Winter Park, FL Homes

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  $148,000

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft

  151 Lewfield Cir Unit 4, Winter Park, FL 32792

  Enjoy Winter Park lifestyle in this great, first floor, 1 bedroom 1 bath condo. Built in 1973 with a well-planned 678 sq.ft. floor plan. Featuring Laminate flooring, this condo offers a functional and inviting home. The kitchen comes equipped with a range, refrigerator, dishwasher and microwave. The oversized bedroom comes with stackable washer an dryer and two closets. New bedroom window, new

  Susan Tamlin KELLER WILLIAMS REALTY AT THE PARKS

  151 Lewfield Cir Unit 4, Winter Park, FL 32792
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  /15

  $2,000 per month

  • 2 Beds
  • 1.5 Baths
  • 1,091 Sq Ft
  • House for Rent

  2011 Cornell Ave, Winter Park, FL 32789

  Charming 3-Bedroom Home for Rent in Winter Park This charming 3-bedroom, 1-bathroom home has been completely renovated and is available for rent in the heart of Winter Park. The main home offers a functional and comfortable layout, ideal for everyday living. The property also includes a separate efficiency unit and a rear unit, both currently rented and featuring independent entrances, providing

  Andres Ospina Rivera LPT REALTY, LLC

  2011 Cornell Ave, Winter Park, FL 32789
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  $660,000 Sold Apr 14, 2025

  1037 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 3 Baths
  • 2,145 Sq Ft
  • Built 1978

  Last Sold Summary

  • 6% Below List Price
  • $308/SF
  • 29 Days On Market

  Current Estimated Value $656,994

  Last Listing Agent Skip Juma LEGACY REALTY & BROKERS LLC

  1037 Fairway Dr, Winter Park, FL 32792
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  /2

  Est $997,760 Not Listed For Sale

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

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

  311 E Morse Blvd Unit 6-18, Winter Park, FL 32789
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  /5

  $4,595,000

  • Land
  • 0.35 Acre
  • $13,128,571 per Acre

  1336 College Point, Winter Park, FL 32789

  A rare offering on the shores of Lake Virginia, this prime lakefront parcel presents a distinguished opportunity within Winter Park’s most coveted waterfront corridor. Encompassing a significant Lake Virginia homesite on the Winter Park Chain of Lakes, the site currently includes a 1926 structure that may be preserved, redesigned or removed to accommodate a custom waterfront residence. Positioned

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1336 College Point, Winter Park, FL 32789
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  /12

  $1,400 per month

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

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792

  Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

  Damon Mayers MAYERS REAL ESTATE LLC

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
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  /2

  $3,550,000 Sold Mar 24, 2025

  443 Lakewood Dr, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 2,803 Sq Ft
  • Built 1954

  Last Sold Summary

  • 1% Above List Price
  • $1,267/SF
  • 0 Days On Market

  Current Estimated Value $3,313,312

  Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES

  443 Lakewood Dr, Winter Park, FL 32789
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  /36

  Est $1,484,172 Not Listed For Sale

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

  1405 Chapman Cir Unit OR, Winter Park, FL 32789

  1405 Chapman Cir Unit OR, Winter Park, FL 32789
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  /46

  $2,000,000

  • 5 Beds
  • 5 Baths
  • 3,860 Sq Ft

  640 Arjay Way, Winter Park, FL 32789

  Located in one of Winter Park’s most desirable and picturesque neighborhoods, Timberlane Shores, this stunning five-bedroom residence has been recently renovated in an elegant, European style blending timeless character with modern luxury. Situated on over one-third of an acre, the property is accented by majestic oak trees and lush Florida-native landscaping, creating a private and serene

  Farah Bloom KELLER WILLIAMS WINTER PARK

  640 Arjay Way, Winter Park, FL 32789
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  /9

  $702,000 per month

  • Property for Rent

  7839 University Garden Dr, Winter Park, FL 32792

  Build your dream home on 4.93 acres in Winter Park. No HOA, lot dimensions 665ft x 323ft, zoning A-2/FARMLAND RURAL, land use vacant residential. The sale price included 2 parcels 11 22 30 0000 00 125 & 11 22 30 0000 00 042 with a factory home 3/2, 1344 sf. heated, built in 1976, and a mobile home. Convenient to SR-551/ Goldenrod Rd, SR-426/Aloma Rd, SR-50/Colonial Dr, University Blvd, FL-417,

  Shettle Huynh FLORIDA REALTY INVESTMENTS

  7839 University Garden Dr, Winter Park, FL 32792
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  /2

  $468,000 Sold Aug 28, 2025

  541 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,899 Sq Ft
  • Built 1965

  Last Sold Summary

  • $246/SF
  • 8 Days On Market

  Current Estimated Value $473,728

  Last Listing Agent Christopher Bauman REVEL REALTY LLC

  541 London Rd, Winter Park, FL 32792
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  /33

  Est $437,130 Not Listed For Sale

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

  2003 Canny Cove, Winter Park, FL 32792

  2003 Canny Cove, Winter Park, FL 32792
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  /46

  $399,000 Pending

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Enjoy sunrise views over Lake Osceola from this Whispering Waters jewel box, now offered at an improved price of $399,000. This fully renovated one-bedroom, one-bathroom condo spans 900 square feet and offers single-story, ground-floor, corner-unit living just steps from Park Avenue. The 2018 full renovation

  Padgett McCormick KELLY PRICE & COMPANY LLC

  311 E Morse Blvd Unit 7-2, Winter Park, FL 32789
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  /23

  $1,500 per month

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

  1695 Lee Rd Unit B114, Winter Park, FL 32789

  The unit has two spacious bedrooms, galley kitchen, walk in closet, living/dining room combo, washer and dryer combo brand new refrigerator , and lovely patio that leads to the community pool and playground. .This well-maintained unit features a spacious living area filled with natural light Cove is located centrally to major highways, schools, tons of shopping & restaurants so it is a great

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit B114, Winter Park, FL 32789
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  /51

  $704,700 Sold Mar 11, 2025

  350 Carolina Ave Unit 301, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • $456/SF
  • 26 Days On Market

  Current Estimated Value $710,123

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  350 Carolina Ave Unit 301, Winter Park, FL 32789
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  /55

  Est $970,444 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1772 Mondrian Cir, Winter Park, FL 32789

  1772 Mondrian Cir, Winter Park, FL 32789
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  /50

  $1,475,000 Open Sun 9AM - 12PM

  • 4 Beds
  • 3.5 Baths
  • 2,170 Sq Ft

  1751 Goodrich Ave, Winter Park, FL 32789

  Welcome to 1751 Goodrich Ave, a beautifully designed residence in the heart of Winter Park! This 4-bedroom, 3.5-bath home showcases thoughtful contemporary architecture with 10' ceilings on both floors, and an open-concept layout that effortlessly blends style and function. With large double paned windows throughout, this home is drenched with an abundance of natural light. High-end finishes

  Stephanie Baldner EXP REALTY LLC

  1751 Goodrich Ave, Winter Park, FL 32789
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  /17

  $2,000 per month

  • 3 Beds
  • 2 Baths
  • 1,149 Sq Ft
  • Condo for Rent

  1695 Lee Rd Unit E115, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove with 3 bedrooms and 2 bathrooms is a great opportunity to own in Winter Park, close to major highways, shopping, restaurants and so much more. This unit is perfect for lease , brand new paint and flooring ! RENOVATED BATHROOMS! The open living room is spacious and has lots of natural light shining in from the sliding glass doors leading out to the

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit E115, Winter Park, FL 32789
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  /2

  $935,000 Sold Dec 19, 2025

  7706 Waunatta Ct, Winter Park, FL 32792

  • 5 Beds
  • 3 Baths
  • 3,858 Sq Ft
  • Built 1978

  Last Sold Summary

  • 11% Below List Price
  • $242/SF
  • 70 Days On Market

  Last Listing Agent Robert Arnold SAND DOLLAR REALTY GROUP INC

  7706 Waunatta Ct, Winter Park, FL 32792
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  /19

  Est $226,997 Not Listed For Sale

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

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792
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  /19

  $510,000

  • 4 Beds
  • 3 Baths
  • 1,805 Sq Ft

  2627 Ambergate Rd, Winter Park, FL 32792

  Price Reduced !! This beautiful and remodeled home is turnkey and ready to move in!Investors -- You will love the cash flow upside with this property.Updated Roof, AC, Exterior Paint, Patio, Garage, Driveway, Fence, Sprinkler System, Lighting, Flooring, Kitchen, and much more.You will enjoy entertaining your guests with this large saltwater pool with cabana, as well as yard space for

  Ryan Minadie COLDWELL BANKER RESIDENTIAL RE

  2627 Ambergate Rd, Winter Park, FL 32792
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  /2

  $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 $1,154,160

  Last Listing Agent Frank Ferrell FERRELL REALTY, INC.

  233 Hampden Place, Winter Park, FL 32789
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  /43

  Est $762,037 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  7984 Pleasant Pine Cir, Winter Park, FL 32792
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  /9

  $177,000

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

  7444 Woodburn Ct Unit 29, Winter Park, FL 32792

  *** SELLER WILL PAY SPECIAL ASSESSMENT AT CLOSING BRING MONTHLY ASSESSMENT TO $420****Sought after Winter Park Location! 2-bedroom, 2.5-bath townhome located in the desirable Hidden Oaks community. 1,031 sq. ft. newer roof installed in 2023. The exterior is thoughtfully landscaped, enhancing the home’s inviting curb appeal. Conveniently located just: 10 minutes to Downtown Orlando, 15 minutes

  Abranette Lopez LPT REALTY, LLC

  7444 Woodburn Ct Unit 29, 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 $202,707

  Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792
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  /40

  Est $815,222 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,706 Sq Ft

  2035 Soaring Oak Way, Winter Park, FL 32792

  2035 Soaring Oak Way, Winter Park, FL 32792
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  /11

  $198,000

  • 2 Beds
  • 2 Baths
  • 1,062 Sq Ft

  3060 George Mason Ave Unit 12, Winter Park, FL 32792

  Welcome to your new home in Winter Park!Completely remodeled unit with luxury finishes, ceramic floors, modern bathrooms, brand new kitchen with steel appliances and a nice quartz counter. Community amenities include pool, tennis and playground. Great Schools - zoned for Winter Park HS. Just minutes to Full Sail, UCF & Valencia. Don’t miss out on this gem!

  Adriana Sanchez WF REALTY CORP.

  3060 George Mason Ave Unit 12, Winter Park, FL 32792
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  /2

  $292,000 Sold Feb 28, 2025

  2690 Granada Run, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Built 1980

  Last Sold Summary

  • 3% Below List Price
  • $199/SF
  • 33 Days On Market

  Current Estimated Value $294,968

  Last Listing Agent Jacquie Sosa EXP REALTY LLC

  2690 Granada Run, Winter Park, FL 32792
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  /25

  Est $250,000 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft

  5408 Peaco Place, Winter Park, FL 32792

  5408 Peaco Place, Winter Park, FL 32792
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  /32

  $689,500

  • 5 Beds
  • 3.5 Baths
  • 3,152 Sq Ft

  5275 Pine Lily Cir, Winter Park, FL 32792

  Located in desirable Winter Park, this POOL home offers exceptional value. This spacious 5-bedroom plus den area, 3.5-bathroom house has abeautiful pond view from the front door. 3 car garage space and 6 car driveway give you plenty of space for storage and parking. 3,111 squarefeet of comfortable living space plus a gorgeous screened-in pool with spa. The home features high ceilings that

  Kathy Williams REAL BROKER, LLC.

  5275 Pine Lily Cir, 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 $3,169,326

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

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

  Est $1,029,825 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft

  2400 Roxbury Rd, Winter Park, FL 32789

  2400 Roxbury Rd, Winter Park, FL 32789
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  /18

  $1,500,000

  • 4,056 Sq Ft

  1903 S Lakemont Ave, Winter Park, FL 32792

  Location, location, location! This is an amazing opportunity to build/renovate on a premier lakefront lot in the charming and upscale Winter Park neighborhood of Orlando, Florida. Located on Lake Spier and across the street from the beautiful Baldwin Park, this exceptional-almost one acre property-includes six 1/1 units. This prime property is minutes from award winning restaurants, sidewalk

  Maria Tenner Platinum Properties Int'l Inc.

  1903 S Lakemont Ave, Winter Park, FL 32792
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  /2

  $1,850,000 Sold Apr 07, 2025

  2248 Middleton Ave, Winter Park, FL 32792

  • 4 Beds
  • 4.5 Baths
  • 3,505 Sq Ft
  • Built 2025

  Last Sold Summary

  • 2% Below List Price
  • $528/SF
  • 10 Days On Market

  Current Estimated Value $1,803,929

  Last Listing Agent Karen Jacobs COLDWELL BANKER RESIDENTIAL RE

  2248 Middleton Ave, Winter Park, FL 32792
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  /19

  Est $2,596,810 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft

  350 Beloit Ave, Winter Park, FL 32789

  350 Beloit Ave, Winter Park, FL 32789
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  /65

  $4,750,000 New Construction

  • 4 Beds
  • 5.5 Baths
  • 3,850 Sq Ft

  1150 Via Salerno, Winter Park, FL 32789

  In the heart of Winter Park’s coveted Vias neighborhood, 1150 Via Salerno is a newly completed Mediterranean-minimalist residence that blends architectural refinement w/ organic warmth. Designed and developed by Steve and Jodie Warrick Konold of Scout & Co., the 3,850 sf layout offers 4 bedrooms & 5.5 baths, wrapped in the intentional privacy of a luxury retreat. Beyond its terraced walkway and

  Padgett McCormick KELLY PRICE & COMPANY LLC

  1150 Via Salerno, Winter Park, FL 32789
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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

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

  451 Fairfax Ave, Winter Park, FL 32789
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  /35

  Est $292,354 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  228 Balfour Dr Unit 17, Winter Park, FL 32792
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  /67

  $419,000

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

  1900 Erudite Way, Winter Park, FL 32792

  Price Reduced | Best Value in Grayson Square! Step into effortless style and modern comfort in this beautifully crafted 2024 townhome, now priced to sell in Winter Park’s gated Grayson Square community. From the moment you arrive, the home’s sleek curb appeal and smart features set the tone, including keypad entry, smart lighting, and thoughtful upgrades throughout. Inside, the open-concept main

  Erica Diltz BALDWIN PARK REALTY LLC

  1900 Erudite Way, 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 $633,874

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1792 Killarney Dr, Winter Park, FL 32789

Showing Results 601 - 640, Page 16 of 18