Winter Park, FL Homes

• 

  

  

  /22

  $245,000

  $17K PRICE DROP Under Contract

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

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

  Under contract-accepting backup offers. DRASTIC PRICE REDUCTION!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

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

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

• 

  

  

  /20

  $1,750 Per Month

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft
  • Townhouse for Rent

  1720 Miller Ave, Winter Park, FL 32789

  Beautifully Updated 2 Bed / 1 Bath Duplex in Winter Park, FLStep into this freshly renovated 2-bedroom, 1-bath duplex offering a bright, modern living experience in one of Winter Park's most desirable neighborhoods. The home features new interior paint that gives every room a crisp, clean feel, paired with brand new flooring that adds warmth and style throughout the space. The living area is

  

  Bobby Keen

  KEEN REALTY GROUP, INC.

  1720 Miller Ave, Winter Park, FL 32789
• 

  

  /2

  $730,000

  Sold Sep 01, 2026

  950 S Kentucky Ave, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 2,155 Sq Ft
  • Built 1941

  Last Sold Summary

  • 9% Below List Price
  • $339/SF
  • 8 Days On Market

  Current Estimated Value $639,225

  Last Listing Agent Gwendolen Flynn COLDWELL BANKER REALTY

  950 S Kentucky Ave, Winter Park, FL 32789
• 

  

  /2

  Not Listed For Sale

  1964 Bering Ave, Winter Park, FL 32789

  1964 Bering Ave, Winter Park, FL 32789

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Clarence Fields FIELDS OF PROSPER LLC
• 

  

  

  /42

  $355,000

  $15K PRICE DROP Under Contract

  • 3 Beds
  • 2.5 Baths
  • 1,397 Sq Ft

  3374 Hamlet Loop, Winter Park, FL 32792

  Under contract-accepting backup offers. Tucked inside a quiet Winter Park neighborhood, this three-bedroom, two-bath home offers a comfortable layout and a sense of privacy that’s hard to find. No rear neighbors and a tree-lined backyard create a peaceful setting you’ll appreciate every day. The main living area is open and versatile, allowing you to arrange the space in a way that truly fits

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  3374 Hamlet Loop, Winter Park, FL 32792
• 

  /2

  Starting at $4,995 Per Month

  • 3 Beds

  770 Annesley Place, Winter Park, FL 32789

  Oxford at Winterpark

  

  770 Annesley Place, Winter Park, FL 32789
• 

  /2

  $217,000

  Sold Jun 22, 2026

  2400 Dominica Run, Winter Park, FL 32792

  • 2 Beds
  • 1 Bath
  • 854 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Below List Price
  • $254/SF
  • 48 Days On Market

  Current Estimated Value $216,304

  Last Listing Agent Laura Toppin FLORIDA HOME TEAM REALTY LLC

  2400 Dominica Run, Winter Park, FL 32792
• 

  /2

  Est $188,109

  Not Listed For Sale

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,018 Sq Ft
  • Built 1984

  2936 Antique Oaks Cir Unit 71, Winter Park, FL 32792

  Last Sold Summary

  • 165 Days On Market

  Last Listing Agent Dean D Nikolic PMI PROPERTY ALLIANCE
• 

  

  /37

  $835,000

  Open Sat 11AM - 3PM $10K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,589 Sq Ft

  1090 Wildmeadow Run, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buy-down that reduces the buyer's interest rate and monthly payment.**This luxurious Modern Style home epitomizes maintenance-free living, featuring a premium, state of the art solar system YOU OWN OUTRIGHT, nearly eliminating your cost of

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  1090 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /20

  $2,300 Per Month

  • 3 Beds
  • 2 Baths
  • 1,432 Sq Ft
  • House for Rent

  524 N Lakemont Ave, Winter Park, FL 32792

  Charming 3-Bedroom, 2-Bath Winter Park Bungalow. Welcome home to this charming 3-bedroom, 2-bathroom bungalow-style home in Winter Park, offering 1,432 square feet of comfortable living space on a spacious 8,239-square-foot lot. Built in 1956, this single-story home combines classic bungalow character with the everyday conveniences today's renters are looking for. The inviting layout provides

  

  Peter Dang

  ALLIANCE RENTAL HOMES

  524 N Lakemont Ave, Winter Park, FL 32792
• 

  /2

  $710,000

  Sold Jun 23, 2026

  1108 Fairway Dr, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,677 Sq Ft
  • Built 1978

  Last Sold Summary

  • 2% Below List Price
  • $423/SF
  • 82 Days On Market

  Current Estimated Value $705,334

  Last Listing Agent Rene Droz, III CHARLES RUTENBERG REALTY ORLANDO

  1108 Fairway Dr, Winter Park, FL 32792
• 

  /2

  Est $426,724

  Not Listed For Sale

  2949 Clever Ln, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Built 2023

  2949 Clever Ln, Winter Park, FL 32792

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Joseph Sipp KELLER WILLIAMS WINTER PARK
• 

  

  /36

  $199,000

  $31K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,578 Sq Ft

  7488 Whisperwood Dr Unit 28, Winter Park, FL 32792

  Rare Two-Story 2BR/2.5BA Condo with Two Private Suites in Winter Park.Highlights: Two-story floor plan condominium with a townhome-style layout, 2 spacious bedrooms, each with its own private ensuite bathroom, 2.5 bathrooms, Functional kitchen with stainless steel appliances, Open-concept living and dining area, Private fenced patio – perfect for relaxing, grilling, or entertaining,

  

  Miranda Azer

  PARKVIEW REAL ESTATE

  7488 Whisperwood Dr Unit 28, Winter Park, FL 32792
• 

  

  /81

  Starting at $1,815

  Total Monthly Price

  • 1 - 3 Beds

  7490 Dwell Well Way, Winter Park, FL 32792

  Dwell well with us. Welcome to quintessential Vintage Winter Park, a residential community featuring One, Two & Three bedroom apartments in Winter Park, FL. Spacious layouts and amenities welcome you home, along with exceptional service and an ideal location within walking distance to shopping, dining and entertainment options.

  Vintage Winter Park Apartments

  

  7490 Dwell Well Way, Winter Park, FL 32792
• 

  /2

  $290,000

  Sold Feb 06, 2026

  1920 Carrigan Ave, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,242 Sq Ft
  • Built 1954

  Last Sold Summary

  • 14% Below List Price
  • $233/SF
  • 141 Days On Market

  Current Estimated Value $292,664

  Last Listing Agent Virginia Bellhorn WATSON REALTY CORP

  1920 Carrigan Ave, Winter Park, FL 32792
• 

  /2

  Est $210,998

  Not Listed For Sale

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  • 3 Beds
  • 2.5 Baths
  • 1,151 Sq Ft
  • Built 1984

  3251 Oak Lake Place Unit 135, Winter Park, FL 32792

  Last Sold Summary

  • 131 Days On Market

  Last Listing Agent Nick Nesta, III NESTA REAL ESTATE CONSULTANTS
• 

  

  /81

  $3,600,000

  • 4 Beds
  • 5 Baths
  • 4,202 Sq Ft

  276 Detmar Dr, Winter Park, FL 32789

  Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light.The main level offers two bedrooms and three full bathrooms, including a

  

  Melanie Johnston

  CALL IT CLOSED INTL REALTY

  276 Detmar Dr, Winter Park, FL 32789
• 

  

  /13

  $2,100 Per Month

  • 2 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Townhouse for Rent

  2605 Galliano Cir, Winter Park, FL 32792

  A Townhome for our times. Renovated and Made Ready; this luxurious 2 bedroom/2.5 bath residence includes a private attached garage and has been redesigned for today's needs. Securely located in a private gated Winter Park Community. “Eating In” takes on a Whole Foods new meaning with a gourmet modern kitchen. Upstairs, the Master Suite includes ample storage and a luxurious, light-filled bath. A

  

  Eric Rollings

  MAINFRAME REAL ESTATE

  2605 Galliano Cir, Winter Park, FL 32792
• 

  /2

  $1,965,000

  Sold Jul 29, 2026

  2261 Mulbry Dr, Winter Park, FL 32789

  • 4 Beds
  • 3 Baths
  • 3,696 Sq Ft
  • Built 2020

  Last Sold Summary

  • 2% Below List Price
  • $532/SF
  • 28 Days On Market

  Current Estimated Value $1,868,808

  Last Listing Agent Jo-Ann Lamar PREMIER SOTHEBY'S INTL. REALTY

  2261 Mulbry Dr, Winter Park, FL 32789
• 

  /2

  Est $109,660

  Not Listed For Sale

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

  • 2 Beds
  • 2 Baths
  • 1,036 Sq Ft
  • Built 1974

  7429 Daniel Webster Dr Unit 13, Winter Park, FL 32792

  Last Sold Summary

  • 38 Days On Market

  Last Listing Agent Pedro Ramos ROCKER'S REAL ESTATE, LLC
• 

  

  /67

  $575,000

  • 2 Beds
  • 2.5 Baths
  • 1,648 Sq Ft

  1259 Indiana Ave, Winter Park, FL 32789

  Virtually Staged. WINTER PARK, WITHIN REACH. A rare opportunity to step into one of Central Florida’s most coveted lifestyles. Bright, airy, remarkably spacious, this immaculate 2-bedroom townhome lives far larger than its approximately 1,600 sq.ft.suggests. Greet the day with a sunny disposition as morning light fills the oversized, east-facing primary bedroom. Step onto the private lanai with a

  

  Karan Wienker

  COLDWELL BANKER REALTY

  1259 Indiana Ave, Winter Park, FL 32789
• 

  

  /49

  Starting at $1,267 Per Month

  • 1 - 3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Experience the perfect blend of comfort and convenience at Cranes Landing Apartments in Winter Park, Florida. Our beautifully designed one-, two-, and three-bedroom apartment homes feature open-concept layouts, modern finishes, and premium appliances to complement your lifestyle.Enjoy a community that’s built around connection and comfort. Relax by the resort-style pool, challenge friends

  Cranes Landing Apartments

  

  3440 N Goldenrod Rd, Winter Park, FL 32792
• 

  /2

  $955,000

  Sold Feb 24, 2026

  512 Clarendon Ave, Winter Park, FL 32789

  • 4 Beds
  • 3.5 Baths
  • 2,824 Sq Ft
  • Built 2001

  Last Sold Summary

  • 3% Below List Price
  • $338/SF
  • 21 Days On Market

  Current Estimated Value $954,693

  Last Listing Agent Sarah Tomlinson COMPASS FLORIDA LLC

  512 Clarendon Ave, Winter Park, FL 32789
• 

  /2

  Est $248,974

  Not Listed For Sale

  1250 S Denning Dr Unit 111, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 908 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 111, Winter Park, FL 32789

  Last Sold Summary

  • 76 Days On Market

  Last Listing Agent Alayna Phillips EXP REALTY LLC
• 

  

  /31

  $369,900

  $10K PRICE DROP Under Contract

  • 2 Beds
  • 1 Bath
  • 988 Sq Ft

  440 Cambridge Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**Welcome to 440 Cambridge Blvd in Winter Park, a charming 2-bedroom, 1-bath home featuring an open floorplan, an additional family room, and inviting indoor-outdoor spaces that

  

  Thomas Nickley

  KELLER WILLIAMS REALTY AT THE PARKS

  440 Cambridge Blvd, Winter Park, FL 32789
• 

  

  /36

  $2,750 Per Month

  • 3 Beds
  • 2 Baths
  • 1,302 Sq Ft
  • House for Rent

  1627 Orange Ave, Winter Park, FL 32789

  Charming 3-bedroom, 2-bath bungalow located in the highly desirable, well-established Orwin Manor neighborhood in the City of Winter Park. Ideally situated between Downtown Orlando and Park Avenue, this home is just minutes from AdventHealth Hospital, Rollins College, and offers convenient access to I-4.The spacious retreat is located just across the hall from a beautifully renovated

  

  Peter Dang

  ALLIANCE RENTAL HOMES

  1627 Orange Ave, Winter Park, FL 32789
• 

  /2

  $374,900

  Sold Oct 10, 2025

  2028 Leanne Ct, Winter Park, FL 32792

  • 3 Beds
  • 2 Baths
  • 1,539 Sq Ft
  • Built 1968

  Last Sold Summary

  • $244/SF
  • 9 Days On Market

  Last Listing Agent Jamie Ampel ALL SELLERS & BUYERS REALTY INC

  2028 Leanne Ct, Winter Park, FL 32792
• 

  /2

  Est $808,210

  Not Listed For Sale

  200 Carolina Ave Unit 201, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,305 Sq Ft
  • Built 1981

  200 Carolina Ave Unit 201, Winter Park, FL 32789

  Last Sold Summary

  • 0 Days On Market

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

  

  /35

  $350,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,268 Sq Ft

  7261 Abbey Ln, Winter Park, FL 32792

  Welcome home to this charming 3-bedroom, 2-bathroom residence offering comfort, functionality, and the freedom of NO HOA! This inviting home features a desirable split-bedroom floor plan, a spacious living area, and a 2-car garage. Enjoy Florida living year-round from the screened and covered patio overlooking a fully fenced backyard—perfect for entertaining, pets, or simply relaxing in your own

  

  Martha Grasty

  EXP REALTY LLC

  7261 Abbey Ln, Winter Park, FL 32792
• 

  

  /26

  Starting at $1,195 Per Month

  • 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

  Central Place At Winter Park

  

  7000 University Blvd, Winter Park, FL 32792
• 

  /2

  $1,200,000

  Sold May 29, 2026

  3711 Vinsetta Ct, Winter Park, FL 32792

  • 6 Beds
  • 4 Baths
  • 4,214 Sq Ft
  • Built 2015

  Last Sold Summary

  • 20% Below List Price
  • $285/SF
  • 75 Days On Market

  Current Estimated Value $1,185,569

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

  3711 Vinsetta Ct, Winter Park, FL 32792
• 

  /2

  Est $231,605

  Not Listed For Sale

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  • 2 Beds
  • 2 Baths
  • 1,026 Sq Ft
  • Built 1972

  1500 Gay Rd Unit 7A, Winter Park, FL 32789

  Last Sold Summary

  • 205 Days On Market

  Last Listing Agent Sean McCartney PRISTINE FLORIDA PROPERTIES LLC
• 

  

  /29

  $278,000

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

  2475 Tahoe Cir, Winter Park, FL 32792

  Turnkey Living in the Heart of Winter Park!Welcome to this beautifully maintained 2-bedroom, 2-bath townhome offering the perfect blend of comfort, convenience, and low-maintenance living. Vacant and move-in ready, this home has been freshly painted and features a recently replaced air conditioning system, providing peace of mind for its next owner.Inside, you'll find a thoughtfully

  

  Sarah Doyer

  COLDWELL BANKER REALTY

  2475 Tahoe Cir, Winter Park, FL 32792
• 

  

  /18

  $1,750 Per Month

  • 1 Bed
  • 1 Bath
  • 650 Sq Ft
  • Apartment for Rent

  Unlisted Address

  Gorgeous FULLY FURNISHED 1 Bedroom/1 Bath apartment with private entrance, in Winter Park. This attached apartment has been thoughtfully renovated with beautiful Luxury European Design. This apartment features a private courtyard and private entrance. Upon entering you will be greeted by a spacious living room fitted with a sofa chase, 55” Flat Screen Television, a small dining table/desk, modern

  

  Nicholas Wild

  GATE PROPERTIES & MANAGEMENT INC

  Unlisted Address
• 

  /2

  $449,000

  Sold Aug 12, 2026

  2611 Lotafun Ave, Winter Park, FL 32789

  • 3 Beds
  • 2 Baths
  • 1,838 Sq Ft
  • Built 1962

  Last Sold Summary

  • $244/SF
  • 3 Days On Market

  Current Estimated Value $482,926

  Last Listing Agent Kelly Price KELLY PRICE & COMPANY LLC

  2611 Lotafun Ave, Winter Park, FL 32789
• 

  /2

  Est $174,059

  Not Listed For Sale

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  • 1 Bed
  • 1 Bath
  • 658 Sq Ft
  • Built 1967

  1250 S Denning Dr Unit 108, Winter Park, FL 32789

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Cleve Loveland LOVELAND PROPERTIES
• 

  

  /15

  $164,500

  $11K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 732 Sq Ft

  1500 Gay Rd Unit 4D, Winter Park, FL 32789

  ANOTHER PRICE ADJUSTMENT! Lakefront Community! Enjoy Glorious Sunsets, Cocktails on the Deck and the Peace of Water and the Amazing Joy of Nature! All this near the heart of Winter Park and walking distance to all kinds of Shopping!One of few 1 Bedrooms and an Upstairs End Unit! Enjoy Spacious Room Sizes for easy Furniture Placement, Compact Kitchen, Bright Master Bedroom with additional

  Janice Erickson

  REALCOM REAL ESTATE SERVICES INC

  1500 Gay Rd Unit 4D, Winter Park, FL 32789
• 

  

  /131

  Starting at $1,475 Per Month

  • 1 - 3 Beds

  541 Oak Reserve Ln, Winter Park, FL 32792

  Welcome home to Oak Reserve at Winter Park Apartments, a quiet community where your needs and wishes are our priority. Covering all the bases for a comfortable living experience, our apartments in Winter Park, FL, are completed by lifestyle-oriented amenities, fantastic services, and a well-connected location within walking distance of Full Sail University. Short-term leases are available,

  Oak Reserve at Winter Park

  

  541 Oak Reserve Ln, Winter Park, FL 32792
• 

  /2

  $2,295,000

  Sold Dec 16, 2025

  1661 Palm Ave, Winter Park, FL 32789

  • 4 Beds
  • 6 Baths
  • 3,570 Sq Ft
  • Built 2025

  Last Sold Summary

  • 12% Below List Price
  • $643/SF
  • 26 Days On Market

  Current Estimated Value $2,188,495

  Last Listing Agent Nancy Bagby FANNIE HILLMAN & ASSOCIATES

  1661 Palm Ave, Winter Park, FL 32789
• 

  /2

  Est $1,119,479

  Not Listed For Sale

  100 S Virginia Ave Unit 319, Winter Park, FL 32789

  • 3 Beds
  • 3 Baths
  • 2,649 Sq Ft
  • Built 2008

  100 S Virginia Ave Unit 319, Winter Park, FL 32789

  Last Sold Summary

  • 2 Days On Market

  Last Listing Agent Padgett McCormick KELLY PRICE & COMPANY LLC

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