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1821 Killarney Drive, Winter Park

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

6 Beds ⋅ 9 Baths ⋅ --- SubDv. ⋅ 32789 Zip Code

Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully connected by covered walkways, including five garages (three-car and two-car) and two motor courts, a detached office or seventh bedroom suite, and a lakeside pool cabana, creating a seamless blend of function, elegance and architectural harmony in this one-owner Lake Maitland residence. A dramatic arrival sets the tone as a flowing water feature guides guests along the walkway to the front entry. Inside, the grand foyer opens to a breathtaking gathering room, anchored by soaring two-story windows that frame panoramic lake views, the expansive terrace and terraced outdoor space. A dedicated space for a grand piano enhances the home’s capacity for elegant entertainment and memorable gatherings. The spacious kitchen overlooks the family room and is positioned alongside a dedicated bar, breakfast room and dining room. The family room, warmed by a gas fireplace, is filled with natural light and opens through a wall of French doors to the open terrace, blurring the line between indoor and outdoor living. The first-floor primary suite is a serene retreat with French doors to a covered outdoor space, a fireside sitting area wrapped in custom bookshelves, and a spa-inspired bath featuring a large glass shower, soaking tub, expansive walk-in closet, and a versatile flex room ideal for yoga, massage or expanded wardrobe space. A full guest suite with en-suite bath and walk-in closet is also on the main level. Upstairs, a grand mezzanine overlooks the gathering room, offering a dramatic extension of the living areas. French doors open to a front balcony, while the west wing features two bedrooms with a shared private living room and full bath. The east wing hosts two additional bedroom suites, each with walk-in closets and en-suite baths, one enhanced by a private sitting area and access to a spacious rear balcony. Off the kitchen, a wrought-iron gate leads to the basement level, where a refrigerated wine cellar, theater room, and generous storage space await. Outdoors, the stunning terrace showcases a heated spa, sparkling lakeside pool, expansive gas fire pit and an extraordinary 700-square-foot pool cabana that offers a wraparound screened porch with summer kitchen, a full bar, gaming area and full bath, ideal for lakeside entertaining. Elevated above the water for commanding views and shielded from the main road for complete privacy, this remarkable estate is a masterpiece, designed for multi-generational living and destined to create lasting memories for generations to come.

2203 Via Tuscany, Winter Park

$237,500

Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool overlooking the water. This rare 2-bedroom, 2-bath residence offers stunning lake views from the living room, bedroom, and private balcony, creating a peaceful retreat you’ll love coming home to. The home features thoughtful upgrades throughout, including a beautifully updated kitchen with upgraded appliances, induction range with air fryer, soft-close cabinetry and drawers, and a large pantry closet. Crown molding and recessed lighting enhance the space and highlight the luxury vinyl plank flooring throughout. Additional improvements include a new A/C system and tankless water heater, helping to keep the home energy efficient. The community also offers two on-site laundry facilities with private storage units for added convenience. Perfectly situated in highly desirable Winter Park, you’re just minutes from shopping, dining, and everyday essentials. This quiet lakeside community is only steps away from your favorite coffee shop or a casual evening drink. Wake up to lake views, unwind on your private balcony, and enjoy the relaxed Winter Park lifestyle you’ve been dreaming of. Opportunities like this are rare—schedule your private showing today and experience Lake Killarney living for yourself.

2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Attention lake enthusiasts! This is your opportunity to enjoy true waterfront living without the cost or maintenance typically associated with it. Located on beautiful Lake Killarney in sought-after Winter Park you will enjoy an array of amenities including a private boat ramp, a large open boat dock where you can feed the fish and turtles, picnic areas, clubhouse and resort style community pool overlooking the water. This rare 2-bedroom, 2-bath residence offers stunning lake views from the living room, bedroom, and private balcony, creating a peaceful retreat you’ll love coming home to. The home features thoughtful upgrades throughout, including a beautifully updated kitchen with upgraded appliances, induction range with air fryer, soft-close cabinetry and drawers, and a large pantry closet. Crown molding and recessed lighting enhance the space and highlight the luxury vinyl plank flooring throughout. Additional improvements include a new A/C system and tankless water heater, helping to keep the home energy efficient. The community also offers two on-site laundry facilities with private storage units for added convenience. Perfectly situated in highly desirable Winter Park, you’re just minutes from shopping, dining, and everyday essentials. This quiet lakeside community is only steps away from your favorite coffee shop or a casual evening drink. Wake up to lake views, unwind on your private balcony, and enjoy the relaxed Winter Park lifestyle you’ve been dreaming of. Opportunities like this are rare—schedule your private showing today and experience Lake Killarney living for yourself.

2500 Lee Road Unit 228, Winter Park

$1,100,000

Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and historic soul. This home has views and access to Lake Maitland and the Winter Park Chain of Lakes. The unit was completely renovated in 2020 by Zoltan Custom Homes, and all of the designer finishes were done with intention. Engineered wood flooring runs throughout, setting a warm, modern tone that pairs beautifully with the clean architectural lines. The chef's kitchen anchors the space with a soap stone waterfall island, custom white oak cabinetry, and Thermador appliances, creating a seamless flow to the living area. There are Sonos speakers featured in the ceiling throughout the unit. This space was meant for both everyday living and entertaining. Natural light pours in, allowing you to soak in the beautiful lake views. Sunsets in this condo are a true dream. The primary suite offers a retreat-like setting with a large walk-in closet and a spa-like bathroom featuring elegant marble finishes, porcelain flooring, and a free-standing tub. The secondary bedroom has been intelligently designed as a convertible office with a built-in Murphy bed and a closet featuring built-ins and great storage. This room can be suitable for full-time living, a dedicated office, or a wonderful guest room. Every detail has been thought out for functionality and aesthetic design. Located just steps from Kraft Azalea Gardens and Park Avenue, with access to the Winter Park Chain of Lakes, creating the perfect lifestyle. Only one boat slip is available at this time and is on first come first serve basis...The windows have all been restored in keeping with the historic building, but the seller added "Indow Window" inserts for quiet and energy efficiency.

2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

Perched on the top floor in the heart of Winter Park, this luxury, open-concept residence offers a rare blend of elevated design and everyday ease. Enjoy the peace of no neighbors above, plus the privacy, security, and lock-and-leave convenience that only condo living can provide without sacrificing space, light, or lifestyle. The Alabama delivers a rare Winter Park combo of modern living and historic soul. This home has views and access to Lake Maitland and the Winter Park Chain of Lakes. The unit was completely renovated in 2020 by Zoltan Custom Homes, and all of the designer finishes were done with intention. Engineered wood flooring runs throughout, setting a warm, modern tone that pairs beautifully with the clean architectural lines. The chef's kitchen anchors the space with a soap stone waterfall island, custom white oak cabinetry, and Thermador appliances, creating a seamless flow to the living area. There are Sonos speakers featured in the ceiling throughout the unit. This space was meant for both everyday living and entertaining. Natural light pours in, allowing you to soak in the beautiful lake views. Sunsets in this condo are a true dream. The primary suite offers a retreat-like setting with a large walk-in closet and a spa-like bathroom featuring elegant marble finishes, porcelain flooring, and a free-standing tub. The secondary bedroom has been intelligently designed as a convertible office with a built-in Murphy bed and a closet featuring built-ins and great storage. This room can be suitable for full-time living, a dedicated office, or a wonderful guest room. Every detail has been thought out for functionality and aesthetic design. Located just steps from Kraft Azalea Gardens and Park Avenue, with access to the Winter Park Chain of Lakes, creating the perfect lifestyle. Only one boat slip is available at this time and is on first come first serve basis...The windows have all been restored in keeping with the historic building, but the seller added "Indow Window" inserts for quiet and energy efficiency.

1602 Alabama Drive Unit 403, Winter Park

$4,800,000

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

5 Beds ⋅ 6 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

An extraordinary opportunity on the shores of Lake Osceola on one of Winter Park's most charming streets. This architecturally interesting lakefront estate offers breathtaking panoramic sunset views and an irreplaceable setting. Thoughtfully designed with the beautiful finishes. First time available in over three decades, this is rare chance to own a legacy property!

641 Bonita Drive, Winter Park

$184,900

Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

1 Beds ⋅ 1 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code

Lakefront Lifestyle in Winter Park—Under $200K! Live the resort life for less! This stunning, move-in ready retreat in the heart of Winter Park offers rare, direct access to the 239-acre, spring-fed Lake Killarney. Enjoy exclusive resident-only amenities, including a private boat launch, boat slips, an updated dock, and a tranquil lakefront gazebo. Perfectly located just minutes from the world-class shopping and dining of Winter Park Village, this home provides the ultimate balance of peaceful lakeside serenity and city convenience. The interior is just as impressive as the location. This charming, sun-drenched unit features an open-concept layout with gorgeous engineered wood flooring and a sleek kitchen upgraded with granite countertops. It’s a smart, stylish, and incredibly rare find that’s perfectly priced to sell. Whether you are looking for a low-maintenance home or a serene weekend getaway, this property delivers. Don't let this opportunity slip away—schedule your private showing today!

2500 Lee Rd. Unit 222, Winter Park

$2,600,000

Completed in 2020, this exceptional Winter Park lakefront estate blends refined architecture, thoughtful design, and effortless indoor-outdoor living on Lake Killarney. Beyond the gated courtyard-style entrance, the main residence offers 5 bedrooms, 4 full baths, and 2 half baths, complemented by a detached in-law studio ideal for guests, extended family, or a private home office, with a full bath, walk-in closet, and a dry bar with a mini refrigerator. Behind the home, the rear lawn stretches down to the lake where an oversized boat dock provides direct access to Lake Killarney for watersports or breathtaking sunset cruises. Enjoy a large deck, and an upgraded boat lift with 2 motors and a high-capacity cradle to accommodate a variety of boats. Throughout the home, a timeless neutral palette creates a warm and inviting space with modern elegance. An impressive open dining area greets you with soaring 2-story ceilings accented by exposed beams, and is adjoined to the kitchen by a well-appointed butler’s pantry for seamless hosting, complete with a dry bar and wine refrigerator, and a walk-in pantry. The kitchen is a true showpiece, with exceptional floor-to-ceiling cabinetry, 48” natural gas range with dual convection ovens, 2 dishwashers, and a built-in coffee/espresso machine. Anchoring the space, a large quartz-covered island offers 2 faucets plus a filtered water dispenser, and a butcher block prep space. The light-filled living room impresses with dramatic ceilings, a striking gas fireplace, and 10’ sliding glass doors that stack open to the covered lanai. A true extension of the home, the outdoor living experience is exceptional, featuring a summer kitchen, pool bath with an outdoor shower, and remote-controlled screens for year-round enjoyment. The resort-style pool and spa includes a sun shelf, all wrapped in travertine decking, overlooking the lake to provide a tranquil setting for relaxing with friends & family. Completing the main level is a private downstairs guest suite or home office, with a full bath and walk-in closet. Upstairs, the split-bedroom plan is separated by a versatile loft/bonus area with a dry bar and beverage fridge, ideal for a secondary living room, playroom, or study. Designed to embrace the home’s exceptional lakefront setting, the spacious primary retreat captures lake views through expansive glass doors, from the private balcony, and from the en-suite bath. The primary bath is luxurious, and thoughtfully designed to be a true sanctuary, with a freestanding soaking tub positioned to enjoy lake views, and a large glass-enclosed steam shower. Enjoy a very generous walk-in closet, with extensive built-ins and a center island that create a boutique-style dressing experience. The upper level also includes three additional bedrooms with wood floors, high ceilings, and easy access to 2 full bathrooms, plus a functional laundry room conveniently located off the bonus area. Perfectly positioned in Winter Park, with shopping, dining, and everyday conveniences just blocks away at the new and improved Winter Park Village, and the vibrant energy of the famed Park Avenue only minutes from your door, this lakefront home delivers the rare combination of newer construction and exceptional waterfront living—without compromise.

6 Beds ⋅ 7 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code

Completed in 2020, this exceptional Winter Park lakefront estate blends refined architecture, thoughtful design, and effortless indoor-outdoor living on Lake Killarney. Beyond the gated courtyard-style entrance, the main residence offers 5 bedrooms, 4 full baths, and 2 half baths, complemented by a detached in-law studio ideal for guests, extended family, or a private home office, with a full bath, walk-in closet, and a dry bar with a mini refrigerator. Behind the home, the rear lawn stretches down to the lake where an oversized boat dock provides direct access to Lake Killarney for watersports or breathtaking sunset cruises. Enjoy a large deck, and an upgraded boat lift with 2 motors and a high-capacity cradle to accommodate a variety of boats. Throughout the home, a timeless neutral palette creates a warm and inviting space with modern elegance. An impressive open dining area greets you with soaring 2-story ceilings accented by exposed beams, and is adjoined to the kitchen by a well-appointed butler’s pantry for seamless hosting, complete with a dry bar and wine refrigerator, and a walk-in pantry. The kitchen is a true showpiece, with exceptional floor-to-ceiling cabinetry, 48” natural gas range with dual convection ovens, 2 dishwashers, and a built-in coffee/espresso machine. Anchoring the space, a large quartz-covered island offers 2 faucets plus a filtered water dispenser, and a butcher block prep space. The light-filled living room impresses with dramatic ceilings, a striking gas fireplace, and 10’ sliding glass doors that stack open to the covered lanai. A true extension of the home, the outdoor living experience is exceptional, featuring a summer kitchen, pool bath with an outdoor shower, and remote-controlled screens for year-round enjoyment. The resort-style pool and spa includes a sun shelf, all wrapped in travertine decking, overlooking the lake to provide a tranquil setting for relaxing with friends & family. Completing the main level is a private downstairs guest suite or home office, with a full bath and walk-in closet. Upstairs, the split-bedroom plan is separated by a versatile loft/bonus area with a dry bar and beverage fridge, ideal for a secondary living room, playroom, or study. Designed to embrace the home’s exceptional lakefront setting, the spacious primary retreat captures lake views through expansive glass doors, from the private balcony, and from the en-suite bath. The primary bath is luxurious, and thoughtfully designed to be a true sanctuary, with a freestanding soaking tub positioned to enjoy lake views, and a large glass-enclosed steam shower. Enjoy a very generous walk-in closet, with extensive built-ins and a center island that create a boutique-style dressing experience. The upper level also includes three additional bedrooms with wood floors, high ceilings, and easy access to 2 full bathrooms, plus a functional laundry room conveniently located off the bonus area. Perfectly positioned in Winter Park, with shopping, dining, and everyday conveniences just blocks away at the new and improved Winter Park Village, and the vibrant energy of the famed Park Avenue only minutes from your door, this lakefront home delivers the rare combination of newer construction and exceptional waterfront living—without compromise.

560 Country Club Drive, Winter Park

$4,250,000

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in the main house plus a detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform Twelve kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool. A wood-clad pergola shelters the lanai. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$899,000

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

2 Beds ⋅ 2 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

Nestled on the shores of private, skiable Lake Killarney, this beautifully updated and absolutely adorable 2-bedroom, 2-bath home offers a rare opportunity to enjoy true lakefront living without the upkeep of a large estate. Perfect as a full-time residence, a weekend lake escape, a snowbird retreat, or even an income-producing short-term rental (as previously used by the current owners), this charming property delivers the ultimate blend of convenience, recreation, and Winter Park lifestyle. Wake up to serene water views, spend your days boating across crystal-clear Lake Killarney, and end each evening with breathtaking sunsets on the water. From your private dock, you can cruise straight over to Hillstone for happy hour or pull up to Trader Joe’s for a quick grocery run—the kind of effortless, magical living that only this lake can offer. Located just minutes from Park Avenue’s boutique shops, fine dining, and cultural attractions, this home feels worlds away while keeping you close to everything you love. Whether you're wanting to downsize and have low maintenance, a seasonal resident seeking a warm-weather sanctuary, or a local looking for the perfect weekend getaway to store your boat, this home delivers a lifestyle unlike anything else in Winter Park. A unique location, a turn-key home, and an unmatched lake experience; this Lake Killarney gem is a must-see and you won’t want to miss it.

560 Ololu Drive, Winter Park

$290,000

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

2 Beds ⋅ 1 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake Killarney. Inside, you’ll find a bright, natural light–filled living space with an intimate, inviting feel. The efficient galley kitchen flows seamlessly into the living and dining area, making the home feel larger than its square footage. A rare bonus for condo living, the home includes a separate laundry room, offering added convenience and additional storage. Step outside to your private patio space, perfect for morning coffee, quiet evenings, or creating your own cozy outdoor retreat. There’s even room for a foosball table, making it a great spot to unwind, entertain, or simply grab a Coke and smile as you enjoy the Florida breeze. Residents enjoy an impressive list of community amenities, including a sparkling private pool, lush green spaces, and access to Lake Killarney’s private community dock, ideal for launching kayaks and paddleboards, fishing, or taking in serene lakefront views. Enjoy evening sunset strolls, weekend boating, or a relaxing afternoon by the pool. The community also offers convenient on-site laundry facilities, beautifully maintained grounds, and a welcoming neighborhood atmosphere. With strong rental appeal, an unbeatable location, and timeless Winter Park charm, 151 N Orlando Ave #115 is an ideal choice for first-time buyers, downsizers, or investors seeking long-term value in one of Central Florida’s most desirable lakefront communities. Schedule your private showing today and experience the lifestyle waiting for you at Lake Killarney.

151 N Orlando Avenue Unit #115, Winter Park

$2,232,000

Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered lakefront patio, where you can enjoy al fresco meals and admire your boat in its personal covered slip with electric lift. The spacious kitchen offers new cabinetry, under-cabinet lighting, hardwood countertops, and a farmhouse sink. Built-in appliances include a Sub-Zero® Refrigerator, a Wolfe® Gas Cooktop, Dacor® Ovens, and a Bosch® Dishwasher. From the kitchen, you have access to the sizable adjacent library, with its wall-to-wall bookcases. Configure it as your office or a family room if you wish. A wall of glass doors and windows makes the lake a focal point in your primary bedroom suite. The en-suite bathroom features a jacuzzi bathtub, walk-in shower, two separate vanities, and a secluded Toto®-equipped water closet. A large walk-in closet completes the suite. Two more spacious bedrooms are on the opposite end of the residence. One includes its own en-suite full bathroom. Both share an outdoor patio space. Additionally, you’ll find a third full bathroom and a powder bathroom. The laundry room includes a Miele® washing machine and dryer set. In the secured garage, you have two assigned parking spaces and a sizeable storage room. Perle du Lac residents enjoy exclusive community amenities, including a heated swimming pool, hot tub, beautifully maintained grounds, and double-gated security for peace of mind. All of this is minutes from Park Avenue, Rollins College, and everything that makes downtown Winter Park famous.

3 Beds ⋅ 4 Baths ⋅ Perle Du Lac SubDv. ⋅ 32789 Zip Code

Imagine waking, relaxing, and entertaining with serene lakefront views in this elegant ground-floor Perle du Lac residence. The refined 2,714-square-foot design includes hardwood and travertine flooring, ten-foot-high ceilings, and extensive millwork. The expansive open-plan living and dining room lets you configure your furniture however you’d like. A bank of glass doors leads to your covered lakefront patio, where you can enjoy al fresco meals and admire your boat in its personal covered slip with electric lift. The spacious kitchen offers new cabinetry, under-cabinet lighting, hardwood countertops, and a farmhouse sink. Built-in appliances include a Sub-Zero® Refrigerator, a Wolfe® Gas Cooktop, Dacor® Ovens, and a Bosch® Dishwasher. From the kitchen, you have access to the sizable adjacent library, with its wall-to-wall bookcases. Configure it as your office or a family room if you wish. A wall of glass doors and windows makes the lake a focal point in your primary bedroom suite. The en-suite bathroom features a jacuzzi bathtub, walk-in shower, two separate vanities, and a secluded Toto®-equipped water closet. A large walk-in closet completes the suite. Two more spacious bedrooms are on the opposite end of the residence. One includes its own en-suite full bathroom. Both share an outdoor patio space. Additionally, you’ll find a third full bathroom and a powder bathroom. The laundry room includes a Miele® washing machine and dryer set. In the secured garage, you have two assigned parking spaces and a sizeable storage room. Perle du Lac residents enjoy exclusive community amenities, including a heated swimming pool, hot tub, beautifully maintained grounds, and double-gated security for peace of mind. All of this is minutes from Park Avenue, Rollins College, and everything that makes downtown Winter Park famous.

660 Osceola Avenue Unit 101, Winter Park

$6,111,000

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.

5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code

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.

1860 Summerland Avenue, Winter Park

$6,300,000

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

4 Beds ⋅ 6 Baths ⋅ Camwood SubDv. ⋅ 32789 Zip Code

Quintisential Lake Maitland Estate - first time available. Classic architecture with incredible and thoughtful details throughout. Private setting on over an acre captures sweeping views of Lake Maitland. Sought after location close to Park Avenue. This legacy property embodies the best of Winter Park Lakefront Living.

1308 Green Cove, Winter Park

$5,700,000

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

SOLD DATA ENTRY.. Welcome to this timeless lakefront estate located on the shores of Lake Virginia, offering approximately 143 feet of private waterfront along the highly sought-after Winter Park Chain of Lakes. Situated on over an acre, this beautifully updated residence blends classic architecture with modern luxury and an exceptional indoor-outdoor lifestyle. Thoughtfully renovated in 2016, the home features spacious formal and informal living areas, high ceilings, custom millwork, and stunning lake views throughout.The chef’s kitchen is equipped with Wolf and Sub-Zero appliances, double ovens, built-in Miele coffee system, wine refrigeration, and additional refrigerator/freezer drawers. The kitchen opens to the main living space and flows seamlessly to the outdoor entertaining areas. The primary suite offers a serene lakefront setting with a spa-inspired bath and generous closets. Additional bedrooms are well-appointed and offer both privacy and flexible living arrangements.Step outside to a resort-style waterfront setting, complete with a large pool and spa, expansive terrace, summer kitchen, gas fire pit, and private boat dock with lift. Enjoy boating, paddleboarding, or sunset cruises right from your backyard. The property’s elevation provides exceptional views stretching across Lake Virginia toward downtown Orlando and Rollins College.Located on a quiet, private street just moments from Park Avenue dining, shops, and Winter Park’s most desirable amenities, this is a rare opportunity to enjoy lakefront living in one of Central Florida’s most distinguished neighborhoods.

374 Henkel Circle, Winter Park

$2,925,000

This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid wood and travertine flooring throughout the first floor, surround sound speakers, a wood burning fireplace and freshly painted interiors. The living room features large windows overlooking the lake, with an open floor plan that flows seamlessly into the dining room and kitchen. The gourmet kitchen showcases a beamed ceiling, Busby custom three tone cabinetry with granite countertops, a six burner gas cooktop, and a built in ice maker. The dining area offers easy access to the outdoor entertaining spaces, perfect for enjoying lakeside gatherings. The primary suite occupies the entire second level, offering dual bathrooms, individual walk in closets, and a private balcony with unobstructed lake views. Additional features include an inviting office/den with french doors and custom built ins, as well as a spacious laundry room with ample cabinetry, a 120 bottle wine fridge, and a secondary refrigerator for added convenience. An expansive paver driveway leads to covered parking that accommodates up to three vehicles. Traditional gas lanterns and built in landscape lighting enhance the home’s Mediterranean charm and highlight its mature, manicured grounds. Outdoor living is the centerpiece of this property, featuring durable composite board decking, a summer kitchen with an infrared grill, and a hot tub for relaxing and entertaining. Enjoy multiple inviting seating areas with stunning east facing lake views. The private boat dock includes a storage closet, boat lift, and the boat itself is included. This home offers relaxed luxury and timeless lakefront living in one of Winter Park’s most desirable neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Thomas M Henkels Add SubDv. ⋅ 32789 Zip Code

This beautiful Mediterranean style home offers a rare opportunity for prime waterfront living on Lake Mizell, part of the highly sought out after Winter Park Chain of Lakes. The property is just a short walk or drive to Park Avenue’s restaurants, boutiques, and local attractions. The main home features three bedrooms and five bathrooms, each bedroom offering its own en suite bathroom. A separate guest house (ADU) provides an additional 932 square feet with two bedrooms, one bathroom, newly refinished original hardwood floors, fresh paint and a wood burning fireplace perfect for guests or extended family. Inside the main residence, you’ll find solid wood and travertine flooring throughout the first floor, surround sound speakers, a wood burning fireplace and freshly painted interiors. The living room features large windows overlooking the lake, with an open floor plan that flows seamlessly into the dining room and kitchen. The gourmet kitchen showcases a beamed ceiling, Busby custom three tone cabinetry with granite countertops, a six burner gas cooktop, and a built in ice maker. The dining area offers easy access to the outdoor entertaining spaces, perfect for enjoying lakeside gatherings. The primary suite occupies the entire second level, offering dual bathrooms, individual walk in closets, and a private balcony with unobstructed lake views. Additional features include an inviting office/den with french doors and custom built ins, as well as a spacious laundry room with ample cabinetry, a 120 bottle wine fridge, and a secondary refrigerator for added convenience. An expansive paver driveway leads to covered parking that accommodates up to three vehicles. Traditional gas lanterns and built in landscape lighting enhance the home’s Mediterranean charm and highlight its mature, manicured grounds. Outdoor living is the centerpiece of this property, featuring durable composite board decking, a summer kitchen with an infrared grill, and a hot tub for relaxing and entertaining. Enjoy multiple inviting seating areas with stunning east facing lake views. The private boat dock includes a storage closet, boat lift, and the boat itself is included. This home offers relaxed luxury and timeless lakefront living in one of Winter Park’s most desirable neighborhoods.

516 Henkel Circle, Winter Park

$1,700,000

An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area's private and pristine ski lakes with no public ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-one-half bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the existing home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park's desired private lakes.

Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

An exceptional opportunity to design and build your dream lakefront home in Winter Park. Positioned on the shores of Lake Berry, one of the area's private and pristine ski lakes with no public ramp, this property offers a rare combination of privacy, location and potential. Set on over a half-acre of lakefront land, the property features a four-bedroom, two-and-one-half bath, single-story residence with a covered boat dock, ideal for enjoying lake life immediately or while planning a future custom build. The northeast-facing front provides the ideal orientation to capture breathtaking sunsets across the water each evening. Whether you choose to renovate the existing home or build a new architectural masterpiece, this offering presents the ultimate canvas for creating a generational lakefront retreat. Within minutes of downtown Winter Park, Park Avenue and A-rated public schools, this property combines the best of convenience, serenity and luxury lakefront living. A special opportunity to bring your vision to life on one of Winter Park's desired private lakes.

633 Balmoral Road, Winter Park

$8,950,000

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

7 Beds ⋅ 11 Baths ⋅ Windsong-Preserve Point SubDv. ⋅ 32789 Zip Code

In the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean estate is a private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm and privacy rarely found in Winter Park. The home features seven spacious bedrooms and nine full and two half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood-burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its private gated entrance, this home is a one-of-a-kind opportunity to enjoy all the amenities Winter Park and Windsong have to offer.

1120 Preserve Point Drive, Winter Park

$2,250,000

This spectacular Winter Park lakefront home is a very rare find indeed - exquisite inside and out! This home has been meticulously renovated and offers all the allure of fine lakefront living and is just minutes from Park Avenue’s shopping, dining and cultural gems. Situated on an oversized .39 acre lot this residence enjoys a picture-perfect setting with long views of Lake Killarney. Superior craftsmanship and attention to architectural detail emanate throughout the 3,749 SqFt of living space. This impressive property features an inspired layout starting with the exquisitely designed public spaces and continues throughout the rest of the home. The spacious owner’s retreat offers large windows overlooking the lake, customized walk-in closets, and just completed $60K bath renovation with a large walk-in shower, luxurious fixtures & finishes. There are 3 additional bedrooms: one with an ensuite bath and two with a shared bath. Additional amenities include a great room with floor to ceiling windows overlooking the lake, stacked stone gas fireplace, 26’ vaulted ceiling; gourmet kitchen with custom cabinetry, top-of-the-line stainless appliances, walk-in pantry. Other features include: built-in cabinetry, stone and hardwood flooring; whole house generator, solar panels pay for all the current electrical usage, 2 new HVAC systems, 4 wine cooler towers (600 Bottles) and an oversized two-car garage with EV charger, epoxy floor and storage cabinetry. Enjoy lakefront living under a 450 SqFt covered porch with a chef-inspired summer kitchen, electric shades, stacked stone wood burning fireplace, wet bar, epoxy flooring, tongue & groove ceiling and just steps away is a 275’ SqFt (Not Included in SqFt) air-conditioned boathouse with a coffered wood ceiling, covered boat dock, and deck.

4 Beds ⋅ 4 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

This spectacular Winter Park lakefront home is a very rare find indeed - exquisite inside and out! This home has been meticulously renovated and offers all the allure of fine lakefront living and is just minutes from Park Avenue’s shopping, dining and cultural gems. Situated on an oversized .39 acre lot this residence enjoys a picture-perfect setting with long views of Lake Killarney. Superior craftsmanship and attention to architectural detail emanate throughout the 3,749 SqFt of living space. This impressive property features an inspired layout starting with the exquisitely designed public spaces and continues throughout the rest of the home. The spacious owner’s retreat offers large windows overlooking the lake, customized walk-in closets, and just completed $60K bath renovation with a large walk-in shower, luxurious fixtures & finishes. There are 3 additional bedrooms: one with an ensuite bath and two with a shared bath. Additional amenities include a great room with floor to ceiling windows overlooking the lake, stacked stone gas fireplace, 26’ vaulted ceiling; gourmet kitchen with custom cabinetry, top-of-the-line stainless appliances, walk-in pantry. Other features include: built-in cabinetry, stone and hardwood flooring; whole house generator, solar panels pay for all the current electrical usage, 2 new HVAC systems, 4 wine cooler towers (600 Bottles) and an oversized two-car garage with EV charger, epoxy floor and storage cabinetry. Enjoy lakefront living under a 450 SqFt covered porch with a chef-inspired summer kitchen, electric shades, stacked stone wood burning fireplace, wet bar, epoxy flooring, tongue & groove ceiling and just steps away is a 275’ SqFt (Not Included in SqFt) air-conditioned boathouse with a coffered wood ceiling, covered boat dock, and deck.

600 Ololu Drive, Winter Park

$3,200,000

Don't miss the opportunity to own this stunning lakefront property on Lake Sue in Winter Park! Over an acre with 125+ feet of frontage, private dock with lift, and breathtaking sunsets. Features include a chef’s kitchen, multiple entertaining spaces, spa, and expansive lake views. **New build plans by Winter Park Designs (Gary Hancock) and Urban Perch – A Boutique Home Builder – available upon request.

4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code

Don't miss the opportunity to own this stunning lakefront property on Lake Sue in Winter Park! Over an acre with 125+ feet of frontage, private dock with lift, and breathtaking sunsets. Features include a chef’s kitchen, multiple entertaining spaces, spa, and expansive lake views. **New build plans by Winter Park Designs (Gary Hancock) and Urban Perch – A Boutique Home Builder – available upon request.

1900 W Fawsett Road, Winter Park

$2,835,000

An incredible Winter Park Chain-of-Lakes opportunity on Lake Virginia with clear views of Rollins College. This transitionally designed home, situated in the highly coveted Virginia Heights, offers an opportunity like no other with proximity to Park Avenue coupled with the lakefront amenities through a Venetian canal system that uniquely connects five lakes and captures the quintessential Winter Park lifestyle. This four-bedroom three-and-a-half-bath home invites you into a two-story foyer surrounded by windows and natural light. The spacious kitchen features a mid-century tile backsplash, light cabinetry and a window out to the pool and lake. The main living space features a beautiful fireplace and back atrium that invites the stars and twinkling sunsets from the water. The separate dining room is spacious and there is an additional den or office space to round out the first floor. All bedrooms are upstairs and generously sized providing flexibility and the primary bedroom has the most incredible lakefront views. A clear water canal runs alongside the home and spills into lake Virginia adding to the ambiance of the backyard where nature abounds. Continue the existing renovation with your own style or build a house of your dreams. Impeccably located with shopping and dining at your fingertips as well as Rollins College. Fantastic schools with Audubon K-8 and Winter Park High. Don’t miss this one – call for your private tour.

4 Beds ⋅ 4 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

An incredible Winter Park Chain-of-Lakes opportunity on Lake Virginia with clear views of Rollins College. This transitionally designed home, situated in the highly coveted Virginia Heights, offers an opportunity like no other with proximity to Park Avenue coupled with the lakefront amenities through a Venetian canal system that uniquely connects five lakes and captures the quintessential Winter Park lifestyle. This four-bedroom three-and-a-half-bath home invites you into a two-story foyer surrounded by windows and natural light. The spacious kitchen features a mid-century tile backsplash, light cabinetry and a window out to the pool and lake. The main living space features a beautiful fireplace and back atrium that invites the stars and twinkling sunsets from the water. The separate dining room is spacious and there is an additional den or office space to round out the first floor. All bedrooms are upstairs and generously sized providing flexibility and the primary bedroom has the most incredible lakefront views. A clear water canal runs alongside the home and spills into lake Virginia adding to the ambiance of the backyard where nature abounds. Continue the existing renovation with your own style or build a house of your dreams. Impeccably located with shopping and dining at your fingertips as well as Rollins College. Fantastic schools with Audubon K-8 and Winter Park High. Don’t miss this one – call for your private tour.

255 Stirling Avenue, Winter Park

$1,600,000

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded with natural light from strategically placed skylights. Rich hardwood floors flow throughout, while French doors create seamless indoor-outdoor living. The dramatic great room captivates with distinctive brick flooring, copper-coated ceiling tiles, and an old-fashioned built-in bar—perfect for entertaining. The generously proportioned primary suite features an en suite with double sink vanity and walk-in shower. Two additional well-appointed bedrooms, each with full baths, provide comfort and privacy for the family and guests. The heart of the home centers on an expansive gourmet kitchen boasting dual sinks, premium stainless-steel appliances, solid wood cabinetry, and distinctive decorative tile countertops. A dedicated home office provides the perfect work-from-home sanctuary. Two inviting fireplaces create cozy gathering spaces throughout. The covered patio with ceiling fans extends living space outdoors, while the screened pool area offers private resort-style relaxation. The tile roof crowns this impressive estate with both beauty and durability. Whether you envision a stunning renovation showcasing the home's exceptional bones or a complete rebuild taking advantage of the prime waterfront location, this property represents a once-in-a-lifetime opportunity to create your Winter Park masterpiece.

3 Beds ⋅ 3 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

825 Palmer Avenue, Winter Park | $1,799,000 - A Rare Venetian Canal Treasure Awaits Your Vision! Discover an extraordinary opportunity on one of Winter Park's most coveted waterways. This exceptional single-story estate on Palmer Avenue presents over 3,200 square feet of pure potential, perfectly positioned on an oversized .35-acre lot (85x173') with exclusive boathouse access to the prestigious Venetian Canal and Winter Park Chain of Lakes. Steps from the sophisticated boutiques and world-class dining of Park Avenue, this rare find offers the ultimate Winter Park lifestyle where luxury meets convenience. The thoughtfully designed open floorplan showcases expansive living spaces flooded with natural light from strategically placed skylights. Rich hardwood floors flow throughout, while French doors create seamless indoor-outdoor living. The dramatic great room captivates with distinctive brick flooring, copper-coated ceiling tiles, and an old-fashioned built-in bar—perfect for entertaining. The generously proportioned primary suite features an en suite with double sink vanity and walk-in shower. Two additional well-appointed bedrooms, each with full baths, provide comfort and privacy for the family and guests. The heart of the home centers on an expansive gourmet kitchen boasting dual sinks, premium stainless-steel appliances, solid wood cabinetry, and distinctive decorative tile countertops. A dedicated home office provides the perfect work-from-home sanctuary. Two inviting fireplaces create cozy gathering spaces throughout. The covered patio with ceiling fans extends living space outdoors, while the screened pool area offers private resort-style relaxation. The tile roof crowns this impressive estate with both beauty and durability. Whether you envision a stunning renovation showcasing the home's exceptional bones or a complete rebuild taking advantage of the prime waterfront location, this property represents a once-in-a-lifetime opportunity to create your Winter Park masterpiece.

825 Palmer Avenue, Winter Park

$2,798,000

Stunning canal-front home, Winter Park Chain of Lakes. Welcome to this exceptional one-story residence in the heart of Winter Park, offering direct access to the desired Winter Park Chain of Lakes via the Venetian Canal. Built in 2018, this meticulously maintained home features four bedrooms, three baths, and 3,258 square feet of elegant living space designed for comfort and entertaining. The open floor plan showcases a large gourmet kitchen outfitted with custom cabinetry and generous counter space. Ideal for hosting gatherings or enjoying quiet evenings at home. Expansive windows throughout the home offer beautiful, tranquil views of the canal and lush, mature landscaping. Large screened-in lanai complete with a fully equipped summer kitchen and fireplace overlooking the canal and private boathouse.

4 Beds ⋅ 3 Baths ⋅ Palmer Park SubDv. ⋅ 32789 Zip Code

Stunning canal-front home, Winter Park Chain of Lakes. Welcome to this exceptional one-story residence in the heart of Winter Park, offering direct access to the desired Winter Park Chain of Lakes via the Venetian Canal. Built in 2018, this meticulously maintained home features four bedrooms, three baths, and 3,258 square feet of elegant living space designed for comfort and entertaining. The open floor plan showcases a large gourmet kitchen outfitted with custom cabinetry and generous counter space. Ideal for hosting gatherings or enjoying quiet evenings at home. Expansive windows throughout the home offer beautiful, tranquil views of the canal and lush, mature landscaping. Large screened-in lanai complete with a fully equipped summer kitchen and fireplace overlooking the canal and private boathouse.

1074 Mckean Circle, Winter Park

$380,000

One or more photo(s) has been virtually staged. Seller financing and lease to own options for qualified buyers. HOA fee covers full time building engineer, spectrum cable tv, phone and internet, water and sewer and amenities. Beautifully updated 2-bedroom, 2-bathroom lakefront condo (Lake Virginia Condo) in the heart of Winter Park, FL. Enjoy a prime location just steps from Park Avenue's charming shops, restaurants, Rollins College, scenic parks, and cultural museums. Freshly painted with new, water-resistant LVP flooring throughout. The refreshed kitchen features energy-efficient appliances, solid wood cabinetry, and ample storage. Expansive wall-to-wall sliding glass windows in the living room and primary bedroom brightens the space with natural light. Convenient in-unit washer/dryer closet and a screened-in back porch overlooking the serene canal connecting Lake Virginia and Lake Osceola. Building has guest suite, pool and spa, boat docks, lake access, common lounges, open patio and grilling area and much more. Some photos are virtually staged with furniture. Vacant and easy to show—contact your realtor to schedule a viewing today!

2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code

One or more photo(s) has been virtually staged. Seller financing and lease to own options for qualified buyers. HOA fee covers full time building engineer, spectrum cable tv, phone and internet, water and sewer and amenities. Beautifully updated 2-bedroom, 2-bathroom lakefront condo (Lake Virginia Condo) in the heart of Winter Park, FL. Enjoy a prime location just steps from Park Avenue's charming shops, restaurants, Rollins College, scenic parks, and cultural museums. Freshly painted with new, water-resistant LVP flooring throughout. The refreshed kitchen features energy-efficient appliances, solid wood cabinetry, and ample storage. Expansive wall-to-wall sliding glass windows in the living room and primary bedroom brightens the space with natural light. Convenient in-unit washer/dryer closet and a screened-in back porch overlooking the serene canal connecting Lake Virginia and Lake Osceola. Building has guest suite, pool and spa, boat docks, lake access, common lounges, open patio and grilling area and much more. Some photos are virtually staged with furniture. Vacant and easy to show—contact your realtor to schedule a viewing today!

690 Osceola Avenue Unit 209, Winter Park

$1,250,000

This is a rare opportunity to own a ONE STORY LARKEFRONT home on a HALF-ACRE lot in the highly desirable Via’s of Winter Park. Nestled on a quiet cul-de-sac in Tuscany Place and zoned for top A-rated schools, this beautifully maintained 4-bedroom, 2-bath home offers breathtaking views of Lake Temple from nearly every room. The spacious and light-filled interior features a split bedroom floor plan with a formal living room, dining room, and a comfortable family room—an ideal layout for any family. The kitchen is equipped with solid wood cabinets, granite countertops, and opens to the family room, which includes custom built-ins and a wood-burning fireplace with granite surround. Hardwood floors run throughout the home, and large windows flood the space with natural light. The primary suite overlooks the lake and includes a walk-in closet, dual sinks, a separate shower, and direct access to the screened-in rear porch. Three additional guest bedrooms are privately situated on the opposite side of the home. A spacious indoor laundry room leads to a side-entry two-car garage. Outside, the screened patio offers the perfect place to entertain while enjoying the pool, spa, and serene lakefront setting. Located just minutes from Park Avenue and the Winter Park Racquet Club, this unique property offers endless potential to live in as-is, renovate, or build new on one of the Via’s most coveted lakefront lots.

4 Beds ⋅ 2 Baths ⋅ Tuscany Place First Add SubDv. ⋅ 32789 Zip Code

This is a rare opportunity to own a ONE STORY LARKEFRONT home on a HALF-ACRE lot in the highly desirable Via’s of Winter Park. Nestled on a quiet cul-de-sac in Tuscany Place and zoned for top A-rated schools, this beautifully maintained 4-bedroom, 2-bath home offers breathtaking views of Lake Temple from nearly every room. The spacious and light-filled interior features a split bedroom floor plan with a formal living room, dining room, and a comfortable family room—an ideal layout for any family. The kitchen is equipped with solid wood cabinets, granite countertops, and opens to the family room, which includes custom built-ins and a wood-burning fireplace with granite surround. Hardwood floors run throughout the home, and large windows flood the space with natural light. The primary suite overlooks the lake and includes a walk-in closet, dual sinks, a separate shower, and direct access to the screened-in rear porch. Three additional guest bedrooms are privately situated on the opposite side of the home. A spacious indoor laundry room leads to a side-entry two-car garage. Outside, the screened patio offers the perfect place to entertain while enjoying the pool, spa, and serene lakefront setting. Located just minutes from Park Avenue and the Winter Park Racquet Club, this unique property offers endless potential to live in as-is, renovate, or build new on one of the Via’s most coveted lakefront lots.

1049 Tuscany Place, Winter Park

$1,250,000

This rare opportunity to own a ONE STORY LAKEFRONT home on A HALF ACRE lot located in the highly desirable Via’s of Winter Park. Tuscany Place is nestled on a quiet cul-de-sac and zoned for top A-rated schools. Close to Park Ave and the Winter Park Racquet Club, This one-of-a-kind ½ acre LAKEFRONT lot in the Winter Park Via’s is unique and rare find. Don’t miss this amazing opportunity to live and/or build in the Vias!

Tuscany Place First Add SubDv. ⋅ 32789 Zip Code

This rare opportunity to own a ONE STORY LAKEFRONT home on A HALF ACRE lot located in the highly desirable Via’s of Winter Park. Tuscany Place is nestled on a quiet cul-de-sac and zoned for top A-rated schools. Close to Park Ave and the Winter Park Racquet Club, This one-of-a-kind ½ acre LAKEFRONT lot in the Winter Park Via’s is unique and rare find. Don’t miss this amazing opportunity to live and/or build in the Vias!

1049 Tuscany Place, Winter Park

$5,225,000

An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors flood the interiors with natural light and deliver unobstructed panoramic lake views from nearly every room. Enter through a dramatic 12-foot glass pivot door into a 21-foot-long art gallery foyer adorned with a sculptural linear chandelier and Venetian plaster walls and ceilings that lend a soft, refined texture. The open-concept living spaces are accentuated by terrazzo floors, 12-foot ceilings, and thoughtful spatial design—including a great room with a sitting area and dining space, a separate media room concealed behind custom 12-foot decorative doors, and a sleek galley-style kitchen outfitted with fully integrated Miele appliances and a secondary glass pivot door for seamless indoor-outdoor flow. Ascending one of two custom staircases, the second floor features warm hardwood floors and a showstopping primary suite that feels suspended above the lake, backyard and pool. This serene retreat offers an all-glass shower, spa-inspired soaking tub, beautifully finished bath cabinetry, and an upholstered wall that subtly conceals a walk-in closet and built-in storage. A second bedroom suite offers an inspired use of space with clever screen walls for privacy and flexibility. Detached from the main home, a third bedroom suite doubles as a guest house, home office, or gym, complete with an en-suite bath, custom built-ins and a wet bar. Outside, the terraced backyard is a tranquil oasis with a saltwater pool and spa, turf lawn for year-round perfection, dual staircases leading to a sundeck and a private, covered boat dock crowned by a glass-enclosed studio mirroring the home’s signature design. Bamboo privacy walls, soaring palms, and a Banyan tree imported from South Florida create a lush and artful landscape. The two-car garage includes epoxy flooring and dual EV charging stations. A singular residence in every sense, this home blends innovative architecture, luxurious finishes and thoughtful design into a rare offering unlike anything else in Winter Park. Built by Z Properties, celebrated in Florida Design and numerous design publications, this is a home for those who appreciate beauty, intention and the art of living well.

3 Beds ⋅ 4 Baths ⋅ Galloway Place Rep SubDv. ⋅ 32789 Zip Code

An architectural triumph, this one-of-a-kind modern masterpiece was custom designed and built in 2023 by the award-winning Z Properties and is ideally sited on the shores of Lake Osceola, part of the Winter Park Chain of Lakes. Radiating bold sophistication and contemporary elegance, the residence is a curated work of art, where floor-to-ceiling glass walls and striking steel windows and doors flood the interiors with natural light and deliver unobstructed panoramic lake views from nearly every room. Enter through a dramatic 12-foot glass pivot door into a 21-foot-long art gallery foyer adorned with a sculptural linear chandelier and Venetian plaster walls and ceilings that lend a soft, refined texture. The open-concept living spaces are accentuated by terrazzo floors, 12-foot ceilings, and thoughtful spatial design—including a great room with a sitting area and dining space, a separate media room concealed behind custom 12-foot decorative doors, and a sleek galley-style kitchen outfitted with fully integrated Miele appliances and a secondary glass pivot door for seamless indoor-outdoor flow. Ascending one of two custom staircases, the second floor features warm hardwood floors and a showstopping primary suite that feels suspended above the lake, backyard and pool. This serene retreat offers an all-glass shower, spa-inspired soaking tub, beautifully finished bath cabinetry, and an upholstered wall that subtly conceals a walk-in closet and built-in storage. A second bedroom suite offers an inspired use of space with clever screen walls for privacy and flexibility. Detached from the main home, a third bedroom suite doubles as a guest house, home office, or gym, complete with an en-suite bath, custom built-ins and a wet bar. Outside, the terraced backyard is a tranquil oasis with a saltwater pool and spa, turf lawn for year-round perfection, dual staircases leading to a sundeck and a private, covered boat dock crowned by a glass-enclosed studio mirroring the home’s signature design. Bamboo privacy walls, soaring palms, and a Banyan tree imported from South Florida create a lush and artful landscape. The two-car garage includes epoxy flooring and dual EV charging stations. A singular residence in every sense, this home blends innovative architecture, luxurious finishes and thoughtful design into a rare offering unlike anything else in Winter Park. Built by Z Properties, celebrated in Florida Design and numerous design publications, this is a home for those who appreciate beauty, intention and the art of living well.

1333 Alberta Drive, Winter Park

$3,350,000

Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes. The existing 4-bedroom, 3-bath home features 3,223 square feet of living space and showcases Country French architectural charm, offering an ideal opportunity to renovate and enhance its timeless appeal—or build new and design a custom estate that takes full advantage of this exceptional lakefront setting. Whether modernizing the current layout or crafting an architectural masterpiece from the ground up, this property offers limitless potential. The home enjoys northern lakefront exposure, providing breathtaking views to the northeast of Winter Park’s protected Genius Preserve and to the west of the iconic Rollins College shoreline, creating a picturesque backdrop with year-round natural beauty and unforgettable sunsets. Significant recent improvements have already been made, including a new roof installed in 2023 with 50-year composite cedar shake shingles, offering the charm of natural materials with enhanced durability. In addition, the dock was redecked in 2023, making this waterfront ready for immediate enjoyment. A rare enclosed boathouse and private dock offer direct access to Lake Virginia and the entire Winter Park Chain of Lakes—ideal for boating, paddleboarding, and lakeside entertaining. Few properties in Winter Park feature this level of water access and historic charm on such a prime stretch of shoreline. Set among multimillion-dollar estates and located just minutes from Park Avenue’s renowned shopping and dining, Rollins College, the Winter Park Golf Course, and a variety of cultural amenities, this property provides the perfect balance of privacy and accessibility. Zoned for top-rated Audubon Park K-8 and Winter Park High School, it offers an ideal location for those seeking the best in lifestyle and education. Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities.

4 Beds ⋅ 3 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Welcome to 641 Virginia Drive, a rare and remarkable lakefront property located in the highly sought-after Timberlane Shores neighborhood of Winter Park. This expansive .48-acre lot offers approximately 100 feet of frontage on Lake Virginia, one of the most desirable lakes on the prestigious Winter Park Chain of Lakes. The existing 4-bedroom, 3-bath home features 3,223 square feet of living space and showcases Country French architectural charm, offering an ideal opportunity to renovate and enhance its timeless appeal—or build new and design a custom estate that takes full advantage of this exceptional lakefront setting. Whether modernizing the current layout or crafting an architectural masterpiece from the ground up, this property offers limitless potential. The home enjoys northern lakefront exposure, providing breathtaking views to the northeast of Winter Park’s protected Genius Preserve and to the west of the iconic Rollins College shoreline, creating a picturesque backdrop with year-round natural beauty and unforgettable sunsets. Significant recent improvements have already been made, including a new roof installed in 2023 with 50-year composite cedar shake shingles, offering the charm of natural materials with enhanced durability. In addition, the dock was redecked in 2023, making this waterfront ready for immediate enjoyment. A rare enclosed boathouse and private dock offer direct access to Lake Virginia and the entire Winter Park Chain of Lakes—ideal for boating, paddleboarding, and lakeside entertaining. Few properties in Winter Park feature this level of water access and historic charm on such a prime stretch of shoreline. Set among multimillion-dollar estates and located just minutes from Park Avenue’s renowned shopping and dining, Rollins College, the Winter Park Golf Course, and a variety of cultural amenities, this property provides the perfect balance of privacy and accessibility. Zoned for top-rated Audubon Park K-8 and Winter Park High School, it offers an ideal location for those seeking the best in lifestyle and education. Whether you're seeking a peaceful lakefront retreat, a renovation opportunity with character, or the perfect site to build your dream home, 641 Virginia Drive offers a once-in-a-generation opportunity in one of Central Florida’s most distinguished communities.

641 Virginia Drive, Winter Park

$2,288,215

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

3 Beds ⋅ 4 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code

A Jewel Box: Curated for a Life Well Lived. Penthouse 404 at The Alabama is a rare architectural gem—a two-story residence that blends historic provenance w/ design-forward luxury in the heart of Winter Park’s most coveted lakefront setting. Created by combining two original top-floor units, this expansive penthouse is the largest in the building & the only one w/ a private outdoor terrace. Originally constructed in 1921 as the Alabama Hotel, the Mediterranean Revival structure has been transformed into an intimate community of 19 private residences overlooking Lake Maitland w/ direct access to the Winter Park Chain of Lakes. Reimagined by Z Properties in 2019 w/ a full renovation, the home reflects thoughtful scale, bespoke craftsmanship & a sophisticated design vision. The dramatic entry foyer features extensive millwork paneling that conceals the bedroom suites & opens into a light-filled great room w/ expansive lake-facing windows & French doors that open to the signature terrace: a professionally landscaped outdoor retreat w/ turf grass, mist fans, lighting, irrigation & custom planters. At the heart of the home, the boldly composed kitchen balances sculptural form & high function. A sculptural block of black quartz anchors the island w/ seating, trimmed in gold metal cladding that echoes the gold countertops & full-height backsplash. Sleek, dark wood, high-gloss cabinetry conceals a panel-ready Thermador suite, including double refrigerator columns & dishwasher. Lacquered finishes, under-cabinet lighting, geometric black-&-white tile, designer fixtures, brass Lutron controls, linear HVAC diffusers, LED recessed lighting & in-ceiling Sonos speakers complete the experience. What appears to be cabinetry is actually a hidden door leading to a den/family room at the rear of the home—overlooking the lake & appointed w/ custom built-ins, black sisal carpet & a moody grasscloth ceiling that mirrors the wall color & adds cinematic ambiance. Throughout, curated materials elevate each room: Venetian plaster, Schumacher wallpaper, signature lighting, oak chevron-patterned hardwood floors & tailored sisal carpets. The main level includes two en-suite bedrooms located just off the foyer. The primary suite offers a lacquered accent wall, boutique-style closets & a spa-quality bath w/ a custom vanity, dual undermount sinks, lucite-&-metal hardware, black quartz counters & full-height mirrors w/ integrated lighting. A glass-enclosed wet room w/ soaking tub & rain shower, Toto toilet & Venetian plaster walls completes the suite. A discreet laundry room & storage area are tucked away nearby. The secondary bedroom features a black vanity w/ gold hardware, black-&-white subway tile, gold sunburst mirror & a walk-in frameless glass shower—ideal for guests or extended stays. Upstairs, a third en-suite bedroom offers treetop & lake views, a mirrored gym wall & private bath featuring a black vanity w/ silver-toned hardware, black quartz top, black penny tile floors & bold geometric tile that spans the shower & vanity wall—complete w/ a tucked-away water closet for added privacy. Additional features include Nest-controlled dual HVAC, 80-gallon stainless water heater w/ booster, Everpure filtration, Jeld-Wen impact-rated windows & doors, Lutron controls & two reserved covered parking spaces. The Alabama offers a lakeside pool, renovated clubhouse, private dock & community boat slips—all just minutes from Park Avenue.

1602 Alabama Drive Unit PH404, Winter Park

$530,000

Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom second-floor condo. This expansive 1,875 SF residence blends modern European design with artistic detail. Designed by a local artist in collaboration with a local architect, every element of this home reflects thoughtful craftsmanship and sophistication. The condo features newer plumbing, electrical wiring, and two new HVAC units that were installed in 2024. Natural light pours in through generous windows, enhancing the open-concept layout that seamlessly connects the dining room, living room, and kitchen. The living room is a welcoming space with built-in shelving, views of the lake, and a walk-in closet that is a useful utility closet. The kitchen is both functional and striking, featuring German textured glass cabinetry, granite countertops, and stainless steel appliances. A show-stopping in-kitchen dining table crafted from high-gloss peacock blue lava stone and French marble serves as a stunning focal point. The primary bedroom offers a walk-in closet, a peaceful sitting area with lake views, and a serene en-suite bathroom complete with a soaking tub. The second bedroom also enjoys lake views and a sitting area, while the third bedroom includes an antique English armoire that serves as a closet. Natural bamboo flooring runs throughout the home, adding warmth and style. The unit is accessed by a private staircase that leads you to your secluded lakefront retreat. The community features include; a very nice swimming pool that was just redone, clubhouse, and recreational areas. This unit includes two dedicated parking spaces and access to a private community boat launch. Annual boat slip rentals are available for $900, and the lake even permits seaplane landings—perfect for those seeking both adventure and tranquility. Located just a short walk from Trader Joe’s, the Winter Park Library, and Hillstone Restaurant, this condo combines quiet lakefront living with unbeatable proximity to shopping, dining, and entertainment. Just minutes from downtown Winter Park, this is a rare opportunity to own a one-of-a-kind home in an exceptional setting.

3 Beds ⋅ 2 Baths ⋅ Lake Killarney Condo SubDv. ⋅ 32789 Zip Code

Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom second-floor condo. This expansive 1,875 SF residence blends modern European design with artistic detail. Designed by a local artist in collaboration with a local architect, every element of this home reflects thoughtful craftsmanship and sophistication. The condo features newer plumbing, electrical wiring, and two new HVAC units that were installed in 2024. Natural light pours in through generous windows, enhancing the open-concept layout that seamlessly connects the dining room, living room, and kitchen. The living room is a welcoming space with built-in shelving, views of the lake, and a walk-in closet that is a useful utility closet. The kitchen is both functional and striking, featuring German textured glass cabinetry, granite countertops, and stainless steel appliances. A show-stopping in-kitchen dining table crafted from high-gloss peacock blue lava stone and French marble serves as a stunning focal point. The primary bedroom offers a walk-in closet, a peaceful sitting area with lake views, and a serene en-suite bathroom complete with a soaking tub. The second bedroom also enjoys lake views and a sitting area, while the third bedroom includes an antique English armoire that serves as a closet. Natural bamboo flooring runs throughout the home, adding warmth and style. The unit is accessed by a private staircase that leads you to your secluded lakefront retreat. The community features include; a very nice swimming pool that was just redone, clubhouse, and recreational areas. This unit includes two dedicated parking spaces and access to a private community boat launch. Annual boat slip rentals are available for $900, and the lake even permits seaplane landings—perfect for those seeking both adventure and tranquility. Located just a short walk from Trader Joe’s, the Winter Park Library, and Hillstone Restaurant, this condo combines quiet lakefront living with unbeatable proximity to shopping, dining, and entertainment. Just minutes from downtown Winter Park, this is a rare opportunity to own a one-of-a-kind home in an exceptional setting.

151 N Orlando Avenue Unit 212, Winter Park

$850,000

Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major updates include a NEW ROOF (2022), A/C (2022), TILE FLOORING THROUGHOUT (2023), a COMPLETE KITCHEN RENOVATION (2023), and a FULLY REMODELED PRIMARY BATH (2023). Enjoy peace of mind with double pane windows, fresh interior and exterior paint (2022), and a septic system service also (2022). The home also features NEWER WINDOW TREATMENTS (2022), a new pool pump (2023), and NEW DOCK DECKING (2024)! Inside you will be pleased to find vaulted ceilings, an abundance of NATURAL LIGHT, and a light, bright OPEN FLOOR PLAN that flows seamlessly between formal and family spaces. From the moment you enter you are greeted with UNINTERRUPTED LAKE VIEWS, setting the tone for a home designed around its beautiful surroundings. The layout includes a spacious FLORIDA ROOM overlooking the pool and lake beyond – perfect for year round enjoyment! Step outside to your private outdoor oasis featuring an open-air pool with waterfall feature, patio, lush landscaping and a fun in the sun SAND BEACH leading to your private dock. Sunset views over the water are a daily luxury! Located in one of Winter Park’s most desired neighborhoods, you are only minutes away from top-tier dining, boutique shopping, parks, and major roadways like US 17/92, Orlando Ave and I-4. With its blend of charm, modern updates, and an unbeatable lakefront setting, this home truly is a rare GEM. Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation!

3 Beds ⋅ 2 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code

Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major updates include a NEW ROOF (2022), A/C (2022), TILE FLOORING THROUGHOUT (2023), a COMPLETE KITCHEN RENOVATION (2023), and a FULLY REMODELED PRIMARY BATH (2023). Enjoy peace of mind with double pane windows, fresh interior and exterior paint (2022), and a septic system service also (2022). The home also features NEWER WINDOW TREATMENTS (2022), a new pool pump (2023), and NEW DOCK DECKING (2024)! Inside you will be pleased to find vaulted ceilings, an abundance of NATURAL LIGHT, and a light, bright OPEN FLOOR PLAN that flows seamlessly between formal and family spaces. From the moment you enter you are greeted with UNINTERRUPTED LAKE VIEWS, setting the tone for a home designed around its beautiful surroundings. The layout includes a spacious FLORIDA ROOM overlooking the pool and lake beyond – perfect for year round enjoyment! Step outside to your private outdoor oasis featuring an open-air pool with waterfall feature, patio, lush landscaping and a fun in the sun SAND BEACH leading to your private dock. Sunset views over the water are a daily luxury! Located in one of Winter Park’s most desired neighborhoods, you are only minutes away from top-tier dining, boutique shopping, parks, and major roadways like US 17/92, Orlando Ave and I-4. With its blend of charm, modern updates, and an unbeatable lakefront setting, this home truly is a rare GEM. Call today to schedule your tour and start living the LAKE LIFE – where every day feels like a vacation!

1018 Turner Road, Winter Park