Homes in ZIP Code 32789

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  /54

  $3,270,000

  • 5 Beds
  • 5.5 Baths
  • 4,955 Sq Ft

  1761 Legion Dr, Winter Park, FL 32789

  One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

  Brian Scanlon SCANLON REALTY GROUP LLC

  1761 Legion Dr, Winter Park, FL 32789
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  /2

  $4,430,000 Sold Oct 09, 2025

  2161 Sharon Rd, Winter Park, FL 32789

  • 5 Beds
  • 6.5 Baths
  • 6,338 Sq Ft
  • Built 2023

  Last Sold Summary

  • 11% Below List Price
  • $699/SF
  • 247 Days On Market

  Current Estimated Value $4,361,685

  Last Listing Agent Marcio Tannus LA ROSA REALTY HORIZONS LLC

  2161 Sharon Rd, Winter Park, FL 32789
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  /2

  Est $1,205,029 Not Listed For Sale

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,734 Sq Ft
  • Built 2008

  335 W Welbourne Ave Unit 103, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $454/SF
  • 184 Days On Market

  • Last Sold Price $1,242,000
  • Feb 07, 2025

  Last Listing Agent Gernelle Bokuniewicz LIVELY REAL ESTATE
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  /58

  $2,195,000

  • 4 Beds
  • 3.5 Baths
  • 3,450 Sq Ft

  1398 Grove Terrace, Winter Park, FL 32789

  Welcome to your private slice of paradise, perfectly positioned on a charming brick-lined street in the heart of historic Winter Park. This custom-built estate exudes casual elegance from the moment you step through the grand double door entry, where soaring 12-foot ceilings, rich architectural details, and exceptional craftsmanship immediately set the tone. Thoughtfully designed with a

  Liz Jones ORANGE SLICE PROPERTIES

  1398 Grove Terrace, Winter Park, FL 32789
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  /2

  $519,180 Sold Jul 08, 2025

  2518 Sweetwater Trail, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,205 Sq Ft
  • Built 1965

  Last Sold Summary

  • 21% Below List Price
  • $235/SF
  • 201 Days On Market

  Current Estimated Value $579,566

  Last Listing Agent Joseph Doher BERKSHIRE HATHAWAY HOMESERVICES RESULTS REALTY

  2518 Sweetwater Trail, Winter Park, FL 32789
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  /2

  Est $291,812 Not Listed For Sale

  500 N Pennsylvania Ave Unit G, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 709 Sq Ft
  • Built 1981

  500 N Pennsylvania Ave Unit G, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $409/SF
  • 76 Days On Market

  • Last Sold Price $290,000
  • Aug 28, 2024

  Last Listing Agent Drew Henner PREMIER SOTHEBY'S INTL. REALTY
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  /34

  $289,900

  • 1 Bed
  • 1 Bath
  • 482 Sq Ft

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. One or more photos have been virtually staged. Welcome to an exceptional opportunity to own a beautifully maintained, move-in ready third-floor, water-view, corner unit studio residence in one of Winter Park’s most coveted locations—directly adjacent to Lake Osceola and just moments from iconic Park Avenue. This rare downtown setting places you

  Mathew Kelly TURN-KEY MOVES REALTY

  311 E Morse Blvd Unit 7-19, Winter Park, FL 32789
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  /2

  $1,565,000 Sold Sep 24, 2025

  1450 Glencoe Rd, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,662 Sq Ft
  • Built 1952

  Last Sold Summary

  • 1% Below List Price
  • $588/SF
  • 42 Days On Market

  Current Estimated Value $1,566,182

  Last Listing Agent MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1450 Glencoe Rd, Winter Park, FL 32789
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  /19

  Not Listed For Sale

  200 Carolina Ave Unit 402A, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,350 Sq Ft
  • Built 1982

  200 Carolina Ave Unit 402A, Winter Park, FL 32789

  Last Sold Summary

  • $463/SF
  • 74 Days On Market

  • Last Sold Price $625,000
  • Jun 02, 2023

  Last Listing Agent A.V. Blalock COLDWELL BANKER REALTY
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  /29

  $725,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft

  1550 Norfolk Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Welcome to this exceptional residence at 1550 Norfolk Ave, perfectly positioned in the highly sought-after Orwin Manor neighborhood of Winter Park. Set on a spacious corner lot, this beautifully maintained home offers 3 bedrooms and a rare 3-car garage, combining comfort, functionality, and timeless appeal. Inside, you’ll find rich hardwood floors,

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  1550 Norfolk Ave, Winter Park, FL 32789
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  /2

  $414,000 Sold Feb 19, 2026

  740 Baffie Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft
  • Built 1960

  Last Sold Summary

  • 12% Below List Price
  • $284/SF
  • 94 Days On Market

  Current Estimated Value $414,001

  Last Listing Agent Chris Creegan CREEGAN GROUP

  740 Baffie Ave, Winter Park, FL 32789
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  /2

  Est $328,853 Not Listed For Sale

  1132 Park Green Place, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,282 Sq Ft
  • Built 1991

  1132 Park Green Place, Winter Park, FL 32789

  Last Sold Summary

  • 6% Below List Price
  • $273/SF
  • 1 Day On Market

  • Last Sold Price $350,000
  • Sep 06, 2024

  Last Listing Agent Christi Nixon CHARLES RUTENBERG REALTY ORLANDO
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  /27

  $1,295,000

  • 2 Beds
  • 3 Baths
  • 2,096 Sq Ft

  1500 Harris Cir, Winter Park, FL 32789

  Tucked along one of Winter Park’s charming brick streets and positioned directly across from Lake Sylvan, this recently renovated residence unfolds like a quiet design story, one where character, craftsmanship and modern ease are aligned. From the moment you arrive, the home’s inviting curb appeal and reimagined cottage gardens set the tone, offering a sense of arrival that feels timeless and

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1500 Harris Cir, Winter Park, FL 32789
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  /2

  $2,250,000 Sold Nov 17, 2025

  600 Ololu Dr, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,749 Sq Ft
  • Built 2004

  Last Sold Summary

  • 2% Below List Price
  • $600/SF
  • 2 Days On Market

  Current Estimated Value $2,188,666

  Last Listing Agent David Francetic COLDWELL BANKER REALTY

  600 Ololu Dr, Winter Park, FL 32789
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  /50

  Est $1,652,119 Not Listed For Sale

  1420 Magnolia Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,174 Sq Ft
  • Built 2015

  1420 Magnolia Ave, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $488/SF
  • 1 Day On Market

  • Last Sold Price $1,550,000
  • Dec 18, 2023

  Last Listing Agent Dave Zembala ZEMBALA GROUP
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  /31

  $2,272,000

  • 3 Beds
  • 4.5 Baths
  • 3,272 Sq Ft

  147 S Interlachen Ave Unit 202, Winter Park, FL 32789

  Welcome to 147 Interlachen Place, Enjoy Winter Park's most desirable location! One block from Historic Park Avenue/Central Park. Spacious, bright and all on ONE FLOOR. The buildings second floor offers privacy and easy access. The Southwest corner provides direct natural light throughout the day. Private elevator access with secured underground parking. This beautiful home offers a short walk to

  Dan Farber HELLOSOLD LLC

  147 S Interlachen Ave Unit 202, Winter Park, FL 32789
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  /2

  $645,000 Sold Jun 13, 2025

  796 Mcintyre Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,910 Sq Ft
  • Built 1988

  Last Sold Summary

  • 4% Below List Price
  • $338/SF
  • 18 Days On Market

  Current Estimated Value $652,793

  Last Listing Agent Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  796 Mcintyre Ave, Winter Park, FL 32789
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  /2

  Est $687,469 Not Listed For Sale

  1580 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1971

  1580 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • 13% Above List Price
  • $409/SF
  • 4 Days On Market

  • Last Sold Price $606,000
  • Oct 17, 2024

  Last Listing Agent Nicole Howell FANNIE HILLMAN & ASSOCIATES
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  /2

  $1,375,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  266 W Lyman Ave, Winter Park, FL 32789

  ONE BLOCK FROM PARK AVENUE! Welcome to this beautifully renovated townhouse in the heart of Winter Park, offering the perfect blend of luxury and convenience. Whether you're looking for a full-time residence or a lock-and-leave property, this home delivers on every level. Designed with entertaining in mind, the open-concept layout creates a seamless flow from the kitchen into the main living

  Larry Lanpher MAROON REALTY GROUP LLC

  266 W Lyman Ave, Winter Park, FL 32789
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  /2

  $560,000 Sold Jan 27, 2026

  1875 Staunton Ave, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 2,036 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Below List Price
  • $275/SF
  • 89 Days On Market

  Last Listing Agent Jill Healey KELLER WILLIAMS WINTER PARK

  1875 Staunton Ave, Winter Park, FL 32789
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  /2

  Est $895,144 Not Listed For Sale

  1762 Chestnut Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,760 Sq Ft
  • Built 1957

  1762 Chestnut Ave, Winter Park, FL 32789

  Last Sold Summary

  • $511/SF
  • 37 Days On Market

  • Last Sold Price $899,000
  • Dec 27, 2024

  Last Listing Agent Heather Frazee FANNIE HILLMAN & ASSOCIATES
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  /39

  $1,249,900 Pending

  • 4 Beds
  • 3.5 Baths
  • 2,984 Sq Ft

  1737 Indiana Ave, Winter Park, FL 32789

  Under Construction. Under Construction. *** NEW CONSTRUCTION*** Pictures shown are of the model home with comparable finishes. Welcome to Winter Park!! This stunning new Modern Farmhouse is meticulously appointed and is conveniently located to everything Winter Park and College Park has to offer. As you step up to the front door- a welcoming front porch greets you with warmth and the attention to

  Amanda Wood RE/MAX EXCLUSIVE COLLECTION

  1737 Indiana Ave, Winter Park, FL 32789
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  /2

  $569,000 Sold May 30, 2025

  1368 Devon Rd, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft
  • Built 1952

  Last Sold Summary

  • $347/SF
  • 5 Days On Market

  Current Estimated Value $579,843

  Last Listing Agent Karen Ripperger LPT REALTY, LLC

  1368 Devon Rd, Winter Park, FL 32789
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  /2

  Est $1,801,719 Not Listed For Sale

  1530 Via Tuscany, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 3,341 Sq Ft
  • Built 1972

  1530 Via Tuscany, Winter Park, FL 32789

  Last Sold Summary

  • 13% Above List Price
  • $479/SF
  • 377 Days On Market

  • Last Sold Price $1,600,000
  • Dec 16, 2024

  Last Listing Agent Dan Haber CORCORAN PREMIER REALTY
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  /37

  $1,349,000

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

  802 Hamilton Place Ct, Winter Park, FL 32789

  Built in 2018, this beautifully designed 4-bedroom, 3.5-bath home offers 2,843 square feet of refined living in a prime Winter Park location, walking distance to Park Avenue and the renowned Winter Park 9 golf course. Thoughtful architectural details set it apart, including shiplap ceilings in the living room and kitchen, decorative ceiling finishes in the bedrooms, and a striking tile staircase

  Jacob Theisen FLORIDA CAPITAL REALTY

  802 Hamilton Place Ct, Winter Park, FL 32789
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  /2

  $2,935,000 Sold May 27, 2025

  266 Chase Ave, Winter Park, FL 32789

  • 5 Beds
  • 5.5 Baths
  • 4,088 Sq Ft
  • Built 1930

  Last Sold Summary

  • 10% Below List Price
  • $718/SF
  • 30 Days On Market

  Current Estimated Value $2,854,279

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  266 Chase Ave, Winter Park, FL 32789
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  /2

  Est $689,236 Not Listed For Sale

  678 Depugh St, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 1952

  678 Depugh St, Winter Park, FL 32789

  Last Sold Summary

  • 2% Above List Price
  • $348/SF
  • 89 Days On Market

  • Last Sold Price $675,000
  • Jan 29, 2025

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK
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  /43

  $1,599,000

  • 5 Beds
  • 3.5 Baths
  • 3,028 Sq Ft

  1864 Grinnell Terrace, Winter Park, FL 32789

  Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the

  Robyn Brehne COLDWELL BANKER REALTY

  1864 Grinnell Terrace, Winter Park, FL 32789
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  /2

  $2,100,000 Sold Jul 07, 2025

  104 Cortland Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,182 Sq Ft
  • Built 1926

  Last Sold Summary

  • 12% Below List Price
  • $660/SF
  • 36 Days On Market

  Current Estimated Value $2,042,447

  Last Listing Agent Mick Night PREMIER SOTHEBY'S INTL. REALTY

  104 Cortland Ave, Winter Park, FL 32789
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  /2

  Est $969,096 Not Listed For Sale

  1875 Lake Spier Dr, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,366 Sq Ft
  • Built 1958

  1875 Lake Spier Dr, Winter Park, FL 32789

  Last Sold Summary

  • 1% Below List Price
  • $717/SF
  • 33 Days On Market

  • Last Sold Price $980,000
  • Nov 01, 2024

  Last Listing Agent Angelina Cyprich FLORIDA REALTY INVESTMENTS
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  /47

  $1,875,000

  • 4 Beds
  • 4.5 Baths
  • 3,657 Sq Ft

  543 E Lake Sue Ave, Winter Park, FL 32789

  Welcome to Timberlane Shores—one of Winter Park’s most desirable neighborhoods! This beautiful 4-bedroom, 4.5-bath home sits on over a third of an acre in a quiet, tucked-away location with gorgeous updated landscaping. Inside, you’ll find wide-plank hardwood floors throughout and a thoughtfully designed floor plan with separate living and dining rooms plus a spacious family room. The bright

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  543 E Lake Sue Ave, Winter Park, FL 32789
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  /2

  $620,000 Sold Apr 10, 2026

  1137 Oaks Blvd, Winter Park, FL 32789

  • 2 Beds
  • 1.5 Baths
  • 1,149 Sq Ft
  • Built 1958

  Last Sold Summary

  • 4% Below List Price
  • $540/SF
  • 44 Days On Market

  Current Estimated Value $622,786

  Last Listing Agent David Gallup RE/MAX 200 REALTY

  1137 Oaks Blvd, Winter Park, FL 32789
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  /2

  Est $435,768 Not Listed For Sale

  1501 Michigan Ave, Winter Park, FL 32789

  • 2 Beds
  • 1 Bath
  • 853 Sq Ft
  • Built 1936

  1501 Michigan Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Below List Price
  • $528/SF
  • 5 Days On Market

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

  Last Listing Agent Brad Corbitt CREEGAN GROUP
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  /64

  $2,295,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,963 Sq Ft

  2015 N Park Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. Boasting a prestigious Park Avenue address, this striking modern architectural residence perfectly balances bold design with spa-like serenity. Set on a beautifully landscaped corner lot, the home embodies the rare combination of privacy and proximity, just a leisurely 25-minute stroll from Park Avenue’s world-class boutiques and dining. Every element of

  Julie Christensen ONE LUXURY INTERNATIONAL LLC

  2015 N Park Ave, Winter Park, FL 32789
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  /2

  $749,000 Sold Aug 01, 2025

  1429 Indiana Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 1,939 Sq Ft
  • Built 2019

  Last Sold Summary

  • 6% Below List Price
  • $386/SF
  • 63 Days On Market

  Current Estimated Value $756,631

  Last Listing Agent Jennifer Sloan COMPASS FLORIDA LLC

  1429 Indiana Ave, Winter Park, FL 32789
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  /56

  Est $1,848,506 Not Listed For Sale

  914 Moss Ln, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,431 Sq Ft
  • Built 1955

  914 Moss Ln, Winter Park, FL 32789

  Last Sold Summary

  • 7% Above List Price
  • $503/SF
  • 2 Days On Market

  • Last Sold Price $1,725,000
  • Mar 08, 2024

  Last Listing Agent Alison Mosley PREMIER SOTHEBY'S INTL. REALTY
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  /39

  $835,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,237 Sq Ft

  1018 Turner Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. Seller may consider buyer concessions if made in an offer | Lakefront charm meets quiet luxury in the heart of Winter Park! This beautifully updated single story POOL HOME sits on nearly HALF AN ACRE of LAKEFRONT PROPERTY on the coveted LAKE BELL - a private SKI LAKE - offering a private dock/boat lift, character and contemporary upgrades that make everyday

  Jennifer Wemert WEMERT GROUP REALTY LLC

  1018 Turner Rd, Winter Park, FL 32789
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  /2

  $819,000 Sold Oct 31, 2025

  734 Maryland Ave, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1926

  Last Sold Summary

  • 3% Below List Price
  • $655/SF
  • 44 Days On Market

  Current Estimated Value $809,428

  Last Listing Agent Michael Domi COMPASS FLORIDA LLC

  734 Maryland Ave, Winter Park, FL 32789
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  /39

  Est $1,097,468 Not Listed For Sale

  1771 Bryan Ave, Winter Park, FL 32789

  • 3 Beds
  • 2.5 Baths
  • 2,507 Sq Ft
  • Built 1993

  1771 Bryan Ave, Winter Park, FL 32789

  Last Sold Summary

  • $439/SF
  • 42 Days On Market

  • Last Sold Price $1,100,000
  • May 28, 2024

  Last Listing Agent Chase Morton Tate COMPASS FLORIDA LLC
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  /31

  $2,195,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,412 Sq Ft

  1636 Elizabeths Walk, Winter Park, FL 32789

  Under contract-accepting backup offers. Discover refined living in this stunning custom-built home located in the coveted community of Windsong. Thoughtfully designed and expertly constructed by Goehring & Morgan, this four-bedroom, 4.5 bath residence offers a perfect balance of elegance, comfort and functionality. From the moment you enter, the home impresses with its airy, open-concept design,

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1636 Elizabeths Walk, Winter Park, FL 32789

Showing Results 641 - 680, Page 17 of 18