Winter Park, FL Homes

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  $435,000

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft

  2224 Shadowland Loop, Winter Park, FL 32792

  **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 450-7733

  2224 Shadowland Loop, Winter Park, FL 32792
• Explore Winter Park

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  /26

  $1,465 per month

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

  2500 Lee Rd Unit 244, Winter Park, FL 32789

  Discover easy living at 2500 Lee Road, Unit 244, Winter Park, FL 32789. This charming spacious 1 bedroom, 1 full bathroom condo is located in the heart of Winter Park, offering comfort, convenience, and access to everything you need. Bright kitchen with plenty of storageand an Open living area with natural light Community features may include: Swimming pool, Assigned parking, Landscaped

  

  Rustina Gibson

  RE/MAX VANTAGE

  (321) 336-5615

  2500 Lee Rd Unit 244, Winter Park, FL 32789
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  $299,000 Sold Jan 15, 2026

  2804 Whispering Way, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,078 Sq Ft
  • Built 1986

  Last Sold Summary

  • $277/SF
  • 4 Days On Market

  Current Estimated Value $300,993

  Last Listing Agent Robin Leedom-Hafen TOP VALUE PROPERTIES LLC

  2804 Whispering Way, Winter Park, FL 32792
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  /2

  Est $217,515 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $193/SF
  • 134 Days On Market

  Last Sold Price $225,000

  Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC
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  /58

  $479,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 1,770 Sq Ft

  3463 Arnel Dr, Winter Park, FL 32792

  Your pool home in Winter Park. This home offers three bedrooms plus a versatile bonus room, approximately 1,770 sq ft of living space, built in 1967, along with a two-car garage and extended driveway for additional parking. Located in the established Eastbrook community with no HOA. Key updates include a roof replaced in 2018, solar panels installed in 2020 (fully paid off), water heater replaced

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (689) 356-6537

  3463 Arnel Dr, Winter Park, FL 32792
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  /29

  $1,799 per month

  • 2 Beds
  • 1 Bath
  • 804 Sq Ft
  • Condo for Rent

  151 N Orlando Ave Unit 101, Winter Park, FL 32789

  Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of theLake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & openlayout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining orcasual family meals. Granite

  

  Elizabeth Fowler

  THE FLORIDA PROPERTY SHOP SALE

  (689) 588-1599

  151 N Orlando Ave Unit 101, Winter Park, FL 32789
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  /2

  $130,000 Sold May 09, 2025

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Built 1966

  Last Sold Summary

  • 10% Below List Price
  • $148/SF
  • 25 Days On Market

  Current Estimated Value $131,826

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY

  1695 Lee Rd Unit E205, Winter Park, FL 32789
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  /55

  Est $953,273 Not Listed For Sale

  1484 Via Sangro Place, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,063 Sq Ft
  • Built 2015

  1484 Via Sangro Place, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $317/SF
  • 5 Days On Market

  Last Sold Price $970,000

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  /27

  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,310 Sq Ft

  5647 Garden Grove Cir, Winter Park, FL 32792

  PRICE ADJUSTMENT! Welcome to this beautifully maintained 3-bedroom, 2-bath home for sale in Winter Park located in the highly sought-after Garden Grove community. Situated on a generously sized lot, this property offers the perfect blend of comfort, functionality, and outdoor living, with plenty of room to add a pool and create your own private backyard retreat. Inside, you’ll love the spacious

  

  Carla Robles

  WATSON REALTY CORP

  (321) 379-8162

  5647 Garden Grove Cir, Winter Park, FL 32792
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  /65

  $6,995 per month

  • 5 Beds
  • 4 Baths
  • 2,918 Sq Ft
  • House for Rent

  2075 Jewell Ave, Winter Park, FL 32789

  FULLY FURNISHED 5br/4b +bonus loft GEM! Welcome to 2075 Jewel Avenue, an exceptional residence nestled in the heart of Winter Park, 32789—one of Central Florida’s most sought-after communities. Ideally situated just minutes from the vibrant shops and dining along Park Avenue and the scenic beauty of Rollins College, this home offers the perfect blend of charm, convenience, and lifestyle. Set on a

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 483-3119

  2075 Jewell Ave, Winter Park, FL 32789
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  /2

  $2,144,000 Sold Aug 21, 2025

  1077 N Pennsylvania Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft
  • Built 2004

  Last Sold Summary

  • $619/SF
  • 0 Days On Market

  Current Estimated Value $2,127,094

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  /46

  Est $1,190,660 Not Listed For Sale

  1778 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft
  • Built 2023

  1778 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $526/SF
  • 51 Days On Market

  Last Sold Price $1,250,000

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /65

  $1,150,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 2.5 Baths
  • 2,431 Sq Ft

  1800 Magnolia Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Experience refined living in this exquisitely renovated custom home, positioned on an oversized corner lot in one of the area’s most peaceful and private neighborhoods. Tucked away at the end of a quiet dead-end street, this residence offers an exceptional blend of craftsmanship, sophistication, and modern comfort. Inside, soaring 10-foot ceilings

  

  Kathy Summers

  FLORIDA REALTY INVESTMENTS

  (321) 306-4359

  1800 Magnolia Ave, Winter Park, FL 32789
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  /15

  $2,975 per month

  • 3 Beds
  • 2 Baths
  • 1,195 Sq Ft
  • House for Rent

  1891 Oglesby Ave, Winter Park, FL 32789

  Beautifully maintained home in the highly desirable Winter Park 32789 neighborhood. This charming property offers an inviting floor plan with abundant natural light, spacious living and dining areas, and a well-appointed kitchen with generous counter space and modern finishes. Comfortable bedrooms provide ample storage, and the primary suite offers a private and peaceful retreat. Flexible bonus

  

  Paul Jimenez

  URBANISTA BROKERS

  (321) 977-5674

  1891 Oglesby Ave, Winter Park, FL 32789
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  $290,000 Sold Feb 06, 2026

  1920 Carrigan Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1954

  Last Sold Summary

  • 14% Below List Price
  • $233/SF
  • 141 Days On Market

  Current Estimated Value $306,967

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
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  /2

  Est $1,100,764 Not Listed For Sale

  625 N Interlachen Ave Unit A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,718 Sq Ft
  • Built 1981

  625 N Interlachen Ave Unit A, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $666/SF
  • 196 Days On Market

  Last Sold Price $1,145,000

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC
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  /39

  $474,000 Pending

  • 2 Beds
  • 1 Bath
  • 925 Sq Ft

  764 W Comstock Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this charming 1935 Winter Park bungalow that blends timeless character with smart, modern upgrades in one of the city’s most walkable locations. This 2-bedroom, 1-bath home offers 1,002 square feet of thoughtfully updated living space, including a remodeled kitchen and bathroom (2021), newer ROOF (2021), Carrier A/C (2020), new flooring, and a

  

  Manny del Valle

  KELLER WILLIAMS WINTER PARK

  (321) 475-7512

  764 W Comstock Ave, Winter Park, FL 32789
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  $1,295 - $2,075 per month

  Oak Reserve at Winter Park

  1 - 3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  541 Oak Reserve Ln, Winter Park, FL 32792
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  /2

  $620,000 Sold Jul 21, 2025

  2855 Lion Heart Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $359/SF
  • 62 Days On Market

  Current Estimated Value $584,472

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
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  /26

  Est $187,580 Not Listed For Sale

  851 Miles Ave Unit 15, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Built 1984

  851 Miles Ave Unit 15, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $235/SF
  • 101 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Chris Creegan CREEGAN GROUP
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  /55

  $574,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,948 Sq Ft

  2814 Sheriff Way, Winter Park, FL 32792

  Under contract-accepting backup offers. Under Contract. Backup offers welcome.Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two

  

  Angela Carney

  CORCORAN PREMIER REALTY

  (321) 220-9015

  2814 Sheriff Way, Winter Park, FL 32792
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  /17

  $1,750 per month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit C206, Winter Park, FL 32789

  Beautiful and move-in ready condo!Located on the second floor in a quiet community, perfect for families or professionals seeking comfort and convenience. 1.- Property Features2 Bedrooms1 Full BathroomSecond-floor unit (added privacy)Total area: 881 sqft 2.- Comfort & Interior FeaturesCentral Air ConditioningCentral HeatingCeiling FansHigh CeilingsOpen

  Yein Ross ROSS RENTALS LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  /2

  $675,000 Sold Jul 10, 2025

  1511 Chestnut Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,275 Sq Ft
  • Built 1960

  Last Sold Summary

  • $529/SF
  • 1 Day On Market

  Current Estimated Value $668,030

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
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  Not Listed For Sale

  100 S Interlachen Ave Unit 502D, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1971

  100 S Interlachen Ave Unit 502D, Winter Park, FL 32789

  Last Sold Summary

  • $741/SF
  • 0 Days On Market

  Last Sold Price $939,000

  Last Listing Agent Jeff Clark COLDWELL BANKER REALTY
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  /36

  $269,900

  • 2 Beds
  • 2 Baths
  • 1,495 Sq Ft

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792

  Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location.The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning

  

  Sarah Doyer

  COLDWELL BANKER REALTY

  (321) 510-4129

  2501 Tahoe Cir Unit 32501, Winter Park, FL 32792
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  /75

  $1,465 - $3,341 per month

  Bainbridge Winter Park

  1 - 3 Beds

  1400 Morgan Stanley Ave, Winter Park, FL 32789

  Celebrate the power of possibilities. Signature details enhance grand features in expansive homes, all a promise to your heightened prosperity at Bainbridge Winter Park. In the heart of Winter Park, Florida’s lush parks and gardens, museums, festivals, and events - you’re central to the finer things in life.

  1400 Morgan Stanley Ave, Winter Park, FL 32789
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  $955,000 Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $977,629

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  /2

  Est $148,814 Not Listed For Sale

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792

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

  3358 Cedar Springs Place Unit 159, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $145/SF
  • 59 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  /41

  $525,000

  • 2 Beds
  • 1 Bath
  • 1,073 Sq Ft

  1036 Aragon Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Welcome to 1036 Aragon Avenue, a charming Winter Park bungalow perfectly positioned in one of Central Florida’s most sought-after locations. Nestled along picturesque cobblestone roads and surrounded by mature, tree-lined streets, this move-in ready home captures the character and warmth that make Winter Park real estate so desirable. Located just

  

  Tim Veigle

  WATSON REALTY CORP

  (321) 516-0689

  1036 Aragon Ave, Winter Park, FL 32789
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  /30

  $2,200 per month

  • 3 Beds
  • 2 Baths
  • 1,106 Sq Ft
  • House for Rent

  7522 Laurel Springs Dr, Winter Park, FL 32792

  Winter Park High School District! Well-maintained 3-bedroom and 2-bathroom home in Laurel Springs featuring a bright, spacious living area with brand new vinyl floor. Step into a large enclosed patio overlooking a fully fenced backyard—perfect for relaxing evenings or hosting gatherings year-round. Convenient access to shopping, dining, and major highways. Move-in ready—don’t miss this

  Liu Zhang JOY ESTATE ENTERPRISE INC

  7522 Laurel Springs Dr, Winter Park, FL 32792
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  /2

  $280,000 Sold Jul 30, 2025

  700 Melrose Ave Unit A22, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,074 Sq Ft
  • Built 1964

  Last Sold Summary

  • 11% Below List Price
  • $261/SF
  • 130 Days On Market

  Current Estimated Value $275,942

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  /2

  Est $422,464 Not Listed For Sale

  8413 Commander Cove, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,634 Sq Ft
  • Built 1985

  8413 Commander Cove, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $263/SF
  • 15 Days On Market

  Last Sold Price $430,000

  Last Listing Agent Tim Boon CREEGAN GROUP
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  /26

  $270,000

  • 3 Beds
  • 2 Baths
  • 1,050 Sq Ft

  1952 Spring St, Winter Park, FL 32792

  Discover the opportunity to own in Winter Park at 1952 Spring Street—a well loved 3-bedroom, 2-bath townhouse offering charm, functionality, and a private yard, a rare find in this desirable area. Nestled in a well-established neighborhood, this home provides a peaceful residential feel and tranquility while remaining just minutes from everything Winter Park has in store.The interior features

  

  Bethanne Baer

  BEAR TEAM REAL ESTATE

  (321) 517-0753

  1952 Spring St, Winter Park, FL 32792
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  $1,674 per month

  Elon Winter Park

  1 Bed

  712 Nicolet Ave, Winter Park, FL 32789

  Welcome to Elon Winter Park Apartments in Winter Park, Florida, where chic meets serenity in the heart of Winter Park's vibrant tapestry. Nestled within this charming community, our boutique one-bedroom apartments redefine urban living with spacious interiors, a contemporary aesthetic, and designer accents that elevate every moment. Immerse yourself in the allure of Winter Park's entertainment

  712 Nicolet Ave, Winter Park, FL 32789
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  $1,300,000 Sold Aug 28, 2025

  1500 Mizell Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,303 Sq Ft
  • Built 1957

  Last Sold Summary

  • $564/SF
  • 2 Days On Market

  Current Estimated Value $1,298,029

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
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  /2

  Est $254,740 Not Listed For Sale

  5122 Lazy Oaks Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,008 Sq Ft
  • Built 1982

  5122 Lazy Oaks Dr, Winter Park, FL 32792

  Last Sold Summary

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

  Last Sold Price $270,000

  Last Listing Agent Kevin Pribell ACRES INC
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  /33

  $200,000

  • 2 Beds
  • 2 Baths
  • 953 Sq Ft

  225 Lewfield Cir, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 237-3113

  225 Lewfield Cir, Winter Park, FL 32792
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  /12

  $2,550 per month

  • 2 Beds
  • 2 Baths
  • 1,140 Sq Ft
  • Condo for Rent

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789

  Enjoy easy, lakefront living in this beautifully maintained 2-bedroom, 2-bath condo in the desirable Killarney Bay community in Winter Park! This spacious unit features an open-concept layout with abundant natural light, a well-appointed kitchen, and comfortable living and dining areas—perfect for both relaxing and entertaining. Both bedrooms offer generous space, with a private primary suite

  David Drawdy KELLER WILLIAMS REALTY AT THE PARKS

  110 Killarney Bay Ct Unit 1, Winter Park, FL 32789
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  /2

  $374,900 Sold Oct 10, 2025

  2028 Leanne Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1968

  Last Sold Summary

  • $244/SF
  • 9 Days On Market

  Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

  2028 Leanne Ct, Winter Park, FL 32792
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  /2

  Est $453,682 Not Listed For Sale

  1409 Hyde Park Dr, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,018 Sq Ft
  • Built 1986

  1409 Hyde Park Dr, Winter Park, FL 32792

  Last Sold Summary

  • $225/SF
  • 128 Days On Market

  Last Sold Price $455,000

  Last Listing Agent Leyder Salamanca FLORIDA REALTY INVESTMENTS

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