Winter Park, FL Homes

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  /26

  $189,000

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

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

  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 generously sized master suites, each with its own

  Qing Lin SPRINGHILL PROPERTIES LLC

  3370 Cedar Springs Place Unit 156, Winter Park, FL 32792
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  /21

  $2,649 Per Month

  • 3 Beds
  • 2 Baths
  • 1,422 Sq Ft
  • House for Rent

  1947 Summerfield Rd, Winter Park, FL 32792

  Welcome home! This fantastic 3-bedroom, 2-bath home is available for immediate move-in! This property is a short drive from downtown Winter Park, the Crosby Center for Health and Wellbeing, Cady Way Park, and more! , this property features a comfortable layout with well-apportioned bedrooms and bathrooms, a lovely kitchen with lots of counter and cabinet space, and many desirable features. Act

  Steve Simpson 407 PROPERTIES

  1947 Summerfield Rd, Winter Park, FL 32792
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  $1,110,000 Sold Aug 26, 2025

  233 Hampden Place, Winter Park, FL 32789

  • 5 Beds
  • 3 Baths
  • 2,813 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $395/SF
  • 7 Days On Market

  Current Estimated Value $1,164,421

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
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  /18

  Est $446,107 Not Listed For Sale

  2778 Bright Bird Ln, Winter Park, FL 32792

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

  2778 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $224/SF
  • 1 Day On Market

  • Last Sold Price $427,000
  • Mar 25, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /28

  $440,000 Pending

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

  3642 Periwinkle Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. 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

  John Hwangbo HONEST REAL ESTATE COMPANY

  3642 Periwinkle Dr, Winter Park, FL 32792
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  /16

  $2,795 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft
  • Townhouse for Rent

  1403 Broad Wing Ln, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Hawks Crest along the southern shores of beautiful Lake Howell, this ideal location provides easy access to major employment sectors and desirable Winter Park shopping and dining destinations including Park Avenue and Winter Park Village. The home has an open floor plan with tile flooring throughout the downstairs living

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1403 Broad Wing Ln, Winter Park, FL 32792
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  /2

  $200,000 Sold Sep 13, 2025

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Built 1984

  Last Sold Summary

  • 11% Below List Price
  • $174/SF
  • 131 Days On Market

  Current Estimated Value $198,921

  Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792
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  /29

  Est $556,258 Not Listed For Sale

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,003 Sq Ft
  • Built 2015

  8097 Pleasant Pine Cir, Winter Park, FL 32792

  Last Sold Summary

  • $277/SF
  • 2 Days On Market

  • Last Sold Price $555,000
  • Feb 21, 2024

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /46

  $1,849,000

  • 4 Beds
  • 3.5 Baths
  • 3,727 Sq Ft

  1840 Bryan Ave, Winter Park, FL 32789

  This custom 2014-built Winter Park residence is stretched over a double lot with a backyard resort style retreat yet close to all Winter Park offers. A home with function and flexibility with a separate guest house, office or studio based on your needs. This thoughtfully designed home is sophisticated with casual comfort and showcases four bedrooms, 3.5 baths and nearly 3,800 square feet,

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  1840 Bryan Ave, Winter Park, FL 32789
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  /17

  $1,650 Per Month

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

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792

  Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for

  Jacqueline Ramos JML REALTY INVESTMENTS LLC

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
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  /2

  $3,200,000 Sold Nov 04, 2025

  1900 W Fawsett Rd, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,600 Sq Ft
  • Built 1969

  Last Sold Summary

  • 4% Below List Price
  • $696/SF
  • 6 Days On Market

  Current Estimated Value $3,144,617

  Last Listing Agent Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  1900 W Fawsett Rd, Winter Park, FL 32789
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  /16

  Est $185,331 Not Listed For Sale

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  3378 Cedar Springs Place Unit 154, Winter Park, FL 32792

  Last Sold Summary

  • 12% Below List Price
  • $205/SF
  • 132 Days On Market

  • Last Sold Price $211,000
  • Jun 28, 2024

  Last Listing Agent ALLISON JOHNSTON THE SIMON SIMAAN GROUP
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  /26

  $149,000

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

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

  READY TO BE SOLD! Accepting great offers. Welcome home! NEWLY RENOVATED BATHROOM on deck. Is Winter Park your destination or desire? Investment Potential, Student Sanctuary or just a long-awaited life. Centrally located at your fingertips. Location, Lifestyle, Luxurious Zip Code, Friends, Culture and Community. Discover an unparalleled opportunity to own a piece of prime real estate in the heart

  Kelly Flores COLDWELL BANKER REALTY

  3019 Antique Oaks Cir Unit 124, Winter Park, FL 32792
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  /12

  $1,800 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  612 Trinidad Ct Unit 612, Winter Park, FL 32792

  Beautiful 2 bed/2 bath condo villa in Winter Park Villas. Over 1000 sq.ft. with two large bedrooms with walk-in closets, two nicely renovated bathrooms, renovated kitchen, large living room and dining area. Ceramic tile flooring throughout, granite countertops in kitchen and bathrooms. All appliances including washer and dryer inside unit. End unit with covered front patio and back porch area

  Carolina Barriento JEXOR LLC

  612 Trinidad Ct Unit 612, Winter Park, FL 32792
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  /2

  $879,000 Sold Nov 14, 2025

  451 Fairfax Ave, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,227 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $395/SF
  • 5 Days On Market

  Current Estimated Value $870,134

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  451 Fairfax Ave, Winter Park, FL 32789
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  /10

  Est $431,687 Not Listed For Sale

  2726 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2023

  2726 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $223/SF

  • Last Sold Price $426,190
  • Dec 20, 2023

  Last Listing Agent Denise Del Castillo LPT REALTY, LLC
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  /19

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  Carmen Vazquez REALTY TECH INC

  7706 Country Place Unit A8, Winter Park, FL 32792
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  /13

  $2,295 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

  $630,000 Sold Aug 11, 2025

  1792 Killarney Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,264 Sq Ft
  • Built 1958

  Last Sold Summary

  • 3% Below List Price
  • $278/SF
  • 1 Day On Market

  Current Estimated Value $652,518

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789
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  /25

  Est $2,012,844 Not Listed For Sale

  1925 Killarney Dr, Winter Park, FL 32789

  1925 Killarney Dr, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • 33 Days On Market

  • Last Sold Price $2,000,000
  • Feb 28, 2024

  Last Listing Agent Cathy Marino CATHY S. MARINO REALTY, INC.
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  /27

  $115,000

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft

  1695 Lee Rd Unit E204, Winter Park, FL 32789

  Welcome to this lovely open-concept 2 bedroom, 1 bathroom condo, perfectly situated in a fantastic area close to plenty of shopping, dining, and everyday conveniences. Ideal for first-time buyers, downsizing, or investors looking for a solid opportunity! This property highlights an open-concept bright interior with great natural light living and dining area. Two spacious bedrooms with 1 bathroom.

  Brandy Ray LOKATION

  1695 Lee Rd Unit E204, Winter Park, FL 32789
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  /25

  $5,490 Per Month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • Condo for Rent

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

  Steven Koleno BEYCOME OF FLORIDA LLC

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  /2

  $965,000 Sold Mar 12, 2026

  1444 Pelican Bay Trail, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 3,121 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Below List Price
  • $309/SF
  • 314 Days On Market

  Current Estimated Value $963,486

  Last Listing Agent Jacob Hara TRANSCEND REALTY

  1444 Pelican Bay Trail, Winter Park, FL 32792
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  /25

  Est $361,245 Not Listed For Sale

  7494 Aloma Pines Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft
  • Built 2017

  7494 Aloma Pines Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $195/SF
  • 112 Days On Market

  • Last Sold Price $365,000
  • May 01, 2024

  Last Listing Agent Krys Guillaume CENTURY 21 CARIOTI
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  /55

  $1,500,000 Pending

  • 2 Beds
  • 2 Baths
  • 2,281 Sq Ft

  246 Palmer Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to 246 Palmer Avenue! Build your dream home or live in this charming home As-Is. Situated on a 14,252 sq.ft (0.33) corner lot on a beautiful brick street in the heart of Winter Park, this charming cottage offers timeless character, thoughtful updates, and a highly desirable location just minutes from Park Avenue, Rollins College, and the Winter Park

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  246 Palmer Ave, Winter Park, FL 32789
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  /36

  $4,600 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,406 Sq Ft
  • House for Rent

  1580 Oakhurst Ave, Winter Park, FL 32789

  Prepare to be impressed by this beautiful two story home on a charming brick paved street in Winter Park! This 4 bed 2.5 bathroom home awaits you with recent interior and exterior paint updates, hard wood floors, granite countertops and upgraded stainless steel appliances. A grapefruit tree and lush landscaping create a serene setting to relax on your sprawling front porch. Upon entering you are

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1580 Oakhurst Ave, Winter Park, FL 32789
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  /2

  $382,000 Sold Jul 02, 2025

  1909 Edwin Blvd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,355 Sq Ft
  • Built 1955

  Last Sold Summary

  • 7% Below List Price
  • $282/SF
  • 34 Days On Market

  Current Estimated Value $428,386

  Last Listing Agent Brian Craib OLDE TOWN BROKERS INC

  1909 Edwin Blvd, Winter Park, FL 32792
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  /7

  Est $87,910 Not Listed For Sale

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

  • Studio
  • 1 Bath
  • 590 Sq Ft
  • Built 1974

  7309 Daniel Webster Dr Unit B, Winter Park, FL 32792

  Last Sold Summary

  • 5% Above List Price
  • $142/SF
  • 44 Days On Market

  • Last Sold Price $84,000
  • Feb 26, 2024

  Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC
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  /55

  $495,000

  • 2 Beds
  • 2.5 Baths
  • 1,428 Sq Ft

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789

  Lakefront townhome in desirable Killarney Bay directly on Lake Killarney, offering 2 bedrooms, 2.5 baths, and a one-car carport. This spacious residence features an open living and dining area that flows to a screened porch, perfect for relaxing and enjoying tranquil lake views in a well-maintained complex. Both bedrooms are upstairs for privacy, each with its own bath, with a convenient half

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  630 Killarney Bay Ct Unit 3, Winter Park, FL 32789
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  /20

  $1,600 Per Month

  • 2 Beds
  • 1.5 Baths
  • 825 Sq Ft
  • Townhouse for Rent

  2523 Alexa Ct, Winter Park, FL 32792

  Enjoy Florida living at its best. Perfectly situated just minutes from Downtown Winter Park, near an abundance of restaurants, movie theater, schools. Close to the I4 and 417, short drive to the beach, mins to Theme Parks, golf courses & airport makes this comfortable 2 bedroom 1.5 bath duplex a must see. The interior features tile flooring throughout for cooler summers and a private backyard

  Joseph LaRosa LA ROSA REALTY LLC

  2523 Alexa Ct, Winter Park, FL 32792
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  /2

  $89,750 Sold Dec 05, 2025

  3002 George Mason Ave Unit 3, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,085 Sq Ft
  • Built 1974

  Last Sold Summary

  • 25% Below List Price
  • $83/SF
  • 92 Days On Market

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  3002 George Mason Ave Unit 3, Winter Park, FL 32792
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  /2

  Est $993,813 Not Listed For Sale

  311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 6-18, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $477/SF
  • 102 Days On Market

  • Last Sold Price $1,000,000
  • Dec 27, 2024

  Last Listing Agent Ashley Jacobs CHARLES RUTENBERG REALTY ORLANDO
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  /81

  $3,799,000 Pending

  • 5 Beds
  • 5 Baths
  • 4,451 Sq Ft

  150 Dana Way, Winter Park, FL 32789

  JUST COMPLETED....WINTER PARK / LAKE SUE DISTRICT — A TRUE STANDOUT IN TODAY’S LUXURY NEW CONSTRUCTION MARKETProudly presented by RARE Builders, a name synonymous with design-forward custom homes that continue to help set and raise the standard in Orlando and Winter Park, this newly completed residence represents a rare opportunity to secure a fully realized custom home in one of the area’s

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  150 Dana Way, Winter Park, FL 32789
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  /52

  $8,950 Per Month

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Condo for Rent

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
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  /2

  $495,000 Sold Feb 17, 2026

  422 S Ranger Blvd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1965

  Last Sold Summary

  • 7% Below List Price
  • $295/SF
  • 77 Days On Market

  Current Estimated Value $508,041

  Last Listing Agent David Perez COLDWELL BANKER REALTY

  422 S Ranger Blvd, Winter Park, FL 32792
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  Est $1,351,797 Not Listed For Sale

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  • 3 Beds
  • 4 Baths
  • 2,950 Sq Ft
  • Built 2007

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $436/SF
  • 2 Days On Market

  • Last Sold Price $1,285,000
  • Feb 15, 2024

  Last Listing Agent William Maroon MAROON REALTY GROUP LLC
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  /99

  $5,250,000

  • 5 Beds
  • 6.5 Baths
  • 7,278 Sq Ft

  2211 Azalea Place, Winter Park, FL 32789

  Exquisite Waterfront Estate in the Heart of Winter Park - Welcome to 2211 Azalea Place, a rare and remarkable waterfront estate nestled on a quiet street in one of Winter Park’s most prestigious neighborhoods—just moments from the exclusive Winter Park Racquet Club. This extraordinary residence offers the perfect blend of timeless architecture, refined finishes, and state-of-the-art updates, all

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  2211 Azalea Place, Winter Park, FL 32789
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  /22

  $1,450 Per Month

  • 1 Bed
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  1555 Michigan Ave, Winter Park, FL 32789

  Are you looking for a spacious 1 bedroom 1 bathroom unit to call home? This home features its own washer and dryer, a large bedroom and living room, a spacious kitchen with ample countertop space, plenty of cabinets. The back sunroom would make a great office or a bright sitting area. The home is located 1 mile from Park Avenue. In addition, the home is located within walking distance of

  Troy Hensley BHHS FLORIDA REALTY

  1555 Michigan Ave, Winter Park, FL 32789
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  /2

  $755,000 Sold Jul 18, 2025

  1000 Howell Branch Rd, Winter Park, FL 32789

  • Land
  • 23,958 Sq Ft
  • $1,372,727 per Acre

  Last Sold Summary

  • 30% Below List Price
  • 241 Days On Market

  Current Estimated Value $822,466

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC

  1000 Howell Branch Rd, Winter Park, FL 32789
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  /33

  Est $439,615 Not Listed For Sale

  2003 Canny Cove, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2023

  2003 Canny Cove, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $238/SF
  • 31 Days On Market

  • Last Sold Price $423,900
  • Feb 02, 2024

  Last Listing Agent Simon Colak USCO CAPITAL GROUP

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