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Heritage Oak Park Homes, Villas and Condos for Sale in Port Charlotte, FL

Local market trends: View our Port Charlotte Market Report for regional home prices, supply, pending sales and months of inventory. These wider market trends are not specific to this community.

Welcome to Heritage Oak Park, a gated residential community in Port Charlotte known for its mature oak trees, winding streets, attractive lakes and relaxed Florida lifestyle. The neighborhood offers a choice of single-family homes, attached villas and condominium residences, with community amenities and a convenient location near shopping, dining and everyday services.

Aerial view of Heritage Oak Park pool and clubhouse in Port Charlotte
Heritage Oak Park clubhouse and swimming pool.

Living in Heritage Oak Park

Heritage Oak Park has a distinctive park-like setting, with shaded streets, landscaped grounds and scenic water views. Residents can enjoy the community clubhouse, heated swimming pool, fitness room, tennis and pickleball courts, shuffleboard, bocce, billiards, a library and walking paths. An activities director helps coordinate community events and social activities. Heritage Oak Park is not an age-restricted community.

Homes include traditional single-family residences and villas with garages, along with condominium buildings offering screened lanais and, in many cases, covered parking. Association responsibilities and fees differ by property type and section.

Understanding the Different Homes and Condos

Fee-simple villas: These are villa-style homes where the owner holds title to the home and its individual lot. Owners pay a homeowners association fee, but exterior building responsibilities can differ from those of a condominium.

Heritage Villas: These are villa-style residences with condominium ownership, even though they look and live much like a single-story home with an attached garage. The condominium association handles exterior maintenance and insurance as provided by its governing documents.

Waters Edge and Waterside Club: Both offer condominium living in separate associations. Waters Edge and Waterside Club have their own buildings, budgets, dues and rules. Both offer shared Heritage Oak Park amenities, but their condo fees and some property-specific restrictions differ.

Heritage Oak Park HOA, Condo and CDD Fees

Heritage Oak Park has mandatory association fees. Properties also have a Community Development District (CDD) assessment. Fees vary by property type and association.

Property Type / FeeQuarterlyAnnual Equivalent
Single-Family Home HOA$323-$651$1,292-$2,604
Fee-Simple Villa HOA$670$2,680
Heritage Villas Condo Fee$775$3,100
Waters Edge Condo Fee$925$3,700
Waterside Club Condo Fee$1,150-$1,364$4,600-$5,456
CDD AssessmentIncluded in tax bill$2,038

What association fees include: Common-area and grounds maintenance, community pool and recreational amenities. Depending on the property and association, fees may also include building exterior maintenance, insurance, pest control, water, sewer and other services. The CDD assessment is included in the property tax bill, so it should not be added again to the total property tax amount.

HOA, condominium and CDD fees, included services, and assessments may differ by association and property. Verify current dues, payment schedules, services and restrictions with the applicable associations and tax records.

Explore Heritage Oak Park Real Estate

Browse the current Heritage Oak Park homes, villas and condos for sale below. For more information about available properties, association requirements or scheduling a showing, contact Jason Ester with RE/MAX.

Heritage Oak Park Properties For Sale

1350 Old Oak Trail, Port Charlotte image
1350 Old Oak Trail, Port Charlotte $310,000 ▼

Welcome to Heritage Oak Park — one of Port Charlotte’s most sought-after gated communities, celebrated for its majestic mature oak trees and friendly, active lifestyle! ...

  • 3 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
1276 White Oak Trail Unit 3, Port Charlotte image
1276 White Oak Trail Unit 3, Port Charlotte $309,000 ▼

REDUCED! Heritage Oak Park Villa is a rare find, with only 16 of its kind on this peaceful cul-de-sac. Enjoy a private wooded view from the screened lanai in this spaciou...

  • 3 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
1448 Winding Oak Drive, Port Charlotte image
1448 Winding Oak Drive, Port Charlotte $265,000

New on market! 2/2/2 private villa in a quiet community. Lots of updates and well maintained. New ceiling fans, lighting, showers and more. Bar in kitchen for entertainin...

  • 2 Beds
  • 2 Baths
  • Heritage Oak SubDv.
  • 33948 Zip Code
1253 Red Oak Lane, Port Charlotte image
1253 Red Oak Lane, Port Charlotte $260,000

Welcome to your new home in the desirable gated community of Heritage Oak Park! Surrounded by native oak trees and winding streets, this neighborhood offers a peaceful, c...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
1284 Green Oak Trail, Port Charlotte image
1284 Green Oak Trail, Port Charlotte $250,000

Welcome to your new home in the desirable gated community of Heritage Oak Park. This sought-after “A” villa offers 2 bedrooms, 2 baths, a bonus room, and a spacious 2-car...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
1337 Red Oak Lane, Port Charlotte image
1337 Red Oak Lane, Port Charlotte $245,000

Welcome to this beautifully furnished 2-bedroom, 2-bath home with a den in desirable Heritage Oak Park. Offering an open-concept layout, well-equipped kitchen with breakf...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19300 Water Oak Drive Unit 102, Port Charlotte image
19300 Water Oak Drive Unit 102, Port Charlotte — 19300 $239,900 ▼

PRICE REUDUCED! THIS IS A MUST SEE! Beautiful almost totally upgraded first-floor condo located in popular gated Heritage Oak Park community. This spacious 1,227 sq. ft. ...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19355 Water Oak Drive Unit 101, Port Charlotte image
19355 Water Oak Drive Unit 101, Port Charlotte — 19355 $219,900

This rare lakefront 3-bedroom, 2-bath condo in the sought-after Heritage Oak Park is a true gem! Located on the first floor, it offers a stunning lake view and features o...

  • 3 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19385 Water Oak Drive Unit 301, Port Charlotte image
19385 Water Oak Drive Unit 301, Port Charlotte — 19385 $209,900 ▼

REDUCED! Rarely available top-floor 3-bedroom, 2-bath condo in the desirable gated Heritage Oak Park! This end unit has extra side windows, making it bright and airy. The...

  • 3 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19310 Water Oak Drive Unit 203, Port Charlotte image
19310 Water Oak Drive Unit 203, Port Charlotte — 19310 $205,000 ▼

Welcome to this well-maintained 2-bedroom, 2-bath second-floor condominium offering over 1,000 square feet of comfortable living space with an open-concept design ideal f...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19310 Water Oak Drive Unit 103, Port Charlotte image
19310 Water Oak Drive Unit 103, Port Charlotte — E $205,000 ▼

Enjoy easy Florida living in this well-kept 2-bedroom, 2-bath condo in Heritage Oak Park, known for reasonable HOA fees and great community amenities. Inside, the home fe...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19335 Water Oak Drive Unit 301, Port Charlotte image
19335 Water Oak Drive Unit 301, Port Charlotte — G $198,000 ▼

Welcome to this beautifully maintained 3-bedroom, 2-bathroom condo in the highly sought-after gated community of Heritage Oak Park. Located on the third-floor corner, th...

  • 3 Beds
  • 2 Baths
  • Waterside Club At Heritage Oak Park SubDv.
  • 33948 Zip Code
19355 Water Oak Drive Unit 303, Port Charlotte image
19355 Water Oak Drive Unit 303, Port Charlotte — 1 $170,000 ▼

TOP-FLOOR LAKEVIEW CONDO IN WATERSIDE II AT HERITAGE OAK PARK Enjoy peaceful lakefront living in this beautifully updated 2 bedroom, 2 bathroom third-floor condo locat...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19325 Water Oak Drive Unit 204, Port Charlotte image
19325 Water Oak Drive Unit 204, Port Charlotte — 19325 $149,500

Enjoy resort-style living at Heritage Oak Park in this beautifully maintained, fully furnished condo with a gorgeous lake view! Used seasonally by the owner, the open flo...

  • 2 Beds
  • 1 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
19345 Water Oak Drive Unit 106, Port Charlotte image
19345 Water Oak Drive Unit 106, Port Charlotte — 19345 $139,000

Priced to sell fast! Move right into this first-floor lakefront condo in the popular gated community of Heritage Oak Park. Enjoy a fantastic lake view from the screened l...

  • 2 Beds
  • 2 Baths
  • Heritage Oak Park SubDv.
  • 33948 Zip Code
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Jason Ester
RE/MAX Alliance Group

14850 Tamiami Trail
North Port, FL 34287

941-376-6626
Email Jason

© 2026 Jason Ester. RE/MAX Alliance Group.
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