Winter Park, FL Homes

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  /29

  $395,000

  • 4 Beds
  • 2 Baths
  • 1,568 Sq Ft

  2827 Euston Rd, Winter Park, FL 32789

  Welcome to 2827 Euston Rd, a beautifully updated home in the highly desirable Winter Park area with the added bonus of no HOA! This charming residence offers 3 beds, 2baths, and a versatile bonus room that can be used as an office, playroom, or additional living space.The master suite is thoughtfully separated from the other two bedrooms, providing privacy and convenience. Inside, you’ll

  

  Evelyn Tejada

  REGENCY REAL ESTATE LLC

  (321) 461-5735

  2827 Euston Rd, Winter Park, FL 32789
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  /24

  $2,350 per month

  • 2 Beds
  • 1 Bath
  • 1,260 Sq Ft
  • House for Rent

  206 Tyree Ln, Winter Park, FL 32792

  Modern midcentury for lease! Enjoy location and lifestyle in this professionally managed property. You will love this recently renovated, one-story, two-bedroom and one-bath home situated on a large fenced-in lot with a pool. Tile and wood laminate floors throughout! This well-designed home offers plenty of communal living spaces with a formal living area at the front of the house, large windows

  Bruce Kalin

  JC FLORIDA REALTY LLC

  (321) 467-7673

  206 Tyree Ln, Winter Park, FL 32792
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  /2

  $8,900,000 Sold May 02, 2025

  • 8,583 Sq Ft
  • $1037/SF
  • 1 Day On Market

  • 8 Beds
  • 8.5 Baths
  • Built 1995

  2001 Bett Mar Ln, Winter Park, FL 32789

  Discover an extraordinary lifestyle at this one-of-a-kind estate, elegantly situated on the shores of Lake Maitland in the distinguished Winter Park area. This remarkable property is unlike any other in the market, seamlessly blending sophisticated Mediterranean and Spanish architectural elements to create a serene and inviting retreat. Upon entering through the stately steel gates, you are

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  2001 Bett Mar Ln, Winter Park, FL 32789
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  /42

  Est $1,673,308 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,052 Sq Ft

  1805 Harland Park Dr, Winter Park, FL 32789

  1805 Harland Park Dr, Winter Park, FL 32789
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  /53

  $1,795,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,444 Sq Ft

  2813 Northwood Blvd, Winter Park, FL 32789

  Under contract-accepting backup offers. Modern living in Central Florida’s desirable Winter Park, this residence offers an elegant balance of refined design, elevated finishes and seamless indoor-outdoor living. Completed in 2021 and impeccably maintained, this two-story home features four generously sized bedrooms, a sun-filled private office, three-and-a-half baths, and an oversized two-car

  

  Candace Cassidy

  PREMIER SOTHEBY'S INTL. REALTY

  (321) 342-2584

  2813 Northwood Blvd, Winter Park, FL 32789
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  /110

  $1,350 - $2,075 per month

  Oak Reserve at Winter Park

  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,

  541 Oak Reserve Ln, Winter Park, FL 32792
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  /2

  $2,300,000 Sold May 02, 2025

  • 3,089 Sq Ft
  • $745/SF
  • 7 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  2814 Parkland Dr, Winter Park, FL 32789

  PRESENTING THE NEWEST WINTER PARK RESIDENCE BUILT BY M. LAHR HOMES! Just completed, this stunning custom level home has come together perfectly with design and finish features that have to be seen in person to be truly appreciated. The combination of a fantastic floor plan that integrates perfectly with the expansive covered outdoor patio/pool/spa/outdoor space makes this house feel nothing less

  Robert Kurzreiter PA KELLER WILLIAMS REALTY AT THE PARKS

  2814 Parkland Dr, Winter Park, FL 32789
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  /26

  Est $467,217 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,308 Sq Ft

  2469 Firstlight Way, Winter Park, FL 32792

  2469 Firstlight Way, Winter Park, FL 32792
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  /53

  $799,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,503 Sq Ft

  2804 Dike Rd, Winter Park, FL 32792

  Welcome to your very own private personal retreat! This truly one of a kind oasis of a property features 1.9 acres of lushly landscaped garden in Winter Park. A four-bedroom, three-bathroom main house with a two-car attached garage and a luxurious pool. With paid-for solar panels and a 37 seer Geo-Thermal HVAC means you will enjoy significant savings on your power bills. The additional detached

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 461-3595

  2804 Dike Rd, Winter Park, FL 32792
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  /25

  $3,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,312 Sq Ft
  • Townhouse for Rent

  2249 Shadowland Loop, Winter Park, FL 32792

  Available August 1st, 2025. Welcome to 2249 Shadowland Loop, a premium end-unit townhouse in the gated, resort-style community of Enclave at Hawks Crest in Winter Park. Designed for discerning professionals seeking both style and convenience. Designed for discerning professionals seeking both style and convenience, this stunning 3-bedroom, 2.5-bath home offers refined living in one of Central

  Tara Garkowski KELLER WILLIAMS ADVANTAGE REALTY

  2249 Shadowland Loop, Winter Park, FL 32792
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  /2

  $535,000 Sold May 02, 2025

  • 1,522 Sq Ft
  • $352/SF
  • 1 Day On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  2012 Loch Berry Rd, Winter Park, FL 32792

  This home has three intriguing possibilities, each offering its unique set of considerations. There may be a buyer who decides to purchase the home to live in it as-is. This buyer envisions making gradual repairs and upgrades over time, personalizing the property while steadily investing in improvements. There may be an investor who plans to convert the property into a rental. This investor

  Al Sines PREMIER SOTHEBY'S INTL. REALTY

  2012 Loch Berry Rd, Winter Park, FL 32792
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  /47

  Est $1,176,324 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,575 Sq Ft

  1939 Woodcrest Dr, Winter Park, FL 32792

  1939 Woodcrest Dr, Winter Park, FL 32792
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  /42

  $895,000

  • 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 luxurious Modern Style home delivers the pinnacle lifestyle, in every aspect of MAINTENANCE FREE LIVING. You will enjoy premium views of nature with a RESORT CLUBHOUSE featuring an abundance of amenities including a resort pool, fitness center & playground, all JUST 250 FEET AWAY....This home has been IMPECCABLY MAINTAINED, and includes the

  

  Rod Chevalier

  BHHS FLORIDA REALTY

  (321) 339-2639

  1090 Wildmeadow Run, Winter Park, FL 32792
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  /42

  $1,912 - $5,037 per month

  Vintage Winter Park Apartments

  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.

  7490 Dwell Well Way, Winter Park, FL 32792
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  /2

  $490,000 Sold May 02, 2025

  • 1,050 Sq Ft
  • $467/SF
  • 6 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1959

  2463 Brookshire Ave, Winter Park, FL 32792

  Great house in sought after neighborhood. The home is close to Brookshire Elementary, Winter Park High, Cady Way trail, Cady Way pool, and Showalter Home has an inviting front porch with swing, storm door with decorative front door, open floor concept for family room, dining room and kitchen. The screened in back porch overlooks a nice fenced in yard. This home won't last long.

  Tom Kimbrough HOME WISE REALTY GROUP, INC.

  2463 Brookshire Ave, Winter Park, FL 32792
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  /2

  Est $464,555 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,598 Sq Ft

  1761 Indiana Ave Unit F, Winter Park, FL 32789

  1761 Indiana Ave Unit F, Winter Park, FL 32789
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  /44

  $748,000

  • 4 Beds
  • 2.5 Baths
  • 2,046 Sq Ft

  607 Dunblane Dr, Winter Park, FL 32792

  Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park, just minutes from Park Avenue’s top dining and shopping. Thoughtfully updated from top to bottom, this move-in-ready home features a brand-new AC system, luxury vinyl plank flooring throughout, and a stunning chef’s kitchen with quartz waterfall countertops, custom cabinetry, and all-new stainless steel

  

  Khozaif Merali

  CHARLES RUTENBERG REALTY ORLANDO

  (321) 490-4706

  607 Dunblane Dr, Winter Park, FL 32792
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  /38

  $2,100 per month

  • 2 Beds
  • 2 Baths
  • 1,119 Sq Ft
  • Condo for Rent

  200 Saint Andrews Blvd Unit 3503, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Are you looking for the perfect rental property inside the city limits of Winter Park? Look at the photos and judge for yourself. The owner has updated everything in this condo. It features two bedrooms and two full bathrooms, includes granite countertops and stainless steel appliances, recess lighting

  Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

  200 Saint Andrews Blvd Unit 3503, Winter Park, FL 32792
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  /2

  $640,000 Sold May 02, 2025

  • 1,881 Sq Ft
  • $340/SF
  • 19 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2023

  2739 Riddle Dr, Winter Park, FL 32789

  Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances.$64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on

  JASON OLD BRAINARD REALTY

  2739 Riddle Dr, Winter Park, FL 32789
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  /39

  Est $695,146 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,488 Sq Ft

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789

  311 E Morse Blvd Unit 6-1, Winter Park, FL 32789
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  /27

  $107,000

  • 2 Beds
  • 2 Baths
  • 1,066 Sq Ft

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792

  SELLER WILL GIVE A $5,000 CREDIT TOWARDS CLOSING COSTS!! Unlock the potential of this two-bedroom, two-bathroom condominium located in the Colonies community. This unit is has stainless steel appliances and granite countertops in both the kitchen and bathrooms. Each bedroom features spacious walk-in closets. A new A/C unit was just installed! The community has desirable amenities including a

  

  Barrett Spray

  KELLER WILLIAMS ADVANTAGE REALTY

  (321) 399-2572

  3057 Aaron Burr Ave Unit 2, Winter Park, FL 32792
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  /24

  $1,419 - $1,649 per month

  Indigo Winter Park

  1 Bed

  220 S Semoran Blvd, Winter Park, FL 32792

  Indigo Winter Park is a lavishly landscaped apartment home community. Each of our one bedroom, one bathroom apartments feature laminate flooring, carpeted bedrooms, washers & dryers, walk in closets, screened in patios, maple wood cabinetry, gas stoves and efficient appliances. Our pet-friendly apartment community includes three resort style pools, bbq grilling stations, two double tennis courts,

  220 S Semoran Blvd, Winter Park, FL 32792
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  /2

  $169,900 Sold May 02, 2025

  • 759 Sq Ft
  • $224/SF
  • 57 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1981

  631 Grenadine Ct Unit 631, Winter Park, FL 32792

  Discover the perfect blend of comfort and convenience in this charming 1-bedroom, 1-bathroom condo, nestled in the heart of Winter Park. End unit and perfect for investment or first time home owner! This beautifully updated home boasts a private fenced-in courtyard overlooking a serene conservation reserve, offering a peaceful retreat right outside your door. Inside, the open and airy layout

  Travis Lewis GECKO REALTY, INC

  631 Grenadine Ct Unit 631, Winter Park, FL 32792
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  /43

  Est $1,937,002 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,660 Sq Ft

  1809 Harland Park Dr, Winter Park, FL 32789

  1809 Harland Park Dr, Winter Park, FL 32789
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  /69

  $425,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,485 Sq Ft

  328 Lake Fair Ln, Winter Park, FL 32789

  Under contract-accepting backup offers. Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors,

  

  Tom Langmann

  RE/MAX 200 REALTY

  (321) 286-7286

  328 Lake Fair Ln, Winter Park, FL 32789
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  /35

  $6,500 per month

  • 5 Beds
  • 4 Baths
  • 2,743 Sq Ft
  • House for Rent

  1879 Sunset Dr, Winter Park, FL 32789

  Don’t miss this rare chance to live on the picturesque brick streets of Olde Winter Park—just minutes from Park Avenue’s premier shopping and dining.This beautifully updated 5-bedroom, 3-bath home features a spacious downstairs primary suite with stunning hardwood floors and soaring vaulted ceilings. A flexible main-level office or guest room adds versatility to the layout. The renovated kitchen

  Alison Ashby CORCORAN PREMIER REALTY

  1879 Sunset Dr, Winter Park, FL 32789
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  /2

  $380,000 Sold May 02, 2025

  • 1,428 Sq Ft
  • $266/SF
  • 42 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789

  Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning

  Dora Siler FOLIO REALTY LLC

  350 Killarney Bay Ct Unit 5, Winter Park, FL 32789
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  /51

  Est $1,491,951 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,922 Sq Ft

  1347 Chapman Cir, Winter Park, FL 32789

  1347 Chapman Cir, Winter Park, FL 32789
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  /53

  $2,849,000

  • 5 Beds
  • 5.5 Baths
  • 3,967 Sq Ft

  1690 Palm Ave, Winter Park, FL 32789

  This Fabulous transitional 5 bedroom pool home is perfect for family living & entertaining & just minutes from downtown Winter Park's shopping, entertainment & dining on Park Avenue. Floor plan is ideal w/ 2 bedroom suites downstairs plus office/flex space. Meticulously constructed by Austin Homes, modern & traditional elements blend together w/ its open layout & clean lines. Main floor features

  

  Daniel Robinson

  HOUWZER INC

  (321) 850-5975

  1690 Palm Ave, Winter Park, FL 32789
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  /40

  $1,362 - $1,982 per month

  Seabrook

  1-2 Beds

  3114 Terry Brook Dr, Winter Park, FL 32792

  The Seabrook Apartment community is located near the 408 Expressway, close to shopping and dining areas 1/4 mile away, just minutes away from the downtown areas of Orlando and Winter Park. Several renowned schools such as Brookshire Elementary, Glenridge Middle School and Winter Park High School are nearby as well. We offer spacious one and two-bedroom apartments. All of our homes have been

  3114 Terry Brook Dr, Winter Park, FL 32792
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  /2

  $385,000 Sold May 02, 2025

  • 1,536 Sq Ft
  • $251/SF
  • 171 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789

  Largest unit at Killarney Bay, set up as a town home -bedrooms upstairs town house with large screened in area back porch, new washer and dryer - wood floors throughout, close to Winter Park Village - complex is a small great location with great access to I-4 - Killarney Bay sits on Lake Killarney with private pool overlooking. Only 5 rental units are allowed at KB at any given time. Super clean

  Michael O'Shaughnessy MICHAEL O'SHAUGHNESSY, INC.

  740 #3 Killarney Bay Ct Unit 7-3, Winter Park, FL 32789
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  /13

  Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  700 Melrose Ave Unit M, Winter Park, FL 32789

  700 Melrose Ave Unit M, Winter Park, FL 32789
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  /38

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,562 Sq Ft

  1604 Nottingham Dr, Winter Park, FL 32792

  Seize this exceptional opportunity to acquire a remarkable property in the esteemed town of Winter Park. The roof is only four years old, with rain gutters around the entire house! The kitchen is update featuring a stone countertop, breakfast bar, and ample natural lighting. The GE refrigerator and stove top are 4yrs old. The professionally maintained oversized swimming pool adds to the

  

  Keegan Siegfried

  LPT REALTY, LLC

  (321) 621-7951

  1604 Nottingham Dr, Winter Park, FL 32792
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  /17

  $2,545 per month

  • 3 Beds
  • 2.5 Baths
  • 1,787 Sq Ft
  • Townhouse for Rent

  7628 Aloma Pines Ct, Winter Park, FL 32792

  This 3 bedroom, 2.5 bathroom townhouse is located in the gated community of Aloma Trails near downtown Winter Park and local shops, restaurants, and schools. Features include an open floor plan with tile flooring throughout the downstairs main living area. The upgraded kitchen features 42" cabinets, granite counter tops, stainless steel appliances, tiled back splash, an island, and walk-in

  Matthew Kirsch REAL PROPERTY MANAGEMENT AND REALTY

  7628 Aloma Pines Ct, Winter Park, FL 32792
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  /2

  $188,000 Sold May 02, 2025

  • 840 Sq Ft
  • $224/SF
  • 202 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1990

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792

  WINTER PARK CONDO! This spacious condo is located just minutes from UCF, Rollins College and Full Sail University, walking distance to shopping center and conveniently located near restaurants, major roads and highways (417 & 408). Completely renovated and ready to move into 2 bed 2 bath has NO CARPET, NEW KITCHEN CABNIETS with STAINLESS STEEL APPLIANCES, NEW VANITIES in bathrooms, BRAND NEW AC

  Melissa Wilson KELLER WILLIAMS REALTY AT THE LAKES

  3651 N Goldenrod Rd Unit 204, Winter Park, FL 32792
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  /12

  Not Listed For Sale

  • 4 Beds
  • 2,291 Sq Ft

  2506 Argyll Cove, Winter Park, FL 32792

  2506 Argyll Cove, Winter Park, FL 32792
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  /100

  $8,799,000 New Construction

  • 4 Beds
  • 4.5 Baths
  • 4,564 Sq Ft

  2661 Vía Tuscany, Winter Park, FL 32789

  CALLING HIGHEST AND BEST BY 4/30/2025!! Introducing a Unique, Stunning Modern HomeA groundbreaking architectural masterpiece, this one-of-a-kind residence is built with reinforced concrete, steel, and iron framing, featuring floor-to-ceiling glass walls with no traditional windows. Designed to exceed Florida’s strictest building codes, this home follows commercial-grade

  

  Prescilla Vazquez

  PV LUXURY GROUP PA

  (321) 478-2671

  2661 Vía Tuscany, Winter Park, FL 32789
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  /47

  $1,164 - $3,873 per month

  Cranes Landing Apartments

  1-3 Beds

  3440 N Goldenrod Rd, Winter Park, FL 32792

  Cranes Landing invites you home to spacious open-concept living in beautiful Winter Park, Florida. Our community offers an array of one, two, and three bedroom floorplans, including newly renovated homes with premium appliances, all tailored to fit your lifestyle.Choose Cranes Landing for a pet friendly community that boasts a full suite of fantastic amenities.Our brand new resident

  3440 N Goldenrod Rd, Winter Park, FL 32792
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  /2

  $145,000 Sold May 02, 2025

  • 881 Sq Ft
  • $165/SF
  • 271 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1966

  1695 Lee Rd Unit D206, Winter Park, FL 32789

  Discover this charming 2-bedroom, 1-bathroom condo in the tranquil community of Waterfall Cove. With a covered balcony and a walk-in closet in the primary bedroom, this home is ready for its new owner. The community offers a playground, a pool, and includes cable and internet in the HOA fees. Conveniently located near Rollins College and Winter Park's Park Ave, you'll have access to a variety of

  Justin Adams EXP REALTY LLC

  1695 Lee Rd Unit D206, Winter Park, FL 32789
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  /44

  Est $901,554 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,602 Sq Ft

  436 W Swoope Ave, Winter Park, FL 32789

  436 W Swoope Ave, Winter Park, FL 32789

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