Winter Park, FL Homes

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  /22

  $262,000

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

  1500 Gay Rd Unit 20D, Winter Park, FL 32789

  LAKEFRONT COMMUNITY WITH SPECTACULAR SUNSETS OVER BEAUTIFUL LAKE KILLARNEY. LOCATED IN THE CHARMING AND ELLEGANT NEIGHBORHOOD OF WINTER PARK, IN A FULLY REVITALIZED AREA.CONVENIENT TO I-4, PARK AVENUE, FARMER'S MARKETS, TRADER JOE'S, AS WELL AS A MOVIE THEATER, BOUTIQUE SHOPS, RENOWNED RESTAURANTS AND A NATIONALLY RATED ART FESTIVAL - ALL WITHIN A SHORT WALKING DISTANCE.BRIGHT SUN-FILLED

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (689) 399-5336

  1500 Gay Rd Unit 20D, Winter Park, FL 32789
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  /50

  $1,585 - $3,136 per month

  Seven41 Winter Park

  Studio - 2 Beds

  741 Clay St, Winter Park, FL 32789

  Welcome to Seven41 (Formerly known as Winter Park 2) featuring Winter Park, FL vibe with a gorgeous modern style. Brand new studio, one, and two bedroom apartments amplified by unrivaled finishes and amenities. Select Seven41 for its luxury.

  741 Clay St, Winter Park, FL 32789
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  /2

  $730,000 Sold Mar 23, 2026

  1213 Lindenwood Ln, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 2,505 Sq Ft
  • Built 1960

  Last Sold Summary

  • 3% Below List Price
  • $291/SF
  • 81 Days On Market

  Current Estimated Value $726,130

  Last Listing Agent Amy Turner KELLER WILLIAMS WINTER PARK

  1213 Lindenwood Ln, Winter Park, FL 32792
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  /6

  Est $522,059 Not Listed For Sale

  2613 Lafayette Ave, Winter Park, FL 32789

  • 2 Beds
  • Built 1956

  2613 Lafayette Ave, Winter Park, FL 32789

  Last Sold Summary

  • $586/SF
  • 148 Days On Market

  Last Sold Price $520,000

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC
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  /21

  $264,000

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

  1500 Gay Rd Unit 24B, Winter Park, FL 32789

  ANOTHER PRICE REDUCTION! OWNER WILL CONSIDER ALL REASONABLE OFFERS!Highly Desirable Winter Park Lakefront Community on Skiable Lake Killarney. Enjoy Peaceful Water Views and Million-Dollar Sunsets on Lakefront Deck! Private Community Ramp, Heated Pool, Men's and Women's Saunas!Don't miss this! Beautifully Renovated 2 Bedroom 2 Bath End Unit. New Kitchen Cabinets and Quartz Counters,

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  (321) 450-8960

  1500 Gay Rd Unit 24B, Winter Park, FL 32789
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  /18

  $2,167 per month

  • 4 Beds
  • 2 Baths
  • 1,411 Sq Ft
  • House for Rent

  717 Denton Rd, Winter Park, FL 32792

  Winter Park 4 Bedrm Home for Rent!Priced Low, Call Now!, 2 Car Carport, Bonus Room Too!, Eat In Kitchen, JUST 20 MINUTES To: Downtown Orlando, JUST 30 MINUTES To: The Orlando Airport, CONVENIENT To: 436, CONVENIENT To: Major Roads, Shopping & Schools, CONVENIENT To: Full Sail University, Stainless Steel Appliances INCLUDED, Blinds INCLUDED. The deposit amount is based upon the application

  Jay Myers ORLANDO REALTY & PROPERTY MGNT

  717 Denton Rd, Winter Park, FL 32792
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  /2

  $1,590,000 Sold Mar 06, 2026

  1166 Oaks Blvd, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,860 Sq Ft
  • Built 2018

  Last Sold Summary

  • 12% Below List Price
  • $556/SF
  • 153 Days On Market

  Current Estimated Value $1,580,246

  Last Listing Agent Kevin Kelly FANNIE HILLMAN & ASSOCIATES

  1166 Oaks Blvd, Winter Park, FL 32789
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  /19

  Not Listed For Sale

  2076 Leanne Ct, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,729 Sq Ft
  • Built 1969

  2076 Leanne Ct, Winter Park, FL 32792

  Last Sold Summary

  • $252/SF
  • 6 Days On Market

  Last Sold Price $436,000

  Last Listing Agent Julian Jackson LOKATION
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  /31

  $740,000

  • 2 Beds
  • 1 Bath
  • 1,396 Sq Ft

  841 W Swoope Ave, Winter Park, FL 32789

  Build your custom Winter Park home on one of the last available lots in this coveted 32789 corridor. Located at 841 W Swoope Ave, this 9,752 SF R-2 zoned parcel sits on W Swoope Avenue between Park Avenue and Orlando Avenue — walking distance to Winter Park Village, top-rated Winter Park schools, and the newly revitalized Park Avenue district. The existing shell structure is demo-ready, clearing

  

  Evelyn Alicea

  EXP REALTY LLC

  (321) 468-9259

  841 W Swoope Ave, Winter Park, FL 32789
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  /36

  $1,201 - $2,029 per month

  The Taylor at Winter Park

  Studio - 3 Beds

  2000 Village Ln, Winter Park, FL 32792

  5 miles north of Orlando lies The Taylor at Winter Park. Experience true comfort and serenity in a newly renovated 1-, 2-, or 3-bedroom apartment. With spacious home layouts, sleek interior finishes, screened porches, private balconies, and stunning garden-style landscaping, you can enjoy a healthy, Zen lifestyle. Cut your commute and enjoy going out on the town with a prime location near

  2000 Village Ln, Winter Park, FL 32792
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  /2

  $245,000 Sold Jun 26, 2025

  2471 Tahoe Cir, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,295 Sq Ft
  • Built 1981

  Last Sold Summary

  • 6% Below List Price
  • $189/SF
  • 84 Days On Market

  Current Estimated Value $228,902

  Last Listing Agent Kevin Wilhelm MLSB THE BUREAU POWERED BY CAROM REALTY

  2471 Tahoe Cir, Winter Park, FL 32792
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  /2

  Est $475,995 Not Listed For Sale

  1937 Eland Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1957

  1937 Eland Ave, Winter Park, FL 32789

  Last Sold Summary

  • 3% Above List Price
  • $295/SF
  • 22 Days On Market

  Last Sold Price $460,000

  Last Listing Agent Courtney Pelfrey MILLER GRANT AND COMPANY
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  /78

  $1,399,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,459 Sq Ft

  102 Bell Place, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

  

  Freddie Crespo

  INVESTOR'S REAL ESTATE LLC

  (321) 490-4832

  102 Bell Place, Winter Park, FL 32792
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  /16

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 959 Sq Ft
  • Townhouse for Rent

  295 Sandlewood Trail, Winter Park, FL 32789

  This 2 bedroom, 2.5 bathroom townhome is located in Winter Park's desirable Sandlewood Creek community. Enjoy Park Avenue's shops and restaurants, Winter Park Village, highly rated schools, and an abundance of entertainment options to include Mead Gardens, WP Tennis Center, WP Golf Course, and much more. Features include a spacious main living area with open living room and dining room, a

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  295 Sandlewood Trail, Winter Park, FL 32789
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  /2

  $400,000 Sold Jul 16, 2025

  3443 Arnel Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1967

  Last Sold Summary

  • 6% Below List Price
  • $266/SF
  • 15 Days On Market

  Current Estimated Value $388,810

  Last Listing Agent Lana More KELLER WILLIAMS WINTER PARK

  3443 Arnel Dr, Winter Park, FL 32792
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  /2

  Est $355,252 Not Listed For Sale

  829 W New England Ave, Winter Park, FL 32789

  • 3 Beds
  • Built 1930

  829 W New England Ave, Winter Park, FL 32789

  Last Sold Summary

  • 4% Above List Price
  • $324/SF
  • 16 Days On Market

  Last Sold Price $340,000

  Last Listing Agent Jonathan Lacko WINTER PARK REAL ESTATE CO LLC
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  /41

  $2,249,900 Pending

  • 5 Beds
  • 4 Baths
  • 3,948 Sq Ft

  1205 Mayfield Ave, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This two-story property is located in the highly desired Temple Heights neighborhood in the heart of Winter Park, where the true value is in the prime location and expansive double lot. The property includes a main residence plus a separate pool home/in-law suite, offering flexibility for redevelopment,

  Abby Nelson RE/MAX 200 REALTY

  1205 Mayfield Ave, Winter Park, FL 32789
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  /50

  $1,499 - $2,018 per month

  Calibre Bend Apartments

  1 - 2 Beds

  3924 Calibre Bend Ln, Winter Park, FL 32792

  Calibre Bend Apartments offers a wide variety of apartment styles designed to accommodate the demands of today's sophisticated professional, while offering the setting and charm of yesteryear. You can expect unsurpassed amenities that will delight your senses, and a cozy community that makes coming home a breeze. Imagine your meals coming together perfectly in your gourmet kitchen, relaxing on

  3924 Calibre Bend Ln, Winter Park, FL 32792
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  /2

  $1,335,000 Sold Jul 15, 2025

  1077 Minnesota Ave, Winter Park, FL 32789

  • 4 Beds
  • 4 Baths
  • 3,046 Sq Ft
  • Built 2025

  Last Sold Summary

  • 1% Below List Price
  • $438/SF
  • 75 Days On Market

  Current Estimated Value $1,312,562

  Last Listing Agent Jake Johnson SHORES REAL ESTATE

  1077 Minnesota Ave, Winter Park, FL 32789
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  /49

  Est $1,667,650 Not Listed For Sale

  1781 Goodrich Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,701 Sq Ft
  • Built 2024

  1781 Goodrich Ave, Winter Park, FL 32789

  Last Sold Summary

  • 1% Above List Price
  • $611/SF
  • 88 Days On Market

  Last Sold Price $1,650,000

  Last Listing Agent Laura Hope COMPASS FLORIDA LLC
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  /52

  $350,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,404 Sq Ft

  5236 Tangerine Ave, Winter Park, FL 32792

  Under contract-accepting backup offers. HOME SWEET HOME – A curved driveway welcomes you to this charming ONE-STORY residence, where classic stone accents and green shutters peek through blooming azaleas, hinting at the warmth waiting inside. With its inviting cottage feel, this home blends character and comfort from the moment you arrive. Step through the covered entry into a space that feels

  Amber Finch FINCH REAL ESTATE COMPANY

  5236 Tangerine Ave, Winter Park, FL 32792
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  /34

  $4,000 per month

  • 4 Beds
  • 3.5 Baths
  • 2,196 Sq Ft
  • House for Rent

  1091 Wildmeadow Run, Winter Park, FL 32792

  1

  Maggie Walas FORTUNE INTERNATIONAL REALTY

  1091 Wildmeadow Run, Winter Park, FL 32792
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  /2

  $580,000 Sold Apr 21, 2025

  3006 Northwood Blvd, Winter Park, FL 32789

  • 4 Beds
  • 2 Baths
  • 1,710 Sq Ft
  • Built 1953

  Last Sold Summary

  • 2% Below List Price
  • $339/SF
  • 1 Day On Market

  Current Estimated Value $656,461

  Last Listing Agent Chris Creegan CREEGAN GROUP

  3006 Northwood Blvd, Winter Park, FL 32789
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  /2

  Est $3,396,363 Not Listed For Sale

  443 Lakewood Dr, Winter Park, FL 32789

  • 3 Beds
  • 5 Baths
  • 2,803 Sq Ft
  • Built 1954

  443 Lakewood Dr, Winter Park, FL 32789

  Last Sold Summary

  • 4% Below List Price
  • $1,267/SF
  • 0 Days On Market

  Last Sold Price $3,550,000

  Last Listing Agent Jenny Lake FANNIE HILLMAN & ASSOCIATES
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  /17

  $499,990

  • 4 Beds
  • 2 Baths
  • 1,376 Sq Ft

  501 Heritage Blvd, Winter Park, FL 32792

  Welcome to this fully remodeled, move-in ready home in the highly sought-after Winter Park area! This beautifully updated single-story residence features 4 bedrooms and 2 bathrooms, offering comfortable living with a bright and inviting layout.Step inside to discover a bright, open floor plan with modern finishes and thoughtfully updated living spaces, designed for both comfort and

  Bernardo Carrasquel B EXP REALTY LLC

  501 Heritage Blvd, Winter Park, FL 32792
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  /50

  $1,510 - $5,399 per month

  Berkshire Winter Park

  Studio - 3 Beds

  1874 Harmon Ave, Winter Park, FL 32789

  Cultivated Living; Rooted in Style! Well-appointed Studio, One, Two, & Three Bedroom Apartment Homes in Winter Park, FL.Berkshire Winter Park is an ultra-luxury apartment community with thoughtfully curated features and enviable amenities. Select from a variety of studio, one, two, and three-bedroom floor plan schemes designed with excellence in mind. Escape ordinary; indulge in an apartment

  1874 Harmon Ave, Winter Park, FL 32789
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  /2

  $890,000 Sold Jun 12, 2025

  1762 Mondrian Cir, Winter Park, FL 32789

  • 3 Beds
  • 3.5 Baths
  • 2,265 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Below List Price
  • $393/SF
  • 114 Days On Market

  Current Estimated Value $922,502

  Last Listing Agent Brian Teach COLDWELL BANKER REALTY

  1762 Mondrian Cir, Winter Park, FL 32789
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  /2

  Est $807,317 Not Listed For Sale

  1375 Suffolk Rd, Winter Park, FL 32789

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft
  • Built 1940

  1375 Suffolk Rd, Winter Park, FL 32789

  Last Sold Summary

  • 8% Above List Price
  • $292/SF
  • 30 Days On Market

  Last Sold Price $745,000

  Last Listing Agent Beth Hobart MAINFRAME REAL ESTATE
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  /66

  $2,395,000

  • 4 Beds
  • 5.5 Baths
  • 4,392 Sq Ft

  1760 Legion Dr, Winter Park, FL 32789

  Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

  Steven Looper CHARLES RUTENBERG REALTY ORLANDO

  1760 Legion Dr, Winter Park, FL 32789
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  /15

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Condo for Rent

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792

  Call to schedule your private showing of this well-maintained 2 bedroom, 2 bathroom condo located on the second floor in the desirable Parkview Village Subdivision.This bright and open floor plan features a spacious living room with vaulted ceilings, perfectly positioned at the front of the home and open to the kitchen. The kitchen has all new appliances with a corner window that is perfect for

  Jacqueline Ramos JML REALTY INVESTMENTS LLC

  2936 Antique Oaks Cir Unit 70, Winter Park, FL 32792
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  /2

  $440,000 Sold Jan 29, 2026

  1621 Puritan Ave, Winter Park, FL 32792

  • 4 Beds
  • 2 Baths
  • 1,765 Sq Ft
  • Built 1963

  Last Sold Summary

  • 12% Below List Price
  • $249/SF
  • 342 Days On Market

  Current Estimated Value $440,258

  Last Listing Agent Alejandro Colon PREFERRED REAL ESTATE BROKERS

  1621 Puritan Ave, Winter Park, FL 32792
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  /23

  Est $217,404 Not Listed For Sale

  2494 Timberline Dr, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  2494 Timberline Dr, Winter Park, FL 32792

  Last Sold Summary

  • 9% Below List Price
  • $182/SF
  • 11 Days On Market

  Last Sold Price $240,000

  Last Listing Agent Jeff Jones Mark Spain
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  /26

  $285,000 Open Sat 10AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,495 Sq Ft

  2401 Sun Valley Cir, Winter Park, FL 32792

  Welcome to this charming 2-bedroom, 2-bath condo with a versatile loft, perfectly situated just minutes from shopping and the vibrant downtown Winter Park area! This light-filled end unit offers an open floor plan with vaulted ceilings and skylights, creating a bright and airy feel throughout. You’ll appreciate the newer flooring, crown molding, and the comfortable, functional layout. Relax and

  Jamie Vanosdol EXP REALTY LLC

  2401 Sun Valley Cir, Winter Park, FL 32792
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  /44

  $1,129 - $3,411 per month

  Liv at Winter Park Apartment Homes

  Studio - 3 Beds

  4755 N Goldenrod Rd, Winter Park, FL 32792

  Welcome home to LIV at Winter Park, offering beautiful lakeside apartments for rent. Our Winter Park, Florida community offers your choice of studio, one-bedroom, two-bedroom, and three-bedroom apartment floor plans, with six distinct styles available. Experience the convenience of living just outside of the opportunities and excitement of Orlando, FL. Our spacious floor plans boast modern

  4755 N Goldenrod Rd, Winter Park, FL 32792
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  /2

  $1,088,000 Sold Jan 30, 2026

  1092 Wading Waters Cir, Winter Park, FL 32792

  • 4 Beds
  • 3 Baths
  • 3,057 Sq Ft
  • Built 2019

  Last Sold Summary

  • 9% Below List Price
  • $356/SF
  • 60 Days On Market

  Current Estimated Value $1,103,120

  Last Listing Agent Tara Haefner KELLER WILLIAMS HERITAGE REALTY

  1092 Wading Waters Cir, Winter Park, FL 32792
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  /2

  Est $344,225 Not Listed For Sale

  1880 Viburnum Ln, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Built 1961

  1880 Viburnum Ln, Winter Park, FL 32792

  Last Sold Summary

  • 3% Below List Price
  • $308/SF
  • 132 Days On Market

  Last Sold Price $355,000

  Last Listing Agent Jennifer Wemert WEMERT GROUP REALTY LLC
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  /54

  $424,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,083 Sq Ft

  1367 Tierra Cir, Winter Park, FL 32792

  Under contract-accepting backup offers. Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with

  Brian Bauer SOUTHERN LAND & HOMES

  1367 Tierra Cir, Winter Park, FL 32792
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  /39

  $3,300 per month

  • 2 Beds
  • 2 Baths
  • 1,209 Sq Ft
  • House for Rent

  870 Carver St Unit A, Winter Park, FL 32789

  Welcome to 870 Carver Street, a thoughtfully designed two-bedroom, two-bath residence in the core of Winter Park. Offering more than 1,200 square feet, the newly constructed home features vaulted ceilings with exposed rafters, warm wood finishes and industrial-inspired black metal ductwork that define its architectural character. The primary suite includes a floating wall closet system, a laundry

  Drew Henner PREMIER SOTHEBY'S INTL. REALTY

  870 Carver St Unit A, Winter Park, FL 32789
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  /2

  $420,000 Sold May 06, 2025

  627 Carvell Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,346 Sq Ft
  • Built 1957

  Last Sold Summary

  • 6% Below List Price
  • $312/SF
  • 152 Days On Market

  Current Estimated Value $407,552

  Last Listing Agent Ray Al-Malt EXP REALTY LLC

  627 Carvell Dr, Winter Park, FL 32792
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  /2

  Est $380,298 Not Listed For Sale

  3354 Hamlet Loop, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,533 Sq Ft
  • Built 1993

  3354 Hamlet Loop, Winter Park, FL 32792

  Last Sold Summary

  • 1% Below List Price
  • $251/SF
  • 17 Days On Market

  Last Sold Price $385,000

  Last Listing Agent Sherry Gao CHARLES RUTENBERG REALTY ORLANDO

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