Searching on:
- Subdivision Like Maitland Shores
- Listing Status = Active
- 1
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: 269
- 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
- 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: $3,599,000.00
- Price sqft: $794.66 / sqft
- Days On Market: 66
- Bedrooms: 4
- Baths: 4
- Garage / Parking Spaces: 2
- Bldg sqft: 4529
- Acreage: 0.30 acres
- Pool: Yes
- Spa/HotTub: Yes
- Waterfront: No
- Year Built: 2001
MLS#: O6372165
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- Elementary School: Dommerich Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- Timeless Elegance Meets Modern Luxury in Winter Park's Most Coveted Location Discover an extraordinary residence where exceptional craftsmanship and sophisticated design converge at 948 Poinciana Lan
Single Family
- Price: $2,450,000.00
- Price sqft: $387.84 / sqft
- Days On Market: 13
- Bedrooms: 4
- Baths: 5
- Garage / Parking Spaces: 2
- Bldg sqft: 6317
- Acreage: 0.27 acres
- Pool: No
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Freshwater,Lake Privileges
- Year Built: 2008
MLS#: O6388219
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores First Add
- Elementary School: Dommerich Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: PALM PROPERTIES OF CF, INC.
-
- DMCA Notice
Description
- A rare Winter Park Canal, Chain of Lakes, water view custom home where art, architecture, and waterfront living converge. Step into your future with this extraordinary custom built residence, inspire
Single Family
- Price: $2,295,000.00
- Price sqft: $428.73 / sqft
- Previous Price: $2,345,000
- Last Price Change: 02/14/26
- Days On Market: 135
- 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
- High School: Winter Park
- Provided by: CORCORAN PREMIER REALTY
-
- DMCA Notice
Description
- Welcome to 2299 Via Tuscany, a remarkable 4 bedroom, 3.5 bathroom residence in the prestigious Winter Park Vias. This 3,986 square foot home, set on a .40 acre private lot, offers a blend of luxury an
Single Family
- Price: $1,699,000.00
- Price sqft: $414.80 / sqft
- Previous Price: $1,749,000
- Last Price Change: 03/18/26
- Days On Market: 20
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 4096
- Acreage: 0.37 acres
- Pool: No
- Spa/HotTub: Yes
- Waterfront: Yes
- Wateraccess: Yes
- Waterfront Type: Canal - Freshwater,Canal Front
- Year Built: 1959
MLS#: O6386288
- County: ORANGE
- City: WINTER PARK
- Zipcode: 32789
- Subdivision: Maitland Shores
- Elementary School: Dommerich Elem
- Middle School: Maitland
- High School: Winter Park
- 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 squa
Single Family
- Price: $1,329,950.00
- Price sqft: $281.00 / sqft
- Previous Price: $1,359,950
- Last Price Change: 02/12/26
- Days On Market: 302
- 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
- High School: Winter Park
- 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: $1,225,000.00
- Price sqft: $394.40 / sqft
- Previous Price: $1,339,000
- Last Price Change: 03/07/26
- Days On Market: 70
- Bedrooms: 4
- Baths: 3
- Garage / Parking Spaces: 2
- Bldg sqft: 3106
- Acreage: 0.27 acres
- Pool: No
- Waterfront: No
- Year Built: 1979
MLS#: O6371328
- County: ORANGE
- City: MAITLAND
- Zipcode: 32751
- Subdivision: Maitland Shores
- Elementary School: Dommerich Elem
- Middle School: Maitland
- High School: Winter Park
- Provided by: KELLY PRICE & COMPANY LLC
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- DMCA Notice
Description
- Welcome to 67 Cypress Lane, a stunning single owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This archit
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