Winter Park, FL Homes

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  $285,000

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft

  5143 Lazy Oaks Dr, Winter Park, FL 32792

  Quiet Living in the Desirable Lazy Oaks Community of Winter Park. Welcome to the peaceful, well-established community of Lazy Oaks in highly sought-after Winter Park. This hidden gem offers beautifully landscaped grounds, meticulous maintenance, and the added benefit of a low HOA.This lovingly maintained 2-bedroom, 2-bath home features a spacious, thoughtfully designed floor plan with an

  Mindy Machock KELLER WILLIAMS REALTY AT THE PARKS

  5143 Lazy Oaks Dr, Winter Park, FL 32792
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  $4,000 Per Month

  • 4 Beds
  • 2 Baths
  • 1,548 Sq Ft
  • House for Rent

  1815 Barker Dr, Winter Park, FL 32789

  Furnished turn-key luxury lake-view home in Winter Park where comfort meets style. This beautifully designed 4-bedroom / 2-bath one story home features an open-concept layout, curated artwork, lush front and backyard spaces, a wood deck, and an outdoor kitchen perfect for entertaining. Ideally located just minutes from Orlando's top attractions, hospitals, airports, Winter Park's cultural gems,

  Benjamin Cole, IV SOTERA LIVING

  1815 Barker Dr, Winter Park, FL 32789
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  $660,000 Sold May 23, 2025

  2732 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 1962

  Last Sold Summary

  • $334/SF
  • 2 Days On Market

  Current Estimated Value $648,234

  Last Listing Agent Sue Grafton FANNIE HILLMAN & ASSOCIATES

  2732 Lion Heart Rd, Winter Park, FL 32792
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  Est $436,516 Not Listed For Sale

  2931 Clever Ln, Winter Park, FL 32792

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

  2931 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $235/SF
  • 32 Days On Market

  • Last Sold Price $448,190
  • Aug 16, 2024

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  $429,000

  • 4 Beds
  • 2 Baths
  • 1,836 Sq Ft

  1842 Puritan Ave, Winter Park, FL 32792

  Modern design , open concept layout , sleek quartz counter top , all new appliances, new luxury vinyl plank flooring, new lanai upgrade. This beautiful 4 bedroom and 2 full bath is situated on a 8,250 square feet lot, which was newly fenced in 2024 which gives a sense of privacy and spaciousness. As you exit the interior through the French door into the lanai . There is two detached shed for your

  Karan Jodha MOBED REALTY, P.A

  1842 Puritan Ave, Winter Park, FL 32792
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  /21

  $1,200 Per Month

  • 1 Bed
  • 1 Bath
  • 537 Sq Ft
  • One bedroom apt 7 or 12 months furnish or unfurnished. Apartamento disponible amueblado o sin mue...

  3075 Aaron Burr Ave, Winter Park, FL 32792

  Centrally located in Winter Park near Full Sail University, and check out this cute move-in ready, 1 Bed/1 Bath second-floor condo with a rear balcony. All tiled flooring, new paint, new toilets and light fixtures, new dishwasher and range. The community features a large swimming pool and a coined laundry room inside a community multipurpose room. This location is zoned for A-rated schools and

  3075 Aaron Burr Ave, Winter Park, FL 32792
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  $685,000 Sold May 27, 2025

  1321 Medinah Ct, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,446 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $280/SF
  • 53 Days On Market

  Current Estimated Value $695,619

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY

  1321 Medinah Ct, Winter Park, FL 32792
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  Est $447,105 Not Listed For Sale

  2939 Clever Ln, Winter Park, FL 32792

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

  2939 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 6% Below List Price
  • $268/SF
  • 8 Days On Market

  • Last Sold Price $477,890
  • Aug 16, 2024

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC
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  $2,265,000

  • 5 Beds
  • 3.5 Baths
  • 3,691 Sq Ft

  1885 Temple Dr, Winter Park, FL 32789

  Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich

  Jennifer Sloan COMPASS FLORIDA LLC

  1885 Temple Dr, Winter Park, FL 32789
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  /17

  $1,650 Per Month

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

  1000 S Semoran Blvd Unit 815, Winter Park, FL 32792

  This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home

  Scott Butts KIMBRIDGE REALTY, LLC

  1000 S Semoran Blvd Unit 815, Winter Park, FL 32792
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  $637,500 Sold Jan 16, 2026

  595 Huntington Ave Unit 4, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,951 Sq Ft
  • Built 1987

  Last Sold Summary

  • 6% Below List Price
  • $327/SF
  • 149 Days On Market

  Current Estimated Value $634,639

  Last Listing Agent Andrew Livingston COLDWELL BANKER REALTY

  595 Huntington Ave Unit 4, Winter Park, FL 32789
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  Not Listed For Sale

  3065 George Mason Ave Unit B, Winter Park, FL 32792

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

  3065 George Mason Ave Unit B, Winter Park, FL 32792

  Last Sold Summary

  • $190/SF
  • 168 Days On Market

  • Last Sold Price $100,000
  • Oct 25, 2024

  Last Listing Agent Jacki Sandler SANDLER MANAGEMENT INC
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  $439,000

  • 3 Beds
  • 2 Baths
  • 1,405 Sq Ft

  2779 Sanbina St, Winter Park, FL 32789

  Rare opportunity in the heart of 32789 — priced under $500K, this 3-bedroom, 2-bathroom Winter Park home delivers the location, lot, and bones that buyers in this zip code rarely find at this price point. Zoned for Dommerich Elementary and Winter Park High School and situated on a generous 0.23-acre lot, this is the one worth moving quickly on. Upon entry, a sun-drenched living room leads to a

  Caroline Fiore MAINFRAME REAL ESTATE

  2779 Sanbina St, Winter Park, FL 32789
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  /6

  $1,540 Per Month

  • 3 Beds
  • 1.5 Baths
  • House for Rent

  105 Jergo Rd, Winter Park, FL 32792

  This unique 3 bedroom, 1.5 bathroom Duplex is ready to welcome its new occupants. Spread over one story, this residence offers a perfect blend of space, comfort, and modern amenities. Enjoy ample space for your family with generously sized living areas, including a wide living room for gatherings and quality family time. The Kitchen is equipped with all the essential appliances you would need.

  105 Jergo Rd, Winter Park, FL 32792
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  $400,000 Sold May 29, 2025

  5144 Goldenrod Place Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 36 Days On Market

  Current Estimated Value $409,951

  Last Listing Agent Rebecca Sparks C. APOLLO REALTY INC

  5144 Goldenrod Place Rd, Winter Park, FL 32792
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  Est $205,512 Not Listed For Sale

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  608 Montego Bay Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • 7% Below List Price
  • $196/SF
  • 5 Days On Market

  • Last Sold Price $220,000
  • Oct 29, 2024

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  $420,000

  • 3 Beds
  • 2.5 Baths
  • 1,533 Sq Ft

  3440 Allston Ln, Winter Park, FL 32792

  Exceptional Single-Family Home in Winter Park, FLThis beautifully maintained 3-bedroom, 2.5-bathroom residence offers an impressive open floor plan with elegant laminate flooring throughout, updated just two years ago. The renovated kitchen (2019) features granite countertops and comes fully equipped with all appliances. Major capital improvements include a new roof (2019) and a new HVAC

  Hugo Hernandez EXIT GLOBAL REALTY

  3440 Allston Ln, Winter Park, FL 32792
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  $3,200 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • House for Rent

  653 Symonds Ave, Winter Park, FL 32789

  Charming 3BR/2.5BA single-family home in desirable Winter Park! Interior features include ceramic tile & laminate flooring, ceiling fans, and a bright kitchen with breakfast bar/kitchen island and stainless-steel appliances. Washer/dryer and major kitchen appliances included. Conveniently located near Hannibal Square, Park Ave, Central Park, Rollins College, the Winter Park Community Center, and

  Alessandra Oliveira FLORIDA CONNEXION PROPERTIES

  653 Symonds Ave, Winter Park, FL 32789
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  $1,250,000 Sold Dec 29, 2025

  359 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,395 Sq Ft
  • Built 1979

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Current Estimated Value $1,250,312

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  359 Beloit Ave, Winter Park, FL 32789
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  Est $1,312,510 Not Listed For Sale

  3629 Midiron Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft
  • Built 2024

  3629 Midiron Dr, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $417/SF
  • 13 Days On Market

  • Last Sold Price $1,355,000
  • Jun 12, 2024

  Last Listing Agent Amanda Wood RE/MAX
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  /22

  $439,995 Pending

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft

  1832 E Cheryl Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to Carolyn Estates in highly desirable Winter Park—a charming enclave of just 63 homes ideally located near Lake Howell High School. This beautifully renovated residence offers a truly unique floor plan—the only one of its kind in the community.Featuring 4 bedrooms, 2 bathrooms, and a spacious 2-car garage, this home blends comfort with

  Shanon Luiz SELECTIVE REALTY GROUP LLC

  1832 E Cheryl Dr, Winter Park, FL 32792
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  $1,950 Per Month

  • 3 Beds
  • 1.5 Baths
  • 1,024 Sq Ft
  • House for Rent

  731 W Comstock Ave, Winter Park, FL 32789

  Close to downtown Winter Park, Winter Park Village, and Park Avenue - Charming 3 bedroom 1.5 bath home, with single carport, fenced backyard, ceiling fans and blinds. Tile floors in main living areas and NEW carpet in bedrooms. Additional sun room located off the kitchen with entry to/from carport. This home is available for immediate move in. PETS NEGOTIABLE. Please call to schedule an

  731 W Comstock Ave, Winter Park, FL 32789
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  $468,470 Sold Jun 20, 2025

  1026 Manchester Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,724 Sq Ft
  • Built 1977

  Last Sold Summary

  • 3% Below List Price
  • $272/SF
  • 25 Days On Market

  Current Estimated Value $477,224

  Last Listing Agent David Miller KELLER WILLIAMS HERITAGE REALTY

  1026 Manchester Cir, Winter Park, FL 32792
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  Est $770,632 Not Listed For Sale

  1477 Lone Feather Trail, Winter Park, FL 32792

  • 5 Beds
  • 3.5 Baths
  • 2,894 Sq Ft
  • Built 2021

  1477 Lone Feather Trail, Winter Park, FL 32792

  Last Sold Summary

  • 6% Above List Price
  • $252/SF
  • 30 Days On Market

  • Last Sold Price $730,000
  • Jun 14, 2024

  Last Listing Agent Christopher Soucy REALTY ONE GROUP MVP
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  $370,000

  • 3 Beds
  • 2 Baths
  • 1,283 Sq Ft

  780 Baffie Ave, Winter Park, FL 32789

  Great opportunity to live in Winter Park in the Dubsdread Golf Community. This 3 bedroom, 2 bath home is situated on a deep lot (50 x 140) with 1283 sq. ft., Bamboo hardwood floors in several rooms, split bedroom floor plan, large kitchen with tile floors, and oak cabinets, and the dining room has a tongue and groove wood ceiling. The primary bedroom has Bamboo floors, tongue and groove wood

  Melissa Woodman FANNIE HILLMAN & ASSOCIATES

  780 Baffie Ave, Winter Park, FL 32789
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  $3,475 Per Month

  • 3 Beds
  • 2 Baths
  • 1,670 Sq Ft
  • House for Rent

  1850 Whitehall Dr, Winter Park, FL 32789

  This is a wonderful pool home located in the sought after neighborhood of Kenilworth Shores in Winter Park. It features 3 bedrooms & 2 baths with an open floor plan. Family room/dining room combo, a wonderful Florida room overlooking the backyard & pool area. Enjoy the weekends lounging around the black bottom pool and the lush landscape surrounding the backyard. ALL UTILITIES included! The

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  1850 Whitehall Dr, Winter Park, FL 32789
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  $430,000 Sold Aug 08, 2025

  1006 Bradford Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,130 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Above List Price
  • $202/SF
  • 7 Days On Market

  Current Estimated Value $445,370

  Last Listing Agent Paul Giannotti TERZA REAL ESTATE

  1006 Bradford Dr, Winter Park, FL 32792
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  Est $206,728 Not Listed For Sale

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3704, Winter Park, FL 32792

  Last Sold Summary

  • 3% Above List Price
  • $164/SF
  • 108 Days On Market

  • Last Sold Price $200,000
  • Aug 22, 2024

  Last Listing Agent Larry Ouellette MANA REAL ESTATE
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  /46

  $825,000

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

  1369 Blue Stem Ln, Winter Park, FL 32792

  Nestled in one of the most sought-after neighborhoods in Winter Park, this exceptional gated residence offers the perfect blend of elegance, comfort, and modern efficiency. Ideally located just five minutes from top-rated private schools, this two-story single-family home is designed for both luxurious living and everyday functionality. Upon entry, you are welcomed by a dramatic grand foyer

  He Gao U S GLORY REALTY

  1369 Blue Stem Ln, Winter Park, FL 32792
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  $1,950 Per Month

  • 2 Beds
  • 2 Baths
  • 1,058 Sq Ft
  • House for Rent

  4800 Tangerine Ave, Winter Park, FL 32792

  Beautiful & Spacious 2-Bedroom, 2-Bath Condo for Rent in Winter Park – $1,950/MonthDiscover the perfect blend of comfort, convenience, and lifestyle in this beautifully maintained condo located in the highly desirable Winter Park area. This home offers an exceptional layout with 2 spacious bedrooms and 2 full bathrooms, ideal for families, professionals, or roommates seeking a comfortable and

  4800 Tangerine Ave, Winter Park, FL 32792
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  $390,000 Sold Feb 23, 2026

  1670 Clematis Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,401 Sq Ft
  • Built 1962

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 81 Days On Market

  Current Estimated Value $381,345

  Last Listing Agent Gea Gomez LPT REALTY, LLC

  1670 Clematis Ln, Winter Park, FL 32792
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  Not Listed For Sale

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,079 Sq Ft
  • Built 1974

  3004 George Mason Ave Unit 5 (K-5d), Winter Park, FL 32792

  Last Sold Summary

  • $120/SF
  • 66 Days On Market

  • Last Sold Price $130,000
  • Jul 22, 2024

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  $180,000 Pending

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft

  200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792

  Under contract-accepting backup offers. This isn’t your average condo. It’s professionally updated with large rooms and more closet space than you’ll know what to do with. There’s even a washer and dryer right in the unit (no more laundry runs!), newer appliances, and parking right outside your door. On a scale from 1 to 10, this place is easily a TWENTY! Seriously, no expense was spared to make

  Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

  200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792
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  /18

  $1,400 Per Month

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

  3032 Antique Oaks Cir Unit 145, Winter Park, FL 32792

  1 Bedroom/1 Bath condo in Winter Park's Parkview Village! Situated just off of 436/South Semoran Blvd & so convenient to UCF, Full Sail University, 417 & more! The living room, dining & kitchen layout flows easily with sliding doors that lead to the screened patio! Fresh interior paint, washer & dryer. Parkview Village offers a pool, clubhouse. Take a look today!

  Barry Stephens MAINFRAME REAL ESTATE

  3032 Antique Oaks Cir Unit 145, Winter Park, FL 32792
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  $1,595,000 Sold Sep 02, 2025

  1733 Harmon Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,267 Sq Ft
  • Built 2025

  Last Sold Summary

  • $488/SF
  • 27 Days On Market

  Current Estimated Value $1,561,160

  Last Listing Agent Jordan Freeland SOUTH REALTY, INC

  1733 Harmon Ave, Winter Park, FL 32789
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  Est $454,612 Not Listed For Sale

  Unlisted Address

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

  Unlisted Address

  Last Sold Summary

  • 3% Below List Price
  • $245/SF

  • Last Sold Price $467,990
  • Feb 22, 2024

  Last Listing Agent Stellar Non-Member Agent FL_MFRMLS
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  $629,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,704 Sq Ft

  3110 Heartleaf Place, Winter Park, FL 32792

  Under contract-accepting backup offers. Nestled in the upscale Lost Creek community, this maintained 4-bedroom, 3-bathroom screened pool home offers the perfect blend of comfort and natural beauty with over an acre of land that extends all the way to Howell Creek. Upon entering, you are greeted by high ceilings and an open-concept great room layout. The formal living room flows seamlessly into

  Hajime Shimabukuro FUSILIER MANAGEMENT GROUP

  3110 Heartleaf Place, Winter Park, FL 32792
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  /15

  $1,740 Per Month

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease!

  7429 Daniel Webster Dr, Winter Park, FL 32792

  Rent Special: Receive $100 in rent credit for the first three months with a 12-month lease! Welcome to this enchanting fully furnished 2-bedroom, 2-bathroom condo nestled in the heart of Winter Park, FL! Offering easy access to a plethora of attractions, this home invites you to immerse yourself in the magic of Disney, just 30 minutes away, or bask in the sun at picturesque Cocoa Beach, all

  7429 Daniel Webster Dr, Winter Park, FL 32792
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  $749,000 Sold Aug 13, 2025

  627 Darcey Dr, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,509 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $299/SF
  • 52 Days On Market

  Current Estimated Value $752,148

  Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

  627 Darcey Dr, Winter Park, FL 32792
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  Est $436,231 Not Listed For Sale

  2838 Bright Bird Ln, Winter Park, FL 32792

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

  2838 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $237/SF
  • 8 Days On Market

  • Last Sold Price $452,090
  • Aug 16, 2024

  Last Listing Agent Ellie Hunter PULTE REALTY OF NORTH FLORIDA LLC

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