Winter Park, FL Homes

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  /13

  $475,000

  • Land
  • 0.76 Acre
  • $625,000 per Acre

  2821 Chantilly Ave, Winter Park, FL 32789

  LAKEFRONT! WINTER PARK! 32789! DOMMERICH, MAITLAND, WINTER PARK HIGH! .75 ACRE INCLUDES RIPARIAN RIGHTS OWNERSHIP LAKE VELLA!

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  2821 Chantilly Ave, Winter Park, FL 32789
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  /9

  $1,500 per month

  • 1 Bed
  • 1 Bath
  • 940 Sq Ft
  • Condo for Rent

  3045 Aaron Burr Ave Unit C, Winter Park, FL 32792

  Property Id: 2093281Condominium for rent unit A ,on the Bottom floor of a 2 story building. Private parking spot requires decal but there's plenty of parking for guests. Gated pool and camera monitored entrances at “The Colonies “ on Goldenrod Rd in south Winter Park . 1 bedroom 1 bath kitchen and living area over 900 square feet. Back door sliding glass door opens to courtyard. This

  3045 Aaron Burr Ave Unit C, Winter Park, FL 32792
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  /2

  $1,075,000 Sold Jul 31, 2025

  • 2,703 Sq Ft
  • $398/SF
  • 140 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1967

  1690 Oneco Ave, Winter Park, FL 32789

  Step into this stunning one-story Spanish Mediterranean home, beautifully renovated in 2006 by renowned E2 Homes. Offering four bedrooms and three baths, this thoughtfully designed residence seamlessly blends timeless charm with modern comforts. The inviting living room features a cozy gas fireplace, setting a warm tone for the home. A formal dining room connects to the spacious kitchen through a

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1690 Oneco Ave, Winter Park, FL 32789
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  /28

  Est $455,609 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,782 Sq Ft

  2901 Clever Ln, Winter Park, FL 32792

  2901 Clever Ln, Winter Park, FL 32792
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  /64

  $2,199,999 Open Sun 2PM - 4PM

  • 4 Beds
  • 4.5 Baths
  • 3,314 Sq Ft

  1752 Chestnut Ave, Winter Park, FL 32789

  Timeless Elegance Meets Modern Comfort in Sought-After Tree StreetsWelcome to this thoughtfully designed, custom-built residence in the coveted Tree Streets community of Winter Park. Boasting 4 bedrooms, 4.5 bathrooms, and over 3,300 square feet of meticulously curated living space, this one-of-a-kind home perfectly blends craftsmanship, comfort, and style.At the heart of the

  Nickolas McKee KELLER WILLIAMS WINTER PARK

  1752 Chestnut Ave, Winter Park, FL 32789
• 

  

  /19

  $1,600 per month

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft
  • Condo for Rent

  3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792

  LOCATION, LOCATION, LOCATION! This well-maintained 2-bedroom, 2-bath condo available for rent is perfectly situated near Full Sail University, UCF, Valencia College, Rollins College. The home features an eat-in kitchen, a spacious great room, a convenient storage room, and a tranquil rear patio—ideal for relaxing outdoors. Enjoy easy access to bike trails, shopping, dining, churches, retail

  Praveen Setty RIGHTHOUSE REALTY LLC

  3267 Forest Oaks Ct Unit 111, Winter Park, FL 32792
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  /2

  $395,000 Sold Jul 31, 2025

  • 1,301 Sq Ft
  • $304/SF
  • 259 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1991

  5418 S Bracken Ct, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. SOLAR PANELS WILL BE PAID OFF AT CLOSING!! Welcome to this move-in ready Winter Park pool home, tucked away in a peaceful cul-de-sac! This gem has been thoughtfully updated with significant renovations, including a composition shingle roof (2019), custom gutters with in-ground drain lines (2019), a Trane HVAC with hurricane slab foundation (2019),

  Chelsea Feinberg EXP REALTY LLC

  5418 S Bracken Ct, Winter Park, FL 32792
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  /32

  Est $700,651 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,592 Sq Ft

  1431 Lake Florence Way, Winter Park, FL 32792

  1431 Lake Florence Way, Winter Park, FL 32792
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  /51

  $6,500,000

  • 6 Beds
  • 5.5 Baths
  • 5,759 Sq Ft

  887 Georgia Ave, Winter Park, FL 32789

  Offered for the first time in over 50 years, this distinguished Winter Park estate is a true traditional gem, nestled on a picturesque brick street and situated on a full 1-acre lot. Exuding timeless charm with a subtle New England ambiance, this residence represents the best of historic Winter Park living—all within walking distance to Park Avenue.This stately 6-bedroom, 5.5-bathroom home

  Kevin McClanahan FANNIE HILLMAN & ASSOCIATES

  887 Georgia Ave, Winter Park, FL 32789
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  /13

  $1,697 per month

  • 2 Beds
  • 2.5 Baths
  • 1,031 Sq Ft
  • Townhouse for Rent

  Unlisted Address

  REDUCED! Winter Park 2 Bedroom Upgraded Townhouse. This unit is tiled throughout with Granite counter tops No carpet to worry about here !! Open Living Dining area with an eat in area in kitchen also~~ Laundry closet in kitchen ~~ Private Patio ~~ 2 Designated parking spaces ~~ Must See!

  Joseph Adkins THE REALTY FACTOR INC

  Unlisted Address
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  /2

  $1,587,500 Sold Jul 31, 2025

  • 3,472 Sq Ft
  • $457/SF
  • 318 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1961

  279 Rippling Ln, Winter Park, FL 32789

  Discover serene lakefront living at its finest in this exquisite 4-bedroom 3 bath home at 279 Rippling Lane. Set against a picturesque backdrop, this property offers breathtaking views and direct lake access, complete with a covered boat dock for your aquatic adventures. The residence seamlessly blends modern luxury with timeless elegance, featuring spacious living areas, high-end finishes, and

  John McDade FANNIE HILLMAN & ASSOCIATES

  279 Rippling Ln, Winter Park, FL 32789
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  /14

  Est $728,219 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1407 Miller Ave, Winter Park, FL 32789

  1407 Miller Ave, Winter Park, FL 32789
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  /14

  $379,999

  • 3 Beds
  • 2 Baths
  • 1,114 Sq Ft

  3383 Hamlet Loop, Winter Park, FL 32792

  Charming Winter Park Home with Private Pool on Corner Lot!Don’t miss this beautifully updated 3-bedroom, 2-bath single-family home nestled in a quiet, tucked-away neighborhood in the heart of Winter Park. Just minutes from the vibrant shops and restaurants of Park Avenue, this centrally located gem offers the perfect blend of comfort, convenience, and charm.Step inside to find

  Cliff Glansen FLATFEE.COM

  3383 Hamlet Loop, Winter Park, FL 32792
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  /38

  $8,990 per month

  • 4 Beds
  • 3.5 Baths
  • 4,188 Sq Ft
  • House for Rent

  2020 Venetian Way, Winter Park, FL 32789

  Only available for a 4–6 month lease. This RARE LAKEFRONT retreat is located on a quiet, tree-lined street in the highly sought-after Vias of Winter Park. Custom-built and elevated on a prime lot with 90 feet of frontage on Lake Maitland, this one-of-a-kind mid-century home offers sweeping views of Lake Maitland and the Isle of Sicily. It combines timeless design, complete privacy, and a premier

  Nadia Moayeri PALMANO GROUP RE BROKERAGE LLC

  2020 Venetian Way, Winter Park, FL 32789
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  /2

  $362,500 Sold Jul 30, 2025

  • 884 Sq Ft
  • $410/SF
  • 103 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1960

  311 E Morse Blvd Unit 6-7, Winter Park, FL 32789

  Priced to sell!! Motivated Seller. Outstanding structural integrity, no big assessments ahead! Whispering Waters passed its structural integrity inspection and reserves study with flying colors—earning compliments for the quality and care of the buildings. This is a very well-managed community, and the $1,054 monthly HOA covers nearly everything, including electricity! The only exception is cable

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  311 E Morse Blvd Unit 6-7, Winter Park, FL 32789
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  /38

  Est $319,247 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,287 Sq Ft

  236 Balfour Dr Unit 21, Winter Park, FL 32792

  236 Balfour Dr Unit 21, Winter Park, FL 32792
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  /56

  $4,995,000

  • 4 Beds
  • 6.5 Baths
  • 6,242 Sq Ft

  1760 Via Venetia, Winter Park, FL 32789

  Discover unparalleled luxury in this meticulously crafted estate home, where no detail has been overlooked in creating the ultimate in sophisticated living. Encompassing over 6,200 square feet of exquisite interior space on an expansive .42-acre lot, this stunning 4-bedroom, 5.5-bathroom residence offers an extraordinary blend of timeless elegance and modern convenience just steps from the

  Kelly Price KELLY PRICE & COMPANY LLC

  1760 Via Venetia, Winter Park, FL 32789
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  /30

  $5,600 per month

  • 4 Beds
  • 4 Baths
  • 3,654 Sq Ft
  • House for Rent

  960 Georgia Ave, Winter Park, FL 32789

  Quintessential Winter Park Stunner. This well appointed home is situated on a half acre corner lot just two blocks away from Winter Park's shopping and dining district, Park Avenue. Surrounded by majestic oak trees you find this classic 4 bedroom, 4 bath home with 3600sq ft of living space. An abundance of natural light welcomes you in the homes central hub, the Family Room. Anchored by one of

  Alison Ashby CORCORAN PREMIER REALTY

  960 Georgia Ave, Winter Park, FL 32789
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  /2

  $465,000 Sold Jul 30, 2025

  • 2,014 Sq Ft
  • $231/SF
  • 100 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1982

  1776 E Cheryl Dr, Winter Park, FL 32792

  Welcome to 1776 E Cheryl Dr, located on a quiet cul-de-sac in desirable Winter Park. The home offers a split plan with 4 bedrooms and 2 bathrooms. The living room has a beautiful stone fireplace. It has a separate indoor laundry room and an attached 2-car garage. Notes of interests include a fully renovated guest bathroom (2018), fully renovated kitchen (2023), new roof and gutters (2021),

  Donna Mink MINK REALTY

  1776 E Cheryl Dr, Winter Park, FL 32792
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  /29

  Est $328,123 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,408 Sq Ft

  3113 Crown Jewel Ct, Winter Park, FL 32792

  3113 Crown Jewel Ct, Winter Park, FL 32792
• 

  

  /29

  $450,000

  • 4 Beds
  • 3 Baths
  • 1,804 Sq Ft

  2464 Lotafun Ave, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. A rare gem nestled in one of Winter Park’s most secluded subdivisions—just 25 homes tucked into a quiet, tree-lined enclave.This block-built mid-century home offers four bedrooms, three baths, and sits proudly on a spacious double lot. Inside, travertine floors add timeless elegance, while oversized windows flood the space with natural

  Irina Paul FUTURE HOME REALTY INC

  2464 Lotafun Ave, Winter Park, FL 32789
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  /21

  $1,399 per month

  • 1 Bed
  • 1 Bath
  • 735 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 703, Winter Park, FL 32792

  Spacious one-bedroom condominium in Golfside Villas! This move in ready first-floor unit includes a large living room, Dining room with patio, open kitchen with New stainless steel appliances, Great location. Minutes from Baldwin Park and Full Sail, Golfside Villas has excellent access via Semoran Boulevard to downtown Winter Park, UCF, downtown Orlando and the Orlando International Airport.

  Gregorio Henriques CENTURY 21 CARIOTI

  1000 S Semoran Blvd Unit 703, Winter Park, FL 32792
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  /2

  $380,000 Sold Jul 30, 2025

  • 1,910 Sq Ft
  • $199/SF
  • 142 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1966

  3458 Balsam Dr, Winter Park, FL 32792

  Seller to contribute $1500 to buyers closing cost. Come see this charming 3 bedroom, 2 bath pool home, located in Winter Park, FL. Home is centrally located and easily accessible to major highways, downtown Orlando, UCF, Rollins College, entertainment, restaurants, shopping and much more. The driveway has an extended parking pad, for extra parking. The well maintained landscaped backyard and

  Marquita Shiever, PA CENTURY 21 BE3

  3458 Balsam Dr, Winter Park, FL 32792
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  /11

  Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,851 Sq Ft

  1405 Miller Ave, Winter Park, FL 32789

  1405 Miller Ave, Winter Park, FL 32789
• 

  

  /37

  $649,000

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

  2758 Banchory Rd, Winter Park, FL 32792

  Charming Pool Home in Prime Winter Park Location Welcome to 2758 Banchory Road — a true gem nestled in the heart of the desirable Winter Park Pines community. This beautifully maintained 3-bedroom, 2-bath ranch-style home offers the ideal combination of comfort, privacy, and location. With a private swimming pool, lush landscaping, and no direct front neighbors on a quiet cul-de-sac street,

  Erwin Vargas MR VARGAS PROPERTY MANAGEMENT LLC

  2758 Banchory Rd, Winter Park, FL 32792
• 

  

  /23

  $1,695 per month

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft
  • Condo for Rent

  851 Miles Ave Unit 9, Winter Park, FL 32789

  Imagine living in this completely renovated two-bedroom, one-bathroom second-floor condominium unit near downtown Winter Park at Aragon Condos. This intimate, two-building, two-story condominium community comprises just twenty-eight units focused around a central courtyard.Features include: • Recently remodeled kitchen including all cabinetry, countertops, marble tile backsplash,

  Richard Traynor FLORIDA ONE REAL ESTATE LLC

  851 Miles Ave Unit 9, Winter Park, FL 32789
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  /2

  $280,000 Sold Jul 30, 2025

  • 1,074 Sq Ft
  • $261/SF
  • 130 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1964

  700 Melrose Ave Unit A22, Winter Park, FL 32789

  HUGE PRICE CHANGE! Welcome to this beautifully updated second-floor unit, offering a fresh and modern living experience. Featuring brand-new luxury vinyl flooring, new appliances, granite countertops, as well as upgraded fans and light fixtures, this home combines style and comfort. Enjoy breathtaking, floor-to-ceiling pond views from the sunroom, creating the perfect spot to relax and

  Olivia Maxwell FANNIE HILLMAN & ASSOCIATES

  700 Melrose Ave Unit A22, Winter Park, FL 32789
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  /19

  Est $276,609 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 939 Sq Ft

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792

  2404 Gallery View Dr Unit 1, Winter Park, FL 32792
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  /32

  $525,000

  • 4 Beds
  • 2 Baths
  • 2,030 Sq Ft

  1713 W Cheryl Dr, Winter Park, FL 32792

  REDUCED!!!!! Welcome to Winter Park luxury living in the sought-after Carolyn Estates, offering convenience, upscale updates, and a top-tier location. This fully renovated 4-bedroom, 2-bath pool home on a private corner lot, offering over 2,000sq ft of stunning finished space is in move in ready condition. This home combines smart upgrades, designer finishes, and relaxation-focused amenities like

  Andi Gamble LPT REALTY, LLC

  1713 W Cheryl Dr, Winter Park, FL 32792
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  /14

  $2,350 per month

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft
  • House for Rent

  5323 Poinsetta Ave, Winter Park, FL 32792

  Winter Park and NO HOA!! Newly remodeled 3/2 1,500 sqft $2,350/mo. Just a 1 minute car ride or 5-7 minute walk to Eastbrook Elementary. Remodeled kitchen with all the bells and whistles (new cabinets, countertops, backsplash, faucet, lights, and appliances - you get the idea, it's fancy!). Remodeled bathrooms with subway tiles, new tub, new vanities, new countertops, new toilets, new lighting &

  Ginnie England MAGNOLIA PROPERTY SALES

  5323 Poinsetta Ave, Winter Park, FL 32792
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  /2

  $415,000 Sold Jul 29, 2025

  • 1,476 Sq Ft
  • $281/SF
  • 7 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  5210 Poinsetta Ave, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. Welcome to 5210 Poinsetta Ave, your dream retreat in charming Winter Park, FL! This beautifully remodeled ranch-style home is a blend of modern elegance and comfort. As you enter, the foyer warmly invites you into a spacious living area, perfect for relaxing or entertaining friends. The sleek, modern

  Godfrey Coxe PA CHARLES RUTENBERG REALTY ORLANDO

  5210 Poinsetta Ave, Winter Park, FL 32792
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  /34

  Est $227,781 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792

  1925 Woodcrest Dr Unit E, Winter Park, FL 32792
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  /18

  $137,000

  • 1 Bed
  • 1 Bath
  • 796 Sq Ft

  1000 S Semoran Blvd Unit 716, Winter Park, FL 32792

  PRICED TO SELL! Whether you're looking for a great home or an investment opportunity, THIS IS IT! This great unit has a LOW HOA, THAT INCLUDES THE WATER, adding even more value to it!! This AMAZING CONDO features an UPDATED KITCHEN and BATHROOM, along with beautiful WOOD FLOORING THROUGHOUT for a modern look. LOCATION, LOCATION! Ideally situated near Baldwin Park, Full Sail University, and Winter

  Nathalie Romero HOME WISE REALTY GROUP, INC.

  1000 S Semoran Blvd Unit 716, Winter Park, FL 32792
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  /67

  $5,050 per month

  • 4 Beds
  • 3 Baths
  • 2,422 Sq Ft
  • House for Rent

  2627 Verona Trail, Winter Park, FL 32789

  Beautiful 4 bedroom/ 3 bath Pool home for rent in Winter Park Range, D/W, Disposal, Central Heat and A/C.

  Rick Sein REALSOURCE PROPERTY MANGNT LLC

  2627 Verona Trail, Winter Park, FL 32789
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  /2

  $480,000 Sold Jul 28, 2025

  • 1,598 Sq Ft
  • $300/SF
  • 3 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1545 Indiana Ave Unit B, Winter Park, FL 32789

  Tucked away on a quiet street blocks from the cultural heartbeat of Winter Park is this 3-bedroom, 2.5-bath townhouse-style condo that offers a balance of comfort, convenience, and charm. With nearly 1,600 square feet of thoughtful space, the two-story home lives large, featuring an open-concept main floor with high ceilings, ceramic tile throughout, a spacious kitchen with granite counters and

  Ron Murray MAGIC REALTY LLC

  1545 Indiana Ave Unit B, Winter Park, FL 32789
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  /31

  Est $753,461 Not Listed For Sale

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

  2312 Kestrel Perch Place, Winter Park, FL 32792

  2312 Kestrel Perch Place, Winter Park, FL 32792
• 

  

  /41

  $410,000

  • 4 Beds
  • 3 Baths
  • 1,906 Sq Ft

  3415 N Goldenrod Rd, Winter Park, FL 32792

  THIS HOME HAS IT ALL! Private lot with NO rear neighbors and NO HOA. Features 4 bedrooms, 3 bathrooms, including a potential mother-in-law suite, PLUS a huge oversized bonus room perfect for a game room, office, or home gym! Tile floors throughout, brand new granite countertops and new cabinets in the kitchen and bathrooms, and brand new stainless steel appliances.Enjoy the open floor plan with a

  Maria Borges Jaime BORGES & JAIME REAL ESTATE , LLC

  3415 N Goldenrod Rd, Winter Park, FL 32792
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  /13

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft
  • Townhouse for Rent

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792

  Location! Location! Location! This exactly what you are looking for, a nice home in a great location. This a great unit featuring a nice kitchen with stainless steel appliances, and an updated flooring with luxury vinyl plank. This unit has an indoor heated swimming pool with an exercise room. This property is located near all of the main central Florida colleges. Come and enjoy with your family

  Smithj Salomon LAWHUN ENTERPRISES IV, LLC DBA: FLORIDA REALTY INVESTMENTS IV

  3486 Bougainvillea Dr Unit B, Winter Park, FL 32792
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  /2

  $389,000 Sold Jul 25, 2025

  • 1,581 Sq Ft
  • $246/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1970

  7331 Blue Jacket Place W, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Incredible Value! Priced to sell below market value—this is your chance to secure a fully upgraded home at a price that won’t last long. Act fast before it's gone!Welcome to this beautifully updated 3-bedroom, 2-bathroom home located in the highly desirable Winter Park community with no HOA! This luxury home sits on a large, fully fenced lot and

  Wendy Aldana LLC NETWORTH REALTY OF ORLANDO, LLC

  7331 Blue Jacket Place W, Winter Park, FL 32792
• 

  

  /18

  Est $189,156 Not Listed For Sale

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

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792

  2911 Antique Oaks Cir Unit GE, Winter Park, FL 32792

Showing Results 521 - 560, Page 14 of 18