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- School = Maitland Middle
Single Family
- Price: $10,950,000.00
- Price sqft: $1,289.90 / sqft
- Previous Price: $11,950,000
- Last Price Change: 11/22/25
- Days On Market: 203
- 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
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: $5,900,000.00
- Price sqft: $873.04 / sqft
- Previous Price: $6,500,000
- Last Price Change: 11/03/25
- Days On Market: 125
- 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
- DMCA Notice
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: 278
- 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
- DMCA Notice
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: 12/01/25
- Days On Market: 163
- 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
- DMCA Notice
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: 48
- 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
- DMCA Notice
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: 124
- 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
- DMCA Notice
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: 286
- 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
- DMCA Notice
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: $802.64 / sqft
- Days On Market: 87
- 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
- DMCA Notice
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
Single Family
- Price: $4,750,000.00
- Price sqft: $1,082.99 / sqft
- Days On Market: 158
- 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
- DMCA Notice
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: $4,545,000.00
- Price sqft: $830.44 / sqft
- Previous Price: $4,595,000
- Last Price Change: 10/24/25
- Days On Market: 105
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 5473
- Acreage: 0.32 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2021
MLS#: O6330736
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Valencia Terrace
- Elementary School: Lakemont Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: THE REAL ESTATE COLLECTION LLC
- DMCA Notice
Conveniently situated near the Winter Park Country Club, this contemporary masterpiece, built by premier builder Z Properties, offers the ideal mix of style, comfort, and modern living. Completed in 2
Listing Data ©2025 Greater Fort Lauderdale REALTORS®
Listings provided courtesy of The Hernando County Association of Realtors MLS.
Listing Data ©2025 REALTOR® Association of Citrus County
Listing Data ©2025 Royal Palm Coast Realtor® Association
The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.Display of MLS data is usually deemed reliable but is NOT guaranteed accurate.
Datafeed Last updated on December 4, 2025 @ 12:00 am
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