Winter Park, FL Homes

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  /65

  $2,399,000 Pending

  • 4 Beds
  • 5 Baths
  • 5,051 Sq Ft

  2550 Venetian Way, Winter Park, FL 32789

  Chain of Lakes Water- Front Home with Private Boat Dock, Winter Park Luxury Living. Step into your future with this extraordinary custom built residence, inspired by the artistic richness of Fernando Botero. From your back lanai, step directly onto your private, custom boat dock featuring a covered, remote-operated boat lift, and cruise the Venetian Canal with direct access to WinterPark’s

  Felicia Donateli PALM PROPERTIES OF CF, INC.

  2550 Venetian Way, Winter Park, FL 32789
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  /13

  $1,575 Per Month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Condo for Rent

  2911 Antique Oaks Cir Unit 12, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Beautifully Remodeled 2 Bed / 2 Bath Condo – Second Floor | Prime Location Charming and fully remodeled second-floor condo located just steps from the pool. Perfect for those seeking a low-maintenance lifestyle. This bright and inviting unit features fresh paint, new wood and ceramic tile flooring, and updated bathrooms and kitchen with granite

  Clara Herrera CLARA HERRERA REALTY

  2911 Antique Oaks Cir Unit 12, Winter Park, FL 32792
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  $375,000 Sold Mar 06, 2026

  1007 Early Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,721 Sq Ft
  • Built 1956

  Last Sold Summary

  • 12% Below List Price
  • $218/SF
  • 101 Days On Market

  Current Estimated Value $375,959

  Last Listing Agent Eric Gross EXP REALTY LLC

  1007 Early Ave, Winter Park, FL 32789
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  /18

  Est $431,408 Not Listed For Sale

  2809 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2809 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $232/SF
  • 29 Days On Market

  • Last Sold Price $442,190
  • Jun 13, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  $159,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  262 Lewfield Cir Unit 262, Winter Park, FL 32792

  Walk into this freshly painted, pool view unit. Updates include new vinyl plank flooring throughout, new lighting, window coverings and a new tub/shower fixtures in the bathroom! Residents enjoy access to two pools, lighted tennis courts, fitness center, car care facilities and a clubhouse. The clubhouse can be rented for hosted gatherings. There is a free on-site laundry facility. Location is

  Drew Bishop KELLER WILLIAMS REALTY FT MYER

  262 Lewfield Cir Unit 262, Winter Park, FL 32792
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  /19

  $1,250 Per Month

  • 1 Bed
  • 1 Bath
  • Townhouse for Rent

  138 Lewfield Cir, Winter Park, FL 32792

  Charming 1-Bedroom Condo in the Heart of Winter Park!Welcome to 138 Lewfield Cir – a beautifully maintained 1-bedroom, 1-bath second-floor condo offering 678 sq ft of comfortable living in the desirable Lake Howell community. From the moment you walk in, you'll feel right at home with a spacious open layout, well-sized bedroom, and a cozy living area that opens up to a private balcony

  138 Lewfield Cir, Winter Park, FL 32792
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  $434,000 Sold Sep 12, 2025

  1122 Washington Ave Unit 7, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,556 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Above List Price
  • $279/SF
  • 55 Days On Market

  Current Estimated Value $462,691

  Last Listing Agent Raul Veitia BELMONT REALTY

  1122 Washington Ave Unit 7, Winter Park, FL 32789
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  /18

  Est $429,341 Not Listed For Sale

  2805 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  2805 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $227/SF
  • 6 Days On Market

  • Last Sold Price $433,390
  • Jun 14, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /25

  $250,000

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

  7484 Canford Ct Unit 8, Winter Park, FL 32792

  This three-bedroom, three-bath updated Winter Park townhome-style condo is located in a quiet complex, a perfect place to call home. It's just minutes away from the University of Central Florida, Full Sail University, & Valencia College. This location makes an excellent investment for a college (or parents of) student. The upgraded kitchen has granite countertops with a custom sink, newer

  Greg Harrison CHARLES RUTENBERG REALTY ORLANDO

  7484 Canford Ct Unit 8, Winter Park, FL 32792
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  /41

  $4,150 Per Month

  • 4 Beds
  • 3 Baths
  • 2,288 Sq Ft
  • House for Rent

  1711 Chestnut Ave, Winter Park, FL 32789

  Welcome home to the heart of Winter Park's coveted Tree Streets. This beautifully remodeled single-family home sits on an oversized lot just moments from Interlachen Country Club and Winter Park Racquet Club, and is zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. Inside, natural light pours through windows in every room, giving the home a bright, airy feel throughout.

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  1711 Chestnut Ave, Winter Park, FL 32789
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  $850,000 Sold Mar 25, 2026

  465 N Phelps Ave, Winter Park, FL 32789

  • Land
  • 11,761 Sq Ft
  • $3,148,148 per Acre

  Last Sold Summary

  • 7 Days On Market

  Current Estimated Value $1,017,024

  Last Listing Agent Hircanys Vicioso FIDICITY REALTY INC

  465 N Phelps Ave, Winter Park, FL 32789
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  /18

  Est $439,051 Not Listed For Sale

  2821 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2821 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $263/SF
  • 49 Days On Market

  • Last Sold Price $468,490
  • Jun 14, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  $435,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,576 Sq Ft

  7445 Betty St, Winter Park, FL 32792

  Under contract-accepting backup offers. Newly remodeled ranch in a prime location! Situated in a great neighborhood with easy access to everything, this move-in ready home checks all the boxes. Featuring a desirable split floor plan, this home offers both functionality and privacy. Inside, you’ll find brand new windows, beautiful new wood flooring, and new carpet in the guest bedrooms, along with

  Nicholas Macy LISTY, LLC

  7445 Betty St, Winter Park, FL 32792
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  /7

  $1,600 Per Month

  • 2 Beds
  • 2 Baths
  • 967 Sq Ft
  • 1/2 Duplex in Winter Park

  3012 Patel Dr, Winter Park, FL 32792

  Nice two bedroom, two bath home with spacious kitchen and living area. House is tiled throughout. Driveway accommodates 2 cars. Fenced in backyard with small shed. Close to Target, Costco Publix, Aldi. Winter Park Schools.

  3012 Patel Dr, Winter Park, FL 32792
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  $505,000 Sold Aug 01, 2025

  715 Roughbeard Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,250 Sq Ft
  • Built 1968

  Last Sold Summary

  • 12% Below List Price
  • $224/SF
  • 60 Days On Market

  Current Estimated Value $544,086

  Last Listing Agent Christine Gerardi NEXTHOME DIAMOND PROPERTIES

  715 Roughbeard Rd, Winter Park, FL 32792
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  /18

  Est $445,633 Not Listed For Sale

  2796 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2796 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 78 Days On Market

  • Last Sold Price $474,590
  • May 22, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /25

  $105,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft

  3028 George Mason Ave Unit 7, Winter Park, FL 32792

  Priced to sell and move-in ready TODAY. This completely updated 2-bedroom, 2-bathroom, 1,088 sq ft ground-floor condo in the heart of Winter Park is the opportunity buyers and investors have been waiting for. At $105,000 (special assesment to-be-paid by buyer) in the 32792 zip code, it will not last.Step inside to brand-new marble-look porcelain tile flowing through every room, no carpet

  Alex Khalil EXP REALTY LLC

  3028 George Mason Ave Unit 7, Winter Park, FL 32792
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  /19

  $1,450 Per Month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

  Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

  Praveen Setty RIGHTHOUSE REALTY LLC

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
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  $252,500 Sold Jul 17, 2025

  2309 Sun Valley Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,669 Sq Ft
  • Built 1985

  Last Sold Summary

  • 11% Below List Price
  • $151/SF
  • 65 Days On Market

  Current Estimated Value $251,455

  Last Listing Agent Kristin Vogt PLLC KGV REALTY GROUP

  2309 Sun Valley Cir, Winter Park, FL 32792
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  /88

  Est $1,910,234 Not Listed For Sale

  1661 Hillcrest Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,161 Sq Ft
  • Built 2017

  1661 Hillcrest Ave, Winter Park, FL 32789

  Last Sold Summary

  • 6% Above List Price
  • $569/SF
  • 21 Days On Market

  • Last Sold Price $1,800,000
  • Apr 18, 2024

  Last Listing Agent Domenique Lombardo ROYALTY R E BOUTIQUE INC
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  /82

  $149,990

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft

  1695 Lee Rd Unit E215, Winter Park, FL 32789

  Located in the heart of Winter Park, this charming condo stands ready to welcome you home. This three-bedroom, two-bathroom sanctuary offers a blend of comfort and modern elegance, perfect for those who cherish both relaxation and entertaining. As you step inside, the spacious living and dining areas greet you with an abundance of natural light, creating a warm and inviting atmosphere. Imagine

  Jenaia Fowlkes FOWLKES REALTY CO

  1695 Lee Rd Unit E215, Winter Park, FL 32789
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  /16

  $1,700 Per Month

  • 2 Beds
  • 2 Baths
  • 1,059 Sq Ft
  • Excellent location

  4968 Tangerine Ave Unit 4968, Winter Park, FL 32792

  This roomy condo is available for immediate occupancy. New Luxury Vinyl Plank floors just installed. The unit is ideally located in Winter Park, not far from Full Sail or UCF. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet community with plenty of privacy. Amenities include a pool and workout room. Call today for your private tour of this amazing

  4968 Tangerine Ave Unit 4968, Winter Park, FL 32792
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  $268,000 Sold Feb 24, 2026

  609 Gallery Dr Unit 204, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 893 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $300/SF
  • 99 Days On Market

  Current Estimated Value $259,308

  Last Listing Agent Olga Ray A2Z REALTY GROUP

  609 Gallery Dr Unit 204, Winter Park, FL 32792
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  /2

  Est $447,803 Not Listed For Sale

  2719 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,780 Sq Ft
  • Built 2024

  2719 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 9% Above List Price
  • $230/SF

  • Last Sold Price $408,990
  • Jan 31, 2024

  Last Listing Agent Denise Del Castillo LPT REALTY, LLC
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  /2

  $445,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,647 Sq Ft

  3720 Jonquil Ln, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom home nestled in a sought after community that offers both charm and convenience. From the moment you arrive, you’ll notice the care and attention that has gone into every detail of this property. You will immediately appreciate the meticulous maintenance this home has enjoyed. Step outside to your private backyard oasis, where a stunning pool and

  Nicholas Kovats KELLER WILLIAMS ADVANTAGE REALTY

  3720 Jonquil Ln, Winter Park, FL 32792
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  /14

  $1,360 Per Month

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft
  • Condo for Rent

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

  This is a 2 bedroom, 2 bathroom, second floor condo in the Lancelot at Winter Park community near local shops, restaurants, and schools. Features include a spacious main living area, a lovely kitchen, vaulted ceilings, spacious bedrooms, and a laundry closet. Community amenities include a pool, gym, and clubhouse. Schedule a showing or submit an application online. All Real Property Management &

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
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  $468,000 Sold Aug 28, 2025

  541 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,899 Sq Ft
  • Built 1965

  Last Sold Summary

  • $246/SF
  • 8 Days On Market

  Current Estimated Value $489,638

  Last Listing Agent Christopher Bauman REVEL REALTY LLC

  541 London Rd, Winter Park, FL 32792
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  /18

  Est $437,830 Not Listed For Sale

  2790 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2790 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $261/SF
  • 19 Days On Market

  • Last Sold Price $465,790
  • Mar 21, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /43

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft

  1468 Auburn Green Loop, Winter Park, FL 32792

  Welcome to this fantastic home on beautiful Lake Florence in a great Winter Park location off of Howell Branch Road in Seminole County! This spacious 3-Bedroom, 2-Bathroom house features vaulted ceilings, wood burning fireplace, ceiling fans, and wonderful outdoor areas. The Living Room, Dining Room and Great Room make this home feel large. The main living areas, hallways and one bedroom have

  Jodie Ma COLDWELL BANKER VANGUARD EDGE

  1468 Auburn Green Loop, Winter Park, FL 32792
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  /16

  $1,775 Per Month

  • 2 Beds
  • 2 Baths
  • 964 Sq Ft
  • Townhouse for Rent

  3254 Howell Branch Rd, Winter Park, FL 32792

  This charming 2-bedroom, 2-bath duplex is ready for immediate move-in, offering a warm and inviting atmosphere for comfortable living. Step inside to discover a thoughtfully designed space with tile flooring throughout, providing both durability and easy maintenance. The heart of the home is the well-appointed kitchen, featuring stainless steel appliances and solid-surface countertops. This

  Carissa Lawhun FLORIDA REALTY INVESTMENTS

  3254 Howell Branch Rd, Winter Park, FL 32792
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  $710,000 Sold Apr 01, 2026

  630 Saint Dunstan Way, Winter Park, FL 32792

  • 5 Beds
  • 2 Baths
  • 2,240 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Above List Price
  • $317/SF
  • 5 Days On Market

  Current Estimated Value $670,569

  Last Listing Agent Melissa Johnson EXP REALTY LLC

  630 Saint Dunstan Way, Winter Park, FL 32792
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  Est $834,235 Not Listed For Sale

  1770 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2023

  1770 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $376/SF
  • 18 Days On Market

  • Last Sold Price $825,000
  • Mar 18, 2024

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /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
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  /41

  $2,600 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,837 Sq Ft
  • Condo for Rent

  2530 Passamonte Dr Unit 10E, Winter Park, FL 32792

  REMODELLED - new flooring and freshly painted. Welcome home to this beautiful townhome centrally located in Winter Park, 15 miles away from Park Avenue, just outside of Baldwin Park. Enjoy beautiful water views on the back patio. This home is fresh ready to move in. Available for rent April 15 or later. Top schools, Glenridge middle school, Winter Park high school and Brookshire elementary

  Livia Petraru EXP REALTY LLC

  2530 Passamonte Dr Unit 10E, Winter Park, FL 32792
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  $360,000 Sold Mar 27, 2026

  7213 Silver Place, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,252 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $288/SF
  • 3 Days On Market

  Current Estimated Value $367,800

  Last Listing Agent Michael Rogers INNOVATIVE REALTY, LLC

  7213 Silver Place, Winter Park, FL 32792
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  Not Listed For Sale

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6169911, Winter Park, FL 32792

  Last Sold Summary

  • 73 Days On Market

  • Last Sold Price $630,000
  • May 09, 2024

  Last Listing Agent Rick Cole KELLER WILLIAMS WINTER PARK
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  $1,695,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,031 Sq Ft

  629 Country Club Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. Newly built in the heart of Winter Park, this warm modern-industrial residence offers 4 bedrooms, 3.5 baths and 3,031 heated square feet of thoughtfully designed living space (3,674 total including a two-car garage). Soaring 12’8” ceilings downstairs and 10’ ceilings upstairs create volume and light throughout. Oversized black grid windows flood the home

  Randy Lazarus CLASSIC HOMES

  629 Country Club Dr, Winter Park, FL 32789
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  /30

  $2,100 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,279 Sq Ft
  • House for Rent

  2846 Euston Rd, Winter Park, FL 32789

  Special of the month! $2100 for the first 2 months then $2350. Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes from I4, close to Park Avenue District, College Park, major shopping centers and

  Vanessa Laboy 365 REALTY, INC.

  2846 Euston Rd, Winter Park, FL 32789
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  $935,000 Sold Dec 19, 2025

  7706 Waunatta Ct, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 3,858 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $242/SF
  • 70 Days On Market

  Current Estimated Value $1,002,755

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  7706 Waunatta Ct, Winter Park, FL 32792
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  /2

  Est $108,913 Not Listed For Sale

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 786 Sq Ft
  • Built 1974

  7453 Daniel Webster Dr Unit D, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $134/SF
  • 4 Days On Market

  • Last Sold Price $105,000
  • Jul 25, 2024

  Last Listing Agent Rizwan Rashid MNT INTERNATIONAL

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