202

Winter Park, FL Homes for Sale with Pool

Section Image Section Image
  • /42

    $440,000

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

    2224 Shadowland Loop, Winter Park, FL 32792

    **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.** Nestled in the heart of Winter Park, 2224 Shadowland Loop offers a beautiful blend of comfort, style, and low-maintenance living in this spacious 3-bedroom, 3-bathroom townhouse. The interior features an inviting open layout

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 450-7733

    2224 Shadowland Loop, Winter Park, FL 32792
  • /35

    $260,000

    • 2 Beds
    • 1 Bath
    • 804 Sq Ft

    151 N Orlando Ave Unit 101, Winter Park, FL 32789

    Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled on the ground floor of the Lake Killarney Condominiums, Unit 101 offers a seamless blend of comfort, style, and lakeside living. Bright & open layout that flows from the living space into a modern kitchen with a large center island — perfect for entertaining or casual family meals. Granite countertops,

    Agent Photo

    Elizabeth Fowler

    THE FLORIDA PROPERTY SHOP SALE

    (321) 463-4625

    151 N Orlando Ave Unit 101, Winter Park, FL 32789
  • /55

    $574,900

    • 4 Beds
    • 2 Baths
    • 1,948 Sq Ft

    2814 Sheriff Way, Winter Park, FL 32792

    Welcome to 2814 Sheriff Way, an exceptional residence nestled in the vibrant neighborhood of Winter Park Pines. This remarkable home combines comfort and elegance, offering a tranquil lifestyle with unparalleled convenience. Spanning 1,948 square feet, this property boasts four generously sized bedrooms and two bathrooms (both showers renovated 5/25) perfect for family living or entertaining

    Agent Photo

    Angela Carney

    CORCORAN PREMIER REALTY

    (321) 220-9015

    2814 Sheriff Way, Winter Park, FL 32792
  • /36

    $279,900

    • 2 Beds
    • 2 Baths
    • 1,495 Sq Ft

    2501 Tahoe Cir Unit 32501, Winter Park, FL 32792

    Welcome home to this spacious two-story Winter Park condo located in the sought-after Cedarwood Village community. Tucked away among mature landscaping yet close to everything, this residence offers a comfortable blend of privacy, architectural character, and convenience in a prime Central Florida location.The main living area features soaring 16.5-foot vaulted ceilings, a wood-burning

    Agent Photo

    Sarah Doyer

    COLDWELL BANKER REALTY

    (321) 510-4129

    2501 Tahoe Cir Unit 32501, Winter Park, FL 32792
  • /33

    $200,000

    • 2 Beds
    • 2 Baths
    • 953 Sq Ft

    225 Lewfield Cir, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. **This property qualifies for a closing cost credit up to $3,300 through the Seller’s preferred lender.** Welcome to this updated 2-bedroom, 2-bath first-floor condo in the heart of Winter Park. Tucked away at the back right corner of the building, this bright unit features hardwood floors throughout and an open living room with sliding glass doors

    Agent Photo

    Thomas Nickley

    KELLER WILLIAMS REALTY AT THE PARKS

    (321) 237-3113

    225 Lewfield Cir, Winter Park, FL 32792
  • /19

    $225,000

    • 3 Beds
    • 2 Baths
    • 1,230 Sq Ft

    7706 Country Place Unit A8, Winter Park, FL 32792

    Great investment opportunity. Ideal for a growing family or investor. Well established neighborhood of Goldenrod Villas, 3 bedroom, 2 full bathrooms, 1,230 square feet of living area. Exterior of the home is concrete block and stucco. The eat-in-kitchen sits in the heart of the home which creates a warm and social atmosphere. Nice covered patio with back yard great for relaxing and entertaining

    Agent Photo

    Carmen Vazquez

    REALTY TECH INC

    (321) 339-0107

    7706 Country Place Unit A8, Winter Park, FL 32792
  • /78

    $1,479,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,459 Sq Ft

    102 Bell Place, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Dreams Do Come True! This spectacular brand-new 2025 block construction home, crafted with steel framing instead of wood, combines modern luxury with timeless design in one of Winter Park’s up incoming desirable areas—just moments from Interlachen Country Club and the Lakemont Heights neighborhood an NO HOA!Step through the double-door entry

    Agent Photo

    Freddie Crespo

    INVESTOR'S REAL ESTATE LLC

    (321) 490-4832

    102 Bell Place, Winter Park, FL 32792
  • /48

    $295,000

    • 3 Beds
    • 2 Baths
    • 1,291 Sq Ft

    1873 Casselwood St, Winter Park, FL 32792

    Welcome to this enchanting 3-Bedroom, 2-Bathroom townhouse in Winter Park! Walk into an open floor plan giving you comfort and that homey feeling with a modern touch. A gorgeous kitchen area with a granite countertop, that flows with the home and is perfect for hosting. Tile flooring throughout, this home is move in ready!! Coming with a one car garage that was converted into a bonus space that

    Devin Costley ERA GRIZZARD REAL ESTATE

    1873 Casselwood St, Winter Park, FL 32792
  • /66

    $2,395,000

    • 4 Beds
    • 5.5 Baths
    • 4,392 Sq Ft

    1760 Legion Dr, Winter Park, FL 32789

    Winter Park 1964 Charmer! This wonderful ranch is located just minutes to Downtown Orlando as well as Park Ave. With over 4300 sq ft of living space, this, 4 bed/5.5 bath home is in the prime location. Upon entering you'll notice just how light and bright this home shows, to your right you will find a home office space. Rich dark wood, custom cabinetry and dramatic lighting provide the perfect

    Steven Looper CHARLES RUTENBERG REALTY ORLANDO

    1760 Legion Dr, Winter Park, FL 32789
  • /54

    $424,900

    • 3 Beds
    • 2 Baths
    • 2,083 Sq Ft

    1367 Tierra Cir, Winter Park, FL 32792

    Located in the highly desirable Casa Aloma neighborhood of Winter Park, this updated 3-bedroom, 2-bath, 2,083 sq ft home offers Spanish architectural combined with thoughtful modern improvements. Built in 1969, the home features concrete block construction on a concrete foundation, providing durability and peace of mind. Situated on a corner lot with updated landscaping, the property offers

    Brian Bauer SOUTHERN LAND & HOMES

    1367 Tierra Cir, Winter Park, FL 32792
  • /39

    $195,000

    • 2 Beds
    • 2 Baths
    • 1,105 Sq Ft

    2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792

    Discover a charming 2nd-story condo nestled in the desirable Parkview Village community of Winter Park. This spacious home features two bedrooms and two bathrooms across 1,105 square feet of thoughtfully designed living space. The interior boasts large rooms, providing ample space for comfort and versatility. Admire the vaulted ceilings that enhance the open and airy atmosphere, while the

    Donna Layton CENTURY 21 EDGE

    2924 Antique Oaks Cir Unit 46, Winter Park, FL 32792
  • /43

    $3,295,000

    • 5 Beds
    • 5.5 Baths
    • 4,955 Sq Ft

    1761 Legion Dr, Winter Park, FL 32789

    One of the most coveted neighborhoods in all of Winter Park! This custom-built 5-bedroom, 5.5-bath residence was completed in 2017 and first sold in 2018. Lovingly maintained by the original owner and elevated with high-end designer finishes, the home showcases the impeccable vision of renowned designer Ted Maines, who reimagined much of the interior with timeless sophistication. Perfectly

    Brian Scanlon SCANLON REALTY GROUP LLC

    1761 Legion Dr, Winter Park, FL 32789
  • /66

    $1,350,000

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

    3711 Vinsetta Ct, Winter Park, FL 32792

    Elevate your lifestyle in the prestigious Lakeside Estates, a private gated Winter Park community anchored by Garden Lake. In a quiet cul-de-sac, on a wrapping corner lot on over 1/3 of an acre and only a short distance to the playground making it easy. A six-bedroom, four-bath home sprawls over 4,200 square feet with back of the house opening to a covered porch with a generously sized saltwater

    Alison Mosley PREMIER SOTHEBY'S INTL. REALTY

    3711 Vinsetta Ct, Winter Park, FL 32792
  • /23

    $255,000

    • 2 Beds
    • 2 Baths
    • 1,068 Sq Ft

    7707 Country Place Unit 4, Winter Park, FL 32792

    Beautifully updated 2BD/2BA single-story condo in peaceful Goldenrod Villas, Winter Park. Enjoy an insulated, screen-enclosed lanai with its own AC unit, plus a brand-new backyard deck and private patio. Both bedrooms offer ensuite baths with updated vanities and large walk-in closets. NEW luxury vinyl plank flooring throughout. Extended kitchen with added cabinets and bar seating. Laundry room

    Stephanie Sanchez WEICHERT REALTORS HALLMARK PRO

    7707 Country Place Unit 4, Winter Park, FL 32792
  • /53

    $4,595,000

    • 4 Beds
    • 5 Baths
    • 3,181 Sq Ft

    1336 College Point, Winter Park, FL 32789

    Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1336 College Point, Winter Park, FL 32789
  • /54

    $1,990,000

    • 4 Beds
    • 3.5 Baths
    • 3,307 Sq Ft

    2614 Parkland Dr, Winter Park, FL 32789

    The only home priced under $2MM that has over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space,

    Ryan Gaston JW GASTON LLC

    2614 Parkland Dr, Winter Park, FL 32789
  • /35

    $750,000

    • 3 Beds
    • 2 Baths
    • 1,827 Sq Ft

    676 Dunblane Dr, Winter Park, FL 32792

    This meticulously maintained POOL HOME located in the highly desirable Kenilworth Shores community could be YOURS! 3 Beds | 2 Baths | Bonus Room | This classic ranch-style residence offers a spacious and functional layout with three well-appointed bedrooms, two full bathrooms, a formal living room, dining area, and a bright breakfast nook. An additional bonus room provides flexible use — ideal as

    Emma Kaplan BALDWIN PARK REALTY LLC

    676 Dunblane Dr, Winter Park, FL 32792
  • /76

    $6,895,000 New Construction

    • 5 Beds
    • 6.5 Baths
    • 5,939 Sq Ft

    550 Palmer Ave, Winter Park, FL 32789

    Exquisite new construction in the Heart of Winter Park perfectly positioned on an oversized lot just steps from Park Avenue’s renowned shops, fine dining, and the iconic Winter Park 9-hole golf course, this extraordinary custom residence is a showcase of timeless design and modern luxury. Conceived by acclaimed architect Dan Delong of Origins Residential Design and brought to life by Sean Wulff

    John McDade FANNIE HILLMAN & ASSOCIATES

    550 Palmer Ave, Winter Park, FL 32789
  • /11

    $128,500

    • 2 Beds
    • 2 Baths
    • 1,072 Sq Ft

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792

    Priced to sell! This 2 bedroom 2 bathroom condo located in the highly sought after Winter Park area is the perfect opportunity for an investor or a first time buyer. This unit has new luxury vinyl plank flooring throughout, recently upgraded kitchen cabinets, huge living room area and very spacious bedrooms. Located on the 2nd floor, and within steps of the community pool and laundry facility.

    Cristina Burgos REALSOURCE PROPERTY MANGNT LLC

    1000 S Semoran Blvd Unit 512, Winter Park, FL 32792
  • /88

    $8,500,000

    • 5 Beds
    • 6 Baths
    • 6,502 Sq Ft

    1112 Preserve Point Dr, Winter Park, FL 32789

    Presenting 1112 Preserve Point Drive, Winter Park, FL! Offered at $8,500,000 this very rare and private, nearly 2-acre lakefront estate, is absolutely gorgeous and is available for the first time! Custom built by Phil Kean Design Group and located within Windsong's Preserve Point, this extraordinary Lake Berry home has it all including 1.97 acres of land adjacent to the historic Genius Preserve

    Kelly Price KELLY PRICE & COMPANY LLC

    1112 Preserve Point Dr, Winter Park, FL 32789
  • /6

    $99,000

    • Studio
    • 1 Bath
    • 537 Sq Ft

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792

    Attention investors! Take a look at this great opportunity to purchase a Cozy Condo located in Winter Park, FL. This studio condo features beautiful tile floors and lots of closet space. First-floor unit with open patio. Minutes away from Downtown Winter Park, expressway, downtown Orlando, Full Sail, and the University of Central Florida. This community offers a pool, tennis court, and clubhouse.

    Lynda Cheros OAKSTRAND REALTY

    3069 Aaron Burr Ave Unit 1, Winter Park, FL 32792
  • /5

    $5,000

    • 3 Beds
    • 2 Baths
    • 1,464 Sq Ft

    1872 Linden Rd, Winter Park, FL 32792

    Foreclosure Auction Ends March 17, 2026 at 11:00 AM EST. Comfortable 3-bedroom, 2-bath home offering a practical layout and well-proportioned living spaces in a desirable Winter Park neighborhood. The list price is the opening bid for the online auction. Sold As-is. Explore more details and submit your bid through Federa Home App.

    Jamie Boone Jamie L Boone LLC

    1872 Linden Rd, Winter Park, FL 32792
  • /27

    $539,000

    • 4 Beds
    • 3 Baths
    • 1,826 Sq Ft

    731 Bongart Rd, Winter Park, FL 32792

    Experience luxury living in this stunning, remodeled single-family home located in the heart of Winter Park. This spectacular residence features four spacious bedrooms and three modern bathrooms, boasting sleek laminate flooring throughout. The chef-inspired kitchen comes fully equipped with premium stainless steel appliances, while the massive backyard and sparkling pool provide an ideal setting

    Maria Gomez Arevalo MY REALTY GROUP, LLC.

    731 Bongart Rd, Winter Park, FL 32792
  • /6

    $7,150,000 New Construction

    • 12,500 Sq Ft

    2412 Chantilly Ave, Winter Park, FL 32789

    This exclusive trifecta investment opportunity combines luxury real estate, dual-lane income potential, and powerful tax advantages—all in one of the fastest-growing markets in the country. Investors can capitalize on long-term rental cap rates around 8% or tap into short-term rental returns reaching upward of 13%, while benefiting from substantial first-year cost-segregation deductions of

    Tab Bish LLC REAL BROKER, LLC

    2412 Chantilly Ave, Winter Park, FL 32789
  • /43

    $175,000

    • 1 Bed
    • 1 Bath
    • 793 Sq Ft

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Experience elevated living in this beautifully appointed 1-bedroom, 1-bath residence located on the second floor in the heart of Winter Park, Florida. The home showcases elegant wood-look tile flooring throughout, creating a seamless, upscale aesthetic with both style and durability.The primary bedroom is enhanced with classic plantation

    Eric Zimmerman RE/MAX ADVANTAGE

    200 Saint Andrews Blvd Unit 315, Winter Park, FL 32792
  • /25

    $189,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 122, Winter Park, FL 32789

    Welcome home to this updated 1-bedroom 1-bathroom GROUND FLOOR condo, ideally positioned toward the desirable rear of the sought-after Lakeside Manor community. The move-in-ready residence features a spacious, open floor plan enhanced by ceramic tile throughout, elegant crown molding and a thoughtfully updated kitchen complete with modern countertops, soft-close cabinetry, and newer

    Andrea Aylett-Hosch PINEAPPLE PLACE REALTY, LLC

    2500 Lee Rd Unit 122, Winter Park, FL 32789
  • /50

    $635,000

    • 3 Beds
    • 2 Baths
    • 1,785 Sq Ft

    2708 Lion Heart Rd, Winter Park, FL 32792

    Welcome to 2407 Lion Heart, Winter Park — where timeless elegance meets modern comfort. Nestled in one of Winter Park’s most desirable communities, this fully renovated 3-bedroom, 2-bath residence offers the perfect blend of sophistication, functionality, and peaceful living. Step inside and experience 1,785 square feet of thoughtfully designed open-concept living space, highlighted by wide-plank

    Navid Rokh EQUITYPRO LLC

    2708 Lion Heart Rd, Winter Park, FL 32792
  • /28

    $145,000

    • 1 Bed
    • 1 Bath
    • 645 Sq Ft

    2500 Lee Rd Unit 243, Winter Park, FL 32789

    Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community for its location and tranquil setting on Lake Killarney. Add to that the brand new air conditioning system (2025), hot water heater (2025) and fresh paint throughout (2025) and you'll see why this unit is for you. Step into the unit through the brand new front door (2025) and you are in the generous living

    Sue Gilman KELLER WILLIAMS WINTER PARK

    2500 Lee Rd Unit 243, Winter Park, FL 32789
  • /36

    $424,000

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

    2834 Bright Bird Ln, Winter Park, FL 32792

    Preferred Lender rate Incentives available. This beautifully maintained 3-bedroom, 2.5-bath townhome with a one-car garage, located in a newly gated community that offers comfort, style, and convenience. The home features ambient high-hat lighting throughout, creating a warm and modern atmosphere. The spacious kitchen is ideal for everyday living and entertaining, while the open living area is

    Irene Navarro LIFESTYLE INTERNATIONAL REALTY

    2834 Bright Bird Ln, Winter Park, FL 32792
  • /20

    $220,000

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

    3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792

    This unit was restored, with new kitchen cabinets, new ceramic tile in kitchen, living room, dining room and 2ndbathroom. It has been impeccably maintained. Walking distance from Full Sail and only 6.9 miles to UCF.Spacious bedrooms and baths and very comfortable layout. Lovely screened patio off living room. Complexoffers pool, and club house. A/C unit is brand new, installed on

    Manny Celi YOUNG REAL ESTATE

    3038 Antique Oaks Cir Unit 166, Winter Park, FL 32792
  • /3

    $1,950,000 New Construction

    • 4 Beds
    • 4 Baths
    • 2,810 Sq Ft

    2501 Lafayette Ave, Winter Park, FL 32789

    Under Construction. Exceptional design meets refined luxury in this brand-new architectural masterpiece by DaVinci. This 4 bedroom, 4 bath home offers over 2,800 square feet of bright, open living space designed for both comfort and functionality. Enter through your custom pivot front door into the foyer leading to your main living area featuring sliding glass walls for indoor-outdoor living.

    Tab Bish LLC REAL BROKER, LLC

    2501 Lafayette Ave, Winter Park, FL 32789
  • /21

    $259,000

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

    1500 Gay Rd Unit 18A, Winter Park, FL 32789

    Lakefront Community on beautiful Lake Killarney. 2 Bedroom/2 Bath First Floor Unit with Courtyard And Lake Views. Lovingly updated and meticulously maintained. Kitchen has raised ceilings, Maple Cabinets and Granite Counters. Dining Room has matching Cabinets and Counters with pull-out Drawers for additional Storage. Tile Floors in Living Areas. New Carpets in both Bedrooms. Windows and Sliding

    Janice Erickson REALCOM REAL ESTATE SERVICES INC

    1500 Gay Rd Unit 18A, Winter Park, FL 32789
  • /17

    $195,000

    • 1 Bed
    • 1 Bath
    • 732 Sq Ft

    1500 Gay Rd Unit 5, Winter Park, FL 32789

    Welcome to Chateaux du Lac, a lakefront community in the heart of Winter Park, FL, offering an active and convenient lifestyle. Residents enjoy an impressive array of amenities including a heated community pool, clubhouse, lakefront community deck, BBQ area, resident-only boat ramp, community laundry facilities, and two on-site saunas. This second-floor one-bedroom, one-bath apartment features

    Jacob Hara TRANSCEND REALTY

    1500 Gay Rd Unit 5, Winter Park, FL 32789
  • /65

    $2,295,000

    • 5 Beds
    • 3.5 Baths
    • 3,691 Sq Ft

    1885 Temple Dr, Winter Park, FL 32789

    NEW 2026 Black Steel doors windows with low e-dual pane glass ($150k value!). Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most

    Jennifer Sloan COMPASS FLORIDA LLC

    1885 Temple Dr, Winter Park, FL 32789
  • /25

    $219,900

    • 2 Beds
    • 2 Baths
    • 1,058 Sq Ft

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792

    Charming Updated Home in Prime Winter Park Location Welcome to this beautifully updated home located in the highly desirable area of Winter Park. Combining comfort, style, and convenience, this property offers a thoughtfully designed open floor plan that creates a seamless flow between the main living spaces, making it ideal for both everyday living and entertaining. The home features two

    Angelica Diaz Bajo WRA BUSINESS & REAL ESTATE

    4858 Tangerine Ave Unit 4858, Winter Park, FL 32792
  • /33

    $150,000

    • 1 Bed
    • 1 Bath
    • 749 Sq Ft

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792

    Welcome to this bright and cozy 1-bedroom, 1-bathroom corner unit located in the highly desirable Winter Park area of Orlando. This well-maintained condo features ceramic tile flooring throughout, a spacious walk-in closet in the master bedroom, a laundry closet with washer and dryer included, and modern light fixtures. Enjoy the outdoors on your very nice private balcony, and take advantage of

    SANTIAGO SILVA THE PAMPAS REAL ESTATE GROUP, LLC.

    2948 Antique Oaks Cir Unit 94, Winter Park, FL 32792
  • /52

    $180,000

    • 1 Bed
    • 1 Bath
    • 727 Sq Ft

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792

    This isn’t your average condo. It’s professionally updated with large rooms and more closet space than you’ll know what to do with. There’s even a washer and dryer right in the unit (no more laundry runs!), newer appliances, and parking right outside your door. On a scale from 1 to 10, this place is easily a TWENTY! Seriously, no expense was spared to make it super comfortable. You’ll love the

    Jonathan Lacko WINTER PARK REAL ESTATE CO LLC

    200 Saint Andrews Blvd Unit 705, Winter Park, FL 32792
  • /27

    $145,000

    • 2 Beds
    • 2.5 Baths
    • 1,090 Sq Ft

    3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792

    Townhouse 2 bedroom 2.5 bath, both bathrooms on the second floor are remodeled. The Townhome is rent $1,600. The unit is located in Winter Park Area and is close to the shopping and dining. It is also close to public transportation. HOME GUARANTY OF AMERICA HWA 13 MONTH INCLUDED.

    Daiana Garcia Medrano LA ROSA REALTY ORLANDO LLC

    3021 Aaron Burr Ave Unit 3, Winter Park, FL 32792
  • /32

    $144,000

    • 1 Bed
    • 1 Bath
    • 678 Sq Ft

    291 Lewfield Cir Unit 291, Winter Park, FL 32792

    Enjoy easy living in this cozy, open-concept first-floor condo located in a desirable Winter Park community. Step out onto your newly screened-in patio and take in the peaceful, park-like setting — a relaxing extension of your living space and the perfect spot for morning coffee or evening unwinding. Recent 2025 improvements include a new A/C system, water heater, freshly painted interior, new

    Barbara Coy WATSON REALTY CORP

    291 Lewfield Cir Unit 291, Winter Park, FL 32792
  • /75

    $3,055,000

    • 4 Beds
    • 4.5 Baths
    • 4,129 Sq Ft

    151 Oakwood Way, Winter Park, FL 32789

    Welcome to 151 Oakwood Way. This is a rare Winter Park showpiece by LunDev Custom Homes, tucked on a quiet, tree-lined street in the heart of Winter Park. This newer luxury pool home delivers the perfect blend of timeless architecture and modern comfort, pairing clean transitional design with warm, high-end selections and true Florida indoor/outdoor living. Inside, a bright open-concept floor

    Matthew Burks CORCORAN PREMIER REALTY

    151 Oakwood Way, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 6

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$489,510
Median Single Family Sale Price
$599,900
Median Townhouse Sale Price
$459,000
Median 2 Bedroom Sale Price
$206,259
Median 1 Bedroom Sale Price
$155,000
Average Price Per Sq Ft
$371
Number of Homes for Sale
284
Last 12 months Home Sales
1,008
Months of Supply
3.40
Median List Price
$525,000
Median Change From 1st List Price
5%
Median Home Sale Price YoY Change
3%
How to Buy a Home How to Finance a Home How to Sell a Home