Winter Park, FL Homes

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  $424,900

  • 4 Beds
  • 2.5 Baths
  • 1,616 Sq Ft

  1871 Casselwood St, Winter Park, FL 32792

  Beautifully updated, move-in ready home in Winter Park. A brand new A/C system is scheduled to be installed. This 4-bedroom, 2.5-bath home with a 2-car garage features waterproof luxury vinyl flooring, fresh interior finishes, new recessed lighting, and updated ceiling fans, all combined with a bright and functional layout. As you enter, you are welcomed by a custom wood decorative accent wall

  

  Alexa Monasterio Flores

  KELLER WILLIAMS ADVANTAGE 2 REALTY

  (321) 252-6747

  1871 Casselwood St, Winter Park, FL 32792
• Explore Winter Park

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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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  $2,144,000 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 $2,106,050

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  1077 N Pennsylvania Ave, Winter Park, FL 32789
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  Est $1,073,262 Not Listed For Sale

  1975 Biscayne Dr, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,270 Sq Ft
  • Built 2020

  1975 Biscayne Dr, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $304/SF
  • 68 Days On Market

  • Last Sold Price $995,000
  • May 09, 2025

  Last Listing Agent nana Ahn SOGO REAL ESTATE SERVICES LLC
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  /22

  $262,000

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
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  /35

  Starting at $1,168 Per Month

  • 1 - 2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  Seabrook

  (689) 220-6237

  

  3114 Terry Brook Dr, Winter Park, FL 32792
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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 $292,084

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
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  Not Listed For Sale

  1630 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2024

  1630 Haven Dr, Orlando, FL 32803

  Last Sold Summary

  • $392/SF
  • 53 Days On Market

  • Last Sold Price $654,000
  • May 09, 2025

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY
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  /21

  $261,500

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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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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  $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 $588,926

  Last Listing Agent Kevin Henao LA ROSA REALTY LLC

  2855 Lion Heart Rd, Winter Park, FL 32792
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  Est $724,461 Not Listed For Sale

  1806 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  1806 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 5% Above List Price
  • $342/SF
  • 61 Days On Market

  • Last Sold Price $690,000
  • May 08, 2025

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /42

  $370,000

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft

  3374 Hamlet Loop, Winter Park, FL 32792

  Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits your lifestyle. The living room and dining

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (689) 334-1742

  3374 Hamlet Loop, Winter Park, FL 32792
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  Starting at $1,699 Per Month

  • 1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  Vintage Winter Park Apartments

  (689) 220-5580

  

  7490 Dwell Well Way, Winter Park, FL 32792
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  $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 $664,935

  Last Listing Agent Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1511 Chestnut Ave, Winter Park, FL 32789
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  /2

  Est $636,781 Not Listed For Sale

  1401 Lone Feather Trail, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,770 Sq Ft
  • Built 2022

  1401 Lone Feather Trail, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $353/SF
  • 75 Days On Market

  • Last Sold Price $625,000
  • May 09, 2025

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY
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  $1,150,000

  • 4 Beds
  • 2 Baths
  • 2,750 Sq Ft

  1981 Blue Ridge Rd, Winter Park, FL 32789

  Welcome to 1981 Blue Ridge Rd in Winter Park, a spacious 4-bedroom, 2-bath home featuring an open floorplan, a generous family room, and a layout designed for both comfortable everyday living and easy entertaining. The home offers a well-connected flow between the main living spaces, creating an inviting setting with room to gather, relax, and spread out. Inside, the living room, dining room, and

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (689) 232-3531

  1981 Blue Ridge Rd, Winter Park, FL 32789
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  /25

  $1,800 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Townhouse for Rent

  7473 Belle River Ct Unit 16, Winter Park, FL 32792

  Welcome to this beautiful 3-bedroom, 2.5-bath townhome featuring modern finishes and a serene setting. Enjoy cooking in the kitchen with elegant granite countertops, durable tile flooring downstairs, and stylish luxury vinyl plank flooring upstairs. Step outside to your private fenced patio with peaceful conservation views, perfect for relaxing or entertaining. Available NOW! **All Remi Emerson

  

  Shelley Davis

  REMI EMERSON RESIDENTIAL

  (321) 291-2981

  7473 Belle River Ct Unit 16, Winter Park, FL 32792
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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 $966,525

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
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  Est $131,073 Not Listed For Sale

  1695 Lee Rd Unit E205, Winter Park, FL 32789

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

  1695 Lee Rd Unit E205, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $148/SF
  • 25 Days On Market

  • Last Sold Price $130,000
  • May 09, 2025

  Last Listing Agent Joseph Pacholski KELLER WILLIAMS HERITAGE REALTY
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  $290,000 Pending

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

  5180 Lazy Oaks Dr, Winter Park, FL 32792

  Welcome to your Florida retreat.Whether you’re searching for the perfect first home or looking to downsize into a low-maintenance lifestyle, this single-story end-unit villa offers the ideal blend of comfort, convenience, and charm. With only one shared wall, it lives and feels like a single-family home.The HOA handles all exterior maintenance—including the roof, which was replaced just a

  

  Farzana Zalil

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 221-5173

  5180 Lazy Oaks Dr, Winter Park, FL 32792
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  /55

  Starting at $1,355 Per Month

  • 1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  Cranes Landing Apartments

  (689) 219-5442

  

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  $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 $278,950

  Last Listing Agent Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  Est $596,969 Not Listed For Sale

  777 S Denning Dr Unit B, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,762 Sq Ft
  • Built 2004

  777 S Denning Dr Unit B, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $342/SF
  • 37 Days On Market

  • Last Sold Price $602,500
  • May 09, 2025

  Last Listing Agent Susan Chapin KELLER WILLIAMS WINTER PARK
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  $435,000 Pending

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

  2224 Shadowland Loop, Winter Park, FL 32792

  Under contract-accepting backup offers. **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

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 450-7733

  2224 Shadowland Loop, Winter Park, FL 32792
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  Starting at $1,295 Per Month

  • 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,

  Oak Reserve at Winter Park

  (689) 220-7702

  

  541 Oak Reserve Ln, Winter Park, FL 32792
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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 $1,275,430

  Last Listing Agent Lisa Ratanasirintrawoot CHARLES RUTENBERG REALTY ORLANDO

  1500 Mizell Ave, Winter Park, FL 32789
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  Est $910,339 Not Listed For Sale

  901 Golfside Dr, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 2,392 Sq Ft
  • Built 1969

  901 Golfside Dr, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $385/SF
  • 3 Days On Market

  • Last Sold Price $920,000
  • May 09, 2025

  Last Listing Agent Karen Jacobs COLDWELL BANKER REALTY
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  /35

  $845,000

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

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of electricity....Just ask to see the bill. The premium solar system is PAID OFF with a TRANSFERABLE WARRANTY by manufacturer. This

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 468-9784

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /75

  Starting at $1,416 Per Month

  • 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.

  Bainbridge Winter Park

  (689) 219-8568

  

  1400 Morgan Stanley Ave, Winter Park, FL 32789
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  $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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  Est $403,869 Not Listed For Sale

  3121 Heartwood Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • Built 1981

  3121 Heartwood Ave, Winter Park, FL 32792

  Last Sold Summary

  • $247/SF
  • 31 Days On Market

  • Last Sold Price $402,000
  • May 07, 2025

  Last Listing Agent Thomas Nickley KELLER WILLIAMS REALTY AT THE PARKS
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  /43

  $525,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  720 W Webster Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This home can be purchased with NO INCOME VERIFICATION needed! Welcome to 720 W Webster Avenue, a beautifully renovated home in the heart of historic Carver Town in Winter Park—one of the most sought-after locations in Central Florida. Just a short walk to downtown Winter Park, this charming residence blends

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
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  Starting at $1,637 Per Month

  • 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

  Elon Winter Park

  (689) 219-5245

  

  712 Nicolet Ave, Winter Park, FL 32789
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  $750,000 Sold Jun 09, 2025

  2756 Summerfield Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,740 Sq Ft
  • Built 1967

  Last Sold Summary

  • 3% Above List Price
  • $431/SF
  • 4 Days On Market

  Current Estimated Value $737,981

  Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  Est $519,189 Not Listed For Sale

  1307 Lindenwood Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,612 Sq Ft
  • Built 1960

  1307 Lindenwood Ln, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $326/SF
  • 16 Days On Market

  • Last Sold Price $525,000
  • May 09, 2025

  Last Listing Agent Albin Hubscher CENTRAL FLORIDA PRIME REAL ESTATE LLC
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  /31

  $380,000

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  **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.** Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that offer both comfort and flexibility. Thoughtfully

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  (321) 461-2860

  440 Cambridge Blvd, Winter Park, FL 32789
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  Starting at $1,887 Per Month

  • Studio - 3 Beds

  1305 Morgan Stanley Ave, Winter Park, FL 32789

  Situated in Winter Park near Harry P Leu Gardens, Juno Winter Park brings you urban living at its height. Featuring exquisite studio, one, two, and three-bedroom apartments along with a variety of enviable amenities, our vibrant community invites you to elevate your everyday life. Plus, our prime location just six miles north of downtown Orlando puts you within arm's reach of top-notch shopping,

  Juno Winter Park

  (689) 219-5062

  

  1305 Morgan Stanley Ave, Winter Park, FL 32789
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  $2,295,000 Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Current Estimated Value $2,256,477

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
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  Est $324,983 Not Listed For Sale

  7561 Laurel Springs Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,094 Sq Ft
  • Built 1973

  7561 Laurel Springs Dr, Winter Park, FL 32792

  Last Sold Summary

  • 2% Above List Price
  • $293/SF
  • 18 Days On Market

  • Last Sold Price $320,000
  • May 08, 2025

  Last Listing Agent Carlton Watson Listing Spark South Florida

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