Winter Park, FL Homes

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  /25

  $514,900

  • 4 Beds
  • 2 Baths
  • 1,843 Sq Ft

  8136 Lazy Bear Ln, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to Enclave at Aloma — a gated community quietly nestled in a convenient Winter Park location, offering easy access to everything you need. This meticulously maintained 4 bedroom, 2 bathroom home has only had one owner since it was built in 2013, and it shows! From the moment you arrive, you’ll notice the charming curb appeal, manicured

  Maria Van Warner FANNIE HILLMAN & ASSOCIATES

  8136 Lazy Bear Ln, Winter Park, FL 32792
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  /8

  $1,350 per month

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

  2948 Antique Oaks Cir Unit 91, Winter Park, FL 32792

  Property Id: 734955One-bedroom condominium in beautiful Parkview Village community located directly across from Full Sail. The unit includes a full-size washer and dryer and has a small screened-in patio. Rent includes sewer, water, and garbage. Parkview Village is conveniently located on 436 and within a short drive of UCF and downtown Winter Park. Please contact Callan Fitzgerald for

  2948 Antique Oaks Cir Unit 91, Winter Park, FL 32792
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  /2

  $790,000 Sold Aug 01, 2025

  • 1,240 Sq Ft
  • $637/SF
  • 11 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1955

  1217 Kenwood Ave, Winter Park, FL 32789

  The inviting bungalow at 1217 Kenwood Ave is located just a few houses off famed Park Avenue and steps from the Winter Park Village, which is fresh off a $50 million transformation and includes popular bars and restaurants, a movie theater and shopping. The home was fully renovated in 2018 with updates to the HVAC, electrical, plumbing, flooring, subflooring, interiors, and a new roof- offering

  Kurt Lehmann LEHMANN REALTY INC.

  1217 Kenwood Ave, Winter Park, FL 32789
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  /17

  Est $325,071 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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  /73

  $489,900

  • 5 Beds
  • 2 Baths
  • 2,044 Sq Ft

  1028 Princess Gate Blvd, Winter Park, FL 32792

  The seller is offering a $15,000 concession to the buyer, to be applied toward allowable closing costs and/or prepaid expensesA Fully Renovated Gem in the Heart of Winter ParkStep into this beautifully updated 5-bedroom, 2-bathroom home located in one of Winter Park’s most sought-after neighborhoods. With over 2,000 square feet of stylish and functional living space, this residence offers

  Jose Hernandez LA ROSA REALTY CW PROPERTIES L

  1028 Princess Gate Blvd, Winter Park, FL 32792
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  /26

  $1,895 per month

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

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792

  Come view this 2 bed, 2.5 bathroom home located in the beautiful Winter Park area. This home is located in a great area with close proximity to shopping, restaurants, multiple freeways, Full Sail, UCF, etc. Each bedroom are large in space and have their own private en-suite bathroom. On the first floor, you’ll find an open concept with views of the newer kitchen with granite counterops, living

  Christopher Bright BEST ORLANDO PROPERTY MANAGEMENT LLC

  7337 Cedar Creek Ct Unit 75, Winter Park, FL 32792
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  /2

  $749,000 Sold Aug 01, 2025

  • 1,939 Sq Ft
  • $386/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

  1429 Indiana Ave, Winter Park, FL 32789

  Like new and totally turn-key! Built by award-winning Winter Park Custom Homes, coastal modern residence offers thoughtful design, high-end finishes, and an unbeatable location in Winter Park's coveted 32789 ZIP code. 3-bedroom, 2.5-bath home combines privacy with convenience. Minutes from Park Avenue, downtown Orlando and major local destinations. The home features authentic reclaimed

  Jennifer Sloan KELLY PRICE & COMPANY LLC

  1429 Indiana Ave, Winter Park, FL 32789
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  /28

  Est $280,512 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
• 

  

  /24

  $179,000

  • 2 Beds
  • 2 Baths
  • 987 Sq Ft

  200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792

  Welcome to the beautiful community of Four Seasons! This well-established condominium complex is coveted for its fantastic location in Winter Park, excellent schools, proximity to restaurants, grocery stores, shopping and Park Avenue. Four Seasons is a 20-acre, park-style neighborhood featuring tranquil courtyards with mature landscaping and majestic oak trees. Four Seasons amenities include 3

  Jill Healey KELLER WILLIAMS WINTER PARK

  200 Saint Andrews Blvd Unit 2206, Winter Park, FL 32792
• 

  

  /20

  $2,715 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 $2979.90. That covers your base rent, $2715.00 + 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

  $505,000 Sold Aug 01, 2025

  • 2,250 Sq Ft
  • $224/SF
  • 60 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1968

  715 Roughbeard Rd, Winter Park, FL 32792

  Price Improvement! Enjoy Winter Park living on this quiet street, with no thru traffic. This home is the perfect opportunity to live in the coveted neighborhood of WINTER PARK PINES. This 4 bedroom, 2 bath POOL home is a well-built traditional home waiting for its next owner. The ROOF was replaced in 2024 and the remaining home is waiting for your personal touch. The oversize Florida room has

  Christine Gerardi NEXTHOME DIAMOND PROPERTIES

  715 Roughbeard Rd, Winter Park, FL 32792
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  /17

  Est $444,656 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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  /27

  $449,900

  • 4 Beds
  • 2 Baths
  • 1,627 Sq Ft

  1849 Viburnum Ln, Winter Park, FL 32792

  Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom, 2-bath concrete block home has been recently renovated and features new appliances, stunning waterfall countertops, all-new bathrooms, fresh interior and exterior paint, brand-new flooring, granite countertops, a stylish backsplash, and updated plumbing throughout. Enjoy the spacious backyard, a 2-car

  Lesly Hijar REAL BROKER, LLC

  1849 Viburnum Ln, Winter Park, FL 32792
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  /17

  $1,840 per month

  • 2 Beds
  • 1 Bath
  • 1,160 Sq Ft
  • Townhouse for Rent

  2510 Roxbury Rd, Winter Park, FL 32789

  This beautifully renovated half-duplex is just blocks from Lake Killarney, ideally situated between College Park and the Winter Park shopping district. Enjoy quick access to local favorites like the Orlando Science Center, Winter Park Village, and Mead Gardens—all just minutes away.The home features 2 bedrooms, 1 bathroom, and a dedicated carport for convenient parking. Inside, you'll

  Angela Fettig KELLER WILLIAMS REALTY AT THE PARKS

  2510 Roxbury Rd, Winter Park, FL 32789
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  /2

  $265,000 Sold Jul 31, 2025

  • 1,236 Sq Ft
  • $214/SF
  • 8 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1984

  5164 Lazy Oaks Dr, Winter Park, FL 32792

  Absolutely charming 2-bedroom, 2.5-bathroom townhome style condo in the heart of Winter Park with a brand new roof! As you enter the front door, you are greeted with the expansive, open design of the first floor that extends all the way through the bonus office room and into the grassy courtyard! The kitchen has been updated with new counter tops, a double sink, and wonderful, little coffee bar

  Jeremy Wood KELLER WILLIAMS HERITAGE REALTY

  5164 Lazy Oaks Dr, Winter Park, FL 32792
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  /18

  Est $218,054 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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  /24

  $625,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 1,842 Sq Ft

  2812 Woodside Ave, Winter Park, FL 32789

  In the heart of the Audubon Park Garden District you will find this updated mid-century modern home on a .17 acre homesite. A brick-paver driveway and front patio provide lots of curb appeal. Stepping inside you are greeted by warm bamboo flooring and tons of natural light thanks to updated windows (2013) throughout. The split floor-plan features 3 bedrooms and 2 bathrooms, both updated with

  Jill Healey KELLER WILLIAMS WINTER PARK

  2812 Woodside Ave, Winter Park, FL 32789
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  /15

  $2,479 per month

  • 3 Beds
  • 2 Baths
  • 1,300 Sq Ft
  • House for Rent

  881 Julian St, Winter Park, FL 32789

  This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,300 square feet, this well-maintained home offers a high standard of rental living, supported by a team that puts residents first. As a Tricon resident, you'll enjoy access to Tricon Vantage — a program designed to support your

  881 Julian St, Winter Park, FL 32789
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  /2

  $65,000 Sold Jul 31, 2025

  • 785 Sq Ft
  • $83/SF
  • 19 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1974

  167 Scottsdale Square Unit E167, Winter Park, FL 32792

  Discover affordable living in the heart of Winter Park at 167 Scottsdale Square, a spacious 1-bedroom, 1-bathroom condo just minutes from Full Sail University, UCF, and Downtown Orlando. This unit features an open floor plan, and access to community amenities. Whether you're a first-time buyer or investor, this location offers unbeatable convenience. Enjoy top-rated schools, nearby shopping, and

  Nevelle Chambers LA ROSA REALTY ORLANDO LLC

  167 Scottsdale Square Unit E167, Winter Park, FL 32792
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  /5

  Est $425,011 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
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  /32

  $160,000

  • 1 Bed
  • 1 Bath
  • 793 Sq Ft

  200 St Andrews Blvd Unit 5, Winter Park, FL 32792

  Excellent location. You can walk to grocery stores, banks, pharmacies in the area. Short drive to Full Sail and Rollins College as well as Park avenue where you have many restaurants, coffee shops, retail.

  Didem Isik Widener PARK AVENUE REALTY LLC

  200 St Andrews Blvd Unit 5, Winter Park, FL 32792
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  /45

  $3,999 per month

  • 3 Beds
  • 2 Baths
  • 1,499 Sq Ft
  • House for Rent

  1681 Walnut Ave, Winter Park, FL 32789

  Fully furnished with dishes and all ! Tastefully decorated !Can be rented unfurnished if needed .Also month to a year lease is ok !Two separate living quarters en suite with private entrance and small fridge and microwave /dining /living area ( or master )Fully renovated this adorable 3 bedroom, 2 bath bungalow home is a rare find in one of Winter Park's most sought-after neighborhoods.Fully

  Natalie Citarelli CITARELLI REALTY GROUP LLC

  1681 Walnut Ave, Winter Park, FL 32789
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  /2

  $699,000 Sold Jul 31, 2025

  • 1,622 Sq Ft
  • $431/SF
  • 14 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  1891 Bryan Ave, Winter Park, FL 32789

  Rare find in Winter Park! This charming one-story pool home offers three bedrooms, two full baths, high ceilings, and an open floor plan—all at an incredible price point. The updated kitchen features gas appliances, a center island, breakfast bar, and a separate beverage fridge. Wood-look tile flooring runs throughout the home for a cohesive, modern feel.The spacious primary suite

  Jennifer King CORCORAN PREMIER REALTY

  1891 Bryan Ave, Winter Park, FL 32789
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  /30

  Est $711,593 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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  /30

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  2774 Banchory Rd, Winter Park, FL 32792

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom block ranch home in Winter Park Pines. Nestled behind a stunning mature oak tree, this home offers comfort, charm, and convenience in one of Central Florida’s most desirable communities. The large driveway leads to a 2-car garage ensuring plenty of space to park for you and your guests. Step onto the covered front porch and into a

  Nicholas Masi KELLER WILLIAMS REALTY AT THE PARKS

  2774 Banchory Rd, Winter Park, FL 32792
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  /2

  $2,780 per month

  • 3 Beds
  • 2 Baths
  • 1,553 Sq Ft
  • House for Rent

  630 N Lakemont Ave, Winter Park, FL 32792

  We are currently making final preparations for this home to be available. We make Pre-Leasing easy! Apply now and, once you’re approved, take this home off the market by paying a Pre-Lease Hold Fee; ask your Leasing Professional for more information. Once the home is made ready, we'll notify you that it's available for touring and for you to accept or decline. If you decline the home, we'll be

  630 N Lakemont Ave, Winter Park, FL 32792
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  /2

  $1,180,000 Sold Jul 31, 2025

  • 4,015 Sq Ft
  • $294/SF
  • 37 Days On Market

  • 4 Beds
  • 5 Baths
  • Built 1995

  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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  /3

  Est $2,165,962 Not Listed For Sale

  150 Whipple Ave, Winter Park, FL 32789

  150 Whipple Ave, Winter Park, FL 32789
• 

  

  /12

  $4,999,000

  • Land
  • 0.48 Acre
  • $10,414,583 per Acre

  503 N Interlachen Ave, Winter Park, FL 32789

  JUST LISTED - RARE 0.48 ACRE VACANT LOT IN DOWNTOWN WINTER PARK - OFFERED AT $4,999,000!!! Zoned R-3, this multi-family, prime piece of land is ready for development. Luxury townhomes or condos, nothing but pure potential. Located near the intersection of N. Interlachen Avenue and Canton Avenue, this parcel is just 1-block to Park Avenue's boutique shops, award-winning restaurants, and esteemed

  Kelly Price KELLY PRICE & COMPANY LLC

  503 N Interlachen Ave, Winter Park, FL 32789
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  /16

  $2,240 per month

  • 3 Beds
  • 2 Baths
  • 1,909 Sq Ft
  • House for Rent

  2717 Amsden Rd, Winter Park, FL 32792

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  2717 Amsden Rd, Winter Park, FL 32792
• 

  /2

  $3,200,000 Sold Jul 31, 2025

  • 5,878 Sq Ft
  • $544/SF
  • 63 Days On Market

  • 6 Beds
  • 5.5 Baths
  • Built 2006

  141 S Phelps Ave, Winter Park, FL 32789

  **This stunning estate just became an unbeatable opportunity--luxury living at a dramatically reduced price! Don't miss your chance to own this exceptional home in the highly coveted Windsong community with access to the gorgeous Winter Park chain of lakes. Prepare to be impressed as you enter this almost 6,000 square foot home adorned with custom high-end features throughout, plus a fabulous

  Donna Bryant COLDWELL BANKER RESIDENTIAL RE

  141 S Phelps Ave, Winter Park, FL 32789
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  /2

  Est $760,825 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 3,094 Sq Ft

  2352 Kestrel Perch Place, Winter Park, FL 32792

  2352 Kestrel Perch Place, Winter Park, FL 32792
• 

  

  /37

  $568,900

  • 3 Beds
  • 2 Baths
  • 1,772 Sq Ft

  1123 Fairway Dr, Winter Park, FL 32792

  Welcome to this beautifully maintained original-owner home nestled along the Winter Pines Golf Course! This property boasts breathtaking golf course views, a newly extended rear patio, and timeless curb appeal with cedar siding that enhances its warm, inviting character. Inside, you'll find all-new flooring throughout, a custom kitchen with solid wood cabinets, and abundant natural light filling

  Tiffany Licata IRON VALLEY REAL ESTATE OSCEOL

  1123 Fairway Dr, Winter Park, FL 32792
• 

  

  /17

  $3,199 per month

  • 4 Beds
  • 2 Baths
  • 1,964 Sq Ft
  • House for Rent

  1821 Carrigan Ave, Winter Park, FL 32789

  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 $3343.90. That covers your base rent, $3199.00 + our required services designed to make your life easier: Air Filter Delivery Fee ($9.95), Internet

  1821 Carrigan Ave, Winter Park, FL 32789
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  /2

  $115,000 Sold Jul 31, 2025

  • 1,090 Sq Ft
  • $106/SF
  • 89 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1974

  7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792

  Whether you're looking for a savvy investment or your next personal home, this spacious 2-bedroom, 2.5-bath townhome checks all the boxes. Ideally located near Full Sail University, UCF, and Valencia College, the property offers unbeatable convenience for students, faculty, and commuters alike.Inside, you'll find durable wood-look vinyl flooring throughout the main level and soft

  Nicole Rader MAINFRAME REAL ESTATE

  7336 Daniel Webster Dr Unit 9, Winter Park, FL 32792
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  /54

  Est $784,207 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 2,894 Sq Ft

  1155 Wildmeadow Run, Winter Park, FL 32792

  1155 Wildmeadow Run, Winter Park, FL 32792
• 

  

  /35

  $750,000

  • 4 Beds
  • 2 Baths
  • 1,968 Sq Ft

  744 Cornwall Rd, Winter Park, FL 32792

  Charming 4-Bedroom Home in Desirable Winter Park PinesWelcome to your new home in the heart of Winter Park Pines! This beautifully maintained 4-bedroom, 2-bath residence offers a perfect blend of classic charm and modern comfort, situated in one of Central Florida’s most sought-after neighborhoods.Step inside to find warm hardwood floors that flow throughout the spacious living areas,

  Tammy Cuddy VERSALIS REALTY POWERED BY SELLSTATE

  744 Cornwall Rd, Winter Park, FL 32792
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  /16

  $2,490 per month

  • 3 Beds
  • 2 Baths
  • 1,448 Sq Ft
  • House for Rent

  7431 Portside Ct, Winter Park, FL 32792

  Welcome to your dream home! Step inside this pet-friendly home featuring modern finishings and a layout designed with functionality in mind. Enjoy the storage space found in the kitchen and closets as well as the spacious living areas and natural light throughout. Enjoy outdoor living in your yard, perfect for gathering, relaxing, or gardening! Take advantage of the incredible location, nestled

  Nico Silva Vanegas MAIN STREET RENEWAL LLC

  7431 Portside Ct, Winter Park, FL 32792
• 

  /2

  $328,000 Sold Jul 31, 2025

  • 1,456 Sq Ft
  • $225/SF
  • 85 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1995

  156 Oak Grove Rd, Winter Park, FL 32789

  Welcome home to this beautifully maintained 3-bedroom, 2.5-bath residence in the highly desirable Winter Park Oaks community, featuring 1,500 sq. ft. of inviting living space ideal for both comfort and entertaining. The thoughtfully designed two-story layout includes an open-concept main level with a spacious kitchen flowing effortlessly into a bright family room, convenient downstairs half bath,

  Serge Osaulenko EVERLANE REALTY LLC

  156 Oak Grove Rd, Winter Park, FL 32789
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  /67

  Est $1,332,723 Not Listed For Sale

  • 7 Beds
  • 5 Baths
  • 5,111 Sq Ft

  1464 Via Sangro Place, Winter Park, FL 32792

  1464 Via Sangro Place, Winter Park, FL 32792

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