Searching on:
- City = Winter Park
- Listing Status = Active
Single Family
- Price: $8,950,000.00
- Price sqft: $669.06 / sqft
- Days On Market: 165
- Bedrooms: 7
- Baths: 11
- Garage / Parking Spaces: 4
- Bldg sqft: 13377
- Acreage: 1.63 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 2009
MLS#: O6350054
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsongpreserve Point
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Description
- In the exclusive community of Windsong on Lake Berry, this magnificent 1.6 acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped
Single Family
- Price: $8,500,000.00
- Price sqft: $928.05 / sqft
- Days On Market: 296
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 9159
- Acreage: 1.94 acres
- Pool: Yes
- Community Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Front
- Year Built: 2013
MLS#: O6312768
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Windsong Preserve Point 4376
- Elementary School: Brookshire Elem
- Middle School: Glenridge
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2 acre lakefront estate, is absolutely gorgeous and is available for the first time! Cus
Multi-Family
- Price: $7,150,000.00
- Days On Market: 30
- Garage / Parking Spaces: 8
- Acreage: 0.27 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6383456
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Provided by: REAL BROKER, LLC
-
- DMCA Notice
Description
- This exclusive trifecta investment opportunity combines luxury real estate, dual lane income potential, and powerful tax advantagesall in one of the fastest growing markets in the country. Investors c
Single Family
- Price: $6,950,000.00
- Price sqft: $799.03 / sqft
- Days On Market: 39
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 4
- Bldg sqft: 8698
- Acreage: 0.30 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6380444
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Elementary School: Lakemont Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: ONE LUXURY INTERNATIONAL LLC
-
- DMCA Notice
Description
- Under Construction. Opportunities like this rarely present themself, just a eight minute walk from the iconic shops, restaurants, and cafs of Park Avenue, 40 Palmer represents a rare convergence of ar
Single Family
- Price: $6,900,000.00
- Price sqft: $875.41 / sqft
- Days On Market: 17
- Bedrooms: 6
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 7882
- Acreage: 0.57 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Freshwater
- Year Built: 1991
MLS#: O6387200
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: J Kronenberger Sub
- Elementary School: Lakemont Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- Rarely does a property of this caliber grace the Winter Park market. Nestled along the coveted Venetian Canal with 95 feet of pristine waterfrontage, this magnificent masonry estate is the pinnacle of
Single Family
- Price: $6,895,000.00
- Price sqft: $861.66 / sqft
- Previous Price: $7,200,000
- Last Price Change: 01/07/26
- Days On Market: 149
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 8002
- Acreage: 0.48 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6349188
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Osceola Place
- Elementary School: Lakemont Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: FANNIE HILLMAN & ASSOCIATES
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- DMCA Notice
Description
- Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenues renowned shops, fine dining, and the iconic Winter Park 9 hole golf course,
Single Family
- Price: $6,600,000.00
- Price sqft: $1,261.71 / sqft
- Previous Price: $8,500,000
- Last Price Change: 09/08/25
- Days On Market: 479
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 5231
- Acreage: 0.36 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6260493
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park
- Provided by: COMPASS FLORIDA LLC
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- DMCA Notice
Description
- Calling highest and best by 09/26/2025!! Seller financing available with very attractive terms introducing a unique, stunning modern home a groundbreaking architectural masterpiece, this one of
Single Family
- Price: $6,450,000.00
- Price sqft: $793.94 / sqft
- Days On Market: 35
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 8124
- Acreage: 0.45 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2001
MLS#: O6381761
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Cloister Grove Sub
- Elementary School: Lakemont Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
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- DMCA Notice
Description
- Along one of the cobblestone brick streets in the prestigious Vias of Winter Park, this completely renovated residence pairs timeless European influence with clean architectural lines and bespoke fini
Single Family
- Price: $5,495,000.00
- Price sqft: $599.50 / sqft
- Previous Price: $5,950,000
- Last Price Change: 09/08/25
- Days On Market: 270
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 5
- Bldg sqft: 9166
- Acreage: 0.69 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal Front,Lake Privileges
- Year Built: 2008
MLS#: O6319674
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores
- Elementary School: Dommerich Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: FORTUNE INTERNATIONAL REALTY
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- DMCA Notice
Description
- Exquisite Waterfront Estate in the Heart of Winter Park Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Parks most prestigious neighb
Single Family
- Price: $4,995,000.00
- Price sqft: $765.64 / sqft
- Previous Price: $5,250,000
- Last Price Change: 03/12/26
- Days On Market: 64
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 6524
- Acreage: 0.34 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6373743
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Virginia Heights Rep
- Elementary School: Audubon Park K
- Middle School: Audubon Park K
- High School: Winter Park
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
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- DMCA Notice
Description
- Now offered with a significant price improvement, this award winning custom residence presents a rare opportunity in Winter Parks sought after Virginia Heights neighborhood, prized for its proximity t
