Winter Park, FL Homes

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  $1,950,000

  • 3 Beds
  • 2 Baths
  • 1,807 Sq Ft

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789

  Designer-Curated Coastal Renovation with Exceptional Lakefront Vistas! This sophisticated reimagining was taken down to original framework and meticulously rebuilt with elevated design and superior finishes throughout. The result is an expansive openness illuminated with natural light and accented by European oak wide-plank flooring, Level 5 smooth-finish walls and ceilings, architectural

  Mary Colton FANNIE HILLMAN & ASSOCIATES

  106 S Interlachen Ave Unit 518, Winter Park, FL 32789
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  /17

  $1,595 Per Month

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

  1695 Lee Rd Unit C206, 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 (added privacy) -

  Yein Ross ROSS RENTALS LLC

  1695 Lee Rd Unit C206, Winter Park, FL 32789
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  $3,845,000 Sold May 16, 2025

  2020 Venetian Way, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $918/SF
  • 4 Days On Market

  Current Estimated Value $3,891,840

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

  2020 Venetian Way, Winter Park, FL 32789
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  /55

  Est $1,071,527 Not Listed For Sale

  1772 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft
  • Built 2023

  1772 Mondrian Cir, Winter Park, FL 32789

  Last Sold Summary

  • 14% Below List Price
  • $570/SF
  • 83 Days On Market

  • Last Sold Price $1,250,000
  • Feb 16, 2024

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY
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  /53

  $1,299,000

  • 3 Beds
  • 2 Baths
  • 1,734 Sq Ft

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789

  On the first floor within The Cloisters, this three-bedroom, two-bath residence offers 1,734 square feet of renovated living space in one of Winter Park’s accessible lakefront communities. An oversized tiled patio, partially covered and ideal for outdoor dining or morning coffee, extends the living space and enhances everyday functionality. Renovated in 2021 by Charles Clayton Construction, an

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  100 S Interlachen Ave Unit 101, Winter Park, FL 32789
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  /39

  $12,000 Per Month

  • 4 Beds
  • 3.5 Baths
  • 3,064 Sq Ft
  • House for Rent

  1041 Tuscany Place, Winter Park, FL 32789

  Nestled along a quiet brick-lined street in Winter Park’s coveted Via’s neighborhood, 1041 Tuscany Place offers a rare blend of elegance, comfort, and breathtaking natural beauty. From nearly every room, this exceptional residence captures tranquil views of the private backyard and picturesque Lake Temple beyond. Inside, a thoughtfully designed open floor plan is enhanced by soaring vaulted

  Brad Barnett COMPASS FLORIDA LLC

  1041 Tuscany Place, Winter Park, FL 32789
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  /2

  $130,000 Sold Nov 25, 2025

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft
  • Built 1970

  Last Sold Summary

  • 13% Below List Price
  • $179/SF
  • 35 Days On Market

  Current Estimated Value $137,505

  Last Listing Agent Mary Marwick PREMIUM PROPERTIES R.E SERVICE

  200 Saint Andrews Blvd Unit 101, Winter Park, FL 32792
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  /19

  Est $235,686 Not Listed For Sale

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

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

  200 Saint Andrews Blvd Unit 1807, Winter Park, FL 32792

  Last Sold Summary

  • 16% Below List Price
  • $230/SF
  • 6 Days On Market

  • Last Sold Price $280,000
  • Mar 25, 2024

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /62

  $4,995,000 Pending

  • 5 Beds
  • 5.5 Baths
  • 4,738 Sq Ft

  1302 Raintree Place, Winter Park, FL 32789

  Under contract-accepting backup offers. *Under Contract - Accepting Backup Offers* An expression of modern luxury by SMRS Design and Cole Homes, The Maybourne masterfully blends Neoclassical elegance with Art Deco sophistication—all just steps from Winter Park’s iconic Park Avenue. A curved, manicured driveway leads to a grand entrance featuring bespoke double doors with electromagnetic privacy

  Rikhil Amin FANNIE HILLMAN & ASSOCIATES

  1302 Raintree Place, Winter Park, FL 32789
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  /16

  $1,500 Per Month

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

  7340 Swallow Run Unit 7340, Winter Park, FL 32792

  Check out this 2nd floor 2-bedroom, 2 bathroom condo with brand new beautiful wood floors throughout. The condo is centrally located between UCF and Full Sail University and is just a short distance to major roadways, shopping, and several dining options.

  Bobby Mills METRO CITY REALTY

  7340 Swallow Run Unit 7340, Winter Park, FL 32792
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  /2

  $975,000 Sold Feb 10, 2026

  1150 Kenwood Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,557 Sq Ft
  • Built 1988

  Last Sold Summary

  • 24% Below List Price
  • $381/SF
  • 97 Days On Market

  Current Estimated Value $1,022,572

  Last Listing Agent JJ Mackle PREMIER SOTHEBY'S INTL. REALTY

  1150 Kenwood Ave, Winter Park, FL 32789
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  /43

  Est $754,705 Not Listed For Sale

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft
  • Built 2016

  7984 Pleasant Pine Cir, Winter Park, FL 32792

  Last Sold Summary

  • 1% Above List Price
  • $215/SF
  • 0 Days On Market

  • Last Sold Price $750,000
  • Dec 18, 2023

  Last Listing Agent Kimberley Gernert LLC BALDWIN PARK REALTY LLC
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  /30

  $295,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,178 Sq Ft

  5473 Bracken Ct, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Move-in ready 3-bedroom, 2-bath townhome in desirable Winter Park featuring recent exterior paint and a clean, modern presentation throughout. BRAND NEW water heater, A/C replaced in 2021, and NEW ROOF (2026). The spacious family room sits beneath dramatic two-story vaulted ceilings highlighted by

  David Fraser KELLER WILLIAMS ADVANTAGE III

  5473 Bracken Ct, Winter Park, FL 32792
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  /29

  $2,650 Per Month

  • 4 Beds
  • 2 Baths
  • 2,053 Sq Ft
  • House for Rent

  7619 Georgeann St, Winter Park, FL 32792

  Welcome to 7619 Georgeann Street, a beautifully appointed 2,053+ sq. ft. single-family home that captures the essence of modern living in one of Winter Park’s most desirable neighborhoods. Thoughtfully designed and meticulously maintained, this residence offers the perfect blend of sophistication, comfort, and everyday functionality. Step through the front door and instantly feel the openness

  Ting Li SOUTH EARTH REALTY LLC

  7619 Georgeann St, Winter Park, FL 32792
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  /2

  $415,000 Sold Mar 04, 2026

  1816 Ivy Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,725 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $241/SF
  • 139 Days On Market

  Current Estimated Value $417,558

  Last Listing Agent Michael Cameron CAMERON REALTY GROUP LLC

  1816 Ivy Ln, Winter Park, FL 32792
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  /40

  Est $814,096 Not Listed For Sale

  2035 Soaring Oak Way, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 2,706 Sq Ft
  • Built 2021

  2035 Soaring Oak Way, Winter Park, FL 32792

  Last Sold Summary

  • 4% Above List Price
  • $290/SF
  • 130 Days On Market

  • Last Sold Price $785,000
  • Apr 15, 2024

  Last Listing Agent Kimberly Slinger KELLY PRICE & COMPANY LLC
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  /11

  $317,500

  • 3 Beds
  • 2 Baths
  • 1,392 Sq Ft

  121 Stefanik Rd, Winter Park, FL 32792

  A MUST SEE! Beautifully remodeled 3 bedroom 2 bath home. Third bedroom has its own separate entrance as well. Large foyer and living room. Kitchen has beautiful 40 inch cabinets and granite counter tops. Septic system was just replaced in September. Close to everything.

  Moe Mossa SAVVY AVENUE, LLC

  121 Stefanik Rd, Winter Park, FL 32792
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  /15

  $2,095 Per Month

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • House for Rent

  1724 Peruvian Ln, Winter Park, FL 32792

  Live in this updated home in Winter Park with 3 bedroom, 2 bathrooms. Large formal living area and a separate family room with dining. Kitchen with Stainless Steel appliances, Granite counter tops throughout, Ceramic Tile and Carpet flooring. Freshly painted interior and exterior. Large, fenced backyard. Laundry-room with Washer/Dryer hookups. *Bonus Amenity Included* - All residents are enrolled

  Mo Jabr RE/MAX 200 REALTY

  1724 Peruvian Ln, Winter Park, FL 32792
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  $170,000 Sold Sep 24, 2025

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Built 1970

  Last Sold Summary

  • 10% Below List Price
  • $152/SF
  • 74 Days On Market

  Current Estimated Value $175,757

  Last Listing Agent Evelyn Pilchick RE/MAX 200 REALTY

  200 Saint Andrews Blvd Unit 2607, Winter Park, FL 32792
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  /25

  Est $236,500 Not Listed For Sale

  5408 Peaco Place, Winter Park, FL 32792

  • 3 Beds
  • 1.5 Baths
  • 1,439 Sq Ft
  • Built 1984

  5408 Peaco Place, Winter Park, FL 32792

  Last Sold Summary

  • 3% Above List Price
  • $160/SF
  • 24 Days On Market

  • Last Sold Price $230,000
  • Dec 11, 2023

  Last Listing Agent John Harbuck SERHANT
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  /42

  $800,000

  • 5 Beds
  • 3 Baths
  • 2,194 Sq Ft

  739 Roughbeard Rd, Winter Park, FL 32792

  Welcome to Winter Park Pines, one of Winter Park’s most desirable neighborhoods. This updated 5 bed, 3 bath pool home features a split floor plan, generous room sizes, and wood-plank tile flooring throughout most of the home. Inside, the formal living and dining rooms flow together and overlook the pool through French doors, while the large primary suite offers an en-suite bath, walk-in closet,

  John Harbuck SERHANT

  739 Roughbeard Rd, Winter Park, FL 32792
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  /2

  $475,000 Sold Feb 02, 2026

  1740 Anzle Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,808 Sq Ft
  • Built 1956

  Last Sold Summary

  • 40% Below List Price
  • $263/SF
  • 109 Days On Market

  Current Estimated Value $545,318

  Last Listing Agent Freddy DeCoster GOYAL & DECOSTER REALTY

  1740 Anzle Ave, Winter Park, FL 32789
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  /16

  Est $1,001,293 Not Listed For Sale

  2400 Roxbury Rd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,110 Sq Ft
  • Built 2023

  2400 Roxbury Rd, Winter Park, FL 32789

  Last Sold Summary

  • $321/SF
  • 55 Days On Market

  • Last Sold Price $997,500
  • Dec 29, 2023

  Last Listing Agent Sherri Dyer PREMIER SOTHEBY'S INTL. REALTY
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  /29

  $415,000

  • 3 Beds
  • 2 Baths
  • 1,197 Sq Ft

  1518 Pinewood Dr, Winter Park, FL 32789

  Income-producing home with a detached in-law apartment in a prime central Orlando location — ideal for a house hack, long-term rental, or short-term rental (Airbnb allowed). The main house is a two-bedroom, one-bath residence, while the in-law apartment is a completely detached one-bedroom, one-bath unit with separate entrances and separate mailboxes, offering excellent privacy and flexibility.

  Dan Grieb KELLER WILLIAMS REALTY AT THE PARKS

  1518 Pinewood Dr, Winter Park, FL 32789
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  /2

  $325,000 Sold Oct 03, 2025

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 1,140 Sq Ft
  • Built 1986

  Last Sold Summary

  • 6% Below List Price
  • $285/SF
  • 0 Days On Market

  Current Estimated Value $326,560

  Last Listing Agent Tyler Gibson LPT REALTY, LLC

  260 Killarney Bay Ct Unit 6, Winter Park, FL 32789
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  /19

  Est $2,567,451 Not Listed For Sale

  350 Beloit Ave, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 3,205 Sq Ft
  • Built 2018

  350 Beloit Ave, Winter Park, FL 32789

  Last Sold Summary

  • 7% Below List Price
  • $858/SF
  • 0 Days On Market

  • Last Sold Price $2,750,000
  • Oct 24, 2023

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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  /28

  $170,000

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792

  Beautifully maintained condo in a prime Winter Park location! This bright and inviting unit has been exceptionally well cared for and shows true pride of ownership. The interior is spotless, featuring a clean, modern feel with comfortable living spaces that make it easy to feel right at home. Enjoy a well-designed layout with plenty of natural light and a welcoming atmosphere throughout. The

  Reinaldo Roman ROMAN'S PRO REALTY LLC

  200 Saint Andrews Blvd Unit 312, Winter Park, FL 32792
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  /2

  $1,725,000 Sold Mar 05, 2026

  617 Worthington Dr, Winter Park, FL 32789

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft
  • Built 2018

  Last Sold Summary

  • 13% Below List Price
  • $488/SF
  • 215 Days On Market

  Current Estimated Value $1,830,263

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, Winter Park, FL 32789
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  /35

  Est $282,467 Not Listed For Sale

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft
  • Built 1985

  228 Balfour Dr Unit 17, Winter Park, FL 32792

  Last Sold Summary

  • 4% Below List Price
  • $229/SF
  • 213 Days On Market

  • Last Sold Price $294,999
  • May 21, 2024

  Last Listing Agent William Grim, III RE/MAX
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  /6

  $795,000

  • Land
  • 9,583 Sq Ft
  • $3,613,636 per Acre

  325 N Phelps Ave, Winter Park, FL 32789

  Fantastic lot opportunity to build in one of Winter Park’s prime neighborhoods. Bring your vision and your builder to design a home tailored to your lifestyle on this 64-by-150-foot lot. The property includes a two-bedroom, one-bath single-family home with approximately 1,400 square feet of living space, making it an ideal potential income-producing property while you finalize your plans. Whether

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

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

  $415,000 Sold Jun 10, 2025

  3063 Ash Park Loop, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1987

  Last Sold Summary

  • 1% Below List Price
  • $248/SF
  • 23 Days On Market

  Current Estimated Value $420,219

  Last Listing Agent Cheryl Anderson ANDERSON INVESTMENT PROPERTIES

  3063 Ash Park Loop, Winter Park, FL 32792
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  /80

  Est $1,174,968 Not Listed For Sale

  1999 Soaring Oak Way, Winter Park, FL 32792

  • 5 Beds
  • 4.5 Baths
  • 4,307 Sq Ft
  • Built 2019

  1999 Soaring Oak Way, Winter Park, FL 32792

  Last Sold Summary

  • 2% Below List Price
  • $279/SF
  • 5 Days On Market

  • Last Sold Price $1,200,000
  • Nov 08, 2023

  Last Listing Agent Mulcy Tenorio FLORIDA CONNEXION PROPERTIES
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  /39

  $375,000

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft

  819 Densmore Dr, Winter Park, FL 32792

  Welcome to 819 Densmore Drive, a beautifully refreshed concrete block ranch home in the heart of Winter Park Estates, one of Winter Park's most established neighborhoods with no HOA. This move-in ready home checks every box for buyers who want turn-key condition with an accessible price and a coveted Winter Park address. From the moment you pull up, the curb appeal speaks for itself. A crisp

  Don Harkins DON HARKINS REALTY LLC

  819 Densmore Dr, Winter Park, FL 32792
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  /2

  $385,000 Sold Nov 12, 2025

  4421 Steed Terrace, Winter Park, FL 32792

  • 4 Beds
  • 2.5 Baths
  • 1,788 Sq Ft
  • Built 1989

  Last Sold Summary

  • 14% Below List Price
  • $215/SF
  • 209 Days On Market

  Current Estimated Value $380,923

  Last Listing Agent Andrey Bustamante BUSTAMANTE REAL ESTATE INC

  4421 Steed Terrace, Winter Park, FL 32792
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  /11

  Est $436,004 Not Listed For Sale

  2770 Bright Bird Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft
  • Built 2024

  2770 Bright Bird Ln, Winter Park, FL 32792

  Last Sold Summary

  • 5% Below List Price
  • $258/SF
  • 99 Days On Market

  • Last Sold Price $459,990
  • May 17, 2024

  Last Listing Agent Ian Medina PULTE REALTY OF NORTH FLORIDA LLC
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  /33

  $320,000

  • 3 Beds
  • 2 Baths
  • 1,719 Sq Ft

  2401 Antilles Dr, Winter Park, FL 32792

  Fantastic end unit with enclosed Florida Room in the sought after Windward Square! This 3/2 features several updates including a, updated kitchen with 42" wood cabinets, granite counters and a center island! Most rooms have upgraded ceiling fans from Dan”s Fans with a lifetime guarantee. The home has newer A/C, high impact windows and the home has been re-piped for your peace of mind. This is a

  George Freelove KELLER WILLIAMS REALTY AT THE PARKS

  2401 Antilles Dr, Winter Park, FL 32792
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  /2

  $665,000 Sold Jun 18, 2025

  2817 Prince John Rd, Winter Park, FL 32792

  • 4 Beds
  • 3.5 Baths
  • 2,183 Sq Ft
  • Built 1963

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 37 Days On Market

  Current Estimated Value $653,127

  Last Listing Agent Lori Gilmore LORI GILMORE REAL ESTATE LLC

  2817 Prince John Rd, Winter Park, FL 32792
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  /46

  Est $930,478 Not Listed For Sale

  1913 S Lakemont Ave, Winter Park, FL 32792

  • 3 Beds
  • 3.5 Baths
  • 2,085 Sq Ft
  • Built 2023

  1913 S Lakemont Ave, Winter Park, FL 32792

  Last Sold Summary

  • 13% Below List Price
  • $516/SF
  • 119 Days On Market

  • Last Sold Price $1,075,000
  • Mar 04, 2024

  Last Listing Agent Nickolas McKee KELLER WILLIAMS WINTER PARK
• 

  

  /23

  $650,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,150 Sq Ft

  661 Selkirk Dr, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to the highly sought-after Kenilworth Shores community, a neighborhood loved for its charm, strong sense of community, and convenient Winter Park lifestyle. From the moment you walk through the front door, the home offers a warm and welcoming flow with a thoughtfully designed split layout. The spacious

  David Miller KELLER WILLIAMS HERITAGE REALTY

  661 Selkirk Dr, Winter Park, FL 32792
• 

  /2

  $2,835,000 Sold Nov 24, 2025

  255 Stirling Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,635 Sq Ft
  • Built 1982

  Last Sold Summary

  • 14% Below List Price
  • $780/SF
  • 25 Days On Market

  Current Estimated Value $2,830,977

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

  255 Stirling Ave, Winter Park, FL 32789

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