Searching on:
- School = Maitland Middle
Single Family
- Price: $10,950,000.00
- Price sqft: $1,289.90 / sqft
- Previous Price: $11,950,000
- Last Price Change: 10/31/25
- Days On Market: 190
- Bedrooms: 5
- Baths: 8
- Garage / Parking Spaces: 2
- Bldg sqft: 8489
- Acreage: 1.86 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 1991
MLS#: O6304588
- County: ORANGE
- City: MAITLAND
- Zipcode: 32751
- Subdivision: Adams Grove
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
- DMCA Notice
Description
- Behind private gates along the shores of Lake Maitland, this elegant Mizner style Mediterranean estate offers an extraordinary opportunity to own a timeless lakefront masterpiece on the Winter Park Ch
Single Family
- Price: $7,200,000.00
- Price sqft: $899.78 / sqft
- Days On Market: 28
- 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 Middle
- High School: Winter Park High
- 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: $5,900,000.00
- Price sqft: $873.04 / sqft
- Previous Price: $6,500,000
- Last Price Change: 11/03/25
- Days On Market: 111
- Bedrooms: 6
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 6758
- Acreage: 1.07 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1924
MLS#: O6331715
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Dyer Susan Resub
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: FANNIE HILLMAN & ASSOCIATES
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- DMCA Notice
Description
- Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1 acre lot. Exuding timeless
Single Family
- Price: $5,895,000.00
- Price sqft: $579.36 / sqft
- Previous Price: $6,200,000
- Last Price Change: 10/05/25
- Days On Market: 264
- Bedrooms: 5
- Baths: 9
- Garage / Parking Spaces: 4
- Bldg sqft: 10175
- Acreage: 0.70 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 1996
MLS#: O6285791
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: J Kronenberger Sub
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: THE AGENCY ORLANDO
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- DMCA Notice
Description
- Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .71 acre corner lot in one of Winter Park's most sought after locations. This 7,916 SF property includes a main residence of ov
Single Family
- Price: $5,495,000.00
- Price sqft: $599.50 / sqft
- Previous Price: $5,950,000
- Last Price Change: 11/13/25
- Days On Market: 149
- 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 Middle
- High School: Winter Park High
- 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: $5,300,000.00
- Price sqft: $897.39 / sqft
- Days On Market: 34
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 3
- Bldg sqft: 5906
- Acreage: 0.34 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6353083
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Camwood Sub
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: FANNIE HILLMAN & ASSOCIATES
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- DMCA Notice
Description
- An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophisticationall just steps from Winter Parks iconic Park Avenue.
Land
- Price: $4,999,000.00
- Days On Market: 110
- Acreage: 0.48 acres
- Pool: No
- Waterfront: No
- Year Built: Not Available
MLS#: O6331207
- 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: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- JUST LISTED RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK OFFERED AT $4,999,000!!! Zoned R 3, this multi family, prime piece of land is ready for development. Luxury townhomes or condos, nothi
Single Family
- Price: $4,950,000.00
- Price sqft: $661.50 / sqft
- Previous Price: $5,200,000
- Last Price Change: 07/24/25
- Days On Market: 272
- Bedrooms: 5
- Baths: 7
- Garage / Parking Spaces: 3
- Bldg sqft: 7483
- Acreage: 0.36 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2024
MLS#: O6282425
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Comstock Park
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: PREMIER SOTHEBY'S INTL. REALTY
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- DMCA Notice
Description
- New Hamptons style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exception
Single Family
- Price: $4,750,000.00
- Price sqft: $1,082.99 / sqft
- Days On Market: 144
- Bedrooms: 4
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 4386
- Acreage: 0.21 acres
- Pool: Yes
- Waterfront: No
- Year Built: 2025
MLS#: O6321143
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Cloister Grove Sub
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- In the heart of Winter Parks coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean minimalist residence that blends architectural refinement w/ organic warmth. Designed and de
Single Family
- Price: $4,750,000.00
- Price sqft: $802.64 / sqft
- Days On Market: 73
- Bedrooms: 5
- Baths: 6
- Garage / Parking Spaces: 2
- Bldg sqft: 5918
- Acreage: 0.34 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2026
MLS#: O6337290
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Park Grove
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: COMPASS FLORIDA LLC
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- DMCA Notice
Description
- Under Construction. Just steps from the boutiques and fine dining of Park Avenue, this brand new bespoke estate by acclaimed builder Vimaro Homes delivers a rare combination of architectural sophistic
