Winter Park, FL Homes

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  /11

  $3,950,000

  • Land
  • 8 Acres
  • $473,621 per Acre

  2403 Euston Rd, Winter Park, FL 32789

  Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres

  Marie Ledbetter COLDWELL BANKER RESIDENTIAL RE

  2403 Euston Rd, Winter Park, FL 32789
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  /20

  $2,875 per month

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft
  • House for Rent

  2108 Shirewood Ct, Winter Park, FL 32792

  Property Id: 2008122Discover comfort and style in this beautifully updated 3-bedroom, 2-bathroom pool house with a private fenced spacious backyard located on a quiet cul-de-sac in a well-established neighborhood of Winter Park, FL on a treed lot. Perfectly situated within walking distance to local shops, restaurants, and essential amenities. Easy drive to 408/417 & Rollins, UCF, Full

  2108 Shirewood Ct, Winter Park, FL 32792
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  /2

  $749,000 Sold Jun 16, 2025

  • 2,532 Sq Ft
  • $296/SF
  • 3 Days On Market

  • 5 Beds
  • 2 Baths
  • Built 1968

  2907 Summerfield Rd, Winter Park, FL 32792

  Just in time for summer! Here's the trifecta of size, location, and condition that you've been waiting for! This beautiful 5 bedroom, 2 bath, 2 fireplaces, corner lot with a pool home is ready for your family! Come make memories for years to come as this home is large enough to grow in. Beautiful hardwood floors through out main living areas, large tiled Florida room with fireplace overlooking

  Kim Helmling MILLER GRANT AND COMPANY

  2907 Summerfield Rd, Winter Park, FL 32792
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  /20

  Est $474,991 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,076 Sq Ft

  2448 Firstlight Way, Winter Park, FL 32792

  2448 Firstlight Way, Winter Park, FL 32792
• 

  

  

  /23

  $360,000

  • 3 Beds
  • 2 Baths
  • 987 Sq Ft

  1921 Dartmouth Ave, Winter Park, FL 32789

  Charming, Fully Renovated Bungalow in the Heart of Winter Park! Welcome to this beautifully upgraded bungalow that makes every square foot count! Nestled perfectly between Winter Park and College Park, this fully renovated gem blends modern upgrades with timeless charm. From the moment you arrive, the custom-built front pergola and all-new paver driveway invite you in with style.Step

  Pat Hancock THOMAS LYNNE REALTY GROUP LLC

  1921 Dartmouth Ave, Winter Park, FL 32789
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  /16

  $2,700 per month

  • 3 Beds
  • 2.5 Baths
  • 1,907 Sq Ft
  • Townhouse for Rent

  1943 Canny Cove, Winter Park, FL 32792

  2024 Townhome with 3 bedrooms and 2.5 bathrooms located in gated community a resort-style pool with a cabana. High-speed 1GB fiber optic internet and 75 cable channels are included in the rent. Enclosed attached 1 car garage and driveway parking. Stone countertops, SS appliances, and tile floors on level one, all bedrooms and laundry are upstairs.

  John Tremblay THE TEAM REAL ESTATE GROUP INC

  1943 Canny Cove, Winter Park, FL 32792
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  /2

  $718,500 Sold Jun 13, 2025

  • 2,069 Sq Ft
  • $347/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1981

  1130 Washington Ave Unit 11C, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. A rare (and low-maintenance!) gem, this 3 bed/2.5 bath home is located just around the corner from Park Avenue and Rollins College. Tucked away in the most perfect location, this 2-story Winter Park condo was stripped down to the studs and completely remodeled in 2007 with all new plumbing, electrical, ductwork, flooring, appliances, and natural gas

  MaryStuart Day FANNIE HILLMAN & ASSOCIATES

  1130 Washington Ave Unit 11C, Winter Park, FL 32789
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  /22

  Est $226,418 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792

  200 Saint Andrews Blvd Unit 1902, Winter Park, FL 32792
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  /28

  $279,900

  • 2 Beds
  • 2 Baths
  • 1,241 Sq Ft

  3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792

  Cute, updated, and quietly tucked away, this one-story townhome is full of pleasant surprises. Situated on a corner lot with no rear neighbors, it offers just the right mix of privacy and convenience. Inside, you’ll find ceramic tile and luxury vinyl flooring throughout...so no carpet in sight! The kitchen and both bathrooms have been tastefully updated, and it’s all topped off with a brand new

  Allison Day RE/MAX TOWN & COUNTRY REALTY

  3153 Greenwood St Unit Winter Spr, Winter Park, FL 32792
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  /4

  $1,450 per month

  • 2 Beds
  • 2 Baths
  • 1,042 Sq Ft
  • House for Rent

  3054 George Mason Ave, Winter Park, FL 32792

  *ESTIMATED TOTAL MONTHLY LEASING PRICE: $1,499.95Base Rent: $1,450.00Filter Delivery: $5.00Renters Insurance: $10.95$1M Identify Protection, Credit Building, Resident Rewards, Move-In Concierge: $34.00 *The estimated total monthly leasing price does not include utilities or optional/conditional fees, such as: pet, utility service, and security deposit waiver fees. Our

  3054 George Mason Ave, Winter Park, FL 32792
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  /2

  $645,000 Sold Jun 13, 2025

  • 1,910 Sq Ft
  • $338/SF
  • 18 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  796 Mcintyre Ave, Winter Park, FL 32789

  Welcome to 796 McIntyre Avenue, Winter Park, FL 32789. This stunning and serene retreat is the ideal place to call home, perfectly situated on a tree-lined brick street within walking distance to Rollins College and all that Park Avenue has to offer. A charming driveway leads to your two-car garage and private front entrance. Upon entering, you'll be greeted by a bright and airy townhome that

  Catherine D'Amico FANNIE HILLMAN & ASSOCIATES

  796 Mcintyre Ave, Winter Park, FL 32789
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  /77

  Est $792,308 Not Listed For Sale

  • 5 Beds
  • 4 Baths
  • 3,496 Sq Ft

  7904 Pleasant Pine Cir, Winter Park, FL 32792

  7904 Pleasant Pine Cir, Winter Park, FL 32792
• 

  

  /18

  $225,000

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

  3220 Netherwood Dr, Winter Park, FL 32792

  Incredible Investment Opportunity in a Desirable Location!This 2-bedroom, 1.5-bath home is full of potential and ready for a transformation. It's a fantastic opportunity for investors, flippers, or anyone seeking a high-potential investment. With just a little TLC, this property can be turned into a beautiful primary residence or a strong income-producing rental. Whether you're looking to

  Nimrah Ashraf THE FIRM RE

  3220 Netherwood Dr, Winter Park, FL 32792
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  /16

  $1,650 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Townhouse for Rent

  2534 Zelina Point, Winter Park, FL 32792

  This property offers a prime location, and beautifully maintained interiors in good condition—ready for immediate move-in! 2 bedroom 2 bath half duplex in Winter Park Aloma area. $1700 monthLY with $2000 deposit for approved applicants. $100 application fee. Standard screening applies. Call your agent today to schedule a showing.

  Charles Maligaya LA REALTY SERVICES LLC

  2534 Zelina Point, Winter Park, FL 32792
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  /2

  $215,000 Sold Jun 13, 2025

  • 1,578 Sq Ft
  • $136/SF
  • 52 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1974

  7468 Swallow Run Unit 38, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this charming two bedroom, two and a half bathroom condo in the heart of Winter Park. This home offers a spacious and functional layout with a half bath on the first floor, perfect for guests, and an interior laundry room for added convenience. The living room features a cozy fireplace, creating a warm and inviting atmosphere. Two sliding

  Chris Creegan CREEGAN GROUP

  7468 Swallow Run Unit 38, Winter Park, FL 32792
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  /17

  Est $327,438 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,160 Sq Ft

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789

  520 Killarney Bay Ct Unit 2, Winter Park, FL 32789
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  /58

  $3,975,000

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  In one of Winter Park’s desirable neighborhoods, this stunning four-bedroom, five-bath modern masterpiece with Control4 automation offers a blend of luxury and function. Designed with sleek lines and open-concept living, the home showcases Italian engineered wood flooring throughout, creating an elegant yet inviting atmosphere. Expansive windows flood the interiors with natural light, seamlessly

  Nathalie Bates PREMIER SOTHEBY'S INTL. REALTY

  1742 Temple Dr, Winter Park, FL 32789
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  /18

  $2,990 per month

  • 4 Beds
  • 2 Baths
  • 2,088 Sq Ft
  • House for Rent

  7145 Timber Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $3254.90. That covers your base rent, $2990.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  7145 Timber Dr, Winter Park, FL 32792
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  /2

  $265,000 Sold Jun 13, 2025

  • 1,296 Sq Ft
  • $204/SF
  • 82 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  2464 Harbour Way, Winter Park, FL 32792

  New Price !!Location Winter Park! Charming 2-Bedroom, 2-Bath Single-Story Townhouse – Priced to Sell! This well-located just minutes from shopping, restaurants, banks, and more. Designed for comfort, the open floor plan includes a spacious living-dining combo, tile floors, and a convenient pass-through to the kitchen equipped with granite countertops, light fixtures, wood cabinets, and

  Ana Manzo AGENT TRUST REALTY CORPORATION

  2464 Harbour Way, Winter Park, FL 32792
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  /28

  Est $305,565 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,608 Sq Ft

  7113 Swallow Run Unit 2, Winter Park, FL 32792

  7113 Swallow Run Unit 2, Winter Park, FL 32792
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  /47

  $730,000

  • 5 Beds
  • 3.5 Baths
  • 3,568 Sq Ft

  7895 Pleasant Pine Cir, Winter Park, FL 32792

  Seller Motivated!Welcome to Your Dream Home in Enclave at Aloma, Winter Park!Step into this stunningly maintained 5-bedroom, 3.5-bathroom residence located in the highly sought-after gated community of Enclave at Aloma. Perfectly positioned with no rear neighbors, this home offers ultimate privacy and tranquility.As you enter, you’ll immediately notice the elegance of

  Yvette Hoover ALL REAL ESTATE & INVESTMENTS

  7895 Pleasant Pine Cir, Winter Park, FL 32792
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  /12

  $1,550 per month

  • 2 Beds
  • 2 Baths
  • 1,003 Sq Ft
  • Condo for Rent

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792

  Welcome to Golfside Villas. This community is nestled near Downtown Orlando, Full Sail, UCF, Lynx bus stop, major shopping centers, restaurants, I-4, 408, & Orlando International Airport. This condominium features an open floor plan that consist of 2 bedrooms, 2 bathrooms, and a screened in patio. Over 1000 sqft of living space awaits you with a few upgrades. This neighborhood features a laundry

  Damon Mayers MAYERS REAL ESTATE LLC

  1000 S Semoran Blvd Unit 115, Winter Park, FL 32792
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  /2

  $290,000 Sold Jun 13, 2025

  • 1,122 Sq Ft
  • $258/SF
  • 464 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1954

  1908 Carrigan Ave, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this stunning property with a natural color palette that creates a soothing ambiance throughout. The kitchen boasts a nice backsplash, adding a touch of elegance to this functional space. The master bedroom offers a spacious walk-in closet, providing ample storage for your wardrobe. With additional rooms for flexible living space, the

  GREGORY BLACKALL VERANDA REALTY GROUP

  1908 Carrigan Ave, Winter Park, FL 32792
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  /17

  Est $462,051 Not Listed For Sale

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

  2760 Bright Bird Ln, Winter Park, FL 32792

  2760 Bright Bird Ln, Winter Park, FL 32792
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  /55

  $1,225,000

  • 4 Beds
  • 4.5 Baths
  • 3,408 Sq Ft

  2890 Wild Ginger Ct, Winter Park, FL 32792

  Discover the exceptional Winter Park neighborhood of Bear Gully Pointe, a gated community rich with amenities and anchored by a 137-acre spring-fed lake. This meticulously crafted home sits in a private cul-de-sac and stretches over almost 1⁄2 acre with mature landscaping and includes a secluded, fenced back yard. Function is paramount with a three-way split floorplan with four bedrooms and 4.5

  Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

  2890 Wild Ginger Ct, Winter Park, FL 32792
• 

  

  /20

  $2,249 per month

  • 3 Beds
  • 2 Baths
  • 1,549 Sq Ft
  • House for Rent

  1752 W Cheryl Dr, Winter Park, FL 32792

  Lease this home and get more from Invitation Homes professional property management. This home comes fully loaded with quality amenities, must-have services, high-end tech and ProCare® professional maintenance. Your estimated total monthly payment is $2393.90. That covers your base rent, $2249.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1752 W Cheryl Dr, Winter Park, FL 32792
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  /2

  $890,000 Sold Jun 12, 2025

  • 2,265 Sq Ft
  • $393/SF
  • 114 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2024

  1762 Mondrian Cir, Winter Park, FL 32789

  Act now - only two new units remain! Introducing a stunning brand-new modern brownstone in the heart of Winter Park, offering access to Lake Killarney. Located in an exclusive community of 30 contemporary townhomes, each meticulously designed residence boasts exquisite finishes, expansive storefront-style windows, and 11' ceilings to flood the interiors with natural light. This 3-bedroom, 3 bath

  Brian Teach COLDWELL BANKER RESIDENTIAL RE

  1762 Mondrian Cir, Winter Park, FL 32789
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  /18

  Est $236,264 Not Listed For Sale

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

  7413 Belle River Ct Unit 3, Winter Park, FL 32792

  7413 Belle River Ct Unit 3, Winter Park, FL 32792
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  /32

  $410,000 Open Sun 1PM - 3PM

  • 2 Beds
  • 2.5 Baths
  • 1,536 Sq Ft

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789

  Welcome to Killarney Bay—Winter Park’s best-kept secret for tranquil lakeside living, and just steps from the city’s finest shopping and dining!This beautifully updated and spacious 2-bedroom, 2.5-bath townhome-style condo offers a rare blend of modern upgrades and classic charm. Enjoy vaulted ceilings, a wood-burning fireplace, and rich wood-like flooring throughout. The open-concept kitchen

  Blaike Gill KELLER WILLIAMS WINTER PARK

  240 Killarney Bay Ct Unit 4, Winter Park, FL 32789
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  /55

  $2,995 per month

  • 2 Beds
  • 2.5 Baths
  • 1,214 Sq Ft
  • Condo for Rent

  660 Killarney Bay Ct Unit 6, Winter Park, FL 32789

  Experience luxury lakeside living in Winter Park on Lake Killarney with expansive views in this beautifully remodeled 2-bedroom, 2.5-bathroom, second-floor end-unit condominium. Nestled in a highly private setting, this home offers an open floor plan designed to maximize natural light and showcase the serene water views from the kitchen, breakfast nook, primary bedroom, and living room.

  Anthony Consalvo FLORIDA ONE REAL ESTATE LLC

  660 Killarney Bay Ct Unit 6, Winter Park, FL 32789
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  /2

  $1,625,000 Sold Jun 12, 2025

  • 4,227 Sq Ft
  • $384/SF
  • 95 Days On Market

  • 5 Beds
  • 6 Baths
  • Built 2003

  1470 Place Picardy, Winter Park, FL 32789

  Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  1470 Place Picardy, Winter Park, FL 32789
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  /5

  Est $456,029 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,477 Sq Ft

  7494 Betty St, Winter Park, FL 32792

  7494 Betty St, Winter Park, FL 32792
• 

  

  /23

  $174,900 Open Sun 12PM - 2PM

  • 1 Bed
  • 1 Bath
  • 727 Sq Ft

  200 St Andrews Blvd Unit 601, Winter Park, FL 32792

  Welcome to this spacious and beautifully updated first-floor condo with 1 bedroom, 1 bathroom in the heart of Winter Park, the highly sought after Four Seasons community. This unit offers the convenience of walk-up access and a covered carport just steps from your private screened patio and laundry inside the unit. The kitchen was remodeled in 2021 and features white shaker-style cabinetry, a

  Amy Turner KELLER WILLIAMS WINTER PARK

  200 St Andrews Blvd Unit 601, Winter Park, FL 32792
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  /16

  $2,480 per month

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • House for Rent

  1729 Puritan Ave, Winter Park, FL 32792

  Beautiful, pet-friendly home coming soon! Apply now, Move-In is available on or after the listed date. Upon approval, $500 reservation deposit to reserve (applied to security deposit and/or refundable). Application fee: $50 per adult. Security Deposit: one month?s rent. Pet fees: $250 + $35/mo per pet. Some homes may include pool ($150/mo), septic ($15/mo), and/or HOA fees; other fees may apply.

  1729 Puritan Ave, Winter Park, FL 32792
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  /2

  $575,000 Sold Jun 11, 2025

  • 2,275 Sq Ft
  • $253/SF
  • 4 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1989

  4353 Steed Terrace, Winter Park, FL 32792

  Gorgeous, updated, 4 bedroom pool home in the Winter Park community of Kings Cove! Incredible outdoor oasis with a sparkling screened pool, spacious 35 x 13 covered lanai including a summer kitchen with refrigerator, sink and storage cabinets. The heart of the home is the renovated kitchen with quartz counters, breakfast bar, mosaic tile backsplash, pantry, and a large breakfast nook all

  Ingrid Livingston COLDWELL BANKER RESIDENTIAL RE

  4353 Steed Terrace, Winter Park, FL 32792
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  /30

  Est $747,783 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,637 Sq Ft

  1835 Jessica Ct, Winter Park, FL 32789

  1835 Jessica Ct, Winter Park, FL 32789
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  /45

  $1,976,000

  • 5 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  617 Worthington Dr, Winter Park, FL 32789

  Discover luxurious living in the heart of Winter Park! Crafted with exquisite attention to detail, this 5-bedroom, 4.5-bathroom pool residence showcases absolute perfection and modern elegance. Built in 2018 by David Weekley Homes, the property boasts a captivating stone facade and a private backyard oasis featuring a saltwater, heated pool and spa with water feature, and ambient lighting — an

  Kelly Price KELLY PRICE & COMPANY LLC

  617 Worthington Dr, Winter Park, FL 32789
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  /26

  $2,950 per month

  • 3 Beds
  • 2 Baths
  • 1,130 Sq Ft
  • Condo for Rent

  644 N Knowles Ave Unit 8, Winter Park, FL 32789

  Welcome to your private retreat in the heart of Downtown Winter Park. This exclusive address affords views of the world famous Winter Park 9 course, and the timeless Casa Feliz, right from your balcony! This wonderful 3/2 LARGE condo features: a FULLY renovated kitchen, equipped with designer touches, and top of the line stainless steel appliances, solid surface flooring throughout, clean and

  Raul Veitia BELMONT REALTY

  644 N Knowles Ave Unit 8, Winter Park, FL 32789
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  /2

  $350,000 Sold Jun 11, 2025

  • 1,550 Sq Ft
  • $226/SF
  • 27 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 2004

  1517 Florentino Ln, Winter Park, FL 32792

  Welcome to your dream home nestled in the highly sought-after Vistas at Lake Howell, a gated community, located in Winter Park. This stunning 2-bedroom townhome offers a perfect blend of comfort, style and convenience. Step inside to the inviting living spaces and discover a beautifully designed open floor plan that seamlessly connects the living, dining, and kitchen areas. The spacious living

  Lou DiBerardino KELLER WILLIAMS WINTER PARK

  1517 Florentino Ln, Winter Park, FL 32792
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  /3

  Est $2,167,303 Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  150 Whipple Ave, Winter Park, FL 32789

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