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- Subdivision Like Winter Park
Single Family
- Price: $8,799,000.00
- Price sqft: $1,805.29 / sqft
- Previous Price: $10,999,999
- Last Price Change: 03/19/25
- Days On Market: 126
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 4874
- 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: PV LUXURY GROUP PA
- DMCA Notice
CALLING HIGHEST AND BEST BY 4/30/2025!!
Introducing a Unique, Stunning Modern Home
A groundbreaking architectural masterpiece, this one of a kind residence is built with reinforced concrete, st
Single Family
- Price: $3,950,000.00
- Price sqft: $45.01 / sqft
- Days On Market: 12
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 87762
- Acreage: 0.89 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 1935
MLS#: O6291851
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: FANNIE HILLMAN & ASSOCIATES
- DMCA Notice
Nestled on a sprawling 0.89 acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamb
Condominium
- Price: $2,890,000.00
- Price sqft: $1,127.15 / sqft
- Days On Market: 187
- Bedrooms: 3
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 2564
- Acreage: 0.32 acres
- Pool: No
- Waterfront: No
- Year Built: 2008
MLS#: O6245393
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Landmark Winter Park Condo
- Building: Landmark Winter Park Condo
- Provided by: KELLER WILLIAMS WINTER PARK
- DMCA Notice
Introducing the coveted corner penthouse unit in one of winter park's luxury condo building. The landmark building is an award winning luxury condo building located in downtown winter park. An extensi
Single Family
- Price: $2,395,000.00
- Price sqft: $460.93 / sqft
- Days On Market: 48
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 5196
- Acreage: 0.27 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6278049
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COMPASS FLORIDA LLC
- DMCA Notice
Discover an extraordinary blend of modern elegance and thoughtful craftsmanship in this brand new architectural gem by DaVinci Development. This stunning five bedroom, six and a half bathroom home spa
Single Family
- Price: $2,290,000.00
- Price sqft: $673.73 / sqft
- Previous Price: $2,374,000
- Last Price Change: 03/30/25
- Days On Market: 165
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3399
- Acreage: 0.24 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2022
MLS#: O6250342
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
This exquisite, custom designed residence blends impeccable architectural details with unparalleled craftsmanship, in the highly sought Winter Park Village. With Pella windows and natural stone accent
Single Family
- Price: $1,650,000.00
- Price sqft: $435.47 / sqft
- Days On Market: 4
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3789
- Acreage: 0.17 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6294433
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Village
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: CORCORAN PREMIER REALTY
- DMCA Notice
This brand new custom home is nestled in an up and coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to crea
Condominium
- Price: $1,650,000.00
- Price sqft: $519.85 / sqft
- Previous Price: $1,695,000
- Last Price Change: 03/22/25
- Days On Market: 144
- Bedrooms: 3
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 3174
- Acreage: 0.46 acres
- Pool: No
- Waterfront: No
- Year Built: 2009
MLS#: O6256094
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Residential Condom
- Building: Winter Park Residential Condominium 95413489
- Elementary School: Audubon Park K8
- Middle School: Audubon Park K 8
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
One or more photo(s) has been virtually staged. This one of a kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 squ
Single Family
- Price: $1,295,000.00
- Price sqft: $479.63 / sqft
- Previous Price: $1,395,000
- Last Price Change: 03/30/25
- Days On Market: 82
- Bedrooms: 5
- Baths: 4
- Bldg sqft: 2700
- Acreage: 0.15 acres
- Pool: No
- Waterfront: No
- Year Built: 2018
MLS#: O6270087
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park
- Elementary School: Brookshire Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COLDWELL BANKER RESIDENTIAL RE
- DMCA Notice
From the boutique address at 433 Carolina Ave, take a stroll down to historic Hannibal Square or to the New England gourmet corridor. On Saturday's mornings, have your breakfast at the Winter Park far
Single Family
- Price: $1,195,000.00
- Price sqft: $334.92 / sqft
- Days On Market: 46
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3568
- Acreage: 0.23 acres
- Pool: No
- Waterfront: No
- Year Built: 1967
MLS#: O6279805
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park Heights
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Step into this stunning one story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offering four bedrooms and three baths, this thoughtfully designed residence seamlessl
Single Family
- Price: $975,000.00
- Price sqft: $134.72 / sqft
- Days On Market: 40
- Bedrooms: 3
- Baths: 1
- Garage / Parking Spaces: 1
- Bldg sqft: 7237
- Acreage: 0.17 acres
- Pool: No
- Waterfront: No
- Year Built: 1925
MLS#: O6282808
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Winter Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: KELLER WILLIAMS WINTER PARK
- DMCA Notice
Beautiful Winter Park historic home that's been totally gutted and renovated. Comes complete with new doors, windows, AC, roof, water heater and gas furnace. Impeccable landscaping as well as larger

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