Searching on:
- Subdivision Like Maitland Shores
- 1
Single Family
- Price: $5,495,000.00
- Price sqft: $599.50 / sqft
- Previous Price: $5,950,000
- Last Price Change: 11/23/25
- Days On Market: 160
- 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
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: $2,499,000.00
- Price sqft: $407.07 / sqft
- Previous Price: $2,599,000
- Last Price Change: 11/22/25
- Days On Market: 377
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 6139
- Acreage: 0.27 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Freshwater
- Year Built: 2008
MLS#: O6258445
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- 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
- "The richness of an artist is the fusion of influences that have shaped his life and work", ~ Fernando Botero. WELCOME HOME to 2550 Venetian Way, located in the historic and renowned city of Winter Pa
Single Family
- Price: $2,345,000.00
- Price sqft: $438.07 / sqft
- Days On Market: 26
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 5353
- Acreage: 0.40 acres
- Pool: Yes
- Waterfront: No
- Year Built: 1953
MLS#: O6355858
- 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: CORCORAN PREMIER REALTY
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- DMCA Notice
Description
- Stunning 4 bedroom, renovated pool home with new Architectural shingle roof (2023) on a generous .40 acre lot in the highly coveted Winter Park Vias with bright open living areas, high ceilings, hardw
Single Family
- Price: $1,836,000.00
- Price sqft: $448.24 / sqft
- Days On Market: 40
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 4096
- Acreage: 0.37 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Freshwater
- Year Built: 1959
MLS#: O6354284
- 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: PLAID PROPERTIES, LLC
-
- DMCA Notice
Description
- Canal Front Oasis on the Winter Park Chain of Lakes! Welcome to 1016 Howell Branch Road, where every day feels like a getaway. This beautifully reimagined 4 bedroom, 3 bath residence offers 3,142 squ
Single Family
- Price: $1,434,950.00
- Price sqft: $303.18 / sqft
- Previous Price: $1,474,950
- Last Price Change: 11/25/25
- Days On Market: 192
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4733
- Acreage: 0.21 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2008
MLS#: TB8388549
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: THE SHOP REAL ESTATE CO.
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- DMCA Notice
Description
- Back on market at no fault of the seller! Brand new Roof and HVAC systems 2025. Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and
Single Family
- Price: $975,000.00
- Price sqft: $516.69 / sqft
- Previous Price: $999,000
- Last Price Change: 11/01/25
- Days On Market: 204
- Bedrooms: 3
- Baths: 2
- Garage / Parking Spaces: 2
- Bldg sqft: 1887
- Acreage: 0.19 acres
- Pool: No
- Waterfront: No
- Year Built: 1953
MLS#: O6307671
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- Elementary School: Dommerich Elem
- Middle School: Maitland Middle
- High School: Winter Park High
- Provided by: VECTOR PROPERTY GROUP
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- DMCA Notice
Description
- ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL A 2023 Masterpiece Awaits! S
Rental
- Price: $8,990.00
- Price sqft: $1.48 / sqft
- Previous Price: $9,995
- Last Price Change: 10/04/25
- Days On Market: 141
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 3
- Bldg sqft: 6065
- Acreage: 0.63 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Lake Privileges
- Year Built: 1979
MLS#: O6324414
- 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: PALMANO GROUP RE BROKERAGE LLC
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- DMCA Notice
Description
- Only available for a 4 to 6 month lease. This RARE LAKEFRONT retreat is located on a quiet, tree lined street in the highly sought after Vias of Winter Park. Custom built and elevated on a prime lot w
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