Winter Park Homes with Maintenance Amenities

Winter Park Homes with Maintenance Amenities

Welcome to Winter Park, Florida—a charming enclave that beautifully blends small-town warmth with vibrant cultural experiences. Nestled in Orange County, just a stone’s throw from the bustling heart of Orlando, Winter Park is renowned for its picturesque tree-lined streets, stunning lakes, and a rich tapestry of history. This enchanting city is home to a variety of parks, boutique shops, and exquisite dining options, making it a delightful place to live and explore.

One of the standout features of Winter Park is its array of homes that come with maintenance amenities. Imagine living in a serene environment where your weekends are free from the burdens of yard work and home upkeep. Many properties in this area offer maintenance-free living, allowing you to fully enjoy the lush surroundings and the vibrant community without the hassle of routine chores. Whether you’re looking for a stylish condo or a spacious single-family home, you’ll find options that cater to your lifestyle while providing the convenience of professional maintenance services.

In addition to the ease of upkeep, Winter Park boasts a thriving arts scene, highlighted by the renowned Charles Hosmer Morse Museum of American Art and various seasonal festivals. The city also features a top-rated school system and a strong sense of community, making it an ideal choice for families and retirees alike.

Discover the charm and convenience of Winter Park, where your dream home awaits amidst a backdrop of beauty, culture, and effortless living. Embrace a lifestyle that prioritizes leisure and enjoyment—because in Winter Park, life is meant to be savored.

Newest Winter Park Homes with Maintenance Amenities

700 Melrose Avenue Unit M23, Winter Park
$354,000
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
1500 Gay Road Unit 26-C, Winter Park
$255,000
2 Beds ⋅ 2 Baths ⋅ Chateaux Du Lac SubDv. ⋅ 32789 Zip Code
Enjoy peaceful lake views from this charming second-floor, 2-bedroom, 2-bathroom condo in the desirable Chateaux Du Lac community in Winter Park! This inviting residence offers a functional layout filled with natural light and tranquil water views. Residents enjoy a variety of community amenities, including a swimming pool, clubhouse, sauna, and boat ramp access. Ideally situated in the heart of Winter Park, this community offers a walkable lifestyle with convenient access to shopping, dining, and entertainment, just minutes from the charming boutiques and restaurants of Park Avenue. Whether you're seeking a primary residence or seasonal retreat, this condo offers the perfect combination of location, convenience, and lakeside living. Experience the best of the Winter Park lifestyle!

1500 Gay Road Unit 26-C, Winter Park
100 S Interlachen Avenue Unit 401, Winter Park
$850,000
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
640 N Park Avenue Unit 3, Winter Park
$745,000
2 Beds ⋅ 2 Baths ⋅ Park Aire Condo SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to 640 N Park Avenue, the iconic "pink building" in the heart of downtown Winter Park! This first-floor corner unit captures views of the WP 9 golf course, Casa Feliz and the Park Avenue streetfront from every window. Taken down to the studs and completely reimagined in 2023, this residence is filled with high-end upgrades throughout. Step inside and notice the hand-scraped walnut hardwood flooring as you enter the kitchen, which features custom cabinetry, Danby marble countertops, a European tile backsplash, and top-tier appliances, including a La Cornue range, Fisher & Paykel refrigerator, and GE Monogram dishwasher. Two appliance garages and a hidden butcher block that pulls out when needed make the most of every inch.The living room showcases beautiful views of the WP 9, along with a bar-height eating space with under-cabinet storage and additional built-ins. In the hallway, you'll find a half bath added during the renovation and a full wall of custom cabinetry. The primary bedroom sits in the corner of the building, with large windows framing the views, a spacious walk-in closet, and another full wall of built-ins. Down the hall, a second bedroom with a laundry closet sits beside the full bathroom, finished with a custom vanity and porcelain tile floors. Additional finishes include solid wood doors with Emtek hardware, Visual Comfort lighting throughout, Perrin & Rowe plumbing fixtures, and new windows (2025). Mechanical updates include rewiring, a new electric panel, plumbing updates, and new AC & ductwork (all 2023), plus a new hot water heater (2026). Step out your front door and you're steps from the community pool and everything Park Avenue has to offer. The unit includes one underground parking space and a private storage unit. Truly one of a kind, this like-new condo delivers the best of downtown Winter Park living, with every thoughtful, high-end finish you could want.

640 N Park Avenue Unit 3, Winter Park
188 Sandlewood Unit 1, Winter Park
$290,000
2 Beds ⋅ 3 Baths ⋅ Sandlewood Creek Condo SubDv. ⋅ 32789 Zip Code
Welcome home to 188 Sandelwood Trail, a beautifully updated 2-bedroom, 2-full-bath residence in the heart of Winter Park. Thoughtfully refreshed and move-in ready, this home blends modern comfort with the charm and convenience that make Winter Park one of Central Florida's most sought-after addresses. Stylish wood-look flooring flows throughout the inviting living room, where a wood-burning fireplace creates a warm, welcoming focal point for relaxing evenings or entertaining friends. The updated kitchen shines with granite countertops and stainless steel appliances, combining function and style for everyday cooking. The primary suite is a true retreat, with serene views overlooking the sparkling pool and a private en-suite bath. The second bedroom and full bath adds flexibility for guests, a home office, or hobby space. Enjoy an unbeatable location just minutes from Park Avenue's boutique shopping and dining, lakes, parks, and cultural attractions, with easy access to major roadways for a convenient commute throughout the Orlando metro. Whether you're a first-time buyer, downsizing, or seeking a low-maintenance lifestyle, this Winter Park gem checks every box. Schedule your private showing today!

188 Sandlewood Unit 1, Winter Park
1250 S Denning Drive Unit 119, Winter Park
$265,000
2 Beds ⋅ 2 Baths ⋅ Mead Garden SubDv. ⋅ 32789 Zip Code
Virtually Staged. Welcome to easy, low-maintenance living in the heart of Winter Park! This beautifully updated 2-bedroom, 2-full-bath, first-floor corner residence at Mead Garden Condominiums offers a fresh, move-in-ready interior paired with an exceptional location just minutes from some of Winter Park’s most desirable destinations. Recent updates include new luxury vinyl flooring throughout the kitchen and great room, new carpeting in both bedrooms, fresh interior paint, and a recently redone screened-in porch with a refreshed frame and new screening. The thoughtfully updated kitchen features shaker-style cabinetry, granite countertops with breakfast bar, and stainless steel appliances. Additional features include remodeled bathrooms, low-Emissivity windows and sliding glass door, crown molding, updated baseboards and light fixtures, Nest thermostat, A/C replaced in 2018, and water heater replaced in 2019. Enjoy Florida living from the screened-in porch with convenient direct access to the community pool, onsite laundry facility, and mailroom. The first-floor corner location offers added privacy, comfortable single-level living, and a designated parking space.

1250 S Denning Drive Unit 119, 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
311 E Morse Boulevard Unit 4-5, Winter Park
$925,000
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
2500 Lee Road Unit 104, Winter Park
$242,400
2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
Back on market due to buyer circumstances unrelated to property condition. Inspection completed successfully. Price improvement! Move-in ready in Winter Park 32789. This beautifully renovated first-floor 2-bedroom, 2-bath condo features an open layout, custom soft-close cabinetry, high-end quartzite countertops, sleek matching appliances, and stylishly updated bathrooms, including a primary bath with elegant Italian porcelain tile. Major upgrades include a NEW A/C system and air handler and NEW tankless water heater, offering added efficiency and peace of mind. The monthly HOA delivers exceptional value, including water, trash, community insurance, exterior maintenance, lakeside pool access, and an extensive Spectrum package. The package includes high-speed internet, 150+ live TV channels, and streaming services including Disney+, Hulu, ESPN+, HBO Max, Paramount+, Peacock, discovery+, and AMC+ (a $250+ monthly value). Residents enjoy direct Lake Killarney access with a private community dock, clubhouse, pool, abundant guest parking, and a well-maintained community with funded reserves. Recent improvements include community-wide paving, new curbing, and refreshed landscaping, with additional improvements planned. Turnkey, thoughtfully updated, and ready for its next owner. Skip the renovations and start enjoying Winter Park living from day one. Schedule your tour today!

2500 Lee Road Unit 104, Winter Park
300 Carolina Avenue Unit 402C, Winter Park
$650,000
3 Beds ⋅ 2 Baths ⋅ Park West Condo SubDv. ⋅ 32789 Zip Code
EXCEPTIONAL ELEGANCE & VALUE IN DOWNTOWN WINTER PARK now for JUST $650,000! This spacious 3-bedroom, 2-bath top-floor residence in the coveted PARK WEST community presents a rare opportunity to enjoy the best of Winter Park living just one block from Park Avenue. This residence offers an impressive combination of generous living space, architectural character, privacy, and an unbeatable location. Situated on the fourth floor, this distinctive condo features vaulted ceilings, skylights, and abundant natural light, creating an open and airy atmosphere throughout. Expanded living areas provide flexibility for entertaining, relaxing, or working from home. The inviting living room features a fireplace, while the spacious kitchen offers ample cabinetry, generous counter space, and a convenient breakfast bar. The thoughtfully designed floor plan includes three generously sized bedrooms, including a primary suite with vaulted ceilings, a walk-in closet, and a spacious bathroom. The second bedroom features a charming sunroom alcove and can connect to the primary suite, offering the flexibility of a private den, sitting room, or home office. Storage is exceptional, with a large IN-UNIT laundry room and an oversized attic — features rarely found in condominium living. Recent improvements include a NEW HVAC system, NEW water heater, and plumbing updates, providing added peace of mind. A reserved covered parking space and plentiful guest parking add everyday convenience. Beyond the residence, Park West offers a gated entrance, community pool, tennis court, on-site community manager, and beautifully maintained grounds with extensive recent community improvements. Association fees also include sewer and trash service, making this an appealing low-maintenance, lock-and-leave lifestyle! And the location is truly extraordinary! Enjoy the freedom to stroll to Park Avenue's acclaimed restaurants, boutiques, sidewalk cafés, museums, and year-round events, all just moments from your front door. With its spacious three-bedroom floor plan, top-floor privacy, and exceptional storage, this is an outstanding opportunity to enjoy downtown Winter Park living at a compelling value!

300 Carolina Avenue Unit 402C, Winter Park
630 Killarney Bay Court Unit 3, Winter Park
$459,900
2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code
Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath. A convenient half bath is on the main level for guests. Enjoy community amenities including a swimming pool and a waterfront deck just 30 feet away, ideal for soaking in sunsets and lakeside breezes. All of this in an unbeatable location, just minutes from Winter Park Village, Trader Joe’s, Whole Foods, Park Avenue, dining, and shopping, with easy access to major roads for commuting.

630 Killarney Bay Court Unit 3, Winter Park
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