Winter Park, FL Homes

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  /10

  $249,900 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,232 Sq Ft

  1823 Maywood Rd, Winter Park, FL 32792

  Under contract-accepting backup offers. Located in the heart of Winter Park, this property is a prime candidate for redevelopment. Sitting on a ~9,259 sq ft lot, this is an ideal opportunity for builders or investors looking to capitalize on land value in a highly desirable area.The existing structure is a 3 bed, 1.5 bath home, but the true value here is in the lot and location. The seller

  Abby Nelson RE/MAX 200 REALTY

  1823 Maywood Rd, Winter Park, FL 32792
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  /16

  $2,495 per month

  • 3 Beds
  • 2 Baths
  • 1,544 Sq Ft
  • House for Rent

  2316 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 $2639.90. That covers your base rent, $2495.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  2316 Dunbury Ct, Winter Park, FL 32792
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  /2

  $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 $416,529

  Last Listing Agent Virginia Silberstein ORLANDO EXPERT REALTY LLC

  1189 Lazy Hollow Place, Winter Park, FL 32792
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  /2

  Est $314,183 Not Listed For Sale

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft
  • Built 1960

  311 E Morse Blvd Unit 7-15, Winter Park, FL 32789

  Last Sold Summary

  • 5% Below List Price
  • $684/SF
  • 3 Days On Market

  Last Sold Price $329,900

  Last Listing Agent Susan Logan LOGAN LAND & HOMES, INC.
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  /8

  $849,000

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

  1780 Bryan Ave, Winter Park, FL 32789

  Discover a truly unique offering in the heart of Winter Park! This property, located at 1780 Bryan Avenue, is being offered along with theadjoining lots at 1760 and 1770 Bryan Avenue. While available together as a rare collection of three consecutive parcels, each lot is also being sold separately at individual prices, giving buyers the flexibility to purchase one, two, or all three.

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1780 Bryan Ave, Winter Park, FL 32789
• 

  

  /25

  $5,490 per month

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft
  • Condo for Rent

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789

  Welcome to this charming condominium in Winter Park! This home features a spacious living area with ample natural light, a modern kitchen with sleek appliances, and large bedrooms. Enjoy the convenience of nearby shopping, dining, and entertainment. The community provides well-maintained amenities for residents to enjoy. With its prime location, this condo provides easy access to all that the

  Steven Koleno BEYCOME OF FLORIDA LLC

  782 S Pennsylvania Ave Unit 1, Winter Park, FL 32789
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  /2

  $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 $397,449

  Last Listing Agent Ivanhoe Alvarez LOKATION

  3425 Ferndell Dr, Winter Park, FL 32792
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  /2

  Est $301,052 Not Listed For Sale

  3251 Crown Jewel Ct, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft
  • Built 2019

  3251 Crown Jewel Ct, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $247/SF
  • 6 Days On Market

  Last Sold Price $348,000

  Last Listing Agent Erin Fang FLORIDA REALTY INVESTMENTS
• 

  

  /18

  $279,990

  • 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
• 

  

  /15

  $2,710 per month

  • 4 Beds
  • 3 Baths
  • 1,856 Sq Ft
  • House for Rent

  2029 Taylor Ave, Winter Park, FL 32792

  Please note that the advertised price may exclude additional fees. These include a $55 application fee per applicant; a one-time $75 admin fee; a $11 monthly utility management fee; other mandatory fees, if applicable, for pool maintenance, pet fees/rent, smart home, internet service, and propane refilling; and optional fees for services like self-guided tours with third-party provider Rently

  2029 Taylor Ave, Winter Park, FL 32792
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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 $239,768

  Last Listing Agent Deborah Morris KELLER WILLIAMS ADVANTAGE REALTY

  613 Orange Tree Ct Unit 507, Maitland, FL 32751
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  /2

  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

  Last Listing Agent Natalie Rudnitsky FLORIDA CAPITAL REALTY
• 

  

  /25

  $179,000

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 122, Winter Park, FL 32789

  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 countertops, soft-close cabinetry, and

  Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

  2500 Lee Rd Unit 122, Winter Park, FL 32789
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  /23

  $1,425 per month

  • 2 Beds
  • 1 Bath
  • 920 Sq Ft
  • Condo for Rent

  1380 Indiana Ave Unit 3, Winter Park, FL 32789

  Winter Park at your door step! This is a second floor 2 bedroom unit, in secured building. Large open backyard with rear balcony and patio space and plenty of parking. Unit has full kitchen, and washer/dryer in unit! Two full bedrooms both with walk-in closets and a full bath. Living room is large open/bright. Only a few blocks walk to Orlando Ave with all its shopping, Publix and restaurants.

  Scott Butts KIMBRIDGE REALTY, LLC

  1380 Indiana Ave Unit 3, Winter Park, FL 32789
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  /2

  $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 $259,227

  Last Listing Agent Adriana Gonzalez PERFECT INVESTMENT REALTY

  Unlisted Address
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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

  Last Listing Agent Georgina O'Bryan SIGNATURE BROKERS REALTY LLC
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  /50

  $635,000

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

  2708 Lion Heart Rd, Winter Park, FL 32792

  Welcome to 2407 Lion Heart, Winter Park — where timeless elegance meets modern comfort. Nestled in one of Winter Park’s most desirable communities, this fully renovated 3-bedroom, 2-bath residence offers the perfect blend of sophistication, functionality, and peaceful living. Step inside and experience 1,785 square feet of thoughtfully designed open-concept living space, highlighted by wide-plank

  Navid Rokh EQUITYPRO LLC

  2708 Lion Heart Rd, Winter Park, FL 32792
• 

  

  /20

  $3,995 per month

  • 4 Beds
  • 3.5 Baths
  • 2,604 Sq Ft
  • Townhouse for Rent

  438 W Swoope Ave, Winter Park, FL 32789

  SPECIAL!! $500 OFF THE 1ST MO RENT IF YOU MOVE IN BEFORE 3/31!!PRIME LOCATION! JUST STEPS FROM PARK AVENUE, WALKING DISTANCE TO EVERYTHING!This beautiful TOWNHOME is located in the exclusive 400 West community, just moments from Park Avenue. It offers a PERFECT COMBINATION OF SUPERIOR CRAFTSMANSHIP, ELEGANT INTERIORS, and GREAT WALKABILITY. You can enter via the PRIVATE GARAGE or

  438 W Swoope Ave, Winter Park, FL 32789
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  $1,000,000 Sold Apr 04, 2025

  1001 Tuscany Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 2,458 Sq Ft
  • Built 1978

  Last Sold Summary

  • 22% Below List Price
  • $407/SF
  • 141 Days On Market

  Current Estimated Value $1,080,922

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1001 Tuscany Place, Winter Park, FL 32789
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  /2

  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

  Last Listing Agent Denise McKinley RE/MAX
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  /28

  $145,000 Pending

  • 1 Bed
  • 1 Bath
  • 645 Sq Ft

  2500 Lee Rd Unit 243, Winter Park, FL 32789

  Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

  Sue Gilman KELLER WILLIAMS WINTER PARK

  2500 Lee Rd Unit 243, Winter Park, FL 32789
• 

  

  /19

  $1,450 per month

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

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792

  Beautiful 2-bedroom, 2-bath condo available for rent in the highly desirable Winter Park area. This inviting home is thoughtfully designed for comfortable family living and features no carpet, with durable laminate flooring throughout perfect for easy cleaning and everyday use. The condo offers a spacious and functional layout, including a bright living area ideal for family time and

  Praveen Setty RIGHTHOUSE REALTY LLC

  3651 N Goldenrod Rd Unit 110, Winter Park, FL 32792
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  /2

  $400,000 Sold May 07, 2025

  2292 Hawick Ln, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,322 Sq Ft
  • Built 1958

  Last Sold Summary

  • $303/SF
  • 3 Days On Market

  Current Estimated Value $405,968

  Last Listing Agent Jason Alderman KELLER WILLIAMS ADVANTAGE REALTY

  2292 Hawick Ln, Winter Park, FL 32792
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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

  Last Listing Agent Liza Figueroa EXP REALTY LLC
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  /32

  $915,000 Pending

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

  1929 S Lakemont Ave, Winter Park, FL 32792

  This modern Winter Park townhome sits in a quiet pocket between Lake Spier and Lake Compton, offering a rare mix of style, comfort, and convenience. This home feels tucked away while still keeping you close to everything you love about Winter and Baldwin Park. Inside, the layout is open and easy to live in. The kitchen features stone countertops, stainless steel appliances, and a large island

  Brandon Geers COMPASS FLORIDA LLC

  1929 S Lakemont Ave, Winter Park, FL 32792
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  /45

  $1,940 per month

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Condo for Rent

  1307 Formosa Ave Unit SI ID1250011P, Winter Park, FL 32789

  The advertised rate of $1,941/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 4, 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

  1307 Formosa Ave Unit SI ID1250011P, Winter Park, FL 32789
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  /2

  $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 $995,846

  Last Listing Agent Frances Speights KELLER WILLIAMS ADVANTAGE III

  1265 Park Pointe Ln, Winter Park, FL 32789
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  /2

  Est $1,089,897 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

  • 18% Below List Price
  • $557/SF
  • 2 Days On Market

  Last Sold Price $1,325,000

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
• 

  

  /39

  $185,000

  • 2 Beds
  • 2 Baths
  • 840 Sq Ft

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

  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 with single-hung, double-pane, low-E

  REZA Shirzad ANNE ROGERS REALTY GROUP INC

  3651 N Goldenrod Rd Unit 101, Winter Park, FL 32792
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  /52

  $8,950 per month

  • 3 Beds
  • 3 Baths
  • 2,462 Sq Ft
  • Condo for Rent

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789

  Enjoy elevated lakeside living in this top-floor residence overlooking tranquil Lake Osceola in downtown Winter Park. Located on the top level of the Whispering Waters condominium community, this fully remodeled home features three spacious bedrooms (one currently used as a den), three full baths and an open layout designed to showcase expansive water views. The primary suite features an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  311 E Morse Blvd Unit 1-5, Winter Park, FL 32789
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  /2

  $1,975,000 Sold Mar 27, 2025

  140 Dana Way, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 3,441 Sq Ft
  • Built 2011

  Last Sold Summary

  • 6% Below List Price
  • $574/SF
  • 16 Days On Market

  Current Estimated Value $2,007,732

  Last Listing Agent Maria Blanchard OLDE TOWN BROKERS INC

  140 Dana Way, Winter Park, FL 32789
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  /2

  Est $455,208 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

  • 1% Below List Price
  • $235/SF
  • 40 Days On Market

  Last Sold Price $461,000

  Last Listing Agent Nohora Gomez COLDWELL BANKER REALTY
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  /36

  $424,000 Pending

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

  2834 Bright Bird Ln, Winter Park, FL 32792

  Under contract-accepting backup offers. Preferred Lender rate Incentives available. This beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and

  Irene Navarro LIFESTYLE INTERNATIONAL REALTY

  2834 Bright Bird Ln, Winter Park, FL 32792
• 

  

  /15

  $2,735 per month

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

  3021 Dikewood Ct, 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

  3021 Dikewood Ct, Winter Park, FL 32792
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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
• 

  /2

  Est $706,243 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

  • 1% Above List Price
  • $347/SF
  • 68 Days On Market

  Last Sold Price $699,000

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /3

  $1,950,000 New Construction

  • 4 Beds
  • 4 Baths
  • 2,810 Sq Ft

  2501 Lafayette Ave, Winter Park, FL 32789

  Under Construction. Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom pivot front door into the foyer leading to your main living area featuring sliding glass walls for indoor-outdoor living.

  Tab Bish LLC REAL BROKER, LLC

  2501 Lafayette Ave, Winter Park, FL 32789
• 

  

  /11

  $1,575 per month

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

  3651 N Goldenrod Rd Unit 205, Winter Park, FL 32792

  2 Bedroom/2 Bathroom 2nd Floor Unit at Lancelot. Location, Location, Location... with only a few minutes to downtown Orlando, UCF, Valencia, Full Sail, Rollins College, theme parks, beaches, airport, highways 417 & 408, entertainment, dining & shopping. This 2nd floor end unit boasts of an open floor plan with the kitchen being open to the living room/dining area and features a breakfast bar.

  Kelly Carr CFRP REALTY LLC

  3651 N Goldenrod Rd Unit 205, 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 $3,340,418

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  182 N Phelps Ave, Winter Park, FL 32789
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  /2

  Est $498,678 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

  • $216/SF
  • 14 Days On Market

  Last Sold Price $499,000

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

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