1860 Summerland Avenue, Winter Park, FL 32789
Pending $5,675,000
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Under contract-accepting backup offers. Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.
Ceiling Fans(s)
Dry Bar
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Solid Surface Counters
Split Bedroom
Walk-In Closet(s)
Taxes: $12.00
Tax Year: 2025
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Rain Gutters
Bar Fridge
Built-In Oven
Microwave
Range Hood
Refrigerator
Tankless Water Heater
Wine Refrigerator
Pool
Water
Lake Front
Lake Privileges
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Junior High: Maitland Middle
High School: Winter Park High
MLS Area: 32789 - Winter Park
Price per Square Feet: $1,130.03
Water: Public
Lot Desc.: City Limits, In County, Irregular Lot, Paved
Construction: Stucco, Frame
Date Listed: 2025-11-06 21:59:01
Pool: Yes
Pool Type: In Ground, Salt Water
Parking: Driveway, Garage Door Opener, Garage Faces Side, Guest, Oversized, Parking Pad
Garage Spaces: 4
Flooring: Carpet, Ceramic Tile, Hardwood, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Listing Courtesy Of: Compass Florida Llc
jsloan2000@earthlink.net
Under contract-accepting backup offers. Tucked away on a quiet and beautiful Lake Maitland lot in the highly desirable Green Oaks neighborhood, this stunning French Provincial residence offers magnificent water views from nearly every room. With one of the most private entrances and lots in all of Winter Park, this timeless home blends European charm with modern comfort. The light-filled, open floor plan features a downstairs primary suite and a gorgeous family room with gas fireplace, opening to the pool and lake. The gourmet kitchen, also facing the backyard, is the heart of the home. Featuring granite countertops, light cabinetry and gas cooktop. The open layout includes the eat-in breakfast area and family room. Multiple French doors to the pool and lakefront for everyday indoor-outdoor living and enjoy breathtaking views that make every moment feel like a getaway. Upstairs, two generously sized bedrooms-each with en-suite baths are joined by a cozy conversation area with lake views, a large bonus room and a private office/study that could easily be an additional bedroom. A connecting guesthouse offers a true retreat with two bedrooms, a full bath, living area and kitchen, perfect for hosting friends or family. Sparkling pool, lush landscaping, and private dock on Lake Maitland, enjoy awe-inspiring sunrise views over the Isle of Sicily. Craftsmanship is showcased throughout, from the millwork to the 4-car garage, with extensive updates: roof (2021), multiple A/C systems with UV lights (2020–2025), new flooring throughout downstairs and all bedrooms (2020), updated upstairs windows (2020), rebuilt balcony with Trex decking, new pool equipment (2020) and pool converted to salt (filter 2024), Generac whole-house generator, Trex deck and dock with new cables and 7,500-lb lift (2022), new primary, upstairs guest suites and powder baths (2025), marble porcelain fireplace surround, remote shades in the primary suite, and new lighting fixtures throughout. Surrounded by manicured grounds and minutes from downtown Winter Park, Park Avenue shopping and restaurants, Enzian Theater, library, bike paths, and top-rated schools, (Dommerich, Maitland Middle and Winter Park High School). Just around the corner from Park Maitland and near Lake Highland and Trinity Preparatory Schools. This lakeside masterpiece offers unmatched privacy, luxury, and timeless sophistication-a truly exceptional home. Ski, wakeboard, pontoon or cruise around Dog Island and Isle of Sicily on the chain of lakes. Enjoy the magic of the holiday season- festive boat parade and holiday light displays. 121 ft of lakefront on the Winter Park Chain of Lakes.
Property Details
Price: $5,675,000
Sq Ft: 5,022
($1,130 per sqft)
Bedrooms: 5
Bathrooms: 4
Partial Baths: 2
City: Winter Park
County: Orange
Type: Single Family Reside
Development: Green Oaks Rep
Acres: 0.69
Virtual Tour/Floorplan: View
Year Built: 1992
Listing Number: O6358159
Status Code: Pending
Taxes: $12.00
Tax Year: 2025
Garage:
4
Interior Features:
Ceiling Fans(s)
Dry Bar
Eat-in Kitchen
High Ceilings
Kitchen/Family Room Combo
Primary Bedroom Main Floor
Solid Surface Counters
Split Bedroom
Walk-In Closet(s)
Financial Information:
Taxes: $12.00
Tax Year: 2025
Exterior Features:
French Doors
Lighting
Outdoor Grill
Outdoor Kitchen
Outdoor Shower
Rain Gutters
Equipment:
Bar Fridge
Built-In Oven
Microwave
Range Hood
Refrigerator
Tankless Water Heater
Wine Refrigerator
View:
Pool
Water
Waterfront Description:
Lake Front
Lake Privileges
School Information:
Elementary School: Dommerich Elem
Middle School: Maitland Middle
Junior High: Maitland Middle
High School: Winter Park High
Additional Information:
MLS Area: 32789 - Winter Park
Price per Square Feet: $1,130.03
Water: Public
Lot Desc.: City Limits, In County, Irregular Lot, Paved
Construction: Stucco, Frame
Date Listed: 2025-11-06 21:59:01
Pool: Yes
Pool Type: In Ground, Salt Water
Parking: Driveway, Garage Door Opener, Garage Faces Side, Guest, Oversized, Parking Pad
Garage Spaces: 4
Flooring: Carpet, Ceramic Tile, Hardwood, Wood
Roof: Shingle
Heating: Central
Cooling: Central Air
Sewer: Public Sewer
Map of 1860 Summerland Avenue, Winter Park, FL 32789
Listing Courtesy Of: Compass Florida Llc
jsloan2000@earthlink.net