Winter Park Real Estate

Central Florida

Winter Park Real Estate

Looking for your Dream Home in Winter Park? Many homes are selling within days of being listed and we are able to see listings before they go public. So, send us your personal home specs and together we'll find your perfect home! 

About Winter Park, Florida

If strolling down a brick street and enjoying a latte while window shopping is your idea of paradise- consider Winter Park your dream come true.

Winter Park, Florida is a city in Orange County, FL. It’s recognized as the first centrally planned community in Florida. Promoted in the late 1800’s as a ‘refuge for the cultured and wealthy’ this city has done a wonderful job of maintaining the luxurious look and feel that it was developed to feature all of those decades ago.

Winter Park’s downtown area which covers the area around Park Avenue has public civic buildings, upscale retail stores, fine dining, art galleries, museums, a park, train station, golf course and country club, a historic cemetery, a beach boat launch and luxury downtown living.

Winter Park is celebrated for a sense of place and history, uncommon in many parts of Central Florida. Some of the structures and homes are more than 100 years old. The scenic Old Winter Park area is punctuated by small, winding brick streets, and canopy of old Southern Live Oak and Camphor trees. The city draws thousands of visitors to annual festivals including the Bach Festival, the nationally ranked Sidewalk Art Festival, and the Winter Park Concours d ’Elegance.

Winter Park Florida

Close to Downtown Orlando

Less than 10 miles from Downtown Orlando, about 30 minutes from the Orlando International Airport and 25-30 minutes from all the major attractions, Winter Park Florida is convenient to all the wonderful things to see in do in Central Florida. Winter Park is a quaint, tranquil city full of history and culture with many structures being more than 100 years old.

Nearby Hotels & Restaurants

Winter Park has many business hotels to accommodate it's visitors. Most of the hotels have convention centers equipped to hold conferences, parties, and wedding receptions. There is the historic Langford Resort Hotel, the Park Plaza Hotel, and the Best Western Mount Vernon Inn.

Winter Park also has a wonderful selection of restaurants for example: Houston's, P.F. Chang's China Bistro, Park Plaza Gardens, Brio Tuscan Grill, Luma's, Fleming's Prime Steakhouse & Wine Bar and don't forget Ruth's Chris Steakhouse just to name a few.

Filled with Natural Beauty

With over 70 parks Winter Park is home to beautiful landscapes and beautiful Florida greenery. If you ask most central Floridians to describe Winter Park one of the first things that will be shared is how lush and well maintained the cities common areas are. You can see the pride this city takes in their good reputation.

Close to Popular Shopping Districts

Park Ave. is greater Orlando’s premier shopping district where stores such as Lilly Pulitzer, Ann Taylor, and Tuni’s Boutique allow locals to find everything they could need… and more. This well-known street also offers wonderful dining options such as Prato and AVA Mediterranean . Whether you want to buy a Rolex or simply take a Sunday afternoon stroll down the avenue, people drive from far away to come and enjoy what Winter Park residents get to call home. Year round Winter Park hosts festivals and special events, the crown jewel function being the Winter Park Art Festival that is held in the spring. This festival attracts artists from across the country and in the fall the Winter Park Autumn Art Festival is specifically hosted for Florida artists. Rollins College sits on Lake Virginia and is one of the highest rated liberal arts colleges in the country. Another university, Full Sail College, is a world renowned school for entertainment technology.

Great for Golfers

If you are a golfer you are going to love living in Winter Park! You can play a historic 9 hole course at the North End of Park Ave. There is also an 18 hole course at Winter Park Pines. Both of these courses are owned and operated by the city. In 2022 Winter Park built a new Library and Events Center. It was designed by celebrity architect David Adjaye. This new eye-catching center can be rented for private functions and is a centerpiece of the city’s focus on beautiful design and architecture. The Winter Park ‘Chain Of Lakes’ is a boater’s paradise. From the water beautiful mansions and exquisite estates can be seen, in fact there are scenic boat tours that are open to the public. These water tours were voted one of the ‘top Central Florida activities’ to enjoy.

Schools Nearby

  • Killarney Elementary
  • Rollins College

Things To Do Nearby

  • Park Avenue Shopping
  • Morse Museum of Art
  • Winter Park Boat Tour
  • WP Farmers’ Market
  • Multitude of Parks and Gardens
  • Train Depot
  • Top Class Golf Course & Country Club

Winter Park Neighborhoods

Featured Listings

Winter Park FL Homes for Sale

181 Virginia

WINTER PARK , FL 32789

  • Status: Active
  • Price: $11,795,000.00
  • Square Feet: 11107
  • Bedrooms: 5
  • Bathrooms: 8
  • Price Per Square Foot: $1061.94
  • Listing Last Updated:

1210 Via Capri

WINTER PARK , FL 32789

  • Status: Active
  • Price: $7,370,000.00
  • Square Feet: 7374
  • Bedrooms: 6
  • Bathrooms: 7
  • Price Per Square Foot: $999.46
  • Listing Last Updated:

1001 Anchorage

WINTER PARK , FL 32789

  • Status: Active
  • Price: $7,250,000.00
  • Square Feet: 12781
  • Bedrooms: 5
  • Bathrooms: 7
  • Price Per Square Foot: $567.25
  • Listing Last Updated:

1761 Pinetree

WINTER PARK , FL 32789

  • Status: Active
  • Price: $6,650,000.00
  • Square Feet: 6133
  • Bedrooms: 5
  • Bathrooms: 6
  • Price Per Square Foot: $1084.30
  • Listing Last Updated:

1460 Via Tuscany

WINTER PARK , FL 32789

  • Status: Active
  • Price: $5,999,000.00
  • Square Feet: 10295
  • Bedrooms: 6
  • Bathrooms: 8
  • Price Per Square Foot: $582.71
  • Listing Last Updated:

2161 Sharon

WINTER PARK , FL 32789

  • Status: Active
  • Price: $5,566,500.00
  • Square Feet: 9473
  • Bedrooms: 5
  • Bathrooms: 7
  • Price Per Square Foot: $587.62
  • Listing Last Updated:

2228 Azalea

WINTER PARK , FL 32789

  • Status: Active
  • Price: $5,400,000.00
  • Square Feet: 6775
  • Bedrooms: 5
  • Bathrooms: 6
  • Price Per Square Foot: $797.05
  • Listing Last Updated:

1135 Lakeview

WINTER PARK , FL 32789

  • Status: Active
  • Price: $5,200,000.00
  • Square Feet: 6955
  • Bedrooms: 5
  • Bathrooms: 5
  • Price Per Square Foot: $747.66
  • Listing Last Updated:

421 Lakewood

WINTER PARK , FL 32789

  • Status: Active
  • Price: $4,995,000.00
  • Square Feet: 8083
  • Bedrooms: 5
  • Bathrooms: 9
  • Price Per Square Foot: $617.96
  • Listing Last Updated:

985 Lincoln

WINTER PARK , FL 32789

  • Status: Active
  • Price: $4,250,000.00
  • Square Feet: 4960
  • Bedrooms: 5
  • Bathrooms: 7
  • Price Per Square Foot: $856.85
  • Listing Last Updated:

Featured Closings

Recently Sold Homes in Winter Park Florida

260 Rippling

WINTER PARK , FL 32789

  • Status: Sold
  • Price: $635,000.00
  • Square Feet:
  • Bedrooms: 3
  • Bathrooms: 2
  • Price Per Square Foot:
  • Listing Last Updated:

1870 Carollee

WINTER PARK , FL 32789

  • Status: Sold
  • Price: $417,000.00
  • Square Feet:
  • Bedrooms: 3
  • Bathrooms: 2
  • Price Per Square Foot:
  • Listing Last Updated:

2697 Wright

WINTER PARK , FL 32789

  • Status: Sold
  • Price: $374,000.00
  • Square Feet: 1932
  • Bedrooms: 3
  • Bathrooms: 2
  • Price Per Square Foot: $193.58
  • Listing Last Updated:
Karen Arbutine

Karen Arbutine

Winter Park Florida Realtor


Contact our office today to embark on the journey of buying or selling a home in Winter Park, Florida. We offer complimentary consultations and valuations, providing you with valuable insights into the market and the potential value of your property.