Park, FL 32789 Imagine yourself in this gorgeous 6-bedroom, 3-bath home, perfectly situated in a desirable Winter Park neighborhood! With 3,145 sqft of living space, this property offers endless possibilities for large families, multi-generational living, or those who love to entertain. Spacious Layout: 6 bedrooms, 3 bathrooms, and plenty of room to spread out, Updated Amenities: Modern kitchen, fresh finishes, and abundant natural light, Outdoor Oasis: Private backyard with mature trees, perfect for relaxation or gatherings, Prime Location: Close to parks, top-rated schools, and downtown Winter Park's shops and dining, 2021 ROOF Whether you're looking for a forever home or an investment opportunity, this property ticks all the boxes. Shedule your private showing today and make this stunning home yours.
#O6380534

WINTER PARK

2600 EUSTON ROAD

6 Beds

3 Baths

3,145 Sq.Ft.

$650,000

MLS#: O6380534

Welcome home to the charm and character of the bygone days. This 3-bedroom, 2-bathroom home offers 2,556 square feet, with the historic main home originally built in 1922. Featuring original antique wood floors, a classic fireplace, and a one of a kind upstairs loft, there's nothing quite like it! A charming front porch welcomes you into the living room with a fireplace. A front room currently used as a formal parlor or sitting room doubles as the third bedroom, also ideal for entertaining or reading. Two additional bedrooms and full baths are located down the hall. The dining room sits just off the main living space, with French doors opening into the hallway. The kitchen is positioned toward the back of the home with a tucked away laundry closet. Accessed by an interior staircase off the kitchen, the HIGHLIGHT of the home is the handcrafted upstairs loft with design in a class of itself. Currently used as an exquisite billiards room and library, this flexible space can serve as a library, office, or creative retreat, and features a balcony with views of Lake Killarney. Additional features include 42-inch kitchen cabinets, stone countertops, a roof replaced in 2018, AC replaced in 2019. Wind mitigation passed April 2024, septic pumped October 2025, and on top of it all, no HOA! Conveniently located minutes from Downtown Winter Park, Park Avenue, Rollins College, and just minutes from I-4, this is a truly unique property offering craftsmanship and character rarely found today.
#O6379543

WINTER PARK

1951 STAUNTON AVENUE

3 Beds

2 Baths

2,556 Sq.Ft.

$599,000

MLS#: O6379543

Charming Mid-Century Winter Park bungalow with tremendous potential * Not ready to build a new home but would like to have that option someday? This property provides the unique opportunity of being move-in ready and not overvalued for the neighborhood * The majority of the homes on this quiet tree lined street are brand new or recently built. There is value in being one of the only remaining homesites to be rebuilt * Ready to either owner-occupy or lease ($2,095 per month lease just completed) while you take the appropriate amount of time to create your custom plans. Step inside to find beautiful, exposed hardwood floors with timeless warmth and elegance, while the updated kitchen and baths ensure the home is move-in ready for your convenience. The large, fenced backyard offers plenty of room for outdoor living, providing the perfect spot to relax or entertain * The carport features a laundry/storage area, adding even more functionality to the property * House has a durable metal roof, further enhancing its appeal and longevity. For those looking to create a custom masterpiece, the existing structure offers the option for redevelopment, allowing you to build a home that perfectly suits your vision * Owner painted the exterior, replaced the microwave and hot water heater last year * Located just off N Park Avenue and a short distance from Winter Park's main attractions, you'll enjoy proximity to Downtown Winter Park, Winter Park Farmers Market, Whole Foods, Winter Park Village, and Rollins College. Shopping, dining, and entertainment are all just moments away, making this an unbeatable location * Don’t miss the chance to make this rare find your own! Currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School *
#O6379388

WINTER PARK

1137 OAKS BOULEVARD

2 Beds

1 Baths

1,149 Sq.Ft.

$644,900

MLS#: O6379388

Welcome to 2052 Leanne Ct, a home that exudes warmth and elegance. The living room is graced with a cozy fireplace, perfect for those chilly evenings. The kitchen is a chef's dream, boasting all stainless steel appliances for a sleek, modern look. The primary bedroom is a haven of comfort with double closets for ample storage. The primary bathroom is a sanctuary with double sinks, providing ample space for your morning routine. The fenced-in backyard provides a private outdoor space for relaxation and entertainment. The home has been recently updated with fresh interior and exterior paint, giving it a clean, refreshed look. New flooring throughout the home adds a touch of sophistication and durability. The new appliances ensure efficiency and convenience. Included 100-Day Home Warranty with buyer activation
#O6379323

WINTER PARK

2052 LEANNE COURT

4 Beds

2 Baths

2,264 Sq.Ft.

$461,000

MLS#: O6379323

Price reduced
Easy access to all of Winter Park, UCF, and south Seminole County from this convenient, central location! If you've been searching for a spacious pool home with plenty of space for playing, entertaining, or even working from home -- you've found it here! When you walk in, you'll appreciate the intuitive flow of living space into the kitchen, with built-in eating space. Off of the kitchen, you'll find a bonus space (perfect for an office or home gym) as well as a large indoor laundry room/mudroom, and the converted garage which is ideal for a playroom or secondary living space. On the other side of the home, 2 secondary bedrooms, an oversized hall bathroom, and a primary with en suite bath. There are additional touches that go a long way, too, including the custom plantation shutters throughout the home and updated countertops in the kitchen. Much of your time will be spent in the backyard, enjoying a fenced in pool, screened porch, new custom shed (2025), and fully fenced yard with turf play area. Systems in the home have been well maintained: roof (2017), HVAC (2017), tankless gas water heater (2018), and brand new electrical updates (2026). The home was also re-plumbed in 2008.
#O6362285

WINTER PARK

3207 LOWNDES DRIVE

3 Beds

2 Baths

2,028 Sq.Ft.

$499,000

MLS#: O6362285

Price reduced
Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has a beautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 square feet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that create an open, airy feel throughout. The kitchen showcases elegant granite counters and modern stainless steel appliances. Hard flooring flows through the main living areas, offering both style and easy maintenance. Solar panels on the home save you hundreds each month on electricity. Seller is willing to pay $10000 towards solar pay off. Step outside to your private backyard oasis with a screened-in pool and jacuzzi spa, ideal for year-round Florida living. The fully vinyl fenced yard provides privacy and security for families and pets. This move-in ready property means you can start enjoying your new home immediately. The location offers incredible convenience with easy access to Winter Park shopping, restaurants, and world-famous theme parks. Major roads are nearby, making commuting simple whether you work locally or need to travel throughout Central Florida. The gated community adds security and peace of mind. Winter Park is known for its charming downtown area, excellent schools, and beautiful parks. This neighborhood combines suburban tranquility with urban accessibility, giving you the best of both worlds. Schedule your showing today!
#O6377988

WINTER PARK

5275 PINE LILY CIRCLE

5 Beds

3 Baths

3,152 Sq.Ft.

$665,000

MLS#: O6377988

- property

Send a message

Message successfully sent.

Your message

What is 3 + 4 ?

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to take the next step with this property? We can help you schedule a showing or virtual tour, or send you more details.

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Lucy - Your AI-Powered Realtor

Update Your Temporary Password

Personalize your search

Enter your email and we'll notify you immediately when new listings match what you're looking for.

or enter email address

Already have an account ? Login here

Continue your home search

Already have an account ? Login here

We use cookies

We use cookies primarily for analytics to enhance your experience. By accepting, you agree to our use of these cookies. You can manage your preferences or learn more about our cookies policy.

Privacy Policy Terms of Service