Winter Park Houses for Sale

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  /50

  $469,900

  • 3 Beds
  • 3 Baths
  • 1,880 Sq Ft

  2835 Bongart Rd, Winter Park, FL 32792

  Seller is Motivated and open to incentives, must sell NOW! - Welcome to your spectacular pool home in Winter Park Estates. This beautifully renovated 3-bedroom, 3-bath residence features all the modern upgrades you've been searching for inside and out! Enjoy peace of mind with a new A/C unit (warranty included) and resurfaced pool complete with a new pump—perfect for Florida living. The backyard

  

  Claudia Jenkins

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 450-7314

  2835 Bongart Rd, Winter Park, FL 32792
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  Explore Winter Park

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  /42

  $765,000

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

  2418 Whitehall Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. 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

  

  Alice Anne Jackson

  CORCORAN PREMIER REALTY

  (321) 599-7240

  2418 Whitehall Cir, Winter Park, FL 32792
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  /38

  $875,000

  • 4 Beds
  • 4 Baths
  • 2,759 Sq Ft

  730 S Ranger Blvd, Winter Park, FL 32792

  Stunning, one of kind, 4/4 Winter Park pool home loaded with upgrades! ROOF, AC & WATER HEATER (2020), NEW FLOORING, KITCHEN & BATHS (2025), QUARTZ COUNTER TOPS (2025) FRESH INTERIOR PAINT (2025) & EXTERIOR (2023). Enjoy NEW DRIVEWAY PAVERS, FRONT YARD IRRIGATION (2025), REPLACEMENT WINDOWS & FRENCH DOORS (2016). Largest old school POOL in the neighborhood (20x40) RESURFACED (2016) with NEW PUMP

  David Knight EXP REALTY LLC

  730 S Ranger Blvd, Winter Park, FL 32792
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  /72

  $950,000

  • 3 Beds
  • 3 Baths
  • 2,456 Sq Ft

  915 Garden Dr, Winter Park, FL 32789

  Step into this beautifully maintained Mid-Century Modern home, nestled in the prestigious Winter Park community and just a short three-minute stroll to the serene beauty of Mead Botanical Garden. A true raised ranch design, this home radiates warmth and character from the moment you arrive, featuring an expansive covered front patio that welcomes you inside.Inside, you’ll be greeted by

  Cassie Lamoureux KELLER WILLIAMS CLASSIC

  915 Garden Dr, Winter Park, FL 32789
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  /29

  $405,000 Open Sat 1:30PM - 3:30PM

  • 3 Beds
  • 2 Baths
  • 1,354 Sq Ft

  259 Blossom Ln, Winter Park, FL 32789

  Charming Winter Park Block Home with Deeded Access to Lake Killarney – Solid, Updated Systems & Priced for Your Personal Touch!Welcome to this well-built 3-bedroom, 2-bath cement block home in one of Winter Park’s most desirable and established neighborhoods. . . . . . Built in 1954 and lovingly cared by the same owner for almost 40 years, this home offers strong bones, a functional layout,

  Sherrie Wysong LEGACY REALTY & BROKERS LLC

  259 Blossom Ln, Winter Park, FL 32789
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  /44

  $3,499,999

  • 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

  Kelly Price KELLY PRICE & COMPANY LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /77

  $2,900,000

  • 4 Beds
  • 7 Baths
  • 5,416 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

  Terry Yonker BUCKEYE REALTY LLC

  1401 Green Cove Rd, 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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  /56

  $1,195,000

  • 4 Beds
  • 3.5 Baths
  • 2,565 Sq Ft

  215 Salvador Square, Winter Park, FL 32789

  Welcome home to this lovely 4-bedroom, 3.5-bath pool home in the prestigious Sevilla neighborhood of Winter Park! Tucked off a charming brick-lined street just 1⁄4 mile from Park Avenue, this .40-acre property offers both privacy and convenience to your Winter Park lifestyle.Inside, you’ll find timeless details such as marble and parquet flooring, crown molding, plantation shutters

  Carrie Bantel PREMIER SOTHEBY'S INTL. REALTY

  215 Salvador Square, Winter Park, FL 32789
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  /60

  $2,369,000

  • 5 Beds
  • 4 Baths
  • 4,328 Sq Ft

  715 Via Bella, Winter Park, FL 32789

  Tucked away on a quiet cul-de-sac lined with multi-million-dollar estates, this Winter Park residence offers an enviable blend of privacy, lifestyle, and location. Less than a mile from Park Avenue, the Winter Park 9 Golf Course, and the Racquet Club, this address puts you at the center of the city’s most coveted amenities. A deeded greenbelt easement to Lake Osceola—just 100 yards from the front

  Adam Roark COMPASS FLORIDA LLC

  715 Via Bella, Winter Park, FL 32789
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  /2

  $1,690,000

  • 2 Beds
  • 1 Bath
  • 1,559 Sq Ft

  141 W Lake Sue Ave, Winter Park, FL 32789

  AMAZING Winter Park Opportunity! Nestled in one of the most desirable locations, 141 W Lake Sue Avenue offers a VERY HARD to find 1⁄2 acre lot—the epitome of prime real estate. The true value lies in the land, making this a rare chance for builders or buyers to create their dream Winter Park residence. Surrounded by beautiful homes and tree-lined streets, this pristine lot provides the perfect

  Brian Mitnik RE/MAX 200 REALTY

  141 W Lake Sue Ave, Winter Park, FL 32789
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  /51

  $1,285,000 Open Sat 11AM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome home to this beautifully renovated 4-bedroom, 2-bathroom home nestled on a desirable corner lot in the heart of Winter Park’s Timberlane Shores community. Boasting

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /64

  $2,199,999 Open Sun 2PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,314 Sq Ft

  1752 Chestnut Ave, Winter Park, FL 32789

  Timeless Elegance Meets Modern Comfort in Sought-After Tree StreetsWelcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style.At the heart of the

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1752 Chestnut Ave, Winter Park, FL 32789
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  /50

  $2,149,000

  • 5 Beds
  • 4.5 Baths
  • 3,174 Sq Ft

  1710 Oneco Ave, Winter Park, FL 32789

  Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptional residence features high-end designer finishes and exceptional craftsmanship throughout for modern

  Rhonda Chesmore KELLY PRICE & COMPANY LLC

  1710 Oneco Ave, Winter Park, FL 32789
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  /56

  $2,999,000

  • 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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  /44

  $1,300,000

  • 3 Beds
  • 3.5 Baths
  • 3,363 Sq Ft

  800 Hamilton Place Ct, Winter Park, FL 32789

  Custom-built and beautifully maintained, this large 3-bedroom home with loft is located in prime Old Winter Park on a quiet cul-de-sac. The interior boasts 20'+ high ceilings, creating a grand and airy atmosphere throughout the main living spaces. High-end finishes include Viking stainless steel appliances, dolomite marble tile flooring, and a thoughtfully designed, functional layout ideal for

  Julian Torres, Jr EPIC REAL ESTATE ADVISORS LLC

  800 Hamilton Place Ct, Winter Park, FL 32789
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  /40

  $1,660,000

  • 4 Beds
  • 5 Baths
  • 3,478 Sq Ft

  1350 Lyndale Blvd, Winter Park, FL 32789

  THIS HOUSE CHECKS ALL OF THE BOXES!!!Situated on a quiet one-way street in Winter Park and recently renovated is this 4 bed, 3 full 2 half bath home built with style and elegance. From the 10’ ceilings to Brazilian cherry floors, a gourmet kitchen, screened pool and generous bonus room above the oversized garage with tons of storage, this home has it all. The impressive gourmet

  Carol Wittman PALMANO GROUP RE BROKERAGE LLC

  1350 Lyndale Blvd, Winter Park, FL 32789
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  /60

  $1,425,000

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

  2401 Lafayette Ave, Winter Park, FL 32789

  Seller is including a premium home warranty giving buyers peace of mind with coverage on HVAC, plumbing, appliances & more so you can move in with confidence! Professional deep cleaning will be paid for by seller before closing! 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

  Nehad Darwish DIVINE ESTATES REALTY LLC

  2401 Lafayette Ave, Winter Park, FL 32789
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  /55

  $1,474,950

  • 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

  $1,445,000

  • 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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  /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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  /58

  $1,295,000

  • 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

  $1,449,000

  • 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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  /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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  /69

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 2,841 Sq Ft

  1701 Palmer Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Charming Winter Park Pool Home – A Rare Opportunity! Nestled in the heart of Winter Park’s highly sought after 32789 zip code, this 4-bedroom, 3-bathroom pool home offers timeless charm, abundant space, and unlimited potential! Set on an expansive corner lot, this residence is just steps from Phelps Park, surrounded by tree-lined streets, and

  Jackie Swisher TRUST EQUITY GROUP LLC

  1701 Palmer Ave, Winter Park, FL 32789
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  /65

  $1,299,000 Open Sun 12PM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,014 Sq Ft

  1600 Barcelona Way, Winter Park, FL 32789

  Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning

  Laura Ascenso LPT REALTY, LLC

  1600 Barcelona Way, 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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  /50

  $1,290,000

  • 4 Beds
  • 3 Baths
  • 2,310 Sq Ft

  1400 S Pennsylvania Ave, Winter Park, FL 32789

  Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location. You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of parking flanked with lush mature landscaping. The open floor plan offers today's contemporary living

  Jack Keller JACK KELLER INC

  1400 S Pennsylvania Ave, Winter Park, FL 32789
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  /36

  $1,449,000

  • 4 Beds
  • 4 Baths
  • 3,116 Sq Ft

  1429 Chapman Cir, Winter Park, FL 32789

  Exceptional Phil Kean-designed contemporary masterpiece in Winter Park's prestigious Windsong community. This sophisticated 4-bedroom, 4-bathroom residence seamlessly blends modern luxury with practical living across two thoughtfully planned levels.The striking exterior features geometric lines, stacked stone accents, and dramatic double entry doors, setting the tone for the remarkable

  Greg Martinez CORCORAN PREMIER REALTY

  1429 Chapman Cir, Winter Park, FL 32789
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  /59

  $1,649,900 New Construction

  • 4 Beds
  • 4 Baths
  • 2,743 Sq Ft

  1780 Mizell Ave, Winter Park, FL 32789

  Discover modern luxury living in this newly constructed, architect-designed residence by Gary Hancock, ideally located in the heart of Winter Park. Offering nearly 2,800 square feet of thoughtfully planned living space, this four-bedroom, four-bath home combines timeless architecture with premium finishes for an elevated lifestyle experience.Step inside to 10-foot ceilings on both levels,

  Megan Byers PREMIER SOTHEBY'S INTL. REALTY

  1780 Mizell Ave, Winter Park, FL 32789
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  /16

  $1,201,000 New Construction

  • 5 Beds
  • 3 Baths
  • 2,618 Sq Ft

  1807 Magnolia Ave, Winter Park, FL 32789

  Under Construction. Scheduled to start in September 2025 with estimated completion in March 2026. New construction in the City of Winter Park! This home has been thoughtfully designed, but there is still time to make personalized finish selections if desired. This deep 56 x 157 lot is Winter Park's best kept secret, located in a quiet pocket of 32789. The huge backyard will be ~55-ft deep once

  Kristen Hamilton LOMBARDO TEAM REAL ESTATE LLC

  1807 Magnolia Ave, Winter Park, FL 32789
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  /24

  $1,644,900 New Construction

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

  607 Ellen Dr, Winter Park, FL 32789

  Step into refined living at 607 Ellen Drive, a brand-new two-story modern minimalist home by award-winning Lazarus Winter Park. With 2,812 square feet, this stunning residence offers four bedrooms, a dedicated office, and a luxurious first-floor primary suite. Light oak wide-plank floors and glass stair railings create a sleek, airy aesthetic. Expansive sliding glass doors fully open to a private

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  607 Ellen Dr, Winter Park, FL 32789
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  /36

  $1,100,000

  • 3 Beds
  • 2.5 Baths
  • 2,495 Sq Ft

  930 S Kentucky Ave, Winter Park, FL 32789

  Welcome home! Nestled in the heart of Winter Park this 3-bedroom, 2.5 bathroom residence offers a perfect blend of convenience, energy efficiency, and refined comfort. From the moment you enter, you'll be captivated by high ceilings and crown molding for a spacious and refined feel. The kitchen is a chef's dream featuring granite countertops, stainless steel appliances, a gas range and upgraded

  Debi Callahan ADAMS, CAMERON & CO., REALTORS

  930 S Kentucky Ave, Winter Park, FL 32789
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  /22

  $649,000 Open Sat 11AM - 1PM

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

  720 W Webster Ave, Winter Park, FL 32789

  Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural experiences.Inside, rich wood flooring, natural light, and thoughtful touches create a warm and

  Brian Hyser THE AGENCY ORLANDO

  720 W Webster Ave, Winter Park, FL 32789
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  /5

  $559,500

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft

  407 S Lakemont Ave, Winter Park, FL 32792

  *** PREMIER LAND OPPORTUNITY on Winter Park, FL*** Don't miss your chance to build your custom home in this highly desirable area, surrounded by multi-million-dollar homes. Value is in the land. Take advantage of an exceptional opportunity to own a prime piece of land in the highly desirable area of Winter Park, FL. Winter Park residents enjoy various amenities, including access to top-notch

  Ricardo De Castro Carvalho LA ROSA REALTY CENTRAL FLORIDA

  407 S Lakemont Ave, Winter Park, FL 32792
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  /15

  $795,000

  • 4 Beds
  • 3.5 Baths
  • 2,640 Sq Ft

  1740 Anzle Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. PROPERTY AS-IS - DEMO AND NEW-BUILD PLANS READY Nestled in the heart of Winter Park’s coveted 32789 ZIP code, this stunning new possibility offers the epitome of luxury living in one of Central Florida’s most coveted neighborhoods. Spanning a generous 6,598 sq ft lot, this modern two-story masterpiece boasts an approximate 2,640 sq ft of

  Felipe Robayo GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  /43

  $549,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  2308 Mulbry Dr, Winter Park, FL 32789

  CHARMING 3 BEDROOM, 2 BATH IN THE HEART OF WINTER PARK! This home is located in a highly desirable neighborhood, ideally positioned between Baldwin Park, Audubon Park, Mills 50, and Park Avenue. Just steps from Blue Jacket Park, you’ll enjoy morning walks, weekend picnics, and easy access to the shopping, dining, and entertainment that make Winter Park so special. With so much potential, you can

  Daniel Sposato BALDWIN PARK REALTY LLC

  2308 Mulbry Dr, Winter Park, FL 32789
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  /52

  $725,000 Open Sat 12PM - 2PM

  • 4 Beds
  • 2 Baths
  • 2,372 Sq Ft

  1729 Golfside Dr, Winter Park, FL 32792

  Golfside living, beautifully reimagined. This 4-bedroom, 2-bath retreat in Winter Park Pines marries timeless charm with thoughtful modern updates — from the warmth of a wood-burning fireplace to a dream kitchen finished in quartz, honeycomb tile, and designer lighting. A versatile dining or flex space invites effortless entertaining or the perfect work-from-home setting.The primary suite

  Rebecca Bininger Junod KELLER WILLIAMS WINTER PARK

  1729 Golfside Dr, Winter Park, FL 32792
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  /24

  $399,000

  • 2 Beds
  • 1 Bath
  • 1,222 Sq Ft

  1001 Early Ave, Winter Park, FL 32789

  Welcome to 1001 Early Ave—a beautifully updated 2-bedroom, 1-bath home that perfectly balances timeless character with contemporary style. Nestled on a spacious 7,405 sq ft lot, this 1,222 sq ft gem invites you in with refinished parquet floors, decorator tile, and abundant natural light. The expanded kitchen is a showstopper, featuring stainless steel appliances, granite countertops, a wine

  John Neusaenger COLDWELL BANKER REALTY

  1001 Early Ave, Winter Park, FL 32789
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  /52

  $565,000

  • 3 Beds
  • 2 Baths
  • 2,119 Sq Ft

  7325 Tiffany Dr, Orlando, FL 32807

  Rare Opportunity – Secluded 1.6-Acre Property with Endless Possibilities!Bring all reasonable offers! This one-of-a-kind single-family home sits on 1.6 acres of land, which extends beyond the chain-link fence in the backyard, offering privacy, space, and freedom with NO HOA!Recent upgrades include:New Roof – July 2025 and Fresh new privacy bushes and drip irrigation system– August

  Dania Valentine KEY REAL ESTATE & PROPERTY MANAGEMENT LLC

  7325 Tiffany 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

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 52 days. The median sale price for homes in Winter Park, FL over the last 12 months is $675,000, up 1% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$675,000

Median Single Family Sale Price

$896,000

Median Townhouse Sale Price

$790,000

Median 2 Bedroom Sale Price

$240,500

Median 1 Bedroom Sale Price

$167,700

Average Price Per Sq Ft

$439

Number of Homes for Sale

200

Last 12 months Home Sales

636

Months of Supply

3.80

Median List Price

$725,000

Median Change From 1st List Price

6%

Median Home Sale Price YoY Change

1%