Winter Park, FL Homes for Sale with Garage

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  $1,099,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 3.5 Baths
  • 2,193 Sq Ft

  1768 Mondrian Cir, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. Step into refined lakeside living at the exclusive Lake Killarney Townhomes, where contemporary elegance meets everyday convenience. This ultra-private corner unit boasts one of the community’s most desirable floor plans—perfectly positioned in a peaceful enclave just steps from the vibrant heart of Winter Park Village and mere minutes from I4,

  Brandon Geers COMPASS FLORIDA LLC

  1768 Mondrian Cir, Winter Park, FL 32789
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  $585,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,818 Sq Ft

  1809 Hammerlin Ave, Winter Park, FL 32789

  Highly coveted Winter Park! 40+ Pictures! This stunning 2-story end unit offers the epitome of modern convenience and elegant living; this residence provides the ideal "lock and go" lifestyle. Step through the charming covered front porch into the inviting open living area, adorned with abundant natural light, gleaming real wood flooring, and exquisite crown molding. Hosting gatherings is

  Edward Rice NICOLE-HUDSON REALTY CORP

  1809 Hammerlin Ave, Winter Park, FL 32789
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  $1,634,900 Open Fri 2PM - 6PM

  • 5 Beds
  • 4.5 Baths
  • 3,252 Sq Ft

  1510 Miller Ave, Winter Park, FL 32789

  New Construction – JUST COMPLETED! Discover Modern Luxury in Winter Park's Latest Neighborhood, Winter Park Grove! Step into a world of refined living with this breathtaking new construction pool home, located in the vibrant heart of Winter Park. Just moments away from the eclectic energy of Park Avenue, this modern masterpiece seamlessly blends sophistication, style, and convenience — all within

  Kimberly Griffin RE/MAX EXCLUSIVE COLLECTION

  1510 Miller Ave, Winter Park, FL 32789
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  /2

  $1,495,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 2,756 Sq Ft

  905 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. Ideally located within walking distance to Park Avenue and historic Old Winter Park, this exclusive neighborhood blends timeless character with modern luxury. The

  Matthew Burks CORCORAN PREMIER REALTY

  905 Enclave Place, Winter Park, FL 32792
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  $2,200,000 Open Sun 1AM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 3,472 Sq Ft

  2423 Via Sienna, Winter Park, FL 32789

  Welcome to 2423 Via Sienna, gracefully positioned on a quiet cul-de-sac in the heart of Winter Park. This charming, established enclave is just moments from the Winter Park Racquet Club, Phelps Park, the YMCA, and the renowned boutiques and dining of Park Avenue.This exceptional four-bedroom, three-and-a-half-bath pool residence has been taken to the studs and masterfully reimagined with

  Wendy Williams Crumit FANNIE HILLMAN & ASSOCIATES

  2423 Via Sienna, Winter Park, FL 32789
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  /20

  $362,000

  • 3 Beds
  • 2.5 Baths
  • 1,872 Sq Ft

  7474 Aloma Pines Ct, Winter Park, FL 32792

  ***PRICE REDUCTION*** **Seller offering closing credit**Nestled on a quiet cul-de-sac in desirable Winter Park, this well-maintained home offers a thoughtful layout with bright, open living spaces designed for both comfort and everyday living. The kitchen flows seamlessly into the main living and dining areas, making it ideal for gathering and entertaining. Generously sized bedrooms provide

  Jakki Kim OAK HOLLOW PROPERTIES

  7474 Aloma Pines Ct, Winter Park, FL 32792
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  /18

  $4,199,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,891 Sq Ft

  1417 Williams Dr, Winter Park, FL 32789

  Under Construction. Tucked away on a quiet cul-de-sac in the coveted Park Grove community, this home sits on an expansive 0.37-acre lot, just moments from the boutiques, dining, and charm of Park Avenue. The exterior makes a striking first impression with a refined architectural façade that feels both timeless and distinctive. Inside, a dramatic 20-foot foyer welcomes you with abundant natural

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1417 Williams Dr, Winter Park, FL 32789
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  $575,000

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

  1781 Indiana Ave Unit A, Winter Park, FL 32789

  Welcome to 1781 Indiana Avenue, Unit A, a beautifully appointed three-bedroom, two and a half bathroom townhouse nestled in the heart of Winter Park. This inviting residence offers the perfect blend of comfort and convenience, featuring a spacious two-car garage and a private courtyard ideal for morning coffee, outdoor dining, or relaxing in the Florida sunshine. Inside, the thoughtfully designed

  James Rouadi CARLISLE REALTY, LLC

  1781 Indiana Ave Unit A, Winter Park, FL 32789
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  /18

  $650,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  1760 Greenwich Ave, Winter Park, FL 32789

  Fabulous Winter Park location. This is a 3 bedroom, 2 bath patio home with a great layout, split bedroom plan, high ceilings in the living room, and an eat in kitchen that is open to the family room. A large primary bedroom which has a walk in closet, two additional closets and french doors leading out to the back yard. There is a screened in patio off of the breakfast / dining area and an

  Meg Dolan FANNIE HILLMAN & ASSOCIATES

  1760 Greenwich Ave, Winter Park, FL 32789
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  /9

  $1,595,000

  • 3 Beds
  • 2 Baths
  • 2,012 Sq Ft

  1113 Via Del Mar, Winter Park, FL 32789

  Exceptional opportunity in the heart of Winter Park — a truly premier and irreplaceablehomesite offering rare scale, privacy, and extraordinary future build potential. The primaryvalue is in the land, presenting an unparalleled canvas for a custom luxury residence, withvirtually no comparable vacant land available in the immediate vicinity. Set on a tranquil smalllake that

  David Barany BAY HILL REALTY LLC

  1113 Via Del Mar, Winter Park, FL 32789
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  $500,000 Open Sat 1:30PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,413 Sq Ft

  512 N Lakemont Ave, Winter Park, FL 32792

  Set on an oversized corner lot in one of the most desirable pockets of Winter Park, this 3-bedroom, 2-bath pool home blends character, location, and opportunity.The backyard is a standout feature, with a resurfaced pool finished in Tahoe Blue PebbleTec and positioned for open sky views, a rare find in a neighborhood known for its mature tree canopy. It creates a bright, inviting outdoor space

  David Plasencia COLDWELL BANKER REALTY

  512 N Lakemont Ave, Winter Park, FL 32792
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  $875,000 Open Sat 12PM - 3PM

  • 4 Beds
  • 3 Baths
  • 2,509 Sq Ft

  668 Overspin Dr, Winter Park, FL 32789

  One or more photo(s) has been virtually staged. A contemporary, beautifully finished home offering standout value in one of Winter Park’s most coveted zip codes. With more than 2,500 square feet of bright, open living space, this property features a sleek fireplace, a large pantry area, a designer kitchen, and a massive two-car garage. The private primary suite sits upstairs along with additional

  Kris Kennedy COMPASS FLORIDA LLC

  668 Overspin Dr, Winter Park, FL 32789
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  /30

  $430,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,727 Sq Ft

  1914 Bonanza Ct, Winter Park, FL 32792

  SELLER MOTIVATED! Get ready to fall in love with this stunning Winter Park home! Tucked away in a peaceful cul-de-sac, this fully renovated 3-bedroom, 2-bath beauty blends modern style with everyday comfort. Step into the family room and instantly feel the openness of the bright, airy layout. The open floor plan creates a seamless flow from the living area to the brand-new kitchen, making the

  Linda Jokbengboon COMPASS FLORIDA LLC

  1914 Bonanza Ct, Winter Park, FL 32792
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  /19

  $450,000

  • 1 Bed
  • 1 Bath
  • 673 Sq Ft

  640 N Park Ave Unit 5, Winter Park, FL 32789

  Location, Location, Location!Charming first floor 1 bedroom, 1 bath condo ideally located on North Park Avenue in the retro-chic Park Aire complex. Beautifully overhauled in 2018 with quartz counters, new cabinetry, new appliances, custom mosaic kitchen detail, new flooring, new lighting, updated electrical, with picturesque views of the Winter Park Golf Course and Casa Feliz.Enjoy a

  David Auerbach PARK TOWN REAL ESTATE LLC

  640 N Park Ave Unit 5, Winter Park, FL 32789
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  $1,895,000 Open Sat 12PM - 3PM

  • 5 Beds
  • 4.5 Baths
  • 3,617 Sq Ft

  914 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. The Enclave is a premier, boutique community in the heart of Winter Park, featuring just 23 thoughtfully designed residences nestled beneath mature oak canopies, being built by FG Schaub Custom Homes. A short walk to Phelps Park, YMCA, dinner and shopping. Surrounded by natural beauty and designed with intention, The Enclave offers a rare opportunity to enjoy a

  Matthew Burks CORCORAN PREMIER REALTY

  914 Enclave Place, Winter Park, FL 32792
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  $400,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,518 Sq Ft

  3127 Ash Park Loop, Winter Park, FL 32792

  Beautifully renovated 3-bedroom, 2-bath home in sought-after Winter Park, just 15 minutes from Park Avenue and zoned for top-rated schools. Major updates include a 2024 HVAC and 2020 ROOF. From the moment you arrive, the fresh landscaping and large covered front porch invite you to slow down—ideal for relaxing or gatherings with friends. Inside, an open, light-filled layout unfolds with soaring

  George Reeter KELLER WILLIAMS WINTER PARK

  3127 Ash Park Loop, Winter Park, FL 32792
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  /32

  $675,000

  • 3 Beds
  • 2 Baths
  • 2,193 Sq Ft

  1427 Lake Florence Way, Winter Park, FL 32792

  Welcome to this beautifully maintained, Stunning Better-Than-New 6-Year-Old Custom Home in Gated Lake FlorencePreserve, one-owner custom home that truly has it all. From the moment you enter, you’ll appreciate the exceptional quality and craftsmanship, including upgraded 8' interior doors, 10-foot ceilings, crown molding, and elegant tray ceilings throughout—even in the primary suite. One of

  Doug Addeo COMMUNITY REALTY ASSOCIATES

  1427 Lake Florence Way, Winter Park, FL 32792
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  /15

  $2,385,000 New Construction

  • 5 Beds
  • 4.5 Baths
  • 3,408 Sq Ft

  1630 Elm Ave, Winter Park, FL 32789

  Under Construction. In the heart of Winter Parks highly coveted Tree Streets, where quiet tree-lined roads and timeless charm define the neighborhood, this stunning new construction by LUIH Homes offers a refined blend of modern architecture. The home immediately captivates with its bold contemporary façade and thoughtfully designed floor plan. Inside, elegant living spaces unfold intentionally,

  Christopher Christensen ONE LUXURY INTERNATIONAL LLC

  1630 Elm Ave, Winter Park, FL 32789
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  /5

  $3,795,000 New Construction

  • 5 Beds
  • 5.5 Baths
  • 4,508 Sq Ft

  1811 Oneco Ave, Winter Park, FL 32789

  Under Construction. One of Winter Park's largest new construction homesites — 13,519 square feet, over a third of an acre — anchors this signature build, a three-story luxury residence on Oneco Avenue where scale, privacy, and architectural distinction rarely coexist at this price point.This home carries the mark of a builder renowned for delivering Winter Park's most trend-setting luxury

  Ahmad Hassan COMPASS FLORIDA LLC

  1811 Oneco Ave, Winter Park, FL 32789
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  $649,000

  • 4 Beds
  • 2 Baths
  • 1,936 Sq Ft

  1523 Golfside Dr, Winter Park, FL 32792

  POOL HOME, nestled along the 14th fairway of Winter Park Pines Golf Course (WP18). A peaceful retreat with no rear neighbors—ideal for tranquility and privacy. Offering 1,936 square feet, four bedrooms, two bathrooms and an inside utility room, this is a hard-to-find gem in Winter Park. Perfectly situated in a tree-lined community overlooking the golf course. Upon entering, you are greeted by a

  Brian Cirillo BALDWIN PARK REALTY LLC

  1523 Golfside Dr, Winter Park, FL 32792
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  $3,450,000

  • 5 Beds
  • 6 Baths
  • 4,636 Sq Ft

  2040 Randall Cir, Winter Park, FL 32789

  Set along a picturesque brick street, 2040 Randall Circle is a beautifully crafted residence that pairs timeless architecture with elevated, designer finishes and a functional floor plan. Framed by manicured landscaping and connected to a detached two-car garage by a covered walkway, the home offers classic curb appeal in an idyllic setting just minutes from vibrant shopping and dining on Park

  Mick Night PREMIER SOTHEBY'S INTL. REALTY

  2040 Randall Cir, Winter Park, FL 32789
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  /2

  $1,495,000 Open Sat 12PM - 3PM

  • 3 Beds
  • 3.5 Baths
  • 2,738 Sq Ft

  901 Enclave Place, Winter Park, FL 32792

  Pre-Construction. To be built. Welcome to The Enclave at Winter Park—an exclusive collection of architecturally distinctive residences crafted by FG Schaub Custom Homes, blending timeless character with modern luxury. 901 Enclave Place (Lot1) is a thoughtfully designed courtyard home offering an elegant yet functional layout centered around private outdoor living. A charming covered front porch

  Laura Earl CORCORAN PREMIER REALTY

  901 Enclave Place, Winter Park, FL 32792
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  /25

  $499,500

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  1280 Gladiolas Dr, Winter Park, FL 32792

  One or more photo(s) has been virtually staged. Welcome to this beautifully updated 3-bedroom, 2-bath home with a New Roof 2021, screened-in pool, ideally located in the heart of Winter Park. Step inside to a fresh, move-in-ready feel with new flooring throughout, new light fixtures, new windows, and new doors—all thoughtfully selected to give the home a clean, modern look. The open, inviting

  Ian Trumbach FLORIDA PRESTIGIOUS HOMES INC

  1280 Gladiolas Dr, Winter Park, FL 32792
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  /10

  $1,689,000 New Construction

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

  1810 Hollywood Ave, Winter Park, FL 32789

  Under Construction. Estimated completion August!! Experience modern luxury living in the heart of Winter Park with this beautifully designed pool home at 1810 Hollywood Avenue. Offering 4 bedrooms, 3.5 bathrooms, and 2,604 square feet of thoughtfully planned living space, this residence blends high-end finishes with everyday functionality in one of Central Florida’s most sought-after locations.

  Ken Pozek REAL BROKER, LLC

  1810 Hollywood Ave, Winter Park, FL 32789
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  /31

  $485,000

  • 3 Beds
  • 2 Baths
  • 1,592 Sq Ft

  346 S Ranger Blvd, Winter Park, FL 32792

  PRIME LOCATION! Beautiful 3 Bedroom 2 Bathroom home is located in sought after Winter Park Pines with NO HOA and NO CDD. It is situated on a Corner Lot (0.22 Acre) and is a super short distance to the High Rated schools in Winter Park. The interior is extremely well kept with engineered wood floors, crown molding, and a beautiful glass entry door. There is a captivating white-washed stone

  Tetyana Vyushkina IMPERIAL REALTY OF FLORIDA INC

  346 S Ranger Blvd, Winter Park, FL 32792
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  /73

  $3,549,995

  • 4 Beds
  • 5 Baths
  • 3,658 Sq Ft

  1742 Temple Dr, Winter Park, FL 32789

  A New Standard of Modern Sophistication in Winter ParkIn a city known for its heritage, this ground-up architectural renovation emerges as a bold statement of modern luxury. Located within one of Winter Park’s most coveted enclaves, this four-bedroom, five-bathroom residence is not merely a place to live, but a meticulously crafted experience where high-design meets intuitive living.Step

  Mark Anthony Buot ROI AVE LLC

  1742 Temple Dr, Winter Park, FL 32789
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  /45

  $1,195,000

  • 5 Beds
  • 3.5 Baths
  • 3,490 Sq Ft

  2035 Lake Sue Dr, Orlando, FL 32803

  Welcome to Lake Sue Drive – A Rare Gem located in Beeman Park right in the heart of the Audubon Park Garden District. Situated on an oversized 0.49 lot (21,148 sf), this property has been owned by the same family for over 80 years. This charming home offers 4 bedrooms and 2.5 bathrooms in the main residence, along with a detached guest house (704 sq ft) complete with a full kitchen and

  Lisa Fleming FANNIE HILLMAN & ASSOCIATES

  2035 Lake Sue Dr, Orlando, FL 32803
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  /18

  $700,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 2,296 Sq Ft

  805 Nottingham St, Orlando, FL 32803

  One or more photo(s) has been virtually staged. Fully Renovated Orwin Manor Home | High-End Finishes | Major Systems Updated Located in desirable Orwin Manor, ideally positioned between the charm of College Park and the shopping, dining, and cultural destinations of Park Avenue, this fully renovated residence blends timeless character with high-end modern upgrades. The home has undergone an

  Anna Snyder CFL REAL ESTATE LLC

  805 Nottingham St, Orlando, FL 32803
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  /43

  $1,225,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 3 Baths
  • 2,292 Sq Ft

  67 Cypress Ln, Maitland, FL 32751

  Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majestic Cypress and Oak trees across from Lake Maitland in one of the area's most coveted neighborhoods. This architectural gem, expertly crafted from Western Red Cedar, offers two stories of thoughtfully designed living space with 4 bedrooms and 3 full baths.Step inside to discover hardwood floors flowing

  Kelly Price KELLY PRICE & COMPANY LLC

  67 Cypress Ln, Maitland, FL 32751
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  /59

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  1421 Sunnyside Dr, Maitland, FL 32751

  One or more photo(s) has been virtually staged. HUGE PRICE IMPROVEMENT Welcome to 1421 Sunnyside Drive, Maitland, FL, a beautifully maintained 4-bedroom, 2.5-bath single-family home with a pool, located on a corner lot directly adjacent to Winter Park. While this home carries a Maitland address, it sits just steps from Winter Park homes, offering the best of both locations. This move-in-ready

  Amanda Binns STRICKLAND REALTY GROUP INC

  1421 Sunnyside Dr, Maitland, FL 32751
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  $2,740,000 Open Sun 2PM - 5PM

  • 5 Beds
  • 5 Baths
  • 4,001 Sq Ft

  1411 Nottingham St, Orlando, FL 32803

  This one-of-a-kind, top-tier custom contemporary home in coveted Beverly Shores/Rose Isle delivers true turnkey luxury with exceptional finishes, premium cabinetry, high-end appliances, and fully integrated smart features throughout. The five-bedroom, three-and-a-half-bath main home plus a detached 384 SF casita (sixth bedroom) sits on a premium lot with unmatched access to scenic Mead

  Gwyn Clark FANNIE HILLMAN & ASSOCIATES

  1411 Nottingham St, Orlando, FL 32803
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  /31

  $784,000

  • 3 Beds
  • 3.5 Baths
  • 2,407 Sq Ft

  1732 Ridgewood Ave Unit S, Maitland, FL 32751

  This custom two-story townhome delivers what most properties in this category simply don’t; space, light, and a layout that actually makes sense. Open, airy, and thoughtfully designed, every detail feels intentional. Perfectly positioned between Maitland and Winter Park, you’re just minutes from Park Avenue, Winter Park Village, and some of the best dining and shopping in Central Florida. Step

  Brandon Geers COMPASS FLORIDA LLC

  1732 Ridgewood Ave Unit S, Maitland, FL 32751
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  $1,075,000

  • 4 Beds
  • 3.5 Baths
  • 2,598 Sq Ft

  1610 Lyndale Blvd, Maitland, FL 32751

  LOCATION, LOCATION, LOCATION! Ideally situated just off Park Avenue in the highly desirable Maitland/Winter Park area, this beautifully maintained home offers the perfect blend of charm, functionality, and convenience.Featuring 4 bedrooms and 3.5 bathrooms, the home welcomes you with elegant formal living and dining spaces enhanced by detailed trim work, crown molding, and updated lighting.

  Christian Del Pino CAPITAL EQUITY REAL ESTATE CO

  1610 Lyndale Blvd, Maitland, FL 32751
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  /20

  $308,000

  • 3 Beds
  • 2 Baths
  • 1,076 Sq Ft

  1074 Hamlet Dr, Maitland, FL 32751

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, convenience, and an unbeatable location. From the moment you step inside, you’ll notice the inviting layout featuring a spacious living area filled with natural light and a functional kitchen equipped with newer stainless steel appliances—perfect for everyday living and entertaining alike. The home sits on a

  Dominick Florio RE/MAX TOWN & COUNTRY REALTY

  1074 Hamlet Dr, Maitland, FL 32751
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  /34

  $615,000 Open Sun 2PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,410 Sq Ft

  4392 Wardell Place Unit 102, Orlando, FL 32814

  Welcome home to this charming, first floor, corner-unit condo in the heart of Baldwin Park! This impressive home features an oversized wrap around patio, an attached one car garage and has been fully updated throughout! Move in stress-free with a New HVAC (2022), New Paint (2022), all New Luxury Vinyl Plank Flooring throughout (2022), Brand new Refrigerator, Microwave, Range (2024), New Disposal

  Lindsey Hahn ALL REAL ESTATE & INVESTMENTS

  4392 Wardell Place Unit 102, Orlando, FL 32814

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