739 ft
Distance
Harper-Shepherd Field, Winter Park, FL, USA
Winter Park, Florida, United States
Categories
Homes for sale near Harper-Shepherd Field, Winter Park, FL, USA
| Address | Bed / Bath | Listing Price |
|---|---|---|
34 STYMIE PLACE
LOCATION, LOCATION, LOCATION! This recently renovated home is located in the heart of College Park and is conveniently situated just steps away from the beautiful Dubsdread golf course. This property is ideal for indoor/outdoor entertaining. Inside, you’ll find a bright and open living space wit
Living Area:
909 Sqft.
|
2
Beds,
1
Bath
|
$445,000 |
870 CARVER STREET
Welcome to 870 Carver Street, a versatile three-bedroom, three-bath residence offering privacy, thoughtful design, and two distinct living experiences in the heart of Winter Park. With 1,875 square feet under air, the property includes a 1,209-square-foot, two-bedroom, two-bath main home and a 666-s
Living Area:
1875 Sqft.
|
3
Beds,
3
Baths
|
$975,000 |
1872 BISCAYNE DRIVE
Back on the market due to seller changing real estate companies - not due to financing or inspections. Don’t miss this rare opportunity to own a professionally landscaped, beautifully maintained home in Winter Park, perfect as a primary residence or a smart investment property! This 1950s bungalow
Living Area:
969 Sqft.
|
2
Beds,
1
Bath
|
$415,000 |
1450 GLENCOE ROAD
Comfort, charm, and LOCATION are KEY for this unique, one-story, KEY West-style pool home with deeded access to Lake Virginia! Nestled on a brick-lined street in the highly sought-after Virginia Heights neighborhood, this location is truly one-of-a-kind, engulfed in the beloved culture and history o
Living Area:
2785 Sqft.
|
4
Beds,
3
Baths
|
$1,625,000 |
1124 MUNSTER STREET
CLOSING COST INCENTIVES OF 15k AVAILABLE, FOR FULL ASKING PRICE.Welcome to your new home! From the moment you enter, you're greeted by a spacious corridor that flows into an expansive open floor plan, seamlessly connecting the living room, dining room, and chef's kitchen. The kitchen is a true shows
Living Area:
1806 Sqft.
|
3
Beds,
2
Baths
|
$880,000 |
1751 GLENCOE ROAD
Nestled just moments from the boutiques and cafés on Park Avenue, this newly completed Davila Homes masterpiece redefines Winter Park luxury living. Perfectly positioned on an expansive 0.30-acre lot, this residence captures attention from the moment you arrive, with its striking architectural deta
Living Area:
4520 Sqft.
|
5
Beds,
7
Baths
|
$3,895,000 |
1324 INDIANA AVENUE
Charming two story bungalow built in 1935. Timeless character meets modern comfort in this beautifully maintained four bedroom, two and a half bath home. Classic architectural details and a welcoming balcony make this beauty special. This residence perfectly blends historic charm with today's lifest
Living Area:
1692 Sqft.
|
4
Beds,
3
Baths
|
$745,000 |
1451 Cavendish Road
Welcome to 1451 Cavendish Road, a beautifully renovated home in the heart of Orwin Manor, one of Winter Park's most desirable and family-friendly neighborhoods. Set on a large and prominent corner lot, this move-in-ready home perfectly balances charm, safety, and convenience just minutes from Park A
Living Area:
1437 Sqft.
|
3
Beds,
2
Baths
|
$619,500 |
1150 KENWOOD AVENUE
Wonderful opportunity - homes rarely come available on this street! Located in the heart of Winter Park, this elegantly designed 3-bedroom, 2.5-bathroom residence offers 2,557 square feet of living space and a 2-car garage on a picturesque tree-lined brick street just minutes from Park Avenue. The f
Living Area:
2557 Sqft.
|
3
Beds,
3
Baths
|
$1,190,000 |
2009 CORNELL AVENUE
Unlock potential in one of Central Florida’s most desirable pockets! This centrally located Winter Park home shines with major updates already completed including a 2018 roof, 2022 HVAC, and fresh interior paint. Just bring a little extra love to elevate the finishes and create instant equity. Per
Living Area:
762 Sqft.
|
2
Beds,
1
Bath
|
$269,000 |
1411 NOTTINGHAM STREET
This contemporary five-bedroom, three-and-a-half-bath home with a detached 384 SF casita in desirable Beverly Shores/Rose Isle showcases designer-inspired finishes and a resort-style pool retreat. Custom-built with a modern aesthetic and open floor plan, it features a gourmet kitchen with an island
Living Area:
4118 Sqft.
|
5
Beds,
5
Baths
|
$3,200,000 |
607 ELLEN DRIVE
Discover sophisticated modern living at 607 Ellen Drive, a stunning new construction home by the acclaimed Lazarus Homes in the heart of Winter Park. This impeccably designed 2,812-square-foot residence showcases contemporary architecture with clean lines, high ceilings, and an abundance of natural
Living Area:
2812 Sqft.
|
4
Beds,
5
Baths
|
$1,630,000 |
1581 FOREST AVENUE
Located just steps from Park Avenue, this extraordinary Winter Park residence was fully rebuilt in 2018 by master custom builder Posada Homes. Set on a 0.39-acre lot along one of Winter Park’s most desirable tree-lined streets, the home makes an immediate impression with its elegant architecture a
Living Area:
4683 Sqft.
|
4
Beds,
6
Baths
|
$3,775,000 |
3223 N ORANGE AVE
Seller is willing to assist with buyer closing costs or assist with interest rate buy down.
Welcome to this beautifully updated 3-bedroom, 2-bath single-family home located at 3223 N Orange Ave, Orlando, FL 32803. This move-in ready property combines modern upgrades with a central location minute
Living Area:
1882 Sqft.
|
3
Beds,
2
Baths
|
$629,000 |
1510 MILLER AVENUE
Under Construction. New Construction – Modern Luxury Meets Urban Living at Winter Park's Newest Neighborhood, Winter Park Grove!
Step into the future of refined living with this stunning new construction pool home, situated in the vibrant heart of Winter Park. Just minutes from the eclectic energ
Living Area:
3252 Sqft.
|
5
Beds,
5
Baths
|
$1,634,900 |
1540 MILLER AVENUE
Under Construction. NEW CONSTRUCTION!!! Welcome to Winter Park Grove — Winter Park’s newest community!
This stunning new Mid-Century Modern–inspired home is designed to impress with its architectural flair, meticulous craftsmanship, and luxurious finishes. Perfectly located near all the shop
Living Area:
2984 Sqft.
|
4
Beds,
4
Baths
|
$1,399,900 |
319 SANTIAGO DRIVE
Nestled in coveted Winter Park’s Sevilla neighborhood, this 4-bed, 4.5-bath pool home delivers 3,500+ SF of refined living including 500 SF upstairs flex suite with its own full bath. A traditional foyer introduces formal living and dining rooms before the home unfolds into a spectacular 2022-reno
Living Area:
3515 Sqft.
|
4
Beds,
5
Baths
|
$1,990,000 |
457 E NEW ENGLAND AVENUE
Nestled in the heart of downtown Winter Park, this beautifully maintained 1920s traditional residence captures the essence of Old Florida charm while offering the comfort of modern amenities. From the moment you arrive, the wraparound porch and circular drive create a welcoming first impression, set
Living Area:
3847 Sqft.
|
5
Beds,
5
Baths
|
$3,100,000 |
207 E KINGS WAY
Under Construction. Step into a world where the timeless charm of Old Winter Park meets the pinnacle of modern luxury designed by Winter Park Design and masterfully crafted by renowned builder Vimaro Homes. Nestled on one of Winter Park’s most coveted tree-lined streets, this stately home immediat
Living Area:
3719 Sqft.
|
5
Beds,
5
Baths
|
$3,650,000 |
1821 ENGLEWOOD ROAD
This stunning new contemporary residence, a five-bedroom, five-and-a-half bath home by the renowned Rex-Tibbs Development, a custom builder for over 40 years, continues to set the standard for luxury living. Perfectly situated on a premium, quiet, charming brick street, the home blends clean archite
Living Area:
3863 Sqft.
|
5
Beds,
6
Baths
|
$3,295,000 |
1875 STAUNTON AVENUE
Welcome to this newer single-family home tucked away in the Karolina On Killarney section of Winter Park. Situated on a generously sized .16 acre lot with no HOA, this property offers both privacy and optimal convenience. Enjoy hopping over to Park Avenue for shopping and restaurants or to the weekl
Living Area:
2036 Sqft.
|
4
Beds,
3
Baths
|
$560,000 |
1166 OAKS BOULEVARD
PRICE IMPROVEMENT-Discover this stunning, custom-built home nestled on a tranquil, tree-lined street just steps from all the charm of Winter Park’s renowned Park Avenue. Located in a peaceful neighborhood, this elegant residence combines sophisticated craftsmanship with luxury features throughout
Living Area:
2860 Sqft.
|
4
Beds,
4
Baths
|
$1,699,999 |
720 W WEBSTER AVENUE
Discover the charm of Winter Park living in this beautifully maintained 1950s home, where convenience and comfort meet modern updates. Just minutes from Park Avenue and Winter Park Village, this 3-bedroom, 2-bath residence offers a lifestyle surrounded by boutique shopping, dining, and cultural expe
Living Area:
1356 Sqft.
|
3
Beds,
2
Baths
|
$575,000 |
Lot #21 KAROLINA AVE
Pre-Construction. To be built. Step into a life where charm meets convenience in the heart of Winter Park. This brand-new 4-bedroom, 3.5-bath, 2,662 sq. ft. home is situated on a 6,748 sq. ft. lot and is a thoughtfully designed masterpiece, blending elegant country charm with the comfort and functio
Living Area:
2662 Sqft.
|
4
Beds,
4
Baths
|
$916,050 |
915 GARDEN DRIVE
Stunning Mid-Century Modern Home in Prime Winter Park Location – Solar Powered, Pool, No HOA
Beautifully maintained Mid-Century Modern raised-ranch home located in one of Winter Park’s most desirable neighborhoods, just a 3-minute walk to Mead Botanical Garden and minutes from Park Avenue, sh
Living Area:
2456 Sqft.
|
3
Beds,
3
Baths
|
$900,000 |
805 NOTTINGHAM STREET
One or more photo(s) has been virtually staged. Charming, Fully Updated Home in Coveted Orwin Manor!
Tucked perfectly between the charm of College Park and the luxury of Park Avenue, this beautifully renovated Orwin Manor home feels like something out of a storybook. Picture quiet, tree-lined str
Living Area:
2296 Sqft.
|
3
Beds,
2
Baths
|
$750,000 |
240 ORANGE TERRACE DRIVE
WHAT ARE YOU WAITING FOR? THIS IS IT! Nestled in the heart of Winter Park near Lake Killarney, this beautifully updated 4-bedroom, 2-bath home offers the perfect blend of comfort, convenience, and style. Just minutes from Fairbanks and I-4, you’ll enjoy quick access to top shopping, dining, and a
Living Area:
1718 Sqft.
|
4
Beds,
2
Baths
|
$515,000 |
501 LAKEVIEW AVENUE
Under Construction. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-suite guest retreat on the ma
Living Area:
3253 Sqft.
|
4
Beds,
5
Baths
|
$1,390,000 |
525 LAKEVIEW AVENUE
Under Construction. Renderings available soon. Brand-new custom construction on coveted Lakeview Avenue marries classic Winter Park charm with crisp, contemporary living. Behind its inviting façade you’ll find an airy two-story layout featuring four bedrooms and 4 ½ baths, including a full en-su
Living Area:
3253 Sqft.
|
4
Beds,
5
Baths
|
$1,390,000 |
1221 RICHMOND ROAD
An Award-Winning Architectural Masterpiece built by Chris Salhab of Valdara Custom Homes. 5,164 Sq Ft | 5 Bedrooms | 6 Bathrooms | Welcome to 1221 Richmond Rd, an extraordinary custom residence located in the coveted Virginia Heights neighborhood of Winter Park—offering deeded lake access to the
Living Area:
5164 Sqft.
|
5
Beds,
6
Baths
|
$5,450,000 |
1270 ARLINGTON PLACE
Modern Elegance in the Heart of Winter Park!
Located just a half-mile from the renowned shops and dining of Park Avenue, this architecturally striking residence blends luxury, modern design, and thoughtful functionality. Designed by Michael Wenrich and built by Jim Winters, every inch of this hom
Living Area:
2964 Sqft.
|
3
Beds,
4
Baths
|
$1,649,000 |
800 HAMILTON PLACE COURT
Custom-built and beautifully maintained, this large 3-bedroom home with loft is located in prime Old Winter Park on a quiet cul-de-sac. The interior boasts 18'+ high ceilings, creating a grand and airy atmosphere throughout the main living spaces. High-end finishes include Viking stainless steel app
Living Area:
3363 Sqft.
|
3
Beds,
4
Baths
|
$1,295,000 |
1820 GLENCOE ROAD
Discover the ultimate in luxury real estate in Winter Park, Florida with this Dutch West Indies–inspired custom home built by FG Schaub Custom Homes. Ideally located just minutes from Park Avenue’s upscale dining and shopping, Rollins College, and the cultural charm of downtown Winter Park, this
Living Area:
4055 Sqft.
|
5
Beds,
7
Baths
|
$3,825,000 |
1473 BERKSHIRE AVENUE
One or more photo(s) has been virtually staged. Brand-New 2025 Mediterranean Luxury in Historic Winter Park. Introducing 1473 Berkshire Avenue — a just-completed luxury residence nestled on one of Winter Park’s most peaceful, tree-lined, and century-old streets. This two-story Mediterranean mast
Living Area:
2895 Sqft.
|
5
Beds,
4
Baths
|
$1,589,904 |
1473 Berkshire Avenue
Exquisite New 2025 Luxury Home in the Heart of Winter Park - Welcome to 1473 Berkshire Avenue - a stunning, brand-new 2025 luxury residence located in the highly sought-after town of Winter Park, Florida. This beautifully crafted two-story Mediterranean-style home blends timeless architecture with m
Living Area:
2895 Sqft.
|
5
Beds,
4
Baths
|
$1,589,904 |
922 N PENNSYLVANIA AVENUE
Experience timeless elegance and modern sophistication in this stunning 3 bedroom, 4 bath Mediterranean home, ideally situated on the 4th hole of the beautifully maintained Winter Park 9-hole golf course. Nestled on a 75 x 100 lot, this 3,440 sq ft residence was extensively renovated in 2017. From t
Living Area:
3440 Sqft.
|
3
Beds,
4
Baths
|
$2,175,000 |
240 CAMBRIDGE BOULEVARD
3-Bed, 2-Bath Home in Prime Winter Park Location! Steps away from paddleboarding, kayaking or fishing on beautiful Lake Killarney!
Welcome to your new home nestled in one of Winter Park’s most desirable areas—with easy access to I-4. This beautifully maintained 3-bedroom, 2-bathroom residence
Living Area:
1630 Sqft.
|
3
Beds,
2
Baths
|
$525,000 |
1996 INDIANA AVENUE
Investors/builders, here is your next project. This oversized lot (6,957 sf) on a dead-end street is perfect for our next investment opportunity. With a Winter Park address, this lot contains a spectacular location. In the bustling area of College Park/Winter Park, this lot sits near the main cam
Living Area:
818 Sqft.
|
2
Beds,
1
Bath
|
$250,000 |
541 W CANTON AVENUE
Timeless elegance meets boutique craftsmanship at 541 W Canton Avenue—an exceptional new construction home by Urban Perch, proudly featured in the 2025 Parade of Homes Orlando. Located just steps from Winter Park’s iconic Park Avenue, this French Quarter-inspired residence blends historic charm
Living Area:
3553 Sqft.
|
4
Beds,
4
Baths
|
$2,935,000 |
3601 MIDIRON DRIVE
BUILD YOUR DREAM HOME IN WINTER PARK!
Nestled directly across from the historic Dubsdread Golf Course, this property offers a unique chance to invest in one of Orlando’s most sought-after neighborhoods. Situated on a generous 150' x 60' lot along Midiron Drive—a street experiencing a transforma
Living Area:
954 Sqft.
|
2
Beds,
1
Bath
|
$459,000 |
1910 GLENCOE ROAD
Under Construction. Stunning architectural masterpiece built by LUIH homes nestled in the heart of prestigious Winter Park. This brand-new construction embodies the perfect fusion of contemporary design, timeless elegance, and exceptional quality offering 4 bedrooms, 4 full bathrooms, 2 half bathroo
Living Area:
4205 Sqft.
|
4
Beds,
6
Baths
|
$3,490,000 |
1564 CAVENDISH ROAD
Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potential. Updated with original hardwood floors, gas fireplace, granite kitchen, and bath. The 3rd BR functions as a guest room or office. Spacious fenced yard with wood deck and room for a pool. Deep garage offer
Living Area:
1140 Sqft.
|
3
Beds,
1
Bath
|
$450,000 |
1840 W FAWSETT ROAD
Experience the ultimate in luxury lakefront living in this meticulously renovated estate where every surface has been reimagined with the finest finishes and thoughtful design. This stunning property represents a rare opportunity to own a completely modernized waterfront sanctuary that seamlessly bl
Living Area:
4129 Sqft.
|
5
Beds,
5
Baths
|
$4,295,000 |
720 N PENNSYLVANIA AVENUE
Nestled in one of Winter Park’s most sought-after locations, this 3-bedroom, 2-bathroom home seamlessly blends modern elegance with everyday comfort. From the moment you step inside, you'll be captivated by the sleek, contemporary finishes, recessed lighting, and stylish fixtures that enhance ever
Living Area:
1115 Sqft.
|
3
Beds,
2
Baths
|
$550,000 |
726 N PENNSYLVANIA AVENUE
Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of modern elegance and prime location. The gourmet kitchen boasts 42” black cabinets, granite countertops, a decorative backsplash, and stainless steel appliances, making it a stunning focal point of the home. The op
Living Area:
1167 Sqft.
|
3
Beds,
2
Baths
|
$695,000 |
726/720 N PENNSYLVANIA AVENUE
Welcome to this rare Winter Park gem offering unmatched flexibility and investment potential. Whether you’re looking for a turnkey rental property, a multigenerational living solution, or a home with a private in-law or student suite, this property delivers! Each spacious unit boasts 3 bedrooms an
Living Area:
2284 Sqft.
|
6
Beds,
4
Baths
|
$1,215,000 |
1400 S PENNSYLVANIA AVENUE
Look at this rare opportunity to own a chic and trendy residence in winter park in an incredible location.
You will be amazed at this fully remodeled one level four bedroom home on a fenced corner lot. This home has amazing curb appeal, with its wide half circle paved driveway, with plenty of park
Living Area:
2310 Sqft.
|
4
Beds,
3
Baths
|
$1,250,000 |
