Winter Park, FL Homes

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  $695,000

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Welcome to your dream home! This exceptional 4-bedroom residence features a desirable split floor plan, offering both privacy and functionality. Nestled on a quiet corner lot in the serene Winter Park Pines community, this property is just a few steps away from the scenic Cady Way Trail, perfect for outdoor enthusiasts.This home is surrounded by recreational opportunities, including a refreshing

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  $1,850

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Condo for Rent

  1500 Gay Rd Unit 9D, Winter Park, FL 32789

  Two-bedroom, two-bath walk-up condo off Lake Killarney in Winter Park, Florida. Spacious rooms, custom upgrades, quiet, and well maintained. Located in the Chateaux du Lac community at 1500 GayRoad. Within walking distance of Winter Park Village, Traders Joe's, restaurants and more. Minutes from AdventHealth Orlando, Park Avenue, Rollins College, and I-4.Pet free unit. Ideally seeking

  1500 Gay Rd Unit 9D, Winter Park, FL 32789
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  $421,700 Sold May 29, 2025

  1189 Lazy Hollow Place, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,525 Sq Ft
  • Built 1984

  Last Sold Summary

  • $277/SF
  • 7 Days On Market

  Current Estimated Value $427,900

  Last Listing Agent Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
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  Not Listed For Sale

  2609 Holly Rd Unit 2611, Winter Park, FL 32792

  • 4 Beds
  • 4 Baths
  • 2,382 Sq Ft
  • Built 1972

  2609 Holly Rd Unit 2611, Winter Park, FL 32792

  Last Sold Summary

  • $201/SF
  • 7 Days On Market

  • Last Sold Price $479,900
  • Jan 10, 2025

  Last Listing Agent Natalie Rudnitsky FLORIDA CAPITAL REALTY
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  $2,800,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,553 Sq Ft

  541 W Canton Ave, Winter Park, FL 32789

  Timeless elegance meets boutique craftsmanship at 541 W Canton Ave., an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Near Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm and rich character with elevated modern living and a refined sense of calm. From its dormer windows and custom-carved wood

  Bianca Rey PREMIER SOTHEBY'S INTL. REALTY

  541 W Canton Ave, Winter Park, FL 32789
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  /40

  $3,895 Per Month

  • 4 Beds
  • 4.5 Baths
  • 2,553 Sq Ft
  • House for Rent

  1409 Lone Feather Trail, Winter Park, FL 32792

  Beautiful tile roof single-family house is available in Hawks Crest, the only newal gated community in Winter Park! No rear neighbors! Landscape/Lawn Care and Reclaimed Water Bill are paid by landlord. UV sanitizing lights installed in all bathrooms. Water filter system installed in kitchen sink. This 4 bed 3.5 bathrooms plus an office and second floor loft is ready to move-in . When you enter

  Yan Zuo EAST PEARL REALTY

  1409 Lone Feather Trail, Winter Park, FL 32792
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  $405,000 Sold Jan 09, 2026

  3425 Ferndell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,516 Sq Ft
  • Built 1966

  Last Sold Summary

  • 5% Below List Price
  • $267/SF
  • 164 Days On Market

  Current Estimated Value $391,495

  Last Listing Agent Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
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  Not Listed For Sale

  104 Moyses Rd, Winter Park, FL 32792

  • 4 Beds
  • 4 Baths
  • 1,872 Sq Ft
  • Built 1985

  104 Moyses Rd, Winter Park, FL 32792

  Last Sold Summary

  • $249/SF
  • 43 Days On Market

  • Last Sold Price $467,000
  • Feb 10, 2025

  Last Listing Agent Georgina O'Bryan SIGNATURE BROKERS REALTY LLC
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  /26

  $599,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,157 Sq Ft

  7917 Pleasant Pine Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Come see this BEAUTIFULLY MAINTAINED, EMACULATE WINTER PARK HOME ON A QUIET STREET IN A SECLUDED GATED ENCLAVE OF HOMES! This is a one owner home and has been maintained in pristine, like new condition. Located in a small gated community moments from Trinity Preparatory School, Park Avenue Shoppes and Rollins College. When entering this home you are greeted

  Lori Gilmore LORI GILMORE REAL ESTATE LLC

  7917 Pleasant Pine Cir, Winter Park, FL 32792
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  $3,350

  Total Monthly Price

  • 2 Beds
  • 2 Baths
  • 1,312 Sq Ft
  • Townhouse for Rent

  1886 Demetree Dr, Winter Park, FL 32789

  Beautifully Remodeled Ground-Floor Townhome — Available Now in Winter Park Welcome home to this stylish, move-in-ready townhome located in the heart of Winter Park. Enjoy the perfect balance of convenience and comfort—just a short walk to Winter Park Dog Park and Baldwin Park, and minutes from Rollins College, Park Avenue, downtown Orlando, and major hospitals. This thoughtfully

  1886 Demetree Dr, Winter Park, FL 32789
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  /2

  $235,000 Sold Jan 29, 2026

  613 Orange Tree Ct Unit 507, Maitland, FL 32751

  • 3 Beds
  • 2 Baths
  • 1,256 Sq Ft
  • Built 1974

  Last Sold Summary

  • 3% Below List Price
  • $187/SF
  • 10 Days On Market

  Current Estimated Value $234,240

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  Est $454,879 Not Listed For Sale

  1323 Merrydale Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft
  • Built 2021

  1323 Merrydale Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $229/SF
  • 98 Days On Market

  • Last Sold Price $449,000
  • Apr 01, 2025

  Last Listing Agent Melissa Johnson EXP REALTY LLC
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  $354,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft

  5330 Tangerine Ave, Winter Park, FL 32792

  You'll love this single-owner gem in Winter Park! Step inside to a traditional foyer, which welcomes you into a formal living room with excellent natural light and great flow into the dining room. Adjacent, you'll find the centrally located, spacious kitchen which overlooks your family room! A true split plan, the primary bedroom and oversized suite are on one side of the home and the two

  Courtney Pelfrey MILLER GRANT AND COMPANY

  5330 Tangerine Ave, Winter Park, FL 32792
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  /16

  $1,400 Per Month

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

  1695 Lee Rd Unit C110, Winter Park, FL 32789

  Spacious first floor unit in Waterfall Cove 1 bedroom, charming residential unit , This inviting space offers a comfortable layout with plenty of natural light. Conveniently located near shops, restaurants and parks. It is perfect for enjoying the Winter park lifestyle.

  Yigit Orer EMPIRE NETWORK REALTY

  1695 Lee Rd Unit C110, Winter Park, FL 32789
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  $298,000 Sold Aug 15, 2025

  2206 Bonanza Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,776 Sq Ft
  • Built 1971

  Last Sold Summary

  • 15% Below List Price
  • $168/SF
  • 9 Days On Market

  Current Estimated Value $424,901

  Last Listing Agent Hannah Evans FLORIDA REALTY INVESTMENTS

  2206 Bonanza Ave, Winter Park, FL 32792
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  Not Listed For Sale

  667 Montego Bay Ct Unit S, Winter Park, FL 32792

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

  667 Montego Bay Ct Unit S, Winter Park, FL 32792

  Last Sold Summary

  • $192/SF
  • 44 Days On Market

  • Last Sold Price $215,000
  • Jan 24, 2025

  Last Listing Agent Denise McKinley RE/MAX
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  $4,595,000 Pending

  • 4 Beds
  • 5 Baths
  • 3,181 Sq Ft

  1336 College Point, Winter Park, FL 32789

  Under contract-accepting backup offers. Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1336 College Point, Winter Park, FL 32789
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  $1,750 Per Month

  • 2 Beds
  • 1 Bath
  • 854 Sq Ft
  • House for Rent

  2304 Inagua Way, Winter Park, FL 32792

  Welcome to this charming 2 bedroom, 1 bathroom corner unit in Winter Park, FL. This single-story home features ceramic tile flooring throughout, perfect for easy maintenance. The freshly painted interior complements the renovated kitchen and bathroom, giving the space a modern and updated feel. Enjoy the privacy of the fenced backyard, ideal for outdoor entertaining or relaxing. Located in the

  2304 Inagua Way, Winter Park, FL 32792
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  $279,000 Sold Aug 11, 2025

  Unlisted Address

  • 2 Beds
  • 2.5 Baths
  • 1,186 Sq Ft
  • Built 1981

  Last Sold Summary

  • $235/SF
  • 4 Days On Market

  Current Estimated Value $272,936

  Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

  Unlisted Address
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  Not Listed For Sale

  3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,088 Sq Ft
  • Built 1974

  3015 Aaron Burr Ave Unit 7, Winter Park, FL 32792

  Last Sold Summary

  • $118/SF
  • 11 Days On Market

  • Last Sold Price $128,000
  • Dec 26, 2024

  Last Listing Agent Liza Figueroa EXP REALTY LLC
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  $650,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,917 Sq Ft

  352 Cambridge Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. This charming, income-producing property is a standout investment opportunity offering the rare ability to either live in or collect rent from separate units. The main house features a bright, open floorplan with three bedrooms and one beautifully remodeled bathroom, highlighted by warm wood flooring, a welcoming family room, formal dining room, and a

  Karen Jacobs COLDWELL BANKER REALTY

  352 Cambridge Blvd, Winter Park, FL 32789
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  /21

  $2,900 Per Month

  • 3 Beds
  • 1 Bath
  • 1,056 Sq Ft
  • House for Rent

  540 W Comstock Ave, Winter Park, FL 32789

  Newly Renovated | Prime Winter Park Location | Move-In Ready Opportunity Positioned in one of Central Florida’s most desirable and high-demand areas, this newly renovated residence at 540 W Comstock Ave offers a rare opportunity for tenants seeking both location and lifestyle in the heart of Winter Park. Thoughtfully updated with modern finishes, the home features a clean, refreshed interior

  Fredrick Jacobs KELLER WILLIAMS GAINESVILLE REALTY PARTNERS

  540 W Comstock Ave, Winter Park, FL 32789
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  $1,002,000 Sold May 31, 2025

  1265 Park Pointe Ln, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1989

  Last Sold Summary

  • 3% Above List Price
  • $437/SF
  • 4 Days On Market

  Current Estimated Value $1,006,067

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  Est $1,117,616 Not Listed For Sale

  1782 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,377 Sq Ft
  • Built 2023

  1782 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 16% Below List Price
  • $557/SF
  • 2 Days On Market

  • Last Sold Price $1,325,000
  • Nov 26, 2024

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  $562,000 Pending

  • 4 Beds
  • 3 Baths
  • 1,778 Sq Ft

  5233 Lake Howell Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. NO HOA. Dual Master Suites. One main, and one mother-in-law or guest suite. All single story, no stairs. NEW POOL DECK. NEW POOL PUMP. POOL RESURFACED.NEW ROOF (installation in progress). Totally renovated. NEW HOT WATER HEATER. NEW FLOORS. POOL RESURFACED. NEW POOL DECK. NEW POOL PUMP. NEW ALL TURF BACK LAWN (NO Mowing). NEW PUTTING GREEN (for your

  Miranda Cady CADENCE LIFESTYLE REAL ESTATE

  5233 Lake Howell Rd, Winter Park, FL 32792
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  $1,775 Per Month

  • 2 Beds
  • 2 Baths
  • 964 Sq Ft
  • Condo for Rent

  3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792

  3254 Howell Branch Rd Unit Howell Branch Rd - 3254, Winter Park, FL 32792
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  $649,000 Sold Oct 17, 2025

  2304 Depauw Ave, Orlando, FL 32804

  • 3 Beds
  • 2.5 Baths
  • 1,668 Sq Ft
  • Built 2025

  Move in Ready Sold Summary

  • $389/SF
  • 199 Days On Market

  Current Estimated Value $657,000

  David Weekley Homes Central Living - Downtown

  2304 Depauw Ave, Orlando, FL 32804
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  Est $450,900 Not Listed For Sale

  1596 Little Wren Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,964 Sq Ft
  • Built 2020

  1596 Little Wren Ln, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $235/SF
  • 40 Days On Market

  • Last Sold Price $461,000
  • Dec 20, 2024

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  $325,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,575 Sq Ft

  7529 Village Green Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. ***Multiple Offers Received. Please submit your highest and best offer by Monday, April 13th at 12 noon.***Buyer incentives you don't want to miss! This home qualifies for a 1% lender credit with our preferred lender. Location meets affordability with this rare opportunity in Winter Park with no HOA! With some TLC, this 3 bedroom, 2 bath home offers endless

  Kim Goldin KELLER WILLIAMS ADVANTAGE REALTY

  7529 Village Green Dr, Winter Park, FL 32792
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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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  $230,000 Sold Aug 29, 2025

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  Last Sold Summary

  • 6% Below List Price
  • $224/SF
  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC

  1500 Gay Rd Unit 7A, Winter Park, FL 32789
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  Est $713,262 Not Listed For Sale

  1804 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,016 Sq Ft
  • Built 2018

  1804 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $347/SF
  • 68 Days On Market

  • Last Sold Price $699,000
  • Feb 07, 2025

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  $750,000

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  676 Dunblane Dr, Winter Park, FL 32792

  This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as

  Emma Kaplan BALDWIN PARK REALTY LLC

  676 Dunblane Dr, Winter Park, FL 32792
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  $2,500 Per Month

  • 3 Beds
  • 2 Baths
  • 1,676 Sq Ft
  • Beautiful Home in Winter Park, Florida!

  7508 Glenmoor Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully refreshed 3-bedroom, 2-bath home nestled in a highly desirable Winter Park location — offering comfort, style, and convenience with no HOA restrictions. With 1,676 square feet of thoughtfully designed living space, this home is the perfect blend of modern updates and timeless character. Step inside to discover brand-new

  7508 Glenmoor Ln, Winter Park, FL 32792
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  $3,450,000 Sold Jul 25, 2025

  182 N Phelps Ave, Winter Park, FL 32789

  • 4 Beds
  • 5 Baths
  • 4,812 Sq Ft
  • Built 2025

  Last Sold Summary

  • 4% Below List Price
  • $717/SF
  • 61 Days On Market

  Current Estimated Value $3,181,636

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  Est $492,416 Not Listed For Sale

  1303 Merrydale Way, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Built 2021

  1303 Merrydale Way, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $216/SF
  • 14 Days On Market

  • Last Sold Price $499,000
  • Dec 10, 2024

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  $589,900

  • 3 Beds
  • 2 Baths
  • 1,269 Sq Ft

  1354 Indiana Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Fabulous location in Winter Park! Completely remodeled from top to bottom this stunning home blends modern design with everyday comfort in a highly desirable Winter Park location. Thoughtfully updated with stylish and contemporary finishes throughout this home offers a bright and open feel that’s perfect for today’s lifestyle.The beautifully

  Ellen Bessette CHARLES RUTENBERG REALTY ORLANDO

  1354 Indiana Ave, Winter Park, FL 32789
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  /25

  $2,400 Per Month

  • 3 Beds
  • 2 Baths
  • 1,467 Sq Ft
  • Townhouse for Rent

  2379 Flamingo Way, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom townhome in the highly desirable area of Winter Park—perfect for renters seeking comfort, convenience, and a vibrant community lifestyle. Step inside to an open-concept layout designed for modern living, featuring stylish tile flooring and a spacious kitchen with granite countertops that flows effortlessly into the living and dining

  Samuel Kingsford STOCKWORTH REALTY GROUP

  2379 Flamingo Way, Winter Park, FL 32792
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  $905,000 Sold Mar 11, 2026

  5325 Cypress Reserve Place, Winter Park, FL 32792

  • 5 Beds
  • 3.5 Baths
  • 3,598 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Below List Price
  • $252/SF
  • 322 Days On Market

  Current Estimated Value $885,231

  Last Listing Agent Dori Estrada AXEN REALTY, LLC

  5325 Cypress Reserve Place, Winter Park, FL 32792
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  Est $395,320 Not Listed For Sale

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft
  • Built 1986

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $251/SF
  • 171 Days On Market

  • Last Sold Price $385,000
  • May 02, 2025

  Last Listing Agent Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

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