Winter Park Homes under $500,000

Winter Park Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Winter Park and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood! 

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Contact us today to find out how we can be of assistance to you!

Newest Winter Park Homes under $500,000

432 Hi Country Dr #10-4, Winter Park
$440,000
2 Beds ⋅ 1 Baths ⋅ 26-1403 MLS
Adorable 2-bedroom, first-floor condo in the heart of downtown Winter Park! Nestled among the trees in the Hi Country Haus community, this charming unit features an updated kitchen and bathroom and a peaceful, wooded setting. Conveniently located on the bus route and just minutes from downtown dining, shopping, trails, and year-round recreation. Never rented and well cared for.

432 Hi Country Dr #10-4, Winter Park
490 Kings Crossing Road Unit 331, Winter Park
$499,700
2 Beds ⋅ 2 Baths ⋅ 26-1343 MLS
Owner Financing Available! Top-floor Winter Park condo with Divide views, vaulted ceilings, and private balconies off the living room and every bedroom. Sleeps 8 -- ideal as a mountain getaway or turnkey short-term rental, ready to rent immediately after closing. On the free Winter Park bus route, with covered common-area parking and a private ski locker in the garage. Down the road from hundreds of miles of hiking, biking, and XC ski trails, and near the future gondola. Unwind in the renovated pool and hot tub after a day on the mountain. A rare investment opportunity -- contact the listing agent for financing details.

490 Kings Crossing Road Unit 331, Winter Park
145 Forest Trail Unit 9, Winter Park
$369,900
1 Baths ⋅ 26-1277 MLS
Get Into the Winter Park Market at an Exceptional Price! Looking for an affordable way to own in Winter Park without sacrificing the features that make a mountain property special? This studio checks all the boxes -- and then some. Enjoy Continental Divide views, hiking and biking trails right out the back door, and an easy walk to downtown Winter Park. This turnkey studio offers a smart, efficient layout with a Murphy bed, full bathroom, and new high-efficiency washer and dryer in the unit. One of the standout features is the private garage, giving you secure, convenient storage for your vehicle and all your Colorado toys -- a major advantage in the mountains. The property is also STR-friendly, opening the door to short-term rental potential when you're not enjoying it yourself. Combine that with low HOA dues and you have an attractive opportunity for both personal use and investment. Location is another major advantage. Walk to downtown Winter Park, step outside to nearby hiking and biking trails, and enjoy easy access to the resort. The property is also positioned to benefit from the planned Connect Winter Park Aerial Transit System (ATS) connecting downtown with the resort. The Town describes the project as a future transportation connection between the heart of downtown and Winter Park Resort. Whether you're looking for your first mountain getaway, a low-maintenance weekend retreat, or an STR investment, this is an opportunity to get into the Winter Park market at an attractive price while owning the amenities and location that matter.

145 Forest Trail Unit 9, Winter Park
411 Hi Country Drive Unit 4-12, Winter Park
$339,900
1 Beds ⋅ 1 Baths ⋅ 26-1247 MLS
Bask in the western sun from your deck on the river in this adorable 1 bd/1 ba condo. Fully remodeled, brand new kitchen w/full size range/oven, butcher block counters, & a full bathroom update w/tiled shower makes this quaint end-unit condo ready for its next owner! This is the ultimate starter condo for a local, first-time investor, or weekend getaway! Enjoy a private in-building washer/dryer reserved exclusively for owners. Just a short distance away, the clubhouse features a pool, hot tub, pool table, & weight room. You'll be able to catch the free shuttle bus to head to the slopes or make your way into town. The Idlewild trail system is also directly accessible from the clubhouse. This HOA includes heat and has replaced the central boiler, roof, sewer line & paved parking.

411 Hi Country Drive Unit 4-12, Winter Park
507 Hi Country Drive Unit #11-127, Winter Park
$469,000
2 Beds ⋅ 1 Baths ⋅ 26-1240 MLS
This bright, beautifully updated 2-bedroom condo offers the perfect combination of mountain charm, convenience, and location. Situated right on the river in the heart of downtown Winter Park, this cute and inviting unit puts you close to everything while offering a peaceful setting surrounded by mature trees and natural mountain ambiance. High Country Haus is a highly desirable community with excellent rental potential and fantastic amenities, including an indoor pool, fitness center, and convenient shuttle service to downtown and the ski area. After a day of skiing, hiking, biking, or exploring, relax to the sound of the river and enjoy the beautiful wooded surroundings. Whether you're looking for a mountain getaway, investment property, or a place to call your own, this 2-bedroom c is a fantastic opportunity in one of Winter Park's most convenient locations.

507 Hi Country Drive Unit #11-127, Winter Park
145 Forest Trail Unit 7, Winter Park
$485,000
1 Beds ⋅ 2 Baths ⋅ 26-1198 MLS
Mountain Getaway & Investment Opportunity in Winter Park. Enjoy the best of mountain living in this inviting 1-bedroom condo in Winter Park. Whether you're looking for a weekend retreat, a full-time escape, or a smart rental investment, this property offers an ideal combination of location, convenience, and mountain charm. Relax on the private deck while taking in beautiful mountain views, or head out for a day of skiing, hiking, biking, and everything Winter Park has to offer. The convenient location provides a short walk to the bus stop, making access to the ski area easy and stress free.

145 Forest Trail Unit 7, Winter Park
32 Telemark Drive Unit 102, Winter Park
$430,000
1 Beds ⋅ 1 Baths ⋅ 26-1194 MLS
Ski. Bike. Dine. Repeat. This ground-floor downtown Winter Park condo delivers a spacious living area, full kitchen, full bath, new windows, in-unit stackable washer/dryer, and an oversized private bedroom, plus low HOA dues for an unbeatable location. Tucked away and private, yet across from the new Winter Park Medical Center. The Foundry is just a block away for movies, bowling, dinner, and arcade games, with free summer concerts and the future gondola right in town. Grab your bike or XC skis for hundreds of miles of National Forest trails up the road. Hop the free Lift shuttle for a 10-minute ride to Winter Park Ski Resort. Ski season, festival season, or trail season, this location puts it all within reach. Schedule your showing today!

32 Telemark Drive Unit 102, Winter Park
79114 Us Hwy 40 Unit E-215, Winter Park
$385,000
1 Baths ⋅ 26-1163 MLS
Adventure starts right outside the door of this fully furnished Snowblaze studio, offering a comfortable and convenient home base for enjoying Winter Park year-round. The renovated kitchen features new cabinets, countertops, backsplash, sink, electric stove, and refrigerator, while updated finishes throughout give the space a fresh, inviting feel. With more space than a traditional studio, the flexible layout provides plenty of room to settle in after a day on the slopes or unwind before your next mountain adventure. A private entrance directly from the parking lot makes hauling gear in and out a breeze, while direct access to the clubhouse hot tub offers the perfect spot to warm up after a winter day or relax after summer adventures. The laundry room is conveniently nearby, and common garage parking provides added ease. Never rented and sold fully furnished, this turnkey condo is ready for ski weekends, summer escapes, and everything in between.

79114 Us Hwy 40 Unit E-215, Winter Park
520 Kings Crossing Road Unit A201, Winter Park
$499,000
2 Beds ⋅ 2 Baths ⋅ 26-1098 MLS
Enjoy the spectacular mountain views from the 3 decks from each room of this 2 bedroom 2 bath condo. Could have the most private location in Silverado complex. Located minutes from downtown Winter Park and access via shuttle bus, walking, biking or car. 10 minutes to Winter Park Resort. Complex has many amenities including outdoor hot tubs, laundry facilities, and storage. This condo is perfect for the Buyer who wants to pick their choice of remodel colors and types etc, Or this could be the perfect fix and flip for any investors.

520 Kings Crossing Road Unit A201, Winter Park
490 Kings Crossing Road Unit 321, Winter Park
$475,000
2 Beds ⋅ 2 Baths ⋅ 26-1066 MLS
This charming 2nd-floor condo blends classic cabin character with modern comfort, featuring warm wood paneling, natural textures, and a stunning stone fireplace that create the perfect alpine ambiance. With 2 bedrooms and 2 bathrooms, this inviting retreat comfortably sleeps at least 7 guests, including a spacious second bedroom with a queen bed and twin bunk setup--ideal for family and friends. The open-concept living area features upgraded hard surface flooring, cozy mountain finishes, and access to one of three private balconies where you can soak in the fresh alpine air and peaceful surroundings. Just steps from the free Lift shuttle with service throughout downtown Winter Park and directly to Winter Park Resort, this condo offers unbeatable convenience for year-round recreation. Spend the day exploring nearby Wolf Park, skiing world-class terrain, or enjoying everything the Fraser Valley has to offer, then return home to Silverado II's impressive amenities including a pool, hot tub, sauna, game room, and more. A perfect blend of Colorado cabin charm and resort-style convenience, this mountain getaway is ready for its next adventure.

490 Kings Crossing Road Unit 321, Winter Park
313 Iron Horse Way Unit 2013, Winter Park
$369,000
1 Baths ⋅ 26-1035 MLS
Best value at Iron Horse! Don't miss this cute studio with a super convenient, easily accessible location in this awesome ski-in, ski-out property at Winter Park resort. Enjoy all the great amenities from the year-round swimming pool, heated deck, hot tubs, ski storage, elevator access, full gym and more! Garage parking space is worth its weight in gold! Pop in and out as your ski legs get weary, but don't forget all the amazing summer biking, hiking, alpine sliding and festivals at the resort as well.

313 Iron Horse Way Unit 2013, Winter Park
78679 Us Hwy 40 Unit Building 2 unit 7, Winter Park
$480,000
3 Beds ⋅ 1 Baths ⋅ 26-1031 MLS
Quietly tucked along the Fraser River in central downtown Winter Park sits a bright end unit, 3 bedroom/ 1 bath condo. This condo is waiting for someone to update and create their own vision. Hanging cabinets and range have been removed and not replaced. The building features an impressive new deck and stairs with a peaceful riverfront garden gathering/sitting area. Roof replaced July 2026. Ideally located for those who want to be in the middle of downtown yet peacefully removed from the hustle of it. The sound of the river will be all you hear with windows open or enjoying some time on the deck out front of your mountain getaway.

78679 Us Hwy 40 Unit Building 2 unit 7, Winter Park
Start Your Search