Winter Park Homes with Other Exterior Features

Winter Park Homes with Other Exterior Features

Welcome to Winter Park, Florida – a picturesque city known for its charming streets, vibrant culture, and stunning natural beauty. Nestled just north of Orlando, Winter Park is a delightful blend of historic charm and modern conveniences. The city boasts a rich history, reflected in its beautifully preserved architecture and lush parks. Stroll along the scenic shores of Lake Osceola, or explore the eclectic boutiques and gourmet dining options on Park Avenue, where every corner offers a new adventure.

Winter Park is also celebrated for its exceptional arts scene, featuring the renowned Charles Hosmer Morse Museum of American Art, home to an extensive collection of Tiffany glass. The city hosts numerous cultural events and festivals throughout the year, drawing residents and visitors alike to celebrate the vibrant community spirit.

When it comes to real estate, Winter Park offers a diverse array of homes, each with unique exterior features that reflect the city’s character. From charming Mediterranean-style villas to contemporary masterpieces, the housing market caters to various tastes and lifestyles. Many homes are adorned with lush landscaping, inviting porches, and outdoor living spaces, perfect for enjoying Florida’s warm climate.

Whether you’re seeking a cozy bungalow or an elegant estate, Winter Park’s real estate options provide the perfect backdrop for your dreams. Embrace the charm of this enchanting city, where every home tells a story and every street invites exploration. Discover your ideal haven in Winter Park, where life is not just lived, but celebrated!

Newest Winter Park Homes with Other Exterior Features

$349,900
3 Beds ⋅ 2 Baths ⋅ Villas Of Casselberry Ph 4 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Comfort, style, and convenience come together in this beautifully maintained 3-bedroom, 2-bath home in the desirable Villas of Casselberry community. Soaring vaulted ceilings, an open floor plan, and abundant natural light create a spacious, inviting feel. The kitchen features stone countertops, ample cabinet space, and a cozy breakfast area, while the split-bedroom layout provides added privacy. The primary suite offers a walk-in closet and en-suite bath. Enjoy relaxing or entertaining on the screened patio overlooking the backyard. Community amenities include a pool, playground, and park, all just minutes from shopping, dining, and major highways for easy commuting.

3328 Hamlet Loop, Winter Park
$180,000
1 Beds ⋅ 1 Baths ⋅ Waterfall Cove At Winter Park Condominium D107 SubDv. ⋅ 32789 Zip Code
Don't miss out the great opportunity to own a unit in the heart of Winter Park Area. A perfect primary or secondary residence or investment home. Waterfall Cove is a great community with spacious pool, playground and lots of lush landscaping. Easy access to Major Highways a minute from I-4, bike away from Downtown Winter Park, close to major theme parks, major shopping area, restaurant, movie theater and a short drive to Cocoa Beach.

1695 Lee Road Unit D107, Winter Park
$499,900
3 Beds ⋅ 2 Baths ⋅ Flamingo Shores SubDv. ⋅ 32789 Zip Code
Welcome to your ideal single-story retreat in the heart of Winter Park's highly desirable Flamingo Shores neighborhood in zip 32789. This classic ranch-style home offers 1,979 square feet of thoughtfully designed living space, combining timeless mid-century character with everyday comfort in one of Central Florida's most sought-after locations. Designed for effortless living, the home's spacious single-level floor plan provides nearly 2,000 square feet of functional space with no stairs to navigate. At the center of the home, inviting living and gathering areas are anchored by a charming built-in fireplace, creating a warm and welcoming atmosphere for relaxing evenings or entertaining family and friends. Year-round comfort is ensured with central electric air conditioning and a reliable forced-air heating system. At the same time, public water and sewer service through the City of Winter Park provide dependable, low-maintenance utilities. Best of all, there are no HOA fees or restrictions, giving you the freedom to enjoy your property without additional regulations or monthly dues. Situated on a generous 0.26-acre lot, the home offers ample outdoor space for gardening, recreation, or future enhancements. Its exceptional location places you just minutes from the renowned dining, shopping, parks, and cultural attractions of downtown Winter Park.

351 Starling Road, Winter Park
$154,900
3 Beds ⋅ 2 Baths ⋅ Waterfall Cove SubDv. ⋅ 32789 Zip Code
Vacant! Great location! Must See! New paintinf interior, and new carpet. The best area at Winter Park, close to major shoppiing center,

1695 Lee Road Unit A101, Winter Park
$2,100,000
3 Beds ⋅ 2 Baths ⋅ 32792 Zip Code
A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park
$80,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

263 Scottsdale Square Unit 263, Winter Park
$80,000
2 Beds ⋅ 2 Baths ⋅ Winter Park Woods Condo SubDv. ⋅ 32792 Zip Code
Great location for homeowner or investor. Located close to FullSail and UCF and major roads, shopping, eating and more. Don't hesitate to see this one before it is gone!

303 Scottsdale Square Unit 303, Winter Park
$279,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Beautifully renovated 2 bedroom, 2 bathroom condo at 2305 Sun Valley in Winter Park, offering a fresh modern design and thoughtful updates throughout. The fully redesigned kitchen features sleek cabinetry, quartz countertops, GE stainless steel appliances, a marble tile backsplash, abundant storage, recessed lighting, and a clean open feel that connects seamlessly to the main living areas. Wood-look porcelain tile flooring runs throughout the home, creating a cohesive, attractive, and low-maintenance finish. The spacious living area features vaulted ceilings, skylights, updated ceiling fans, and sliding glass doors that fill the space with natural light and lead to a covered screened patio overlooking green space. The primary suite includes an updated double vanity and a beautifully redesigned bathroom with a separate tub and newly installed shower. The second bathroom also offers an updated vanity and clean neutral finishes. Additional highlights include a 2021 AC, 2021 water heater, updated fixtures, generous natural light, and a screened outdoor living space ideal for relaxing and enjoying Florida’s indoor-outdoor lifestyle. This move-in ready Winter Park condo combines modern style, comfort, and everyday functionality. Residents enjoy access to a sparkling community pool, clubhouse, tennis and pickleball, and a pet walk with waste stations. Monthly fees also include roof and exterior building maintenance, exterior pest control, and landscaping, adding convenience and long-term value.The location is hard to beat, just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, dining, entertainment, and nearby medical facilities.

2305 Sun Valley Cir, Winter Park, Fl 32792, Winter Park
$399,800
4 Beds ⋅ 2 Baths ⋅ Garden Lake Estates Unit 1 SubDv. ⋅ 32792 Zip Code
PRICE IMPROVEMENT! This 4-bedroom, 2-bath pool home in the heart of Winter Park is priced to sell and offers an incredible opportunity to make it your own. While the property could use some TLC, it features solid major updates and endless potential to add value. Situated on an oversized lot with NO HOA, this home features a spacious enclosed lanai, perfect for enjoying Florida living year-round. The thoughtfully designed split floor plan offers added privacy, with the primary suite separated from the secondary bedrooms. The recently updated kitchen serves as the heart of the home, while major improvements including a 2023 HVAC system, 2019 water heater, and newer roof, to provide peace of mind for years to come. Whether you're an investor or a buyer looking to personalize a home in one of Central Florida's most desirable locations, this property offers exceptional potential and a rare opportunity in Winter Park.

1610 Gladiolas Drive, Winter Park
$235,000
2 Beds ⋅ 1 Baths ⋅ Slovak Village SubDv. ⋅ 32792 Zip Code
Why Rent WHEN you can own this 2 bedroom 1 bath single car garage on this 1/2 duplex with NO HOA. Located conveniently to all major roads, shopping, schools and restaurants. New roof installed 2025. Don't hesitate to come view!

2712 Tortoise Cv, Winter Park
$389,000
3 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 06 2nd Rep SubDv. ⋅ 32792 Zip Code
SELLER FINANCING. Stunning 3-bedroom, 2-bath remodeled home with no HOA, ideally located on the border of Winter Park and Orlando. This move-in-ready property features a new roof installed in July 2025, an updated kitchen with beautiful granite countertops and brand-new appliances. Enjoy the perfect combination of comfort, style, and convenience with easy access to shopping, dining, schools, and major roadways. Don't miss this one! Schedule your private showing right away!

1605 Puritan Avenue, Winter Park
$328,000
2 Beds ⋅ 1 Baths ⋅ Stansbury Estates SubDv. ⋅ 32789 Zip Code
Welcome home to this charming and fully remodeled 2-bedroom, 1-bathroom gem nestled in the heart of Winter Park AND College Park. Located just minutes away from Downtown Orlando, Disney, Universal and Advent Health, this sought-after location offers convenience and comfort. This home boasts not only a prime location but also a cozy ambiance that will make you feel right at home. With its hardwood floors adding warmth and character, and the spacious fenced-in backyard providing privacy and room for outdoor activities, this property is ideal for those seeking the perks of Winter Park and College Park living as well as the fun outgoing, Orlando attractions.

2006 Cornell Avenue, Winter Park
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