Refine Search
Map
Sort by
$1,339,000
3 Beds ⋅ 4 Baths ⋅ Mondrian/Winter Park Twnhms SubDv. ⋅ 32789 Zip Code
Under contract-accepting backup offers. Luxury waterfront living in Winter Park. Perfectly positioned on a premium corner homesite overlooking beautiful Lake Killarney, this exceptional contemporary townhome offers 3 bedrooms, 3.5 bathrooms, and nearly 2,400 square feet of thoughtfully designed living space with spectacular water views, abundant natural light, and the low-maintenance lifestyle today’s buyers desire.A dramatic 17-foot foyer welcomes you into an expansive open-concept living area where soaring 11-foot ceilings and walls of floor-to-ceiling glass showcase breathtaking lake vistas and create an effortless connection between the indoor and outdoor living spaces. The spacious great room flows seamlessly into the dining area and kitchen, creating an ideal setting for both everyday living and entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, double-stacked soft-close cabinetry, stone countertops, a large center island with seating, a generous walk-in pantry, new designer RH lighting throughout, and motorized window shades. Just beyond, the covered rear lanai provides the perfect place to enjoy morning coffee, evening cocktails, or simply relax while overlooking the peaceful shoreline. Upstairs, the luxurious primary suite serves as a private retreat featuring expansive waterfront windows, dual walk-in closets, and a spa-inspired bath with an oversized frameless glass shower, a long single vanity with dual sinks, ample storage, and a private water closet. A spacious loft provides the perfect flex space for a home office, media room, or reading lounge. Step outside to the second-floor balcony complete with an outdoor kitchen, where elevated views of Lake Killarney create an unforgettable backdrop for entertaining. Two additional bedrooms, including one with an en-suite bath, provide comfort and privacy for family and guests, while the upstairs laundry room is thoughtfully positioned between the primary and secondary bedrooms. Additional features include engineered hardwood flooring, porcelain tile, high-end contemporary finishes throughout, abundant storage, a two-car attached garage with an epoxy floor, EV charging station, garage door opener, and a tankless gas water heater. Residents of Mondrian at Winter Park enjoy beautifully maintained grounds, private roads, reclaimed irrigation, a community dock, and lake access to one of Central Florida’s most desirable ski lakes. The HOA also includes cable television, high-speed internet, exterior grounds maintenance, and pest control, making for truly effortless ownership. Combining exceptional waterfront views, sophisticated contemporary design, premium finishes, an ideal floor plan, and one of Winter Park’s most convenient locations, this is a rare opportunity to own one of the community’s most desirable lakefront residences. Just minutes from Park Avenue, Winter Park Village, AdventHealth, Rollins College, Interstate 4, and Downtown Orlando, this home offers the perfect balance of luxury, convenience, and low-maintenance living. Schedule your private showing today and discover everything this exceptional Lake Killarney residence has to offer.

1778 Mondrian Circle, Winter Park
$3,500,000
3 Beds ⋅ 5 Baths ⋅ Park Hill SubDv. ⋅ 32789 Zip Code
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.

649 N Park Avenue, Winter Park
$3,278,530
4 Beds ⋅ 5 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code
Located in the desirable heart of the Via's, this single story home with a transitional interior in Sicilian Shores is a meticulously renovated Winter Park charmer. Nestled quietly on an almost 1/2 acre corner lot, this beautiful home is walking distance to the Winter Park Racquet Club and easy proximity to Park Avenue and Interlachen Country Club. Complete with a gracious master bedroom adjacent to an eloquent sitting room and walk in closet, a secondary master sized bedroom, two beautiful guest bedrooms, en suite bathrooms for all bedrooms, and half bath, this floor plan is the perfect design for any living configuration. With the exception of one guest bathroom, the entire home has been redone with wood look tile from Italy throughout and a plethora of custom upgrades and style features. An elegantly appointed kitchen, laundry, tiled and screened porch (with added gas fireplace and television), stunning master bath, built-ins, and large gas burning fireplace in living room are among the many special features of this stunning single story residence. With plenty of natural light and well-maintained landscaping, 700 Pinetree is perfectly appointed for Winter Park living at its finest. Exterior includes fenced dog run with turf, gated back yard, pool, lighting, sprinkler system, pavers, and mature privacy landscaping. Appliances include GE Cafe and Sub Zero. Natural gas, LED lighting throughout, and custom electronics in fourth bedroom turned media space. California closet in a true master suite with freestanding tub and plenty of storage, high volume and tray ceilings, skylights, integrated home generator, and a six year old roof add to the appeal of this stunning corner property. Elegance, privacy, and sophistication, combined with quality finishes and touches makes this home a true gem!

700 Pinetree Road, Winter Park
$425,000
2 Beds ⋅ 2 Baths ⋅ Lake Virginia Condo SubDv. ⋅ 32789 Zip Code
Welcome to this newly updated 2-bedroom, 2-bath condo ideally situated just steps down from shops, dining, and cultural attractions of Park Ave and Rollins College. Freshly painted and featuring brand-new flooring throughout, this home offers a perfect blend of comfort, convenience, and modern style. The spacious open layout includes a bright living area that opens to a lovely screened-in lanai—perfect for enjoying your morning coffee or relaxing after a day on the lake. The primary suite boasts a generous walk-in closet and an en suite bath, providing a private and relaxing retreat. Located in the highly sought after Lake Virginia Condominiums, residents enjoy resort style amenities, including a lakefront pool and hot tub, boat dock, fitness center, kayak storage, fire pit, bike storage, elevator access, and reserved covered parking. Don’t miss this rare opportunity to own a modernized lakefront unit in one of Winter Park’s most desirable locations! Residents also have the option to reserve the clubhouse, which features a kitchen, comfortable seating, and direct access to the pool area—making it the perfect venue for gatherings, celebrations, or special events. A poolside guest suite is available to rent for additional visitors. Whether you're looking for a permanent residence, a seasonal getaway, or a smart investment opportunity, this move-in-ready condo offers the very best of Florida living.

690 Osceola Ave Unit 410, Winter Park
$199,000
2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code
Welcome to this beautifully updated second-floor corner unit nestled within the sought-after Aragon Condominium community in the heart of Winter Park. This bright and airy two-bedroom, one-bath home offers a perfect blend of comfort, style, and convenience. Step inside to discover freshly painted interiors and elegant laminate flooring that flows seamlessly throughout the space. The galley-style kitchen offers a functional layout and opens to a spacious living and dining area—ideal for both relaxed evenings at home and entertaining guests. Natural light fills the open-concept living space, while the cozy front patio invites you to enjoy your morning coffee or unwind at the end of the day. Both bedrooms are generously sized with pool view and feature built-in closets for easy organization, while a hallway closet adds extra storage for linens or household essentials. The bathroom features modern finishes and thoughtful design, with a shower and tub. The Aragon community offers a host of amenities designed for easy living, including a tranquil central courtyard, a sparkling community pool, on-site laundry facilities, and ample parking with both assigned and guest spaces. Located in one of Winter Park’s most vibrant neighborhoods, this condo is just steps from shopping centers, grocery stores, restaurants, and retail boutiques. With quick access to I-4 and nearby parks, it offers both a peaceful retreat and a connected urban lifestyle. Whether you’re a first-time buyer, downsizing, or searching for an ideal investment opportunity, this delightful home provides the perfect combination of charm, location, and livability.

851 Miles Avenue Unit 8, Winter Park
$1,335,000
3 Beds ⋅ 3 Baths ⋅ Lyman Ave Villas 1 SubDv. ⋅ 32789 Zip Code
Presenting a stunning and fully furnished END UNIT Townhome, one block off Park Ave! This is 1 of only 8 townhomes built in 2014 by David Weekly, and the only one on the market with incredible Florida outdoor living space. This unit is a gem, with the most privacy and largest side yard of all 8. The location is AMAZING, you can see Park Avenue from your front porch! SO many upgrades, you won't need to do a thing but move in and enjoy walking up to your favorite stores, restaurants, and of course the famous Winter Park Farmer's Market on Saturday mornings! Nothing has been overlooked in this gorgeous residence, so let's take a tour! Entering through the solid wood door, you are greeted with beautiful wood floors and custom window shutters. To your left is a bedroom and/or office with an easy access en-suite full bathroom. Down the hall your eye will be drawn to the breathtaking kitchen with an oversized island, high-end 42" white cabinets with a coffee rubbed stain, GE Monogram appliances, including a natural gas range, and a cozy place for your coffee bar! Looking further you will find the large dining area with a gorgeous crystal chandelier with matching pendants lights over the island. The side bar area pulls your eye into the new custom-built backlit wine room under the stairs! The open concept space invites you into the living room with plenty of room for friends and family to gather. Heading up the stairs you will find a custom-built bookcase before entering into the primary suite. There is so much natural light flowing through the windows from the southern and eastern exposure of this cozy corner bedroom. The primary bathroom has double sinks and a private water closet. Next, we come to the custom-built laundry room, with storage cabinets for days! Coming out of the laundry room we find the 3rd bedroom in the home, a quiet room tucked away for children or guests, and this also has a full bathroom including a comfy tub. Now let's head back downstairs and step out to the OVER 1300 SQ FT OF FENCED-IN FRONT AND BACK OUTDOOR LIVING SPACE! The builder definitely took all of your outdoor needs into consideration when designing this space. The covered brick paver patio with an electric screen boasts a built-in summer kitchen with a gas grill, granite countertops, a wet sink, and storage. There is also a mounted TV on the wall to watch your favorite teams play this fall! Out in the yard is recently installed pet-friendly artificial turf and an area for cornhole or Bocce ball, all inside a fully-fenced yard! The 2-car garage behind the home is accessed by a secured gated entrance. The garage floor has been fitted with custom SwissTrax tiles. Up above the garage is a floored and insulated 200 sq foot storage room that is large enough to stand up and walk around in, and this is climate controlled with a new (2023) mini-split AC (no more need for that expensive storage unit for the Christmas decorations)! Other features include interior paint (2024), new carpet and ceiling fans (2024), new SONOS system, new cabinet hardware, an upgraded whole house security system with cameras, a new (2024) tankless on-demand hot water heater, new (2023) LG washer and dryer, and upgraded landscaping with new uplighting and Mexican stones. The HOA fees cover building insurance, landscaping, watering, pest control with termite bond, roof and gate maintenance. This nearly new townhome right next to Park Avenue is more than just a home, it's a lifestyle!

242 W Lyman Avenue, Winter Park
$765,000
3 Beds ⋅ 3 Baths ⋅ Canton Ave Cottages 1 SubDv. ⋅ 32789 Zip Code
BACK ON MARKET WITH NEW PRICE DUE TO BUYERS CASH PURCHASE DEFAULT!!!Rare find in the heart of Historic West Winter Park - Newer 2017 solid built David Weekley home now available! This modern designed chic home offers energy efficient features with luxury design. Walk into the home and be impressed by the voluminous ceilings and 8' door frames adorned with ceiling crown molding. This unique home design offers ultimate privacy with all bedrooms on the lower floor while the living/entertaining space is upstairs. Windows throughout the home filtrate a natural light that compliment the wooden floors. Upstairs you'll find the living space large and inviting. The chef's kitchen is spacious with abundant cabinetry and offers all stainless-steel Jenn Air appliances. The commercial style gas cooktop offers a wall mounted kettle water feature along with a flat surface griddle and is topped with a deco canopy range hood. The built-in bottom mount refrigerator is complimented alongside the programmable electric oven and convection/microwave. Center kitchen island doubles as dining space with room for four or there's room for a dining table. Solid wood cabinets are topped with glass doors to display stylish dinnerware. Dual pantry sliders with pull out drawers adjoin the wine refrigerator (Jenn Air of course) with additional cabinets. The Great Room's sliding glass doors welcomes you outside to the expansive maintenance free Hardee board deck. The deck is pre-plumbed for both water and gas to complete your grilling needs. The luxurious primary bedroom offers a tray ceiling and large walk-in closet. Venture into the impeccable primary bath and enjoy the huge walk in shower with built-in bench seat and overhead rain and wall mount shower heads. The additional two bedrooms share a bathroom accessible by each side but has a separate door to shower and toilet. The downstairs enormous laundry room is complete with a sink and additional cabinets. You'll find the garage oversized and can be described as 2.5 car size with epoxy coated flooring and an EV charger. Water Softner system stays - easy to use! There's an additional parking pad for your guests. The home is completely fenced and has energy efficient dual tankless gas water heaters and is prewired for 5.1 Surround sound audio. Best part of this small brick paved urban planned community - HOA pays for landscaping maintenance, plant replacement, mulch and sprinkler repair and you're connected to a natural gas utility service. Walk to the best shopping and dining available in Central Florida - Park Ave. and Winter Park Village. The Sunrail and Amtrak train depot is only 6 blocks away with Rollins College right around the corner. Easy commute to Downtown Orlando, Full Sail University and the Orlando International Airport. Best value in 32789 zip code!!! Call today for your showing.

441 N Capen Avenue, Winter Park
$190,000
2 Beds ⋅ 1 Baths ⋅ Aragon Condo SubDv. ⋅ 32789 Zip Code
Welcome to this inviting first-floor unit in the desirable Aragon Condo community, located in the heart of Winter Park. This charming two-bedroom, one-bath condominium features a newly remodeled bath, fresh paint, and all-new luxury vinyl plank flooring throughout, making it ready for its new owner. The galley-style kitchen seamlessly flows into the open living and dining space, perfect for entertaining or relaxing. Both bedrooms offer built-in closets, providing ample storage space. Additionally, there is a hall closet ideal for linens or extra storage. The unit includes a cozy front patio area, perfect for enjoying your morning coffee or evening unwind. Residents of Aragon Condo enjoy a range of amenities, including a central courtyard, sparkling pool, communal laundry facilities, and both assigned and guest parking. This prime location is convenient to multiple shopping centers and is just across the street from a variety of restaurants, quick-serve options, grocery stores, and retail shops. Experience sophisticated living in a community that embodies the art of the home, offering both tranquility and convenience. This condominium is not just a home, it is a haven for those who appreciate the finer things in life.

851 Miles Avenue Unit 3, Winter Park
$1,000,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
Welcome to the epitome of luxury living at The Alabama in beautiful Winter Park. Nestled in one of Central Florida’s most sought-after neighborhoods, this exquisite condo offers a rare opportunity to experience the best of urban convenience and tranquil suburban charm. Residents of the Alabama enjoy access to a range of amenities, including a sparkling pool, fitness center and a clubhouse for social gatherings. An intimate foyer welcomes you into this 2-bedroom, 2-bath unit with 993 square feet of space, gorgeous 7.5” plank White Oak floors and 11’ high ceilings throughout. The well-appointed kitchen featuring Viking & Fisher/Paykel appliances, marble counter tops and ample cabinet space, opens to a great room with lake views. Wake up to the soft Florida sun streaming through large windows of the Primary bedroom retreat which also showcases lake views, custom closet built-ins and a marble bath. Guest suite currently furnished as a flex space opens up to a private 400 sq. ft. terrace with gate (only 5 private patios in entire complex). Extra Details: Roof 2018, boat slip available (first come first serve), climate controlled storage closet, bike/scooter storage, 1 deeded covered parking space, plenty of guest parking, on site manager, property is gated and secured on over 5 acres on Chain of Lakes. No rentals permitted, small pets most welcome. Wether you step outside to your private terrace to unwind and enjoy a cup of coffee in the morning or enjoy the views of the well-manicured grounds/lush landscaping or watch sunset on Lake Maitland…your investment in a beloved piece of Winter Park's history is sure to enhance your lifestyle! Don’s miss the chance to make this luxurious condo your new home.

1602 Alabama Drive Unit 107, Winter Park