Winter Park, FL Homes

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  $6,495,000 New Construction

  • 5 Beds
  • 6.5 Baths
  • 5,939 Sq Ft

  550 Palmer Ave, Winter Park, FL 32789

  Exquisite new construction with 5 Bedrooms 6.5 Baths and a 3 car garage, in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins

  John McDade FANNIE HILLMAN & ASSOCIATES

  550 Palmer Ave, Winter Park, FL 32789
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  $7,900 Per Month

  • 4 Beds
  • 3 Baths
  • 2,476 Sq Ft
  • House for Rent

  300 Killarney Dr, Winter Park, FL 32789

  Exceptional Lakefront Living in the Heart of Winter ParkWelcome to 300 Killarney Drive, a stunning 2,476 sq ft lakefront residence offering the perfect blend of sophisticated living and prime location. This exquisite 4-bedroom, 3-bath home presents a rare opportunity to enjoy Winter Park's coveted lifestyle.Property Highlights:Situated on an oversized lot with coveted Lake Killarney

  Kelly Price KELLY PRICE & COMPANY LLC

  300 Killarney Dr, Winter Park, FL 32789
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  $180,000 Sold Jan 06, 2026

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792

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

  Last Sold Summary

  • 3% Below List Price
  • $177/SF
  • 8 Days On Market

  Current Estimated Value $181,621

  Last Listing Agent Chris Bessette KELLER WILLIAMS CLASSIC

  2941 Antique Oaks Cir Unit 79, Winter Park, FL 32792
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  Est $217,515 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,165 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 1402, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $193/SF
  • 134 Days On Market

  • Last Sold Price $225,000
  • Mar 26, 2025

  Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC
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  /17

  $239,900

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

  7794 Country Place Unit 2, Winter Park, FL 32792

  Winter Park Clean, UPDATED and in Move In Condition - The newest condo's year built are located on the last street in the complex where this unit is located which features more contemporary open floor plans and high ceilings. Enjoy the One story living. No apartment living with noisy neighbors. Another BONUS is *** NO condo neighbors across the street from you - private!!** This unit is second to

  Tom Bercini CHARLES RUTENBERG REALTY ORLANDO

  7794 Country Place Unit 2, Winter Park, FL 32792
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  /11

  $2,050 Per Month

  • 3 Beds
  • 2 Baths
  • 1,317 Sq Ft
  • Winter Park 3 Bedroom 2 Bath Renovated!

  5171 N Orange Ave, Winter Park, FL 32792

  You don't want to miss out on this Winter Park Beauty! This lovely, RENOVATED, 3/2 block home, is situated on a large, fenced in lot and has been recently renovated ! The house has a nice open floor plan, with a great room and family room. The great room even has a wood burning fireplace. Renovations include...laminate wood floors throughout, interior paint, almost new kitchen appliances,

  5171 N Orange Ave, Winter Park, FL 32792
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  $1,950,000 Sold Sep 16, 2025

  141 Oakwood Way, Winter Park, FL 32789

  • 5 Beds
  • 4 Baths
  • 3,909 Sq Ft
  • Built 2015

  Last Sold Summary

  • 14% Below List Price
  • $499/SF
  • 170 Days On Market

  Current Estimated Value $1,959,270

  Last Listing Agent Nicole Rader MAINFRAME REAL ESTATE

  141 Oakwood Way, Winter Park, FL 32789
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  Est $205,950 Not Listed For Sale

  200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

  • 2 Beds
  • 1.5 Baths
  • 1,219 Sq Ft
  • Built 1970

  200 Saint Andrews Blvd Unit 3102, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $163/SF
  • 80 Days On Market

  • Last Sold Price $198,500
  • Jan 30, 2025

  Last Listing Agent John Muccigrosso RE/MAX
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  $349,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,140 Sq Ft

  989 Eastbrook Blvd, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. You’ve just found a Gem! Immaculate, move-in ready, and so conveniently located, you’ll love this turn-key home. Just painted inside and out, featuring brand new contemporary flooring, a 2025 AC, a newer tankless hot water heater, a brand new kitchen cooktop, all new light fixtures, switches, ceiling fans, and

  Jane Pedigree COLDWELL BANKER REALTY

  989 Eastbrook Blvd, Winter Park, FL 32792
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  $2,950 Per Month

  • 3 Beds
  • 2 Baths
  • 1,747 Sq Ft
  • House for Rent

  1807 N Park Ave, Winter Park, FL 32789

  Welcome to 1807 N Park Ave, a beautifully maintained 3-bedroom, 3-bathroom home offering 1,747 sq. ft. of bright, open living space in the heart of desirable Winter Park. This charming home features a spacious layout with a warm and inviting living area, a functional kitchen with plenty of storage, and comfortable bedrooms — each with its own bath, offering added privacy and convenience. Step

  Jason Hamilton THE REALTY MEDICS

  1807 N Park Ave, Winter Park, FL 32789
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  $170,000 Sold Jun 09, 2025

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Below List Price
  • $165/SF
  • 53 Days On Market

  Current Estimated Value $172,227

  Last Listing Agent Ali Khaku, MBA DALTON WADE INC

  3208 Oak Lawn Place Unit 218, Winter Park, FL 32792
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  Est $1,344,614 Not Listed For Sale

  1830 Pineview Cir, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,843 Sq Ft
  • Built 2024

  1830 Pineview Cir, Winter Park, FL 32792

  Last Sold Summary

  • 10% Below List Price
  • $527/SF
  • 57 Days On Market

  • Last Sold Price $1,499,000
  • Dec 14, 2024

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK
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  $379,900

  • 3 Beds
  • 2 Baths
  • 1,529 Sq Ft

  3245 Coleus Ct, Winter Park, FL 32792

  This home sits at the end of a cul-de-sac with an attractive courtyard entry to the 2 car garage. The Kitchen has been updated with new cabinets and tile flooring and the baths all have tile flooring. The Primary Bedroom has Luxury Vinyl Flooring. The screened porch overlooks a spacious fenced backyard that includes a block building (summer cottage) with electric and plumbing that is currently

  Diane Gerry PA RE/MAX 200 REALTY

  3245 Coleus Ct, Winter Park, FL 32792
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  $1,050 Per Month

  • 1 Bed
  • 1 Bath
  • House for Rent

  525 S Lakemont Ave, Winter Park, FL 32792

  Room Rental Listing: Room 01 – Master Bedroom with Attached BathroomThis listing is for Room 01, the Master Bedroom with an attached bathroom, in a fully furnished 3-bedroom, 2-bathroom house.Location: SW Zone @ 525 S Lakemont Ave, Winter Park, FloridaProperty Features: Preliminary Information :Appliances Provided:Cooking range with

  525 S Lakemont Ave, Winter Park, FL 32792
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  $145,000 Sold Apr 23, 2026

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft
  • Built 1969

  Last Sold Summary

  • 28% Below List Price
  • $225/SF
  • 286 Days On Market

  Last Listing Agent Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
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  Est $200,626 Not Listed For Sale

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Built 1983

  3251 Forest Oaks Ct Unit 115, Winter Park, FL 32792

  Last Sold Summary

  • 12% Below List Price
  • $220/SF
  • 13 Days On Market

  • Last Sold Price $227,000
  • Nov 08, 2024

  Last Listing Agent Ron Encarnacion RDE REALTY LLC
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  $128,500 Pending

  • 2 Beds
  • 2 Baths
  • 1,072 Sq Ft

  1000 S Semoran Blvd Unit 512, Winter Park, FL 32792

  Priced to sell! This 2 bedroom 2 bathroom condo located in the highly sought after Winter Park area is the perfect opportunity for an investor or a first time buyer. This unit has new luxury vinyl plank flooring throughout, recently upgraded kitchen cabinets, huge living room area and very spacious bedrooms. Located on the 2nd floor, and within steps of the community pool and laundry facility.

  Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

  1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
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  $3,200 Per Month

  • 2 Beds
  • 1 Bath
  • 1,250 Sq Ft
  • House for Rent

  438 Lakeview Ave, Winter Park, FL 32789

  Bring your boat and discover this charming Winter Park gem, perfectly nestled on a quiet, desirable brick-lined street. This inviting 2-bedroom, 1-bath home features beautiful hardwood floors and a warm, welcoming feel throughout. Enjoy a lakefront yard feet from the house that offers peaceful water views and the perfect setting for outdoor living. Step outside to an amazing backyard complete

  Alex Scures COLONIALTOWN REALTY

  438 Lakeview Ave, Winter Park, FL 32789
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  $850,000 Sold Mar 31, 2026

  1929 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,160 Sq Ft
  • Built 2023

  Last Sold Summary

  • 10% Below List Price
  • $394/SF
  • 91 Days On Market

  Current Estimated Value $907,218

  Last Listing Agent Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792
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  Est $974,311 Not Listed For Sale

  1484 Via Sangro Place, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,063 Sq Ft
  • Built 2015

  1484 Via Sangro Place, Winter Park, FL 32792

  Last Sold Summary

  • $317/SF
  • 5 Days On Market

  • Last Sold Price $970,000
  • Mar 11, 2025

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  $1,925,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,618 Sq Ft

  906 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. This home is under construction proposed completion March 2027. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with

  Laura Earl CORCORAN PREMIER REALTY

  906 Enclave Place, Winter Park, FL 32792
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  $1,650 Per Month

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

  1000 S Semoran Blvd, Winter Park, FL 32792

  This newly update and freshly painted. First floor condo in Winter Park offers a perfect blend of comfort and style and outdoor access ..It features two spacious bedrooms and two bathrooms, providing ample space for relaxation and privacy. The open plan living room and updated kitchen create a welcoming atmosphere, ideal for both entertaining and everyday living.. A standout features of this home

  1000 S Semoran Blvd, Winter Park, FL 32792
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  $912,500 Sold Jan 14, 2026

  210 Laurel Park Ct, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,838 Sq Ft
  • Built 2006

  Last Sold Summary

  • 4% Below List Price
  • $322/SF
  • 25 Days On Market

  Current Estimated Value $908,796

  Last Listing Agent Alireza Partovi EXP REALTY LLC

  210 Laurel Park Ct, Winter Park, FL 32792
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  Est $837,530 Not Listed For Sale

  1776 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2022

  1776 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Below List Price
  • $376/SF

  • Last Sold Price $825,000

  Last Listing Agent Kris Kennedy COMPASS FLORIDA LLC
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  $1,925,000

  • 4 Beds
  • 4 Baths
  • 2,653 Sq Ft

  721 Pansy Ave, Winter Park, FL 32789

  Ideally on a quiet residential street just near Park Avenue, this custom-built transitional residence offers the best of Winter Park living, accessible, refined and thoughtfully designed from the ground up. Built in 2018 by Carlos Posada, the home delivers 2,653 square feet of living space across two floors, with an additional 365 square feet walk-up attic, four bedrooms and four full baths. From

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  721 Pansy Ave, Winter Park, FL 32789
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  /19

  $1,995 Per Month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • House for Rent

  1942 Conifer Ct, Winter Park, FL 32792

  Leasing nicely furnished 2 bedrooms, 1 bath, living room, dining room and kitchen in 3 bedroom / 2 bath home. Each bedroom has queen size bed and closet. The kitchen is fully equipped including dishes. The living room has a sofa and tv.The dining room has a table with 4 chairs. The porch has some chairs and a small table. Outside in the back yard is a talbe with 4 chairs - picnic in your own park

  Scott Banta BLACKFIN REALTY LLC

  1942 Conifer Ct, Winter Park, FL 32792
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  $324,000 Sold Jun 17, 2025

  1920 Magnolia Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft
  • Built 1986

  Last Sold Summary

  • $242/SF

  Current Estimated Value $340,869

  Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

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

  663 Trinidad Ct Unit S, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft
  • Built 1981

  663 Trinidad Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • $201/SF
  • 164 Days On Market

  • Last Sold Price $224,900
  • Feb 24, 2025

  Last Listing Agent Ivan Tobon OUTLET REALTY
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  $99,000

  • Studio
  • 1 Bath
  • 537 Sq Ft

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

  Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

  Lynda Cheros OAKSTRAND REALTY

  3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
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  $2,195 Per Month

  • 3 Beds
  • 2 Baths
  • 1,627 Sq Ft
  • House for Rent

  3238 Black Pine Ave, Winter Park, FL 32792

  3 bed, 2 bath 1,625 sqft, Single Family Home, double garage, all kitchen appliances NO PETS!! Deposit is the same as the rent amount. CARPET floors and tile. Located off Goldenrod Blvd. Schools Near Full Sail University, UCF and these public schools; Winter Park High School, Glenridge Middle School, and Aloma Elementary. Great neighborhood. Available in May. SHOWINGS BY APPOINTMENT ONLY contact

  3238 Black Pine Ave, Winter Park, FL 32792
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  $485,000 Sold Aug 18, 2025

  1921 Japonica Rd, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 1971

  Last Sold Summary

  • $223/SF
  • 11 Days On Market

  Current Estimated Value $495,539

  Last Listing Agent Jose Gabriel Rodriguez COLDWELL BANKER REALTY

  1921 Japonica Rd, Winter Park, FL 32792
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  Est $1,129,009 Not Listed For Sale

  2726 Lake Howell Ln, Winter Park, FL 32792

  • 3 Beds
  • Built 1960

  2726 Lake Howell Ln, Winter Park, FL 32792

  Last Sold Summary

  • 16% Below List Price
  • $870/SF
  • 49 Days On Market

  • Last Sold Price $1,350,000
  • Oct 29, 2024

  Last Listing Agent Julie Sidorevskaya JULIES REALTY, LLC
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  $400,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,574 Sq Ft

  1036 Manchester Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Welcome to this well-maintained three-bedroom, two-bathroom home offering 1,574 square feet of thoughtfully designed living space in the established and highly desirable Howell Estates neighborhood of Winter Park. From the moment you enter, an abundance of natural light, ceiling fans throughout, and a functional layout create an open and inviting

  Amy Turner KELLER WILLIAMS WINTER PARK

  1036 Manchester Cir, Winter Park, FL 32792
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  $1,975 Per Month

  • 2 Beds
  • 1 Bath
  • 1,029 Sq Ft
  • House for Rent

  1803 Pineview Cir, Winter Park, FL 32792

  This beautiful 2 bed / 1 bath 1,029 square foot home in Winter Park is totally refurbished and available for immediate occupancy. Newer kitchen cabinets. Newer bathroom. With a single car carport. This property features wood floors throughout, tile floors in the kitchen, dining room and bathroom, large open yard. Washer/dryer, shed & lawn care included! Application Fee: $50 each adult

  Kenneth Warren PREMIER MANAGEMENT GROUP INC

  1803 Pineview Cir, Winter Park, FL 32792
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  $335,000 Sold Oct 31, 2025

  3525 Baxter Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1970

  Last Sold Summary

  • 14% Above List Price
  • $215/SF
  • 5 Days On Market

  Current Estimated Value $326,527

  Last Listing Agent Ashley Fisak COLDWELL BANKER REALTY

  3525 Baxter Dr, Winter Park, FL 32792
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  Est $295,098 Not Listed For Sale

  5879 Marble Ct, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,041 Sq Ft
  • Built 1988

  5879 Marble Ct, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $298/SF
  • 6 Days On Market

  • Last Sold Price $310,000
  • Aug 30, 2024

  Last Listing Agent Deanna Armel ARMEL REAL ESTATE INC
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  $579,000

  • 4 Beds
  • 2 Baths
  • 1,821 Sq Ft

  2829 Aloma Ave, Winter Park, FL 32792

  Just Listed – 2829 Aloma Avenue, Winter Park This is the one you’ve been waiting for. A completely remodeled home with a private pool in one of the most desirable areas of Central Florida—all for under $600,000. Enjoy the perfect blend of modern upgrades and unbeatable location, just minutes from top-rated restaurants, shopping, excellent schools, and everything that makes Winter Park so special.

  Roberto Silva LPT REALTY, LLC

  2829 Aloma Ave, Winter Park, FL 32792
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  $4,195 Per Month

  • 4 Beds
  • 3 Baths
  • 2,134 Sq Ft
  • WINTER PARK POOL HOME WITH WINTER PARK SCHOOLS! (Orange County Winter Park Schools)

  1625 Tioga Trail, Winter Park, FL 32789

  AVAILABLE FOR MOVE-IN EARLY JUNE 2026.A RARE FIND IN WINTER PARK!! 4 BEDROOMS, 3 BATHROOMS, POOL, AND FENCED BACKYARD.Very seldom do such nice rental homes come available in the school district of Dommerich, Maitland Middle and Winter Park High! People love The Hills of Winter Park with this home located on a cul-de-sac street.This home features 4 Bedrooms and 3 Full

  1625 Tioga Trail, Winter Park, FL 32789
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  $1,100,000 Sold May 29, 2025

  708 Balmoral Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,786 Sq Ft
  • Built 1960

  Last Sold Summary

  • 4% Below List Price
  • $395/SF
  • 130 Days On Market

  Current Estimated Value $1,126,539

  Last Listing Agent Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  708 Balmoral Rd, Winter Park, FL 32789
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  Est $732,289 Not Listed For Sale

  1166 Wildmeadow Run, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft
  • Built 2021

  1166 Wildmeadow Run, Winter Park, FL 32792

  Last Sold Summary

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

  • Last Sold Price $745,000
  • Nov 21, 2024

  Last Listing Agent Liz Jones ORANGE SLICE PROPERTIES

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