Winter Park Homes for Sale

• 

  

  

  /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) 324-0916

  1695 Lee Rd Unit E103, Winter Park, FL 32789
• Explore Winter Park

• 

  

  

  /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
• 

  

  

  /23

  $259,500

  $16K PRICE DROP

  • 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
• 

  

  

  /52

  $1,150,000

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

  1981 Blue Ridge Rd, Winter Park, FL 32789

  Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 232-3531

  1981 Blue Ridge Rd, Winter Park, FL 32789
• 

  

  

  /31

  $380,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  **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 to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 461-2860

  440 Cambridge Blvd, Winter Park, FL 32789
• 

  

  /65

  $1,100,000

  $50K PRICE DROP

  • 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. NEW PRICE! 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

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  /41

  $510,000

  $15K PRICE DROP

  • 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
• 

  

  /41

  $2,495,000

  $155K PRICE DROP

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

  1130 Park North Place, Winter Park, FL 32789

  Half-acre lot just steps from Park Avenue shopping and dining, tucked on a quiet cul-de-sac in the heart of Winter Park.This traditional two-story home offers a well-designed floorplan for both everyday living and entertaining. From the moment you enter, the home feels warm and inviting. The main level features a spacious primary suite along with connected living spaces that flow easily from

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
• 

  

  /42

  $624,000

  • 3 Beds
  • 3 Baths
  • 1,620 Sq Ft

  1822 Yorkshire Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Charming three-bedroom, three-bath one-story home features a split floor plan with two primary suites, ideal for multigenerational living or guest flexibility, in a prime Winter Park location. In the desirable Park Manor subdivision, this beautifully designed split floor plan home offers comfort and privacy, perfect for modern living. Enjoy the

  MaryAnne Branner PREMIER SOTHEBY'S INTL. REALTY

  1822 Yorkshire Dr, Winter Park, FL 32792
• 

  

  /41

  $554,900

  $25K PRICE DROP

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

  330 Elkhorn Ct, Winter Park, FL 32792

  330 Elkhorn Ct is a beautifully renovated home located in the highly desired Winter Park Pines community. Freshly updated with a 2025 electric panel, 2025 A/C system, and a 2024 roof, offering modern efficiency, peace of mind, and big-ticket upgrades already taken care of! Inside, you’ll find a bright, open layout with wide-plank flooring, recessed lighting, and a modern neutral color palette

  Neil Chetram LA ROSA REALTY CW PROPERTIES L

  330 Elkhorn Ct, Winter Park, FL 32792
• 

  

  /48

  $1,275,000

  $174K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,426 Sq Ft

  1651 Westchester Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Set on a prized corner lot in Winter Parks sought after Orwin Manor Neighborhood, 1651 Westchester Ave is a timeless classic with Cape Cod inspired architecture that has been meticulously reimagined with today’s luxury finishes while preserving its original charm. Refinished Original Pine hardwood flooring and a beautifully updated fireplace welcome

  Shawn Layton SERHANT

  1651 Westchester Ave, Winter Park, FL 32789
• 

  

  /20

  $484,990

  $15K PRICE DROP

  • 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
• 

  

  /20

  $400,000

  • 2 Beds
  • 1 Bath
  • 913 Sq Ft

  2482 Roxbury Rd, Winter Park, FL 32789

  Winter Park Charm Today — Endless Possibilities Tomorrow. Welcome to a rare find in one of Winter Park’s most sought-after neighborhoods. This cozy 2BR/1BA bungalow is full of charm and sits on a spacious quarter-acre lot, giving you room to dream big. The home itself is in great condition—bright, clean, and move-in ready.But what truly sets this property apart is the location and land. With

  Gary Cohl COLDWELL BANKER REALTY

  2482 Roxbury Rd, Winter Park, FL 32789
• 

  

  /66

  $2,295,000

  $100K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /54

  $1,949,500

  $346K PRICE DROP

  • 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
• 

  

  /10

  $1,250,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  1870 Staunton Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction,

  Vinny Lay COMPASS FLORIDA LLC

  1870 Staunton Ave, Winter Park, FL 32789
• 

  

  /5

  $1,925,000

  New Construction

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

  906 Enclave Place, Winter Park, FL 32792

  Under Construction. This modern farmhouse designed home is under construction proposed completion March 2027. 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

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792
• 

  

  /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
• 

  

  /4

  $2,050,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,813 Sq Ft

  930 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

  Matthew Burks CORCORAN PREMIER REALTY

  930 Enclave Place, Winter Park, FL 32792
• 

  

  /25

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  1881 Lake Spier Dr, Winter Park, FL 32789

  Lakefront home on over 1 acre in Winter Park with direct frontage on Lake Spier.Positioned on a private, spring-fed lake, this property presents a rare opportunity to build a brand-new luxury residence or thoughtfully renovate the existing home into a refined lakefront retreat. The expansive lot, tranquil water views, and ownership extending into the lake create a setting defined by privacy,

  Rafael Zenke Pinhao NOVA REAL ESTATE SERVICES INC

  1881 Lake Spier Dr, Winter Park, FL 32789
• 

  

  /50

  $1,425,000

  $50K PRICE DROP

  • 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
• 

  

  /25

  $1,249,900

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,936 Sq Ft

  Winter Park, FL 32789

  Pre-Construction. To be built. NEW CONSTRUCTION! Introducing an exquisite new construction home in Winter Park Grove, Winter Park's newest community! This residence is carefully curated by SGC Development, a highly respected local builder known for their dedication to quality and craftsmanship. This residence combines luxury living with the utmost convenience, located within walking distance to

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  Winter Park, FL 32789
• 

  

  /46

  $1,399,000

  New Construction

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

  102 Bell Place, Winter Park, FL 32792

  Step into elevated Florida living with this stunning brand-new residence, where modern design meets lasting quality. Constructed with solid block and steel framing for superior durability, this home is quietly nestled on a cul-de-sac in one of Winter Park’s most up-and-coming areas—without the restrictions of an HOA. Just moments from Interlachen Country Club and the charming Lakemont Heights

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  102 Bell Place, Winter Park, FL 32792
• 

  

  /34

  $1,499,900

  New Construction $130K PRICE DROP

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

  607 Ellen Dr, Winter Park, FL 32789

  NEW PRICE!!! 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

  Kelly Price KELLY PRICE & COMPANY LLC

  607 Ellen Dr, Winter Park, FL 32789
• 

  

  /42

  $1,295,000

  • 4 Beds
  • 5 Baths
  • 3,971 Sq Ft

  2465 Banchory Rd, Winter Park, FL 32792

  This is the kind of place you dream of, set on one of the most beautiful streets in Winter Park, Florida, the kind you can’t wait to come home to. A place to slow down, where evening walks feel like something out of a storybook, and the Cady Way Trail is just steps from your door for morning runs, bike rides, and everything in between. This custom-built two-story residence offers 3,971 square

  Melissa Johnson EXP REALTY LLC

  2465 Banchory Rd, Winter Park, FL 32792
• 

  

  /8

  $1,360,000

  New Construction

  • 5 Beds
  • 5.5 Baths
  • 3,735 Sq Ft

  420 Ohio St, Winter Park, FL 32789

  Pre-Construction. To be built. On a prominent corner lot in the evolving Killarney neighborhood, this offering presents a rare chance to create a custom residence in the heart of the 32789 zip code. Set among a mix of established homes and new construction, the setting reflects the ongoing transformation of the area while remaining close to the amenities that define Winter Park living. The

  Leighton Hope COMPASS FLORIDA LLC

  420 Ohio St, Winter Park, FL 32789
• 

  

  /54

  $1,495,000

  $130K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft

  1077 Minnesota Ave, Winter Park, FL 32789

  Huge price improvement. Seller is relocating and motivated. Built in 2025 by Nautilus Homes and lightly lived in, this custom Winter Park residence offers a rare combination of new construction quality, thoughtful owner upgrades, and a highly desirable location between Orlando Avenue and Orange Avenue, just minutes from Park Avenue shopping, dining, and cultural attractions. Set behind mature

  Shahram Sondi SHAHRAM SONDI + CO.

  1077 Minnesota Ave, Winter Park, FL 32789
• 

  

  /24

  $1,295,000

  $55K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,667 Sq Ft

  2111 Mallard Cir, Winter Park, FL 32789

  Tucked away on a quiet circle in one of Winter Park's most sought-after neighborhoods, this distinctive pool home offers a rare opportunity. Set on an approximately .26-acre lot, the home features striking architectural lines, soaring wood ceilings with exposed beams, polished concrete flooring, and an abundance of natural light throughout. This is the only home currently for sale in Quail

  Caroline Borling BREC PROPERTIES INC

  2111 Mallard Cir, Winter Park, FL 32789
• 

  

  /59

  $1,390,000

  New Construction

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

  501 Lakeview Ave, Winter Park, FL 32789

  MOVE-IN READY! Construction Completed! 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

  Marie Ledbetter COLDWELL BANKER REALTY

  501 Lakeview Ave, Winter Park, FL 32789
• 

  

  /65

  $1,499,999

  New Construction $50K PRICE DROP

  • 5 Beds
  • 4 Baths
  • 3,164 Sq Ft

  1523 Miller Ave, Winter Park, FL 32789

  BRAND NEW CONSTRUCTION COMPLETED APRIL 2026, MOVE-IN READY. This 3,164 sqft home at 1523 Miller Ave, Winter Park, FL 32789 combines modern design, high-end finishes, and an unbeatable central location. Featuring 5 bedrooms, 4 full bathrooms, and a private salt-water pool, the home is designed for both everyday comfort and effortless entertaining. The open L-shaped living, kitchen, and dining area

  Eric Trumble II CHARLES RUTENBERG REALTY ORLANDO

  1523 Miller Ave, Winter Park, FL 32789
• 

  

  /31

  $1,495,000

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

  2408 Lafayette Ave, Winter Park, FL 32789

  This 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 apart for

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
• 

  

  /51

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft

  1347 Chapman Cir, Winter Park, FL 32789

  Beautiful Windsong custom home completely reimagined with a sophisticated interior design overhaul that now presents as a true Winter Park boutique luxury residence. This stunning 4 bedroom, 3.5 bath home blends timeless elegance, thoughtful craftsmanship, and warm entertaining spaces in one of the area’s most sought-after neighborhoods. Every room feels intentional and refined, showcasing

  Justin Pekarek ORLANDO PROPERTY ADVISORS

  1347 Chapman Cir, Winter Park, FL 32789
• 

  

  /29

  $225,000

  • 2 Beds
  • 1.5 Baths
  • 1,266 Sq Ft

  200 Saint Andrews Blvd Unit 2901, Winter Park, FL 32792

  Welcome to this spacious and well-maintained 2 story townhome in the heart of Winter Park, located in the highly sought-after Four Seasons community. This 2-bedroom, 1.5-bath unit offers 1,266 square feet of comfortable living space with a functional layout, abundant natural light, and thoughtful updates throughout. Step inside to find a spacious kitchen, renovated in 2016, featuring wood

  Amy Turner KELLER WILLIAMS WINTER PARK

  200 Saint Andrews Blvd Unit 2901, Winter Park, FL 32792
• 

  

  /49

  $1,599,000

  $96K PRICE DROP

  • 4 Beds
  • 5.5 Baths
  • 3,609 Sq Ft

  234 Detmar Dr, Winter Park, FL 32789

  Nestled behind gates in the heart of Winter park, this enchanting 1930's residence blends historic charm with many recent upgrades. The beautifully renovated kitchen anchors the home, while the downstairs primary suite offers privacy and comfort with an elegant spa inspired bath. The detached one bedroom guest house is perfect for houseguests, a home office or multi-generational living. The main

  Nicole Seybold FANNIE HILLMAN & ASSOCIATES

  234 Detmar Dr, Winter Park, FL 32789
• 

  

  /39

  $1,640,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,048 Sq Ft

  1570 Palmer Ave, Winter Park, FL 32789

  Located in the heart of Winter Park, this beautifully appointed 3,048 sq. ft. residence with saltwater pool and spa offers an ideal blend of comfort, style, and functionality. Designed for both everyday living and entertaining, the home features an open and inviting floor plan filled with natural light and high-end finishes throughout. The gourmet kitchen is equipped with granite countertops,

  David Auerbach PARK TOWN REAL ESTATE LLC

  1570 Palmer Ave, Winter Park, FL 32789
• 

  

  /51

  $1,349,900

  $100K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,223 Sq Ft

  1649 Harmon Ave, Winter Park, FL 32789

  Discover Orwin Manor, one of Winter Park’s established neighborhoods centrally located within an easy distance to the Orange Avenue WP corridor and minutes to downtown Orlando. Transitional architecture with modern leaning influences, this home is designed for ease of living. This four-bedroom 3.5-bath home stretches across nearly 3,200 square feet and features open kitchen to dining and living

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1649 Harmon Ave, Winter Park, FL 32789
• 

  

  /52

  $224,999

  $35K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 956 Sq Ft

  2500 Lee Rd Unit 202, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. MILLIONAIRE LIFESTYLE HIDDEN GEM • LAKE ACCESS • 2 BED / 2 BATH CONDO ON LAKE KILLARNEY • PRIME WINTER PARK LOCATION • LOW HOA Outstanding Opportunity to live the Florida Lifestyle in your private walkable Lakefront Enclave. Includes Direct Lake Access, Private Dock, Loungers and seating, Picnic areas and landscaping, Boat Slip, and a Private Pool &

  Alison Maltby THE ANDERSON GROUP & CO PL

  2500 Lee Rd Unit 202, Winter Park, FL 32789
• 

  

  /53

  $1,479,000

  New Construction $96K PRICE DROP

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

  1473 Berkshire Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. 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 just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean masterpiece delivers

  Milena Fernandes GOLDEN GROUP REALTY LLC

  1473 Berkshire Ave, Winter Park, FL 32789
• 

  

  /46

  $714,900

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft

  1108 Fairway Dr, Winter Park, FL 32792

  Offering 25k BELOW appraised value!! Buyer financing fell through, act quickly this one wont last long. In one of Winter Parks most sought after neighborhoods, take a look at this exceptional 3-bedroom, 2-bathroom pool home with an additional bonus space. Completely reimagined with a designer’s eye, this residence blends high-end aesthetic with the ultimate peace of mind—with a newer roof, A/C,

  Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

  1108 Fairway Dr, Winter Park, FL 32792

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 $725,000. If you put a 20% down payment of $145,000 and had a 30-year fixed mortgage with an interest rate of 6.36%, your estimated principal and interest payment would be $3,610 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $155K 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, Lake Howell, Audubon Park, Colonialtown North and College 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 73 days on the market compared to the national average of 58 days. The median sale price for homes in Winter Park, FL over the last 12 months is $637,500, down 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$637,500

Median Single Family Sale Price

$850,000

Median Townhouse Sale Price

$715,000

Median 2 Bedroom Sale Price

$227,500

Median 1 Bedroom Sale Price

$153,000

Average Price Per Sq Ft

$435

Number of Homes for Sale

208

Last 12 months Home Sales

647

Months of Supply

3.90

Median List Price

$725,000

Median Change From 1st List Price

5%

Median Home Sale Price YoY Change

-2%