206 results in Winter Park for Single Family, Condos, Multi-Family, Land, Villa, Townhouse, Boat Dock, Coming Soon, Backup
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Winter Park, FL

$1,089,000

  • Address 1700 WINTER PARK ROAD
  • Acreage 0.2
  • Sqr Ft 2131
  • Baths 3
  • Bedrooms 3

Location! Location! Location! Don't miss out on this beautiful home in the heart of Winter Park! One block from Lake Virginia and just minutes from amazing shopping, dining, and the famous Park Ave! Z....

Winter Park, FL

$669,900

  • Address 3114 HEARTLEAF PL
  • Acreage 0.96
  • Sqr Ft 2702
  • Baths 3
  • Bedrooms 4

It is all about LOCATION, LOCATION, LOCATION!! This beautiful spacious Winter Park home, is located in the Lost Creek subdivision, a very private community with no rear neighbors because it backs up t....

Winter Park, FL

$574,900

  • Address 283 N RANGER BOULEVARD
  • Acreage 0.19
  • Sqr Ft 1542
  • Baths 2
  • Bedrooms 3

Stunning, newer renovated, contemporary Winter Park Pines pool home. Highly desirable neighborhood, with excellent Winter Park Schools. Steps from popular Cady Way walking/biking trail. Upgraded “co....

Winter Park, FL

$475,000

  • Address 1568 LITTLE WREN LANE
  • Acreage 0.06
  • Sqr Ft 1961
  • Baths 2
  • Bedrooms 3

Welcome to this Luxury townhome in the highly sought after HAWKS CREST Community in Winter Park! This is a contemporary property with modern interior finishes. Featuring an open concept plan, 3 bedr....

Winter Park, FL

$1,789,900

  • Address 280 E LAKE SUE AVENUE
  • Acreage 0.25
  • Sqr Ft 3422
  • Baths 4
  • Bedrooms 5

Pre-Construction. To be built. Customize-to-suite this gorgeous Bermudan-style landmark home in the heart of Olde Winter Park! Presented by by Parade of Homes Winner, Wooten Built, Inc. This elegant ....

Winter Park, FL

$899,000

  • Address 616 WORTHINGTON DRIVE
  • Acreage 0.22
  • Sqr Ft 1549
  • Baths 3
  • Bedrooms 4

Welcome home to this thoughtfully renovated house in a desirable Winter Park neighborhood. Built in 1958, the property has only had two owners and has been maintained and updated with care. A mid-cent....

Winter Park, FL

$1,699,000

  • Address 1209 SHARON PLACE
  • Acreage 0.38
  • Sqr Ft 2079
  • Baths 3
  • Bedrooms 4

Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in the land. Walking distance to t....

Winter Park, FL

$435,000

  • Address 1840 MEADOWGOLD LANE
  • Acreage 0.14
  • Sqr Ft 1708
  • Baths 2
  • Bedrooms 3

Rare opportunity to own this beautiful 3 bedroom 3 bath 1,708 sqft home in the highly desirable community of Autumn Glen. This community is in high demand for countless reasons, one of them being its ....

Winter Park, FL

$310,000

  • Address 595 OLOLU DRIVE
  • Acreage 0.13
  • Sqr Ft 729
  • Baths 1
  • Bedrooms 2

This updated mid-century charmer has lovely tropical curb appeal and sits just across the street from Lake Killarney! Step inside the front door to find an open layout with original hardwood floors th....

Winter Park, FL

$525,000

  • Address 2855 CADY WAY
  • Acreage 0.18
  • Sqr Ft 1736
  • Baths 2
  • Bedrooms 3

Here it is, the renovated beauty you’ve been waiting for! A 1963, Winter Park home that has been fully updated. PLUMBING, ELECTRIC, A/C NEW IN 2016. ROOF 2015. HOT WATER HEATER 2022! The large, open....

Winter Park, FL

$1,550,000

  • Address 1333 MAYFIELD AVENUE
  • Acreage 0.24
  • Sqr Ft 3129
  • Baths 3
  • Bedrooms 5

This classic, impeccable 5-bedroom home offers the perfect balance of size and functionality, with a fantastic outdoor space, a large saltwater pool with a sun shelf wrapped in Chicago brick, and a do....

Winter Park, FL

$1,995,000

  • Address 147 S INTERLACHEN AVENUE #101
  • Acreage 0.54
  • Sqr Ft 3317
  • Baths 4
  • Bedrooms 4

This is a rare opportunity to purchase a large ground floor unit in 147 Interlachen Place in the heart of downtown Winter Park. The 8-condo building surrounds an atrium open to the sky, so natural li....

Winter Park, FL

$99,000

  • Address 3071 GEORGE MASON AVENUE #D
  • Acreage 10.07
  • Sqr Ft 549
  • Baths 1
  • Bedrooms 1

DUE TO MULTIPLE OFFERS, NO SHOWINGS PAST MONDAY, JUNE 27TH. Rare gem in THE COLONIES. This One bedroom, one bathroom with balcony condo is located in Winter Park. Great for investors as may lease imme....

Winter Park, FL

$540,000

  • Address 2808 AMSDEN ROAD
  • Acreage 0.25
  • Sqr Ft 2020
  • Baths 3
  • Bedrooms 3

Enjoy all Winter Park has to offer! This Winter Park Estates home is ready for a new owner. This house was meticulously taken care of. Completed renovated inside and out! This home features new floori....

Winter Park, FL

$313,990

  • Address 1811 ASTER DRIVE
  • Acreage 0.22
  • Sqr Ft 1554
  • Baths 2
  • Bedrooms 3

Welcome home to this beautiful traditional style three bedroom, two bathroom home, located in the heart of Winter Park. Upon entering, you're greeted with the quaint kitchen and charming living area f....

Winter Park, FL

$2,100,000

  • Address 472 FLETCHER PLACE
  • Acreage 0.51
  • Sqr Ft 4286
  • Baths 4
  • Bedrooms 4

Winter Park custom home on a quiet street with lake access to Winter Park Chain of Lakes on Lake Osceola at end of street. This 4-bedroom 4.5 bath home is on over ½ acre. 3-way split plan with downst....

Winter Park, FL

$1,699,000

  • Address 1209 SHARON PLACE
  • Acreage 0.38
  • Sqr Ft N/A
  • Baths 0
  • Bedrooms 0

Excellent opportunity to build your dream home near The Vias in Winter Park. Oversized 108x152, 0.38 acre lot. Existing structure on the site has no value - value is in the land. Walking distance to t....

Winter Park, FL

$425,000

  • Address 3130 LOWNDES DRIVE
  • Acreage 0.18
  • Sqr Ft 1200
  • Baths 2
  • Bedrooms 3

This Winter Park one-story home offers a patio, quartz countertops, and a one-car garage.....

Winter Park, FL

$349,900

  • Address 2312 BONANZA AVENUE
  • Acreage 0.13
  • Sqr Ft 1756
  • Baths 2
  • Bedrooms 4

This Winter Park home offers 4 spacious bedrooms, 2 full bathrooms and all with no HOA. This home offers a split floor plan with an open concept design for the living room, kitchen and dining room. Th....

Winter Park, FL

$499,900

  • Address 1742 WILLA CIRCLE
  • Acreage 0.51
  • Sqr Ft 2313
  • Baths 2
  • Bedrooms 4

WELCOME HOME! You will fall in love with this lovely home on an oversized lot in a quiet, family-friendly Winter Park subdivision- Willa Grove. The versatile floor plan offers more than 2300 sq. ft a....

Winter Park, FL

$674,900

  • Address 743 LONDON ROAD
  • Acreage 0.21
  • Sqr Ft 2121
  • Baths 2
  • Bedrooms 4

Gorgeous, completely renovated 1-level home on a quiet street in Winter Park Pines with modern finishes. AC 2020, rew roof 2017, updated electric & plumbing. Sleek island kitchen with custom rift sawn....

Winter Park, FL

$335,000

  • Address 865 EASTBROOK BOULEVARD
  • Acreage 0.19
  • Sqr Ft 1415
  • Baths 2
  • Bedrooms 3

Lovely MOVE-IN READY 3 Bedroom 2 Bath home in Winter Park within the Orange County/Winter Park School District. Home is very clean, sanitized, and well maintained. NEW: ROOF 2021, PLUMBING 2021, A/C....

Winter Park, FL

$2,465,000

  • Address 1228 MAYFIELD AVENUE
  • Acreage 0.47
  • Sqr Ft 4013
  • Baths 3
  • Bedrooms 4

This spectacular home blends Santa Barbara Spanish Colonial architecture with stylish comfort and old Florida charm. Situated on an oversized 22,000-plus-square-foot lot on one of the most highly desi....

Winter Park, FL

$199,990

  • Address 2483 TAHOE CIRCLE
  • Acreage 0.05
  • Sqr Ft 1295
  • Baths 2
  • Bedrooms 2

The quiet and charming Cedarwood community offers great features and the ideal Winter Park location for accessibility to everything you could need. The 2 bedroom split floor plan has one bedroom at th....

All Listings in Winter Park
Stats for Winter Park

Average Price in Winter Park: $1,190,000
County Average: $730,000

163%

Average Taxes in Winter Park: $5,886
County Average: $4,891

120%

Average Price per/ft2 in Winter Park: $502
County Average: $318

158%

Average Walkscore in Winter Park: 43
County Average: 28

151%

Average Days on Website in Winter Park: 60
County Average: 44

136%
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