Winter Park, FL Homes

• 

  

  

  /21

  $562,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,778 Sq Ft

  5233 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your

  Miranda Cady CADENCE LIFESTYLE REAL ESTATE

  5233 Lake Howell Rd, Winter Park, FL 32792
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  /17

  $1,300 - $1,855 per month

  La Aloma

  1 - 3 Beds

  3040 Aloma Ave, Winter Park, FL 32792

  La Aloma Apartments offers the ideal blend of comfort, convenience, and tranquility in the heart of Central Florida. Perfectly situated just minutes from downtown Winter Park, this centrally located community provides easy access to everything Orlando has to offer—including top attractions, dining, shopping, and entertainment. Whether you're a student or professional, you'll appreciate being just

  3040 Aloma Ave, Winter Park, FL 32792
• 

  

  /2

  $3,485,000 Sold Oct 17, 2025

  2171 Forrest Rd, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,565 Sq Ft
  • Built 2016

  Last Sold Summary

  • 9% Below List Price
  • $763/SF
  • 134 Days On Market

  Current Estimated Value $3,402,806

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2171 Forrest Rd, Winter Park, FL 32789
• 

  

  

  /24

  Est $189,749 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  229 Lewfield Cir Unit 229, Winter Park, FL 32792

  229 Lewfield Cir Unit 229, Winter Park, FL 32792
• 

  

  

  /53

  $379,990 Pending

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft

  1378 Chilean Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. Stunning Newly Remodeled Move-In Ready Home!Property Highlights:• 3 Bedrooms | 2 Bathrooms – Both bathrooms fully modernized with contemporary fixtures, sleek tile work, and high-end finishes• Brand-New Flooring Throughout – Fresh, durable, and stylish flooring for a clean, modern look• Gourmet Kitchen with Quartz Countertops – Gorgeous new

  Constantin Florean FUTURE HOME REALTY INC

  1378 Chilean Ln, Winter Park, FL 32792
• 

  

  /39

  $2,880 per month

  • 3 Beds
  • 2 Baths
  • 1,496 Sq Ft
  • House for Rent

  2992 Chantilly Ave, Winter Park, FL 32789

  Welcome to this inviting 3-bedroom, 2-bath single-family pool home. In addition to the main living areas, the home features a large bonus room that can easily be used as an extra bedroom, game room, home office, or entertainment space to fit your lifestyle. Enjoy year-round relaxation in the bright sunroom, which opens directly to the private pool, creating the perfect indoor-outdoor living

  Randy Pierre LEMUEL PROPERTY MANAGEMENT LLC

  2992 Chantilly Ave, Winter Park, FL 32789
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  /2

  $520,000 Sold Mar 31, 2025

  1810 Taylor Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,396 Sq Ft
  • Built 1977

  Last Sold Summary

  • 1% Below List Price
  • $372/SF
  • 0 Days On Market

  Current Estimated Value $535,482

  Last Listing Agent Julia Dalessandro FANNIE HILLMAN & ASSOCIATES

  1810 Taylor Ave, Winter Park, FL 32789
• 

  

  /45

  Est $1,901,867 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 3,954 Sq Ft

  1433 Sarazens Place, Winter Park, FL 32792

  1433 Sarazens Place, Winter Park, FL 32792
• 

  

  /32

  $525,000 Pending

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  1713 W Cheryl Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Pool Rescreen coming! Welcome to Winter Park luxury living in the sought-after Carolyn Estates, offering convenience, upscale updates, and a top-tier location. This fully renovated 4-bedroom, 2-bath pool home on a private corner lot, offering over 2,000sq ft of stunning finished space is in move in ready condition. This home combines smart upgrades,

  Andi Gamble LPT REALTY, LLC

  1713 W Cheryl Dr, Winter Park, FL 32792
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  /35

  $991 - $1,737 per month

  Carlton Arms of Winter Park

  Studio - 3 Beds

  300 Jamestown Dr, Winter Park, FL 32792

  *Call or email for today’s availabilityCarlton Arms of Winter Park, a well-established community with lavishly maintained landscaping, rapid response maintenance, and attentive service staff, offers an unusual atmosphere of peaceful, private home dwelling while simultaneously assuring comforts and conveniences of apartment living.

  300 Jamestown Dr, Winter Park, FL 32792
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  /2

  $1,645,000 Sold May 20, 2025

  681 Balmoral Rd, Winter Park, FL 32789

  • Land
  • 1.14 Acres
  • $1,442,982 per Acre

  Last Sold Summary

  • 17% Below List Price
  • 55 Days On Market

  Current Estimated Value $1,618,558

  Last Listing Agent Chris Burden EPIC REAL ESTATE ADVISORS LLC

  681 Balmoral Rd, Winter Park, FL 32789
• 

  

  /14

  Est $557,113 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789

  1821 Hammerlin Ave Unit A, Winter Park, FL 32789
• 

  

  /42

  $739,000

  • 4 Beds
  • 2 Baths
  • 2,075 Sq Ft

  620 Darcey Dr, Winter Park, FL 32792

  Located in the sought-after Brookshire Heights neighborhood, this classic brick Winter Park home sits on an OVERSIZED LOT and offers space, flexibility, and an exceptional location—with NO HOA. The open floor plan features 4 bedrooms and 2 bathrooms and is filled with natural light throughout. A TWO-CAR GARAGE and EXTENDED DRIVEWAY provide ample parking for guests, multiple vehicles, or

  Jason Asa LPT REALTY, LLC

  620 Darcey Dr, Winter Park, FL 32792
• 

  

  /16

  $2,900 per month

  • 3 Beds
  • 2 Baths
  • 1,567 Sq Ft
  • House for Rent

  3413 Bowman Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 3-bedroom, 2-bathroom home located in the highly desirable Winter Park area, less than a mile from Eastbrook Elementary School and Park Maitland Preschool, and zoned for top-rated Seminole County A schools. Thoughtfully updated with modern finishes and an inviting layout, this home offers both style and functionality in an ideal location. Luxury vinyl

  Ileana Vincenty LPT REALTY, LLC

  3413 Bowman Dr, Winter Park, FL 32792
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  /2

  $335,000 Sold Sep 23, 2025

  5144 N Orange Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1976

  Last Sold Summary

  • 16% Below List Price
  • $263/SF
  • 128 Days On Market

  Current Estimated Value $340,165

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC

  5144 N Orange Ave, Winter Park, FL 32792
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  /24

  Est $830,557 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,957 Sq Ft

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789

  1224 S Pennsylvania Ave Unit 4, Winter Park, FL 32789
• 

  

  /35

  $750,000

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

  676 Dunblane Dr, Winter Park, FL 32792

  This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as

  Emma Kaplan BALDWIN PARK REALTY LLC

  676 Dunblane Dr, Winter Park, FL 32792
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  /30

  $1,802 - $2,691 per month

  Rosalia Winter Park 55+ Active Adult Community

  1 - 2 Beds

  3045 Aloma Ave, Winter Park, FL 32792

  Browse our 1 and 2-bedroom luxury 55+ apartments at Rosalia Winter Park, complete with modern appliances and stunning finishes. Stay connected and engaged with countless luxury amenities and activities designed for your lifestyle by our dedicated onsite management team and exciting amenities, including a clubhouse, fitness center, and robust social calendar-all with an attentive team at your

  3045 Aloma Ave, Winter Park, FL 32792
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  /45

  $322,000 Sold Mar 12, 2025

  7319 Blue Jacket Place W, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,118 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $288/SF
  • 5 Days On Market

  Current Estimated Value $320,137

  Last Listing Agent Jennah LeBruno, LLC RE/MAX TOWN & COUNTRY REALTY

  7319 Blue Jacket Place W, Winter Park, FL 32792
• 

  

  /40

  Est $253,122 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,322 Sq Ft

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1003, Winter Park, FL 32792
• 

  

  /29

  $439,900

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  1518 Pinewood Dr, Winter Park, FL 32789

  Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  1518 Pinewood Dr, Winter Park, FL 32789
• 

  

  /16

  $2,400 per month

  • 3 Beds
  • 2 Baths
  • 1,896 Sq Ft
  • House for Rent

  5133 Oak Hill Dr, Winter Park, FL 32792

  This pet-friendly home features modern finishes and a functional layout with ample kitchen storage, spacious living areas, and abundant natural light throughout. The private yard offers space suitable for gardening or outdoor relaxation. Conveniently located near schools, parks, dining, and local amenities. Technology-enabled maintenance services provide added convenience, and self-touring is

  Daniel Reyes MAIN STREET RENEWAL LLC

  5133 Oak Hill Dr, Winter Park, FL 32792
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  /2

  $397,000 Sold Jul 01, 2025

  1109 Denton Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft
  • Built 1963

  Last Sold Summary

  • 3% Below List Price
  • $321/SF
  • 83 Days On Market

  Current Estimated Value $395,550

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS

  1109 Denton Rd, Winter Park, FL 32792
• 

  

  /28

  Est $370,361 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  4870 Seminole Ave, Winter Park, FL 32792

  4870 Seminole Ave, Winter Park, FL 32792
• 

  

  /76

  $6,895,000 Pending

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
• 

  

  /27

  $1,360 - $2,151 per month

  Westmount at Winter Park

  Studio - 3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Theres no place like Westmount at Winter Park Apartments in Winter Park, FL. These stylish studio, one, two, and three bedroom apartment homes are thoughtfully designed with features like vinyl plank flooring, large closets, and in-home washers and dryers. With the option of sleek stainless steel or black appliances, your kitchen is as functional as it is modern. Step outside and enjoy the serene

  1701 Lee Rd, Winter Park, FL 32789
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  /2

  $3,200,000 Sold Apr 30, 2025

  1833 Loch Berry Rd, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,770 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $671/SF
  • 5 Days On Market

  Current Estimated Value $2,957,584

  Last Listing Agent Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1833 Loch Berry Rd, Winter Park, FL 32789
• 

  

  /22

  Est $5,537,993 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789

  300 S Interlachen Ave Unit 601, Winter Park, FL 32789
• 

  

  /18

  $195,000

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792

  Beautiful 2 bedroom / 2 bath first floor condo in Winter Park's Four Seasons community. Great floorplan with large living room, separate dining space, and updated kitchen with white cabinetry and granite countertops. New windows installed, new water heater 2023, new roof 2023, replumbed, AC 2015! Primary bedroom with walk in closet and en-suite bath with walk in shower. Enjoy a cozy screened

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
• 

  

  /14

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft
  • House for Rent

  1826 Pineview Cir, Winter Park, FL 32792

  This 3 bedroom, 2 bathroom home is located in the heart of Winter Park. Enjoy all Downtown Winter Park, Park Avenue's shops and restaurants, Winter Park Village, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a large main living area, dining room, an updated kitchen with stainless steel appliances, a wonderful

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  1826 Pineview Cir, Winter Park, FL 32792
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  /2

  $145,000 Sold Aug 13, 2025

  7352 Swallow Run, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 802 Sq Ft
  • Built 1983

  Last Sold Summary

  • 39% Below List Price
  • $181/SF
  • 68 Days On Market

  Current Estimated Value $144,661

  Last Listing Agent Ashley Quandt LEERDAM PROPERTIES INC.

  7352 Swallow Run, Winter Park, FL 32792
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  /2

  Est $2,721,509 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft

  1737 Lookout Landing Cir, Winter Park, FL 32789

  1737 Lookout Landing Cir, Winter Park, FL 32789
• 

  

  /30

  $425,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 1,840 Sq Ft

  1543 Lawndale Cir, Winter Park, FL 32792

  Enjoy the convenience of living just minutes from top-rated schools, colleges, shopping, and major highways in this beautifully updated, light-filled home set within a well-established, family-friendly lakefront community. The home features 2018 roof, fencing, and plumbing. The interior paint, fully remodeled kitchen with appliances, half bath updates and tile flooring were completed in 2021.

  Lesley Byrd Arium Real Estate, LLC

  1543 Lawndale Cir, Winter Park, FL 32792
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  /30

  $1,250 - $2,680 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

  $228,000 Sold Jun 27, 2025

  1979 Staunton Ave, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1948

  Last Sold Summary

  • 24% Below List Price
  • $310/SF
  • 16 Days On Market

  Current Estimated Value $237,432

  Last Listing Agent Michael Kara CORBELO LLC

  1979 Staunton Ave, Winter Park, FL 32789
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  /32

  Est $198,950 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 3504, Winter Park, FL 32792
• 

  

  /88

  $8,500,000

  • 5 Beds
  • 6 Baths
  • 6,502 Sq Ft

  1112 Preserve Point Dr, Winter Park, FL 32789

  Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

  Kelly Price KELLY PRICE & COMPANY LLC

  1112 Preserve Point Dr, Winter Park, FL 32789
• 

  

  /15

  $2,700 per month

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • House for Rent

  2352 Smiley Ave, Winter Park, FL 32792

  Charming Winter Park rental in a highly desirable location featuring a traditional floorplan and a gorgeous fenced yard. Enjoy separate living and dining rooms—perfect for everyday comfort and entertaining. Conveniently located just minutes from the best of Winter Park, including popular restaurants, shopping, parks, Rollins College, and nearby medical offices. Rent includes lawn maintenance and

  Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

  2352 Smiley Ave, Winter Park, FL 32792
• 

  /2

  $385,000 Sold Apr 03, 2025

  1873 Poinciana Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 1,904 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Above List Price
  • $202/SF
  • 2 Days On Market

  Current Estimated Value $402,748

  Last Listing Agent Benondre Cerezo COLDWELL BANKER REALTY

  1873 Poinciana Rd, Winter Park, FL 32792
• 

  

  /42

  Est $703,995 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

Showing Results 241 - 280, Page 7 of 18