Winter Park Homes for Sale

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Single Family

550 COUNTRY CLUB DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,800Sqft
**2020 Parade of Homes WINNER for BEST Overall in the Pricing Category, BEST Overall Layout and BEST Craftsmanship!** This luxurious, custom-built, 5 bedroom, 4.5 bath LAKEFRONT pool home, with additional office space, was recently completed by Lazarus Development Group, and is located in beautiful Lake Killarney Shores in Winter Park.
$1,875,000

Single Family

2433 VIA TUSCANY, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
3Parking(s)
25Picture(s)
3,730Sqft
*Check out the 2 Virtual Tours and ask for a Floorplan!* Welcome to a fabulous pool home, in the Winter Park Via’s neighborhood, with all the desirable amenities including a 3-car garage, large brick circular driveway, main suite downstairs, functional floorplan, and a covered back patio for entertaining.
$1,275,000

Single Family

1760 VIA VENETIA, WINTER PARK, Florida 32789

4Bedroom(s)
6Bathroom(s)
3Parking(s)
10Picture(s)
6,242Sqft
Meticulously constructed 4 bedroom, 5.5 bath pool home in The Vias. Encompassing over 6,200 square feet of beautiful interior space, this home sits on an oversized .42 acre lot on a quiet street just steps away from Lake Maitland.
$2,385,000

Single Family

1560 CARDINAL COURT, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,581Sqft
This exquisite, 5-bedroom, 4.2-bath new Mediterranean-style home is just a short stroll from Park Avenue's shops and restaurants in Winter Park's exclusive Park Grove neighborhood. No details have been spared in this Gallimore-built masterpiece, with12-ft. ceilings, crown molding and custom accents throughout.
$1,924,900

Lots And Land

570 SEMINOLE DRIVE, WINTER PARK, Florida 32789

10Picture(s)
2.25Acre
WALK TO FAMED PARK AVENUE FROM THIS EPIC WINTER PARK ESTATE LOT!! This 2.25 acre lake front crown jewel is a once-in-a-lifetime offering of one of Old Winter Park’s most sought after waterfront lots.
$6,500,000

Rental

200 SANDLEWOOD TRAIL, WINTER PARK, Florida 32789

2Bedroom(s)
3Bathroom(s)
20Picture(s)
1,133Sqft
Lovely, light and airy home with new appliances, fresh paint through out and new laminate flooring upstairs. The kitchen shines with new appliances and eat-in space, large window that floods the room with natural light. The spacious living and dining features a corner fireplace - tile flooring and over-sized sliders that open to back patio and greens space...pool is short walk across the yard.
$1,450

Single Family

249 W LYMAN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
5Picture(s)
988Sqft
Heart of Winter Park! 2 Lots! Build on 14,867 sq ft of land (.34 acres, 2 lots) - - One Block to toney Park Avenue - - with upscale restaurants and shopping! Two single-family adjacent lots in this parcel. A small home, 2/1, built in 1970, remains today. Has newer A/C and new roof 2019, freshly painted.
$785,000

Single Family

30 E STOVIN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,950Sqft
Absolutely stunning, single-story home on the corner of Park Avenue! Walking distance to the Winter Park Golf Course and all of Park Avenue's shops and restaurants. Completely updated, this show-stopping home features 3 bedrooms, 2 full baths, open living, and a gorgeous chef's kitchen.
$1,250,000

Single Family

1324 INDIANA AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
21Picture(s)
1,692Sqft
Absolutely gorgeous renovation of this 1930’s Winter Park bungalow. The home has been impeccably restored to save the historic architectural details and adding the modern amenities such as a beautiful gourmet kitchen, complete with custom cabinetry, stainless steel appliances and hard surface counter tops.
$525,000

Condominium

315 E NEW ENGLAND AVENUE E, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,806Sqft
STUNNING WINTER PARK three bedroom condo oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly across from the chic Alfond Inn.
$1,650,000

Single Family

1730 GREENWICH AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
4,611Sqft
Located in the heart of Winter Park, this virtually new Modern Florida Coastal custom pool home was built by David Cahill (2015) who’s attention to detail is widely respected. It is well appointed and showcases over 4,600 SQFT of open living space. There are 4 bedrooms, 4 ½ bathrooms, an office/den, media room and a bonus room.
$1,697,000

Single Family

1351 ONECO AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
1Parking(s)
23Picture(s)
2,474Sqft
Welcome to this move-in ready home with a perfect floor plan on one of the best streets in Winter Park! Every room in this updated home is exactly where they should be for the ideal flow and functionality. The kitchen leads to the large dining room, with a bedroom off to the side that would make a perfect guest room.
$619,000

Commercial

2443-2445 LEE ROAD, WINTER PARK, Florida 32789

10Picture(s)
2,636Sqft
2,500 +/- SF Free-standing office/residential for sale, currently sub-divided into two (2) - 1,250 +/- SF separate suites. Suite 2443 is leased on a Month to Month basis. Suite 2445 is currently vacant. Great owner/user opportunity with signage and 37,000 vehicles per day on Lee Road and 170,000 vehicles AADT on Interstate 4. It offers 11 Parking spaces.
$549,900

Rental

1020 MINNESOTA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
1Parking(s)
25Picture(s)
2,000Sqft
Beautiful Mediterranean-Themed condominium conveniently located in the heart of Winter Park. Minutes from downtown Orlando, Rollins College, Park Ave, Winter Park Village and easy access to I-4. Unit is a 3-story design with bonus room with full bath, wet bar, 1 large terrace w/awning, plus a small terrace. Master Bedroom with Juliet balcony.
$2,800

Condominium

1140 WASHINGTON AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,069Sqft
Fabulous opportunity in the very desirable Winter Park! Location can't be beat! This unique condo with over 2000 SF living space is nestled on a tree and brick-lined street, features a 3 bedroom 2.5 bath townhome with open kitchen/family room concept with wood burning fireplace and beautiful natural light from ceiling to floor windows.
$354,000

Single Family

235 GENIUS DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
4Parking(s)
10Picture(s)
9,425Sqft
Stunning Mediterranean estate on the Winter Park chain of lakes. Nearly 10,000 square feet of exquisite living space provides a comfortable scale in every room; space for every member of the family. Fine craftsmanship and attention to detail are evident throughout.
$5,950,000

Single Family

1128 PRESERVE POINT DRIVE, WINTER PARK, Florida 32789

5Bedroom(s)
5Bathroom(s)
3Parking(s)
10Picture(s)
6,179Sqft
Welcome to this gorgeous, one-of-a-kind, contemporary-style home with over 150’ on the shores of Lake Berry. Custom built and architecturally stunning, this 5 bedroom, 4.5 bath home is pure perfection inside and out.
$4,199,000

Rental

1885 JEWELL AVENUE, WINTER PARK, Florida 32789

1Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
773Sqft
Alexan Winter Park is an apartment community designed with you in mind, putting extra care into every detail. THIS 1 BEDROOM 1 BATHROOM UNIT IS ONE OF MANY FLOOR PLANS CURRENTLY AVAILABLE. Details that make your living space an extension of you, with open floor plans and extra touches like keyless entry and USB outlets.
$1,588

Rental

1874 HARMON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,064Sqft
Alexan Winter Park is an apartment community designed with you in mind, putting extra care into every detail. THIS 2 BEDROOM 2 BATHROOM UNIT IS ONE OF MANY FLOOR PLANS CURRENTLY AVAILABLE. Details that make your living space an extension of you, with open floor plans and extra touches like keyless entry and USB outlets.
$1,815

Townhouse

345 W WELBOURNE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
23Picture(s)
2,734Sqft
Opportunity at The Douglas Grand! Enjoy a carefree, urban lifestyle in beautiful downtown Winter Park - just one block from chic Park Avenue with its lovely boutique shoppes, bistros, sidewalk cafes and restaurants - and of course the beauty of Central Park - and old-fashioned holiday parades. A wonderful, carefree lifestyle awaits you - and there is so much to do...
$799,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

1Bedroom(s)
1Bathroom(s)
1Parking(s)
25Picture(s)
1,090Sqft
MILLION DOLLAR VIEW of Lake Osceola! This one bedroom unit boasts almost 1100 SF and has been tastefully renovated. Floor to ceiling sliding glass doors give you an unobstructed view of the lake. Newer windows illuminate natural light to an open floor plan. Kitchen and bath have been updated. Crown molding. Wonderful storage. Laundry inside the unit PLUS 1 car covered parking space in garage.
$359,000

Single Family

1017 VIA TUSCANY OAKS WAY, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
4,230Sqft
Gorgeous Transitional Rex Tibbs, Winter Park Custom Home in the heart of the vias with deeded Lake Maitland access!! 5 Bedroom / 5.5 Bath home has master retreat and dedicated office and/or nursery/bedroom on ground floor and huge entertaining bonus. Located on highly desirable Via Tuscany in quiet, cul-de-sac , oversized lot with a 3 car garage.
$1,315,000

Condominium

662 OSCEOLA AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,290Sqft
Lock and leave lifestyle! This beautiful, light and bright, 2,290 sf condo features an amazing open floor plan, a wonderful open kitchen with granite counters and stainless steel appliances, and a spacious primary bedroom with a huge walk-in closet.
$1,099,000

Condominium

228 SCOTTSDALE SQUARE, WINTER PARK, Florida 32792

3Bedroom(s)
2Bathroom(s)
10Picture(s)
1,250Sqft
Completely renovated 3 Bedroom Loft Style condo for sale, new flooring, painting, main door, lights and fixtures, located on 436/Semoran Blvd only 10 min to Orlando Downtown. Tenant occupied unit offers Perfect opportunity for your Investment cash flow. Call for showing.
$140,000
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