Winter Park FL Real Estate & Homes for Sale

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Beds:
4
Baths:
4.00
Sq.Ft.:
4,920
Status:
NEW LISTING
MLS#:
O6457385
Type:
Single Family
Subdivision:
LAKE KNOWLES TERRACE
Lot size:
0.22 Acres
Year built:
2020
A broker reciprocity listing Courtesy: STOCKWORTH REALTY GROUP 407-909-5900
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ADDITIONAL INFORMATION

Beautifully designed and appointed, this stunning contemporary residence offers the perfect combination of modern luxury, comfortable living, and exceptional indoor-outdoor entertaining. Ideally located in the quieter, more intimate section of Winter Park's coveted Nut streets, this home offers a wonderful neighborhood setting just minutes from the boutiques, acclaimed restaurants, and vibrant lifestyle of Park Avenue . Light-filled interiors, designer upgrades, and beautiful wood flooring create an inviting first impression. A spacious office features impressive eight-foot windows and beautiful built ins while the open-concept living area seamlessly connects the chef's kitchen, dining space, and expansive family room. The kitchen showcases light quartz countertops, premium appliances, a custom range hood, and designer lighting. The family room is anchored by a contemporary fireplace and custom shelf details. The downstairs primary suite provides a private retreat with dual vanities, a soaking tub, and an impressive 6-by-12-foot walk-through shower featuring dual showerheads and glass-tile walls. Oversized sliding glass doors extend the living space to an 18-by-15-foot covered lanai with tongue-and-groove ceilings, a fully equipped outdoor kitchen, and retractable screens. The beautifully landscaped backyard is an entertainer's dream, complete with a gas-heated pool, integrated hot tub, sun shelf, and generous green space. Upstairs, a sunlit staircase leads to a spacious loft with French doors opening to a front-facing balcony, offering flexibility for a second living area or playroom. Three additional bedrooms, two full bathrooms, and a large gym provide ample accommodations for family and guests. A large laundry room with custom built-ins completes the second floor. Enjoy walkable access to Phelps Park and the Winter Park YMCA, with Park Avenue, the Winter Park 9-hole golf course, and the popular Orlando Avenue dining and shopping districts just moments away. Zoned for highly sought-after Winter Park schools, this exceptional newer-construction home offers the opportunity to enjoy the very best of Winter Park living, combining contemporary luxury, a peaceful neighborhood setting, and an unparalleled lifestyle close to everything.

Beds:
2
Baths:
2.00
Sq.Ft.:
908
Status:
NEW LISTING
MLS#:
R4912361
Type:
Single Family
Subdivision:
MEAD GARDEN
Lot size:
0.02 Acres
Year built:
1967
A broker reciprocity listing Courtesy: NOVANEST REALTY LLC 407-489-6883
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ADDITIONAL INFORMATION

LOCATION, LOCATION, LOCATION! Welcome to Mead Gardens Condominiums in the heart of Winter Park! Discover the perfect combination of comfort, convenience, and lifestyle in this charming 2-bedroom, 2-bathroom condominium offering approximately 908 square feet of living space. This inviting second-floor residence features an open floor plan, a spacious living area, a functional kitchen, and two generously sized bedrooms, each offering comfort and versatility. Enjoy the added benefit of a private balcony, perfect for relaxing and enjoying the peaceful garden surroundings. Residents can take advantage of the community swimming pool and convenient access to nearby shopping, restaurants, parks, and entertainment. Ideally situated just minutes from the beautiful Mead Botanical Garden, Park Avenue, Rollins College, and Winter Park Village, this property offers an excellent opportunity to enjoy everything Winter Park has to offer. Whether you are a first-time homebuyer, looking to downsize, or searching for an investment opportunity, this condominium offers an exceptional location and convenient Central Florida lifestyle. Don't miss the opportunity to make this Winter Park property your next home!

Beds:
4
Baths:
5.00
Sq.Ft.:
5,100
Status:
NEW LISTING
MLS#:
O6457191
Type:
Single Family
Subdivision:
TANTUM ADD
Lot size:
0.21 Acres
Year built:
2020
A broker reciprocity listing Courtesy: KELLER WILLIAMS WINTER PARK 407-545-6430
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ADDITIONAL INFORMATION

Discover an exceptional opportunity to own a beautifully designed luxury home overlooking the prestigious Winter Park Nine Golf Course in one of Winter Park, Florida’s most desirable neighborhoods! Built in 2020, this stunning residence offers approximately 3,500 square feet of thoughtfully designed living space, featuring 4 bedrooms and 4.5 bathrooms. From the moment you step inside, you'll be welcomed by an abundance of natural light, an impressive open-concept floor plan, and soaring ceilings accented by elegant tray ceiling details. Every element of this home comes together to create an atmosphere of sophistication, comfort, and true luxury living. The spacious interior seamlessly blends the living, dining, and entertaining spaces, creating the perfect environment for both everyday living and hosting guests. Step outside to your own private backyard oasis, complete with an amazing pool, perfect for enjoying the beautiful Florida lifestyle. The property also features a spacious two-car garage and a highly desirable in-law suite located above the garage. Complete with its own private kitchen, this separate living space is ideal for extended family, overnight guests, multigenerational living, or a private retreat. Located in one of the most sought-after neighborhoods in Winter Park, this exceptional property offers the opportunity to enjoy golf course living while remaining close to everything that makes Winter Park so special. From its newer construction and light-filled open spaces to its impressive outdoor living area and versatile separate guest quarters, this home delivers the perfect combination of elegance, functionality, and luxury. Don't miss your opportunity to experience this remarkable Winter Park residence!

Beds:
4
Baths:
4.00
Sq.Ft.:
4,115
Status:
NEW LISTING
MLS#:
O6456172
Type:
Single Family
Subdivision:
PENNSYLVANIA PLACE REP
Lot size:
0.24 Acres
Year built:
2002
A broker reciprocity listing Courtesy: COLLADO REAL ESTATE 386-427-0002
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ADDITIONAL INFORMATION

A Spacious and Gracious Home in Winter Park's coveted Pennsylvania Place neighborhood. Located across the street from the community park, and conveniently located near downtown Winter Park, Winter Park Village, Whole Foods, Publix and the Lee Rd. entrance to I-4. Just minutes from Maitland and Orlando. You are welcomed into this lovely residence through a traditional foyer and entry hall. Downstairs you'll enjoy the large, open kitchen with solid wood cabinetry, large island, granite countertops and integrated appliances. Natural gas cooktop in the island, wall oven and built-in microwave, deep under-mounted sink, panelized refrigerator and a built-in desk area. The kitchen provides direct access to the rear-entry garage. The kitchen also opens to a spacious casual dining area and a large living room with natural gas fireplace and built-in cabinetry. On the other side, the kitchen flows through a "Butler's Pantry" to a separate walk-in pantry and to the formal dining room. The living room opens to a large and private covered back porch and patio. From both the patio and the rear-entry garage you have direct access to a lush green space and quiet alley way. One of the many surprise and delights you'll find in this residence is a ground floor bedroom with full en-suite bathroom. This provides privacy for your guests and the flexibility to use as an office or 4th bedroom. Proceeding up to the 2nd floor, either via the private residential ELEVATOR or elegant Stairway, you find a spacious loft/media area that opens to the Primary Suite, Bedrooms 2 and 3 (both with en-suite bathrooms) and the conveniently located laundry room with utility sink and tons of storage. The Primary Suite enjoys a very large bathroom with jetted tub, separate shower, private W/C, two separate vanities with abundant storage. You'll also enjoy the very large walk-in closet with custom closet system. From the loft/media area you have direct access to a walk-in and air conditioned attic for safely storing everything you want out of sight. Two Separate A/C Units (both 2019), Natural Gas Water Heater (2019). After 23 years of being loved by one family, this home is ready for you to make it your own. The perfect combination of a spacious, well-built home situated on a low maint. property and located in a pristine neighborhood close to everything we all love about Winter Park. All measurements are approx., and Buyer resp. to verify all dimensions.

Beds:
5
Baths:
5.00
Sq.Ft.:
4,719
Status:
NEW LISTING
MLS#:
O6455383
Type:
Single Family
Subdivision:
TEMPLE HEIGHTS
Lot size:
0.23 Acres
Year built:
2027
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
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ADDITIONAL INFORMATION

Under Construction. A commanding front façade, and a coveted brick-street setting near the Vias. Interiors defined by natural stone, architectural detail, and a thoughtful balance of grandeur and intimacy. This distinctive Winter Park residence brings together the elements that make a luxury home memorable and a location that is difficult to replicate. The arrival is dramatic featuring a soaring two-story foyer that opens to a spacious living room where wood beams and substantial stonework establish a rich material palette. A stone-wrapped fireplace anchors the room, complemented by a built-in entertainment center and a wet bar with a wine refrigerator and sink. Whether hosting a large gathering or enjoying an evening by the fire, the space feels equally suited to both. Taj Mahal countertops take center stage in the kitchen, paired with custom cabinetry, a paneled refrigerator, and a Thermador appliance package. A generous adjoining dirty kitchen provides a separate sink and additional prep-space. The downstairs primary suite offers privacy and direct access to the backyard through sliding doors. In the bath, marble finishes, dual vanities, and a freestanding soaking tub create an elegant retreat. An arched shower entrance introduces a distinctive architectural detail, with dual shower heads completing the experience. An expansive closet by Idelli brings the same attention to detail to the dressing space. A second downstairs suite accommodates guests or a private office, while a laundry room supports everyday convenience. Upstairs, three additional bedrooms and a spacious bonus room create a separate setting for family, guests, and recreation. The outdoor living space is equally as impressive. A full summer kitchen sets the stage for open-air dining, with a heated pool and spa providing the centerpiece for afternoons and evenings at home. Substantial green space adds another dimension to the backyard, offering room to gather beyond the pool. The surrounding neighborhood places this residence in exceptional company, with impressive estates lining the street. Phelps Park and the YMCA are within walking distance; the Winter Park Racquet Club, Park Avenue’s boutiques and restaurants, and downtown Winter Park are close by. Interlachen Country Club further enhances the appeal of this sought-after location. With its stunning architecture, richly appointed interiors, and exceptional outdoor living, this residence makes a lasting statement on one of Winter Park’s coveted brick streets.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,889
Status:
NEW LISTING
MLS#:
O6457113
Type:
Single Family
Subdivision:
FAIRBANKS SHORES FIRST ADD
Lot size:
0.22 Acres
Year built:
1943
A broker reciprocity listing Courtesy: ORLANDO REGIONAL REALTY 407-751-2111
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ADDITIONAL INFORMATION

Heart of Winter park- Investment opportunity, Renovate or Rebuild! Easy access to Winter park , Orlando & College park. Minutes to I4 Fairbanks entrance/ exit. Make your highest and best offer. Wont last long!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,931
Status:
NEW LISTING
MLS#:
V4952171
Type:
Single Family
Subdivision:
WINTER PARK MANOR
Lot size:
0.76 Acres
Year built:
1959
A broker reciprocity listing Courtesy: RISE REALTY OF FLORIDA LLC 386-804-4114
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ADDITIONAL INFORMATION

WELCOME TO WINTER PARK LIVING! Situated on an expansive 0.76-acre lot in the established Winter Park Manor neighborhood, this charming 3-bedroom, 2-bathroom home offers a wonderful combination of space, comfort, and a peaceful waterfront setting. With approximately 250 feet of frontage along the small body of water identified as Lake Vella, the property provides a scenic backdrop and plenty of room to enjoy the outdoors. Inside, you'll find 1,440 square feet of heated living space featuring an open floor plan, vaulted ceilings, and a spacious living and dining area. The kitchen offers granite countertops, stainless steel appliances, ample storage, and a convenient breakfast bar. The primary bedroom includes its own en-suite bathroom. Step outside to the screened rear porch, where you can unwind and enjoy the surrounding greenery and water views. The generous lot offers plenty of possibilities for outdoor activities, gardening, or simply enjoying the extra space. Additional features include a one-car carport, central air conditioning, and NO HOA fees. Conveniently located near Winter Park's shopping, dining, parks, and everyday amenities, this property offers a unique opportunity to enjoy a spacious lot in a desirable Central Florida location. Schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,380
Status:
NEW LISTING
MLS#:
2173466
Type:
Single Family
Subdivision:
Eastbrook
Lot size:
0.26 Acres
Year built:
1962
Courtesy: BEYCOME OF FLORIDA LLC 804-656-5007
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ADDITIONAL INFORMATION

Welcome to this beautifully updated single-family pool home situated on a desirable corner lot! Featuring an expansive front yard and a spacious backyard, this property has plenty of room for outdoor enjoyment and entertaining. Inside, you'll find wood laminate flooring throughout, a spacious family room, and an updated kitchen featuring granite countertops, stainless steel appliances, and ample cabinetry. Enjoy the large pool and screened patio, great for relaxing or hosting gatherings. Additional highlights include a dedicated laundry room and generous outdoor space.

Beds:
11
Baths:
8.00
Sq.Ft.:
4,603
Status:
NEW LISTING
MLS#:
B26099444
Type:
Residential
Subdivision:
WINTER PARK (A/67 & B/86 & MISC 3/220)
Lot size:
0.5 Acres
Year built:
1929
Courtesy: Easy Realty 321-270-3388
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ADDITIONAL INFORMATION

Designed by renowned architect James Gamble Rogers II, 617 N Interlachen Ave presents a rare opportunity to own and thoughtfully reimagine a distinctive Spanish Revival estate in the heart of Winter Park. Built in 1929, renovated in 1981, and featuring extensive roof updates completed in 2020 and 2021, this character-filled property reflects the timeless architectural appeal that makes Winter Park so special. Situated on approximately half an acre, the estate includes a main residence plus three accessory buildings encompassing approximately 6,354 square feet combined, providing an exceptional amount of space and flexibility to create a property tailored to your lifestyle and vision.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,720
Status:
NEW LISTING
MLS#:
O6456614
Type:
Single Family
Subdivision:
LAKE KILLARNEY SHORES
Lot size:
0.14 Acres
Year built:
2024
A broker reciprocity listing Courtesy: PLATINUM REALTY GROUP FLORIDA INC 407-270-7378
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ADDITIONAL INFORMATION

Experience elevated living in this exceptional two-story Winter Park residence featuring 4 bedrooms and 4.5 bathrooms, custom designed with comfort, style, and entertaining in mind. Enjoy your own private outdoor oasis with a heated wading pool and outdoor kitchen with a gas grill, sink and two refrigerated drawers, perfect for relaxing or hosting family and friends year-round. Mature podocarpus line the outdoor space for added privacy. The luxurious primary suite offers a spa-inspired steam shower, along with custom closets and beautifully appointed custom vanities. The kitchen features custom cabinetry with both electric and manual operating cabinets, built-in coffee/espresso maker and walk in pantry adding a distinctive touch of convenience and functionality. Additional highlights include a Ring camera security system and a professionally coated garage floor. A rare opportunity to enjoy access to the private waters of Lake Killarney, adding an extra element of lifestyle and recreation. This exceptional home combines stylish features, indoor comfort, and outdoor entertaining in a desirable Winter Park location.

Beds:
4
Baths:
6.00
Sq.Ft.:
3,349
Status:
NEW LISTING
MLS#:
O6450302
Type:
Single Family
Subdivision:
WINTER PARK VILLAGE
Lot size:
0.18 Acres
Year built:
2026
A broker reciprocity listing Courtesy: ONE LUXURY INTERNATIONAL LLC 407-312-8003
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ADDITIONAL INFORMATION

A striking modern façade introduces this exceptional new residence by SoulTech Homes, where bold architectural expression meets beautifully considered interiors. Distinguished by extensive custom millwork, sophisticated paneling, and integrated LED lighting, the home delivers a level of detail and finish rarely found at this price point. An intelligently designed floor plan balances dramatic gathering spaces creating a home equally suited to memorable entertaining and effortless everyday living. At the heart of the residence, a spectacular double-height living room makes an unforgettable impression. A soaring paneled feature wall, accented by ambient LED lighting and a custom entertainment center, brings depth, texture, and architectural presence to the space. The kitchen pairs White Paradise quartz countertops with custom cabinetry and a full suite of Thermador appliances. Designed to be as functional as it is beautiful, this culinary centerpiece is complemented by a wine bar featuring a wine refrigerator and display shelving illuminated with integrated LED lighting. A spacious walk-in pantry and mudroom area adds exceptional everyday convenience. A downstairs guest suite offers comfortable accommodations, while a dedicated office provides a refined setting for working from home. Upstairs, the primary suite becomes a private sanctuary. An expansive dressing room complements the retreat, while the luxurious bath invites relaxation with a freestanding soaking tub, dual vanities, and a generous walk-in shower. Two additional upstairs bedrooms each enjoy it's own bathroom, and a conveniently positioned laundry room completes the upper level. The backyard is designed for entertaining. Approx. 900 SF of outdoor living space flows straight from the main living area, anchored by a 201 SF covered patio for shaded dining and gatherings in any weather. Around it, a 702 SF pool deck frames a heated 12' x 24' pool, with plenty of room for loungers, a dining table, and guests spilling out from the house. A full summer kitchen turns the backyard into a true outdoor room, so hosting a dinner party or a weekend pool day feels like a natural extension of the home. A metal roof, and enhanced landscaping complete the property’s polished presentation. The location adds another compelling dimension. Set within an evolving neighborhood experiencing an exciting wave of new construction, the home places you close to Park Avenue’s celebrated shops and restaurants, within walking distance of the Winter Park Racquet Club, and near the Maitland Art Center and Phelps Park. From its commanding first impression to its thoughtfully appointed private spaces, this residence offers a distinctive expression of modern luxury, bringing together architectural drama, exceptional craftsmanship, and the ease of Winter Park living.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,551
Status:
NEW LISTING
MLS#:
O6456425
Type:
Single Family
Subdivision:
WRENWOOD UNIT 3 4TH ADD
Lot size:
0.21 Acres
Year built:
1983
A broker reciprocity listing Courtesy: HOMEVEST REALTY 407-897-5400
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ADDITIONAL INFORMATION

Virtually Staged. Welcome to this beautifully maintained and extensively updated split-plan home with NO HOA in desirable Winter Park! Featuring 3 bedrooms and 2 bathrooms, this home sits on a beautifully manicured lot with a fantastic floor plan designed for both comfortable everyday living and entertaining. The home boasts a completely remodeled kitchen in (2026), featuring updated finishes and a fresh, modern feel, along with new flooring (2026), bathroom upgrades (2026), and new appliances (2024). Additional improvements include a new roof (2021), new water heater (2025), and Solar Tubes a compact, energy-efficient system that channels natural daylight from your roof that bring in extra natural light, creating a bright and welcoming atmosphere. The popcorn ceilings have been removed and replaced with an updated drop-down ceiling finish, adding to the home's refreshed look. Fresh exterior paint (2024) provides even more curb appeal! Separate formal living and dining rooms offer wonderful spaces for entertaining, while the spacious kitchen with breakfast bar opens to the family room, making it the perfect gathering spot for family and friends. The generous owner's suite features a double closet and private en-suite bath. Two additional spacious bedrooms offer flexibility for family, guests, a home office, or a playroom. Step outside and enjoy your own fully fenced backyard oasis! Entertain on the oversized covered lanai with ceiling fan, or enjoy the beautiful mature trees and fruit trees throughout the property. A NEW storage shed added in 2025 provides even more room for tools, hobbies, and outdoor equipment. Additional features include an irrigation system, whole-house water softening system, double-pane windows, and storm shutters for added peace of mind during Florida's storm season. Conveniently located just 10 minutes from downtown Winter Park, with easy access to I-4 and 417, this home offers the perfect combination of comfort, convenience, and thoughtful updates. Zoned for highly rated Seminole County schools, this is a wonderful opportunity to own a move-in-ready home with so many major improvements already completed!

Beds:
2
Baths:
2.00
Sq.Ft.:
858
Status:
NEW LISTING
MLS#:
O6456509
Type:
Single Family
Subdivision:
PARK AIRE CONDO
Year built:
1955
A broker reciprocity listing Courtesy: MICHAEL O'SHAUGHNESSY, INC. 407-539-4844
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ADDITIONAL INFORMATION

renovated 2 years ago new AC and air vents, downtown Winter Park living at its best, iconic Park Aire condominiums, auto window shades built in, new kitchen - association approval - laundry is on 3rd floor or basement

Beds:
3
Baths:
3.00
Sq.Ft.:
4,173
Status:
NEW LISTING
MLS#:
O6455524
Type:
Single Family
Subdivision:
KENILWORTH SHORES
Lot size:
0.26 Acres
Year built:
1955
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

Virtually Staged. OUTSTANDING OPPORTUNITY!! Delightful 2,626 sq ft home, perfectly positioned on a charming corner lot in the vibrant 32789 neighborhood! With its array of newly constructed homes nearby, this well-cared-for property stands as a fantastic blank canvas, just waiting for your creative touch. The updated kitchen boasts modern cabinets, chic countertops, and stainless steel appliances, complete with a cozy breakfast nook to enjoy your morning coffee. Entertain in style in the formal dining room or gather around the fireplace in the living room. The original primary suite, alongside a guest bedroom and bathroom, features exquisite parquet floors and beautiful crown molding that add a touch of elegance. Imagine hosting friends in the spacious family room, adorned with beamed ceilings, or retreating to the incredible second-story master suite, where an impressive 18x12 bathroom, huge walk-in closet, and private 31x9 balcony await, all overlooking a charming, landscaped backyard. Step outside to enjoy the roomy L-shaped covered porch and take advantage of the two separate garages (24x23 & 22x14) plus a gated side yard perfect for storage (NO HOA!)—completing this exceptional offering! This home is zoned for the highly regarded Brookshire Elementary, Glenridge Middle, and Winter Park High, plus the delightful shops and dining along Winter Park’s Park Avenue are just a short drive away. Don’t miss your opportunity to make this enchanting home yours! WELCOME HOME!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,810
Status:
NEW LISTING
MLS#:
O6456440
Type:
Single Family
Subdivision:
FAIRBANKS SHORES 2ND ADD
Lot size:
0.19 Acres
Year built:
1955
A broker reciprocity listing Courtesy: COLDWELL BANKER REALTY 407-696-8000
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ADDITIONAL INFORMATION

Original hardwood floors, an updated kitchen, and a versatile bonus room highlight this three-bedroom, two-bath home with 1,511 heated square feet at 2885 Roxbury Road, Winter Park, FL 32789. A fenced backyard, outdoor deck, and practical system improvements complement the home’s original character. The kitchen features quartz countertops, stainless steel appliances, an island, and pantry cabinetry. Hardwood flooring extends throughout the main living spaces and bedrooms, with tile in the kitchen, bathrooms, and bonus room. Use the bonus room for additional seating, hobbies, or a home office while maintaining all three bedrooms. Cedar-lined closets in the primary bedroom and an additional bedroom provide a distinctive detail. Improvements include a roof installed in 2019, air conditioning replaced in 2020, an electrical panel replaced in 2021, and double-pane windows in the bedrooms. Additional updates include exterior paint, replacement front, back, and kitchen doors, and front and rear gutters. The backyard deck extends the living space outdoors, with room for dining, relaxing, or container gardening. A fenced yard and an private storage shed provide additional functionality. A carport, irrigation system, and available fiber-optic internet round out the features. The septic system was pumped in 2026. This Winter Park home combines hardwood floors, an updated kitchen, flexible bonus space, and outdoor living in one inviting property.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,937
Status:
NEW LISTING
MLS#:
O6455676
Type:
Single Family
Subdivision:
EASTGATE SUB
Lot size:
0.19 Acres
Year built:
1956
A broker reciprocity listing Courtesy: KELLER WILLIAMS REALTY AT THE PARKS 407-629-4420
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ADDITIONAL INFORMATION

**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.**Welcome to 1934 Taylor Avenue, a charming mid-century modern home offering 4 bedrooms and 1.5 bathrooms in Winter Park's established Eastgate neighborhood. Full of character and personality, this single-story home blends timeless design with comfortable everyday living. Hardwood floors throughout the main living areas add warmth and character, while the 1.5 bathrooms feature classic, colorful details that add a fun and distinctive charm. The kitchen makes its own statement with a pop of color on the cabinets and playful vinyl flooring. The open floor plan seamlessly connects the living and dining areas, creating an inviting space for relaxing and entertaining. The split-bedroom layout provides added privacy and flexibility for family members and guests. French doors lead to the backyard, creating a lovely connection between indoor and outdoor living. A welcoming front porch offers a cozy spot to enjoy your morning coffee. The private backyard provides plenty of space for outdoor activities and relaxation, with a spacious deck perfect for gatherings and an open patio offering additional room for outdoor seating. Conveniently located near Aloma Avenue, this home offers easy access to shopping, dining, parks, and everyday essentials. Nearby destinations include the Winter Park YMCA, Rollins College, and Downtown Winter Park's popular Park Avenue, known for its boutique shops, restaurants, and entertainment. With its mid-century modern character, colorful details, versatile outdoor spaces, and convenient location, 1934 Taylor Avenue offers a unique opportunity to enjoy Winter Park living.

Beds:
2
Baths:
2.00
Sq.Ft.:
970
Status:
NEW LISTING
MLS#:
O6452921
Type:
Single Family
Subdivision:
ANDALUCIA APTS
Lot size:
0.61 Acres
Year built:
1972
A broker reciprocity listing Courtesy: FANNIE HILLMAN & ASSOCIATES 407-644-1234
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ADDITIONAL INFORMATION

LOCATION, LOCATION, LOCATION! Just Steps from Winter Park’s Famed Park Avenue! Enjoy the best of Winter Park living in this delightful two-bedroom, two-bath condominium, ideally situated on the top floor of a charming, intimate complex. Offering peaceful treetop views, this inviting residence features a spacious living area, crown molding, an updated kitchen, and a private screened porch, perfect for enjoying your morning coffee or relaxing in the evening. The beautifully appointed kitchen showcases rich wood cabinetry, generous countertop space, and abundant storage. The spacious primary bedroom provides a comfortable retreat, while the second bedroom features its own en-suite bath, ideal for guests or flexible living arrangements. Additional conveniences include an assigned covered carport space and a separate storage closet. Residents of this quaint community enjoy a tranquil courtyard, outdoor patio, and spacious community laundry room. The location is truly exceptional! Just one block from Winter Park's renowned Park Avenue, you'll enjoy an incredible selection of boutique shopping, sidewalk cafés, fine dining, museums, Central Park, and convenient train service. Located steps from the Winter Park Nine Golf Course and a short stroll to The Alfond Inn and Rollins College, everything that makes Winter Park special is right at your doorstep. An incredible opportunity to enjoy the coveted Park Avenue lifestyle in one of Winter Park's most desirable locations! A/C: 2016, Water Heater 2021, Roof on Complex completed in 2024.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,548
Status:
NEW LISTING
MLS#:
O6456240
Type:
Single Family
Subdivision:
PELICAN BAY
Lot size:
1.2 Acres
Year built:
1985
A broker reciprocity listing Courtesy: ABSOLUTE REALTY GROUP, LLC 407-673-1400
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ADDITIONAL INFORMATION

Awesome 5 bedroom 3.5 bathroom custom built home on gorgeous 1.2 acre WATERFRONT cul-de-sac lot in lovely Pelican Bay of Winter Park. A True Gem on the Lake on a private dead-end street! Step through the front door and into a welcoming foyer with beautiful wood floors and oversized living and family rooms featuring dual wood-burning fireplaces. 4 BRAND NEW CUSTOM BAY WINDOWS (NOV 2026) installed in living room. The gourmet kitchen features classic oak cabinetry and upgraded granite counters, as well as BRAND NEW STAINLESS STEEL SIDE BY SIDE REFRIGERATOR (NOV 2026). Kitchen bay windows overlook massive screened rear porch, screened pool oasis, and breathtaking backyard waterfront views of Lake Florence. Main bedroom is downstairs and features large ensuite bathroom with dual sinks, garden tub, and walk in shower. Additional 4 bedrooms and 2 full bathrooms as well as bonus room are located upstairs and enjoy wonderful lakefront views. BRAND NEW ROOF INSTALLED NOV 2021. This oversized lot contains a variety of wonderful fruit trees and edible plants located around the property including avocado, purple yam, lychee, chinese chives, jujube, apple cactus, persimmon, mango, and dragon eye. The lake frontage speaks for itself, but as you can imagine the sunsets are truly superb. The Winter Park location is one of the best, close to shopping, schools, major roads, international airport, and amazing restaurants. Bring your buyers so they can make this beautiful custom home their own.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,474
Status:
NEW LISTING
MLS#:
O6456258
Type:
Single Family
Subdivision:
TIMBERLANE
Lot size:
0.36 Acres
Year built:
1957
A broker reciprocity listing Courtesy: SHAWFIELD REALTY GROUP 888-650-5553
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ADDITIONAL INFORMATION

WINTER PARK LUXURY LIVING! Welcome to 647 Randy Lane, where timeless elegance meets modern sophistication in one of Winter Park's most desirable locations! Offered for the first time in over a decade, this beautifully maintained residence is situated on an expansive 0.36-acre corner lot, surrounded by lush, mature landscaping and designed for exceptional Florida living. Step inside to discover a spacious, open-concept, floor plan that effortlessly blends comfort, style, and functionality. At the heart of the home is a stunning chef's kitchen featuring gorgeous quartz countertops, premium Wolf double ovens, and a built-in Sub-Zero refrigerator—perfect for everyday living and entertaining alike. Your private backyard oasis awaits! Enjoy an oversized swimming pool, expansive patio, and generous green space, all surrounded by tropical landscaping that creates a peaceful, resort-style atmosphere. Thoughtful outdoor lighting sets the stage for evening entertaining, while the seamless indoor-outdoor flow makes this home ideal for enjoying Florida's beautiful weather year-round. Impressive upgrades and features include a NEW ROOF (2024), SOLAR PANELS (2022), resurfaced pool and updated pool tile (2021), tankless gas water heater, well irrigation system, and an oversized indoor laundry room. LOCATION, LOCATION, LOCATION! Just minutes from Winter Park's iconic Park Avenue, you'll enjoy convenient access to exceptional dining, boutique shopping, beautiful parks, and cultural attractions. The property is also zoned for sought-after schools, including Audubon K-8 and Winter Park High School. Buyers should verify current school assignments. Luxury, privacy, and an unbeatable Winter Park lifestyle—all in one exceptional property! Don't miss this rare opportunity to make 647 Randy Lane your next home.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,069
Status:
NEW LISTING
MLS#:
O6456091
Type:
Single Family
Subdivision:
QUARTERS AT WINTER PARK CONDO
Lot size:
0.54 Acres
Year built:
1981
A broker reciprocity listing Courtesy: CHEVON EATON 321-210-4633
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ADDITIONAL INFORMATION

Renovated in 2022, this 3-bedroom, 2.5-bath home offers 2,069 square feet of bright, modern living space. The open main level connects the living area, dining space, and kitchen, which has stainless steel appliances and sleek contemporary cabinetry. A fireplace anchors the living room, and large windows bring in natural light throughout. Upstairs, the oversized primary suite gives you room to spread out, with two more bedrooms for guests, a home office, or flexible space. Step outside to a private courtyard with a outdoor kitchen, a quiet place for morning coffee or evening dinners . A 2-car garage with electric car charger and large driveway complete the package. Roof replacement Jan 2027. 5-minute walk to Rollins College and 10 minutes on foot to Park Avenue’s shops, restaurants, and Saturday farmers market. You can leave the car in the garage.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,070
Status:
NEW LISTING
MLS#:
O6455299
Type:
Single Family
Subdivision:
BEL AIRE PINES
Lot size:
0.17 Acres
Year built:
1981
A broker reciprocity listing Courtesy: MID-STATE PROPERTIES PSL LLC 561-843-9537
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ADDITIONAL INFORMATION

This home is move-in ready! One year old new roof installed which comes with a four (4) year warranty which covers all repairs. The interior was recently painted down to the baseboards and primary and guest bathrooms have been completely renovated. Orion Modern Flames Traditional Insert Fireplace Heater has been installed which can heat the living areas of the home in the winter! Brand new kitchen appliances include refrigerator, stove, microwave and dishwasher as well as new garbage disposal. There is a large two car garage with laundry area and driveway can accommodate additional cars. Home is completely fenced in for safety. All systems of this home have been WELL maintained. Too many updates to mention. Excellent location in Winter Park, close to schools and shopping. Take a look!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,950
Status:
NEW LISTING
MLS#:
S5160711
Type:
Single Family
Subdivision:
GREENVIEW AT WINTER PINES
Lot size:
0.22 Acres
Year built:
1981
A broker reciprocity listing Courtesy: LPT REALTY 877-366-2213
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ADDITIONAL INFORMATION

Virtually Staged. Perfectly positioned on the 13th tee box and 16th fairway of the Winter Park Pines Golf Course, this home sits on an corner lot and offers a rare opportunity to create your dream home while enjoying breathtaking golf course views.  **The current floor plan features three bedrooms, as the original fourth bedroom has been converted into an expansive walk-in closet for the primary suite, Featuring over 2,000 square feet of single-story living space, this home has been extensively renovated throughout the interior, offering the charm of an established Winter Park neighborhood with the comfort and appeal of modern finishes. Step inside to discover new luxury vinyl flooring, beamed ceilings, modern fireplace. Brand new kitchen appliances with modern grey cabinetry, crown molding and white quartz counter tops.  Step outside to your own private backyard retreat, complete with a 30x11 covered patio and screen-enclosed swimming pool overlooking the lush fairways of WP18. Whether enjoying your morning coffee, entertaining guests, or simply relaxing poolside, this outdoor living space offers a peaceful setting that’s increasingly difficult to find in Winter Park. Additional highlights include a NEW ROOF (NOVEMBER 2024), New pool pump, resurfaced pool with new pavers surrounding,  a large indoor laundry room and no HOA. Located just a few doors from the Cady Way Trail on one of the neighborhood's most picturesque oak-canopied streets, the setting is truly exceptional. This is a rare opportunity to purchase a home set directly on one of Winter Park's premier golf courses, where major mechanical system upgrades and costly infrastructure improvements have already been completed, creating the perfect opportunity to transform the interior into your own custom vision. This is move in ready so schedule your showings today!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,005
Status:
NEW LISTING
MLS#:
O6455726
Type:
Single Family
Subdivision:
OLYMPIA HEIGHTS ANNEX
Lot size:
0.21 Acres
Year built:
1955
A broker reciprocity listing Courtesy: CORCORAN PREMIER REALTY 407-965-1155
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ADDITIONAL INFORMATION

Welcome to Dubstread Heights. This in-town community is perfect for the busy professional that needs access to downtown, college park or Winter Park. Located just 1 block from the back side of Dubstread Golf Course grab your golf cart for an afternoon round. This renovated home just received a New Roof, as well as paint in and out. Solid hard-wood flooring greets you upon entry. An open floor plan with vaulted ceilings offers a grand theme throughout the home. A spacious living space is joined by a breakfast bar and opens to the newly updated kitchen. New designer porcelain tile flooring, with newer cabinetry sets the stage for the Cafe and Subzero appliances. Stone countertops add to the designer feel. Just off of the kitchen is a flex space that could be a dining/office area. A stained-glass French door opens to a covered/screened rear porch and looks out onto the private fenced back-yard. Back inside, the two bedrooms are in a split fashion with new paint, ceiling fans, and a closet organizer in the primary bedroom. The bath has updated fixtures/lighting and features a stone travertine shower enclosure. The property is quite private as there are no homes across the street and is maintained by the City. This quaint home is ready to be enjoyed by its new owners.... please set you appointment soon...

Beds:
3
Baths:
3.00
Sq.Ft.:
2,846
Status:
NEW LISTING
MLS#:
O6455137
Type:
Single Family
Subdivision:
MORSELAND SUB
Lot size:
0.19 Acres
Year built:
1994
A broker reciprocity listing Courtesy: PREMIER SOTHEBY'S INTL. REALTY 407-644-3295
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ADDITIONAL INFORMATION

Under contract-accepting backup offers. Charming, sophisticated, and ideally situated in downtown Winter Park, this inviting one-story residence offers an appealing blend of timeless character, thoughtful updates, and exceptional versatility. A picturesque façade, meticulous landscaping, and welcoming front entrance set the tone, opening to a sunlit foyer and an expansive living and gathering room anchored by a gas fireplace. Generously proportioned, the space easily accommodates two distinct seating areas, creating an ideal setting for both everyday living and entertaining. Beautiful wood floors and plantation shutters extend throughout the home, complementing the open floor plan and warm, refined interiors. The updated kitchen features integrated Viking appliances and Sub Zero refrigeration, a built-in oven and microwave, and a gas range, with a charming breakfast nook complete with built-in seating. Adjacent to the kitchen, the spacious dining area enjoys peaceful views of the rear courtyard patio through French doors, creating a natural connection between indoor and outdoor living. The thoughtfully designed tri-split floor plan provides excellent separation and privacy. Double doors introduce the primary suite, which features an updated bath with a generous glass-enclosed walk-in shower and a walk-in closet. The second bedroom also offers a walk-in closet and en-suite bath, while the third bedroom, currently utilized as an office, is conveniently positioned near a Jack-and-Jill bath. Additional flexibility is found above the attached two-car garage, where a staircase leads to a spacious, air-conditioned flex room (not included in the heated square footage) offering endless possibilities as a home office, fitness studio, game room, or art loft. The garage is discreetly positioned at the rear of the residence and accessed via the community's private driveway. An exceptional downtown Winter Park location places the boutiques, restaurants, sidewalk cafés, and cultural attractions of Park Avenue just a short stroll or bike ride away. A wonderful opportunity to enjoy the character, convenience, and walkable lifestyle that make Winter Park so desirable.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,996
Status:
NEW LISTING
MLS#:
O6454832
Type:
Single Family
Subdivision:
AUTUMN GLEN PH 1
Lot size:
0.13 Acres
Year built:
1986
A broker reciprocity listing Courtesy: RE/MAX TOWN & COUNTRY REALTY 407-695-2066
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ADDITIONAL INFORMATION

Virtually Staged. More photos coming soon! YOUR FLORIDA DREAM LIFESTYLE STARTS HERE! Welcome to 1735 Meadowgold Lane in the desirable Autumn Glen community! This beautifully updated pool home combines modern style, comfortable living, and the outdoor lifestyle Florida is famous for. Step inside and discover soaring ceilings, skylights, beautiful flooring, and a stunning white marble wood-burning fireplace. The renovated kitchen is a showstopper, featuring crisp white and frosted-glass cabinetry, Blue Moon granite countertops, a contemporary glass backsplash, and stainless steel appliances. Need extra space? The spacious, climate-controlled bonus room offers endless possibilities for a home office, gym, media room, or additional living area. Enjoy beautifully updated bathrooms, including a primary suite with a double vanity and elegant marble-accented, glass-enclosed shower as well as a spacious walk in closet in the primary suite and an oversized walk in closet in the bonus room. Your private backyard oasis awaits! Relax in the screened-in pool, entertain on the spacious covered patio, or enjoy the privacy of your fully fenced backyard. BIG UPDATES. BEAUTIFUL LIVING. PEACE OF MIND. Major improvements include: - 2019 Roof and skylight - 2019 Pool resurfaced - 2022 New Windows - 2023 Whole-house repiping, Updated flooring, New HVAC - 2026 New pool pump This is Move-in ready home, located in the established Autumn Glen Community, featuring sidewalks, tennis/pickleball courts and a neighborhood playground. Plus, you're zoned for top rated Seminole County schools.

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Andrea Conner, License #BK3437731, Xome Inc., License #1043756, [email protected], 844-400-9663, 750 State Hwy 121 Bypass, Suite 100, Lewisville, TX 75067


Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of {{last updated}}. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Properties displayed may be listed or sold by various participants in the MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Copyright 2026, My Florida Regional MLS DBA Stellar MLS.

Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange (IDX) program of the Northeast Florida Multiple Listing Service, Inc. Real estate listings held by brokerage firms other than the owner of this site are marked with the listing broker's name and detailed information about such listings includes the name of the listing brokers. Data provided is deemed reliable but is not guaranteed. Copyright 2026 Northeast Florida Multiple Listing Service, Inc. All rights reserved.
Andrea D. Conner, License # BK3437731, Xome Inc., License CQ1043756, [email protected], 844-400-XOME, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

All listings featuring the BMLS logo are provided by BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2026 BeachesMLS, Inc.




Winter Park Real Estate

Winter Park is located in Florida. Winter Park, Florida has a population of 29,672. Winter Park is less family-centric than the surrounding county with 27.95% of the households containing married families with children. The county average for households married with children is 31.51%.

The median household income in Winter Park, Florida is $88,688. The median household income for the surrounding county is $65,784 compared to the national median of $69,021. The median age of people living in Winter Park is 45.3 years.

Winter Park Weather

The average high temperature in July is 92 degrees, with an average low temperature in January of 49.4 degrees. The average rainfall is approximately 51.9 inches per year, with 0 inches of snow per year.

Winter Park Map

Winter Park Real Estate Market Conditions

  • Median sales price

    $524,250
    25.3%
    change since last quarter
  • # Active listings

    509
    30-day change

Winter Park Schools and Demographics

Education near Winter Park, FL

City County
High School Graduates 96.78 89.47
College Degree - 2 year 9.01 11.45
College Degree - 4 year 62.48 35.7
Graduate Degree 17.77 9.12
Expenditures per Student 12,701 12,701
Students per Teacher 17.3 17.3

Elementary Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Aloma Elementary School PK - 05 528 15.5 32792
Aspire Academy Charter KG - 05 111 8.5 32804
Audubon Park Elementary School PK - 05 1,182 14.8 32814
Brookshire Elementary School PK - 05 632 12.9 32792
Dommerich Elementary School PK - 05 603 15.1 32751
Eastbrook Elementary School PK - 05 809 14.2 32792
Fern Creek Elementary School PK - 05 326 12.1 32803
Hillcrest Elementary School PK - 05 463 14.5 32803
Hungerford Elementary School PK - 05 283 13.5 32751
Killarney Elementary School KG - 05 444 14.8 32789
Lake Silver Elementary School PK - 05 688 12.3 32804
Lake Sybelia Elementary School PK - 05 600 13.3 32751
Lakemont Elementary School KG - 05 656 14.6 32792
Orlando Science Elementary Charter KG - 05 482 15.1 32804
Princeton Elementary School PK - 05 488 13.2 32804

Middle Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Glenridge Middle School 06 - 08 1,415 18.4 32814
Maitland Middle School 06 - 08 909 18.9 32751
Robert E Lee Middle 06 - 08 1,034 17.2 32804

High Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
Edgewater High School 09 - 12 1,782 20 32804
Lake Howell High School 09 - 12 2,229 19.1 32792
Winter Park High School 09 - 12 3,069 18.7 32792
Workforce Advantage Academy Charter 09 - 12 238 47.6 32803

Ungraded Schools near Winter Park, FL

Grades Students P/T Ratio ZIP
* Aloma High Charter School 09 - 12 510 42.5 32792
* Winter Park Education Center 11 - 12 0 32789
Broward Science Charter School UG - UG 0 32804
Central Florida Leadership Academy Charter 06 - 12 189 15.8 32803
Gateway 06 - 12 63 3.7 32804
Hospital Homebound PK - 12 229 4 32804
La Amistad School KG - 12 48 9.6 32751
Orlando Science Middle High Charter School 06 - 12 555 15.4 32804
Pace Center for Girls 06 - 12 34 6.8 32803
Silver Star Center 06 - 12 25 2.5 32804
Winter Park Tech AE - AE 0 32789

Demographics near Winter Park, FL

City County
Neighborhood Type Suburban
Population 29,672 1,409,949
Population Density 3,393 1,562
Median Age 45.3 35.7
People per Household 2.3 2.9
Median Household Income 88,688 65,784
Average Income per Capita 67,032 33,498

Real estate near Winter Park