Winter Park, FL Homes

• 

  

  

  /34

  $845,000

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft

  734 Maryland Ave, Winter Park, FL 32789

  Fully renovated 1926 historic Winter Park bungalow with separate guest cottage in the heart of the Winter Park Historic District. Surrounded by a beautiful tree-lined street with brick roads, you'll be impressed by the magnificent curb appeal. Ideally located within a short distance to Park Avenue, Rollins College and the Winter Park Chain of Lakes community dock, just minutes from the Winter

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  734 Maryland Ave, Winter Park, FL 32789
• 

  

  

  /11

  $1,252 - $1,726 per month

  Solis at Winter Park

  1-2 Beds

  7502 Sun Key Blvd, Winter Park, FL 32792

  Property Tours AvailableWe are now welcoming virtual, self-guided, and agent led tours. Please contact us today to schedule your appointment.Solis at Winter Park, FL Apartments boast premier location great for both business and leisure. The wide selection of one and two bedroom apartments ensure you will find a layout that fits your needs perfectly. Every apartment home comes decked out with huge

  7502 Sun Key Blvd, Winter Park, FL 32792
• 

  

  /2

  $170,000 Sold Jul 03, 2025

  • 1,067 Sq Ft
  • $159/SF
  • 58 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1970

  200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792

  FOUR SEASONS CONDO IN Winter Park is Centrally located. Great community with a clubhouse, a fitness center recently renovated, 3 swimming pools, tennis courts, and shuffleboard court. Close by you are only a short walk to Cady Way Park for baseball and soccer fields as well as other playgrounds. This 2 bedrooom/2 bath unit has been updated with laminate flooring, ceiling fans, all appliances

  Patricia Wojewoda BETTER HOMES & GARDENS RE STAR

  200 Saint Andrews Blvd Unit 2804, Winter Park, FL 32792
• 

  

  

  /41

  Est $1,549,722 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 3,287 Sq Ft

  1005 S Pennsylvania Ave, Winter Park, FL 32789

  1005 S Pennsylvania Ave, Winter Park, FL 32789
• 

  

  

  /30

  $775,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,076 Sq Ft

  620 Darcey Dr, Winter Park, FL 32792

  New roof scheduled for replacement at end of July 2025. Charming brick Winter Park home in the desirable Brookshire Heights neighborhood. This home features four bedrooms, two baths, over 2,076 square feet of natural sunlight flowing throughout, enclosed back porch and a fully fenced backyard. Beautiful curb appeal with a long extended driveway, great for large gatherings, parking your boat, RV

  Michael Domi PREMIER SOTHEBY'S INTL. REALTY

  620 Darcey Dr, Winter Park, FL 32792
• 

  

  /24

  $2,799 per month

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Townhouse for Rent

  2461 Firstlight Way, Winter Park, FL 32792

  GREAT LOCATION!! Come and check out one of Winter Park's newest neighborhoods, Hawks Crest! This stunning townhome has brand new paint throughout and features 3 bedrooms, 2.5 bathrooms, an open concept living space perfect for entertaining, high ceilings, a screened in lanai upgrade, 2 car garage, large pantry, stainless steel appliances, spacious rooms, tons of storage, a HUGE master bedroom

  Steve Simpson 407 PROPERTIES

  2461 Firstlight Way, Winter Park, FL 32792
• 

  /2

  $750,000 Sold Jul 03, 2025

  • 960 Sq Ft
  • $781/SF
  • 263 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1941

  731 Midget Dr, Winter Park, FL 32789

  SPECTACULAR WINTER PARK OPPORTUNITY! This oversized corner lot in Fairbanks Park overlooking Lake Midget and Lake Midget Park is a rare opportunity to build your dream home in Winter Park. The 2-bedroom/1-bath home, original owners since 1941, is available for renovation or new construction. Serene views of Lake Midget from the front porch, that can’t be beat. New restaurant and retail space is

  Laura Heidrich COLDWELL BANKER RESIDENTIAL RE

  731 Midget Dr, Winter Park, FL 32789
• 

  /2

  Est $739,678 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,582 Sq Ft

  1304 Blue Stem Ln, Winter Park, FL 32792

  1304 Blue Stem Ln, Winter Park, FL 32792
• 

  

  /21

  $949,900 Open Sun 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,536 Sq Ft

  2823 Wright Ave, Winter Park, FL 32789

  Here’s your chance to own something truly special in Winter Park! This gorgeous lakefront home sits on over HALF AN ACRE, a rare find in this area - allowing opportunity to BUILD YOUR DREAM HOME! Step inside to find a thoughtfully updated kitchen featuring high-end appliances, custom cabinetry, and designer finishes, ideal for both entertaining and everyday living. The home boasts new windows

  Tal Busidan TAL BUSIDAN PA

  2823 Wright Ave, Winter Park, FL 32789
• 

  

  /31

  $1,580 - $1,874 per month

  POSTE Winter Park

  1-2 Beds

  800 Semoran Park Dr, Winter Park, FL 32792

  Welcome to Poste Winter Park, where the beauty of classic period architecture meets the modern comforts of today. Nestled in the heart of trendy Winter Park, Florida, our community is your gateway to a vibrant, convenient, and tranquil lifestyle. Poste Winter Park offers a boutique feel with newly remodeled facilities, spacious floor plans, and signature customer service. Located just across from

  800 Semoran Park Dr, Winter Park, FL 32792
• 

  /2

  $428,000 Sold Jul 02, 2025

  • 1,468 Sq Ft
  • $292/SF
  • 22 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1965

  3520 Balsam Dr, Winter Park, FL 32792

  Welcome to this beautifully updated home that blends charm, space, and modern upgrades—an expansive OVER 1/4 ACRE LOT with NO REAR NEIGHBORS and NO HOA. 4 Bed/2Ba with a 2-car Garage! You’ll love the BRAND NEW ROOF (April 2025) and the NEW EXTERIOR PAINT (2025). Inside, the COMPLETELY RENOVATED KITCHEN features stunning QUARTZ COUNTERTOPS and MODERN SHAKER STYLE CABINETS. The DINING SPACE offers

  Cece Wong EXP REALTY LLC

  3520 Balsam Dr, Winter Park, FL 32792
• 

  

  /15

  Est $124,079 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  192 Scottsdale Square Unit 192, Winter Park, FL 32792

  192 Scottsdale Square Unit 192, Winter Park, FL 32792
• 

  

  /26

  $799,900

  • 2 Beds
  • 2 Baths
  • 1,382 Sq Ft

  311 Cortland Ave, Winter Park, FL 32789

  Location, location, location! Whether you're ready to build your dream home or simply want to enjoy life in Central Florida’s most prestigious neighborhood at an unbeatable value, this delightful mid-century 2-bedroom, 2-bathroom home offers endless possibilities. Lot size is approximately 130 ft X 78 ft. Perfectly positioned just minutes from Park Avenue, Rollins College, and Lake Osceola, this

  Amy Turner KELLER WILLIAMS WINTER PARK

  311 Cortland Ave, Winter Park, FL 32789
• 

  

  /20

  $1,525 per month

  • 2 Beds
  • 2 Baths
  • 1,035 Sq Ft
  • Condo for Rent

  3054 George Mason Ave Unit D, Winter Park, FL 32792

  Stunning 2-Bed/2-Bath Condo in The Colonies – Winter Park Living at Its Best!Welcome home to this beautifully maintained 2-bedroom, 2-bathroom condo located in the highly desirable Colonies community in Winter Park! This spacious 1,035 sq ft second-floor unit offers the perfect blend of comfort, style, and convenience—just minutes from UCF, Full Sail University, Valencia College, shopping,

  Alejandro Bastidas MY REALTY GROUP, LLC.

  3054 George Mason Ave Unit D, Winter Park, FL 32792
• 

  /2

  $382,000 Sold Jul 02, 2025

  • 1,355 Sq Ft
  • $282/SF
  • 34 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1955

  1909 Edwin Blvd, Winter Park, FL 32792

  Great location of this 1950's ranch home in need of love. The home sits on a nice sized corner lot in the Winter Park schools district. The vaulted ceilings with a almost floor to ceiling windows makes the home feel nice and open with tons of natural light. This charming home has 3 bedrooms, 2 bathrooms, laundry room and open floor plan living spaces.

  Brian Craib OLDE TOWN BROKERS INC

  1909 Edwin Blvd, Winter Park, FL 32792
• 

  

  /25

  Est $222,233 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,127 Sq Ft

  200 Saint Andrews Blvd Unit 2808, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 2808, Winter Park, FL 32792
• 

  

  /19

  $198,000

  • 1 Bed
  • 1 Bath
  • 753 Sq Ft

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792

  Price adjusted! Fully Renovated 1-Bedroom First-Floor Condo – Stylish & Convenient Living. Move-in ready! Gorgeous new flooring throughout, sophisticated modern lighting, freshly painted walls with contemporary baseboards and trim, impeccably styled. Welcome to 4768 Tangerine Ave #4768, a beautifully renovated one-bedroom, one-bath condo on the first floor, boasting modern quartz

  Christopher Franqui PROPERTY OUTLET INTERNATIONAL

  4768 Tangerine Ave Unit 4768, Winter Park, FL 32792
• 

  

  /30

  $1,802 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Commu...

  1-2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar—all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
• 

  /2

  $649,000 Sold Jul 02, 2025

  • 1,835 Sq Ft
  • $354/SF
  • 126 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1957

  958 Dunraven Dr, Winter Park, FL 32792

  *** WONDERFUL WINTER PARK ***LOCATION, LOCATION, LOCATION!!! This Fantastic 4 Bedroom 3 Bath Home is Welcoming for Everyone. From the moment you enter this Fabulous home you will know you have made the right choice. The Beautiful Wood Floors are predominant in the Home. The Large Kitchen with Quartz Counters and Stainless Steel Applicance will please Chefs of every level. The Wood Burning

  Rhonda Hunter COLDWELL BANKER RESIDENTIAL RE

  958 Dunraven Dr, Winter Park, FL 32792
• 

  

  /33

  Est $487,722 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2260 Shadowland Loop, Winter Park, FL 32792

  2260 Shadowland Loop, Winter Park, FL 32792
• 

  

  /17

  $195,000

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  1000 S Semoran Blvd Unit 604, Winter Park, FL 32792

  This second floor Winter Park Condo has been beautifully renovated. The kitchen renovation includes beautiful cabinets, newer stainless-steel appliances, granite counter tops, and removing two walls for an open concept feature exposing complete view to the dining and living room. Both bathrooms have been renovated. Guest bathroom has a tiled wall in the tub/shower and new vanity. Primary bathroom

  Jeff Stewart WEICHERT REALTORS HALLMARK PROPERTIES

  1000 S Semoran Blvd Unit 604, Winter Park, FL 32792
• 

  

  /14

  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • House for Rent

  5323 Poinsetta Ave, Winter Park, FL 32792

  Winter Park and NO HOA!! Newly remodeled 3/2 1,500 sqft $2,350/mo. Just a 1 minute car ride or 5-7 minute walk to Eastbrook Elementary. Remodeled kitchen with all the bells and whistles (new cabinets, countertops, backsplash, faucet, lights, and appliances - you get the idea, it's fancy!). Remodeled bathrooms with subway tiles, new tub, new vanities, new countertops, new toilets, new lighting &

  Ginnie England MAGNOLIA PROPERTY SALES

  5323 Poinsetta Ave, Winter Park, FL 32792
• 

  /2

  $2,440,000 Sold Jul 01, 2025

  • 3,770 Sq Ft
  • $647/SF
  • 41 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 2016

  1700 Palm Ave, Winter Park, FL 32789

  One lucky Buyer's gain is this Seller's bittersweet goodbye. A job relocation has these homeowners leaving behind a home they absolutely love, and now, you can make 1700 Palm Ave. yours! Modern sophistication and everyday functionality come together seamlessly in this exceptional Winter Park residence.With 3,770 square feet of thoughtfully designed living space, this 4-bedroom, 4.1-bath home

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1700 Palm Ave, Winter Park, FL 32789
• 

  

  /18

  Est $215,955 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
• 

  

  /23

  $998,000

  • 4 Beds
  • 3.5 Baths
  • 4,088 Sq Ft

  1319 Heavenly Cove, Winter Park, FL 32792

  FULLY FURNISHED HOME THAT IS MOVE-IN READY! ALL FURNITURE INCLUDED IN THE SALES PRICE! Amazing home located in a quiet gated subdivision in Winter Park near Trinity Prep. The home provides a wonderful layout with high ceilings and an open concept – perfect for entertaining. Updated kitchen with clean white cabinets, spacious chef’s island, and GE stainless steel appliances to cook a delicious

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  1319 Heavenly Cove, Winter Park, FL 32792
• 

  

  /35

  $876 - $1,373 per month

  GOLDEN OAKS

  2-3 Beds

  7701 Acorn Woods Cir, Winter Park, FL 32792

  Golden Oaks Apartments is your destination for quality, affordable living, offering spacious two and three-bedroom apartment options designed to meet your needs. Located in a serene, peaceful area, our community combines the tranquility of a residential neighborhood with the convenience of nearby shopping, dining, and entertainment. With income restrictions in place to ensure affordability,

  7701 Acorn Woods Cir, Winter Park, FL 32792
• 

  /2

  $397,000 Sold Jul 01, 2025

  • 1,236 Sq Ft
  • $321/SF
  • 83 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  1109 Denton Rd, Winter Park, FL 32792

  NEW ROOF to be installed prior to closing. Look no further than this charming 3-bedroom, 2-bathroom pool home located in the highly desirable Winter Park community of Winter Park Estates. Sitting on 1⁄4 of an acre with no HOA, this home is just what you’ve been searching for! Head inside to find the beautifully updated kitchen featuring quartz and butcher block countertops, stainless steel

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
• 

  

  /42

  Est $489,904 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792
• 

  

  /28

  $200,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

  Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
• 

  

  /67

  $5,050 per month

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • House for Rent

  2627 Verona Trail, Winter Park, FL 32789

  Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  2627 Verona Trail, Winter Park, FL 32789
• 

  /2

  $85,000 Sold Jul 01, 2025

  • 1,020 Sq Ft
  • $83/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  198 Scottsdale Square Unit 198, Winter Park, FL 32792

  Great investment property

  Edward Lee LA ROSA REALTY ORLANDO LLC

  198 Scottsdale Square Unit 198, Winter Park, FL 32792
• 

  

  /89

  Est $1,346,624 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  3629 Midiron Dr, Winter Park, FL 32789

  3629 Midiron Dr, Winter Park, FL 32789
• 

  

  /20

  $192,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792

  Welcome to this beautifully updated 2 bedroom/ 2 bath  first floor condo.  This open floor plan has tiled flooring throughout the common areas, along with granite counter tops in the kitchen and bathrooms. The energy efficient AC was replaced in December 2023!  Included appliances are: Washer, dryer, stove, microwave, dishwasher, and refrigerator are all less than 5 yrs old. The garbage disposal

  Ralph Harvey LISTWITHFREEDOM.COM

  3651 N Goldenrod Rd Unit 102, Winter Park, FL 32792
• 

  

  /41

  $1,625 - $1,895 per month

  The Lofts of Winter Park Village

  1 Bed

  520 N Orlando Ave, Winter Park, FL 32789

  Discover urban living at its best in Winter Park's The Lofts! Offering a unique 2-level loft, the allure of high ceilings, oversized windows, and industrial touches reminiscent of New York City's ambiance. Step into the heart of the action, surrounded by Regal Movie Theatre, Crisp & Greens, Jeni's Ice Cream, Cheesecake Factory, Bar Italia, Publix, Free People, and much more. This unique urban

  520 N Orlando Ave, Winter Park, FL 32789
• 

  /2

  $80,000 Sold Jul 01, 2025

  • 1,020 Sq Ft
  • $78/SF
  • 32 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1974

  257 Scottsdale Square Unit 257, Winter Park, FL 32792

  Great Winter Park location SINGLE UNIT, 1st floor, 2 bedroom, 2 bath well mantain condo with tile flooring. Close to Full Sail University, University of Central Florida,Rollins College,Orlando International Airport, Express Way 408 and 417,Baldwin Park,Downtown Orlando, Restaurants & Shopping. Fantastic Opportunity for Investor. Tenant Occupied

  Loida Rodriguez RC REALTY GROUP INC

  257 Scottsdale Square Unit 257, Winter Park, FL 32792
• 

  

  /38

  Est $758,498 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft

  1477 Lone Feather Trail, Winter Park, FL 32792

  1477 Lone Feather Trail, Winter Park, FL 32792
• 

  

  /39

  $900,000

  • 4 Beds
  • 2 Baths
  • 2,237 Sq Ft

  1018 Turner Rd, Winter Park, FL 32789

  Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday feel like a lakeside retreat. Major

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1018 Turner Rd, Winter Park, FL 32789
• 

  

  /13

  $3,195 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

  Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit featuring a nice kitchen with stainless steel appliances, and an updated flooring with luxury vinyl plank. This unit has an indoor heated swimming pool with an exercise room. This property is located near all of the main central Florida colleges. Come and enjoy with your family

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
• 

  /2

  $81,000 Sold Jul 01, 2025

  • 756 Sq Ft
  • $107/SF
  • 10 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  262 Scottsdale Square Unit 262, Winter Park, FL 32792

  Opportunity awaits in this 1-bedroom, 1-bath condo located in the heart of Winter Park! This unit is ideally situated near schools, shopping, and dining, offering unmatched convenience. With a little TLC, you can make it your own or turn it into a fantastic investment property.The community offers great amenities, including a pool, picnic area, kids’ playground, and tennis courts (currently

  Edward Lee LA ROSA REALTY ORLANDO LLC

  262 Scottsdale Square Unit 262, Winter Park, FL 32792
• 

  /2

  Est $478,761 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  Unlisted Address

  Unlisted Address

Showing Results 201 - 240, Page 6 of 18