Winter Park, FL Homes

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  /59

  $1,575,000

  • 3 Beds
  • 2.5 Baths
  • 2,128 Sq Ft

  690 Osceola Ave Unit 604, Winter Park, FL 32789

  Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

  Larry Slung COLDWELL BANKER RESIDENTIAL RE

  690 Osceola Ave Unit 604, Winter Park, FL 32789
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  /36

  $1,216 - $3,210 per month

  Summerlin at Winter Park Apartments

  1-3 Beds

  3207 Rosebud Ln, Winter Park, FL 32792

  These apartments for rent in Orlando are close to Full Sail University and the University of Central Florida. Offering pet-friendly apartments one, two, and three-bedroom floorplans, Summerlin at Winter Park envelops residents in convenience and fun. With one of the largest pools in this area, you can beat the heat and relax and then take a visit to our 24-hour fitness center, billiards table, or

  3207 Rosebud Ln, Winter Park, FL 32792
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  /2

  $1,050,000 Sold Jul 14, 2025

  • 2,374 Sq Ft
  • $442/SF
  • 23 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2017

  795 W Canton Ave, Winter Park, FL 32789

  Welcome to your dream home in the heart of beautiful Winter Park, Florida! Just a short stroll to iconic Park Avenue and Winter Park Village, this stunning modern Craftsman by David Weekley Homes perfectly blends luxury, comfort, and convenience.The thoughtfully designed floor plan features a downstairs primary suite, rich hardwood flooring, and sliding barn doors opening to a versatile

  Margo Rochelle WEICHERT REALTORS HALLMARK PROPERTIES

  795 W Canton Ave, Winter Park, FL 32789
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  /42

  Est $686,002 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-21, Winter Park, FL 32789
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  /35

  $784,000

  • 5 Beds
  • 4 Baths
  • 2,866 Sq Ft

  5618 Winterbrook Way, Winter Park, FL 32792

  This stunning 5-bed, 4-bath home in the exclusive gated WINTERBROOK community is move in ready and ready for you to enjoy. Built in 2020 by Pulte Homes, this like new energy-efficient home offers luxury wood-look tile, wood beams, a 2 car garage with epoxy floors and a beautifully landscaped backyard. The gourmet kitchen features quartzite countertops, a gas cooktop, upgraded sink, and large

  Elizabeth Binder REDFIN CORPORATION

  5618 Winterbrook Way, Winter Park, FL 32792
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  /13

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,286 Sq Ft
  • House for Rent

  689 Overspin Dr, Winter Park, FL 32789

  Welcome to 689 Overspin Rd – a beautifully maintained 2-bedroom, 2-bathroom home in the heart of Winter Park! This inviting residence features stunning hardwood floors throughout, creating a warm and stylish ambiance from the moment you walk in. Enjoy cooking and entertaining in the large open kitchen, complete with stainless steel appliances, ample counter space, and plenty of storage. Cozy up

  Megan Teal MAINFRAME REAL ESTATE

  689 Overspin Dr, Winter Park, FL 32789
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  /2

  $2,435,000 Sold Jul 14, 2025

  • 3,852 Sq Ft
  • $632/SF
  • 31 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2019

  1795 Greenwich Ave, Winter Park, FL 32789

  Welcome to a one-of-a-kind, custom-designed residence offering the perfect blend of modern sophistication, thoughtful functionality, and resort-style amenities. Designed by Origins Residential Design and meticulously constructed by Native Homes, this 5-bedroom, 5.5-bathroom showplace is located in one of Winter Park’s most sought-after neighborhoods—just minutes from Park Avenue, Baldwin Park,

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1795 Greenwich Ave, Winter Park, FL 32789
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  /20

  Est $267,652 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 968 Sq Ft

  5498 Peaco Place, Winter Park, FL 32792

  5498 Peaco Place, Winter Park, FL 32792
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  /28

  $649,900

  • 2 Beds
  • 2 Baths
  • 1,000 Sq Ft

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789

  Rare opportunity to own a first floor unit with soaring 9 foot ceilings only steps away from the prestegious Park Avenue! Discover the perfect blend of luxury, comfort, and convenience with this immaculate, move-in-ready condo, in the heart of Winter Park. Recently transformed with meticulous attention to detail, this lock-and-leave gem boasts an elegant, high-end renovation that exudes

  Jonathan Ruiz KELLER WILLIAMS WINTER PARK

  535 N Interlachen Ave Unit 106, Winter Park, FL 32789
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  /50

  $1,150 - $2,848 per month

  Sovereignty at Winter Park Apartments

  1-2 Beds

  7745 Brandywood Cir, Winter Park, FL 32792

  We offer 1 and 2 bedroom apartment homes with fully equipped kitchens, garden tubs, vaulted ceilings, ornamental chair rails, and so much more. Our community has a designer clubhouse, state-of-the-art fitness center, a sparkling pool, planned social activities, a high-speed internet business center, and 24 hour emergency maintenance. Winter Park location convenient to Full Sail, UCF, Valencia,

  7745 Brandywood Cir, Winter Park, FL 32792
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  /2

  $705,000 Sold Jul 14, 2025

  • 2,385 Sq Ft
  • $296/SF
  • 57 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1979

  1139 Fairway Dr, Winter Park, FL 32792

  NEW LOWER PRICE 6/3/25, OWNER WANTS OFFERS. NO HOA. Fabulous RENOVATED home in the heart of Winter Park, where timeless charm meets tranquil Winter Park Pines golf course living. Nestled on a lush, manicured lot right on the 9th fairway, this expansive REMODELLED OPEN AND AIRY SPLIT-plan residence offers a SPLIT PLAN WITH 4 generously sized bedrooms, 2 full baths, and FABULOUS FLEX SPACE that

  Gale Milgrim KELLER WILLIAMS WINTER PARK

  1139 Fairway Dr, Winter Park, FL 32792
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  /30

  Est $746,963 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789

  311 E Morse Blvd Unit 4-4, Winter Park, FL 32789
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  /20

  $265,000

  • 2 Beds
  • 2.5 Baths
  • 1,295 Sq Ft

  2394 Sun Valley Cir, Winter Park, FL 32792

  This charming 2-bedroom, 2-bathroom condo offers 1,295 square feet of comfortable single-level living, thoughtfully designed for easy living and entertaining. The open floor plan boasts a spacious, sunlit living area and a well-appointed kitchen, perfect for culinary creations. Both bedrooms are generously sized and provide privacy, each featuring its own en-suite bathroom for added convenience.

  Jamie Vanosdol EXP REALTY LLC

  2394 Sun Valley Cir, Winter Park, FL 32792
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  /19

  $3,100 per month

  • 3 Beds
  • 2.5 Baths
  • 1,645 Sq Ft
  • Townhouse for Rent

  1253 Indiana Ave, Winter Park, FL 32789

  Lovely townhouse in upscale Winter Park. All bedrooms upstairs. Great screened patio that connects to the garage. Walking distance to amazing restaurants and close to Downtown Winter Park and shopping.

  Lidya Gongage SPRING REALTY ORLANDO

  1253 Indiana Ave, Winter Park, FL 32789
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  /2

  $1,942,000 Sold Jul 14, 2025

  • 3,907 Sq Ft
  • $497/SF
  • 50 Days On Market

  • 5 Beds
  • 5 Baths
  • Built 1961

  1394 Stewart St, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Five-bedroom, 3900+ sq ft pool home with 3 car garage on a large corner lot in the sought -after Park Grove neighborhood near Lake Maitland and Park Avenue. Great Room consists of a Family Room area with a wood-burning fireplace and tray ceilings and a Sun Room area with bay windows and french doors overlooking the pool deck. Kitchen

  Richard Vaughn REALTY ONE GROUP INSPIRATION

  1394 Stewart St, Winter Park, FL 32789
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  /63

  Est $3,617,953 Not Listed For Sale

  • 3 Beds
  • 5 Baths
  • 4,237 Sq Ft

  637 N Park Ave, Winter Park, FL 32789

  637 N Park Ave, Winter Park, FL 32789
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  /24

  $135,000

  • 2 Beds
  • 1.5 Baths
  • 1,085 Sq Ft

  126 Scottsdale Square Unit B126, Winter Park, FL 32792

  Great location!! Discover the charm of this beautifully maintained condo at 126 Scottsdale Square, nestled in a serene and convenient Orlando community. This condo boasts 3 bedrooms and 2 bathrooms thoughtfully designed with a spacious layout perfect for comfortable living. From the bright and open living area to the modern kitchen with upgraded appliances. Every detail has been tailored for

  Thomas Hicks, Sr LPT REALTY, LLC

  126 Scottsdale Square Unit B126, Winter Park, FL 32792
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  /42

  $1,482 - $2,124 per month

  Westmount at Winter Park

  Studio-3 Beds

  1701 Lee Rd, Winter Park, FL 32789

  Westmount at Winter Park has everything you desire and more in prestigious Winter Park. Enjoy access to I-4, shopping and the best restaurants around!

  1701 Lee Rd, Winter Park, FL 32789
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  /2

  $5,400,000 Sold Jul 14, 2025

  • 4,725 Sq Ft
  • $1143/SF
  • 152 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2008

  541 Virginia Dr, Winter Park, FL 32789

  *Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home.Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers

  Keith Moore HOMEVEST REALTY

  541 Virginia Dr, Winter Park, FL 32789
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  /37

  Est $831,225 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 3,044 Sq Ft

  1361 Heavenly Cove, Winter Park, FL 32792

  1361 Heavenly Cove, Winter Park, FL 32792
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  /31

  $1,490,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 2,838 Sq Ft

  2408 Lafayette Ave, Winter Park, FL 32789

  This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

  Matthew Burks CORCORAN PREMIER REALTY

  2408 Lafayette Ave, Winter Park, FL 32789
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  /25

  $1,895 per month

  • 2 Beds
  • 2.5 Baths
  • 1,130 Sq Ft
  • Townhouse for Rent

  152 Sandlewood Trail Unit 6, Winter Park, FL 32789

  Lovely, light and airy home with newer appliances, fresh paint throughout. This end unit townhome has a spacious kitchen with eat-in space, a large bay window that floods the room with natural light. The large living and dining room features a corner fireplace. It also has tile flooring and oversized sliders that open to a private back patio...the pool is a short walk across the yard. There is a

  Jackie O'Leary FANNIE HILLMAN & ASSOCIATES

  152 Sandlewood Trail Unit 6, Winter Park, FL 32789
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  /2

  $385,000 Sold Jul 12, 2025

  • 1,000 Sq Ft
  • $385/SF
  • 355 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1960

  151 N Orlando Ave Unit 131, Winter Park, FL 32789

  FULL LAKE FRONT VIEW, ONE OUT OF 6 UNITS WITH BEST VIEW IN LAKE KILLARNEY CONDO! Amazing location in Winter Park! Full LAKEFRONT view, fully renovated end unit condo on spring fed, navigable, & private Lake Killarney. Sunset views every evening from your living, kitchen, dining, and master bedroom! . Lakefront pool and private boat dock with ~14 slips (see management for availability).

  Adriana Montes MBA ? FLORIDA DREAMS REALTY GRP INC

  151 N Orlando Ave Unit 131, Winter Park, FL 32789
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  /30

  Est $1,440,169 Not Listed For Sale

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

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789

  345 W Welbourne Ave Unit 104, Winter Park, FL 32789
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  /77

  $2,900,000 Pending

  • 4 Beds
  • 7 Baths
  • 5,416 Sq Ft

  1401 Green Cove Rd, Winter Park, FL 32789

  Under contract-accepting backup offers. This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was

  Terry Yonker BUCKEYE REALTY LLC

  1401 Green Cove Rd, Winter Park, FL 32789
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  /26

  $1,390 - $2,090 per month

  Central Place At Winter Park

  1-3 Beds

  7000 University Blvd, Winter Park, FL 32792

  Central Place at Winter Park, where contemporary living meets convenience in a vibrant locale in Winter Park, FL. Our one, two, and three-bedroom apartment community offers a prime location on University Blvd. near Full Sail University and just moments away from the charming downtown Winter Park area. Experience the essence of modern living in our thoughtfully designed residences, featuring

  7000 University Blvd, Winter Park, FL 32792
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  /2

  $420,000 Sold Jul 11, 2025

  • 1,140 Sq Ft
  • $368/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1961

  2809 Sanbina St, Winter Park, FL 32789

  Beautifully Updated 3 Bedroom, 2 Bath Pool Home in Desirable Winter Park! Welcome to your dream home! This spacious one story gem features 3 bedrooms, 2 full baths, and a private POOL, perfect for enjoying Florida living year round. Step inside to find brand NEW LUXURY VINYL PLANK flooring and FRESH INTERIOR PAINT throughout, giving the home a modern and move-in ready feel. The open layout offers

  Harry Kazarian STRONG FOUNDATION REALTY LLC

  2809 Sanbina St, Winter Park, FL 32789
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  /36

  Est $213,438 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792

  2935 Antique Oaks Cir Unit 62, Winter Park, FL 32792
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  /25

  $349,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,349 Sq Ft

  657 Overspin Dr, Winter Park, FL 32789

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **Seller is motivated and encourages all serious offers—bring your buyers!** Welcome to your cozy Winter Park retreat! This charming 4-bedroom, 2-bath home blends comfort and convenience in one perfect package. Nestled on a spacious lot with a large backyard—ideal for entertaining, gardening, or playing

  Abby Nelson RE/MAX 200 REALTY

  657 Overspin Dr, Winter Park, FL 32789
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  /22

  $2,250 per month

  • 3 Beds
  • 1 Bath
  • 1,136 Sq Ft
  • Property for Rent

  7034 Easter St, Winter Park, FL 32792

  Location!! This completely renovated home is now available for rent and can be yours! With 3 bedrooms and 1 bathroom, this home is located in the highly desirable city of Winter Park. It features a LARGE, PRIVATE, HOA-FREE LOT, PARKING FOR SEVERAL CARS AND TRUCKS, AND A FULLY ENCLOSED FRONT AND BACK YARD, giving you complete privacy. NEW LAMINATE FLOORS, NEW BATHROOM, NEW APPLIANCES, NEW KITCHEN

  Adriana Elizundia ELIZUNDIA LUXURY REALTY LLC

  7034 Easter St, Winter Park, FL 32792
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  /2

  $472,500 Sold Jul 11, 2025

  • 1,611 Sq Ft
  • $293/SF
  • 21 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1980

  1921 Heathwood Dr, Winter Park, FL 32792

  Fully Renovated 4-Bedroom Home in Prime Winter Park Location – No HOA!Welcome to this beautifully updated block home in one of Winter Park's most desirable neighborhoods—offering modern upgrades, a spacious layout, and no HOA restrictions! Recently appraised at $518,000—appraisal is attached in the MLS for buyer confidence.This move-in-ready home features 4 full bedrooms and 3.5

  Austin Cummings NEXTDWELL

  1921 Heathwood Dr, Winter Park, FL 32792
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  /39

  Est $244,121 Not Listed For Sale

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

  220 Lewfield Cir, Winter Park, FL 32792

  220 Lewfield Cir, Winter Park, FL 32792
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  /43

  $1,199,000 Pending

  • 4 Beds
  • 5 Baths
  • 4,015 Sq Ft

  4052 Gilder Rose Place, Winter Park, FL 32792

  A rare opportunity to own this beautiful pool home in Winter Park at Bear Gully Pointe, a gated community located on a spring fed 137-acre Lake. This perfect 3-way split floor plan with pool views has an open fireplace to enjoy the mornings & evenings. The conservation area in back makes a very private pool & patio area. Expect to be impressed when entering the home with expansive ceilings, open

  Steve Lang HOMEVEST REALTY

  4052 Gilder Rose Place, Winter Park, FL 32792
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  /31

  $1,320 - $2,522 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

  $618,900 Sold Jul 11, 2025

  • 1,762 Sq Ft
  • $351/SF
  • 65 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  624 Dunraven Dr, Winter Park, FL 32792

  Welcome to this beautifully updated 3-bedroom, 2-bath home with a 2-car garage, nestled in the sought-after Kenilworth Shores neighborhood of Winter Park. Featuring an open-concept layout, the home is anchored by a modern kitchen with an island, stainless steel appliances, granite countertops, and stylishly renovated bathrooms. Enjoy cozy evenings by the fireplace or relax in the spacious,

  Brian Rotenberger COMPASS FLORIDA LLC

  624 Dunraven Dr, Winter Park, FL 32792
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  /18

  Est $160,773 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 749 Sq Ft

  2929 Antique Oaks Cir Unit 49, Winter Park, FL 32792

  2929 Antique Oaks Cir Unit 49, Winter Park, FL 32792
• 

  

  /29

  $405,000 Pending

  • 4 Beds
  • 2 Baths
  • 1,598 Sq Ft

  5600 Revelwood Loop, Winter Park, FL 32792

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. PRICE IMPROVEMENT!!!! Clean, BRIGHT and MOVE IN READY!!! Prepare to be IMPRESSED with this BEAUTIFUL 4 bedroom, 2 Bath 1598 Sq Ft home in the quaint and quiet Bridgewater Community! This terrific Winter Park home is LIGHT-FILLED, SPACIOUS and has a terrific 3 way split floorplan. Upon entering the home, you

  Tami Vincent REAL ESTATE PROS

  5600 Revelwood Loop, Winter Park, FL 32792
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  /23

  $2,995 per month

  • 4 Beds
  • 2 Baths
  • 2,234 Sq Ft
  • House for Rent

  3300 Bennington Ct, Winter Park, FL 32792

  Winter Park Rental Home in Bennington Estates. Home offers 4 Bedrooms, 2 Baths, Split plan, Large Eat-in Kitchen w/Island, 2 Car Garage, 2234 Sqft under air, Tile & Laminate Wood flooring throughout home, Formal Dining Room & Formal Living Room with Bay Window. Enclosed Rear Patio that can be cooled, Large Backyard. The formal living area makes a great Den or Office space. Location offers

  Emily Lemieux RE/MAX TOWN & COUNTRY REALTY

  3300 Bennington Ct, Winter Park, FL 32792
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  /2

  $440,000 Sold Jul 10, 2025

  • 1,806 Sq Ft
  • $244/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  2312 Poinciana Rd, Winter Park, FL 32792

  This charming single-story home offers a comfortable and versatile layout with 3 bedrooms and 2 bathrooms, perfect for families or those looking to spread out and relax. A bright and sunny kitchen flows into the cozy family room, making daily living easy and enjoyable. Just off the kitchen, the generous dining and living areas provide ample space for entertaining or unwinding at the end of the

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  2312 Poinciana Rd, Winter Park, FL 32792
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  /21

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

  7340 Daniel Webster Dr Unit A, Winter Park, FL 32792

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