Winter Park, FL Homes

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  $1,195,000

  • 4 Beds
  • 3 Baths
  • 2,723 Sq Ft

  220 W Reading Way, Winter Park, FL 32789

  Set on an approximately one-quarter acre homesite in a desirable Winter Park location, this property presents an exceptional opportunity to build a custom residence in one of Central Florida’s most sought-after communities. The existing property features a one-story pool home offering approximately 2,723 heated square feet with four bedrooms and three baths; however, the value is primarily in the

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  220 W Reading Way, Winter Park, FL 32789
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  $1,650 Per Month

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Condo for Rent

  625 Trinidad Ct Unit 625, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Move right into this CLEAN & WELL-MAINTAINED 2 BEDROOM / 2 BATH ONE-STORY CONDO offering 1,037 SF OF COMFORTABLE LIVING SPACE in the heart of WINTER PARK! This MOVE-IN READY home features a SPACIOUS LAYOUT, NATURAL LIGHT, and a functional floor plan perfect for comfortable everyday living. Enjoy a SMALL & COZY BACKYARD PATIO AREA, perfect for

  Nydia Marrero ZEN LIVING HOMES LLC

  625 Trinidad Ct Unit 625, Winter Park, FL 32792
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  $699,000 Sold Jun 30, 2025

  1632 Haven Dr, Orlando, FL 32803

  • 3 Beds
  • 2.5 Baths
  • 1,772 Sq Ft
  • Built 2025

  Last Sold Summary

  • 3% Below List Price
  • $394/SF
  • 110 Days On Market

  Current Estimated Value $496,000

  Last Listing Agent Robert St. Pierre WEEKLEY HOMES REALTY COMPANY

  1632 Haven Dr, Orlando, FL 32803
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  Est $798,898 Not Listed For Sale

  2255 Marsh Sedge Ln, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 2020

  2255 Marsh Sedge Ln, Winter Park, FL 32792

  Last Sold Summary

  • $365/SF
  • 0 Days On Market

  • Last Sold Price $800,000
  • Apr 21, 2025

  Last Listing Agent Raymond Lopez KELLER WILLIAMS ADVANTAGE 2 REALTY
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  $475,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,117 Sq Ft

  1923 Linden Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. ***WINTER PARK **** 4 BEDROOMS ****3 BATHROOM **** PAID OFF SOLAR ***** WILL HELP BUYER****METAL ROOF ***1/3 ACRE*** Welcome to 1923 Linden Rd, Winter Park—a well-maintained single-story residence offering space, character, and an exceptional location. Built in 1955, this solid masonry and concrete block home features 4 bedrooms, 3 full bathrooms, and

  Milton James COLDWELL BANKER REALTY

  1923 Linden Rd, Winter Park, FL 32792
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  $2,095 Per Month

  • 3 Beds
  • 2 Baths
  • House for Rent

  5139 Oak Hill Dr, Winter Park, FL 32792

  3/2 home with updated kitchen, large yard & screen patio. 3/2 home with updated kitchen, large yard & screen patio. Lawn service included

  5139 Oak Hill Dr, Winter Park, FL 32792
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  $689,500 Sold Jul 19, 2025

  1129 Golfside Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $394/SF
  • 21 Days On Market

  Current Estimated Value $673,583

  Last Listing Agent Tess Muccigrosso RE/MAX 200 REALTY

  1129 Golfside Dr, Winter Park, FL 32792
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  Est $431,087 Not Listed For Sale

  1935 Canny Cove, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2023

  1935 Canny Cove, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $236/SF
  • 60 Days On Market

  • Last Sold Price $450,000
  • Oct 17, 2024

  Last Listing Agent Nick Lally COMPASS FLORIDA LLC
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  $849,000

  • 4 Beds
  • 2 Baths
  • 1,617 Sq Ft

  1780 Bryan Ave, Winter Park, FL 32789

  Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value.The lot’s generous dimensions

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
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  $6,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 2,531 Sq Ft
  • House for Rent

  1441 Oneco Ave, Winter Park, FL 32789

  Gorgeous Modern Home with 4 bedrooms + 3 and a half bath home with numerous upgrades throughout located in desirable Winter Park. This house has a large kitchen that opens to the family room for entertaining. Fantastic kitchen with solid wood cabinets, granite counters, walk-in pantry, stainless appliances, Gas 5 burner stove, built-in microwave, large island, big windows emanating a lot of

  Wendy Calvet OLDE TOWN BROKERS INC

  1441 Oneco Ave, Winter Park, FL 32789
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  $893,000 Sold Oct 09, 2025

  2890 Wild Ginger Ct, Winter Park, FL 32792

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft
  • Built 1993

  Last Sold Summary

  • 27% Below List Price
  • $262/SF
  • 78 Days On Market

  Current Estimated Value $892,310

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

  2890 Wild Ginger Ct, Winter Park, FL 32792
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  Est $784,021 Not Listed For Sale

  1421 Wooddale Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,628 Sq Ft
  • Built 1950

  1421 Wooddale Ave, Winter Park, FL 32789

  Last Sold Summary

  • 16% Above List Price
  • $416/SF
  • 45 Days On Market

  • Last Sold Price $678,000
  • Oct 31, 2024

  Last Listing Agent Rafael Casallas, Pa EMPIRE NETWORK REALTY
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  $269,000

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft

  3220 Netherwood Dr, Winter Park, FL 32792

  Welcome home to this fully renovated 2-bedroom, 1.5-bath residence! This home features a brand-new kitchen, new flooring throughout, and beautifully updated bathrooms. Nestled in a quiet neighborhood, it offers a large backyard—perfect for outdoor entertaining or future expansion. Ideal for a first-time homebuyer or anyone seeking stress-free living. Best of all, NO HOA! Conveniently located near

  Nimrah Ashraf THE FIRM RE

  3220 Netherwood Dr, Winter Park, FL 32792
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  $2,695 Per Month

  • 3 Beds
  • 2 Baths
  • 1,444 Sq Ft
  • House for Rent

  3897 Waterview Loop, Winter Park, FL 32792

  Welcome to 3897 Waterview Loop in beautiful Winter Park, FL. When you first walk into this amazing home you are immediately greeted with an open airy feeling by the vaulted ceiling and dual skylights. The open concept living and dining rooms have plenty of space for entertainment and family dinners. The kitchen features all stainless-steel appliances and granite counter tops. Adjacent to the

  3897 Waterview Loop, Winter Park, FL 32792
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  $800,200 Sold Oct 03, 2025

  4107 Gabriella Ln, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 3,074 Sq Ft
  • Built 1998

  Last Sold Summary

  • 33% Below List Price
  • $260/SF
  • 112 Days On Market

  Current Estimated Value $966,076

  Last Listing Agent Barrett Spray KELLER WILLIAMS ADVANTAGE REALTY

  4107 Gabriella Ln, Winter Park, FL 32792
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  Est $307,644 Not Listed For Sale

  5804 Shale Ct, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Built 1985

  5804 Shale Ct, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $308/SF
  • 3 Days On Market

  • Last Sold Price $325,000
  • Aug 30, 2024

  Last Listing Agent Mario Zendeli COMPASS FLORIDA LLC
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  $179,000 Pending

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 122, Winter Park, FL 32789

  Under contract-accepting backup offers. PRICE IMPROVEMENT! Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern

  Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

  2500 Lee Rd Unit 122, Winter Park, FL 32789
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  $4,000 Per Month

  • 4 Beds
  • 2.5 Baths
  • 2,196 Sq Ft
  • House for Rent

  1091 Wildmeadow Run, Winter Park, FL 32792

  Newer home for rent in the gated new community of Hawks Crest. The home offers both style and flexibility. The first floor is graced with an openness that invites you in and makes you feel welcome. The plan features options to help you personalize the home to your needs and preferences. Entering the home, you walk into an expansive space. A flex room with 2-story ceiling can be used as a formal

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1091 Wildmeadow Run, Winter Park, FL 32792
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  $396,477 Sold May 20, 2025

  7543 Dockside St, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,434 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Above List Price
  • $276/SF
  • 7 Days On Market

  Current Estimated Value $400,602

  Last Listing Agent Juan Matias LPT REALTY, LLC

  7543 Dockside St, Winter Park, FL 32792
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  Not Listed For Sale

  677 Grenadine Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1981

  677 Grenadine Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • $207/SF
  • 103 Days On Market

  • Last Sold Price $215,000
  • Nov 04, 2024

  Last Listing Agent Barbara Zapotocky RE/MAX
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  $625,000

  • 3 Beds
  • 2 Baths
  • 1,785 Sq Ft

  2708 Lion Heart Rd, Winter Park, FL 32792

  Welcome to 2708 Lion Heart Rd, where timeless charm meets modern elegance in the heart of Winter Park. This beautifully reimagined home has been thoughtfully renovated from top to bottom, offering a seamless blend of style, comfort, and functionality. Step inside to discover brand-new luxury vinyl plank flooring flowing throughout, creating a warm and cohesive feel in every room. The stunning

  Navid Rokh EQUITYPRO LLC

  2708 Lion Heart Rd, Winter Park, FL 32792
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  $1,595 Per Month

  • 2 Beds
  • 1 Bath
  • 881 Sq Ft
  • SPACIOUS 2BR CONDO | MOVE-IN READY | LIMITED AVAILABILITY

  1695 Lee Rd, Winter Park, FL 32789

  Beautiful and move-in ready 2 Bedroom / 1 Bathroom condo located on the second floor in a quiet, well-maintained community.This unit offers the perfect combination of comfort, space, and convenience — ideal for families or professionals looking for a clean and functional home ready for immediate move-in.PROPERTY HIGHLIGHTS:2 Bedrooms / 1 Full Bathroom - Second-floor unit

  1695 Lee Rd, Winter Park, FL 32789
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  $3,020,000 Sold Oct 02, 2025

  1820 Englewood Rd, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,263 Sq Ft
  • Built 2015

  Last Sold Summary

  • 8% Below List Price
  • $708/SF
  • 70 Days On Market

  Current Estimated Value $3,004,771

  Last Listing Agent David Hung KELLER WILLIAMS ADVANTAGE III

  1820 Englewood Rd, Winter Park, FL 32789
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  Est $266,035 Not Listed For Sale

  7164 Swallow Run Unit GE, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,470 Sq Ft
  • Built 2012

  7164 Swallow Run Unit GE, Winter Park, FL 32792

  Last Sold Summary

  • 8% Below List Price
  • $197/SF
  • 13 Days On Market

  • Last Sold Price $290,000
  • Aug 09, 2024

  Last Listing Agent Christian Cruz Garayua CENTURY 21 NEXT LEVEL REALTY
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  $724,900 Pending

  • 4 Beds
  • 2 Baths
  • 1,599 Sq Ft

  688 Brechin Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. Discover one of the sought-after communities in Winter Park, Kenilworth Shores, where mature oak trees frame the streets, spacious parks serve as gathering ground for families and peaceful walking trails weave through the neighborhood. Centrally within arm’s reach of luxury shopping on Park Avenue in Winter Park, stunning lake views and parks in Baldwin

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  688 Brechin Dr, Winter Park, FL 32792
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  $2,195 Per Month

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • House for Rent

  5523 Cretan Way, Winter Park, FL 32792

  3 bedroom, 2 bathroom townhouse in highly desired Winter Park. Small and quiet neighborhood with private driveway parking and a cul de sac with no neighbors on one side. Amenities include: central air, central heat, dishwasher, garbage disposal, side-by-side fridge, electric stove/oven, gas grill, Maytag full-size washer/dryer set, yard, shed for storage, and mini bar off of the living room, and

  Shawn Beard RE/MAX 200 REALTY

  5523 Cretan Way, Winter Park, FL 32792
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  $1,120,000 Sold Jan 08, 2026

  5236 Lake Howell Rd, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,710 Sq Ft
  • Built 2025

  Last Sold Summary

  • 23% Below List Price
  • $302/SF
  • 129 Days On Market

  Current Estimated Value $1,074,766

  Last Listing Agent Troy Hensley BHHS FLORIDA REALTY

  5236 Lake Howell Rd, Winter Park, FL 32792
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  Not Listed For Sale

  681 Grenadine Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,037 Sq Ft
  • Built 1981

  681 Grenadine Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • $191/SF
  • 147 Days On Market

  • Last Sold Price $198,000
  • Dec 02, 2024

  Last Listing Agent Reinaldo Roman ROMAN'S PRO REALTY LLC
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  $4,200,000

  • Land
  • 14,810 Sq Ft
  • $12,352,941 per Acre

  1298 Beachview Ave, Winter Park, FL 32789

  This is a rare Lake Killarney portfolio offering of four parcels in Winter Park. An exceptional opportunity to acquire a four-parcel assemblage in one of Winter Park’s most coveted locations, just moments from the shores of Lake Killarney. This offering includes 1321 Fairview Ave. and 230 and 240 Killarney Drive, all with potential for private dock access, and a desirable live/work parcel on 1298

  Shandy Ortiz PREMIER SOTHEBYS INT'L REALTY

  1298 Beachview Ave, Winter Park, FL 32789
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  $1,900 Per Month

  • 2 Beds
  • 2.5 Baths
  • 960 Sq Ft
  • Gorgeous, Completely Remodeled 2/2.5 Condo in Sandlewood Creek- Winter Park!

  303 Sandlewood Trail, Winter Park, FL 32789

  Welcome home to this beautifully renovated two-story condo in desirable Sandlewood Trails. This 2-Bedroom, 2.5 Bath condo home is ideally located in Winter Park and is one of the few condo communities where residents are close enough to bike or walk to Dommerich Elementary and Maitland Middle School.As you enter, you are welcomed by a spacious Great Room and attractive gray-toned laminate

  303 Sandlewood Trail, Winter Park, FL 32789
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  $423,000 Sold Aug 07, 2025

  2812 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2024

  Last Sold Summary

  • 8% Below List Price
  • $222/SF
  • 87 Days On Market

  Current Estimated Value $431,251

  Last Listing Agent Jessica Snyder LPT REALTY, LLC

  2812 Bright Bird Ln, Winter Park, FL 32792
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  Est $465,553 Not Listed For Sale

  2260 Shadowland Loop, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2021

  2260 Shadowland Loop, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $204/SF
  • 2 Days On Market

  • Last Sold Price $470,000
  • Jul 17, 2024

  Last Listing Agent Jennifer Grimes ERA GRIZZARD REAL ESTATE
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  $179,000 Pending

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

  3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to this beautifully maintained 2-bedroom, 2-bathroom first-floor corner-unit condo in Winter Park, offering comfort, convenience, and peace of mind, with major updates completed in 2026. These upgrades were specifically implemented to enhance the property's aesthetic appeal and energy efficiency.The exterior updates include replacing all windows

  REZA Shirzad ANNE ROGERS REALTY GROUP INC

  3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
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  $2,150 Per Month

  • 3 Beds
  • 2 Baths
  • 1,113 Sq Ft
  • House for Rent

  1931 Carrigan Ave, Winter Park, FL 32792

  An excellent place to call home. This newly renovated 3 bedroom 2 bath house offers a lot of entertainment options; it is sitting on an oversize lot which features ample backyard space which is completely fenced. This home has brand new AC, Plumbing and Electric and offers washer/dryer hookups. Close to A+ schools and is approximately 7 minutes from Park Ave shopping and dining. This will not

  Amanda Beckman RED DOOR INVESTMENT GRP LLC

  1931 Carrigan Ave, Winter Park, FL 32792
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  $760,000 Sold Jul 17, 2025

  2159 Marsh Sedge Ln, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 2019

  Last Sold Summary

  • 4% Below List Price
  • $347/SF
  • 42 Days On Market

  Current Estimated Value $767,563

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

  2159 Marsh Sedge Ln, Winter Park, FL 32792
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  Not Listed For Sale

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

  0 Grand Rd Unit MFRO6213919, Winter Park, FL 32792

  Last Sold Summary

  • 55 Days On Market

  • Last Sold Price $635,000
  • Oct 03, 2024

  Last Listing Agent Marcella Mineo MARGAUX REALTY INC
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  $999,000

  • Land
  • 11,325 Sq Ft
  • $3,842,308 per Acre

  1836 Grinnell Terrace, Winter Park, FL 32789

  Opportunity to build your dream home in gorgeous Winter Park. This large lot includes a 3 bedroom 2 bath updated home. With a lot comprising 140 x 78 (11,305 square feet) there is plenty of room for a pool. Live in the house while you make your future plans!

  Cindy Kuykendall FANNIE HILLMAN & ASSOCIATES

  1836 Grinnell Terrace, Winter Park, FL 32789
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  $2,400 Per Month

  • 3 Beds
  • 3 Baths
  • 1,471 Sq Ft
  • Townhouse for Rent

  7542 Cranes Creek Ct, Winter Park, FL 32792

  The first month’s rent is 50% off with an approved lease. This beautifully upgraded end‑unit townhome in the Cranes Creek community offers 1,471 sq ft of thoughtfully laid‑out living space with 3 bedrooms and 3 baths across two stories. Built in 2006, the home features a one‑car attached garage, vaulted ceilings, tile and carpet flooring, ceiling fans,

  7542 Cranes Creek Ct, Winter Park, FL 32792
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  $450,000 Sold Jul 22, 2025

  1624 Little Wren Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft
  • Built 2019

  Last Sold Summary

  • 5% Below List Price
  • $195/SF
  • 23 Days On Market

  Current Estimated Value $468,312

  Last Listing Agent Steven Kwong CHARLES RUTENBERG REALTY ORLANDO

  1624 Little Wren Ln, Winter Park, FL 32792
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  Est $680,084 Not Listed For Sale

  1360 Blue Stem Ln, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 2021

  1360 Blue Stem Ln, Winter Park, FL 32792

  Last Sold Summary

  • $281/SF
  • 8 Days On Market

  • Last Sold Price $680,000
  • Jul 26, 2024

  Last Listing Agent Harif Hazera LLC PREMIER SOTHEBY'S INTL. REALTY

Showing Results 361 - 400, Page 10 of 18