Winter Park, FL Homes

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  $489,990

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
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  $2,675 Per Month

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • House for Rent

  1721 Shasta Ct, Winter Park, FL 32792

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  (407) 641-3217

  1721 Shasta Ct, Winter Park, FL 32792
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  $290,000 Sold Nov 24, 2025

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,004 Sq Ft
  • Built 1985

  Last Sold Summary

  • 9% Below List Price
  • $289/SF
  • 54 Days On Market

  Current Estimated Value $286,274

  Last Listing Agent Maria Elena Perez MEP REALTY INVESTMENTS LLC

  2411 Gallery View Dr Unit 5, Winter Park, FL 32792
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  /22

  Est $5,401,250 Not Listed For Sale

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

  • 4 Beds
  • 4.5 Baths
  • 5,430 Sq Ft
  • Built 2005

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

  Last Sold Summary

  • 10% Below List Price
  • $1,104/SF
  • 0 Days On Market

  • Last Sold Price $5,995,000
  • Dec 20, 2023

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY
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  $2,095,000 Pending

  • 3 Beds
  • 4.5 Baths
  • 5,138 Sq Ft

  2820 Bear Island Pointe, Winter Park, FL 32792

  Under contract-accepting backup offers. Tucked behind the gates of Cypress Reserve, this stunning custom-built lakefront home sits on 110 feet of private waterfront along the serene shores of Bear Gully Lake. Inspired by a featured Southern Living plan and thoughtfully expanded, the home blends timeless architecture with generous, well-appointed living spaces — all framed by panoramic water

  Kelly Price KELLY PRICE & COMPANY LLC

  2820 Bear Island Pointe, Winter Park, FL 32792
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  /17

  $2,530 Per Month

  • 3 Beds
  • 2.5 Baths
  • 1,482 Sq Ft
  • House for Rent

  3313 Hamlet Loop, Winter Park, FL 32792

  Please note, our homes are available on a first-come, first-serve basis and are not reserved until the holding fee agreement is signed and the holding fee is paid by the primary applicant.Coming soon! This home is currently being enjoyed by another resident but will be available soon. Please respect their privacy and do not disturb. You can complete the application process and reserve

  (689) 329-3269

  3313 Hamlet Loop, Winter Park, FL 32792
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  $180,000 Sold Feb 27, 2026

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

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft
  • Built 1970

  Last Sold Summary

  • 8% Below List Price
  • $182/SF
  • 11 Days On Market

  Current Estimated Value $183,668

  Last Listing Agent Ingrid Livingston COLDWELL BANKER REALTY

  200 Saint Andrews Blvd Unit 2302, Winter Park, FL 32792
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  /2

  Est $2,743,939 Not Listed For Sale

  1737 Lookout Landing Cir, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 5,066 Sq Ft
  • Built 2013

  1737 Lookout Landing Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $533/SF
  • 232 Days On Market

  • Last Sold Price $2,699,999
  • Oct 15, 2024

  Last Listing Agent Amy Wilson KELLER WILLIAMS REALTY AT THE PARKS
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  /66

  $1,350,000 Pending

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft

  3711 Vinsetta Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  3711 Vinsetta Ct, Winter Park, FL 32792
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  $3,395 Per Month

  • 3 Beds
  • 2 Baths
  • 1,570 Sq Ft
  • House for Rent

  1937 Strathaven Rd, Winter Park, FL 32792

  Property Id: 158416INTERIOR PICTURES COMING SOON * Newly renovated kitchen * All new appliances * All new flooring * Freshly painted * Updated Baths * Open Floor Plan * Large living room * Large sun room * Great Fenced Yard * Includes New Washer / Dryer * Over-sized 2 Car Garage * Great schools * Quite Neighborhood * Rent includes lawn care and pest control

  (689) 220-1342

  1937 Strathaven Rd, Winter Park, FL 32792
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  $580,000 Sold May 16, 2025

  1392 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft
  • Built 2008

  Last Sold Summary

  • 11% Below List Price
  • $300/SF
  • 123 Days On Market

  Current Estimated Value $556,574

  Last Listing Agent Cody Hancock COLDWELL BANKER REALTY

  1392 Indiana Ave, Winter Park, FL 32789
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  Est $202,860 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

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

  Last Sold Summary

  • 12% Below List Price
  • $206/SF
  • 35 Days On Market

  • Last Sold Price $230,000
  • Jun 27, 2023

  Last Listing Agent Robin Delaney KELLER WILLIAMS ADVANTAGE III
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  /23

  $250,000

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft

  7707 Country Place Unit 4, Winter Park, FL 32792

  Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

  Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

  7707 Country Place Unit 4, Winter Park, FL 32792
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  /3

  $2,300 Per Month

  • 3 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • Condo for Rent

  2827 Riddle Dr, Winter Park, FL 32789

  Welcome to your new oasis in the charming city of Winter Park, FL! This beautiful property is perfect for those seeking comfort and convenience in a vibrant community. With nearby restaurants offering a delightful culinary experience, you'll always have something new to explore.This property features spacious accommodations designed for your relaxation. Enjoy a comfortable living

  (321) 381-3659

  2827 Riddle Dr, Winter Park, FL 32789
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  $426,000 Sold Jul 03, 2025

  2028 Sussex Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,674 Sq Ft
  • Built 1973

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 39 Days On Market

  Current Estimated Value $438,699

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

  2028 Sussex Rd, Winter Park, FL 32792
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  Est $726,214 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1960

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

  Last Sold Summary

  • 4% Above List Price
  • $445/SF
  • 75 Days On Market

  • Last Sold Price $700,000
  • Jul 02, 2024

  Last Listing Agent Scott Garstka CHARLES RUTENBERG REALTY ORLANDO
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  /54

  $1,950,000

  • 4 Beds
  • 3.5 Baths
  • 3,307 Sq Ft

  2614 Parkland Dr, Winter Park, FL 32789

  Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of

  Ryan Gaston JW GASTON LLC

  2614 Parkland Dr, Winter Park, FL 32789
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  /6

  $1,950 Per Month

  • 1 Bed
  • 1 Bath
  • Condo for Rent

  520 Holt Ave, Winter Park, FL 32789

  Property Id: 578482One-bedroom / one-bathroom cottage style apartment located within a five-minute walk to Rollins College, Park Avenue, and Hannibal Square. Newly-renovated interior includes condominium grade appliances, upgraded bathroom, and in-unit washer dryer. Unit includes off-street parking and private entry porch. Available for lease beginning of June 2026. Rent includes

  (321) 304-2205

  520 Holt Ave, Winter Park, FL 32789
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  $4,772,500 Sold Sep 18, 2025

  765 Via Lugano, Winter Park, FL 32789

  • 4 Beds
  • 4.5 Baths
  • 4,319 Sq Ft
  • Built 2019

  Last Sold Summary

  • $1,105/SF
  • 1 Day On Market

  Current Estimated Value $4,664,184

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

  765 Via Lugano, Winter Park, FL 32789
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  Est $1,305,246 Not Listed For Sale

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,734 Sq Ft
  • Built 2009

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  Last Sold Summary

  • 10% Below List Price
  • $530/SF
  • 3 Days On Market

  • Last Sold Price $1,450,000
  • May 20, 2024

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC
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  $1,250,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,525 Sq Ft

  1870 Staunton Ave, Winter Park, FL 32789

  Pre-Construction. To be built. Discover a rare opportunity to build a fully custom residence in the highly sought-after Killarney Shores neighborhood of Winter Park—one of the last areas where new construction at this level remains attainable below $1.3M. Exclusively curated by The Hope Group, this offering pairs premier design with a seamless build experience alongside Deep Roots Construction,

  Vinny Lay COMPASS FLORIDA LLC

  1870 Staunton Ave, Winter Park, FL 32789
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  /20

  $2,385 Per Month

  • 3 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • House for Rent

  2313 Dunbury Ct, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2529.90. That covers your base rent, $2385.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  (321) 205-9980

  2313 Dunbury Ct, Winter Park, FL 32792
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  $3,100,000 Sold Jun 27, 2025

  731 Williams Dr, Winter Park, FL 32789

  • 5 Beds
  • 6 Baths
  • 4,260 Sq Ft
  • Built 2025

  Last Sold Summary

  • 6% Below List Price
  • $728/SF
  • 45 Days On Market

  Current Estimated Value $2,939,252

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  731 Williams Dr, Winter Park, FL 32789
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  Est $930,692 Not Listed For Sale

  1245 Wisconsin Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,610 Sq Ft
  • Built 2013

  1245 Wisconsin Ave, Winter Park, FL 32789

  Last Sold Summary

  • 11% Above List Price
  • $322/SF
  • 51 Days On Market

  • Last Sold Price $840,000
  • Sep 30, 2024

  Last Listing Agent Emily Bearden COMPASS FLORIDA LLC
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  /31

  $267,000 Pending

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

  1500 Gay Rd Unit 8D, Winter Park, FL 32789

  Welcome to the most beautifully updated 2 Bedroom 2 bath End Unit in a Lakefront Community on Lake Killarney. This home features Quartz counter tops with a Granite Island and stainless steel appliances, along with a beverage refrigerator, and luxury vinyl flooring through out the whole unit. A huge living room offers loads of gathering and entertaining space in this cheerful home. Enjoy Florida

  Trevor Laug. Realtor SOLID OAK REAL ESTATE LLC

  1500 Gay Rd Unit 8D, Winter Park, FL 32789
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  $2,645 Per Month

  • 4 Beds
  • 2 Baths
  • 1,646 Sq Ft
  • House for Rent

  2141 Ridge Dr, Winter Park, FL 32792

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $40/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  (689) 220-1676

  2141 Ridge Dr, Winter Park, FL 32792
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  $2,700,000 Sold Oct 02, 2025

  1445 Holts Grove Cir, Winter Park, FL 32789

  • 5 Beds
  • 5 Baths
  • 4,489 Sq Ft
  • Built 2002

  Last Sold Summary

  • 2% Above List Price
  • $601/SF
  • 2 Days On Market

  Current Estimated Value $2,654,470

  Last Listing Agent Shelley Heistand PREMIER SOTHEBY'S INTL. REALTY

  1445 Holts Grove Cir, Winter Park, FL 32789
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  Est $194,845 Not Listed For Sale

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1984

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $209/SF
  • 6 Days On Market

  • Last Sold Price $213,000
  • Aug 17, 2023

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC
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  $399,000 Pending

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

  2834 Bright Bird Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. Priced BELOW appraised value for a quick sale! Welcome to this stunning newer-construction townhome offering modern design, spacious living, and unbeatable value in one of Orlando’s most convenient locations. Featuring 3 bedrooms, 3 bathrooms, and nearly 2,000 sq ft of living space, this home boasts an open-concept layout, contemporary finishes, and

  Irene Navarro LIFESTYLE INTERNATIONAL REALTY

  2834 Bright Bird Ln, Winter Park, FL 32792
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  /18

  $1,890 Per Month

  • 2 Beds
  • 3 Baths
  • 1,400 Sq Ft
  • Townhouse for Rent

  7290 Daniel Webster Dr, Winter Park, FL 32792

  Property Id: 2485692The house is large and comfortable.it has two garden and transport and college university and supermarket and discount

  (786) 396-6891

  7290 Daniel Webster Dr, Winter Park, FL 32792
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  $375,000 Sold Dec 30, 2025

  3083 Crane Strand Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1972

  Last Sold Summary

  • $312/SF
  • 12 Days On Market

  Current Estimated Value $370,832

  Last Listing Agent Sheri Malin REDFIN CORPORATION

  3083 Crane Strand Dr, Winter Park, FL 32792
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  Est $135,256 Not Listed For Sale

  289 Lewfield Cir, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 678 Sq Ft
  • Built 1973

  289 Lewfield Cir, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $211/SF
  • 58 Days On Market

  • Last Sold Price $143,000
  • Oct 11, 2024

  Last Listing Agent Christopher Courtney DENIZ REALTY PARTNERS LLC
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  $1,030,000

  • 3 Beds
  • 2.5 Baths
  • 2,578 Sq Ft

  1541 Westchester Ave, Winter Park, FL 32789

  Set on over half an acre in Winter Park’s coveted Orwin Manor, this 1935 French Provincial estate offers a rare blend of architectural character, modern system updates, and extraordinary future potential. The property offers the unique opportunity to own an estate in a beautifully historic Winter Park neighborhood. Whether thoughtfully renovated, expanded, or reimagined, this property stands as a

  Lisa Gould KELLER WILLIAMS WINTER PARK

  1541 Westchester Ave, Winter Park, FL 32789
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  $3,025 Per Month

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft
  • House for Rent

  504 St Dunstan Way, Winter Park, FL 32792

  We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be happy to help you find a different home or refund your Hold Fee. This home

  (321) 339-1052

  504 St Dunstan Way, Winter Park, FL 32792
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  $560,000 Sold Aug 20, 2025

  1901 Loch Berry Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,420 Sq Ft
  • Built 1957

  Last Sold Summary

  • 1% Below List Price
  • $394/SF
  • 7 Days On Market

  Current Estimated Value $537,712

  Last Listing Agent Monica Tipirneni FOLIO REALTY LLC

  1901 Loch Berry Rd, Winter Park, FL 32792
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  Est $213,145 Not Listed For Sale

  220 Lewfield Cir, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,300 Sq Ft
  • Built 1973

  220 Lewfield Cir, Winter Park, FL 32792

  Last Sold Summary

  • 15% Below List Price
  • $192/SF
  • 109 Days On Market

  • Last Sold Price $249,900
  • Feb 09, 2024

  Last Listing Agent Alex Galitsky TOP ORLANDO REALTY
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  /20

  $205,000

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

  This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

  Manny Celi YOUNG REAL ESTATE

  3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
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  /20

  $2,726

  Total Monthly Price

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789

  The advertised rate of $2,726/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 26, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can

  (321) 483-3204

  662 Callahan St Unit SI ID1308311P, Winter Park, FL 32789
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  $916,000 Sold Jul 17, 2025

  609 Langholm Dr, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,981 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $462/SF
  • 8 Days On Market

  Current Estimated Value $904,622

  Last Listing Agent Jason Shore JMO REAL ESTATE GROUP

  609 Langholm Dr, Winter Park, FL 32789
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  Not Listed For Sale

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1974

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  Last Sold Summary

  • $115/SF
  • 81 Days On Market

  • Last Sold Price $145,500
  • Jan 05, 2024

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

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