Winter Park, FL Homes for Sale

• 

  

  

  /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

  440 Cambridge Blvd, Winter Park, FL 32789
• Explore Winter Park

• 

  

  

  /65

  $994,000

  Open Sat 12PM - 2PM $156K PRICE DROP

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

  1800 Magnolia Ave, Winter Park, FL 32789

  Virtually Staged. Temporarily Off the Market to replace driveway and sidewalks. PRICE IMPROVEMENT! NO HOA! Experience refined living in this renovated custom designed home on a 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.

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  1800 Magnolia Ave, Winter Park, FL 32789
• 

  

  

  /24

  $129,900

  $10K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E103, Winter Park, FL 32789

  Virtually Staged. 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 condo, you're greeted by a bright and spacious living area,

  

  Jason Price

  RE/MAX SELECT GROUP

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

  

  

  /38

  $249,900

  $10K PRICE DROP

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

  1500 Gay Rd Unit 17D, Winter Park, FL 32789

  MAJOR PRICE ADJUSTMENT!Fantastic Winter Park Location on Lake Killarney. This 2 Bedroom 2 Bath Upstairs Unit has Lake and Pool Views. Spacious Living Spaces and Generously-sized Bedrooms. Unique Updated Kitchen has Sub Zero Refrigerator, Bosch Dishwasher, Solid Surface Counters, unbelievable amount of Storage with Corner Cabinets, Drawers, pull-out Shelving and 3 Tiers of Lighting! Updates

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 17D, Winter Park, FL 32789
• 

  

  

  /28

  $199,900

  • 2 Beds
  • 1 Bath
  • 851 Sq Ft

  2500 Lee Rd Unit 220, 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 2500 Lee Road, Unit 220, in Winter Park, a beautifully maintained condominium offering stylish, low-maintenance living in one of Central Florida's most convenient locations. Inside, the condo features 2 bedrooms

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  2500 Lee Rd Unit 220, Winter Park, FL 32789
• 

  

  /22

  $258,000

  $4K PRICE DROP

  • 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

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

  

  /42

  $365,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft

  3374 Hamlet Loop, Winter Park, FL 32792

  Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  3374 Hamlet Loop, Winter Park, FL 32792
• 

  

  /37

  $835,000

  $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  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 buy-down that reduces the buyer's interest rate and monthly payment.**This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  1090 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /50

  $799,900

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,020 Sq Ft

  1287 Verdant Glade Place, Winter Park, FL 32792

  **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 1287 Verdant Glade Place in Winter Park, a spacious two-story home offering 4 bedrooms, 3 full baths, 1 half bath, and a dedicated office, all thoughtfully arranged within an open floorplan designed for both

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  1287 Verdant Glade Place, Winter Park, FL 32792
• 

  

  /36

  $220,000

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,578 Sq Ft

  7488 Whisperwood Dr Unit 28, Winter Park, FL 32792

  Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park. Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining, Covered

  

  Miranda Azer

  PARKVIEW REAL ESTATE

  7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
• 

  

  /31

  $259,000

  • 3 Beds
  • 2.5 Baths
  • 1,720 Sq Ft

  2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792

  Welcome to 2433 Grand Teton Circle in the sought-after Cedarwood Village community of Winter Park, where move-in ready living, thoughtful updates, and an unbeatable location come together. Featuring the largest floor plan in the community, this spacious condo has been refreshed with brand-new carpet and fresh interior paint, offering a bright, inviting space that’s ready for its next owner. The

  

  Alexis Jacobsen

  EXP REALTY LLC

  2433 Grand Teton Cir Unit 112433, Winter Park, FL 32792
• 

  

  /46

  $320,000

  • 2 Beds
  • 2 Baths
  • 1,086 Sq Ft

  5781 Shale Ct, Winter Park, FL 32792

  **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 5781 Shale Court in Winter Park, a 2-bedroom, 2-bath home designed for comfortable everyday living. This one-story residence offers a practical layout with space for relaxing, dining, and hosting guests. The

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  5781 Shale Ct, Winter Park, FL 32792
• 

  

  /29

  $278,000

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft

  2475 Tahoe Cir, Winter Park, FL 32792

  Turnkey Living in the Heart of Winter Park!Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner.Inside, you'll find a thoughtfully

  

  Sarah Doyer

  COLDWELL BANKER REALTY

  2475 Tahoe Cir, Winter Park, FL 32792
• 

  

  /15

  $175,000

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 4D, Winter Park, FL 32789

  Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping!One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional Built-in Closets, Vanity and

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 4D, Winter Park, FL 32789
• 

  

  /43

  $465,000

  Open Sat 11AM - 2PM $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,622 Sq Ft

  3641 Hawthorne Ln, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home nestled in the highly desirable Winter Park area. Combining comfort, style, and an unbeatable location, this charming residence offers the perfect opportunity for homeowners seeking a move-in-ready property in one of Central Florida's most sought-after communities. Step inside to discover a bright and inviting floor plan designed

  

  Keegan Siegfried

  LPT REALTY, LLC

  3641 Hawthorne Ln, Winter Park, FL 32792
• 

  

  /55

  $540,000

  • 3 Beds
  • 2 Baths
  • 1,618 Sq Ft

  228 Rippling Ln, Winter Park, FL 32789

  Welcome to Winter Park and the beautiful and desirable Lake Killarney Shores Neighborhood. Available for the first time in 25 years, this home is nestled on an oversized .35 acre lot with plenty of room to store a boat along with deeded lake access to Lake Killarney and NO HOA!! This Classic Florida Home is filled with natural light and features a spacious floorplan including 3 Bedrooms, 2 Full

  

  Nicholas Wild

  GATE PROPERTIES & MANAGEMENT INC

  228 Rippling Ln, Winter Park, FL 32789
• 

  

  /49

  $1,149,900

  $49K PRICE DROP

  • 5 Beds
  • 4.5 Baths
  • 3,652 Sq Ft

  1448 Lake Florence Way, Winter Park, FL 32792

  Located within an intimate gated community of just 28 homes and only a short drive to Downtown Winter Park, this exceptional former model home by K. Hovnanian Homes showcases over $200,000 in builder and custom upgrades with luxury finishes and thoughtful design throughout. Residents enjoy access to a private community dock, perfect for launching a canoe or paddleboard or simply relaxing while

  Abby Nelson RE/MAX 200 REALTY

  1448 Lake Florence Way, Winter Park, FL 32792
• 

  

  /28

  $324,900

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft

  7426 Blue Jacket Place E, Winter Park, FL 32792

  Virtually Staged. Opportunity Awaits in the Heart of Winter Park! Welcome to 7426 Blue Jacket Place, a 3-bedroom, 2-bathroom home that's ready for its next chapter. Nestled on a quiet street in an established neighborhood, this property offers a fantastic opportunity for buyers looking to add their personal touch and create the home of their dreams. Plus, enjoy added peace of mind knowing the

  Abby Nelson RE/MAX 200 REALTY

  7426 Blue Jacket Place E, Winter Park, FL 32792
• 

  

  /71

  $685,000

  $15K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,702 Sq Ft

  3114 Heartleaf Place, Winter Park, FL 32792

  Tucked away on a rare and breathtaking .96-acre homesite, this one-of-a-kind property in Lost Creek offers a setting that feels more like a private nature retreat than a suburban neighborhood. Surrounded by protected wooded conservation land and stretching back to the serene Howell Creek, this home delivers unmatched privacy, beauty, and a daily connection to nature. From the moment you arrive,

  Nadia Kurakin CHAMPION HOMES

  3114 Heartleaf Place, Winter Park, FL 32792
• 

  

  /22

  $180,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,105 Sq Ft

  2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792

  PRICE IMPROVEMENT! TOP FLOOR CORNER UNIT in the heart of Winter Park! This well-maintained 2-bedroom, 2-bath condo offers spacious living, abundant natural light, and a functional open layout perfect for everyday living or investment potential. Step inside to find a bright and airy living and dining area with sliding glass doors leading to a private screened-in balcony — the perfect spot to relax

  Steven Pugh EXP REALTY LLC

  2923 Antique Oaks Cir Unit 34, Winter Park, FL 32792
• 

  

  /40

  $575,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft

  2010 Summerfield Rd, Winter Park, FL 32792

  Welcome to this beautifully maintained and thoughtfully updated home in the desirable City of Winter Park, offering an exceptional blend of comfort, space, and convenience. From the moment you arrive, the freshly installed, vibrant green front lawn and attractive landscaping create an inviting first impression. Inside, the cathedral ceiling enhances the spacious feel of the open floor plan,

  Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  2010 Summerfield Rd, Winter Park, FL 32792
• 

  

  /20

  $458,000

  $42K PRICE DROP

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

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this beautifully remodeled, move-in-ready home in the highly sought-after Winter Park area. This single-story residence features 4 bedrooms and 2 bathrooms, offering a bright, open floor plan with modern finishes designed for both comfort and functionality. A standout feature of this property is its commitment to sustainable living and energy efficiency. Highlights include: - Newer

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
• 

  

  /34

  $1,350,000

  • 3 Beds
  • 2.5 Baths
  • 2,607 Sq Ft

  3069 Stanfield Ave, Orlando, FL 32814

  This exceptional Baldwin Park residence pairs a charming craftsman exterior with a masterfully reimagined interior that blends warm character and a clean, modern aesthetic. The grand entrance immediately sets the tone with a stylish staircase featuring automatic LED lighting, a light-toned wooden handrail, and sleek horizontal black metal infill bars. Nearby, a private front study serves as a

  Brian Cirillo BALDWIN PARK REALTY LLC

  3069 Stanfield Ave, Orlando, FL 32814
• 

  

  /59

  $675,000

  $75K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
• 

  

  /51

  $2,650,000

  New Construction $150K PRICE DROP

  • 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
• 

  

  /5

  $138,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  1000 S Semoran Blvd Unit 404, Winter Park, FL 32792

  Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 404, Winter Park, FL 32792
• 

  

  /50

  $1,800,000

  Open Sat 1PM - 4PM $200K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,065 Sq Ft

  723 Symonds Ave, Winter Park, FL 32789

  Built by Clarkson Concepts and ideally located in the heart of Winter Park just moments from Park Avenue, this sophisticated modern residence blends luxury design, smart-home innovation, and effortless indoor-outdoor living across three thoughtfully designed levels. From the moment you arrive, the striking foyer makes a memorable first impression with its bold geometric detailing, designer

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  723 Symonds Ave, Winter Park, FL 32789
• 

  

  /28

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7522 Aloma Pines Ct, Winter Park, FL 32792

  Beautifully maintained 3-bedroom, 2.5-bath two-story townhome featuring a bright and functional open-concept floor plan. The first floor offers tile flooring throughout the spacious living and dining areas, kitchen, and half bath. The modern kitchen is designed for both style and convenience, featuring granite countertops, abundant cabinetry, a large center island, and a walk-in pantry, along

  Vildan Nigro RIVA REALTY GROUP LLC

  7522 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /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
• 

  

  /53

  $4,250,000

  • 4 Beds
  • 6 Baths
  • 4,431 Sq Ft

  229 Alexander Place, Winter Park, FL 32789

  Envisioned by acclaimed architect Phil Kean and originally commissioned as the International Showcase Home for the National Association of Home Builders, this award-winning contemporary estate is a masterclass in modern design. Tucked away on a prestigious cul-de-sac between Lake Osceola and the iconic Alfond Inn, the residence offers unparalleled privacy just two blocks from Park Avenue's

  Brandon Geers COMPASS FLORIDA LLC

  229 Alexander Place, Winter Park, FL 32789
• 

  

  /39

  $574,900

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  1354 Indiana Ave, Winter Park, FL 32789

  Virtually Staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle.The beautifully renovated interior features a

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  1354 Indiana Ave, Winter Park, FL 32789
• 

  

  /76

  $6,495,000

  New Construction $705K PRICE DROP

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
• 

  

  /42

  $285,000

  • 2 Beds
  • 2 Baths
  • 1,495 Sq Ft

  2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792

  Welcome to this beautifully updated condo, ideally nestled between Winter Park and Maitland. This inviting home features a versatile upstairs loft overlooking the living and dining areas—perfect for a home office, fitness space, craft room, or additional guest accommodations. The bright, cheerful eat-in kitchen is both stylish and functional, showcasing quartz countertops, a glass tile

  Sheila Mathews COLDWELL BANKER REALTY

  2372 Sun Valley Cir Unit 2372, Winter Park, FL 32792
• 

  

  /60

  $384,900

  $15K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,534 Sq Ft

  1662 Tremont Ln, Winter Park, FL 32792

  Back on the Market - Buyer Financing fell through. Turnkey and move-in ready! This beautifully updated 3-bedroom, 2-bath home offers modern finishes and an ideal floor plan in a fantastic location! Recent improvements include fresh interior and exterior paint, new flooring throughout, a fully renovated kitchen, and updated bathrooms. Roof (2022) Enjoy comfortable living with thoughtfully updated

  Michael Heacock Results Team Prop.& Investment

  1662 Tremont Ln, Winter Park, FL 32792
• 

  

  /11

  $138,000

  $10K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft

  1000 S Semoran Blvd Unit 408, Winter Park, FL 32792

  Great for INVESTORS!..instant rent upon closing, start collecting the day after closing!!..Also can be great Spacious Other units currently available in same complex Great starter home../ ONE bedroom condo in Golfside Villas located in the heart of Winter Park. Great location for travel to Winter Park, Full Sail, UCF and/or the airport. Low HOA fees that cover all exterior items, along with pool

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 408, Winter Park, FL 32792
• 

  

  /6

  $2,235,000

  New Construction

  • 5 Beds
  • 4.5 Baths
  • 4,150 Sq Ft

  926 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

  926 Enclave Place, Winter Park, FL 32792
• 

  

  /6

  $99,000

  • Studio
  • 1 Bath
  • 537 Sq Ft

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

  Lynda Cheros GOLDENCREST REALTY LLC

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
• 

  

  /82

  $920,000

  • 4 Beds
  • 3 Baths
  • 3,063 Sq Ft

  1492 Via Sangro Place, Winter Park, FL 32792

  Experience refined Florida living in this exceptional single-story residence, ideally situated on a quiet cul-de-sac within an intimate gated community in one of Winter Park's most desirable locations. Impeccably maintained, this elegant home offers over 3,000 square feet of thoughtfully designed living space with 4 bedrooms, 3 full baths, a private office, and a desirable three-way split floor

  Maha Matta PA RE/MAX TOWN & COUNTRY REALTY

  1492 Via Sangro Place, Winter Park, FL 32792
• 

  

  /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
• 

  

  /19

  $530,000

  • 3 Beds
  • 1.5 Baths
  • 1,314 Sq Ft

  2552 Brookshire Ave, Winter Park, FL 32792

  Listed for lot value, this exceptional 75' x 119' homesite presents a rare opportunity to build your dream home in one of Winter Park's most sought-after neighborhoods. Surrounded by stunning new construction, this highly desirable location is ideal for creating a custom residence tailored to your lifestyle. Enjoy the convenience of being zoned for highly regarded Winter Park schools and just

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  2552 Brookshire Ave, Winter Park, FL 32792

Showing Results 1 - 40, Page 1 of 9

Why Live in Winter Park

Winter Park, located near Orlando, Florida, began in the 1880s as a planned community appealing to northern ex-pats with its warm winters, good schools, and lively arts scene. Today, it maintains its "City of Arts and Culture" nickname with museums and a vibrant cultural atmosphere. The main commercial district, Park Avenue, features high-end boutiques and bistros, including The Ravenous Pig, a renowned gastropub. Rollins College and The Rollins Museum of Art are local highlights, along with The Alfond Inn, which serves as a social hub. The city’s nearly 30,000 residents enjoy highly rated schools such as Winter Park High and Trinity Preparatory School of Florida. Housing options range from petite bungalows to lakeside mansions, with styles including New Traditional, midcentury-era ranch homes, Colonial Revival, and Contemporary homes. The Winter Park Chain of Lakes offers boating, kayaking, and paddleboarding opportunities, while Central Park provides 11 acres of green space with walking paths and a rose garden. Annual events like the Winter Park Sidewalk Arts Festival and Christmas on Park attract visitors and foster community spirit. Residents have access to Interstate 4, SunRail, and Lynx buses for transportation, with Orlando International Airport about 20 miles away. Winter Park’s crime rates are lower than the national average, making it a safer area compared to nearby Orlando.

Learn more about living in Winter Park

Frequently Asked Questions

What is the average home price in Winter Park, FL?

Homes for sale in Winter Park, FL have an average home price of $951,758.

How many homes have sold over the last 12 months in Winter Park, FL?

1,016 homes have sold in Winter Park, FL over the last 12 months.

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

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

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

The median home price in Winter Park is $530,000. If you put a 20% down payment of $106,000 and had a 30-year fixed mortgage with an interest rate of 6.58%, your estimated principal and interest payment would be $2,700 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $116K a year to afford the median home price in Winter Park. Learn how much home you can afford with our Home Affordability Calculator.

How are the schools in Winter Park, FL?

Winter Park, FL has highly rated public and private schools. Some of the best schools in Winter Park based on Niche Grades are Lake Highland Preparatory School, Park Maitland School and Trinity Preparatory School. Browse all the schools in Winter Park, FL to learn more.

Home Prices in Winter Park, FL

The median home sale price in Winter Park, FL is $485,000, up 2% year-over-year. Homes in Winter Park sell in 66 days on average, compared to the national average of 56 days.

Home Price Trends

Median Sale Price $485,000	Median Single Family Sale Price $610,000
Median Townhouse Sale Price $430,000	Median 2 Bedroom Sale Price $255,000
Median 1 Bedroom Sale Price $157,750	Average Price Per Sq Ft $372
Number of Homes for Sale 313	Last 12 months Home Sales 1,016
Months of Supply 3.70	Median List Price $530,000
Median Change From 1st List Price 5%	Median Home Sale Price YoY Change 2%