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700 Melrose Avenue Unit M23, Winter Park
$340,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Gardens Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Winter Park living, with a view you’ll actually want to come home to! This spacious 2-bedroom, 2-bath condo at Winter Park Gardens is clean and puts you in the middle of it all while giving you a peaceful place to escape. Set on the second floor with elevator access, the home overlooks the community pool and lush mature gardens, giving the living spaces a beautiful green backdrop. Step inside, to your open living area, flooded with natural light. The Florida room adds an extra spot to relax with a good book, work from home, or enjoy your morning coffee, with updated windows bringing in plenty of natural light while helping to keep cooling costs low. Fresh interior paint gives the home a clean, updated feel and an easy canvas for your own style. Just outside your door, Winter Park Gardens offers beautifully landscaped grounds, a community pool, pond, and lighted walking paths. Then there's the location. Walk or bike ride to Park Avenue's restaurants, shopping, and boutiques, the Winter Park Tennis Center, Rollins College, and Mead Botanical Garden. This is a great opportunity to enjoy the lock and go Winter Park lifestyle without giving up space, convenience, or a little peace and quiet. Call to schedule your showing today!

700 Melrose Avenue Unit M23, Winter Park
100 S Interlachen Avenue Unit 401, Winter Park
$825,000
3 Beds ⋅ 2 Baths ⋅ Cloisters Condo SubDv. ⋅ 32789 Zip Code
Opportunity knocks at The Cloisters! This rarely available fourth-floor corner residence offers an exceptional opportunity to create a truly personalized home, with windows on four sides filling the interiors with abundant natural light and capturing desirable eastern exposures, perfect for viewing the sunrise and rocket launches. Also, enjoy tree top and lake views. Held by the same family since 1979, this residence offers more than 1,600 square feet of living space, this 3 bedroom - 2 bath unit is ready for its next chapter. While the interiors await updating, the generous floor plan provides a wonderful blank canvas with endless possibilities to reimagine the space and make it your own. Additional features include in-unit washer and dryer hookups, an assigned parking and storage closet and the unique privacy afforded by its corner location. Nestled along the shores of beautiful Lake Osceola, The Cloisters offers an exceptional lifestyle with an array of desirable amenities, including a sparkling swimming pool, boat slips, a private dock, two fitness rooms, a clubhouse, internet and cable, an on-site manager, and an outdoor grilling area. Ideally situated in the heart of Winter Park, this sought-after community is just a short stroll from The Alfond Inn, SunRail, and the charm of Park Avenue, where you can enjoy an inviting collection of sidewalk cafés, fine dining, boutique shopping, and the picturesque beauty of Central Park. Experience the best of Winter Park living in this exceptional lakefront community. Bring your designer, your vision, and your personal style to transform this special Cloisters residence into something extraordinary. Call today for your private viewing of this wonderful unit.

100 S Interlachen Avenue Unit 401, Winter Park
1602 Alabama Drive Unit 107, Winter Park
$1,150,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
Experience timeless lakefront living at The Alabama, one of Winter Park’s most distinctive and treasured residences. Set on more than five gated acres along the Winter Park Chain of Lakes, this beautifully appointed 2-bedroom, 2-bath condominium offers an exceptional blend of elegance, privacy and effortless living. Inside, soaring 11-foot ceilings and 7.5-inch plank white oak flooring create a light and refined atmosphere. The beautifully designed kitchen features Viking and Fisher & Paykel appliances, marble countertops and generous cabinetry, flowing seamlessly into the great room where expansive windows frame picturesque views of Lake Maitland. The serene primary suite is a private retreat with lake views, custom closet built-ins and an elegant marble bath. The guest suite opens to an extraordinary 400-square-foot private terrace with gated access—one of only five private patios within the community. It is an exceptional setting for morning coffee, intimate entertaining or simply enjoying the lush surroundings. Residents enjoy beautifully manicured grounds, a sparkling pool, fitness center and clubhouse, along with an on-site manager, climate-controlled storage, bike and scooter storage, ample guest parking and one deeded covered parking space. A new roof was completed in 2026, and boat slips are available on a first-come, first-served basis. Small pets are welcome; rentals are not permitted. From morning coffee overlooking the lake to spectacular sunsets over Lake Maitland, this is a rare opportunity to experience the beauty, history and understated elegance of lakefront living in Winter Park.

1602 Alabama Drive Unit 107, Winter Park
250 Carolina Avenue Unit 202, Winter Park
$649,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
Welcome to Park West, an exclusive gated community ideally located just moments from the heart of downtown Winter Park. This impeccably maintained 3-bedroom, 2-bath residence offers a spacious and thoughtfully designed floor plan. The inviting living and dining areas feature an open-concept layout anchored by a traditional decorative fireplace, creating a warm and comfortable setting for both everyday living and entertaining. The generous primary suite offers a private en-suite bath with a walk-in shower and an expansive walk-in closet. The second bedroom is conveniently positioned near the hall bath, which features a tub/shower combination. A dedicated laundry room with built-in shelving and abundant storage adds a level of convenience rarely found in condominium living. Residents of Park West enjoy an array of amenities, including a clubhouse, resort-style swimming pool, and tennis court which also has lines for pickleball, all within a beautifully maintained gated setting. Perhaps the greatest luxury is the location. From Park West, it’s an easy stroll to the boutiques, restaurants, and cultural attractions of Park Avenue, as well as Central Park, world-class museums, the SunRail station, and the Winter Park Golf Course. Offering space, comfort, amenities, and an unbeatable location, this is a wonderful opportunity to own a residence in one of Winter Park’s most desirable communities.

250 Carolina Avenue Unit 202, Winter Park
311 E Morse Boulevard Unit 1-5, Winter Park
$2,475,000
3 Beds ⋅ 3 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park
311 E Morse Boulevard Unit 4-5, Winter Park
$895,000
2 Beds ⋅ 2 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Experience the best of downtown Winter Park living at Whispering Waters, a desirable 55+ lakefront community ideally located on beautiful Lake Osceola and just a short stroll from iconic Park Avenue. Priced BELOW APPRAISED VALUE, this rare third-floor mid-century modern condo combines an unbeatable location, spacious living, and an easy, low-maintenance lifestyle. Step inside to a bright, inviting interior filled with natural light from multiple floor-to-ceiling windows. The spacious living and dining areas overlook tranquil waterfall ponds and beautifully landscaped grounds, creating a peaceful retreat in the heart of Winter Park. A versatile bonus space is perfect for a home office, den, reading room, or creative space. The expansive owner’s suite offers a private sitting area, dual closets, pool access, and a spacious bath with a relaxing jetted tub. The generously sized secondary bedroom features its own cozy reading nook and dual closets—ideal for guests or additional living space. Convenience is built right in with private in-unit washer and dryer hookups, secure underground parking with a deeded space, and elevator access. Even better, the monthly association DUES INCLUDE ELECTRIC, WATER, GAS, SEWER & TRASH, helping make everyday living refreshingly simple. Residents also enjoy an on-site property manager, additional laundry facilities, a community clubhouse, sparkling pool, and beautiful lakefront surroundings. Leave the car at home and enjoy the boutiques, cafés, restaurants, museums, and events of Park Avenue, stroll through Central Park, catch the SunRail or Amtrak, or enjoy nearby Rollins College and Winter Park’s highly rated public golf course. With its PRIME LAKEFRONT SETTING, WALKABLE PARK AVENUE LOCATION, UTILITIES INCLUDED & LOW-MAINTENANCE LIFESTYLE, this condo offers a RARE OPPORTUNITY to enjoy one of Central Florida’s most sought-after communities. COME DISCOVER THE LIFESTYLE THAT MAKES WHISPERING WATERS AND WINTER PARK SO SPECIAL—schedule your private showing today.

311 E Morse Boulevard Unit 4-5, Winter Park
101 S New York Avenue Unit 311, Winter Park
$1,775,000
3 Beds ⋅ 4 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury living in this exquisitely renovated two-story condominium, ideally situated on the third floor of the highly sought-after Douglas Grand in the heart of Winter Park. This elegant three-bedroom, three-and-one-half-bath residence seamlessly blends sophisticated design with everyday comfort. Immediately captivating, the light-filled open floor plan showcases stunning new wide-plank white oak flooring, high ceilings, detailed crown molding, and all-new designer lighting throughout. The chef’s kitchen is a showpiece, featuring crisp white cabinetry, luxurious white quartz countertops, a spacious breakfast bar island, elegant gold hardware, and a built-in desk. A charming breakfast nook offers the perfect setting for morning coffee or casual dining. French doors open to a private enclosed atrium, creating a versatile outdoor retreat ideal for alfresco dining, relaxing, or entertaining guests in style. The expansive living and dining spaces flow effortlessly, while a private first-floor bedroom with en suite bath and walkout balcony provides an ideal space for guests, multigenerational living, or a home office. Upstairs, the primary suite serves as a peaceful sanctuary, complete with an indulgent soaking tub, dual vanities, an oversized walk-in closet, and French doors leading to a large private balcony with sweeping views of Winter Park's iconic Park Avenue—perfect for enjoying sunrise coffee or evening sunsets. A second upstairs en suite bedroom offers its own private bath and generous walk-in closet. Thoughtful features include an upstairs laundry room, a spacious storage closet with potential elevator conversion for future accessibility, and a secure gated garage with two reserved parking spaces. Perfectly positioned in the heart of Winter Park, Douglas Grand places you just steps from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, Winter Park Golf Course, the Winter Park Tennis Center, Winter Park Village, and an array of renowned dining, shopping, and cultural attractions. Enjoy an unparalleled walkable lifestyle in one of Central Florida's most desirable communities. Notable improvements include an interior renovation (2026), front elevation windows and French doors (2024), interior paint (2024), and HVAC system (2022).

101 S New York Avenue Unit 311, Winter Park
311 E Morse Boulevard Unit 7-11, Winter Park
$279,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Charming Downtown Winter Park Pied-à-Terre – Steps from Park Avenue! Welcome to Whispering Waters, a beautifully maintained mid-century community nestled on the shores of Lake Osceola. This light-filled corner studio offers a rare opportunity to own a piece of Winter Park’s most coveted location—just steps from Park Avenue, Central Park, and all the cultural charm the city has to offer. Located on the second floor, this spacious studio boasts an updated kitchenette, generous storage, and abundant natural light. Enjoy secure garage access, mail and package delivery to your door, and a relaxing retreat with sunrise views, osprey sightings, and even rocket launches visible from the community patios. Community Amenities: Sparkling pool, Club room for social gatherings, Peaceful outdoor patios overlooking Lake Osceola and Professional on-site management. Location Highlights include being one block to Park Avenue’s boutiques, cafes, and fine dining. Close to The Alfond Inn, museums, and galleries. Walkable to SunRail & Amtrak station. Moments from the Winter Park Farmers’ Market. This is a rare opportunity to own a stylish, low-maintenance home in the heart of downtown Winter Park where ELECTRIC, GAS, WATER, SEWER and TRASH are included in condo fee. Whether you're looking for a weekend retreat or full-time residence, this pied-à-terre is truly one-of-a-kind. Call today for your private viewing of this condo.

311 E Morse Boulevard Unit 7-11, Winter Park
311 E Morse Boulevard Unit 7-5, Winter Park
$299,000
1 Beds ⋅ 1 Baths ⋅ Phillips Circle Rep SubDv. ⋅ 32789 Zip Code
Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispering Waters, a 55+ iconic Condominium located just steps from Park Avenue and fabulous historic downtown Winter Park!  This architectural mid-century beauty was built in 1960 and has survived every major hurricane since then. Whispering Waters has passed the Milestone and  Structural Integrity Reserve Study with flying colors. Enjoy all of these activities nearby including the award winning restaurants, boutique shops and museums.  There is walkability to the Alfond Inn, Rollins College, the Sunrail / Amtrak Station, Farmer's Market and all things the Park Avenue area has offers including beautiful parks and lakes to explore.  Just outside your door and on the shore of Lake Osceola you will find the historic Winter Park Boat Tour.  At Whispering Waters the lush community grounds and shared patios are a tropical oasis of flowering plants and charming decorative ponds.  This highly sought after ground floor corner unit comes with an abundance of natural light and has just been freshly painted as well as new energy efficient windows installed.  It features neutral colors, easy care ceramic tile in the kitchenette & bathroom, with laminate flooring in the main living area.  The low monthly HOA fee includes electricity, gas, heat, water, sewer, trash, grounds care, pool service and all building exterior maintenance. The owner pays for Cable & Internet. Association approval is required for all new owners.  One assigned & deeded exterior parking space comes with this unit. Drop your groceries off in the covered and gated parking garage in the basement, with a short elevator ride to the ground floor.  Amenities include an onsite manager, pool, clubroom, covered boathouse with boat slips (Docks may become available for lease or purchase). Whether you are seeking a full-time residence, a winter retreat or mother/father in-law suite, this home offers effortless, low-maintenance living-just lock and leave!l Schedule your showing soon as this gem is sure to go quickly! Professional photographs coming soon!

311 E Morse Boulevard Unit 7-5, Winter Park

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