Winter Park, FL Homes

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  /27

  $220,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.**Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features an open living room with sliding glass doors leading to the community green space that is a tropical oasis. The adjacent

  Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  225 Lewfield Cir, Winter Park, FL 32792
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  /35

  $1,639 - $1,899 per month

  The Vista at Winter Park

  2 Beds

  4704 Lucier Ct, Winter Park, FL 32792

  Move in special- $300 on move in!*Restricted units only*Honoring Heroes: $35 Monthly Discount for Military, Police, Teachers, and Nurses!In a prime location of Winter Park, you will find our small and great community!Keeping the calm and great atmosphere, being able to relax by the lake, and being moments from shopping, dining, andmore, Set a tour today, and you will find

  4704 Lucier Ct, Winter Park, FL 32792
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  /2

  $425,000 Sold Jul 01, 2025

  • 1,032 Sq Ft
  • $412/SF
  • 112 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1950

  1550 Indiana Ave, Winter Park, FL 32789

  Discover the charm of this beautiful 3-bedroom home in the heart of Winter Park, one of the most desirable areas in Central Florida!• Bedrooms: 3 bedrooms, offering comfort and functionality. • Location: Situated on a serene street, providing the quintessential Winter Park lifestyle. • Roof: Recently replaced, ensuring long-term durability and peace of mind. •

  Ayrys Torres TALENT REALTY SOLUTIONS

  1550 Indiana Ave, Winter Park, FL 32789
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  /35

  Est $238,413 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft

  656 Saint Johns Ct Unit S, Winter Park, FL 32792

  656 Saint Johns Ct Unit S, Winter Park, FL 32792
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  /43

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  676 Dunblane Dr, Winter Park, FL 32792

  **ASSUMABLE VA LOAN at 2.25% Interest**Incredible opportunity to assume the seller’s VA mortgage at just 2.5% interest. 3 Beds | 2 Baths | Bonus Room | A meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community in Winter Park. This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full

  Emma Kaplan BALDWIN PARK REALTY LLC

  676 Dunblane Dr, Winter Park, FL 32792
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  /13

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792

  Nice house with 2 units in a great location and each unit is being rent separately. This property is located in the heart of Winter Park where everything is close by. This unit has great value and is near all of the main colleges. Come and enjoy this unit with your family and friends. Please schedule your showing today before it is gone.

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit A, Winter Park, FL 32792
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  /2

  $805,000 Sold Jul 01, 2025

  • 1,813 Sq Ft
  • $444/SF
  • 143 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1958

  1795 Walker Ave, Winter Park, FL 32789

  *** IN-LAW SUITE *** The highlight of this 95% NEW CONSTRUCTION home is the IN-LAW SUITE, perfectly positioned at the rear with a PRIVATE ENTRANCE, two bedrooms, and a full bathroom. Whether used for family, guests, or as an income-producing rental, this suite offers flexibility and added value. The in-law suite is connected to the main residence via artificial grass breezeway. This meticulously

  Tiffany Pantozzi ALIGN REAL ESTATE LLC

  1795 Walker Ave, Winter Park, FL 32789
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  /24

  Est $363,713 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,426 Sq Ft

  172 Balfour Dr Unit 2, Winter Park, FL 32792

  172 Balfour Dr Unit 2, Winter Park, FL 32792
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  /39

  $950,000

  • 4 Beds
  • 4 Baths
  • 3,646 Sq Ft

  5510 Howell Branch Rd, Winter Park, FL 32792

  Welcome to an extraordinary Florida residence, situated on a sprawling 1.52-acre lot. The main residence features an attached two-car garage, complemented by a detached two-car garage—perfect for additional vehicles or workshop space. For those in need of versatile storage or business potential, a 3,500-square-foot two-story warehouse offers ample opportunity, while a spacious outdoor

  Shaun Shaffner Blue Marlin Real Estate

  5510 Howell Branch Rd, Winter Park, FL 32792
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  /30

  $1,295 - $2,595 per month

  Signal Pointe

  1-3 Beds

  2500 Howell Branch Rd, Winter Park, FL 32792

  Come home to the lifestyle you've been dreaming of in a pet-friendly apartment home at Signal Pointe Apartment Homes near Rollins College.Offering the ideal blend of modern apartment features and elevated community amenities, these garden-style Winter Park, Florida, apartments offer the convenience you've been looking for - all within the tranquility of the suburbs. Make your move to

  2500 Howell Branch Rd, Winter Park, FL 32792
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  /2

  $593,000 Sold Jul 01, 2025

  • 2,153 Sq Ft
  • $275/SF
  • 297 Days On Market

  • 5 Beds
  • 3 Baths
  • Built 1977

  4041 Yacht Ct, Winter Park, FL 32792

  Short Sale. Great Opportunity!!! Price reduced. COMPLETELY RENOVATED, Move-in ready! WINTER PARK SCHOOLS-- ...5 Bedroom 3 bathroom home on a cul-de-sac in beautiful Lake Waunatta Woods. This stunning home offers a wide open great room/kitchen floor plan, perfect for entertaining. The beautiful updated, bright kitchen features a large island, stainless steel appliances, and quartz countertops.

  Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

  4041 Yacht Ct, Winter Park, FL 32792
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  /18

  Est $459,297 Not Listed For Sale

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

  2786 Bright Bird Ln, Winter Park, FL 32792

  2786 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /15

  $375,000

  • 3 Beds
  • 2.5 Baths
  • 1,837 Sq Ft

  2417 Passamonte Dr Unit 1E, Winter Park, FL 32792

  Location! Location! Location! Winter Park, Top Rated Florida Zone Schools, Move-In Ready, 3 Bedroom Town Home with a Garage in the VIA LAGO GATED community?? ABSOLUTELY! Meticulously maintained and spacious town home is just waiting for its new owner! Elegant brick paver driveway and entryway greet you as you pull up. The downstairs is open, light and bright. The beautifully appointed kitchen has

  Stephen Hachey FLAT FEE MLS REALTY

  2417 Passamonte Dr Unit 1E, Winter Park, FL 32792
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  /14

  $1,650 per month

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

  2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792

  Welcome to this beautifully renovated 1-bedroom, 1-bathroom first-floor condo in the highly desirable Parkview Village community. This spacious and well-maintained unit features a modern, updated kitchen and bathroom, a large walk-in closet, and an in-unit washer and dryer for your convenience. The open-concept living and dining area creates a comfortable and functional layout, perfect for

  Julian Quezada INTERINVESTMENTS REALTY, INC.

  2929 Antique Oaks Cir Unit 53, Winter Park, FL 32792
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  /2

  $325,000 Sold Jul 01, 2025

  • 1,450 Sq Ft
  • $224/SF
  • 424 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1980

  5481 Park Vale Blvd, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available at closing.Check out this stunner! This home has New Roof, Fresh Interior Paint. Windows create a light filled interior with well placed neutral accents. Step into the kitchen, complete with an eye catching stylish backsplash. Relax in your primary suite with a walk in closet included. The primary bathroom

  Karen Albright OPENDOOR BROKERAGE LLC

  5481 Park Vale Blvd, Winter Park, FL 32792
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  /29

  Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft

  7482 Canford Ct Unit 7482, Winter Park, FL 32792

  7482 Canford Ct Unit 7482, Winter Park, FL 32792
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  /26

  $219,000

  • 2 Beds
  • 1.5 Baths
  • 1,393 Sq Ft

  7466 Canford Ct Unit 25, Winter Park, FL 32792

  MOTIVATED SELLER. Welcome to this cozy and well-maintained condo with a townhome feel nestled in the desirable community of Winter Park. Offering 1,393 square feet of comfortable living space, this 2-bedroom, 1.5-bathroom home features an open-concept layout that creates a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly together, enhanced by Vinyl wood flooring

  Joseph Sipp KELLER WILLIAMS WINTER PARK

  7466 Canford Ct Unit 25, Winter Park, FL 32792
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  /35

  $1,532 - $2,902 per month

  Stonecastle Apartment Homes

  1-3 Beds

  2015 New Stonecastle Terrace, Winter Park, FL 32792

  Stonecastle Apartments is the community you've been looking for in Winter Park, FL. With spacious one-, two-, and three-bedroom homes complete with in-home washers and dryers, stainless steel appliances, and smart thermostats, you're guaranteed to find a place to live with a lifestyle to love. What's more, as a member of the community you'll also have access to our fitness center, resident

  2015 New Stonecastle Terrace, Winter Park, FL 32792
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  /2

  $540,000 Sold Jun 30, 2025

  • 2,219 Sq Ft
  • $243/SF
  • 5 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1972

  7852 Broken Arrow Trail, Winter Park, FL 32792

  Set in a quiet Winter Park cul-de-sac community, this renovated four-bedroom pool home offers an opportunity to live the Florida lifestyle you’ve been craving. Stepping inside, you’ll be struck by the versatility of its inviting, open floor plan. Flanking the foyer on either side are the living room, dining room, and a flex space, all connected by stylish luxury vinyl plank flooring. Just beyond,

  Melinda Stewart CREEGAN GROUP

  7852 Broken Arrow Trail, Winter Park, FL 32792
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  /11

  Est $458,613 Not Listed For Sale

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

  2711 Bright Bird Ln, Winter Park, FL 32792

  2711 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /72

  $825,000

  • 5 Beds
  • 3 Baths
  • 2,132 Sq Ft

  730 W Swoope Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Experience the Charm of Winter Park in This Renovated Corner HomeWelcome to the beautifully updated gem of Winter Park!Located on a prime corner lot just three short blocks from the famous Park Avenue, this stunning residence spans over 2,200 square feet and has been completely transformed to blend style, comfort, and an unbeatable

  Andres Ospina Rivera LPT REALTY, LLC

  730 W Swoope Ave, Winter Park, FL 32789
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  /30

  $2,650 per month

  • 3 Beds
  • 2 Baths
  • 1,978 Sq Ft
  • House for Rent

  2831 Lion Heart Rd Unit 1, Winter Park, FL 32792

  " A " Winter Park School District. The well-kept 3-bedroom, 2-bath home features an open floor plan and a spacious bonus storage room. The upgraded gourmet kitchen flows seamlessly into the living room, which opens to a bright and cheerful Florida room—perfect for relaxing or entertaining. Enjoy added privacy with a fully fenced yard.

  Liu Zhang JOY ESTATE ENTERPRISE INC

  2831 Lion Heart Rd Unit 1, Winter Park, FL 32792
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  /2

  $1,650,000 Sold Jun 30, 2025

  • 3,379 Sq Ft
  • $488/SF
  • 15 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 2005

  2339 Lafayette Ave, Winter Park, FL 32789

  This Beautiful Winter Park Home is located between the "Vias" and "Tree Streets" for convenient access to highly coveted schools, Interlachen Country Club, Winter Park Racquet Club, YMCA and everything you love about Winter Park. Spacious and well proportioned rooms distinguish this beautiful home through its balance of both large, open spaces for casual indoor/outdoor entertaining and more

  Skip Kirst COLLADO REAL ESTATE

  2339 Lafayette Ave, Winter Park, FL 32789
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  /27

  Est $178,437 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 759 Sq Ft

  603 Saint Johns Ct Unit S, Winter Park, FL 32792

  603 Saint Johns Ct Unit S, Winter Park, FL 32792
• 

  

  /60

  $815,000

  • 4 Beds
  • 3 Baths
  • 2,878 Sq Ft

  Unlisted Address

  Beautiful home lovingly maintained by same owners for 40+ years and looking for generational family to maintain and enjoy for another 40+ years. Spacious 1st floor with three (3) bedrooms on a split floor plan. The master bedroom is beautifully appointed with a large walk-in closet and a built-in storage rack for your jewelry or gun collection. This home is move-in ready with newer appliances,

  Stacy Morano MID-STATE PROPERTIES PSL LLC

  Unlisted Address
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  /29

  $1,652 - $2,441 per month

  Atlas at Winter Park

  1-3 Beds

  3733 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to Atlas at Winter Park!

  3733 N Goldenrod Rd, Winter Park, FL 32792
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  /2

  $470,000 Sold Jun 30, 2025

  • 1,823 Sq Ft
  • $258/SF
  • 24 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1958

  417 Carvell Dr, Winter Park, FL 32792

  Welcome to 417 Carvell Drive—where timeless mid-century modern design meets contemporary comfort. This beautifully updated 4-bedroom, 3-bathroom home sits on a spacious quarter-acre fenced lot in the heart of Winter Park.Thoughtfully designed with a split floor plan, the home features two primary bedrooms, ideal for multi-generational living or guest privacy. One of the suites includes a

  Claudia Davidson KELLER WILLIAMS WINTER PARK

  417 Carvell Dr, Winter Park, FL 32792
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  /44

  Est $596,425 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 1,937 Sq Ft

  1250 Formosa Ave, Winter Park, FL 32789

  1250 Formosa Ave, Winter Park, FL 32789
• 

  

  /19

  $207,900

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 134, Winter Park, FL 32789

  Introducing a captivating 1-bedroom, 1-bathroom condo in a prime location, granting access to the serene Lake Killarney, complete with an array of enticing features and community perks. This condo promises a cozy and convenient living experience and it is situated on the first floor. Some features include luxury vinyl throughout, decorative electric fireplace, remodeled kitchen with breakfast

  Jesus Garcia YOUR HOME SOLD GUARANTEED REAL

  2500 Lee Rd Unit 134, Winter Park, FL 32789
• 

  

  /19

  $1,800 per month

  • 3 Beds
  • 2 Baths
  • 1,072 Sq Ft
  • Apartment for Rent

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

  Discover comfort and convenience in this beautifully maintained 3-bedroom, 2-bath condo located in the heart of Orlando. This second-floor unit features a spacious open-concept layout, large bedrooms, and abundant natural light. Ideally situated near major highways, shopping centers, Orlando International Airport, and UCF, this rental is perfect for everyone! Perfect for commuters,

  Maria Lopes Camacho EMPIRE NETWORK REALTY

  1000 S Semoran Blvd Unit S, Winter Park, FL 32792
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  /2

  $217,500 Sold Jun 30, 2025

  • 913 Sq Ft
  • $238/SF
  • 35 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1967

  1250 S Denning Dr Unit 230, Winter Park, FL 32789

  Welcome to this beautifully maintained 2-bedroom, 2-bath condo in the serene community of Mead Gardens. This second-floor unit offers the ease of single-level living once inside, featuring an open-concept layout filled with natural light. The updated kitchen (2016) boasts stylish tile flooring that mimics hardwood, granite countertops, a farmhouse sink, and stainless-steel appliances, all

  Jenny Lake FANNIE HILLMAN & ASSOCIATES

  1250 S Denning Dr Unit 230, Winter Park, FL 32789
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  /44

  Est $894,417 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,513 Sq Ft

  1403 Michigan Ave, Winter Park, FL 32789

  1403 Michigan Ave, Winter Park, FL 32789
• 

  

  /38

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,887 Sq Ft

  913 Moss Ln, Winter Park, FL 32789

  ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in the heart of Winter Park, boasting 1,887 square feet of modern elegance and timeless Florida charm.

  Peter Rodriguez VECTOR PROPERTY GROUP

  913 Moss Ln, Winter Park, FL 32789
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  /35

  $1,500 - $2,750 per month

  Hannibal Square

  Studio-2 Beds

  433 W New England Ave, Winter Park, FL 32789

  We have 9 beautiful, and unique buildings located in Hannibal Square: 400, 430, 433, 444, 470 and 558 W. New England Ave., 362 S. Pennsylvania Ave. and 402 W. Welbourne Ave. Onsite parking is available in our 7 story parking garage located at 362 S. Pennsylvania Ave. There are a limited number of storage and garage spaces available as well!Our apartment options include: studio, 1/1, 2/1, 2/2,

  433 W New England Ave, Winter Park, FL 32789
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  /2

  $155,000 Sold Jun 30, 2025

  • 756 Sq Ft
  • $205/SF
  • 107 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  7266 Swallow Run, Winter Park, FL 32792

  Motivated seller willing to pay up to $3,400 towards buyers closing costs! Welcome to 7266 Swallow Run, a beautifully updated condo in Winter Park. This 2-bedroom, 2-bathroom home has been refreshed with brand-new paint, baseboards, and gorgeous new luxury vinyl floors throughout. The kitchen features stylish new cabinets, along with a brand new dishwasher and microwave. Enjoy the Florida weather

  Jessica Riccardo TRINITY REAL ESTATE SALES LLC

  7266 Swallow Run, Winter Park, FL 32792
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  /43

  Est $1,112,898 Not Listed For Sale

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

  1780 Mondrian Cir, Winter Park, FL 32789

  1780 Mondrian Cir, Winter Park, FL 32789
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  /26

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,186 Sq Ft

  1871 Staunton Ave, Winter Park, FL 32789

  Charming Bungalow on Double Lot Near Lake Killarney! Welcome to this delightful 3-bedroom, 2-bathroom bungalow nestled on a generous 0.32-acre lot—one of the largest in the neighborhood—just one block from scenic Lake Killarney. With a spacious backyard, mature landscaping and even a shuffleboard court. This property offers a rare opportunity to create your very own backyard retreat. There's

  Greg Staker WATSON REALTY CORP.

  1871 Staunton Ave, Winter Park, FL 32789
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  /28

  $3,400 per month

  • 3 Beds
  • 2 Baths
  • 1,212 Sq Ft
  • House for Rent

  1911 E Winter Park Rd, Winter Park, FL 32789

  Discover this beautifully maintained 3-bedroom, 2-bath home located in the heart of Winter Park, within the highly sought-after Audubon K-8 school zone. Situated just a short walk from vibrant Park Avenue, this property offers unparalleled access to upscale dining, boutique shopping, and scenic lakeside parks. The home combines timeless charm with modern convenience, featuring a comfortable

  Nicole Howell FANNIE HILLMAN & ASSOCIATES

  1911 E Winter Park Rd, Winter Park, FL 32789
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  /2

  $699,000 Sold Jun 30, 2025

  • 1,772 Sq Ft
  • $394/SF
  • 110 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2025

  1632 Haven Dr, Orlando, FL 32803

  Welcome to your dream home in vibrant Wadeview Park! This exquisite new construction townhome by David Weekley Homes offers modern living with a touch of elegance, boasting 1,772 square feet of thoughtfully designed space. Perfect for families and professionals alike, this residence features 3 Spacious Bedrooms: Enjoy restful retreats in generously sized bedrooms, each designed with comfort and

  Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
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  /18

  Est $449,710 Not Listed For Sale

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

  2809 Bright Bird Ln, Winter Park, FL 32792

  2809 Bright Bird Ln, Winter Park, FL 32792

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