Winter Park, FL Homes

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  /96

  $2,599,000

  • 5 Beds
  • 4.5 Baths
  • 3,882 Sq Ft

  1781 Pine Ave, Winter Park, FL 32789

  An exceptional custom home by award-winning Davila Homes, perfectly blending modern design and functionality. Located in sought-after Conwill Estates, just minutes from Park Avenue, this 5-bed, 4.5-bath residence features volume ceilings, floor-to-ceiling bronze sliding doors, and a seamless indoor-outdoor living experience.The chef’s kitchen showcases waterfall quartz countertops,

  Mulcy Tenorio FLORIDA CONNEXION PROPERTIES

  1781 Pine Ave, Winter Park, FL 32789
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  /4

  $2,695 per month

  • 3 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Townhouse for Rent

  7518 Aloma Pines Ct, Winter Park, FL 32792

  Welcome to 7518 Aloma Pines Ct, a modern 3-bedroom, 2.5-bath townhome in the heart of Winter Park, FL. Set in a quiet, gated community, this 1,872 sq ft residence blends upscale living with smart home features — including a built-in 5.1 surround sound system for a theater-quality experience.Interior Highlights:•Chef’s kitchen with granite countertops, 42” wood cabinetry, stainless

  7518 Aloma Pines Ct, Winter Park, FL 32792
• 

  

  /2

  $390,000 Sold Jun 04, 2025

  • 1,727 Sq Ft
  • $226/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1973

  264 Balfour Dr, Winter Park, FL 32792

  Welcome to 264 Balfour Drive — an exclusive residence within a private enclave of just 13 elegant townhomes in the heart of Winter Park designed by architect Nils Schweizer. a student of Frank Lloyd Wright. Offering an attached two-car garage and a premier location, this home blends sophistication with comfort in every detail.Step into a grand living room where soaring ceilings and expansive

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  264 Balfour Dr, Winter Park, FL 32792
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  /9

  Est $428,663 Not Listed For Sale

  • 2 Beds

  822 Symonds Ave, Winter Park, FL 32789

  822 Symonds Ave, Winter Park, FL 32789
• 

  

  

  /40

  $500,000

  • 4 Beds
  • 2.5 Baths
  • 2,075 Sq Ft

  Unlisted Address

  Welcome to this beautifully maintained 4-bedroom, 2.5-bath pool home nestled in a peaceful neighborhood. This two-story gem offers a spacious and functional layout perfect for both relaxing and entertaining. The 1st floor master is spacious and inviting. Enjoy peace of mind with a newer roof and windows, as well as brand-new laminate flooring throughout the main living areas. Upstairs, a

  Luke Lewis TREASURE COAST REALTY GROUP, LLC

  Unlisted Address
• 

  

  /30

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,812 Sq Ft
  • House for Rent

  2101 Oakhurst Ave, Winter Park, FL 32792

  Immaculately maintained, this three-bedroom, two-bathroom home is nestled in the heart of Winter Park. Sitting on just under a quarter-acre lot, it boasts a new AC system and a charming stone fireplace. You’re only minutes away from downtown Winter Park and the vibrant shopping and dining options along Park Avenue. Enjoy the nearby perks of the YMCA Fitness Center, just blocks away, and the

  Peter Dang ALLIANCE RENTAL HOMES

  2101 Oakhurst Ave, Winter Park, FL 32792
• 

  /2

  $460,000 Sold Jun 04, 2025

  • 2,076 Sq Ft
  • $222/SF
  • 30 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  1628 Little Wren Ln, Winter Park, FL 32792

  Improved Price! Welcome to your private "nest" on Little Wren. Nestled among the trees, this modern masterpiece is located directly next to a wide open green space and also backs to a private wooded area giving you beautiful, natural, unobstructed views. The home's modern architecture style is evident from the moment you approach with its striking front door acting as a key focal point.

  Kristin Haughwout-Osorio PARKSIDE PROPERTIES, LLC

  1628 Little Wren Ln, Winter Park, FL 32792
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  /42

  Est $704,523 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft

  1252 Verdant Glade Place, Winter Park, FL 32792

  1252 Verdant Glade Place, Winter Park, FL 32792
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  /70

  $472,000

  • 3 Beds
  • 2 Baths
  • 1,623 Sq Ft

  2648 Amsden Rd, Winter Park, FL 32792

  Beautiful Pool Home in Desirable Winter Park EstatesWelcome to this charming and thoughtfully updated pool home in the highly sought-after Winter Park Estates subdivision—zoned for top-rated schools, including Winter Park High School. This mid-century gem blends modern comfort with timeless style, located in one of Central Florida’s most beloved neighborhoods.Property

  Mary Dees CHOICEPOINTE REALTY, INC.

  2648 Amsden Rd, Winter Park, FL 32792
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  /28

  $1,100 per month

  • 1 Bed
  • 1 Bath
  • 408 Sq Ft
  • House for Rent

  5058 Seminole Ave Unit Seminole Unit 4, Winter Park, FL 32792

  Attention Full Sail and UCF Students! This is the place for which you've been looking. This is a shared living space that is fully furnished with all utilities included. Each of the 4 rooms has its own electronic keypad lock for your privacy and security. The extra large common areas provide the perfect space for dining and living. Spacious laundry and kitchen provide you with plenty of space

  5058 Seminole Ave Unit Seminole Unit 4, Winter Park, FL 32792
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  /2

  $835,000 Sold Jun 03, 2025

  • 2,133 Sq Ft
  • $391/SF
  • 63 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1958

  625 Worthington Dr, Winter Park, FL 32789

  Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  625 Worthington Dr, Winter Park, FL 32789
• 

  

  /36

  Est $777,497 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,822 Sq Ft

  5263 Pine Lily Cir, Winter Park, FL 32792

  5263 Pine Lily Cir, Winter Park, FL 32792
• 

  

  /25

  $299,900

  • 3 Beds
  • 1 Bath
  • 1,114 Sq Ft

  7102 Easter St, Winter Park, FL 32792

  Welcome to a Rare Gem in Winter Park!Step into a vibrant slice of Winter Park history at 7102 Easter Street—a charming 1956-built home bursting with vintage character and endless possibilities! From the moment you arrive, you'll feel the warmth and nostalgia of this beautifully maintained residence, where classic mid-century style meets modern-day potential.Inside, you’ll find 3

  Mayken Giraldo CHARLES RUTENBERG REALTY ORLANDO

  7102 Easter St, Winter Park, FL 32792
• 

  

  /20

  $3,400 per month

  • 3 Beds
  • 1.5 Baths
  • 1,409 Sq Ft
  • House for Rent

  532 Darcey Dr, Winter Park, FL 32792

  This 3 bedroom/1.5 bathroom CORNER lot home is located in the desirable Brookshire Heights neighborhood. The home was redesigned in 2020 and has since been upgraded even further! No detail was overlooked in this adorable midcentury home. Brand new roof completely replaced in 2023 with new fascia, soffits, and gutters. Exterior just painted in 2023. Newly remodeled kitchen features Quartz

  Wenwen Wang JWJ REALTY LLC

  532 Darcey Dr, Winter Park, FL 32792
• 

  /2

  $402,500 Sold Jun 02, 2025

  • 1,379 Sq Ft
  • $292/SF
  • 5 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  1301 Paradise Ln, Winter Park, FL 32792

  This fully reimagined corner-lot residence is more than a renovation; it’s a masterpiece, designed for modern living. Sited on nearly 0.40 acres, the home greets you with bold curb appeal, and sleek paver driveway that signal something truly special inside.

  Ahmad Hassan COMPASS FLORIDA LLC

  1301 Paradise Ln, Winter Park, FL 32792
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  /47

  Est $2,532,641 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,104 Sq Ft

  1721 Edwin Blvd, Winter Park, FL 32789

  1721 Edwin Blvd, Winter Park, FL 32789
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  /60

  $1,470,000

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

  2401 Lafayette Ave, Winter Park, FL 32789

  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 most sought-after neighborhoods.From the moment you enter,

  Nehad Darwish DIVINE ESTATES REALTY LLC

  2401 Lafayette Ave, Winter Park, FL 32789
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  /10

  $1,500 per month

  • 2 Beds
  • 1 Bath
  • 1,078 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C-214, Winter Park, FL 32789

  This is a 2/2 on a second floor this unit has stackable W/D. This ample unit also has new appliance and a balcony. .

  1695 Lee Rd Unit C-214, Winter Park, FL 32789
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  /2

  $392,500 Sold Jun 02, 2025

  • 1,427 Sq Ft
  • $275/SF
  • 24 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  2100 Shirewood Ct, Winter Park, FL 32792

  This 3-bedroom, 2-bathroom residence is situated on a corner lot, offering an inviting and comfortable living space. A notable feature of this property is the BRAND NEW ROOF and WATER HEATER, ensuring peace of mind for years to come. The split floor plan enhances both privacy and functionality. The master bedroom boasts a walk-in closet and a private ensuite bathroom. On the opposite side of the

  karen akos WEICHERT REALTORS HALLMARK PRO

  2100 Shirewood Ct, Winter Park, FL 32792
• 

  

  /25

  Est $170,081 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft

  678 Trinidad Ct Unit S, Winter Park, FL 32792

  678 Trinidad Ct Unit S, Winter Park, FL 32792
• 

  

  /84

  $445,000

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  1900 Erudite Way, Winter Park, FL 32792

  Step into effortless style and comfort in this beautifully crafted 2024 townhome located in Winter Park's desirable Grayson Square community. From the moment you arrive, you’ll appreciate the home’s modern curb appeal and smart features, including a convenient keypad entry and smart lighting throughout.Inside, an open-concept layout welcomes you with rich wood floors, designer lighting,

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, Winter Park, FL 32792
• 

  

  /23

  $1,650 per month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great location. Don’t miss the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
• 

  /2

  $615,000 Sold Jun 02, 2025

  • 2,197 Sq Ft
  • $280/SF
  • 5 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1964

  2712 Cady Way Unit 4, Winter Park, FL 32792

  Welcome to your tropical paradise in the highly sought-after Winter Park Pines neighborhood, where the mailman still delivers to your front door! This beautiful home radiates true Florida vibes with whimsical details and thoughtful touches throughout. As you step inside, you'll be greeted by an open living and dining area featuring two sets of French doors that lead to a lush, private backyard

  Amy Turner KELLER WILLIAMS WINTER PARK

  2712 Cady Way Unit 4, Winter Park, FL 32792
• 

  

  /31

  Est $453,011 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2891 Clever Ln, Winter Park, FL 32792

  2891 Clever Ln, Winter Park, FL 32792
• 

  

  /32

  $2,749,000

  • 3 Beds
  • 3 Baths
  • 2,143 Sq Ft

  140 E Morse Blvd Unit J, Winter Park, FL 32789

  Experience the pinnacle of luxury living in the heart of downtown Winter Park with this stunning penthouse residence at The Landmark—an exclusive enclave of just 13 finely appointed condominiums along Park Avenue’s iconic brick streets. Amid award-winning restaurants, boutique shops, charming sidewalk cafes and art galleries, this elegant condominium offers the ultimate in urban sophistication

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  140 E Morse Blvd Unit J, Winter Park, FL 32789
• 

  

  /10

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 813, Winter Park, FL 32792

  This roomy 2/2 condo located in Golf side Villas, off South Semoran Boulevard, minutes away from shopping and Baldwin Park, Golf side Villas has a community pool and laundry facilities are conveniently located in the community, close to this unit. The unit features tile floors throughout, offers a nice size family room and dining area. The kitchen has granite counter tops, a large stainless steel

  Caroline Perotti BELLA VIEW REALTY LLC

  1000 S Semoran Blvd Unit 813, Winter Park, FL 32792
• 

  /2

  $370,000 Sold Jun 01, 2025

  • 1,409 Sq Ft
  • $263/SF
  • 12 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1958

  2805 Bongart Rd, Winter Park, FL 32792

  Welcome to this charming 3-bedroom, 2-bathroom single-story home, perfectly located in highly sought-after Winter Park. Situated on a beautiful corner lot, this property offers the ultimate in convenience and charm, with the added bonus of NO HOA! Ideal for first-time homebuyers or investors, this home boasts low-maintenance tile and laminate flooring throughout. The spacious living room is the

  Jamie Stolinas Crame CENTURY 21 CARIOTI

  2805 Bongart Rd, Winter Park, FL 32792
• 

  

  /28

  Est $735,330 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,577 Sq Ft

  1300 Blue Stem Ln, Winter Park, FL 32792

  1300 Blue Stem Ln, Winter Park, FL 32792
• 

  

  /45

  $575,000 Open Sun 1PM - 4PM

  • 2 Beds
  • 1 Bath
  • 789 Sq Ft

  1339 Orchid Ave, Winter Park, FL 32789

  A rare find in Winter Park: A charming Bungalow with 3-Car Garage (24x36) and detached finished Shed (10x14) for office & or additional Storage! Walking distance to Mead Gardens and the new Seven Oaks Park. Convenient to Rollins College, Park Avenue and Winter Park Village, featuring multiple local eateries and restaurants. Just one mile to Hospital, Science Center and Museum. Easy access to

  Barbara Allen ABIDE REALTY

  1339 Orchid Ave, Winter Park, FL 32789
• 

  

  /21

  $6,800 per month

  • 3 Beds
  • 2.5 Baths
  • 2,008 Sq Ft
  • House for Rent

  2237 Howard Dr, Winter Park, FL 32789

  We are focused on short term rentals. Contact owner / agent for dates already booked. You will be amazed by the natural beauty of the waterfront and century oaks that welcome you every time you come through your front door. Come see this fully furnished, masterfully remodeled, 3 bedroom, 2 bath, with a hidden half bath in the office. A Mid-modern home that represents everything that is lakefront

  Ryan Feely COLEDEV REAL ESTATE LLC

  2237 Howard Dr, Winter Park, FL 32789
• 

  /2

  $1,002,000 Sold May 31, 2025

  • 2,295 Sq Ft
  • $437/SF
  • 4 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1989

  1265 Park Pointe Ln, Winter Park, FL 32789

  Welcome home to this beautifully upgraded gem nestled in the heart of Winter Park. This move-in-ready home sits on a quiet street, offering easy access to major highways, top-rated schools, upscale dining, shopping, and Central Florida’s best attractions.No detail has been overlooked in this full renovation. The custom kitchen is a chef’s dream—featuring quartz countertops, an oversized island

  Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
• 

  

  /26

  Est $457,721 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2009 Canny Cove, Winter Park, FL 32792

  2009 Canny Cove, Winter Park, FL 32792
• 

  

  /17

  $130,000

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft

  1000 S Semoran Blvd Unit 415, Winter Park, FL 32792

  PRICE REDUCTION!!! INVESTMENT PROPERTY, Great Tenant in place! Spacious Ground-Floor Apartment with Outdoor Terrace Discover this charming and spacious ground-floor apartment, perfect for comfortable living and entertaining. Featuring a private outdoor terrace, this property provides the ideal setting for enjoying fresh air and relaxation without ever needing to climb stairs. Key highlights of

  Jhoana Loyo Urrutia LA ROSA REALTY LLC

  1000 S Semoran Blvd Unit 415, Winter Park, FL 32792
• 

  

  /11

  $5,495 per month

  • 5 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • House for Rent

  433 Carolina Ave, Winter Park, FL 32789

  A stunning two-story house with five bedrooms is now available. The house has ceramic tittle except for the bedrooms which have wood floors The kitchen is spacious and features an island and stainless steel appliances. All the bedrooms have ceiling fans and numerous upgrades. The house is conveniently located near Winter Park farmers, enjoy Park Avenue or Winter Park Village, and amazing night

  Valentina Rodriguez LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  433 Carolina Ave, Winter Park, FL 32789
• 

  /2

  $520,000 Sold May 30, 2025

  • 943 Sq Ft
  • $551/SF
  • 41 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1956

  2507 Lafayette Ave, Winter Park, FL 32789

  ***Premier Land Opportunity on Lafayette Avenue, Winter Park, FL**Take advantage of an exceptional opportunity to own a prime piece of land in the highly desirable area of Winter Park, FL. This 7,734 sq. ft. lot on Lafayette Avenue offers an unparalleled chance to build the custom home of your dreams in one of Central Florida's most sought-after neighborhoods.With generous dimensions and

  William Grim, III RE/MAX ASSURED

  2507 Lafayette Ave, Winter Park, FL 32789
• 

  

  /31

  Est $460,750 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2021 Canny Cove, Winter Park, FL 32792

  2021 Canny Cove, Winter Park, FL 32792
• 

  

  /70

  $2,849,000 Open Sun 12PM - 4PM

  • 5 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  2652 Lake Howell Ln, Winter Park, FL 32792

  This approximately 4200 square foot home is situated on a 1.68-acre gorgeous lakefront lot in the desirable Winter Park area. The property features a completely updated main house with five bedrooms and three and a half bathrooms, flex room to be used as an office,game or exercise room, total of five-car garage and additional storage in the basement. The three-car air-conditioned garage

  Brigitte Elzarki COLDWELL BANKER REALTY

  2652 Lake Howell Ln, Winter Park, FL 32792
• 

  

  /17

  $1,175 per month

  • 1 Bed
  • 1 Bath
  • 549 Sq Ft
  • Condo for Rent

  3035 George Mason Ave Unit 20, Winter Park, FL 32792

  Welcome to 3035 George Mason Avenue, Unit #20B—a cozy and inviting 1-bedroom, 1-bathroom retreat in the heart of beautiful Winter Park, Florida! This charming home offers a bright and comfortable living space, perfect for anyone looking for convenience and tranquility. Nestled within a friendly community, you'll enjoy access to a sparkling community pool, nearby shopping centers, supermarkets,

  Myland Roo De Vargas EXP REALTY LLC

  3035 George Mason Ave Unit 20, Winter Park, FL 32792
• 

  /2

  $1,550,000 Sold May 30, 2025

  • Land
  • 0.30 Acre
  • $5,166,667 per Acre

  • 42 Days On Market

  1181 Via Capri, Winter Park, FL 32789

  This is your chance to create the home of your dreams in one of Winter Park’s most sought-after neighborhoods. Situated on an oversized 80 x 180 lot (0.30 acres), this property offers ample space and endless potential. The existing structure has already been removed, making way for a seamless building process.Enjoy a walkable lifestyle with the Winter Park Racquet Club just steps away and the

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  1181 Via Capri, Winter Park, FL 32789
• 

  

  /32

  Est $446,741 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft

  2025 Canny Cove, Winter Park, FL 32792

  2025 Canny Cove, Winter Park, FL 32792

Showing Results 561 - 600, Page 15 of 18