475 ft
Distance
| Address | Bed / Bath | Listing Price |
|---|---|---|
315 S BOYD STREET
Located in the heart of Historic Downtown Winter Garden…golf cart district! Walkable to amazing restaurants, boutiques, breweries, splash pad, Saturday Farmer’s Market or one of the many specialty events held throughout the year! This darling 1930’s craftsman bungalow had a complete restoratio
Living Area:
1511 Sqft.
|
3
Beds,
2
Baths
|
$550,000 |
627 AUTUMN OAKS LOOP
THE HEART OF WINTER GARDEN… Shopping and Dining just blocks away.
Located in the Golf Cart District, the community of Winter Oaks is a hidden gem offering this beautiful 5-Bedroom, 3-Bath Traditional Home with 3000 sq/ft of living space. The rear alley garages allow for timeless architecture, m
Living Area:
3000 Sqft.
|
5
Beds,
3
Baths
|
$749,000 |
40 W SMITH STREET
Welcome home to 40 W Smith St. Step into a piece of Winter Garden's rich history with this captivating, charming historic home in the "golf district" in the heart of downtown Winter Garden. Nestled in the heart of downtown Winter Garden, enjoy easy access to the widely popular Plant Street farmer's
Living Area:
2225 Sqft.
|
4
Beds,
2
Baths
|
$750,000 |
750 S PARK AVENUE
Welcome to 750 S Park Avenue, a beautifully maintained and fully RENOVATED home offering comfort, charm, and modern convenience in one of Winter Garden’s most desirable neighborhoods.This 3-bedroom, 1.5-bath residence spans approximately 1,186 square feet and sits on a well-kept lot with mature FR
Living Area:
1086 Sqft.
|
3
Beds,
2
Baths
|
$430,000 |
241 N DILLARD STREET
Welcome to a Once-in-a-Lifetime Opportunity in the Heart of Downtown Winter Garden
Nestled beneath the shade of enchanting oak trees, this stately residence sits proudly on a rare triple lot in one of Central Florida’s most coveted locations — the Golf Cart District of Historic Downtown Winter
Living Area:
3507 Sqft.
|
3
Beds,
3
Baths
|
$1,800,000 |
446 MILLWOOD PLACE
**HISTORIC DOWNTOWN WINTER GARDEN -- GOLF CART DISTRICT -- WEST ORANGE TRAIL** **OVERSIZED PRIVATE LOT** **FOUR BEDROOMS -- THREE FULL BATHROOMS** **NEWER HVAC - 2024 + NEWER WATER HEATER -- 2021** **HARDWOOD FLOORING** **FULLY FENCED YARD -- COVERED & SCREENED PATIO LANAI** Welcome to this be
Living Area:
2022 Sqft.
|
4
Beds,
3
Baths
|
$550,000 |
102 VALENCIA SHORES DRIVE
FALL in love with this beautifully updated 3 bedroom 2 bath home, nestled in Winter Garden's highly sought after golf cart district. The open and airy floor plan offers a seamless flow between living, dining and kitchen areas, making it perfect for both entertaining and everyday living. The thought
Living Area:
1910 Sqft.
|
3
Beds,
2
Baths
|
$579,900 |
797 E BAY STREET
Welcome Home to Winter Garden Living!
This beautiful 4-bedroom, 3-bath home sits on an oversized, fully fenced lot, offering plenty of space for entertaining, relaxing, and play. Enjoy mornings with coffee on the patio and evenings with wine and barbecues under the stars in your private backyard oa
Living Area:
2428 Sqft.
|
4
Beds,
3
Baths
|
$499,000 |
229 N HIGHLAND AVENUE
Completely Renovated 4BR/2BA Home – Walk to Downtown Winter Garden located just steps from the vibrant heart of Downtown Winter Garden. This move-in-ready property has been thoughtfully renovated from top to bottom, offering modern comfort and timeless style.4 spacious bedrooms and 2 full bathroom
Living Area:
1720 Sqft.
|
4
Beds,
2
Baths
|
$779,900 |
714 PARKMONT PLACE
Welcome to the GOLF CART district of WINTER GARDEN! This STUNNING home was the former Ryan MODEL HOME located in Covington Park. Upon arrival you will notice the SHOW STOPPER LANDSCAPING which provides the most desirable CURB APPEAL. Step inside and you will find a very well maintained home that pro
Living Area:
2190 Sqft.
|
3
Beds,
2
Baths
|
$579,900 |
329 W BAY STREET
Investor special or perfect project home just steps from historic Downtown Winter Garden! This 2-bedroom, 1-bath bungalow sits on a generous lot and offers tons of potential for renovation or redevelopment. Bring your vision to life—restore its original charm or reimagine the space entirely. The l
Living Area:
1004 Sqft.
|
2
Beds,
1
Bath
|
$420,000 |
100 TEMPLE GROVE DRIVE
Welcome home to a true Winter Garden gem that perfectly blends modern comfort, timeless design, and small-town charm. Nestled on a spacious private lot with no HOA, this beautifully expanded and reimagined residence captures the spirit of historic Winter Garden while delivering every modern luxury.
Living Area:
3182 Sqft.
|
4
Beds,
3
Baths
|
$1,050,000 |
434 MILLWOOD PLACE
Stunning 3-bedroom, 2-bath home located in the heart of downtown Winter Garden’s Golf Cart District. This well-maintained property features wood floors in the living room, tile in the dining and kitchen areas, and ceiling fans in every room. The spacious master suite can be converted into two room
Living Area:
1696 Sqft.
|
3
Beds,
2
Baths
|
$447,900 |
1125 LINCOLN TERRACE
**Seller Concessions or Mortgage Rate Buy Down Available* DISCOVER THE SERENE BEAUTY OF THIS STUNNING HOME! GORGEOUS 3-BEDROOM, 1-BATHROOM, 1-CARPORT HOME boasting a SPACIOUS FLOOR PLAN that effortlessly blends functionality with modern style. From the moment you step inside, you’ll be greeted by
Living Area:
814 Sqft.
|
3
Beds,
1
Bath
|
$257,400 |
351 FLORAL DRIVE
PRICE IMPROVEMENT - Stunning Renovated Ranch on Prime Corner Lot in Historic Downtown Winter Garden - Welcome to a prime corner lot property in Historic Downtown Winter Garden that perfectly blends modern luxury with small-town charm! While this beautiful home has been lovingly maintained in the sel
Living Area:
1722 Sqft.
|
3
Beds,
2
Baths
|
$689,000 |
436 VALLEY VIEW DRIVE
Welcome Home!
Discover a rare opportunity to own a beautifully upgraded home in the highly sought-after Courtlea Oaks community, nestled in the heart of Winter Garden’s charming golf cart district. This meticulously maintained home features luxury vinyl plank flooring throughout and a flexible op
Living Area:
3130 Sqft.
|
3
Beds,
4
Baths
|
$1,049,000 |
823 MAGNOLIA AVENUE
Under Construction. No HOA, one-story floorplans featured in Winter Garden, Florida. Inside this 3-bedroom, 2-bathroom home, you’ll find 1,210 square feet of comfortable living. The living area is an open concept, where your kitchen, living, and dining areas blend seamlessly into a space perfect f
Living Area:
1210 Sqft.
|
3
Beds,
2
Baths
|
$343,000 |
1085 CHASE DRIVE
Highly Motivated Seller! Ride your golf cart straight to charming Plant Street from this beautiful 4-bedroom home with a private office and 3 full bathrooms offering nearly 3,000 sq. ft. of spacious living—perfect for work, family, and entertaining. This home features European-style rounded corne
Living Area:
2967 Sqft.
|
4
Beds,
3
Baths
|
$649,999 |
515 9TH STREET
Discover an incredible opportunity just minutes from the vibrant and historic Downtown Winter Garden! This beautifully updated 3 bedroom, 2 bathrooms home is located in an unincorporated area, giving buyers added flexibility and income potential while keeping maintenance simple and affordable. The o
Living Area:
770 Sqft.
|
3
Beds,
2
Baths
|
$287,900 |
618 FOSTER AVENUE
Newly renovated INCOME PRODUCING 3-bedroom, 2-bathroom home nestled in the heart of downtown Winter Garden! Hop onto your golf cart or take a few moments' walk towards numerous shops, restaurants, the local farmer's market and all of the other charm that downtown has to offer. This home has been ful
Living Area:
1010 Sqft.
|
3
Beds,
2
Baths
|
$375,000 |
1075 CHASE DRIVE
Welcome to 1075 Chase Drive-located in downtown Winter Garden, just minutes from the charm and energy of Plant Street. This rare, newer-construction single-story home offers a blend of modern comfort and timeless style that’s sure to impress. As you enter, custom tile in the foyer sets the tone, w
Living Area:
2125 Sqft.
|
4
Beds,
2
Baths
|
$625,000 |
753 ORANGE BELT LOOP
--Waterfront Living Steps from Downtown Winter Garden--
Imagine starting your day with coffee on the porch, sunlight reflecting off the water, and the hum of downtown Winter Garden just minutes away. This home offers the perfect mix of tranquil waterfront living and vibrant small-town energy—p
Living Area:
3074 Sqft.
|
4
Beds,
4
Baths
|
$775,000 |
327 S LAKEVIEW AVENUE
Charming Winter Garden Home with In-Law Suite & Botanical Backyard Retreat
Welcome to this beautifully crafted single-family home built in 2014, where quality workmanship, thoughtful design, and everyday convenience come together. Located in the heart of Winter Garden’s desirable golf cart dist
Living Area:
2225 Sqft.
|
3
Beds,
3
Baths
|
$894,900 |
426 N BOYD STREET
One or more photo(s) has been virtually staged. Welcome to your personal retreat in the heart of Winter Garden! Just a short distance from the charm of historic Plant Street. This meticulously maintained three-bedroom, three-bath pool home with a dedicated office blends relaxed luxury with everyday
Living Area:
2637 Sqft.
|
3
Beds,
3
Baths
|
$800,000 |
711 BURCH AVENUE
Welcome to this lovely 3-bedroom, 2-bath home, just minutes from the heart of Downtown Winter Garden. Freshly painted inside and out, with a brand-new kitchen countertop, it feels fresh, modern, and move-in ready. The layout is cozy and practical—perfect for families or anyone looking to enjoy all
Living Area:
1154 Sqft.
|
3
Beds,
2
Baths
|
$450,000 |
336 COURTLEA PARK DRIVE
If you've been searching for a spacious home in a prime location with room to add value, this is your chance! Located in the highly desirable Golf Cart District of Winter Garden, just steps from the West Orange Trail and a short ride to the shops and dining in Historic Downtown, this Taylor Morrison
Living Area:
2640 Sqft.
|
4
Beds,
4
Baths
|
$594,000 |
213 W TILDEN STREET
Located in the heart of DOWNTOWN WINTER GARDEN!!
This beautifully renovated single story home combines charm with modern upgrades.
Completely redesigned in 2021, this home showcases numerous upgrades, including new roof,
new HVAC, recently installed **Whole-House Water Filtratio
Living Area:
2100 Sqft.
|
4
Beds,
2
Baths
|
$789,000 |
113 W DIVISION STREET
Beautifully remodeled 4BR/2BA home with an open-concept kitchen,top in appliances ,quartz countertops, sleek modern bathrooms,new windows, and durable waterproof laminate floors,excellent screen porch. Perfectly located close to the best schools, City Hall, highways, dining, and parks—ideal for fa
Living Area:
1487 Sqft.
|
4
Beds,
2
Baths
|
$629,900 |
402 E MAPLE STREET
Discover an outstanding investment opportunity or multi-generational living solution at 402 E Maple St—a spacious and well-built 6-bedroom, 4/2-bathroom duplex located in the thriving and historic downtown Winter Garden area. This property offers durable block construction on the first floor and s
Living Area:
2876 Sqft.
|
6
Beds,
6
Baths
|
$1,199,999 |
459 MILLWOOD PLACE
One or more photo(s) has been virtually staged. Just in Time for Summer – A Self-Sustaining Paradise with Solar, Pool, Garden & More!
Step into a home that offers not just warmth and comfort, but a lifestyle of sustainability and serenity. This impeccable four-bedroom, two-and-a-half-bath, and
Living Area:
2873 Sqft.
|
4
Beds,
3
Baths
|
$675,000 |
524 S LAKEVIEW AVENUE
One or more photo(s) has been virtually staged. ***NEW REDUCED PRICE!***MOVE IN BEFORE THE HOLIDAYS & TAKE ADVANTAGE OF THE LOWER INTEREST RATES!
The sellers are motivated and ready for the next chapter—creating an incredible opportunity for you to own this beautifully updated Craftsman-style ho
Living Area:
2204 Sqft.
|
3
Beds,
3
Baths
|
$890,000 |
636 COKE AVENUE
Updated 2 Bedroom, 1 Bath Home Near Downtown Winter Garden. Welcome to your dream home! This beautifully updated 2-bedroom, 1-bath home is located just minutes from the heart of downtown Winter Garden, Florida.
Property Highlights:
Fully updated with brand-new cabinetry throughout the home, givin
Living Area:
914 Sqft.
|
2
Beds,
1
Bath
|
$339,999 |
1040 MAXEY DRIVE
This is the great opportunity to the first-time buyer or investor, it affordable in the great growing in Winter Garden.
Living Area:
1184 Sqft.
|
3
Beds,
2
Baths
|
$219,000 |
634 BURCH AVENUE
Welcome to your dream home in the heart of Downtown Winter Garden’s golf cart district—where small-town charm meets modern living. This newly built home is packed with thoughtful design and high-end finishes. Step inside to wide plank luxury vinyl floors, an airy open-concept layout, and sunligh
Living Area:
2448 Sqft.
|
4
Beds,
4
Baths
|
$664,000 |
515 N BOYD STREET
One or more photo(s) has been virtually staged. Discover the charm and convenience of luxurious living in this stunning 5-bedroom, 3-bathroom home, perfectly located in the heart of downtown Winter Garden. With a spacious and thoughtfully designed layout, this residence offers a blend of elegance an
Living Area:
3152 Sqft.
|
5
Beds,
4
Baths
|
$900,000 |