Winter Park, FL Homes

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  /40

  $2,200,000

  • 4 Beds
  • 3.5 Baths
  • 3,195 Sq Ft

  872 Granville Dr, Winter Park, FL 32789

  A rare offering in the highly sought-after Park Grove neighborhood, this expertly redesigned 4-bedroom residence blends elevated design with effortless everyday living. Originally renovated by award-winning interior designer John McClain and recognized with first-place honors in 2020, the home reflects a refined balance of style and functionality.??Ideally located just moments from Park Avenue

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 485-7250

  872 Granville Dr, Winter Park, FL 32789
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  /53

  $1,635 - $9,294 per month

  Juno Winter Park

  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,

  1305 Morgan Stanley 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 $739,041

  Last Listing Agent Alexis Davis FANNIE HILLMAN & ASSOCIATES

  2756 Summerfield Rd, Winter Park, FL 32792
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  /2

  Est $336,495 Not Listed For Sale

  5331 Binnacle Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1973

  5331 Binnacle Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $274/SF
  • 21 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Edwin Nieves CHARLES RUTENBERG REALTY ORLANDO
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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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  $2,295,000 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 $2,222,050

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
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  Est $531,954 Not Listed For Sale

  2019 Loch Berry Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,425 Sq Ft
  • Built 1957

  2019 Loch Berry Rd, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $368/SF
  • 7 Days On Market

  Last Sold Price $525,000

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES
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  /43

  $550,000

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

  720 W Webster Ave, Winter Park, FL 32789

  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 modern updates with timeless character

  

  Vincent Cordaro

  SERHANT

  (321) 341-3712

  720 W Webster Ave, Winter Park, FL 32789
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  /103

  $1,807 - $6,390 per month

  Paseo at Winter Park Village

  1 - 3 Beds

  940 W Canton Ave, Winter Park, FL 32789

  Ready for an apartment home that truly feels like home? With upscale finishes and modern amenities, Paseo's units are ready to welcome you. You (and your pet!) can relax in our palm-lined courtyard, lounge by the pool, or play in our on-site dog park. With the shopping of Winter Park Village, movies at the Regal Cinema, and the historic downtown all close by, there are endless opportunities to

  940 W Canton Ave, Winter Park, FL 32789
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  /2

  $2,700,000 Sold Oct 30, 2025

  1020 Mayfield Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,663 Sq Ft
  • Built 1989

  Last Sold Summary

  • 15% Below List Price
  • $1,014/SF
  • 149 Days On Market

  Current Estimated Value $2,594,633

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  1020 Mayfield Ave, Winter Park, FL 32789
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  /42

  Est $441,555 Not Listed For Sale

  1061 Lundy Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1984

  1061 Lundy Ct, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $345/SF
  • 32 Days On Market

  Last Sold Price $465,000

  Last Listing Agent Ahmad Hassan COMPASS FLORIDA LLC
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  /8

  $260,000 Pending

  • Land
  • 0.81 Acre
  • $320,988 per Acre

  3580 Wilde Ave, Winter Park, FL 32792

  Discover the ideal spot for your dream home on this cleared, ready-to-build spacious, just shy of an acre, lot in coveted Winter Park. Nestled on a quiet cul-de-sac yet situated minutes to Park Avenue boutique shops and restaurants (5.2 mi. away), Dinky Dock public boat ramp (5 mi.), and 3 local universities - Rollins (5.2 mi.), UCF (5.5 mi.) and Full Sail (1.6 mi.). A cleared and level lot on a

  

  Gwendolen Flynn

  COLDWELL BANKER REALTY

  (321) 334-2867

  3580 Wilde Ave, Winter Park, FL 32792
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  /25

  $2,500 per month

  • 3 Beds
  • 1.5 Baths
  • 1,279 Sq Ft
  • House for Rent

  2846 Euston Rd, Winter Park, FL 32789

  Welcome to a true Mid-Century rental in Winter Park located in the quaint neighborhood of Fairbank Shores. Spacious 2 bedrooms and 1.5 bath home with 1 extra flexible room that can be used as an office or 3rd bedroom(no closet). Centrally located, minutes form I4, close to Park Avenue District, College Park, major shopping centers and many more. Big backyard with a nice sized paved courtyard and

  Vanessa Laboy 365 REALTY, INC.

  2846 Euston Rd, Winter Park, FL 32789
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  $714,000 Sold Mar 12, 2026

  636 Dunblane Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,803 Sq Ft
  • Built 1962

  Last Sold Summary

  • 2% Below List Price
  • $396/SF
  • 7 Days On Market

  Current Estimated Value $710,703

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  636 Dunblane Dr, Winter Park, FL 32792
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  Est $1,229,585 Not Listed For Sale

  2258 Howard Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,747 Sq Ft
  • Built 1953

  2258 Howard Dr, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $457/SF
  • 30 Days On Market

  Last Sold Price $1,255,000

  Last Listing Agent Greysy Ysea NAIM REAL ESTATE LLC
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  /21

  $255,000

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

  1500 Gay Rd Unit 18A, Winter Park, FL 32789

  REDUCED! Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard and Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has Cabinets matching those in Kitchen and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 449-7958

  1500 Gay Rd Unit 18A, Winter Park, FL 32789
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  /36

  $1,233 - $1,809 per month

  Seabrook

  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

  3114 Terry Brook Dr, Winter Park, FL 32792
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  $4,100,000 Sold Apr 18, 2025

  1691 Chestnut Ave, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 4,582 Sq Ft
  • Built 2024

  Last Sold Summary

  • 15% Below List Price
  • $895/SF
  • 1 Day On Market

  Current Estimated Value $4,040,574

  Last Listing Agent Sue Silberbusch COMPASS FLORIDA LLC

  1691 Chestnut Ave, Winter Park, FL 32789
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  Est $583,848 Not Listed For Sale

  336 Saint Dunstan Way, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,715 Sq Ft
  • Built 1964

  336 Saint Dunstan Way, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $350/SF
  • 335 Days On Market

  Last Sold Price $600,000

  Last Listing Agent David Auerbach PARK TOWN REAL ESTATE LLC
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  /19

  $179,700

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792

  Beautifully updated condo in a prime Winter Park location! This move-in ready unit features a beautifully renovated kitchen, updated bathrooms, and tile flooring throughout, offering a modern and low-maintenance living space. Ideally situated on South Semoran Blvd, you’ll love the convenience of being just minutes to Baldwin Park, Full Sail University, UCF, and Downtown Winter Park, with easy

  

  Carrie Shawfield

  SHAWFIELD REALTY GROUP

  (321) 334-3379

  1000 S Semoran Blvd Unit 805, Winter Park, FL 32792
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  /15

  $3,600 per month

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • House for Rent

  1461 Lone Feather Trail, Winter Park, FL 32792

  Beautiful newer two-story home in Winter Park’s exclusive Gated community of Hawk’s Crest. Community has lake access with canon launch. The home has a great floor plan that features open dining and living rooms. Mastered room is conveniently located on the first floor. also Study room. This gated community features a resort style swimming pool, fitness center, splash pad, clubhouse, playgrounds,

  Steve Kim MARVIEW INTERNATIONAL REALTY LLC

  1461 Lone Feather Trail, Winter Park, FL 32792
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  $638,250 Sold Sep 02, 2025

  1536 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,888 Sq Ft
  • Built 1980

  Last Sold Summary

  • $338/SF
  • 3 Days On Market

  Current Estimated Value $633,355

  Last Listing Agent Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1536 Golfside Dr, Winter Park, FL 32792
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  /2

  Est $886,530 Not Listed For Sale

  533 Balmoral Rd, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 1,900 Sq Ft
  • Built 1957

  533 Balmoral Rd, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $476/SF
  • 3 Days On Market

  Last Sold Price $905,000

  Last Listing Agent Molly Nichols CHARLES RUTENBERG REALTY ORLANDO
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  /19

  $225,000

  • 3 Beds
  • 2 Baths
  • 1,230 Sq Ft

  7706 Country Place Unit A8, Winter Park, FL 32792

  Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

  

  Carmen Vazquez

  REALTY TECH INC

  (321) 339-0107

  7706 Country Place Unit A8, Winter Park, FL 32792
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  $1,574 - $5,505 per month

  Vintage Winter Park Apartments

  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.

  7490 Dwell Well Way, Winter Park, FL 32792
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  $401,000 Sold Oct 15, 2025

  1809 Palmer Ave, Winter Park, FL 32792

  • Land
  • 0.21 Acre
  • $1,909,524 per Acre

  Last Sold Summary

  • 5 Days On Market

  Current Estimated Value $391,440

  Last Listing Agent Christina Munkberg COLDWELL BANKER REALTY

  1809 Palmer Ave, Winter Park, FL 32792
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  /2

  Est $439,320 Not Listed For Sale

  1663 Meadowgold Ct, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,851 Sq Ft
  • Built 1987

  1663 Meadowgold Ct, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $240/SF
  • 173 Days On Market

  Last Sold Price $445,000

  Last Listing Agent Dallas Wittish ORLANDO REALTY & PROPERTY MGNT
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  /43

  $830,000 Open Sat 10AM - 2PM

  • 4 Beds
  • 3.5 Baths
  • 3,020 Sq Ft

  1183 Wildmeadow Run, Winter Park, FL 32792

  Welcome to this original-owner residence in The Meadows at Hawk’s Crest, where thoughtful design and exceptional privacy come together—featuring two true primary suites, one on the first floor and one on the second. Set on an oversized fenced homesite along a quiet non-thru street with no neighbor to the east, this beautifully maintained 4-bedroom, 3.5-bath home offers over 3,020 sq.ft. of living

  

  Kara Lushear

  COLDWELL BANKER REALTY

  (321) 621-0024

  1183 Wildmeadow Run, Winter Park, FL 32792
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  /17

  $1,350 per month

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

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. The 1 bed, 1 bath unit is ideally located in Winter Park, close to Full Sail and UCF. Rent includes water, and all appliances including washer & dryer. A spacious Living/Dining space and a Huge bedroom make this the best one bed/one bath you'll find. You're just a short drive from downtown and other Orlando hotspots. Wrenwood is a very quiet

  Torey Eisenman BENCHMARK REAL ESTATE GRP INC

  4818 Tangerine Ave Unit 4818, Winter Park, FL 32792
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  $775,000 Sold May 21, 2025

  1818 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2018

  Last Sold Summary

  • 6% Below List Price
  • $342/SF
  • 189 Days On Market

  Current Estimated Value $797,659

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1818 Mondrian Cir, Winter Park, FL 32789
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  /23

  Est $231,232 Not Listed For Sale

  7729 Country Place Unit G4, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,068 Sq Ft
  • Built 1982

  7729 Country Place Unit G4, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $248/SF
  • 4 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Michael Gangemi CALL IT CLOSED INTL REALTY
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  /40

  $2,650,000 Open Sun 1PM - 3PM

  • 5 Beds
  • 3.5 Baths
  • 4,011 Sq Ft

  1130 Park North Place, Winter Park, FL 32789

  Located on a quiet cul-de-sac in the heart of Winter Park, this traditional two-story home offers a functional, well-designed floorplan for both everyday living and entertaining. From the moment you step inside, the home has an inviting warmth that you can immediately feel. The main level features a spacious primary suite along with connected living spaces that flow easily from room to room. The

  

  Jennifer King

  CORCORAN PREMIER REALTY

  (321) 257-9480

  1130 Park North Place, Winter Park, FL 32789
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  $1,412 - $2,026 per month

  Cranes Landing Apartments

  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

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  $690,000 Sold Aug 14, 2025

  2433 Whitehall Cir, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,841 Sq Ft
  • Built 1962

  Last Sold Summary

  • 5% Above List Price
  • $375/SF
  • 2 Days On Market

  Current Estimated Value $651,402

  Last Listing Agent Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2433 Whitehall Cir, Winter Park, FL 32792
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  /2

  Est $560,941 Not Listed For Sale

  1860 Linden Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,820 Sq Ft
  • Built 1957

  1860 Linden Rd, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $311/SF
  • 36 Days On Market

  Last Sold Price $566,000

  Last Listing Agent Kathy Williams REAL BROKER, 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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  /18

  $2,167 per month

  • 4 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • House for Rent

  717 Denton Rd, Winter Park, FL 32792

  Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  717 Denton Rd, Winter Park, FL 32792
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  /2

  $555,000 Sold Apr 25, 2025

  633 London Rd, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft
  • Built 1966

  Last Sold Summary

  • 2% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $552,094

  Last Listing Agent Barry Sanford PA CHARLES RUTENBERG REALTY ORLANDO

  633 London Rd, Winter Park, FL 32792
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  /45

  Est $316,542 Not Listed For Sale

  7319 Blue Jacket Place W, Winter Park, FL 32792

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

  7319 Blue Jacket Place W, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $288/SF
  • 5 Days On Market

  Last Sold Price $322,000

  Last Listing Agent Jennah LeBruno, LLC RE/MAX

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