Winter Park, FL Homes

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  $5,250,000

  • 5 Beds
  • 5.5 Baths
  • 5,164 Sq Ft

  1221 Richmond Rd, Winter Park, FL 32789

  Now offered with a significant price improvement, this award-winning custom residence presents a rare opportunity in Winter Park’s sought-after Virginia Heights neighborhood, prized for its proximity to Park Avenue, placement within an A-rated school district, and deeded access to the Winter Park Chain of Lakes. Created by an award-winning builder as a personal family residence, this home

  Audra Wilks PREMIER SOTHEBY'S INTL. REALTY

  1221 Richmond Rd, Winter Park, FL 32789
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  /20

  $3,229 per month

  • 3 Beds
  • 2 Baths
  • 990 Sq Ft
  • Condo for Rent

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789

  Experience a cozy tiny-home retreat in Winter Park, a quiet neighborhood just 10 minutes from downtown Orlando and 20 minutes from Disney’s parks. Feel at home in this 4-bedroom, 2-bath home that sleeps 8.Every corner is designed for comfort, from the queen-size beds to the fully equipped kitchen with stainless steel appliances and a Keurig coffee machine. The home also features an outdoor

  2007 Cornell Ave Unit ID1032296P, Winter Park, FL 32789
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  $799,000 Sold Apr 30, 2025

  2320 Janice Ave, Winter Park, FL 32789

  • Land
  • 0.28 Acre
  • $2,853,571 per Acre

  Last Sold Summary

  • 2 Days On Market

  Current Estimated Value $807,333

  Last Listing Agent Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2320 Janice Ave, Winter Park, FL 32789
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  /2

  Est $149,964 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  160 Lewfield Cir Unit 160, Winter Park, FL 32792

  160 Lewfield Cir Unit 160, Winter Park, FL 32792
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  /86

  $3,895,000 Pending

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft

  637 N Park Ave, Winter Park, FL 32789

  A refined, custom brownstone with an exclusive Park Avenue address, offering an unparalleled Winter Park lifestyle enhanced by the finest designer selections throughout. The timeless brick elevation and expansive windows evoke the charm of a favorite city street while preserving the tranquility of this sought-after setting. This three-story townhouse offers 4,237 square feet of thoughtfully

  Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  637 N Park Ave, Winter Park, FL 32789
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  /24

  $1,695 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C216, Winter Park, FL 32789

  Available for immediate move-in, this comfortable second-floor corner condo offers a peaceful setting with playground and pool views. The home features a fully carpeted interior, a spacious kitchen with a pantry closet, and a newer refrigerator. Washer and dryer are included for added convenience. Great balcony for relaxing on the cooler Florida days! Located in desirable Winter Park, you'll

  Yarmmys Vargas ZEN LIVING HOMES LLC

  1695 Lee Rd Unit C216, Winter Park, FL 32789
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  /2

  $235,000 Sold Apr 29, 2025

  2529 Leeward Way, Winter Park, FL 32792

  • 2 Beds
  • 1 Bath
  • 912 Sq Ft
  • Built 1977

  Last Sold Summary

  • $258/SF
  • 26 Days On Market

  Current Estimated Value $238,511

  Last Listing Agent Chris Creegan CREEGAN GROUP

  2529 Leeward Way, Winter Park, FL 32792
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  /2

  Est $441,085 Not Listed For Sale

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

  2953 Clever Ln, Winter Park, FL 32792

  2953 Clever Ln, Winter Park, FL 32792
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  /26

  $197,500 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792

  Under contract-accepting backup offers. Ideally situated just minutes from Full Sail University, UCF, and major retailers, this well-appointed 2-bedroom, 2.5-bath townhome-style condo offers both comfort and convenience. No rear neighbors. The main floor features a spacious living and dining area with a breakfast nook, a guest half bath, and updated appliances. Upstairs, you’ll find two

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
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  $3,000 per month

  • 3 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  4044 Tenita Dr, Winter Park, FL 32792

  Welcome to this beautiful and cozy single-story home with a pool, designed to captivate your senses from the moment you step inside. This thoughtfully laid-out residence offers a spacious living area, dining space, and an open-concept kitchen—the true heart of the home. Featuring elegant cascading quartz countertops, modern white and blue cabinetry, and stainless steel appliances, the kitchen is

  4044 Tenita Dr, Winter Park, FL 32792
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  /2

  $423,000 Sold Aug 07, 2025

  2812 Bright Bird Ln, Winter Park, FL 32792

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

  Last Sold Summary

  • 8% Below List Price
  • $222/SF
  • 87 Days On Market

  Current Estimated Value $425,488

  Last Listing Agent Jessica Snyder LPT REALTY, LLC

  2812 Bright Bird Ln, Winter Park, FL 32792
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  /18

  Est $188,523 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 990 Sq Ft

  3351 River View Way Unit 41, Winter Park, FL 32792

  3351 River View Way Unit 41, Winter Park, FL 32792
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  /28

  $445,000

  • 5 Beds
  • 3 Baths
  • 1,945 Sq Ft

  3642 Periwinkle Dr, Winter Park, FL 32792

  Rare opportunity in a quiet Winter Park neighborhood! This oasis home offers nearly 2,000 sq ft of living space PLUS a fully equipped studio apartment with private entrance, kitchenette, full bath, fireplace, separate A/C, and generous storage—ideal for guests, multi-generational living, or rental income. The main home features a freshly painted interior and exterior, new LVP flooring throughout,

  John Hwangbo HONEST REAL ESTATE COMPANY

  3642 Periwinkle Dr, Winter Park, FL 32792
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  /14

  $1,420 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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  $760,000 Sold Jul 17, 2025

  2159 Marsh Sedge Ln, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $347/SF
  • 42 Days On Market

  Current Estimated Value $755,314

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2159 Marsh Sedge Ln, Winter Park, FL 32792
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  /42

  Est $471,851 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,376 Sq Ft

  2444 Firstlight Way, Winter Park, FL 32792

  2444 Firstlight Way, Winter Park, FL 32792
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  /18

  $489,000

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

  1422 Tierra Cir, Winter Park, FL 32792

  PRICE IMPROVEMENT! INCREDIBLE OPPORTUNITY! 5.75% ASSUMABLE MORTGAGE Interest Rate Available, making it an excellent opportunity for qualified Buyers. Welcome to 1422 Tierra Circle, beautifully refreshed immaculate pool home located in the well-established community of Casa Aloma, featuring 4 bedrooms, 2 full bathrooms and open floor plan. You will notice the enhanced curb appeal from the moment

  Jennifer Conrado CHARLES RUTENBERG REALTY ORLANDO

  1422 Tierra Cir, Winter Park, FL 32792
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  /15

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft
  • House for Rent

  3221 Thistle Hill Dr, Aloma, FL 32792

  This home is exclusively offered by Brandywine Homes USA on a first-come, first-approved basis until the lease is signed and the security deposit is paid. Rental Qualifications: Rental Fees: Security Deposit: Varies based on credit, with a standard deposit equal to 1 month's rent. Security Deposit Alternatives available - $150 fee (subject to approval).

  3221 Thistle Hill Dr, Aloma, FL 32792
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  $450,000 Sold Jul 22, 2025

  1624 Little Wren Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 23 Days On Market

  Current Estimated Value $457,227

  Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1624 Little Wren Ln, Winter Park, FL 32792
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  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 600 Sq Ft

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

  3069 Aaron Burr Ave Unit D, Winter Park, FL 32792
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  /55

  $1,500,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft

  1144 Wading Waters Cir, Winter Park, FL 32792

  Set within the exclusive Winter Park community of Waters Edge at Hawks Crest, this stunning Kerrville II Meritage model offers refined luxury living on a premium lot boasting serene pond views. Thoughtfully designed for both elegant entertaining and everyday comfort, the open-concept layout is filled with natural light and showcases high-end finishes and upgrades throughout this 5 bedroom 4 1⁄2

  Maria Huff PORCH LIGHT REALTY, LLC.

  1144 Wading Waters Cir, Winter Park, FL 32792
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  /22

  $1,750 per month

  • 3 Beds
  • 2 Baths
  • 1,020 Sq Ft
  • Townhouse for Rent

  2552 Gold Ct, Winter Park, FL 32792

  Welcome to 2552 Gold Court – Your Perfect Winter Park Rental Home!Discover comfortable living in this beautifully renovated 3-bedroom, 2-bath duplex offering approximately 1,020 square feet of thoughtfully designed space. This move-in ready home combines modern updates with practical amenities to create the ideal rental experience.This charming residence features a bright, open floor plan

  Kelly Price KELLY PRICE & COMPANY LLC

  2552 Gold Ct, Winter Park, FL 32792
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  /2

  $432,000 Sold May 08, 2025

  2472 Firstlight Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Below List Price
  • $208/SF
  • 53 Days On Market

  Current Estimated Value $444,256

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  2472 Firstlight Way, Winter Park, FL 32792
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  /2

  Est $212,662 Not Listed For Sale

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3610, Winter Park, FL 32792
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  /16

  $155,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792

  Investors and Owner Occupied Welcome! Investors start your portfolio of properties with monthly income today. Now's your chance! This apartment is suited for anyone tired of paying rent and want to become a homeowner. Look no further. This unit is exceptionally located in a great community. Prime Location and Zip Code are key! Low HOA! with minimal stress. Welcome home to 3019 Antique Oaks Circle

  Kelly Flores COLDWELL BANKER REALTY

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
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  /11

  $1,380 per month

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

  2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792

  Property Id: 1010517Second Floor one bedroom unit in the highly desirable Parkview Condominium Complex across from Full Sail University. The rent includes water and sewer. All floors are laminate.

  2942 Antique Oaks Cir Unit 82, Winter Park, FL 32792
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  $605,000 Sold Dec 22, 2025

  2478 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 2,256 Sq Ft
  • Built 1965

  Last Sold Summary

  • 19% Below List Price
  • $268/SF
  • 123 Days On Market

  Last Listing Agent Erica Magtira LPT REALTY, LLC

  2478 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $407,401 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  620 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /67

  $12,900,000 Pending

  • 6 Beds
  • 9 Baths
  • 12,190 Sq Ft

  2203 Via Tuscany, Winter Park, FL 32789

  Under contract-accepting backup offers. Elegant Mediterranean estate, masterfully crafted by Akers Custom Homes and set within the heart of the Vias. Privately tucked behind a gated drive, the approach unfolds to a grand circular motor court framed by lush, manicured grounds spanning over two acres with impressive sunset views across Lake Maitland. Every element of the estate is thoughtfully

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2203 Via Tuscany, Winter Park, FL 32789
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  /23

  $2,195 per month

  • 2 Beds
  • 2 Baths
  • 1,408 Sq Ft
  • House for Rent

  3007 Ash Park Point, Winter Park, FL 32792

  Beautiful 2BR/2BA home in highly sought-after Winter Park, available immediately. This well-maintained home offers an open and inviting floor plan with abundant natural light, spacious living and dining areas, and a functional kitchen with ample storage. Both bedrooms are generously sized, each with its own full bathroom, providing comfort and privacy for residents. Property features include a

  Todd Norwood BESPOKE REAL ESTATE

  3007 Ash Park Point, Winter Park, FL 32792
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  $417,100 Sold Nov 24, 2025

  690 Osceola Ave Unit 502, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1969

  Last Sold Summary

  • 26% Below List Price
  • $298/SF
  • 196 Days On Market

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO

  690 Osceola Ave Unit 502, Winter Park, FL 32789
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  /2

  Est $561,233 Not Listed For Sale

  • 18 Beds
  • 18 Baths
  • 1,852 Sq Ft

  875 Miles Ave Unit 4, Winter Park, FL 32789

  875 Miles Ave Unit 4, Winter Park, FL 32789
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  /11

  $630,000

  • Land
  • 0.31 Acre
  • $2,032,258 per Acre

  1860 Staunton Ave, Winter Park, FL 32789

  Large double lot in the highly desirable Killarney Shores neighborhood of Winter Park. The property has already received county approval to revert to the original platting, subdivide into two 50' x 135' lots. Located just one block from Lake Killarney. This prime location is minutes from Park Avenue, College Park, and I-4, providing both convenience and long-term value. A rare opportunity to

  Leighton Hope COMPASS FLORIDA LLC

  1860 Staunton Ave, Winter Park, FL 32789
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  /18

  $2,625 per month

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft
  • House for Rent

  6877 Jackman Blvd, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2769.90. That covers your base rent, $2625.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  6877 Jackman Blvd, Winter Park, FL 32792
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  $1,640,000 Sold Mar 06, 2025

  508 W Swoope Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,133 Sq Ft
  • Built 2021

  Last Sold Summary

  • 17% Below List Price
  • $397/SF
  • 258 Days On Market

  Last Listing Agent Whitney Johnson COLDWELL BANKER RESIDENTIAL RE

  508 W Swoope Ave, Winter Park, FL 32789
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  /2

  Est $430,237 Not Listed For Sale

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

  2931 Clever Ln, Winter Park, FL 32792

  2931 Clever Ln, Winter Park, FL 32792
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  /14

  $390,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,517 Sq Ft

  5547 Garden Grove Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Discover a delightful pool home nestled in the heart of vibrant Winter Park, where you can enjoy the freedom of no HOA. Sunlight pours into every room, creating a warm and inviting atmosphere ideal for first-time buyers or families seeking a lovingly maintained, move-in-ready retreat. The kitchen features sleek granite countertops, abundant cabinetry, and

  Steve Dalton ROYALTY R E BOUTIQUE INC

  5547 Garden Grove Cir, Winter Park, FL 32792
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  /20

  $3,600 per month

  • 2 Beds
  • 2 Baths
  • 1,393 Sq Ft
  • House for Rent

  220 Overlook Rd, Winter Park, FL 32789

  Charming Cape Cod–style home available for lease in the heart of Winter Park. Ideally located just one block from Lake Mizell and moments from Park Avenue and Rollins College, this residence offers an exceptional lifestyle surrounded by premier shops, dining, and local amenities.The home features a spacious and inviting floor plan with a large living room, sunroom or dining area, and two

  Julie Bombardo PREMIER SOTHEBY'S INTL. REALTY

  220 Overlook Rd, Winter Park, FL 32789
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  $380,000 Sold Feb 27, 2025

  3505 Balsam Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,709 Sq Ft
  • Built 1965

  Last Sold Summary

  • 9% Above List Price
  • $222/SF
  • 21 Days On Market

  Current Estimated Value $376,264

  Last Listing Agent Jennifer Clark GLORY INTL. REAL ESTATE CO

  3505 Balsam Dr, Winter Park, FL 32792
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  /2

  Est $442,517 Not Listed For Sale

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

  2939 Clever Ln, Winter Park, FL 32792

  2939 Clever Ln, Winter Park, FL 32792

Showing Results 441 - 480, Page 12 of 18