Winter Park Homes for Sale

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Townhouse

1794 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,310Sqft
Under Construction. Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $825k! Eight exclusive lakefront units offer breathtaking views of Lake Killarney, two options of open floor plans, upgraded finishes throughout and the opportunity to purchase a private dock.
$897,887

Condominium

100 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,267Sqft
One or more photo(s) has been virtually staged. Opportunity to own a wonderful first floor unit at the Cloisters. This condo features two bedrooms and two full baths with generous room sizes.
$429,000

Single Family

826 W LYMAN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,753Sqft
Welcome home to the 1st place winner of the PARADE OF HOMES, located in Winter Park! Close to the hottest bars, restaurants and shops of Hannibal Square and Park Avenue and zoned for Audubon K-8 and Winter Park High School, this Alys Beach inspired perch built by Urban Perch-A Boutique Homebuilder was curated to maximize square footage creating an efficient and elegant home.
$747,900

Townhouse

1047 N KENTUCKY AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,786Sqft
Welcome Home! This stunning, modern townhome is perfectly located just minutes from Winter Park shops and restaurants. Designed by internationally recognized, and award-winning Architect Phil Kean, this unique 3 bedroom, 2.5 bathroom home with endless upgrades, on one of Winter Park's famous brick streets is ready for you to call it Home.
$695,000

Single Family

1712 ARBOR PARK DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
2Parking(s)
21Picture(s)
1,899Sqft
A Must See !!! ( No HOA ) Newly Remodeled 4/2 home in well Desired area in winter park. This property features new tiles floors , new hard wood flooring in bedrooms, newly renovated guest bath with tub and shower, new master bath with shower. As well as newly remodeled kitchen which includes new cabinets , granite counter tops , new stainless steel kitchen appliances.
$399,999

Single Family

1041 VIA MERANO COURT, WINTER PARK, Florida 32789

4Bedroom(s)
6Bathroom(s)
2Parking(s)
25Picture(s)
3,010Sqft
This beautiful Spanish Colonial home is located on a quiet cul-de-sac on Via Merano Court in the Winter Park school district. Recently renovated by Maroon Fine Homes, this two-story beauty includes 4 bedrooms all en suite, 4 full baths and two half baths, a formal dining room, living room and study.
$1,175,000

Townhouse

1760 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,407Sqft
Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer private boat slips and peaceful views of the lake.
$660,750

Townhouse

1792 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,341Sqft
Completed Model Unit!!! Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $825k! Eight exclusive lakefront units offer breathtaking views of Lake Killarney, two options of open floor plans, upgraded finishes throughout and the opportunity to purchase a private dock.
$1,000,000

Single Family

731 W SWOOPE AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
1Bathroom(s)
25Picture(s)
884Sqft
Location, location, location! Remodeled charmer is nestled on large corner lot in premier zipcode 32789. Walk to Hannibal Square restaurants, Park Avenue, Winter Park Village and Publix! Separate office, great room, 2 bedrooms and kitchen. Beautifully renovated home boasts heart of pine floors, Kraftmaid kitchen cabinets, granite counter tops and stainless steel appliances.
$299,900

Townhouse

1798 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
4Picture(s)
2,341Sqft
Under Construction. Under Construction. Unparalleled opportunity to purchase a lakefront townhome in the Lake Killarney Townhomes community - with lakefront units starting at $850k! Eight exclusive lakefront units offer breathtaking views of Lake Killarney, two options of open floor plans, upgraded finishes throughout and the opportunity to purchase a private dock.
$825,000

Condominium

102 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
2,080Sqft
One of the best remodels in the Cloisters. New kitchen and new bathrooms. Wood floors throughout this three bedroom, two and a half bath almost maintenance free condo. Perfect for someone looking for lock and leave capability. Split plan with bright and open rooms and a treetop city view from balcony. Just one block from magnificent Park Avenue shops and restaurants.
$785,000

Lots And Land

797 PINETREE ROAD, WINTER PARK, Florida 32789

11Picture(s)
0.94Acre
RARE opportunity to build your Estate Home on sought after Lake Maitland, on the WINTER PARK CHAIN OF LAKES! You will enjoy this phenomenal location that is in the of the heart of the Via’s neighborhood and tucked away on a quiet, peaceful street. Just a short stroll to the Winter Park Racquet Club and minutes to Downtown Park Ave restaurants and shops.
$2,895,000

Townhouse

1808 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,276Sqft
Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer private boat slips and peaceful views of the lake.
$599,750

Condominium

690 OSCEOLA AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,148Sqft
Now is your chance to live on the highly desired Winter Park Chain of lakes! Don't miss out on this impeccably maintained 2 bedroom 2 bathroom condo offering a beautifully updated kitchen with granite counters, wood cabinetry & stainless steel appliances. This spacious unit lives bigger than the 1148 heated square footage and masters the smooth flow of the living space.
$329,000

Townhouse

1812 MONDRIAN CIRCLE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
2,276Sqft
Pre-Construction. To be built. Pre-Construction. To be built. Perfectly located between the tranquility of nature and the best in local shopping, restaurants and bars. Lake Killarney Townhomes offer private boat slips and peaceful views of the lake.
$610,750

Single Family

1661 ORANGE AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
3Picture(s)
2,652Sqft
Pre-Construction. To be built. Pre-construction! Perfectly situated - close to Winter Park shopping and dining, Mead Botanical Gardens, College Park and Lake Ivanhoe. Great transport links with I-4 access nearby and a short drive to Sun Rail stations. Plans for a stunning 4 bed, 3 bath, 2,652 sqft townhome have been developed by one of Winter Park’s premier custom home builders.
$819,000

Condominium

100 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,267Sqft
The Cloisters! A fabulous Winter Park location! The Cloisters is just a short walk off Park Avenue, convenient to restaurants, shops, banking, bakeries, coffee shops, the library, the park. Sun Rail/Amtrak and so much more. Situated on Lake Osceola with on site docking for your boat available, this unit overlooks the pool, gardens and has a lake view.
$530,000

Residential

511 W CANTON AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
5Parking(s)
10Picture(s)
8,910Sqft
Masterful design and modern luxury are uniquely embodied in this Spectacular Mid-Century Modern Estate. Stylish simplicity, extensive use of glass, and open design forge a connection with nature. Expansive entertaining spaces flow outside to the Grande Courtyard.
$3,350,000

Rental

2546 PASSAMONTE DRIVE, WINTER PARK, Florida 32792

3Bedroom(s)
3Bathroom(s)
1Parking(s)
24Picture(s)
1,765Sqft
3/2.
$1,795

Condominium

3371 RIVER VIEW WAY, WINTER PARK, Florida 32792

3Bedroom(s)
3Bathroom(s)
20Picture(s)
1,151Sqft
Come see this updated spacious 3 Bedroom  2.5 bath condo!  This 2-story townhome style condo features an open floor plan with inside laundry room, dry bar, storage room and fenced in patio with no rear neighbors.
$165,000

Townhouse

3200 OAK LAWN PLACE, WINTER PARK, Florida 32792

2Bedroom(s)
2Bathroom(s)
25Picture(s)
990Sqft
Freshly Cleaned 2 bedroom Townhome style Condo located in a well kept Winter Park community of Hidden Oaks. First floor offers a living room/dining room combo with a wet bar, half bath, eat-in-kitchen, laundry closet with a full size washer and dryer, INCLUDED. CORNER Unit with a private, FENCED patio/courtyard off dinette great for entertaining and gardening.
$122,500

Townhouse

2612 PASSAMONTE DRIVE, WINTER PARK, Florida 32792

3Bedroom(s)
3Bathroom(s)
1Parking(s)
19Picture(s)
1,554Sqft
Location, Location, Location! This well kept townhouse is located within a gated community with excellent schools in the area. This 2 story townhouse offers 3 bedrooms, 2 full bathrooms and a guest bathroom with an attached one car garage.
$225,000

Single Family

5405 N LAKE BURKETT LANE, WINTER PARK, Florida 32792

3Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,806Sqft
Welcome Home to this recently updated 3 bedroom, 2.5 bath home in the sought after Trinity Bay neighborhood. (new A/C 2020) Upon entry you're greeted with an open and inviting living and dining area with all new laminate flooring, baseboards and fresh interior paint throughout the entire downstairs.
$320,000

Commercial Lease

1477 W FAIRBANKS AVENUE, WINTER PARK, Florida 32789

21Picture(s)
2,544Sqft
Top floor of Established Winter Park Office location. Recently Remodeled Reception and Waiting area,9 Offices (2 with Fireplaces) plus Conference Room and large Kitchen/Congregating Room. Private Entrance, Close proximity to Downtown Winter Park, Winter Park Village and easy access to I-4.
$18

Rental

315 E NEW ENGLAND AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
5Bathroom(s)
2Parking(s)
25Picture(s)
3,817Sqft
BEAUTIFUL WINTER PARK PENTHOUSE oriented in the most private section of the Jewel of Winter Park! Villa Siena is located 2 blocks off Park Avenue and is directly across from the chic Alfond Inn.
$8,500

Rental

664 WORTHINGTON DRIVE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
11Picture(s)
1,527Sqft
Spacious home in Winter Park on a quiet tree-lined street, features new carpet, fresh paint, updated master bath, walk-in closet, and screened, newly landscaped private back patio. Convenient to shopping, restaurants and all major roads.
$2,300

Rental

2500 LEE ROAD, WINTER PARK, Florida 32789

1Bedroom(s)
1Bathroom(s)
13Picture(s)
645Sqft
Nice ground-floor FURNISHED condo near the pool & lakefront. Newer energy efficient windows. Lakeside Manor Condominiums is located on beautiful Lake Killarney & minutes from Rollins College, Winter Park Village, Trader Joes, restaurants, shopping & beautiful downtown Winter Park. Community dock, boat ramp, pool and clubhouse offer everything you need for a relaxed lifestyle.
$1,000

Single Family

171 N PHELPS AVENUE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
3,424Sqft
With 3,424 sf of living space, this beautifully renovated and impeccably maintained 4 bedroom, 3 bath home will surprise and delight! The large, open floor plan includes a stunning gourmet kitchen with Wolf gas cooktop, Miele double ovens and Sub Zero built-in refrigerator. The kitchen bar area includes 2 wine refrigerators and a huge picture window overlooking the beautiful backyard.
$894,500

Single Family

2843 RIDDLE DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
1,970Sqft
Welcome to the Mid Century Modern Charm of Sunshine Gardens! A prime location, minutes from enjoying Winter Park Avenues Shoppes and Restaurants! Also minutes from the eclectic and Historic College Park as well as Maitland! Proximity to major highway I4 gets you to Downtown Orlando in minutes and makes for easy commuting.
$315,000

Residential

140 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
2Parking(s)
24Picture(s)
1,758Sqft
URBAN LUXURY LIVING IN THIS AWARD WINNING BUILDING “ THE LANDMARK “ IN DOWNTOWN WINTER PARK. LOCATED JUST STEPS FROM PARK AVE SHOPS AND DINING, THIS EXCLUSIVE 2 BR, 2 BTH CORNER PENTHOUSE SINGLE STORY SUITE WITH 3 PRIVATE BALCONIES WAS RECENTLY REMODELED BY TED MAINES INTERIORS WITH LUXURY SELECTIONS THROUGHOUT.
$1,099,000

Single Family

1292 HOWELL BRANCH ROAD, WINTER PARK, Florida 32789

4Bedroom(s)
6Bathroom(s)
3Parking(s)
13Picture(s)
4,573Sqft
Pre-Construction. To be built. “Pre-Construction. To be built.” VIA VENETO is an exclusive new subdivision of four (4) oversized Lakefront Lots in Winter Park's most desired Via's neighborhood. Enjoy a rare opportunity to build your dream home of 6200+ square feet right on Lake Temple. Claim your spacious Florida oasis away from it all, yet close to everything.
$1,875,000

Single Family

1652 BERKSHIRE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
18Picture(s)
1,498Sqft
Your search is over! Location, Location, Location! This updated 3 bedrooms/2 baths Winter Park home is located in the highly sought after Orwin Manor neighborhood which is conveniently located between Winter Park's Park Avenue and Downtown Orlando, Walking distance to Advent Health Hospital and just minutes to Park Avenue's shopping and restaurants.
$339,900

Condominium

350 KILLARNEY BAY COURT, WINTER PARK, Florida 32789

2Bedroom(s)
3Bathroom(s)
1Parking(s)
25Picture(s)
1,428Sqft
Expect to be impressed and enjoy the beautiful Florida sunsets with this updated Winter Park condo with access to the beautiful spring fed Lake Killarney. This tucked away and quiet small community has a lovely community pool, open dock for fishing, and an area for you to store your canoe or kayak. Unique for condo living, it also offers a one-car carport for your parking needs.
$307,500

Condominium

225 E CANTON AVENUE, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
25Picture(s)
1,057Sqft
Come find your new home - a truly rare find in the highly-regarded Village of Winterset! Right in the heart of Winter Park and JUST ONE BLOCK AWAY FROM PARK AVE. These units rarely come onto the market (especially a corner/end unit) so don't miss your opportunity. When you enter, you'll notice the open the floorplan with plenty of natural light coming through the windows.
$450,000

Condominium

147 S INTERLACHEN AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,272Sqft
One or more photo(s) has been virtually staged. Just completed in downtown Winter Park's distinctive Interlachen Place, this third-floor condo was entirely reconfigured by a renowned local builder to optimize light and space into an open and flowing floor plan with timeless, refined finishes.
$1,750,000

Single Family

1740 VIA PALERMO, WINTER PARK, Florida 32789

5Bedroom(s)
6Bathroom(s)
3Parking(s)
25Picture(s)
5,259Sqft
Located in the heart of Winter Park, this exceptional and well appointed estate home sits on an oversized lot in the highly desirable “Vias” area. Dutch Provincial in style, this home was a Parade of Homes collaboration built in 2018 by Ira Kitograd of IBK Custom Homes and Z Properties.
$2,900,000

Single Family

171 OAK GROVE ROAD, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
1Parking(s)
6Picture(s)
1,170Sqft
Great investment opportunity with tenants and lease in place until April 18th, 2021 at $1240 a month. This quaint home was updated a few years back and features neutral paint throughout and ceramic tile flooring throughout.
$199,900

Single Family

2524 Sweetwater Trail, WINTER PARK, Florida 32789

3Bedroom(s)
2Bathroom(s)
2Parking(s)
25Picture(s)
1,728Sqft
Immaculately Maintained 3/2 Home In The Desirable Winter Park,Fl City Limits! This 1728 Sf Home Has A 2 Car Attached Garage With Work Space And Above Head Storage. Screened In Pool And Patio Area Which Boasts A Custom Built Water Feature And Decorative Halogen Lighting.
$410,000

Townhouse

135 W SWOOPE AVENUE, WINTER PARK, Florida 32789

3Bedroom(s)
3Bathroom(s)
2Parking(s)
24Picture(s)
2,457Sqft
HUGE PRICE REDUCTION!! This exquisite property is worthy of your attention! If you are thinking of downsizing or just want a more carefree lifestyle, consider this elegant town home. This is city living at its finest in the best little city in the world. Forget the upkeep and maintenance of the big house, step out your door and walk your Park Ave neighborhood.
$1,450,000

Single Family

1790 WINDSOR DRIVE, WINTER PARK, Florida 32789

4Bedroom(s)
2Bathroom(s)
2Parking(s)
23Picture(s)
1,695Sqft
LOCATION LOCATION LOCATION This home has been lovingly cared for and is ready for a new family. It could also be the perfect location to build your dream home. Large lot would make the perfect setting. Easy walk to Lakemont Elementary. Close to Winter Park’s highly desirable Park Ave with dining and shopping.
$450,000

Lots And Land

1790 WINDSOR DRIVE, WINTER PARK, Florida 32789

1Picture(s)
0.27Acre
LOCATION LOCATION LOCATION This home has been lovingly cared for and is ready for a new family. It could also be the perfect location to build your dream home. Large lot would make the perfect setting. Easy walk to Lakemont Elementary. Close to Winter Park’s highly desirable Park Ave with dining and shopping.
$450,000

Condominium

140 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,450Sqft
Luxury living in the Landmark Building - Winter Park’s premiere address for privacy and proximity to all Park Ave has to offer.
$1,590,000

Single Family

741 DIXIE PARKWAY, WINTER PARK, Florida 32789

4Bedroom(s)
3Bathroom(s)
2Parking(s)
25Picture(s)
2,989Sqft
New listing in Green Oaks/Park Grove neighborhood. Beautiful traditional home with amazing curb appeal and large, oversized lot. Interior features approximately 3,000 SF including 4 bedrooms, 2.5 baths, formal living and dining rooms, a gathering room with fireplace, and charming kitchen with eat-in space. Wood floors flow throughout most of the interior, including the bedrooms.
$925,000

Single Family

2825 ROXBURY ROAD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,261Sqft
Well-loved Winter Park home close to everything - College Park, minutes to downtown Orlando, minutes to Cranes Roost. This updated home shines! Gourmet kitchen with stone tile backsplash, new appliances, maple cabinets, granite countertops and bar, and new tile flooring. The hardwood floors are original, pampered, and WOW throughout the house.
$285,000

Condominium

311 E MORSE BOULEVARD, WINTER PARK, Florida 32789

2Bedroom(s)
2Bathroom(s)
1Parking(s)
25Picture(s)
1,964Sqft
Sweeping views of Winter Park's Lake Osceola. Like-new contemporary home designed by Lamar Design and rebuilt by Brannon Construction in 2015. Unique kitchen, baths and all-purpose second bedroom. Includes one of only three lovely, private patios in the 73 unit condominium complex. Deeded, covered boat slip, and secure, designated indoor parking.
$1,300,000

Single Family

1731 OAKHURST AVENUE AVENUE, WINTER PARK, Florida 32789

5Bedroom(s)
7Bathroom(s)
3Parking(s)
25Picture(s)
4,398Sqft
Under Construction. This custom 5-Bd/5-Ba/2-HBa contemporary/transitional pool home has been uniquely designed with an exceptional selection of neutral materials, finishes, and lighting to create a warm and elegant atmosphere.
$1,695,000

Single Family

948 POINCIANA LANE, WINTER PARK, Florida 32789

4Bedroom(s)
4Bathroom(s)
2Parking(s)
25Picture(s)
3,740Sqft
Welcome home to 948 Poinciana Lane in Winter Park’s most sought-after neighborhood, the Vias. This four-bedroom, three-and-one half bath pool home offers a sophisticated interior with formal living and dining, yet a modern and open design for every day living.
$1,315,000

Lots And Land

1851 WINDSOR DRIVE, WINTER PARK, Florida 32789

1Picture(s)
0.24Acre
Prime Winter Park location. Value is in the land. Build your dream home on this large lot.
$399,000
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