Winter Park, FL Homes

• 

  

  

  /25

  $159,900

  • 2 Beds
  • 2 Baths
  • 1,049 Sq Ft

  1000 S Semoran Blvd Unit 608, Winter Park, FL 32792

  Beautifully Remodeled 2-Bedroom Condo Near Full Sail.Great first home or investment property.Discover the perfect blend of comfort and convenience in this beautifully updated 2-bedroom, 2-bathroom second-floor condo, just a short walk from Full Sail University. Ideally located minutes from top hospitals, shopping, dining, and only 15-20 minutes from UCF and Orlando International Airport,

  Maria Peralta CHARLES RUTENBERG REALTY ORLANDO

  1000 S Semoran Blvd Unit 608, Winter Park, FL 32792
• 

  

  /2

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792

  LOCATION, LOCATION, LOCATION! This well-maintained 2-bedroom, 2-bath condo available for rent is perfectly situated near Full Sail University, UCF, Valencia College, Rollins College. The home features an eat-in kitchen, a spacious great room, a convenient storage room, and a tranquil rear patio—ideal for relaxing outdoors. Enjoy easy access to bike trails, shopping, dining, churches, retail

  Praveen Setty RIGHTHOUSE REALTY LLC

  3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792
• 

  

  /2

  $498,000 Sold May 28, 2025

  • 1,740 Sq Ft
  • $286/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  808 Denton Rd, Winter Park, FL 32792

  Step into a slice of mid-century magic, your private oasis awaits. On an oversized corner lot with no rear neighbors, this one-of-a-kind mid-century gem is more than just a home, it’s an experience. With classic architectural charm, lush landscaping and thoughtful updates, you’ll feel like you’ve stepped back in time without sacrificing modern-day comforts. Enjoy the tranquility of nature with

  Julie Vega-Dominguez PREMIER SOTHEBY'S INTL. REALTY

  808 Denton Rd, Winter Park, FL 32792
• 

  

  

  /66

  Est $787,878 Not Listed For Sale

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

  1006 Wildmeadow Run, Winter Park, FL 32792

  1006 Wildmeadow Run, Winter Park, FL 32792
• 

  

  

  /24

  $650,000

  • 4 Beds
  • 2 Baths
  • 2,003 Sq Ft

  1507 Golfside Dr, Winter Park, FL 32792

  LOCATION, LOCATION, LOCATION! Peace, quiet, and golf course living! This truly rare opportunity places you alongside the 13th tee and offers tranquil backyard views of the 16th fairway of Winter Park’s beautiful WP18 golf course—a picturesque links-style setting in Winter Park. Tree-lined street welcomes you to this serene setting with NO neighbors front, back or side yard!This single

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  1507 Golfside Dr, Winter Park, FL 32792
• 

  /2

  $2,750 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  2748 Bright Bird Ln, Winter Park, FL 32792

  2023 Townhome with 3 bedrooms and 2.5 bathrooms located in gated community a resort-style pool with a cabana. High-speed 1GB fiber optic internet and 75 cable channels are included in the rent. Enclosed attached 1 car garage and driveway parking. Stone countertops, SS appliances, and tile floors on level one, all bedrooms and laundry are upstairs.

  Hasan Shahab EXP REALTY LLC

  2748 Bright Bird Ln, Winter Park, FL 32792
• 

  /2

  $477,500 Sold May 28, 2025

  • 2,035 Sq Ft
  • $235/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1986

  1532 Lawndale Cir, Winter Park, FL 32792

  Welcome to Your Florida Oasis in Winter Park!This beautifully maintained 4-bedroom, 3-bathroom home offers 2,035 sq. ft. of comfortable living space, perfect for families or anyone who loves to entertain. Featuring a newer roof (2021) and updated windows with stunning custom shutters, this home combines timeless charm with modern convenience.The kitchen is a chef’s dream, boasting solid wood

  David Coker KELLER WILLIAMS WINTER PARK

  1532 Lawndale Cir, Winter Park, FL 32792
• 

  

  /48

  Est $587,982 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,268 Sq Ft

  7875 Pleasant Pine Cir, Winter Park, FL 32792

  7875 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /24

  $130,000

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

  7449 Daniel Webster Dr Unit 3, Winter Park, FL 32792

  Discover this 2-bedroom, 2-bathroom condo located in The Colonies community in Winter Park. Situated near UCF, Valencia College, and Full Sail University, this property offers convenient access to major highways, shopping centers, and dining options. The unit features a practical layout, generously sized bedrooms, and a private balcony. Community amenities include a swimming pool. A great

  Chris Creegan CREEGAN GROUP

  7449 Daniel Webster Dr Unit 3, Winter Park, FL 32792
• 

  /2

  $1,375,000 Sold May 28, 2025

  • 2,481 Sq Ft
  • $554/SF
  • 4 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1951

  1633 Pine Ave, Winter Park, FL 32789

  This home is a charming and meticulously maintained single-story family home nestled on a quiet street located on an expansive beautifully landscaped lot. As you enter, you're greeted by a private office with French doors to the left, and to the right, a cozy family room featuring a decorative fireplace. The open concept living and dining areas overlook the backyard, creating a perfect flow for

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  1633 Pine Ave, Winter Park, FL 32789
• 

  

  /20

  Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,090 Sq Ft

  7348 Daniel Webster Dr Unit 1, Winter Park, FL 32792

  7348 Daniel Webster Dr Unit 1, Winter Park, FL 32792
• 

  

  /72

  $1,095,000

  • 4 Beds
  • 3.5 Baths
  • 2,770 Sq Ft

  2607 Lafayette Ave, Winter Park, FL 32789

  Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining.Step inside to discover an open-concept layout that seamlessly connects the kitchen,

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2607 Lafayette Ave, Winter Park, FL 32789
• 

  /2

  $535,000 Sold May 28, 2025

  • 1,945 Sq Ft
  • $275/SF
  • 35 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  4200 Bear Gully Rd, Winter Park, FL 32792

  ACCEPTING BACK-UP OFFERS.....This is the one you've been waiting for! Located in Winter Park and on OVER HALF AN ACRE this lovely home is awaiting new owners. Step inside and notice the welcoming feeling, with NEW FLOORING throughout, TALL BASEBOARDS, built ins and appealing floor plan. The eat-in kitchen has been updated to include STAINLESS APPLIANCES, GRANITE COUNTERTOPS, backsplash, BREAKFAST

  Renee Killiri RED BIRD REALTY OF FLORIDA INC

  4200 Bear Gully Rd, Winter Park, FL 32792
• 

  

  /37

  Est $185,827 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 608, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 608, Winter Park, FL 32792
• 

  

  /3

  $525,000

  • 4 Beds
  • 2 Baths
  • 1,749 Sq Ft

  3231 Lowndes Dr, Winter Park, FL 32792

  Located in beautiful Winter Park, this home's location just minutes from downtown Winter Park, Baldwin Park, along with great schools. Sitting on a large oversized corner lot, rear yard is spacious and inviting, perfect for a home garden along with space for a pool and more. The detached screened-in pad is perfect for outdoor spa, meditation or outdoor gym area. Spacious floorplan with an eat in

  Sergio Morante LA ROSA REALTY KISSIMMEE

  3231 Lowndes Dr, Winter Park, FL 32792
• 

  

  /22

  $397,500 Sold May 28, 2025

  • 1,327 Sq Ft
  • $300/SF
  • 82 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  927 Mare Bello Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. LOCATION, LOCATION! Welcome to 927 Mare Bello Drive in Winter Park, Florida's highly desirable Eastbrook neighborhood. This peaceful and family-friendly community is renowned for its quiet streets and welcoming atmosphere. TOP-RATED SCHOOLS: Families will appreciate access to excellent educational institutions, including Winter Park High School.

  Susana Moor LA ROSA REALTY KISSIMMEE

  927 Mare Bello Dr, Winter Park, FL 32792
• 

  

  /21

  Est $309,187 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft

  5752 Marble Ct, Winter Park, FL 32792

  5752 Marble Ct, Winter Park, FL 32792
• 

  

  /23

  $355,000

  • 3 Beds
  • 2.5 Baths
  • 1,448 Sq Ft

  700 Melrose Ave Unit C22, Winter Park, FL 32789

  CLICK ON VIRTUAL TOUR to get an overview of the complex.Discover a RARE opportunity to own a 3 BEDROOM 2.5 BATH unit at beautiful Winter Park Gardens. One of only seven 3 BEDROOM units so infrequently available. Enjoy stunning floor to ceiling views of lush landscaping, walking paths, pond, and the expansive 8.1-acre gardens in your tropical sunroom. Located in a vibrant 55+ community that

  Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit C22, Winter Park, FL 32789
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  /2

  $190,000 Sold May 28, 2025

  • 1,117 Sq Ft
  • $170/SF
  • 163 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1984

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792

  Reduced for a quick sell! Step into this captivating 3-bedroom, 2-bathroom second-floor end unit, nestled in a beatiful community. Spanning 1,117 square feet, this nicely upgraded home seamlessly blends style and comfort.Modern Upgrades: Enjoy a beautifully remodeled kitchen and bathrooms, featuring sleek finishes and high-quality materials.Open Concept Living: The spacious living and dining

  GOKHAN YILHAN COLDWELL BANKER RESIDENTIAL RE

  7317 Forest Hill Ct Unit 235, Winter Park, FL 32792
• 

  

  /37

  Est $1,306,902 Not Listed For Sale

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

  325 Park North Ct, Winter Park, FL 32789

  325 Park North Ct, Winter Park, FL 32789
• 

  

  /30

  $439,999

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft

  2209 Fairglenn Way, Winter Park, FL 32792

  **New roof will be installed prior to closing**Located in the sought-after Quail Run community, this 4-bedroom, 2-bathroom home offers over 2,000 sq ft of comfortable living space on an oversized lot.The heart of the home is the large kitchen, complete with two sinks—perfect for extra prep and easy cleanup. Just off the kitchen, enjoy a spacious screened-in patio, ideal for

  Benjamin Benami HIVE REALTY LLC

  2209 Fairglenn Way, Winter Park, FL 32792
• 

  /2

  $1,340,000 Sold May 28, 2025

  • 5,500 Sq Ft
  • $244/SF
  • 293 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  571 Lakefront Blvd, Winter Park, FL 32789

  Welcome to Winter Park lakefront living at its finest. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to

  Harif Hazera PREMIER SOTHEBY'S INTL. REALTY

  571 Lakefront Blvd, Winter Park, FL 32789
• 

  

  /27

  Est $473,704 Not Listed For Sale

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

  2957 Clever Ln, Winter Park, FL 32792

  2957 Clever Ln, Winter Park, FL 32792
• 

  

  /50

  $489,000

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

  2835 Bongart Rd, Winter Park, FL 32792

  Motivated Seller - 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 features fresh SOD, while the gables and

  Claudia Jenkins CHARLES RUTENBERG REALTY ORLANDO

  2835 Bongart Rd, Winter Park, FL 32792
• 

  /2

  $4,750,000 Sold May 27, 2025

  • 4,913 Sq Ft
  • $967/SF
  • 0 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1925

  984 Mayfield Ave, Winter Park, FL 32789

  Welcome home to a gated estate on one of the most desired streets in Winter Park, on a half-acre with a separate guesthouse & walk in wine cellar and tasting room, & a short distance to Park Avenue, Kraft Azalea Gardens and Winter Park Racquet Club. Timeless elegance and flawless artistry blend perfectly with modern comfort and function in this one-of-a-kind custom home originally designed for

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  984 Mayfield Ave, Winter Park, FL 32789
• 

  

  /27

  Est $454,668 Not Listed For Sale

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

  2961 Clever Ln, Winter Park, FL 32792

  2961 Clever Ln, Winter Park, FL 32792
• 

  

  /47

  $1,395,000

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

  1420 Palmer Ave, Winter Park, FL 32789

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

  Amy Turner KELLER WILLIAMS WINTER PARK

  1420 Palmer Ave, Winter Park, FL 32789
• 

  /2

  $575,000 Sold May 27, 2025

  • 972 Sq Ft
  • $592/SF
  • 24 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1952

  1230 N Denning Dr, Winter Park, FL 32789

  This charming “old Florida” bungalow in the heart of Winter Park offers the perfect blend of comfort and convenience, nestled in a prime location on a brick lined street just moments from world-class shopping and dining on famous Park Avenue. In addition, it is a short walk to both The Winter Park Village and Whole Foods. The warm and inviting interior of this home exudes character with original

  Ed Klein FANNIE HILLMAN & ASSOCIATES

  1230 N Denning Dr, Winter Park, FL 32789
• 

  

  /23

  Est $465,747 Not Listed For Sale

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

  2965 Clever Ln, Winter Park, FL 32792

  2965 Clever Ln, Winter Park, FL 32792
• 

  

  /22

  $275,000

  • 2 Beds
  • 2 Baths
  • 932 Sq Ft

  2426 Windward Way, Winter Park, FL 32792

  Nestled in the heart of the highly desirable Windward Square community, this beautifully maintained home offers the perfect blend of comfort, style, and convenience. Step inside from the tranquil front patio and be welcomed by a surprisingly spacious open floor plan that instantly feels like home.The kitchen shines with newer appliances, granite countertops and beautiful upgraded cabinetry.

  Kim Coburn RE/MAX TOWN & COUNTRY REALTY

  2426 Windward Way, Winter Park, FL 32792
• 

  /2

  $2,935,000 Sold May 27, 2025

  • 4,088 Sq Ft
  • $718/SF
  • 30 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1930

  266 Chase Ave, Winter Park, FL 32789

  One of Winter Park’s iconic and cherished homes, just a short distance from Park Avenue. On one of the most picturesque, brick-lined streets in downtown Winter Park, this extraordinary residence is a rare opportunity to own a piece of the city’s rich architectural history, fully reimagined with modern elegance and thoughtful design. On the same city block as the Alfond Inn and a two-block stroll

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  266 Chase Ave, Winter Park, FL 32789
• 

  

  /31

  Est $499,380 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,010 Sq Ft

  1564 Little Wren Ln, Winter Park, FL 32792

  1564 Little Wren Ln, Winter Park, FL 32792
• 

  

  /23

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,630 Sq Ft

  240 Cambridge Blvd, Winter Park, FL 32789

  3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking or fishing on beautiful Lake Killarney! Welcome to your new home nestled in one of Winter Park’s most desirable areas—with easy access to I-4. This beautifully maintained 3-bedroom, 2-bathroom residence offers the perfect blend of comfort, convenience, and style. Features a bright, open floor plan with

  Ashley Bennett REAL BROKER, LLC

  240 Cambridge Blvd, Winter Park, FL 32789
• 

  /2

  $685,000 Sold May 27, 2025

  • 2,446 Sq Ft
  • $280/SF
  • 53 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1321 Medinah Ct, Winter Park, FL 32792

  This incredible home has only ever had one owner! It's your opportunity to own .34 acres on a Winter Park cul-de-sac, complete with mature landscaping and backyard access to the Cady Way Trail. The oversized backyard has endless potential -- bring your ideas for a pool, an addition, or an amazing garden. Inside the home, you'll find a 4 bedroom, 2 bath split floor plan with multiple living space

  Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
• 

  

  /31

  Est $461,050 Not Listed For Sale

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

  1868 Erudite Way, Winter Park, FL 32792

  1868 Erudite Way, Winter Park, FL 32792
• 

  

  /48

  $1,499,000

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

  1327 Bridgeport Dr, Winter Park, FL 32789

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

  Jennifer Christ RE/MAX TOWN & COUNTRY REALTY

  1327 Bridgeport Dr, Winter Park, FL 32789
• 

  /2

  $660,000 Sold May 23, 2025

  • 1,975 Sq Ft
  • $334/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1962

  2732 Lion Heart Rd, Winter Park, FL 32792

  Welcome to the sought after Winter Park Pines. A neighborhood where children are always riding bikes and playing outside, neighbors look out for one another and neighborhood gatherings are a regular event. When entering the home, you find yourself drawn to the open floor plan and natural light. Beautiful, restored terrazzo floors throughout the house. The eat in kitchen with its great layout has

  Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
• 

  

  /29

  Est $440,784 Not Listed For Sale

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

  1860 Erudite Way, Winter Park, FL 32792

  1860 Erudite Way, Winter Park, FL 32792
• 

  

  /37

  $749,000

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft

  627 Darcey Dr, Winter Park, FL 32792

  Nestled in the heart of sought-after Winter Park, this beautifully updated 4-bedroom, 2-bathroom home offers 2,509 square feet of versatile living space designed for comfort, functionality, and style. Perfect for families or anyone needing room to grow, the home features multiple living areas including a formal living room with a bay window and elegant shutters, a cozy family room, a bright

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  627 Darcey Dr, Winter Park, FL 32792
• 

  /2

  $565,000 Sold May 23, 2025

  • 2,309 Sq Ft
  • $245/SF
  • 40 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  230 S Ranger Blvd, Winter Park, FL 32792

  Beautifully updated and FURNISHED (upon negotiation) 3-bedroom, 2-bath home in the desirable Winter Park Pines neighborhood is truly move-in ready! Fully renovated in 2019, the home boasts a range of high-end features, including hardwood flooring, designer fixtures, custom crown molding, and 5.25” baseboards throughout the majority of the home. Open floor plan is an inviting space for both living

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  230 S Ranger Blvd, Winter Park, FL 32792

Showing Results 641 - 680, Page 17 of 18