Winter Park Homes for Sale

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  /35

  $149,900

  • 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. Price Reduced!! 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 condo, you're greeted by a

  

  Jason Price

  ROBERT SLACK LLC

  (321) 490-1756

  1695 Lee Rd Unit E103, Winter Park, FL 32789
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  /44

  $729,000

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  607 Dunblane Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel

  

  Khozaif Merali

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 490-4706

  607 Dunblane Dr, Winter Park, FL 32792
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  /36

  $765,000

  • 3 Beds
  • 2 Baths
  • 2,134 Sq Ft

  2418 Whitehall Cir, Winter Park, FL 32792

  MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding luxury in a modern setting and with stunning curb

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /47

  $1,050,000

  • 3 Beds
  • 2.5 Baths
  • 2,140 Sq Ft

  1610 Chestnut Ave, Winter Park, FL 32789

  Nestled in the desirable Tree Streets of Winter Park, this stunning Mid-Century Modern residence offers timeless style, thoughtful updates, and effortless indoor-outdoor living. With over 2,100 square feet of beautifully designed space, this 3-bedroom, 2.5-bath home delivers modern functionality with elegant character—just minutes from the heart of Park Avenue.Inside, you'll find an open

  

  Derek Kammerer

  THE AGENCY ORLANDO

  (321) 495-8354

  1610 Chestnut Ave, Winter Park, FL 32789
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  /100

  $8,500,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade

  

  Prescilla Vazquez

  PV LUXURY GROUP PA

  (321) 478-2671

  2661 Vía Tuscany, Winter Park, FL 32789
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  /49

  $649,900

  • 3 Beds
  • 2 Baths
  • 1,469 Sq Ft

  1926 Natalen Rd, Winter Park, FL 32792

  *** MUST SEE WINTER PARK POOL HOME ***Explore the virtual tours to fully appreciate the beauty of this completely renovated 3 bedroom/2 bath solid block pool home nestled in the highly desirable Kenilworth Shores community in Winter Park. This move-in-ready home features an open layout with vaulted ceilings and an abundance of natural light, highlighted by a large free-flowing

  Peggy Bonnewitz EXP REALTY LLC

  1926 Natalen Rd, Winter Park, FL 32792
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  /54

  $3,544,999

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /66

  $1,249,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 1,993 Sq Ft

  2525 Venetian Way, Winter Park, FL 32789

  Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake AccessThis meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace.The sleek, chef-inspired

  Kimberly Slinger KELLY PRICE & COMPANY LLC

  2525 Venetian Way, Winter Park, FL 32789
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  /37

  $950,000

  • 3 Beds
  • 3.5 Baths
  • 2,116 Sq Ft

  1251 Arlington Place, Winter Park, FL 32789

  STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

  Brad Barnett ANNE ROGERS REALTY GROUP INC

  1251 Arlington Place, Winter Park, FL 32789
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  /48

  $2,150,000

  • 5 Beds
  • 4.5 Baths
  • 3,851 Sq Ft

  1560 Woodland Ave, Winter Park, FL 32789

  You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

  Manny Alvarez LOKATION

  1560 Woodland Ave, Winter Park, FL 32789
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  /59

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
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  /28

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
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  /24

  $135,000

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

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene and convenient Orlando community. This condo boasts 3 bedrooms and 2 bathrooms thoughtfully designed with a spacious layout perfect for comfortable living. From the bright and open living area to the modern kitchen with upgraded appliances. Every detail has been tailored for

  Thomas Hicks, Sr LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /31

  $1,490,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
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  /56

  $3,150,000

  • 6 Beds
  • 5 Baths
  • 4,767 Sq Ft

  575 Palmer Ave, Winter Park, FL 32789

  Step into elevated Winter Park living with this exceptional Mediterranean-inspired estate. Built in 2020, every inch of this home was thoughtfully crafted with timeless architecture and sophisticated, high-end finishes. From the rounded stone entry feature and custom iron double doors to the soaring ceilings and designer lighting, this home instantly impresses. The spacious great room opens to a

  Joe Devlin DEVLIN INVESTORS & ASSOCIATES

  575 Palmer Ave, Winter Park, FL 32789
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  /26

  $370,000

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfect blend of privacy, style, and unbeatable location. Just one block from Winter Park Village and only a mile from Park Avenue, you’ll enjoy walkable access to some of the area’s best dining, shopping, and entertainment.Located on the first floor, this beautifully renovated 2-bed, 2-bath home features

  Brandon Geers COMPASS FLORIDA LLC

  150 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /50

  $1,349,500 Open Sat 1PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,714 Sq Ft

  1371 Lyndale Blvd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. As you enter this renovated 4-bedroom, 2.5-bathroom home within the city limits of Winter Park, you're immediately welcomed by a bright, open living and dining area anchored by a stunning wet bar, complete with sink, cabinetry, ice maker, and floating shelves. All completed with light modern porcelain tile flooring. To your right, the kitchen

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1371 Lyndale Blvd, Winter Park, FL 32789
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  $1,100,000 Open Sat 10AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 2,826 Sq Ft

  512 Clarendon Ave, Winter Park, FL 32789

  Beautifully updated 4BD/3.5BA townhome in highly sought-after Virginia Heights, just steps from Park Ave, Rollins College and zoned for Audubon K-8! This spacious 2,826 SF home features two primary suites—one on each level—ideal for guests or multi-gen living. Gorgeous hardwood like tile floors throughout, high ceilings, crown molding, and two fireplaces add timeless elegance. The chef’s kitchen

  Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  /20

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,010 Sq Ft

  1920 Woodcrest Dr Unit 15, Winter Park, FL 32792

  Gorgeous, fully renovated 2-bedroom / 2-bathroom condominium nestled in the heart of Winter Park along a beautiful and quiet tree lined street! The unit has new premium vinyl plank floors throughout. Living and dining room are open concept, perfect for entertaining! The updated kitchen features quartz counter tops, stainless appliances with new light and bright cabinetry. Bedrooms are a split

  Shirley Jones COLDWELL BANKER RESIDENTIAL RE

  1920 Woodcrest Dr Unit 15, Winter Park, FL 32792
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  $1,750,000

  • 3 Beds
  • 4 Baths
  • 2,964 Sq Ft

  1270 Arlington Place, Winter Park, FL 32789

  Modern Elegance in the Heart of Winter Park!Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this home reflects exceptional craftsmanship and elevated taste.A long paver driveway welcomes

  Brian Mitnik RE/MAX 200 REALTY

  1270 Arlington Place, Winter Park, FL 32789
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  /38

  $1,425,000

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

  2015 Summerfield Rd, Winter Park, FL 32792

  In the heart of Kenilworth Shores, one of Winter Park’s desirable neighborhoods, this completely renovated one-story residence offers a blend of modern luxury and effortless livability. Meticulously reimagined in 2024, every detail of this home has been thoughtfully curated—from the clean-lined architectural finishes to the flowing, open-concept layout that seamlessly connects indoor and outdoor

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2015 Summerfield Rd, Winter Park, FL 32792
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  /60

  $1,470,000

  • 4 Beds
  • 3.5 Baths
  • 3,349 Sq Ft

  2401 Lafayette Ave, Winter Park, FL 32789

  Seller concessions available contingent upon offer amount! Experience the charm and elegance of Winter Park living in this beautifully designed 4-bedroom, 3.5-bath home offering 3,604 square feet of thoughtfully crafted space. Built in 2014, this residence combines timeless architectural character with modern functionality, all nestled on a quiet, tree-lined street in one of Central Florida’s

  Nehad Darwish DIVINE ESTATES REALTY LLC

  2401 Lafayette Ave, Winter Park, FL 32789
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  /47

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 2,953 Sq Ft

  1420 Palmer Ave, Winter Park, FL 32789

  Luxurious Retreat in the Heart of Winter Park’s Premier Neighborhood – Minutes from Park Ave!Discover timeless elegance in this stunning 4-bedroom, 3.5-bathroom home offering 2,953 square feet of thoughtfully designed living space. Nestled on tree-lined streets in one of Winter Park’s most coveted areas, surrounded by multi-million-dollar estates and just moments from the Winter Park Chain of

  Amy Turner KELLER WILLIAMS WINTER PARK

  1420 Palmer Ave, Winter Park, FL 32789
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  /48

  $1,499,000

  • 5 Beds
  • 4 Baths
  • 4,181 Sq Ft

  1327 Bridgeport Dr, Winter Park, FL 32789

  This 5 bedroom, 4 full bathroom one story refreshed ranch estate boasts nearly 4,200 sq ft and features 3 fireplaces, double primary suites, and sprawls out on an oversized .36 acre lot, overlooking an open air salt water & solar heated pool. Updates & upgrades include: full roof replacement with transferable warranty (2023), new windows with transferable warranty (2023), 4 newer ACs (2 are 2023

  Jennifer Christ RE/MAX TOWN & COUNTRY REALTY

  1327 Bridgeport Dr, Winter Park, FL 32789
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  /55

  $1,514,950

  • 4 Beds
  • 4 Baths
  • 3,474 Sq Ft

  952 Moss Ln, Winter Park, FL 32789

  Discover the allure of 952 Moss Ln, a stunning residence in the heart of Winter Park that seamlessly blends elegance and modern comfort. This captivating 4-bedroom, 3-bathroom home exudes warmth and sophistication, creating an inviting haven for discerning buyers. Sunlight floods every room, highlighting the home’s refined details and creating a luminous, welcoming atmosphere. Step inside to find

  Terry Connors THE SHOP REAL ESTATE CO.

  952 Moss Ln, Winter Park, FL 32789
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  /59

  $1,495,000

  • 3 Beds
  • 3 Baths
  • 2,351 Sq Ft

  1741 Palmer Ave, Winter Park, FL 32789

  Welcome home to this one-of-a-kind, single-story Tuscan-style retreat nestled on an oversized lot in the heart of highly coveted Winter Park. From the moment you arrive, the round circular paver driveway and beautifully landscaped exterior set the tone for the warmth and elegance that awaits inside. Enter through custom wrought-iron gates into a private covered and screened in courtyard lanai,

  Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1741 Palmer Ave, Winter Park, FL 32789
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  /28

  $244,999

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792

  Charming 2-Story Condo in the Heart of Winter ParkLocated in the highly sought-after city of Winter Park, this beautifully maintained 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, convenience, and community living. Along with a dedicated covered carport parking space. Just minutes from Park Avenue, top-rated shopping, and dining destinations, this home puts you at the

  Jessica Geer A+ REALTY PROFESSIONALS, INC

  200 Saint Andrews Blvd Unit 3002, Winter Park, FL 32792
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  /33

  $241,000

  • 2 Beds
  • 1 Bath
  • 710 Sq Ft

  151 N Orlando Ave Unit 204, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restrictions! Welcome to the Lake Killarney Condo Community! This two-bedroom, one-bathroom condo features sold surface countertops in the kitchen, complete bathroom renovation with updated fixtures, newer floors in some rooms, washer/dryer hookups, newer kitchen appliances, and a complete interior fresh coat of

  Eddie Cooper MAINFRAME REAL ESTATE

  151 N Orlando Ave Unit 204, Winter Park, FL 32789
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  $1,575,000

  • 5 Beds
  • 8 Baths
  • 3,626 Sq Ft

  1742 Barcelona Way, Winter Park, FL 32789

  OPPORTUNITY AWAITS – PURE POTENTIAL IN WINTER PARK’S SEVILLA NEIGHBORHOOD! Rare, Tudor-style estate sits on an oversized 0.44 acre lot (19,217 SF) at the end of a quiet cul-de-sac and offers elevated views of Lake Sue. Originally built in the 1970’s, this well-built, concrete block home, offers a very spacious interior layout with 5-bedrooms, 5 full baths, 2 half baths, formal living & dining

  Kelly Price KELLY PRICE & COMPANY LLC

  1742 Barcelona Way, Winter Park, FL 32789
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  /40

  $1,595,000

  • 4 Beds
  • 3.5 Baths
  • 3,204 Sq Ft

  1831 Mizell Ave, Winter Park, FL 32789

  Stunning contemporary home in Winter Park is close to Park Avenue and all of the wonderful restaurants, shops and the historic farmer's market. This luxurious home exudes a crisp, pristine setting with modern living spaces and a well-designed, stylish living environment. Off the foyer entry is a home office or bonus room as well as a powder bath. The beautiful dining room is open to an elegant

  Bryan DeCorso EXP REALTY LLC

  1831 Mizell Ave, Winter Park, FL 32789
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  $1,325,000

  • 5 Beds
  • 4 Baths
  • 3,068 Sq Ft

  2105 Fosgate Dr, Winter Park, FL 32789

  This home is the perfect blend of resort luxury and farmhouse charm, with high-end finishes and features that cater to both relaxation and entertaining. From the resort-style backyard with a magnificent Saltwater Pool, lovely green space around the koi pond to the HGTV-worthy Interior with an entertainer’s dream kitchen, this has it all. The spacious split-bedroom floor plan, luxurious primary

  Eileen Winfrey LPT REALTY, LLC

  2105 Fosgate Dr, Winter Park, FL 32789
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  /16

  $1,470,000

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft

  1644 Hibiscus Ave, Winter Park, FL 32789

  Charming, Well-Maintained Home on a Prime Lot in Winter Park’s Coveted Tree StreetsDon’t miss this rare opportunity to own a beautifully landscaped and meticulously maintained property on one of the most desirable streets in Winter Park. Situated on one of the largest lots in the sought-after Tree Streets, this home is perfect for a buyer or builder ready to create something truly special

  Harry Pool, III COLDWELL BANKER RESIDENTIAL RE

  1644 Hibiscus Ave, Winter Park, FL 32789
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  $249,900

  • 2 Beds
  • 2 Baths
  • 1,015 Sq Ft

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792

  Excellent opportunity in a prime location in Central Florida. This two-bedroom, two-full-bath corner unit is in the Four Seasons Condominiums of Winter Park, just steps from the Cady Way Trail, Showalter Field, Ward Park, the YMCA, medical centers, and shopping. Park Avenue and museums are just minutes away. Four Seasons Condominiums is a 20-acre community located within the Winter Park city

  Lucy Gonzalez Zabala CHARLES RUTENBERG REALTY ORLANDO

  200 Saint Andrews Blvd Unit 2306, Winter Park, FL 32792
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  /45

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 2,388 Sq Ft

  1341 Lyndale Blvd, Winter Park, FL 32789

  Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience.Inside, enjoy 10’ ceilings, rich wood,

  Brandon Geers COMPASS FLORIDA LLC

  1341 Lyndale Blvd, Winter Park, FL 32789
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  /49

  $220,000

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 208, Winter Park, FL 32789

  This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfort and convenience. Featuring tile and luxury vinyl plank flooring throughout, this home provides durability and style for modern living. The HVAC was replaced in 2020 and water is included in the monthly COA fee. Located in a picturesque community ON THE SHORES OF A SKI LAKE, residents will enjoy access to

  Debbie Fussell KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 208, Winter Park, FL 32789
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  /38

  $245,000

  • 1 Bed
  • 1 Bath
  • 787 Sq Ft

  700 Melrose Ave Unit L23, Winter Park, FL 32789

  Welcome to your serene retreat in the highly desirable Winter Park Gardens community. This beautifully renovated second-floor 1-bedroom, 1-bathroom condo offers an exceptional living experience with modern upgrades and a prime location less than a mile from Park Avenue and Orlando Avenue. Step inside to discover luxury vinyl flooring throughout the entry, living space, and kitchen, complemented

  Elena Sanchez BALDWIN PARK REALTY LLC

  700 Melrose Ave Unit L23, Winter Park, FL 32789
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  /49

  $1,275,000

  • 6 Beds
  • 4 Baths
  • 2,284 Sq Ft

  726 N Pennsylvania Ave, Winter Park, FL 32789

  Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms and 2 bathrooms, designed with a modern, elegant aesthetic. With dual living areas, kitchens, and

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  726 N Pennsylvania Ave, Winter Park, FL 32789
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  /22

  $225,000

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792

  Winter Park gem! Tastefully updated 2-bedroom, 2-bathroom corner condominium with a spacious patio is your rare chance ! This one-of-a kind residence boasts high quality enhancements such as plantation shutters, built-in closets, smart canned lighting in the living room, dining room, kitchen, and hallway, along with a smart fan with a light kit in the main bedroom, a Nest

  Irina Paul FUTURE HOME REALTY INC

  1913 Woodcrest Dr Unit B, Winter Park, FL 32792
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  /37

  $714,900 Open Fri 5PM - 6:30PM

  • 3 Beds
  • 2 Baths
  • 1,704 Sq Ft

  1640 Cypress Point Ln, Winter Park, FL 32792

  Welcome to 1640 Cypress Point – a home like no other in Winter Park. This beautifully maintained 3-bedroom, 2-bathroom home offers 1,704 sq. ft. overlooking a serene spring-fed pond and the Winter Park Pines Golf Course. Nestled on a quiet street with a cul-de-sac, this property combines privacy, natural beauty, and convenience in one exceptional location. As you walk up to the front door, you’ll

  Amy Turner KELLER WILLIAMS WINTER PARK

  1640 Cypress Point Ln, Winter Park, FL 32792
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  /39

  $399,900 Open Sat 11AM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,500 Sq Ft

  2012 Dorris Dr, Orlando, FL 32807

  Dream Home Alert!! Spectacular Modern/Luxury Fully Renovated Custom Home From Roof to Floor; Located in The Heart of Orlando. This Breathtaking Home Is Featuring 3 Large Bedrooms, 2 Bathrooms, A Private Entry Office/Den; A Gourmet Kitchen Built With Elegance and Luxury, White Wood Cabinets, High Quality Quartz Countertop, A Kitchen Island, Backsplash, Italian Tile, The Top-of-The-Line Stainless

  Miguel Guedez VENCORP REAL ESTATE

  2012 Dorris Dr, Orlando, FL 32807

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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 very car-dependent and somewhat bikeable with some transit options. Winter Park is a suburban neighborhood. Winter Park has 23 parks for recreational activities. It is somewhat dense in population with 6.8 people per acre and a median age of 41. The average household income is $111,076 which is above the national average. College graduates make up 54.4% of residents. A majority of residents in Winter Park are home owners, with 47.8% of residents renting and 52.2% 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 less safe than the average neighborhood in the United States. It received a crime score of 5 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 $709,000. If you put a 20% down payment of $141,800 and had a 30-year fixed mortgage with an interest rate of 6.75%, your estimated principal and interest payment would be $3,680 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $158K a year to afford the median home price in Winter Park. The average household income in Winter Park is $111K.

What are the best public schools in Winter Park?

The best public schools that serve Winter Park are:

• Winter Park High has an A+ Niche grade, a student teacher ratio of 22:1 and an average review score of 3.9.
• Dommerich Elementary School has an A Niche grade, a student teacher ratio of 16:1 and an average review score of 5.0.
• Baldwin Park Elementary has an A- Niche grade and a student teacher ratio of 15:1.

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 8:1 and an average review score of 4.5.
• 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, Colonialtown North and Audubon Park.

Are home prices dropping in Winter Park?

Yes, home prices in Winter Park are down 3% in the last 12 months.

Home Trends in Winter Park, FL

On average, homes in Winter Park, FL sell after 67 days on the market compared to the national average of 51 days. The median sale price for homes in Winter Park, FL over the last 12 months is $665,000, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$665,000

Median Single Family Sale Price

$899,000

Median Townhouse Sale Price

$772,500

Median 2 Bedroom Sale Price

$230,000

Median 1 Bedroom Sale Price

$159,950

Average Price Per Sq Ft

$429

Number of Homes for Sale

213

Last 12 months Home Sales

628

Months of Supply

4.10

Median List Price

$709,000

Median Change From 1st List Price

6%

Median Home Sale Price YoY Change

-2%