Winter Park Homes for Sale

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  /65

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
• Explore Winter Park

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  /23

  $139,990

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Waterfall Cove, where urban convenience meets tranquil living. This charming 2-bedroom, 1-bathroom condo offers a cozy retreat with all the perks of modern living. Located in the heart of Orlando, this condo is perfect for those looking for a blend of city life and natural beauty. As you step into the

  

  Jason Price

  RE/MAX SELECT GROUP

  (321) 895-9463

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /19

  $179,700

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

  Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  (321) 334-3379

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
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  /41

  $245,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 229, Winter Park, FL 32789

  DRAMATIC PRICE ADJUSTMENT! Million Dollar Lakefront View of Lake Killarney from Private Balcony and multiple Rooms in the Unit and View of Courtyard with it's Gracious Old Tree and Meandering Walkways from second Private Balcony. Once in a lifetime opportunity to own this meticulously maintained and updated Mid-Century Modern Character that says "Home" when you walk through the Door! Kitchen has

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 252-5096

  2500 Lee Rd Unit 229, Winter Park, FL 32789
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  /41

  $525,000

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft

  1036 Aragon Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

  

  Tim Veigle

  WATSON REALTY CORP

  (321) 516-0689

  1036 Aragon Ave, Winter Park, FL 32789
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  /22

  $262,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
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  /21

  $264,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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  /31

  $740,000

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  Build your custom Winter Park home on one of the last available lots in this coveted 32789 corridor. Located at 841 W Swoope Ave, this 9,752 SF R-2 zoned parcel sits on W Swoope Avenue between Park Avenue and Orlando Avenue — walking distance to Winter Park Village, top-rated Winter Park schools, and the newly revitalized Park Avenue district. The existing shell structure is demo-ready, clearing

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
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  /43

  $550,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends modern updates with timeless character

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
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  /21

  $255,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  REDUCED! Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard and Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has Cabinets matching those in Kitchen and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 449-7958

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
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  /40

  $2,650,000

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  1130 Park North Place, Winter Park, FL 32789

  Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
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  /5

  $1,825,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,655 Sq Ft

  2305 Coldstream Dr, Winter Park, FL 32792

  Under Construction. A rare opportunity to own brand-new construction in desirable Brookshire Heights, this thoughtfully designed residence blends timeless finishes with modern functionality. Featuring 5 bedrooms, a dedicated office, and a spacious bonus room, the floor plan is both highly livable and exceptionally functional—ideal for everyday living and entertaining alike. All bedrooms are

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 490-4786

  2305 Coldstream Dr, Winter Park, FL 32792
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  /78

  $1,399,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
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  /34

  $574,999

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated, move-in-ready home located in the highly desired Winter Park Pines community. Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette that feels clean and inviting. The kitchen has been thoughtfully updated with shaker-style cabinetry, sleek countertops, stainless steel appliances, and

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
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  /17

  $499,990

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
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  /66

  $2,395,000

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
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  /94

  $4,195,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,665 Sq Ft

  2020 Via Tuscany, Winter Park, FL 32789

  PRESTIGIOUS VIA TUSCANY NEW CONSTRUCTION. If location was a lottery ticket, you just hit the jackpot!!! Welcome to a masterpiece of modern elegance in the heart of the Winter Park Vias. Crafted by the renowned Element Home Builders, this stunning 4,665 sq. ft. estate offers an unparalleled blend of sophistication and comfort. The expansive open-concept floor plan features 5 generous bedrooms, 4.5

  Mauro Costa CORCORAN PREMIER REALTY

  2020 Via Tuscany, Winter Park, FL 32789
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  /51

  $2,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  541 W Canton Ave, Winter Park, FL 32789
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  /54

  $1,978,000

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
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  /31

  $267,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 8D, Winter Park, FL 32789

  Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida

  Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1500 Gay Rd Unit 8D, Winter Park, FL 32789
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  /5

  $1,925,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,618 Sq Ft

  906 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792
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  /29

  $1,925,000

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /3

  $1,950,000 New Construction

  • 4 Beds
  • 4 Baths
  • 2,810 Sq Ft

  2501 Lafayette Ave, Winter Park, FL 32789

  Under Construction. Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom pivot front door into the foyer leading to your main living area featuring sliding glass walls for indoor-outdoor living.

  Tab Bish LLC REAL BROKER, LLC

  2501 Lafayette Ave, Winter Park, FL 32789
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  /53

  $2,265,000

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
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  /75

  $2,950,000

  • 4 Beds
  • 4.5 Baths
  • 4,129 Sq Ft

  151 Oakwood Way, Winter Park, FL 32789

  Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

  Matthew Burks CORCORAN PREMIER REALTY

  151 Oakwood Way, Winter Park, FL 32789
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  /50

  $1,375,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 4 Baths
  • 3,024 Sq Ft

  2015 Summerfield Rd, Winter Park, FL 32792

  Experience refined Winter Park living in Kenilworth Shores, a highly sought after neighborhood near Baldwin Park, Lake Baldwin trails, and the dining and boutiques of Park Avenue. This location places you close to Rollins College, Winter Park High, and the cultural center of Winter Park FL. Inside, natural light moves through open living spaces finished with wide porcelain tile floors. The

  Christina Fata REAL BROKER, LLC

  2015 Summerfield Rd, Winter Park, FL 32792
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  /46

  $1,695,000 Open Sat 1PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  629 Country Club Dr, Winter Park, FL 32789

  Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home with natural light and offer water views

  Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
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  /46

  $1,899,500

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
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  /57

  $1,870,000

  • 5 Beds
  • 4.5 Baths
  • 4,363 Sq Ft

  1177 Kenwood Ave, Winter Park, FL 32789

  Welcome to 1177 Kenwood Ave, a home that blends warmth, comfort, and thoughtful design. The inviting living room features a cozy fireplace, creating the perfect space to relax on cooler evenings. The kitchen is designed with both style and function in mind, stainless steel appliances and a center island ideal for meal preparation and gathering. The spacious primary suite serves as a retreat,

  Karen Albright OPENDOOR BROKERAGE LLC

  1177 Kenwood Ave, Winter Park, FL 32789
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  /57

  $1,899,900

  • 4 Beds
  • 3 Baths
  • 2,842 Sq Ft

  1521 Chestnut Ave, Winter Park, FL 32789

  Modern Luxury in the Heart of Winter Park! Welcome to this stunning modern residence, thoughtfully constructed in 2023 by the original owner/builder, located in one of Winter Park’s most sought-after neighborhoods. Designed with sleek sophistication and functional elegance, this fabulous home offers 4 bedrooms, 3 full baths, and a flexible layout perfect for today’s lifestyle. The open-concept

  Sue Silberbusch COMPASS FLORIDA LLC

  1521 Chestnut Ave, Winter Park, FL 32789
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  /50

  $1,475,000

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1751 Goodrich Ave, Winter Park, FL 32789

  Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

  Stephanie Baldner EXP REALTY LLC

  1751 Goodrich Ave, Winter Park, FL 32789
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  /89

  $1,799,999

  • 6 Beds
  • 4 Baths
  • 3,853 Sq Ft

  1451 Lyndale Blvd, Winter Park, FL 32789

  Listed at APPRAISED VALUE **Luxurious Winter Park Estate with Detached TWO bedroom Guest House** RENOVATED POOL HOME with NO HOA! TWO Primary Bedrooms located on the main floor! Welcome to a world of unparalleled luxury and elegance in the heart of historic Winter Park, FL. This exquisitely renovated two-story pool home, set on a sprawling corner lot, offers a rare opportunity to experience the

  Christopher Soucy REALTY ONE GROUP MVP

  1451 Lyndale Blvd, Winter Park, FL 32789
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  /34

  $1,550,000 New Construction

  • 4 Beds
  • 5 Baths
  • 2,812 Sq Ft

  607 Ellen Dr, Winter Park, FL 32789

  Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural light throughout. The open floor plan seamlessly connects living spaces, creating an ideal setting

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
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  /22

  $298,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 115, Winter Park, FL 32789

  Welcome to Lake Killarney Living ... Where Winter Park charm meets everyday convenience. Furniture negotiable, offering added flexibility for buyers or investors. Discover this beautifully appointed 2-bedroom, 1-bath condo in the highly sought-after Lake Killarney Condo Community, perfectly positioned just steps from Winter Park Village, dining, shopping, and the peaceful waters of Lake

  Chris Creegan CREEGAN GROUP

  151 N Orlando Ave Unit 115, Winter Park, FL 32789
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  /42

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 2,807 Sq Ft

  1903 N Park Ave, Winter Park, FL 32789

  Completed in 2020, this beautifully designed contemporary residence on North Park Avenue offers refined finishes and seamless indoor-outdoor living just minutes from Park Avenue’s famed shopping and restaurant district as well as the vibrant retail and dining of Winter Park Village and Mills50. Positioned on a prominent corner lot with dual access from N Park Ave and N Denning Drive, the home

  Chris Creegan CREEGAN GROUP

  1903 N Park Ave, Winter Park, FL 32789
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  /78

  $1,895,000

  • 4 Beds
  • 3.5 Baths
  • 3,470 Sq Ft

  1841 Harland Park Dr, Winter Park, FL 32789

  Price reduction. Motivated seller! Welcome home to the prestigious community of Windsong in Winter Park. Upon entering this Toll Brothers-built home, you will notice no detail has been spared. Soaring ceilings greet you as you enter the foyer with elegant lighting. This 4-bedroom, 3.5-bath home is loaded with upgrades. The office features beautiful wood and detailed, custom bookshelves, complete

  Shanon Luiz SELECTIVE REALTY GROUP LLC

  1841 Harland Park Dr, Winter Park, FL 32789
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  /20

  $695,000

  • 4 Beds
  • 3.5 Baths
  • 2,317 Sq Ft

  432 W Swoope Ave, Winter Park, FL 32789

  A short stroll to Park Avenue in 5 minutes. Beautiful townhome, move in ready. Spacious and open floor plan with 4 bedrooms and 3.5 baths.

  Thomas Bonner COLDWELL BANKER REALTY

  432 W Swoope Ave, Winter Park, FL 32789
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  /55

  $1,499,000 New Construction

  • 5 Beds
  • 4 Baths
  • 2,895 Sq Ft

  1473 Berkshire Ave, Winter Park, FL 32789

  Limited-time incentive: Seller offering a $20,000 buyer credit for qualified buyers. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue -- a newly completed residence on a peaceful, tree-lined street. This two-story home offers 5 bedrooms, 4 bathrooms, and nearly 2,900 sq ft of living space. Features include 10-ft ceilings, 8-ft solid-core doors,

  Crystal Canina Golden Group Realty LLC

  1473 Berkshire Ave, Winter Park, FL 32789
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  /7

  $1,390,000 Open Sat 12AM - 3PM

  • 4 Beds
  • 4.5 Baths
  • 3,253 Sq Ft

  501 Lakeview Ave, Winter Park, FL 32789

  Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 1⁄2 baths, including a full en-suite guest retreat on the main level. Three additional bedrooms share the upper floor with a bright loft that easily flexes as a

  Marie Ledbetter COLDWELL BANKER REALTY

  501 Lakeview Ave, Winter Park, FL 32789
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  /61

  $1,795,000

  • 5 Beds
  • 3.5 Baths
  • 3,304 Sq Ft

  2501 Winter Park Rd, Winter Park, FL 32789

  A masterfully crafted custom residence in the heart of Winter Park, this 2014 Barefoot Brothers home blends timeless architecture with modern functionality just moments from Park Avenue and the Audubon Park Garden District. Designed for both refined entertaining and active everyday living, this 5-bedroom + office home offers a flexible, family-focused floor plan plus an expansive second floor

  Jill Healey KELLER WILLIAMS WINTER PARK

  2501 Winter Park Rd, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 6

Why Live in Winter Park

Winter Park, a neighborhood rich in history and charm, offers a glimpse into “Old Florida” with its hanging Spanish moss and lakeside views. Originally a resort community for northern business magnates in the 19th century, Winter Park features a mix of architectural styles, from ranchers and midcentury modern to Victorian and Spanish designs. Several homes and districts, including the Hannibal Square District, are listed on the National Register of Historic Places. The Hannibal Square Heritage Center honors the historic African American community with exhibitions and educational programs. The neighborhood is adorned with lush greenery and tranquil lakes, accessible through parks like Mead Botanical Garden, which has walking trails, an amphitheater, and a butterfly garden. Central Park, located in the heart of the shopping district, hosts year-round events and the annual Winter Park Sidewalk Art Festival. The Winter Park community center provides various programs and facilities, including a fitness center and community pool. Daily needs are met by grocery stores like Whole Foods and Trader Joe’s, while niche retailers and dining options, such as Hillstone Restaurant and Bosphorous Turkish Cuisine, are plentiful. Cultural institutions like Casa Feliz and the Charles Hosmer Morse Museum of Art add to the neighborhood's artistic appeal. Winter Park is safer than the national average and offers convenient access to major roadways like Interstate 4 and state Route 50.

Learn more about living in Winter Park

Frequently Asked Questions

Is Winter Park a good place to live?

Winter Park is a good place to live, receiving 4.4 stars from its residents. Winter Park is considered somewhat walkable and bikeable with minimal transit options. Winter Park is a suburban neighborhood with a crime score of 4, on par with the average neighborhood in the U.S. Winter Park has 24 parks for recreational activities. It is somewhat dense in population with 8.2 people per acre and a median age of 42. The average household income is $119,107 which is above the national average. College graduates make up 53.4% of residents. A majority of residents in Winter Park are home owners, with 48.1% of residents renting and 51.9% of residents owning their home. A local real estate agent serving Winter Park can help you decide if this neighborhood is the right one for you. Learn more on our Winter Park neighborhood guide.

Is Winter Park, FL a safe neighborhood?

Winter Park, FL is a safe neighborhood and is on par with the average neighborhood in the United States. It received a crime score of 4 out of 10.

How much do you need to make to afford a house in Winter Park?

The median home price in Winter Park is $700,000. If you put a 20% down payment of $140,000 and had a 30-year fixed mortgage with an interest rate of 6.38%, your estimated principal and interest payment would be $3,500 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $150K a year to afford the median home price in Winter Park. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Winter Park is $119K.

What are the best public schools in Winter Park?

The best public schools that serve Winter Park are:

• Dommerich Elementary School has an A Niche grade, a student teacher ratio of 16:1 and an average review score of 4.6.
• Winter Park High has an A Niche grade, a student teacher ratio of 21:1 and an average review score of 3.9.
• Baldwin Park Elementary has an A- Niche grade and a student teacher ratio of 16:1.

What are the best private schools in Winter Park?

The best private schools that serve Winter Park are:

• Park Maitland School has an A+ Niche grade, a student teacher ratio of 11:1 and an average review score of 4.6.
• Trinity Preparatory School has an A+ Niche grade, a student teacher ratio of 11:1 and an average review score of 4.3.
• St. Charles Borromeo Catholic School has an A Niche grade, a student teacher ratio of 14:1 and an average review score of 4.8.

What are the most popular zip codes in Winter Park, Winter Park, FL?

The most popular zip codes in Winter Park, Winter Park, FL include 32789, 32792, 32814, 32803 and 32751.

What are the most popular neighborhoods near Winter Park, Winter Park, FL?

The most popular neighborhoods near Winter Park, Winter Park, FL are Baldwin Park, Orwin Manor, Lake Howell, Audubon Park and Colonialtown North.

Are home prices dropping in Winter Park?

Yes, home prices in Winter Park are down 1% in the last 12 months.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 68 days on the market compared to the national average of 55 days. The median sale price for homes in Winter Park, FL over the last 12 months is $633,550, down 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$633,550

Median Single Family Sale Price

$849,000

Median Townhouse Sale Price

$770,000

Median 2 Bedroom Sale Price

$242,000

Median 1 Bedroom Sale Price

$165,500

Average Price Per Sq Ft

$440

Number of Homes for Sale

209

Last 12 months Home Sales

660

Months of Supply

3.80

Median List Price

$700,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

-4%