The agencies at Maitland
These agencies offer a selection of luxury properties vente at Maitland. Feel free to contact them for personalized assistance.
A premier street offering an accessible lifestyle to Maitland's vibrant downtown corridor, known for its community events, restaurants, Lake Lily Park, the beloved independent Enzian Theater and within view of Lake Sybelia. This custom home was completely rebuilt in 2007, adding significant square footage and incorporating a timeless transitional design. Five bedrooms, four baths, stretching across 4,814 square feet with bonus space, there are many ways to make it your own. Inspired by classic Charleston architecture with Florida influences, the exterior features French doors across the front and rear elevations, lantern-style lighting and a metal roof that enhance the home's charm while filling the interiors with natural light. Shutters and upper-level balconies at both sides of home complete the design. Enter inside to a sweeping staircase with elegant iron details, with neutral travertine flooring that flows throughout the main level and finished with volume ceilings. The kitchen, living and dining spaces blend seamlessly together, complemented by an additional sitting room with privacy doors that provide flexible living options. The kitchen features 42-inch custom cabinetry with glass-paneled doors, granite countertops, a farmhouse sink and high-end stainless-steel appliances. Generous laundry and pantry storage are bonus. The dining area showcases rich hardwood flooring, plantation shutters, built-in surround-sound speakers and direct access to outdoor living spaces. The first floor includes two bedrooms with a shared bath, along with an additional hallway guest bath. Upstairs, beautiful wood floors anchor the rooms, and the spacious primary retreat opens to a private balcony spanning across the back of home and with pool views. An expansive walk-in closet provides exceptional organization, while the primary bath features dual vanities, a rain shower with bench seating and a classic clawfoot tub. Additional upstairs laundry stack for convenience. Secondary bedrooms are spacious and full of light, and great closet storage and additional loft are a bonus. Outdoor living centers around a covered porch overlooking the pool, complete with travertine decking and dramatic fountain features. An additional pool house enhances the backyard and offers endless possibilities for guests, entertaining or a private workspace. Outdoor speaker system adds to the ambience. Additional improvements and features include a newer metal roof (2020), two HVACs (2021), water heater (tankless Rinnai installed by Maitland/Winter Park plumbing), plantation shutters throughout, a freshly painted interior, an extensive interior and exterior lighting package, and thoughtfully designed low-maintenance landscaping featuring front-yard turf, mature plantings and clean rock-bed borders. Exterior ceramic paint has a lifetime warranty. Main floor and primary suite have ceiling-installed concert speakers and outdoor speakers. Lower-floor speakers have individual room controls and are served by a pantry stereo system. This exceptional home offers a desirable location with convenient access to major roadways. Zoned for sought-after schools including Lake Sybelia Elementary, Maitland Middle School and Edgewater High School, a designated magnet school, Park Maitland elementary school, and JCC community center and school. A rare opportunity, this home is a standout in one of Maitland's special neighborhoods.
…By Premier Sotheby's International Realty
Completely renovated and move-in ready, a desired first-floor unit in the sought-after Lake Maitland Terrace! This impeccably updated two-bedroom, 1.5-bath condominium blends modern style with an unbeatable lakeside location in the heart of the Maitland/Winter Park area. Thoughtfully redesigned throughout, the home showcases a new kitchen with fresh cabinetry, granite countertops and stainless steel appliances. The baths have been tastefully reimagined with contemporary finishes, and stylish updates continue across the entire unit, delivering a turnkey home you can move into with confidence. The comfortable two-bedroom layout features a full bath in the hall plus a convenient half bath tucked within one of the bedrooms. Sunlight pours through large windows, and the easy first-floor accessibility makes everyday living a breeze. A space-saving washer/dryer combo is conveniently inside the unit, and a dedicated parking space adds day-to-day ease. Set within Lake Maitland Terrace, residents enjoy an amenity-rich community on the shores of Lake Maitland within the famed Winter Park Chain of Lakes. Take in the sparkling community pool with beautiful lake views, gather at the clubhouse with a full kitchen, and enjoy lake access from the private dock and fishing pier, plus kayak racks and tree-lined sidewalks throughout. Ideally just minutes from the charming shops, restaurants, and entertainment of downtown Maitland and Winter Park, you can walk to Lake Lily Park's popular events and the Enzian Theater, and reach Winter Park Village and Park Avenue in no time. Zoned for top-rated schools Dommerich Elementary, Maitland Middle and Winter Park High, this beautifully updated home is ready to impress. Whether you're seeking a primary residence or a seasonal retreat, don't miss your chance to claim this exceptional lakeside gem as your own.
…By Premier Sotheby's International Realty
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was thoughtfully reimagined by renowned designer Ted Maines, resulting in a sophisticated yet timeless aesthetic throughout. Perfectly positioned on a prime oversized corner lot, this remarkable residence blends transitional architecture with modern elegance. Expansive sliding glass doors fill the open-concept living spaces with natural light while creating a seamless connection between the indoors and outdoors. The main living area flows effortlessly from the formal living room and spacious dining area into the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and premium Sub-Zero and Wolf appliances. A refined yet inviting family room with a fireplace provides the perfect setting for everyday living and entertaining. The private first-floor primary suite offers direct access to the lanai and heated saltwater pool and is complemented by a spa-inspired bath with a steam shower and custom his-and-her walk-in closets. A secondary ground-floor bedroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, a spacious loft with a custom dry bar leads to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a whole-house generator supported by a 250-gallon buried propane tank, new pool solar equipment, a newly added semi-circular driveway that enhances both curb appeal and functionality, two newer A/C units, and a new 2026 A/C system featuring re-engineered, high-efficiency ductwork designed to provide optimal climate control throughout the home. The outdoor living space is equally impressive, featuring a heated saltwater pool and spa with a cascading waterfall, elegant stone decking, an outdoor shower, ambient lighting, and a covered summer kitchen-perfect for year-round entertaining. A rare three-car garage completes this exceptional property. All of this is just moments from the shops, dining, parks, and unmistakable charm of downtown Winter Park
…By Annonceur International
Custom-built Santa Barbara-style estate set on one of Winter Park's most coveted brick-paved streets, just moments from Park Avenue's boutiques, galleries and celebrated restaurants, Winter Park Golf Course, Winter Park Racquet Club, historic Rollins College and vibrant Winter Park Village. Built in 2010, this four-bedroom, 4.5-bath residence spans 3,661 square feet across two floors, with cathedral ceilings, a cozy fireplace and colonial windows and French doors, which frame the resort-style pool retreat. A gracious main-floor primary suite offers dual vanities and a large walk-in closet. The double-island chef's kitchen features a gas range and premium Thermador appliances, anchoring an open-plan living, dining and kitchen design, modeled for everyday ease and effortless entertaining. A flexible bonus space is ideal for a home office, formal dining or gym. Upstairs, three additional spacious bedrooms each offer their own en-suite bath and walk-in closet. The home wraps around a covered courtyard leading to the heated saltwater pool and spa, creating a private outdoor enclave. Parking is a breeze with an oversized two-car garage, additional golf cart parking, plus utility pad. Ample storage and workspace complete the rear of the property, which is also wired for a future whole-home generator. A rare offering in the heart of Winter Park, where timeless design meets an unmatched lifestyle.
…By Premier Sotheby's International Realty
Virtually Staged. Beautifully updated and thoughtfully designed, this four-bedroom, three-and-one-half-bath residence blends sophisticated interiors, inviting living spaces and an impressive outdoor setting. Gorgeous curb appeal and meticulously maintained landscaping create a welcoming first impression, while extensive recent improvements bring a fresh, refined feel throughout. Just off the entry, a stately office/den with a wood-burning fireplace offers a handsome, versatile space for a home office, library or sitting room, while a formal dining room provides an elegant setting for entertaining. At the heart of the home is the beautifully updated kitchen, featuring new cabinetry and hardware, marble countertops and an expansive center island with generous seating. Luxury appliances include a striking induction range, integrated refrigerator and convenient beverage refrigeration drawer, while a dedicated coffee bar adds function and style. A sunny breakfast nook provides casual dining space, and the kitchen opens seamlessly to the spacious great room, where French doors lead to the covered lanai and fill the interiors with natural light. A cleverly concealed doorway in the kitchen provides access to the garage and a large bonus room above, complete with a custom wet bar and under-counter beverage refrigerator, an exceptional space for entertaining, recreation or media. Privately on the first floor, the primary suite offers direct access to the covered lanai, an ample custom walk-in closet and spa-inspired bath with dual vanities, soaking tub and glass-enclosed shower. A laundry room with custom cabinetry and powder bath with outdoor access complete the main level. Upstairs, a bright and spacious family room accompanies three additional bedrooms. One features a private en-suite bath, while the remaining two share a Jack-and-Jill bath. All closets feature custom organizational systems. Outdoor living is equally impressive. Accessible from the great room and primary suite, the covered lanai overlooks the newly refinished heated saltwater pool and spa, surrounded by new non-slip pool deck pavers. Wi-Fi-enabled pool and spa equipment provides convenient app-based control. Redesigned by Signature Landscape, the backyard features a turf area for loungers, dedicated firepit space and new fence installed in 2023, creating a wonderful setting for outdoor entertaining. A professionally installed Mist and More mosquito misting system adds another level of comfort, while a gas line from the street supplies the pool and firepit. Extensive upgrades include three HVAC systems installed in 2024 and 2025, a new water heater, whole-home water filtration system and Ecobee smart thermostats. The interior and exterior were repainted in 2025, complemented by new flooring, baseboards and crown molding, custom window treatments, wallpaper and carefully selected designer finishes. Interiors by nationally recognized designer Jaime Garnet of WYC Designs create a polished, cohesive aesthetic throughout. Ideally just minutes from downtown Winter Park, the home offers convenient access to exceptional dining, shopping and cultural amenities, along with major roadways for easy connectivity throughout Central Florida. With extensive updates, flexible living spaces, sophisticated interiors and a beautifully redesigned outdoor setting, this exceptional residence is move-in ready.
…By Premier Sotheby's International Realty
Virtually Staged. 641 Northwood Circle is a rare opportunity to own newer construction in the heart of Winter Park at a newly repositioned price of $1,599,000. Tucked within an intimate residential enclave and surrounded by multimillion-dollar homes, and short distance to Winter Park Golf Course and Park Avenue, this stylish residence offers the location, lifestyle and long-term appeal that make in-town Winter Park desirable. Inside, a sophisticated modern design features polished concrete floors, an open and light-filled floor plan, designer lighting, a chef-inspired kitchen and seamless indoor-outdoor living. A private courtyard and pool create an inviting setting for entertaining and everyday living. This beautiful residence offers an opportunity to buy into an established neighborhood that continues to evolve. At $1,599,000, 641 Northwood Circle presents a compelling opportunity to enjoy the Winter Park lifestyle today while investing in one of the area's enduring locations.
…By Premier Sotheby's International Realty
Location, location, location! Convenient to shopping, restaurants, schools, and easy access to major thorough-a-fares, this lovely home has been exceptionally well maintained and is ready for you to add your personal taste and make it your own. Featuring three bedrooms, two baths, inside utility room (lots of cabinets and even a cedar closet, and washer and dryer included), enclosed patio and one-car garage (with electric garage opener). The views of the backyard are spectacular with fruit trees, magnolia trees and a wood privacy fence. Enjoy your morning coffee or have a spacious place to entertain guests. Home also features a new air-conditioning unit (2026), sprinkler system, large living room and dining room just off kitchen area. Top-rated Seminole County Public Schools within minutes from home. Don't let this one get away.
…By Premier Sotheby's International Realty
Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.
…By Premier Sotheby's International Realty
An opportunity to build new in an established Winter Park neighborhood. The existing home remains on the property and is offered for its land value only, allowing a buyer to design from the ground up on a street where redevelopment is already underway. Within a half mile, seven custom single-family homes are in their final phase of construction, most starting near $1.5 million. Border Drive itself is a mix of longtime homes and newer builds, shaded by mature trees and free of through traffic. Once the site is prepared, the parcel supports a custom plan with room to work in a pool, covered lanai and summer kitchen. Bring your own builder, or ask for an introduction to builders already working in the area. Park Avenue shops and restaurants, Rollins College, the Farmers Market and the chain of lakes are all a short drive away. Property sold as is. The buyer is to verify setbacks, utilities, impact fees, demolition requirements and permitted building dimensions with the City of Winter Park.
…By Premier Sotheby's International Realty
Park Hill is one of Winter Park's most coveted addresses, a distinguished collection of luxury brownstones situated at the northern end of Park Avenue, moments from the city's finest boutiques, restaurants, cultural landmarks and the historic Winter Park Golf Course. Within this exclusive enclave, residence 649 occupies one of the community's most private settings. Beyond the stately brick courtyard and gas lantern-adorned entrance, this three-story home with a private elevator is thoughtfully scaled for refined living. Not oversized, but extraordinarily well-appointed. Ten-foot ceilings, intricate millwork and moldings and generous windows establish an ambiance of quiet elegance, while hardwood floors and designer fixtures carry that standard throughout. The open-concept main living area is built for effortless entertaining. The chef's kitchen features Wolf and Sub-Zero appliances, custom wood cabinetry, marble accents, a center island with bar seating and a wet bar with a beverage refrigerator and ice maker. The space opens directly to a private courtyard with a summer kitchen and dedicated alfresco dining area, creating a genuinely tranquil retreat that feels removed from the energy of the avenue. Upstairs, two guest suites each offer walk-in closets and en-suite baths. A dedicated laundry room and a covered terrace with a fireplace, wet bar and half bath complete the level. The third-floor primary suite provides a true sense of retreat, with two custom walk-in closets, a private balcony and a spa bath filled with natural light from windows and skylights. Dual vanities, a glass-enclosed steam shower and a soaking tub are finished throughout in premium materials. Constructed of Old Carolina brick with three-story block construction, precast exterior trim and a slate mansard roof, the residence features a two-car air-conditioned garage, ample storage and soundproof hollow core floors. With exterior maintenance managed by the association, the lifestyle here is genuinely lock-and-leave. This is a rare opportunity to own in one of Central Florida's most prestigious communities, in a location that simply cannot be replicated.
…By Premier Sotheby's International Realty
Available furnished or unfurnished, lease-to-own or straight lease (6-12 months). On a picturesque brick street in Winter Park, this beautifully designed modern traditional pool home blends timeless architecture with thoughtful, high-end finishes throughout. Built in 2015 and offering over 3,100 square feet, the home features four bedrooms, three full baths, and a flexible three-story layout designed for everyday living and effortless entertaining. A welcoming front porch leads into a bright foyer highlighted by custom millwork and warm wood flooring, setting the tone for the home's clean, curated style. The open-concept main living space flows seamlessly from the dining area into a spacious family room and a chef's kitchen designed to impress. Anchored by a generous marble island with seating, the kitchen features Viking stainless steel appliances, a gas cooktop, honed granite perimeter countertops, custom cabinetry with upper and under-cabinet lighting, and stylish tile backsplash. A wet bar with wine refrigerator adds to the home's entertaining appeal. The first floor also includes a versatile office or playroom with custom built-ins, a functional mudroom/drop zone and abundant storage throughout. Upstairs, the primary suite offers a peaceful retreat with natural light and a spa-inspired bath featuring dual vanities, a soaking tub and a glass-enclosed shower. Secondary bedrooms are well-sized and thoughtfully designed, while the third-floor bonus suite with full bath provides ideal space for guests, a home office or additional living. Outdoor living is equally inviting, with a covered back porch equipped with remote-controlled phantom screens overlooking a private, professionally landscaped yard with artificial turf and a low-maintenance pool, ideal for year-round enjoyment. Additional features include two HVAC systems with Nest thermostats, hardwood flooring on the main level, and designer finishes throughout. Zoned for sought-after schools including Dommerich Elementary, Maitland Middle and Winter Park High. This is a rare opportunity to own a move-in ready home that balances style, function and location in one of Winter Park's desirable settings.
…By Premier Sotheby's International Realty
WOW! AN AMAZING NEW PRICE! SEE IT THIS WEEKEND! Perfectly situated along a picturesque brick lined street with sidewalks in the heart of Winter Park, this beautifully refined residence offers timeless elegance, exceptional craftsmanship and a warm, inviting atmosphere just moments from the area's renowned parks, boutiques and dining. Bathed in natural light, the thoughtfully designed two story floor plan features four bedrooms, four full baths and rich maple wood flooring throughout the main living areas. At the heart of the home, the stunning chef's kitchen is designed for both everyday living and effortless entertaining, showcasing an expansive center island with a beverage refrigerator, granite countertops, a beautiful backsplash, abundant custom wood cabinetry, a pantry and a five burner gas range with double ovens. The kitchen flows seamlessly into the spacious family room, where a gas fireplace creates a welcoming focal point and French doors open to the covered patio and private backyard, extending the living space outdoors. The elegant dining room, accented with custom wainscoting, provides a sophisticated yet comfortable setting for intimate dinners and larger family gatherings alike. Just beyond, the thoughtfully designed laundry room with a butcher block countertop, custom shelving and storage. A versatile first floor room, currently serving as a playroom, is adjacent to a beautifully appointed marble floored full bath and is equally suited as a guest suite, executive office, fitness room or flex space. Upstairs, a cozy loft landing provides an additional sitting area or workspace, while the luxurious primary suite serves as a peaceful retreat featuring a beautifully new spa inspired bath with dual vanities, granite countertops, a soaking tub, an oversized walk in shower and an impressive custom walk in closet. Two additional bedrooms are connected by a beautifully renovated Jack and Jill bath, each with its own private vanity area for added comfort and functionality. Thoughtful details including higher ceilings, generous storage, plantation shutters, crown molding and baseboards enhance the home's refined character throughout. Adding exceptional versatility, the detached guest house features a full bath and a spacious walk in closet, creating the ideal space for guests, a private home office, studio or multigenerational living. The front paver area along with a long, deep driveway provides abundant parking while complementing the home's exceptional curb appeal. Ideally zoned for highly regarded Dommerich Elementary, Maitland Middle and Winter Park High School, this exceptional property also offers a 2021 roof, three HVAC systems (one approximately three years old and two approximately six years old), a Rinnai gas tankless water heater, newly added insulation and a storage shed not within site yet easily accessed just behind the guest house and the added benefit of no HOA. This is more than a home, it is a place to gather, entertain, relax and create lasting memories in one of Winter Park's most sought after neighborhoods and a most desirable lifestyle. A conceptual pool rendering illustrates the potential for a pool, including approximate placement and size. Welcome Home!
…By Premier Sotheby's International Realty
LUXURIOUS LIVING WITH FANTASTIC LOCATION This Winter Park three story townhouse is within walking distance to all the fun amenities of the city- the many restaurants, boutique shops, banks, post office, farmers market, Central Park and Rollins College. Designed by architect Phil Kean and built in 2017 the owners have embellished this townhome with custom millwork and finishes, wood floors, sound system, full house generator and a private elevator to all floors. The first floor has a two car garage with storage lift above, large laundry room/home office and a downstairs guest suite. The second floor features a stylish and comfortable living room with lovely custom ceiling detail and moldings, gas fireplace, a sophisticated powder bath, and a beautiful dining room that opens to an eat-in chef's kitchen with Subzero, Wolfe and Bosch appliances and light Taj Mahal quartzite countertops. The third floor offers the spacious master bedroom and bath and also has the additional guest bedroom suite. Take the elevator to the roof top for great views of the city and here find even more potential space for fun entertaining. If your dream is to own a townhome in the heart of Winter Park, here is a stunning one for you!
…By Annonceur International
Nestled along one of Winter Park's picturesque brick streets, this beautifully appointed four-bedroom, three-and-one-half-bath residence combines timeless charm with modern luxury in an exceptional location. Thoughtfully designed with an open-concept floor plan, the home offers seamless everyday living and effortless entertaining. At the heart of the home is the beautifully updated chef's kitchen overlooking the spacious living room. Premium Thermador appliances include an impressive eight-burner range featuring six gas burners and two induction burners, a separate steam oven, a built-in microwave and a three-tower refrigeration system with refrigerator, freezer and wine refrigeration. A generous breakfast nook provides abundant seating for casual dining, while the adjacent formal dining room offers versatility and is currently utilized as a private home office. The inviting living room is filled with natural light and features French doors that open to the covered lanai, creating an ideal indoor-outdoor living experience. The first-floor primary suite serves as a peaceful retreat with a spacious walk-in closet, two sets of blackout window treatments, a luxurious spa-inspired bath featuring a glass-enclosed shower and separate soaking tub and private access to the lanai and pool area. Completing the first floor are a convenient built-in workspace, a separate laundry room and a stylish powder bath. A graceful staircase leads to the second level, where you'll find three additional bedrooms, including one with an ensuite bath, along with a generous family room that provides the perfect gathering space for family and guests. Expansive windows throughout the home fill every room with abundant natural light, creating a bright and welcoming atmosphere. Outside, the covered lanai features remote-controlled retractable screens, including an integrated pet door, allowing the space to be fully enclosed for year-round enjoyment. The sparkling saltwater pool with a tranquil waterfall feature is surrounded by a beautifully landscaped, fully fenced backyard, offering exceptional privacy and a true backyard oasis. Additional features include LeafGuard-protected rain gutters, new exterior paint completed in July 2026 and a spacious two-car garage. Ideally located, this exceptional home is just an easy bike ride to the renowned boutiques, restaurants, coffee shops and Central Park along Park Avenue, as well as the popular weekly Winter Park Farmers' Market. Offering luxurious finishes, thoughtful design and an unbeatable location, this is a wonderful opportunity to enjoy the very best of Winter Park living.
…By Premier Sotheby's International Realty
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 240 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable corner homesite with private lake access and the ability to build your own dock.
…By Premier Sotheby's International Realty
Own a piece of Lake Killarney, a rare opportunity to build your dream water-view estate in the heart of Winter Park. This exceptional homesite offers direct access to private, spring-fed, skiable Lake Killarney, complete with water rights and the ability to build your own private dock. An increasingly rare opportunity in one of Central Florida's most desirable communities. Ideally located just minutes from Park Avenue, Winter Park Village, Rollins College and downtown Orlando, you'll enjoy the perfect balance of lake life, tranquility and accessible convenience. Experience award-winning dining, boutique shopping, entertainment, cultural attractions and everyday conveniences just moments from your future home. Priced to encourage redevelopment, this property is adjacent to 230 Killarney Drive, creating a rare opportunity to purchase one or both parcels. Together, they form an extraordinary double-lot assemblage with expansive views of Lake Killarney and endless possibilities to design a landmark residence. Whether purchased individually or together, opportunities to own on Lake Killarney are exceptionally limited. Build the custom home you've envisioned while enjoying one of Winter Park's most coveted locations from this desirable homesite with private lake access and the ability to build your own dock.
…By Premier Sotheby's International Realty
Discover an exceptional opportunity to own a penthouse residence at The Landmark, one of downtown Winter Park's exclusive addresses. Directly along the desired brick streets of Park Avenue, this boutique condominium community consists of only 13 residences and offers an unparalleled blend of privacy, sophistication and accessible convenience. Just outside your door, enjoy acclaimed dining, boutique shopping, art galleries, sidewalk cafés, Central Park and the year-round events that have made Winter Park one of Central Florida's sought-after destinations. Behind The Landmark's secure wrought-iron gates, residents are welcomed into a beautifully landscaped courtyard centered around a timeless fountain and illuminated by dozens of gas lanterns, creating a warm and elegant atmosphere reminiscent of a European enclave. Impeccably maintained and thoughtfully designed, the community provides a peaceful retreat while remaining moments from the vibrant energy of Park Avenue. Residence J occupies a premier penthouse position and is filled with natural light, enhanced by soaring ceilings, expansive windows, and multiple French doors that open to private terraces overlooking Morse Boulevard and the surrounding downtown streetscape. The spacious floor plan is designed for comfortable daily living and effortless entertaining. The living and dining areas are anchored by a gas fireplace and flow seamlessly into the kitchen, where integrated appliances, a gas cooktop, generous workspace, and a charming breakfast area create a functional and inviting gathering space. The primary suite serves as a private sanctuary, featuring dual vanities, separate water closets, an oversized walk-in shower and a custom-designed walk-in closet. Two additional guest bedrooms provide flexibility for family and visitors. One bedroom is connected to a Jack-and-Jill bath, while the third enjoys a private en-suite bath and a Juliet balcony that captures the charm and character of downtown Winter Park from above. Additional amenities include two deeded underground parking spaces, a private climate-controlled storage room, and access to the community's shared outdoor entertaining area, complete with a summer kitchen and courtyard gathering space. Whether enjoyed as a full-time residence or a lock-and-leave retreat, this penthouse offers a rare combination of luxury, security and an unmatched Park Avenue lifestyle in the heart of Winter Park.
…By Premier Sotheby's International Realty
Located in the downtown corridor within 2 blocks of Park Avenue, this exceptional one-story residence completed in 2022 offers the ideal blend of contemporary design, refined finishes and a walking lifestyle to downtown WP shops, events & restaurants! Thoughtfully designed with three bedrooms, two and one-half baths, and an open-concept floor plan, the home showcases clean architectural lines, soaring ceilings and walls of glass that fill the interior with natural light while framing views of the beautifully landscaped grounds. The chef's kitchen serves as the centerpiece of the home, featuring premium Wolf and Sub-Zero appliances, custom cabinetry, a center island with seating, and workspace for everyday living and entertaining. The adjoining dining area flows seamlessly into the spacious great room, where custom-built library shelving creates a striking focal point and adds warmth and character to the modern design. Beautiful polished concrete floors extend throughout the residence, providing a cohesive and sophisticated aesthetic. Designed with privacy in mind, the split-bedroom floor plan places the primary suite in its own secluded wing. This spacious retreat offers direct access to the covered rear patio and features a beautiful bath with dual vanities, an oversized walk-in shower, private water closet, and an impressive custom walk-in closet measuring approximately 11 by 9 feet. Conveniently accessible from the primary bath and laundry room, the thoughtfully designed closet enhances everyday functionality. On opposite side of the home, two additional guest bedrooms are connected by a well-appointed Jack-and-Jill bath, while a stylish powder bath is ideally located for visitors. Outdoor living is equally inviting with a covered patio with a privacy bamboo hedge that creates a peaceful backdrop for relaxing or entertaining. An attached two-car garage completes this beautifully appointed residence. Ideally near the acclaimed restaurants, wine bars, coffee shops, and boutiques of Hannibal Square, this home offers one of Winter Park's desirable lifestyles. Visit the renowned shopping, dining, galleries and sidewalk cafés of Park Avenue, enjoy nearby Central Park and community events, or take advantage of the proximity to Rollins College, the Winter Park Farmers' Market and major roadways providing convenient access throughout Central Florida. This is a rare opportunity to enjoy nearly new construction in one of Winter Park's sought-after neighborhoods, where modern luxury and exceptional accessibility come together.
…By Premier Sotheby's International Realty
Within ROAM, you'll find Wilds 360, a collection of single family residences designed specifically for mountain living. The Torrey's Peak floor plan is built for an active Colorado lifestyle with high quality, durable interior and exterior finishes. Inside the homes you'll find three bedrooms plus a second living/rec/bunk room thoughtfully laid out over three levels of luxurious living and fresh, mountain modern design. Multiple outdoor living spaces include an open air rooftop deck with snow-melt system, community dark skies design for stargazing, options to add a rooftop bar, outdoor kitchen and hot tub. Boasting an open gourmet kitchen with premium stainless appliances, these homes are comfortably finished with ERV air exchange systems & in-floor radiant heat, designed for comfort! Adjacent to the kitchen and breakfast bar you flow seamlessly into the large dining area and living room with fireplace designed for groups of any size. Premium standard finishes include solid wood doors and trim, wood cased JeldWen windows, hand troweled walls, luxury vinyl plank flooring, in-floor radiant heat, open floating staircase, insulated, and heated garage. Enjoy the surroundings from your private rooftop hot tub while taking in spectacular views of the Continental Divide, the Winter Park ski area and all of the wildlife that ROAM through the meadow on a daily basis. With the next phase anticipated by the end of this year, now's your chance to secure a brand new, mountain modern home nestled between Winter Park's Main Street and the Fraser River! ***Listing photos are virtually staged and from a previous phase. They are only a general representation of the floor plan. Specific colors, finishes & appliances for this home may differ. Sq. footage provided by architect's renderings in the Documents section.
…By Liv Sotheby's International Realty
Spacious 4BR townhome conveniently located in Downtown Winter Park within walking distance to all the action! This Red Quill Townhome offers lots of space on multiple levels including 2 dining areas, 2 gas log fireplaces, formal living room and lower level rec room for accommodating large groups. This oversized end unit is located at the back of the complex with walls of windows and tons of natural light on every level. It also features a private hot tub, heated 1-car garage, front and back decks as well as a new boiler system for the radiant heat syatem. The complex is set back off of Main Street away from the hustle and bustle, you'll find the green spaces of Confluence Park just behind the townhomes as well as easy access to the Fraser River Trail. This one is teed up for Summer fun!
…By Liv Sotheby's International Realty
Ideally located in Winter Park, this newer end-unit townhome offers an exceptional opportunity to enjoy the Colorado mountain lifestyle with nature, town, and world-class skiing all close at hand. Just steps from the Arapahoe National Forest, miles of hiking and biking trails are right outside your door, while Winter Park's restaurants, shops, and activities are within easy walking distance. A short drive or complimentary shuttle ride takes you to Winter Park Resort for world-class skiing and snowboarding. Inside, the home is bright, inviting, and designed to take full advantage of its beautiful mountain setting. The open-concept main level features a spacious great room with large windows, a contemporary fireplace, and seamless connection to the kitchen and dining areas. Warm wood cabinetry, quartz countertops, stainless-steel appliances, and a generous center island create a welcoming kitchen that is equally suited to casual mornings and entertaining. The dining area looks out to the surrounding trees, while the expansive windows throughout the main level bring the scenery into the home. The private deck is a natural extension of the living space and a wonderful place to gather or unwind. A hot tub, outdoor seating, and fire feature create an inviting outdoor retreat, perfect for relaxing after a day on the trails or slopes while taking in sweeping Continental Divide views. All three bedrooms are located on the upper level, creating a comfortable sense of privacy while taking advantage of the home's elevated views. The primary suite features an ensuite bath with dual vanities and a spacious walk-in shower. A generous guest bedroom also captures the scenery, while the bunkroom offers a fun and flexible space for family and guests. A full bath serves the guest bedroom and bunkroom. The upper landing features a dedicated desk and window overlooking the surrounding landscape, creating a quiet, light-filled space for working remotely. A three-car attached garage is an uncommon and highly desirable feature for a townhome, offering plenty of room for vehicles and all the gear that comes with mountain living. An EV charger adds further convenience. With its newer construction, end-unit setting, beautiful mountain views, private outdoor living, generous garage, and enviable proximity to both the national forest and Winter Park's vibrant town center, this is a wonderful place to enjoy everything the mountains have to offer, in every season.
…By Liv Sotheby's International Realty
Welcome to your dream mountain retreat in the coveted Leland Creek neighborhood of Winter Park. This immaculate 6-bedroom, 4.5-bath home is designed for entertaining and embracing the mountain lifestyle. Step inside to soaring tongue-and-groove vaulted ceilings, pristine hardwood floors, and sweeping Continental Divide views. The chef's kitchen--featuring a large island, Wolf gas cooktop, and spacious butler's pantry--flows seamlessly into the great room, where French doors open to an expansive covered patio with a built-in wood-burning fireplace--perfect for year-round gatherings. After a day on the slopes, relax in the hot tub with mountain views or unwind in the luxurious primary suite. Main-level living includes a guest suite with ensuite bath and a third bedroom or home office, alongside the primary. The walkout lower level offers a generous TV/game room with wet bar and beverage fridge, plus three additional bedrooms (two sharing a Jack-and-Jill bath). A cozy loft adds flexible space for guests or game night. An oversized 3-car garage and large unfinished storage area provide plenty of room for all your gear. Radiant heat throughout (including the garage), a recently replaced boiler, new roof (2023), fresh exterior stain, and new driveway (2023), this home is as functional as it is beautiful. Set on a .62 acre lot with trail access nearby and downtown Winter Park just a short walk away. Sold fully furnished--just bring your belongings and start living the mountain lifestyle.
…By Liv Sotheby's International Realty
Wake up on top of the world with panoramic mountain views and feel the peacefulness wash over as you unwind with pure nature. Ski, hike, bike, fish, boat, dine, and RELAX. Only an hour from Denver, by car or train Winter Park is one of the fastest growing mountain towns in Colorado. Offering over 3000 acres of terrain as part of the legendary Ikon Pass, skiing is just one of the endless activities in this winter wonderland. During summer the town boasts world class mountain biking, expansive hiking trails, stunning golf courses, nearby lakes, and weekly music and cultural festivals. Situated on a quiet cul-de-sac, this fully renovated home was mindfully curated with love by Roxy Blu Homes & By Brooke Design. Perfectly located, you'll enjoy being fully immersed in nature, while being minutes to downtown. Surrounded by breathtaking mountains, swaying trees and chirping birds. Enter into the open floor plan with dreamy kitchen, butler pantry, and 20' vaulted ceilings. The perfect blend of indoor/outdoor living, the main room's glass wall opens to the front deck with 180 degree unobstructed mountain views. Soak up the sun all year long whether barbecuing with friends in summer or melting into the hot tub with winter. The primary suite oasis offers a stunning bathroom and spacious walk in closet. Above enjoy a custom built bunk room and balcony nook with all the mountain views. The lower level offers a perfect hang out space with kitchenette, game area, and media room. 2 beds and 2 baths on lower level give endless options including making the entire level a private apartment. Massive 3 car garage and driveway perfect for cars, gear, and toys. Plenty of room for snowmobiles, boat, and camper. Mudroom with built in storage lockers. 2 laundry rooms.2 gas fireplaces. Deck engineered and wired for hot tub. Designed for lower level to be separate apartment if desired. Steps to free ski bus. New hvac, electrical, plumbing, sewer. Potential for $15K+ per month in rental income
…By Annonceur International
Rare 4-bedroom condo in the heart of downtown Winter Park with slope views, outdoor living, and strong income potential. Located in Apres Winter Park, this residence offers the convenience buyers want most: walkability to restaurants, shops, coffee, entertainment, and access to Winter Park Resort from the Lift bus line just outside. Enjoy a private rooftop deck for taking in the mountain setting, plus a wraparound deck off the primary suite with views toward the ski slopes. During ski season, the property has rented for up to $7,000/month, making it a compelling mountain getaway, second home, or investment opportunity. The building also offers amenities including a welcoming lobby, fitness center, and ski lockers for effortless mountain living in one of Colorado's most exciting ski towns.
…By Liv Sotheby's International Realty
Within ROAM, you'll find Wilds 360, a collection of single-family residences designed specifically for mountain living. The Gray's Peak floor plan is built for an active Colorado lifestyle with high quality, durable interior and exterior finishes. Inside the homes you'll find three bedrooms plus a second living/rec/bunk room thoughtfully laid out over three levels of luxurious living and fresh, mountain modern design. Multiple outdoor living spaces include an open air rooftop deck with snow-melt system, community dark skies design for stargazing, options to add a rooftop bar, outdoor kitchen and hot tub. Boasting an open gourmet kitchen with premium stainless appliances, these homes are comfortably finished with ERV air exchange systems & in-floor radiant heat, designed for comfort! Adjacent to the kitchen and breakfast bar you flow seamlessly into the large dining area and living room with fireplace designed for groups of any size. Premium standard finishes include solid wood doors and trim, wood cased JeldWen windows, hand troweled walls, luxury vinyl plank flooring, in-floor radiant heat, open floating staircase, insulated, and heated garage. Enjoy the surroundings from your private rooftop hot tub while taking in spectacular views of the Continental Divide, the Winter Park ski area and all of the wildlife that ROAM through the meadow on a daily basis. With the next phase anticipated by the end of this year, now's your chance to secure a brand new, mountain modern home nestled between Winter Park's Main Street and the Fraser River! ***Listing photos are virtually staged and from a previous phase and are only a general representation of the floor plan. Specific colors, finishes & appliances for this home may differ. Sq. footage provided by architect's renderings in the Documents section.
…By Liv Sotheby's International Realty
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