Winter Park Homes For Sale, Condos For Sale & Orlando Real Estate

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The City of Gracious Living

Winter Park, Florida, known as the “City of Gracious Living,” boasts all the charm you might hope for in a city suburb. Unlike the name might suggest, the area doesn’t really experience much in the way of “winter weather,” but its nickname surely does it justice. It’s a great area for families, couples or single working folk alike. The art scene has no competition and the healthy Floridian lifestyle runs through the neighborhood’s many parks.

Winter Park Real Estate

The area’s close proximity – only about seven miles – to Downtown Orlando makes it one of Florida’s most desirable neighborhoods. Homes prices range from the most affordable in the $100,000s to multi-million dollar luxury estates. No matter what you’re looking for, you’ll likely find it in Winter Park.

The variety of outdoor spaces makes Winter Park real estate a great investment. Lake Virginia sits at the heart of the region and provides great opportunity for waterfront living – something most Floridians dream of.

From large homes found on the Winter Park Chain of Lakes to smaller homes providing a convenient location, there’s a little bit of everything in Winter Park. The 32789 and 32792 zip codes are known as the most desirable in Winter Park, along with the Windsong community.

Finding Your Dream Home in Winter Park

The 32789 zip code covers a large area of Winter Park with many homes found throughout. Homes throughout this zip code are known as some of the most desirable with many that are waterfront. They sell for an average home price of about $375K.

The 32792 zip code found in Winter Park provides more affordable homes. The average home price throughout this area is only $116K. However, some of the waterfront homes and larger luxury homes can go for more than $1 million.

Found in the center of Winter Park, the Windsong community circles Lake Mizell with access to both Lake Berry and Lake Virgina. Within the community, residents enjoy two community swimming pools, a beautiful clubhouse, and private boat docks to avoid the crowds.

This particular portion of Winter Park also has quite a charming history. The area was established after Charles Hosmer Morse – a Winter Park icon remembered by the Morse Museum – built the Windsong estate in 1904. A bell was hung from one of the trees outside and after all the neighbors followed suit, chimes and bells sung through the area, giving the charming community its name. It’s also very close to the famous Park Avenue found in Winter Park’s downtown area.

Our team has expert advice on all Winter Park real estate! Contact them with all of your Winter Park or Orlando real estate questions.

Living and Working in Winter Park

Winter Park features a very beautiful downtown area with plenty of restaurants, museums and shops. The tree-covered cobblestone streets and popular parks make it a very desirable area in Central Florida. Central Park is the most popular of the parks with plenty of outdoor activities for residents to enjoy along the trendy Park Avenue.

Winter Park is ranked #12 out of 324 of the best suburbs to live in all of Florida. It’s great for raising a family and the public schools are well regarded. The vast numbers of parks create a spacious living environment and nearby colleges encourage students of any grade level to pursue a great Florida education.

The area is also a great suburb for working professionals with jobs based in and around Orlando since commute times aren’t overwhelming. City nightlife is close by, but there are enough things to do in the neighborhood that it’s not necessary to travel outside of the area.

The art scene in Winter Park is incomparable to much of the surrounding area. The list of attractions in the area contains museums like the Cornell Fine Arts Museum and the Winter Park Historical Museum. There are a total of nine museums and art galleries in the area, complimented by the 32 that can be found nearby in Orlando.

Orlando and its surrounding areas – like Winter Park – are known for being a melting pot of cultures. Combine that fact with the close proximity to the ocean and there are sure to be some delectable eateries nearby. Winter Park Fish Company combines a Floridian culture with the freshness the coast has to offer. It gives residents an impeccable dining experience. The menu varies from pink shrimp tacos to raw oysters on the half shell. You can even have your favorites delivered to your beautiful Winter Park home.

Winter Park is a nature lover’s paradise. The neighborhood features over 70 different parks, some of which contain access to the Winter Park chain of lakes. Lake Baldwin Park sits at the northern edge of Lake Baldwin. It’s a great space to take family, friends, and even Fido. In the 23-acre park, dogs are allowed to be off-leash to run through the water, a tolerance most city parks don’t allow. Pack up the whole family for a picnic on the beach or launch your boat off the dock for a day in the water.

Park Avenue is the most popular stretch of shops, restaurants and entertainment found in Winter Park. More than 100 shops are found within 10 blocks, with all kinds of unique boutiques. The area also features many sidewalk cafes, hidden courtyards and Central Park.

Along with Park Avenue, many other shopping and dining options are found throughout the Winter Park Village area. Residents also enjoy easy access to the Charles Hosmer Morse Museum of American Art, which houses the largest collection of Tiffany glass in the world.

Winter Park is well known for the many events held throughout the year, as well. From the Sidewalk Art Festival to the Exotic Car Show, many events provide plenty of fun throughout the year.

Rollins College is found on the shores of Lake Virginia in Winter Park. It’s the oldest institution of higher education found in Florida and one of the top-rated private liberal arts colleges in the entire country. The college is also home to the Cornell Fine Arts Museum and the Bach Festival Choir.

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7821 Chediston Cir Orlando, FL 32817

$249,900 - 3Br/2Ba -  for Sale in Meadows Of Chickasaw, Orlando
New
$249,900
3 Beds
2 Baths
1,235 SqFt
Status Active
MLS # O5728642
Property Type Single Family Residence
BRAND NEW CONSTRUCTION 2018, perfect for first time home buyers or investors. 3 Bedroom/2 Bath , open plan with luxury upgrades, such as granite countertops, stainless steel appliances, remote control garage, oversized walk-in closet in master bedroom and title throughout the whole house, to name a few. The property is located a few minutes from UCF, Waterford Lakes Town Center, Highways 417 and 408, shopping and restaurants. Don't miss this opportunity, this lovely home can be yours.

2533 Leeward Way Winter Park, FL 32792

$209,900 - 3Br/2Ba -  for Sale in Windward Square Sec 2, Winter Park
New
$209,900
3 Beds
2 Baths
1,467 SqFt
Status Active
MLS # O5734743
Property Type Townhouse
Fabulous renovated townhome located in the highly sought after community of Windward Square in Winter Park. Just minutes away from Top Rated Seminole County Schools. This modern 3br/2ba property has a bright open floor plan with New Laminate Wood Floors, New Porcelain Tile Floors, New Light Fixtures, New Front Door with Glass Inserts, New Interior/Exterior Paint, NEW A/C(2018), New Pipes(2018) and New Electrical Panel(2018). The modern kitchen boasts of maple wood cabinets, granite counter tops, new stainless steel appliances, an island and a breakfast bar. The spacious dining room/family has a sliding glass door that leads out to a large screened porch with a fenced in back yard. The master bedroom has a large walk-in closet, a remodeled en suite with dual sinks and a step-in shower. The HOA dues include community pool, community tennis courts, playground and ground maintenance.

1602 Alabama Dr #405 Winter Park, FL 32789

$995,000 - 3Br/3Ba -  for Sale in Alabama Condo, Winter Park
New
$995,000
3 Beds
3 Baths
2,860 SqFt
Status Active
MLS # O5733899
Property Type Condominium
“Penthouse” unit at The Alabama first time available for purchase since original hotel to condo conversion completed in 1981... Originally 3 units (403, 404 & 405) now all combined as one but can easily be split back into two units. This is the ONLY unit in The Alabama with an outside terrace that is a really special feature! This building has a lakefront dock with boat slips available on Lake Maitland (Chain of Lakes)... The unit has tremendous potential to remodel and personalize with whatever lifestyle layout and features a buyer desires… Spacious, open living spaces and extensive windows/doors to create walls of windows and bright decor... This unit offers scenic, tree top, tranquil views of Lake Maitland and The Alabama’s beautiful expansive grounds... The unit also comes with 2 assigned covered parking spaces… There is a community club house & wonderful pool area... Several units have been completely remodeled and updated to a current modern style and are fabulous... You are in walking distance to Kraft Azalea Gardens on Lake Maitland and downtown Winter Park -- Park Ave shops, restaurants, etc... Truly a one of a kind complex & opportunity in premier location & setting!

159 Scottsdale Sq #159 Winter Park, FL 32792

$72,000 - 1Br/1Ba -  for Sale in Winter Park Woods Condo, Winter Park
New
$72,000
1 Bed
1 Bath
785 SqFt
Status Active
MLS # O5733902
Property Type Condominium
WINTER PARK WOODS CONDO! 1st Floor Unit, 785 Square feet, 1 bedroom with 2 closets, 1 bathroom with shower . Ceramic Mexican tile throughout. Spacious living room, and Sliding door to patio. Community amenities include pool, tennis courts, and playground. Amazing location near Full Sail University, UCF, Valencia College, the Orlando International airport and lots of restaurants and shopping. Nearby Baldwin Park, Winter Park trail, Winter Park village and Park Ave.

115 Palmer Ave Winter Park, FL 32789

$4,750,000 - 4Br/5Ba -  for Sale in Macdonald Robert Dhu Pk, Winter Park
New
$4,750,000
4 Beds
4.5 Baths
9,838 SqFt
Status Active
MLS # O5734401
Property Type Single Family Residence
Location Location Location! This is your opportunity to own this stunning Winter Park Estate just a short and beautiful walk to Park Avenue and everything it has to offer. The majestic residence sits on 1.5 acres and has over 280'on the enchanting Winter Park chain of lakes (Lake Maitland) The home boasts gorgeous lake views from most rooms, a lovely sprawling private master suite, formal living with a wood burning fireplace, elegant entrance, great kitchen for entertaining guest who want to see the lake views from the newly enclosed sun room. Over sized backyard with pool, open porch area, outdoor shower, impeccable landscaping throughout the yard & recently updated boat house.

1602 Alabama Dr #403 Winter Park, FL 32789

$495,000 - 2Br/2Ba -  for Sale in Alabama Condo, Winter Park
New
$495,000
2 Beds
2 Baths
1,016 SqFt
Status Active
MLS # O5733919
Property Type Condominium
“Penthouse” unit at The Alabama first time available for purchase since original hotel to condo conversion completed in 1981... Originally 3 units (403, 404 & 405) now all combined as one but can easily be split back into two units. The unit has tremendous potential to remodel and personalize with whatever lifestyle layout and features a buyer desires… This unit offers scenic, tree top, tranquil views of Lake Maitland and The Alabama’s beautiful expansive grounds... This building has a lakefront dock with boat slips available on Lake Maitland (Chain of Lakes)... The unit also comes with 1 assigned covered parking space… There is a community club house & wonderful pool area... Several units have been completely remodeled and updated to a current modern style and are fabulous... You are in walking distance to Kraft Azalea Gardens on Lake Maitland and downtown Winter Park -- Park Ave shops, restaurants, etc... Truly a one of a kind complex & opportunity in premier location & setting!

106 S Interlachen Ave #118 Winter Park, FL 32789

$950,000 - 2Br/2Ba -  for Sale in Cloisters Condo, Winter Park
New
$950,000
2 Beds
2 Baths
1,706 SqFt
Status Active
MLS # O5734068
Property Type Condominium
Dream come true! Downtown Winter Park 3BR/2BA home (Currently staged as a large 2 bedroom w/ private den) Walk to Park Avenue Restaurants, Shops, Museums, Golf Course, etc. REMODELED 1st floor Lakefront condo w/ unobstructed Lake Osceola views from your unit & porch. Beautifully re-designed custom for a distinguished Winter Park interior designer & never lived in. Perfectly situated end unit, this feels like a single residence. Enter through front door or “private” garden entrance. Covered parking & lots of convenient street parking. Open, light & bright w/ all the most updated modern amenities. New open kitchen w/ top-of-the-line appliances, granite counters & floors, custom 3/4” inch solid wood cabinetry & graphic tile back splash. The expansive dining room is open to the gracious living room featuring a chic marble trimmed wood burning fireplace & over 20’ of new tinted sliding doors w/ lake views. Upgrades include: Hardwood Flooring, 9 ft. ceilings, Crown Molding, Custom Cabinetry & high-end finishes in both Bathrooms & in Oversized Laundry Room with New Full Size Washer & Dryer, Upgraded Plumbing, Electrical, New Water Heater, New Doors, New hardware & more. The Cloisters offers amenities including heated pool set amidst manicured gardens, clubhouse, brand new boat dock & slips, putting green, & on-site management. Just a few steps from Alfond Inn, Rollins College & the Sunrail/Amtrak station for a quick commute to Orlando top hospitals, etc.

3651 N Goldenrod Rd #210 Winter Park, FL 32792

$93,500 - 2Br/2Ba -  for Sale in Lancelot/winter Park, Winter Park
New
$93,500
2 Beds
2 Baths
840 SqFt
Status Active
MLS # O5734361
Property Type Condominium
AS IS Beautiful and clean second floor unit. New paint and maintained professionally. Great for investment or primary living. Solid and continuous rental income.Close to major roadways. Top educational institutions within close proximity.Move in ready.

257 Lewfield Cir #257 Winter Park, FL 32792

$82,000 - 1Br/1Ba -  for Sale in Stratford A Winter Park Condo, Winter Park
New
$82,000
1 Bed
1 Bath
678 SqFt
Status Active
MLS # O5734111
Property Type Condominium
Don't miss this opportunity to be in Winter Park! Fabulously maintained and updated FIRST FLOOR one bedroom one bath condo centrally located to shopping, dining, major Central Florida thoroughfares, and close proximity to Full Sail, Rollins, and UCF!! This turn-key condo offers a shaded screened and covered back porch with POOL VIEW, new water heater, new paint throughout, new condo sized stainless steel fridge, and stackable washer and dryer set. This charming unit is well worth your visit!! **Please verify rental restrictions**

1024 Aragon Ave Winter Park, FL 32789

$375,000
3 Beds
3 Baths
1,750 SqFt
Status Active
MLS # O5731885
Property Type Townhouse
Don't miss this beautiful new three bedroom, three full bathroom townhouse nestled in the heart of Winter Park! Built in 2016, this home has all of the modern amenities you'd expect in a new townhome. With an open concept kitchen/living room combo, it's perfect for entertaining! You'll love the beautiful bright kitchen with fantastic quartzite countertops. The modern insulation and tankless hot water heater help keep your electric costs down. There's even a flex space you could use as a third bedroom, or as an office. Three full bathrooms make this home perfect for a growing family or an amazing investment property. Close to downtown Winter Park, Rollins College, Park Ave, Publix, The Porch, and all that Winter Park has to offer! Call today for an appointment!

637 N Park Ave #5 Winter Park, FL 32789

$3,390,000
3 Beds
5 Baths
4,237 SqFt
Status Active
MLS # O5734148
Property Type Townhouse
Under Construction - The luxurious Park Hill townhomes, a legacy residence, have set a new standard of excellence in Winter Park’s high end market and are in a class of their own. With only 5 units remaining, this is a rare opportunity to own the most well-appointed and exclusive townhomes ever constructed in Winter Park. Built and executed by the vision of Hill Gray Seven Development, Park Hill’s classically styled architecture sits atop what is likely the only remaining new construction along the prominent stretch of Park Avenue. Created to stand the test of time, the flawless construction includes the highest quality materials: tumbled handmade Old Carolina brick, 3 story block construction, soundproof hollow core floors, precast exterior trim, copper flashing, and a slate mansard roof. Interior features are lavish, with high ceilings on every floor, walls of windows, French doors, custom built-ins, intricate trim & crown molding, custom closets, and smart home technology throughout. Spanning 3 floors, there are 3 bedrooms plus bonus room, gourmet kitchen with Wolf Sub Z appliances, and great entertaining space inside and out. Other amenities are private elevator, outdoor summer kitchen, rooftop terrace, 2 car garage. Fee simple ownership, exterior maintenance handled by the association. Perfect location, easy to lock & leave...become part of Winter Park’s legacy of excellence.

3533 Seagrape Dr Winter Park, FL 32792

$175,000
3 Beds
1 Bath
1,462 SqFt
Status Active
MLS # O5734173
Property Type Single Family Residence
Solid mid century home in Winter Park! This home is ready for updating or can be lived in and be fixed up with some sweat equity! There is a huge family room and a Florida room plus a enclosed garage for additional storage. Outside there is a screened porch, two covered porches, a huge cement block workshop with electricity and two storage sheds. The plumbing, electric and water heater have been updated. Hurry this is a great price for the area!

Winter Park Homes For Sale, Condos For Sale & Orlando Real Estate

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