227

Winter Park, FL Homes for Sale with Garage

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  • /89

    $1,000,000

    • 4 Beds
    • 3.5 Baths
    • 3,074 Sq Ft

    4107 Gabriella Ln, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. Do you have a vision? Do you love Nature? Welcome to this Exceptional Bear Gully Lakefront Retreat – A Rare Blend of Privacy and Natural Beauty! Refurbish the house as it is, or start new on this amazing rare natural Florida lakefront ground. Tucked away on the serene shores of Bear Gully Lake, this one-of-a-kind property presents a rare

    Agent Photo

    Barrett Spray

    KELLER WILLIAMS ADVANTAGE REALTY

    (321) 382-1061

    4107 Gabriella Ln, Winter Park, FL 32792
  • /42

    $875,000

    • 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

    Agent Photo

    Rod Chevalier

    BHHS FLORIDA REALTY

    (321) 339-2639

    1090 Wildmeadow Run, Winter Park, FL 32792
  • /44

    $729,000

    • 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

    Agent Photo

    Khozaif Merali

    CHARLES RUTENBERG REALTY ORLANDO

    (321) 490-4706

    607 Dunblane Dr, Winter Park, FL 32792
  • /42

    $765,000

    • 3 Beds
    • 2 Baths
    • 2,134 Sq Ft

    2418 Whitehall Cir, Winter Park, FL 32792

    One or more photo(s) has been virtually staged. MAJOR PRICE REDUCTION! MOTIVATED SELLER! Don't miss out!!! A true GEM located in the highly desirable Brookshire Heights, presenting this FULLY REMODELED spacious single-story property in the heart of WINTER PARK. Showcasing a new meticulously designed floorplan, this property has also recently been EXTENDED by a total approx. 1,040 sqft. Exuding

    Agent Photo

    Alice Anne Jackson

    CORCORAN PREMIER REALTY

    (321) 599-7240

    2418 Whitehall Cir, Winter Park, FL 32792
  • /100

    $8,500,000 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

    Agent Photo

    Prescilla Vazquez

    PV LUXURY GROUP PA

    (321) 478-2671

    2661 Vía Tuscany, Winter Park, FL 32789
  • /19

    $529,900

    • 3 Beds
    • 2 Baths
    • 2,254 Sq Ft

    7682 Glenmoor Ln, Winter Park, FL 32792

    Welcome to 7682 Glenmoor Lane – Located in the established community of Glenmoor, zoned for Winter Park HS, Maitland Middle and Lakemont Elementary.This beautifully renovated Winter Park gem is situated on a generous 0.26-acre lot, this stunning single-family home blends timeless style with modern updates throughout.Step inside to discover custom tile flooring, solid wood cabinetry in

    Bob Holston, Jr HOLSTON PROPERTIES & DEV., INC

    7682 Glenmoor Ln, Winter Park, FL 32792
  • /29

    $365,000

    • 3 Beds
    • 2 Baths
    • 1,467 Sq Ft

    2006 Ponderosa Ave, Winter Park, FL 32792

    Pure Potential in Winter Park’s Eastbrook Community! Renovate or move-in, this is a great opportunity for an investor or homebuyer. Spacious 1,467 SF home with 3 bedrooms, 2 full baths, living & family room + a home office/den which could easily be converted into a 4th bedroom. New carpet in each bedroom. Fresh paint throughout. Attached 2-car garage with laundry. Custom built shed has plenty of

    Kelly Price KELLY PRICE & COMPANY LLC

    2006 Ponderosa Ave, Winter Park, FL 32792
  • /41

    $460,000

    • 3 Beds
    • 2 Baths
    • 1,263 Sq Ft

    5331 Oak Ct, Winter Park, FL 32792

    Welcome to Wrenwood Heights Community!! Very well Maintain Pool Home on CUL-DE-SAC LOT!! Great community with no HOA. House located on spacious large lot 0.31 Acre. House features Open Concept with 3 bedroom and 2 bathroom! New Roff 2024. Pool was resurfaced in 2025. Fully Fenced Backyard with upgraded Paver patio and mature landscaping and Fruit trees. Community located in Winter Park close to

    Nataliya Voroshylo CHARLES RUTENBERG REALTY ORLANDO

    5331 Oak Ct, Winter Park, FL 32792
  • /33

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    1471 Broad Wing Ln, Winter Park, FL 32792

    1% lender credit (based on loan amount) toward closing costs or rate buy-down with seller’s preferred lender. Ask for details! Step into comfort and style in this beautifully maintained townhome, built in 2020 and thoughtfully designed for modern living. The open-concept layout features granite countertops, sleek finishes, and an oversized, screened-in lanai that opens to a tranquil wooded

    Kathryn West EXP REALTY LLC

    1471 Broad Wing Ln, Winter Park, FL 32792
  • /54

    $3,544,999

    • 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
  • /80

    $1,210,000

    • 4 Beds
    • 3.5 Baths
    • 3,321 Sq Ft

    4048 Gilder Rose Place, Winter Park, FL 32792

    Welcome to 4048 Gilder Rose Pl, an impressive four-bedroom, three and a half bathroom residence spanning over 3,300 square feet, located in Winter Park at Bear Gully Pointe, a gated community featuring a spring fed 137 acre lake. This beautifully updated home perfectly balances modern style with practical living, offering an inviting retreat for those seeking both comfort, sophistication and

    Abby Greenberg COMPASS FLORIDA LLC

    4048 Gilder Rose Place, Winter Park, FL 32792
  • /77

    $2,900,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 7 Baths
    • 5,416 Sq Ft

    1401 Green Cove Rd, Winter Park, FL 32789

    This award-winning Tuscan Mediterranean residence seamlessly blends timeless architecture with a light-filled, open interior, situated on a spacious corner lot just moments from Park Avenue. From the moment you step into the grand foyer—with its graceful circular staircase, custom tile work, and rich wood floors—it's clear that every detail of this home was crafted with care.The heart of

    Terry Yonker BUCKEYE REALTY LLC

    1401 Green Cove Rd, Winter Park, FL 32789
  • /66

    $1,249,000

    • 3 Beds
    • 2.5 Baths
    • 1,993 Sq Ft

    2525 Venetian Way, Winter Park, FL 32789

    Modern Midcentury Retreat with Luxe Upgrades & Private Community Lake Access This meticulously renovated 3-bed, 2.5-bath midcentury home blends timeless design with high-end contemporary finishes. Reimagined in 2021, it features an open floorplan highlighted by terrazzo flooring, quartz accent walls, and a cozy family room with bamboo floor and a gas fireplace. The sleek, chef-inspired kitchen

    Kimberly Slinger KELLY PRICE & COMPANY LLC

    2525 Venetian Way, Winter Park, FL 32789
  • /37

    $950,000

    • 3 Beds
    • 3.5 Baths
    • 2,116 Sq Ft

    1251 Arlington Place, Winter Park, FL 32789

    STUNNING WINTER PARK TOWNHOME - NO HOA, DESIGNER KITCHEN, PRIVATE BACKYARD OASISWelcome to this rare gem in the heart of Winter Park — a beautifully updated 3-bedroom, 3.5-bath townhome that lives like a single-family home WITH NO HOA! From the moment you walk in, you’ll be impressed by 20-FOOT CEILINGS in the foyer and family room, elegant hardwood floors, and OVERSIZED 8.5-FOOT DOORS

    Brad Barnett ANNE ROGERS REALTY GROUP INC

    1251 Arlington Place, Winter Park, FL 32789
  • /85

    $1,590,000

    • 5 Beds
    • 4.5 Baths
    • 5,329 Sq Ft

    8041 Lake Waunatta Dr, Winter Park, FL 32792

    Modern Lakefront Dream home NOW AVAILABLE! Nestled in the peaceful Lake Waunatta Woods neighborhood, this stunning renovated lakefront estate seamlessly blends modern style with effortless luxury. With over 5,300 square feet, five spacious bedrooms, and breathtaking panoramic views of Lake Waunatta from nearly every room, this one-of-a-kind property offers the ultimate waterfront lifestyle.

    Kathryn Stelljes KELLER WILLIAMS REALTY AT THE PARKS

    8041 Lake Waunatta Dr, Winter Park, FL 32792
  • /48

    $2,150,000

    • 5 Beds
    • 4.5 Baths
    • 3,851 Sq Ft

    1560 Woodland Ave, Winter Park, FL 32789

    You have arrived to 1560 Woodland Avenue, a beautiful home in a prime location inside the Winter Park municipality, situated on a peaceful brick-paved street. There are five bedrooms and four and a half bathrooms spread out over 3,800 square feet in this stunning property. Featuring a welcoming pool and relaxing spa. A separate suite with its own entrance is available for use by the mother-in-law

    Manny Alvarez LOKATION

    1560 Woodland Ave, Winter Park, FL 32789
  • /44

    $440,000

    • 4 Beds
    • 2 Baths
    • 1,821 Sq Ft

    2829 Aloma Ave, Winter Park, FL 32792

    Rare Opportunity in Highly Sought-After Winter Park!Don’t miss your chance to own this fantastic 1960s gem in one of Winter Park’s most desirable neighborhoods just minutes to Cady Way Trail, and tons of Dining and shopping options! SELLER WILL CONTRIBUTE 10K to your closing costs.. AND ...LISTED WELL BELOW APPRAISED VALUE ! Known for its top-rated schools and unbeatable location as well , this

    Cassie Lamoureux KELLER WILLIAMS CLASSIC

    2829 Aloma Ave, Winter Park, FL 32792
  • /59

    $1,575,000

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft

    690 Osceola Ave Unit 604, Winter Park, FL 32789

    Gorgeous Lakefront 2-Story Winter Park Penthouse, corner builder’s unit with panoramic views of Lake Virginia from almost every room and its expansive full-width balcony. Welcome to Lakefront Luxury Living in the heart of Winter Park. This extraordinary Penthouse residence on the Chain of Lakes perfectly captures the essence of opulent Florida living. The 2-story lakefront home offers an

    Larry Slung COLDWELL BANKER RESIDENTIAL RE

    690 Osceola Ave Unit 604, Winter Park, FL 32789
  • /35

    $784,000 Open Sat 11AM - 2PM

    • 5 Beds
    • 4 Baths
    • 2,866 Sq Ft

    5618 Winterbrook Way, Winter Park, FL 32792

    This stunning 5-bed, 4-bath home in the exclusive gated WINTERBROOK community is move in ready and ready for you to enjoy. Built in 2020 by Pulte Homes, this like new energy-efficient home offers luxury wood-look tile, wood beams, a 2 car garage with epoxy floors and a beautifully landscaped backyard. The gourmet kitchen features quartzite countertops, a gas cooktop, upgraded sink, and large

    Elizabeth Binder REDFIN CORPORATION

    5618 Winterbrook Way, Winter Park, FL 32792
  • /31

    $1,490,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 2,838 Sq Ft

    2408 Lafayette Ave, Winter Park, FL 32789

    This brand new custom home is nestled in an up-and-coming neighborhood in Winter Park. This stunning home redefines modern living. Designed with an open floor plan, it seamlessly blends spaces to create a harmonious flow, perfect for both entertaining and everyday life. The abundance of windows bathes the interiors in natural light, creating a bright and airy ambiance. The office/study is set

    Matthew Burks CORCORAN PREMIER REALTY

    2408 Lafayette Ave, Winter Park, FL 32789
  • /41

    $650,000

    • 3 Beds
    • 2 Baths
    • 1,412 Sq Ft

    4281 Anissa Ave Unit 303, Orlando, FL 32814

    Beautifully maintained third-floor condo filled with natural light from tall windows and french doors. From the spacious wrap-around porch, enjoy peaceful sunrises and sunsets, watch rocket launches, and take in the 4th of July fireworks without leaving home. This three-bedroom, two-bathroom home features an open-concept layout with tile flooring in the main living areas and laminate floors in

    Louise Mailloux BHHS FLORIDA REALTY

    4281 Anissa Ave Unit 303, Orlando, FL 32814
  • /32

    $899,000

    • 5 Beds
    • 4 Baths
    • 3,424 Sq Ft

    2604 Marble Ave, Orlando, FL 32803

    Stunning 5 BEDROOM POOL HOME in the Heart of AUDUBON PARK GARDEN DISTRICT. Welcome to 2604 Marble Avenue — a beautifully appointed 5-bedroom, 4-bathroom home offering 3,424 SQUARE FEET of stylish living space in one of Orlando's most desirable neighborhoods. Zoned for top-rated AUDUBON PARK K-8 and WINTER PARK HIGH SCHOOL, this home combines location, comfort, and exceptional versatility.

    Brian Spain LAKESIDE REALTY

    2604 Marble Ave, Orlando, FL 32803
  • /33

    $2,495,000

    • 3 Beds
    • 3.5 Baths
    • 3,155 Sq Ft

    1554 Lake Knowles Cir, Winter Park, FL 32789

    Exuding timeless charm and Southern elegance, this gorgeous Charleston-style residence sits on a large lot overlooking the tranquil waters of Lake Knowles. Framed by a picturesque brick street lined with beautiful homes, the property boasts striking curb appeal, a 32-foot second-story porch with breathtaking sunset views, and classic architectural details that invite you in at every turn. A

    Mick Night PREMIER SOTHEBY'S INTL. REALTY

    1554 Lake Knowles Cir, Winter Park, FL 32789
  • /25

    $1,150,000

    • 5 Beds
    • 3 Baths
    • 2,813 Sq Ft

    233 Hampden Place, Winter Park, FL 32789

    Vintage original 5-Bed, 3-Bath pool home with new roof on an estate-size lot adorned with mature landscaping and breathtaking views that overlook a natural wooded area in desirable Virginia Heights. This fabulous property could have a full renovation to make best use of the existing home, or the 16,000+ square foot lot offers the perfect opportunity to build the new home of your dreams and

    Frank Ferrell FERRELL REALTY, INC.

    233 Hampden Place, Winter Park, FL 32789
  • /50

    $790,000 Open Sun 2PM - 4PM

    • 4 Beds
    • 3.5 Baths
    • 2,604 Sq Ft

    438 W Swoope Ave, Winter Park, FL 32789

    Located within the private enclave of 400 West—an exclusive 9-residence community just steps from Park Avenue—this contemporary townhome offers a rare blend of quality construction, refined interiors & exceptional walkability. From the moment you step inside—whether through the private garage or along the garden-style front path—you’re met with a bright open-concept main floor that blends

    Padgett McCormick KELLY PRICE & COMPANY LLC

    438 W Swoope Ave, Winter Park, FL 32789
  • /37

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 1,951 Sq Ft

    595 Huntington Ave Unit 4, Winter Park, FL 32789

    You Found It!!! Beautiful Winter Park townhome that feels like a single-family residence. Situated on a private lane with no through-traffic. Ten-minute walk to Park Avenue and Rollins, five-minute walk to Lake Virginia. This exquisite end-unit is part of a sought-after 10-unit community. Three Bedrooms and two and a half Baths, volume ceilings, pristine travertine marble floors and an

    Andrew Livingston COLDWELL BANKER RESIDENTIAL RE

    595 Huntington Ave Unit 4, Winter Park, FL 32789
  • /55

    $1,050,000

    • 4 Beds
    • 3.5 Baths
    • 2,173 Sq Ft

    208 Brewer Ave, Winter Park, FL 32789

    Welcome to this beautifully updated 4-bedroom, 3.5-bath Craftsman-style home, offering just under 2,200 sq ft of thoughtfully designed living space. From the moment you arrive, the charm is undeniable—with classic architectural details and a welcoming front porch that set the tone for what’s inside. Step into an open and inviting layout featuring an updated kitchen with modern cabinetry,

    Cassandra King COMPASS FLORIDA LLC

    208 Brewer Ave, Winter Park, FL 32789
  • /47

    $2,200,000

    • 5 Beds
    • 4.5 Baths
    • 3,174 Sq Ft

    1710 Oneco Ave, Winter Park, FL 32789

    Stunning 2020 Mediterranean Pool Home by M. Lahr Custom Homes in one of the sought-after neighborhoods of Winter Park. Experience unparalleled luxury in this breathtaking exquisite 5-bedroom, 4.5-bathroom home with bonus room that offers a perfect blend of comfort, and functionality. This exceptional residence features high-end designer finishes and exceptional craftsmanship throughout for modern

    Rhonda Chesmore KELLY PRICE & COMPANY LLC

    1710 Oneco Ave, Winter Park, FL 32789
  • /30

    $609,900

    • 3 Beds
    • 3 Baths
    • 1,701 Sq Ft

    915 Aragon Ave, Winter Park, FL 32789

    Nestled in a peaceful enclave near Park Avenue in Winter Park, this inviting 3 bedroom, 3 bathroom, 1,701 SF townhome offers classic Florida living with modern comforts. A welcoming entry opens to bamboo wood flooring that flows through the main living areas. The living room and adjacent dining space connect seamlessly to the gorgeous kitchen, featuring 42" wood cabinets, stainless appliances,

    Shelby Kirsch REAL PROPERTY MANAGEMENT AND REALTY

    915 Aragon Ave, Winter Park, FL 32789
  • /41

    $1,200,000

    • 6 Beds
    • 4 Baths
    • 4,277 Sq Ft

    2080 Wood Thrush Ln, Winter Park, FL 32792

    Exceptional Living Awaits in the Heart of Winter ParkNestled in the sought-after community of Waters Edge at Hawks Crest, this stunning4268 square-foot energy-efficient home offers an exquisite blend of classic eleganceand modern comfort. This Kerville II model, built by Meritage Homes in 2020, has beenthoughtfully designed to be both welcoming and refined.From the moment you

    Nate Klutznick LOKATION

    2080 Wood Thrush Ln, Winter Park, FL 32792
  • /55

    $1,149,000

    • 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
  • /23

    $998,000

    • 4 Beds
    • 3.5 Baths
    • 4,088 Sq Ft

    1319 Heavenly Cove, Winter Park, FL 32792

    FULLY FURNISHED HOME THAT IS MOVE-IN READY! ALL FURNITURE INCLUDED IN THE SALES PRICE! Amazing home located in a quiet gated subdivision in Winter Park near Trinity Prep. The home provides a wonderful layout with high ceilings and an open concept – perfect for entertaining. Updated kitchen with clean white cabinets, spacious chef’s island, and GE stainless steel appliances to cook a delicious

    Doug Addeo COMMUNITY REALTY ASSOCIATES

    1319 Heavenly Cove, Winter Park, FL 32792
  • /72

    $1,095,000

    • 4 Beds
    • 3.5 Baths
    • 2,770 Sq Ft

    2607 Lafayette Ave, Winter Park, FL 32789

    Welcome to 2607 Lafayette Avenue – a stunning custom-built residence nestled in one of Winter Park’s most desirable neighborhoods. This beautifully crafted home offers 4 spacious bedrooms, 3.5 bathrooms, and 2,770 square feet of refined living space designed for modern comfort and effortless entertaining.Step inside to discover an open-concept layout that seamlessly connects the kitchen,

    Maggie Walas FORTUNE INTERNATIONAL REALTY

    2607 Lafayette Ave, Winter Park, FL 32789
  • /39

    $950,000

    • 4 Beds
    • 4 Baths
    • 3,646 Sq Ft

    5510 Howell Branch Rd, Winter Park, FL 32792

    Welcome to an extraordinary Florida residence, situated on a sprawling 1.52-acre lot. The main residence features an attached two-car garage, complemented by a detached two-car garage—perfect for additional vehicles or workshop space. For those in need of versatile storage or business potential, a 3,500-square-foot two-story warehouse offers ample opportunity, while a spacious outdoor

    Shaun Shaffner Blue Marlin Real Estate

    5510 Howell Branch Rd, Winter Park, FL 32792
  • /34

    $549,000

    • 3 Beds
    • 2.5 Baths
    • 1,775 Sq Ft

    2238 Hawick Ln, Winter Park, FL 32792

    Welcome to 2238 Hawick Lane, where modern living meets timeless charm in Winter Park, FL! This delightful 3-bedroom, 2.5-bathroom end-unit condo, crafted in 2006, blends modern elegance with a dash of wit, making every day a charming escape.Step inside to an open floor plan that exudes warmth and sophistication. The first level boasts high ceilings and chic tile floors, perfect for

    Brian Rotenberger COMPASS FLORIDA LLC

    2238 Hawick Ln, Winter Park, FL 32792
  • /38

    $999,000

    • 3 Beds
    • 2 Baths
    • 1,887 Sq Ft

    913 Moss Ln, Winter Park, FL 32789

    ***Lease purchase available | Remodeled in 2023 | Furniture package available | Short term rental allowed*** Discover Your Dream Retreat at 913 Moss Lane, Winter Park, FL – A 2023 Masterpiece Awaits! Step into luxury living at 913 Moss Lane, a breathtakingly renovated 3-bedroom, 2-bath haven in the heart of Winter Park, boasting 1,887 square feet of modern elegance and timeless Florida charm.

    Peter Rodriguez VECTOR PROPERTY GROUP

    913 Moss Ln, Winter Park, FL 32789
  • /28

    $524,000

    • 3 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    1745 Indiana Ave Unit J, Winter Park, FL 32789

    Welcome to this beautifully updated townhome, conveniently located near everything you need. Step inside to discover a bright, open floor plan with new luxury vinyl plank flooring that flows seamlessly throughout the main level. The kitchen has been recently updated with white cabinets and features newer appliances, including a refrigerator, dishwasher, and washer/dryer—all added in the past

    Chase Morton Tate COMPASS FLORIDA LLC

    1745 Indiana Ave Unit J, Winter Park, FL 32789
  • /45

    $1,200,000

    • 4 Beds
    • 3 Baths
    • 2,388 Sq Ft

    1341 Lyndale Blvd, Winter Park, FL 32789

    Ideally located in the heart of Winter Park, just steps from iconic Park Avenue and around the corner from Winter Park Village, this beautifully renovated 4-bedroom, 3-bath home offers the ultimate in walkable luxury living. Nestled on a charming brick street lined with sidewalks, this residence combines timeless elegance with unbeatable convenience.Inside, enjoy 10’ ceilings, rich wood,

    Brandon Geers COMPASS FLORIDA LLC

    1341 Lyndale Blvd, Winter Park, FL 32789
  • /65

    $935,000

    • 5 Beds
    • 3.5 Baths
    • 3,598 Sq Ft

    5325 Cypress Reserve Place, Winter Park, FL 32792

    ATENTION BUYERS!! PRICE ADJUSTED TO $935K & $15K SELLER CONCESSION TOWARDS BUYERS CLOSING COST WITH FULL ASKING PRICE!!Your Dream Home Awaits!Imagine a home that blends luxury, comfort, & convenience that’s exactly what you’ll find at 5325 Cypress Reserve Pl in Winter Park’s exclusive gated community Cypress Reserve.This move-in-ready 5-bedroom masterpiece isn’t just a house

    Dori Estrada LPT REALTY, LLC

    5325 Cypress Reserve Place, Winter Park, FL 32792
  • /68

    $960,000

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

    250 Cortland Ave, Winter Park, FL 32789

    Welcome to the epitome of the Winter Park lifestyle at 250 Cortland Ave, nestled among million-dollar homes on one of the most picturesque, tree-lined, brick streets in the heart of Winter Park, FL. This meticulously maintained house presents the ideal blend of luxury and comfort, with a low-maintenance, fully landscaped yard, complete with a sprinkler system, an oversized two-car garage, a

    Alexandra Nordine EXP REALTY LLC

    250 Cortland Ave, Winter Park, FL 32789

Showing Results 1 - 40, Page 1 of 6

Home Trends in Winter Park, FL

Housing Trends

Median Sale Price
$469,190
Median Single Family Sale Price
$830,000
Median Townhouse Sale Price
$775,000
Median 2 Bedroom Sale Price
$170,000
Median 1 Bedroom Sale Price
$149,000
Average Price Per Sq Ft
$339
Number of Homes for Sale
29
Last 12 months Home Sales
171
Months of Supply
2.00
Median List Price
$630,000
Median Change From 1st List Price
6%
Median Home Sale Price YoY Change
5%
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