Winter Park Lakefront Properties

55 TRISMEN (LOTS 7, 8 & 9) WINTER PARK FL 32789
$6,195,000

  • 4 Bedroom(s)
  • 6 Bathrooms
  • Living Area: 6,690 SqFt
  • Lot Size: 1.5 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 1955
  • Sub: osceola shores sec 01
  • 261014339

Presenting to the market for the first time in 54 years and the first time ever as three properties combined over the years all within footsteps of Park Avenue and situated on Lake Osceola. Exquisite estate resting on three waterfront lots totaling apprx 1.5 acres of land that introduces you to luxury living with endless possibilities. This “park-like” incredible property can be kept as one large estate or 1 of the waterfront lots could be split off creating 2 oversized lakefront and/or canal properties. Among the offerings are a four-bedroom main house with five baths, along with a separate one-bedroom, one-bath guesthouse. Encapsulated by gorgeous greenery and lush landscape, the property resembles a perfect blend of elegance and seclusion. Natural light floods the interior through floor-to-ceiling windows and glass doors. The master suite invites you to unwind and relax, featuring a spa-like bath with dual vanities, a separate shower and a generous walk-in closets. Tropical tranquility awaits outside with a palatial pool and sitting area surrounded by natural beauty. Make your way to the guesthouse, comprised of soaring wood ceilings and an abundance of casement windows. A boater’s haven, this residence offers a boathouse and dock on Lake Osceola, allowing you to set sail from your own backyard. Further features include natural gas service, three tankless hot water heaters, five air-conditioning units in the main house and one in the guesthouse, whole house generator, as well as an oversized two-car garage with motor court. This wonderful home has been lovingly maintained over the decades with well designed additions/renovations and magnificent grounds/landscaping... Encompassing nearly 8,000 total square feet upon 1.5 spacious acres, this lakefront gem is a picturesque paradise just waiting for your arrival.

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55 TRISMEN (LOTS 7 & 8) WINTER PARK FL 32789
$5,195,000

  • 4 Bedroom(s)
  • 6 Bathrooms
  • Living Area: 6,690 SqFt
  • Lot Size: 0.89 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 1955
  • Sub: osceola shores sec 01
  • 261014339

Presenting to the market for the first time in 54 years and on a double lot with approximately 200 feet of water frontage within footsteps of Park Avenue, situated on Lake Osceola. Exquisite estate resting on two waterfront lots that introduce you to luxury living with endless possibilities. This park-like, incredible property can be kept as one expansive lakefront estate. The main residence is a four-bedroom home with five baths, along with a separate one-bedroom, one-bath guest house. Encapsulated by gorgeous greenery and lush landscape, the property resembles a perfect blend of elegance and seclusion. Natural light floods the interior through floor-to-ceiling windows and glass doors. The master suite invites you to unwind and relax and features a spa-like bath with dual vanities, a separate shower and a generous walk-in closet. Tropical tranquility awaits outside with a palatial pool and sitting area surrounded by natural beauty. Make your way to the guesthouse, comprised of soaring wood ceilings and an abundance of casement windows. A boater’s haven, this residence offers a boathouse and dock on Lake Osceola, allowing you to set sail from your backyard. Further features include natural gas service, three tankless hot water heaters, five air conditioning units in the main house and one in the guest house, whole house generator, as well as an oversized two-car garage with a motor court. This magnificent property has been lovingly maintained over the decades with well-designed additions and renovations, and magnificent grounds and landscaping. Encompassing nearly 8,000 total square feet on approximately an acre of property, this lakefront gem is a picturesque paradise just waiting for your arrival.

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171 GENIUS WINTER PARK FL 32789
$4,500,000

  • 4 Bedroom(s)
  • 6 Bathrooms
  • Living Area: 5,326 SqFt
  • Lot Size: 0.78 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 2000
  • Sub: ardmore
  • 261014339

An exquisite Chain of Lakes offering awaits the most discerning of lakefront homebuyers in the heart of Winter Park. Being presented for the first time on the market, this meticulous masterpiece was built by Carlos Posada and boasts authentic Charleston architecture with the utmost attention to detail throughout. The main home has 4270 square feet and the bonus room over the garage has an additional 966 square feet. Upon arrival, you are greeted by a beautiful brick paver driveway that winds through lush landscaping with a mature tree canopy and gorgeous greenery. The solid mahogany double entry doors invite you inside to a gracious interior flooded with natural light. Complemented with reclaimed gorgeous hardwood flooring throughout, the first floor is comprised of spacious living areas that are perfect for entertaining. The gourmet kitchen welcomes the chef in the family with inset cabinetry, a 60-inch Viking range, a large island with seating and a spacious dining area with a fireplace. A separate dining area is just down the hall for more formal occasions with doors opening to a fabulous private courtyard with a fountain. Family and friends can gather in the great room, adorned with built-ins and a wall of windows and doors that offer awe-inspiring views of the pool and lake. Retreat to the first-floor master suite, a secluded escape with French doors that lead to the outside, along with a spa-like master bath complete with dual vanities, a soaking tub and a separate double-head shower. With three more bedrooms and an open loft upstairs, there is plenty of room to accommodate family and friends. Meanwhile, recreation abounds with a bonus room over the three-car garage. Complete with a full bath and private entry, this space offers plenty of entertainment flexibility or would work well as an additional, private fifth-bedroom suite. Further features include a side entry with a mudroom and a large laundry room. An opulent oasis, the sprawling backyard (arguably the best lot with a deeper peninsula on the eastern shore of Lake Mizell) encompasses a paver patio with a seating area and overlooks the stunning pool area. The stunning scenery is enhanced with lovely lake views and a boat dock on the water. Ideally situated on Lake Mizell and set back from the street, this home is adjacent to the Windsong community but is one of only four lakefront properties without the HOA obligation. For your picturesque piece of paradise, this remarkable residence embodies luxury living at its finest.

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1210 ALBERTA WINTER PARK FL 32789
$3,495,000

  • 4 Bedroom(s)
  • 6 Bathrooms
  • Living Area: 5,449 SqFt
  • Lot Size: 0.7 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 1991
  • Sub: osceola summit
  • 261014339

An exquisite European retreat on nearly an acre with lake frontage featuring a private dock, across the street, on Lake Osceola on the Winter Park Chain of Lakes. This location is unmatched in privacy, in one of the most pristine areas of Winter Park a short distance to Park Avenue and is situated on a double lot tucked away on a dead-end street. A meandering brick walking path leads you the recently renovated lakefront boat dock with plenty of room for entertaining or just soaking in the gorgeous sunsets. This custom home enjoys nearly 5,500 sf and many possibilities to make the function suit your family, boasting 4-5 bedrooms, downstairs master and additional first floor guest or mother-in-law suite. In addition, formal dining, living spaces with hardwood floors and an open kitchen family plan with doors to the covered porch, pool and a generous backyard as the back lot was acquired by previous owner and maintains a separate address. A expansive island is the focal point of kitchen with exotic granite counters, WOLF stainless appliances eat-in kitchen area and travertine floors. Outdoor living features beautiful slate decking, a breezy lanai, pool/spa a summer kitchen with additional side patio all add to the elegant lifestyle. The property is surrounded by detailed brick wall adding to the beauty of the grounds. The details are endless with meticulous craftmanship in the intricate moldings, volume detailed ceilings, hardwood floors, main & back staircases, slate roof & 3 masonry gas fireplaces with hand carved marble mantle in master. A 3–way split plan offers incredible privacy for all. 3-car garage with 2 circle driveways, perfect set-up for entertaining, is just more reasons to make this your home. This is a rare offering call today for a private showing.

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2615 OGLESBY WINTER PARK FL 32789
$2,600,000

  • 7 Bedroom(s)
  • 8 Bathrooms
  • Living Area: 6,700 SqFt
  • Lot Size: 1.13 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 2015
  • Sub: dudsdread heights
  • 51957E

Luxury lakefront custom home awaits. This Parade of Homes winner features spacious open floor plan with great attention to detail. Large gourmet kitchen opens to spacious great room with fireplace. Large lanai with summer kitchen , phantom screens, fireplace, and beautiful lake views. Heated pool and spa add to the resort ambiance. Private dock and custom boathouse make for fun days on the water. This custom estate boosts a gated entry, private guest wing with 3 bedrooms, 2 baths, full kitchen, and private garage. Great location close to Dubsdread Golf Course, College Park, and Park Avenue.

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21 KILLARNEY WINTER PARK FL 32789
$2,495,000

  • 5 Bedroom(s)
  • 5 Bathrooms
  • Living Area: 5,077 SqFt
  • Lot Size: 0.4 acs.
  • Status: Pending
  • Pool: Yes
  • Year Built: 2018
  • Sub: glencoe sub
  • 56037

WINTER PARK LAKEFRONT LUXURY LIVING!!!! The newest addition to the active Winter Park Lakefront Luxury Home market has just arrived! This exquisite, large, lakefront pool home with covered boat dock is a breathtaking collaboration by Andy Katzman (RARE Builders) and John Drake (Green Apple Architecture). This 5077 sq ft 5 bedroom, 5 bath is the crowning Jewel of Lake Killarney! Offering not only superior function but also authentic modern/transitional aesthetic, with an incredibly well thought out floor plan, unique living areas, stunning high end finishes and great attention to detail. Remarkable marble, quartz, wood, and limestone throughout! This exceptional design with expansive use of glass and great attention to sight lines has resulted in an awe-inspiring bright, open and airy space with picturesque views of beautiful Lake Killarney from almost every main room in the house, and a floor plan that is flooded with natural light! Home boasts a tremendous kitchen, dining, family room combo that anchors the entire floor plan and leads out to the covered patio area overlooking the lake and out to the heated salt water pool, spa and outdoor kitchen, making this entire area a spectacular natural extension of the interior living space presenting one of the most beautiful Winter Park Lake views. Walk past the pool and across the yard to the private covered boat dock with lift. Take in the view, or take the boat out and enjoy lake life on one of Central Florida's best private lakes offering great water sports, fishing, cruising. Boat over to fantastic Winter Park dining, grocery, and shops on the other side of the lake! Home is prominently sited on a great lot and steals the show when viewed from the lake! In addition to a very well appointed chef's kitchen, a rare expansive butler’s pantry with sink and dishwasher station, a wet bar, private second dining area, and a luxurious master suite with private access to the entire second floor balcony overlooking the pool and lake...you will love some of the less common additional spaces. Very rare large fitness room surrounded by glass with cathedral ceilings and unbelievable lake views. An inspiring home gym area! Good size second floor loft, a massive 5th bedroom (254 sq ft)/flex space/multi purpose room that offers hard to come by additional space for multiple potential applications. An additional office nook adjacent to master. All main bedrooms have direct access to full bathrooms! Full laundry room on both levels! Exterior of home is dramatic, refined and timeless. Beautiful architectural features such as the clever use of multiple arches and French doors, combined with brick, add considerable interest and appeal to this striking design! Eye catching contrasting dark tile roofs complete the composition! Green space in rear and large 3 car garage! This is a great opportunity to own a spectacular lakefront home in one of the most convenient locations in Winter Park. Minutes to Florida Hospital Orlando, and within 15 minutes of other community hospitals in Central Florida. Very close proximity to DT Orlando, Winter Park Village, Park Avenue shopping district and you are on and of I-4 in 2 minutes! WOW! WINTER PARK LAKEFRONT LIVING AT IT S BEST!

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515 LAKE FRONT WINTER PARK FL 32789
$2,385,000

  • 4 Bedroom(s)
  • 4 Bathrooms
  • Living Area: 4,023 SqFt
  • Lot Size: 0.4 acs.
  • Status: Pending
  • Pool: Yes
  • Year Built: 2002
  • Sub: lords sub
  • 261016736

Breathtaking Lakefront home on Lake Killarney!! A slice of paradise in the heart of sought after Winter Park. This custom home has a touch of Mediterranean flair built by Arthur Rutenberg. This home has been completely remodeled into an exquisite "Transitional Style" home. An noriginal by Arthur Rutenberg, custom home features a bright open floor plan with luxurious interior layout that boasts lake views from every room in the house. Included in the remodel was the removal of walls that impeded the lake views and a complete re-design of the master bedroom suite, including the master bath and closet! As you enter the home, you are met with a soaring 2-story entry that looks directly out to the lake. New wood floors throughout the main floor, high ceilings and a dramatic iron staircase are only a few of the features. The kitchen is open to oversized great room, exotic granite counter tops, a massive island with up lighting. Stainless steel appliances including double ovens. Formal dining & 2 owners retreats on main w/sitting areas offer spectacular views of the lake. The remodel offers beautiful vanities, walk-in showers & spacious walk-in closets w/custom cabinets. Two oversized bedrooms up w/Jack & Jill bath & dual sinks also offer lake views. Loads of windows & pocket slider doors across the back of home lead out to covered lanai, outdoor kitchen & screened in pebbletec pool w/fountain overlooking beautiful sunsets! A Picture perfect lot includes massive 100 ft of water frontage on 240 acre spring fed, ski-able & fly in private lake that accommodates all water sports. Water and power were run to the newly constructed dock and boat lift. Tile roof & circular driveway w/3 car side entry garage gives stunning curb appeal. A new HVAC unit was installed serving the master bedroom side of the house, a new hot water heater and a Generac generator was added to protect against power outages. A custom pet run complete with artificial pet turf, pet doors and security fence on the side of the house is another wonderful feature to this home. Absolutely no expense spared in this remodeled home. Boat/paddle board across lake to a variety of shops, restaurants, catch that 6 pound bass you always dreamed of. Just mins from downtown Winter Park, Rollins College & all the best healthcare you could find, what more could you ask for? Enjoy Lakefront living at its finest!!

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275 STIRLING WINTER PARK FL 32789
$2,300,000

  • 3 Bedroom(s)
  • 3 Bathrooms
  • Living Area: 3,046 SqFt
  • Lot Size: 0.5 acs.
  • Status: Pending
  • Pool: No
  • Year Built: 1977
  • Sub: virginia heights
  • 261012316

This home is being sold is AS IS condition. Seller can provide plans for the renovation work that is proposed. Lowest priced Chain of Lakes property in Winter Park

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4245 BEAR GULLY WINTER PARK FL 32792
$2,150,000

  • 5 Bedroom(s)
  • 5 Bathrooms
  • Living Area: 5,528 SqFt
  • Lot Size: 0.67 acs.
  • Status: Active
  • Pool: Yes
  • Year Built: 2018
  • Sub: sandy shores
  • 282013670

Entertain! Entertain! Entertain! Beautiful 2018 Custom built Winter Park lake front home on one of the most desired lakes in the area. This home features all the amenities for entertaining inside and outside by the pool that overlooks the Beautiful ski lake. This grand home was built with only the highest of quality fixtures from top to bottom. All concrete exterior construction with every upgrade possible. Enormous Gourmet kitchen with top of the line built in appliances just around the corner from the luxurious bar that is only seen in the finest hotels. Virtually every room in the house has a fantastic view of the secret oasis in the back yard . It is Winter Park’s secret location with access to incredible restaurants , top rated schools, and easy access to expressway to get you anywhere in the Orlando area within minutes. This home will make you say WOW when you view the amenities.

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1840 FAWSETT WINTER PARK FL 32789
$1,895,000

  • 5 Bedroom(s)
  • 5 Bathrooms
  • Living Area: 4,129 SqFt
  • Lot Size: 0.58 acs.
  • Status: Pending
  • Pool: Yes
  • Year Built: 1998
  • Sub: forest hills
  • 55779

WINTER PARK LAKEFRONT – Spectacular Lake Sue Waterfront home minutes from Park Avenue! 5 Bedrooms + Guest Apartment, pool/spa, outdoor kitchen, boathouse & full house generator – this home has it all! Luxurious interior layout features formal living and dining, hardwood floors, high ceilings, crown moldings and an open family room off the kitchen. Gourmet kitchen offers high-end appliances including a Subzero refrigerator, Bosch dishwasher, Viking range & grill, custom cabinetry, and granite counters. Downstairs guest bedroom with full bath is ultra-convenient for visiting friends and family. Upstairs is an overly spacious master suite with a Juliet balcony that overlooks beautiful Lake Sue. Master bath comes with his and her walk-in closets, a double sink vanity, jetted tub, and large walk-in shower. Above the garage you’ll find a bonus room with a full bath, perfect for use as a home office or guest apartment. Enjoy relaxing in the privacy of your own backyard; covered lanai with summer kitchen, travertine laid pool deck, salt water pool, and sun deck all contribute to living the ideal Florida lifestyle. Numerous upgrades and amenities are included with this home: Natural gas, slate tile roof, updated windows and plumbing, plantation shutters throughout the home, and more! Located just a short walk to Park Avenue, this gorgeous home sits in one of Winter Park’s most desirable neighborhoods, surrounded by picturesque, tree-lined brick streets and stunning estate homes.

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2023 VENETIAN WINTER PARK FL 32789
$1,700,000

  • 4 Bedroom(s)
  • 4 Bathrooms
  • Living Area: 3,326 SqFt
  • Lot Size: 1.08 acs.
  • Status: Pending
  • Pool: Yes
  • Year Built: 1964
  • Sub: na
  • 55779

Fantastic waterfront opportunity in Winter Park’s The Vias. This 1.08 acre lot features 140’ of frontage on Lake Maitland’s quiet lagoon and easy access to the Chain of Lakes. The oversized lot is about 140’ wide and about 230’ deep providing endless possibilities for the home of your dreams. Originally built in 1964 the existing home features a cool mid-century vibe with an extensive great room, kitchen, and dining room that have been added on to the back of the home maximizing the water views. Down the hall off the front foyer entry are three bedrooms, two full baths, and the laundry room. The large master bedroom, split from the other bedrooms, has two walk-in closets and a sizeable master bath area. In the center courtyard is the inground pool with views and access to the backyard and lake. Views of the lake are unobstructed from the home. As the backyard is a flat, clear green space. Located in one of Winter Park’s highly desirable neighborhoods, this home is located just minutes from the Winter Park Racquet Club, Interlachen Golf & Country Club, and a short drive to Park Avenue shops and dining. Zoned for A-rated Dommerich Elementary, Maitland Middle, and Winter Park High.

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4355 GABRIELLA WINTER PARK FL 32792
$1,340,000

  • 4 Bedroom(s)
  • 3 Bathrooms
  • Living Area: 2,620 SqFt
  • Lot Size: 1.88 acs.
  • Status: Pending
  • Pool: Yes
  • Year Built: 1973
  • Sub: acreage & unrec
  • 55779

Extraordinary opportunity to live on a 1.88 acre lot directly on the banks of Bear Gully Lake with breathtaking views. This secluded lakeside retreat located in one of Winter Park’s most desirable neighborhoods boasts 100+ feet of shoreline on a skiable lake. Upon entry the foyer opens to a light and airy, inviting living room with large wood burning fireplace. You are immediately drawn to the expansive sliding glass doors leading to the screened enclosed multi-level deck, pool, spa and outdoor fire pit for those chilly Florida nights. The four bedroom, 3 full baths, split plan offers unobstructed views of the lake from multiple rooms throughout the home. The heart of the home is the gourmet kitchen featuring custom wood cabinets, a gas range with pot filler, and a large middle island that overlooks the pool and lake through the pass-through window. Stainless steel appliances include a wine refrigerator and wine rack. Porcelain tile floors throughout. This is the ideal setting for privacy, serenity, and entertaining. Recent improvements in 2020 include new multi-slip dock, roof, wide paver driveway, travertine stone entry, landscaping.

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1807 BARKER WINTER PARK FL 32789
$1,189,000

  • 5 Bedroom(s)
  • 3 Bathrooms
  • Living Area: 3,804 SqFt
  • Lot Size: 0.4 acs.
  • Status: Active
  • Pool: No
  • Year Built: 2004
  • Sub: south lakemont shores
  • 51588

Classic lakefront home in Winter Park, 32789! Experience the tranquility and extraordinary views of the protected natural habitat across the lake. The far shoreline of Lake Spier is and will remain undeveloped, and this home has the most perfect view in town. Rediscover the joys of nature right in your own backyard! Custom-built in 2004 by Bill Felkel, this home remains loved by the original owners. With 3,800+ SF, the ideal floorplan includes a downstairs main suite, a 2nd bedroom (currently used as an office), a 2nd full bathroom, and an expansive kitchen & family room wrapped in newer windows and fresh interior paint (2020). The spacious main suite includes a sitting area, 2 walk-in closets, and French doors that lead to the screened-in back porch. Downstairs boasts all-natural, hardwood floors, crown molding, 10-foot ceilings, and a wood burning fireplace with a gas starter. The kitchen features a breakfast bar at the island, double oven, enormous walk-in pantry/storage area, and an open dinette area with stunning lake views. Upstairs, you will find 3 bedrooms with large closets, 1 full bathroom, a bonus room, & a finished attic storage room (15x10). The storage is unbelievable! According to water management research, Lake Spier is one of the cleanest, spring fed lakes in Winter Park...fish for bass from your dock or boat, paddle board/canoe/kayak across the lake, or just float/swim in the clear, cool waters. The location is incredibly convenient: close to Baldwin Park and it's shops, restaurants, outdoor events, and biking/walking path around Lake Baldwin. It is 2 blocks from Glenridge Middle School, and 1 block from the dog park. With numerous, breathtaking lake views, this is simply Florida living at its best! Ask the Realtor for the floorplan & survey attached in the MLS, and please locate the link to take the virtual tour!

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